Turningleafrealestate.net Search Results

$1,595,000

Where the water meets the good life — welcome to elevated island living in the heart of Holmes Beach. Offered completely furnished and truly turnkey, this beautifully reimagined 2BD/2BA retreat blends timeless coastal character with modern comfort, ready for you to simply arrive, unpack, and begin. Renovated top to bottom, the light-filled, open-concept interior is finished with recessed lighting, designer coastal touches, and effortless flow. At its center is a stunning remodeled kitchen — custom cabinetry, expansive quartz countertops, stainless steel appliances, and an oversized island with seating that opens seamlessly to the dining and living spaces, made for slow mornings and lively evenings alike. The serene primary suite offers a spa-inspired en-suite bath, while a generous guest bedroom and beautifully renovated guest bath welcome family and friends in comfort. Beyond the walls awaits your private tropical sanctuary: lush, mature landscaping with low maintenance turf framing a heated saltwater pool, an expansive patio for sun-soaked afternoons, and a refreshing outdoor shower. For the boater, this is the dream — deep-water canal frontage, a private dock with a 10,000-lb lift, fish-cleaning station, and no bridge obstructions for swift, open-water access to Tampa Bay and the Gulf. Moments from powder-soft Gulf beaches and the shops and restaurants of Anna Maria Island by car, bike, or golf cart, this is an exceptional residence offering a wonderful opportunity to live the waterfront lifestyle every day — whether as a full-time home or an unforgettable coastal getaway.

2 Beds ⋅ 2 Baths ⋅ Bay Palms SubDv. ⋅ 34217 Zip Code

Where the water meets the good life — welcome to elevated island living in the heart of Holmes Beach. Offered completely furnished and truly turnkey, this beautifully reimagined 2BD/2BA retreat blends timeless coastal character with modern comfort, ready for you to simply arrive, unpack, and begin. Renovated top to bottom, the light-filled, open-concept interior is finished with recessed lighting, designer coastal touches, and effortless flow. At its center is a stunning remodeled kitchen — custom cabinetry, expansive quartz countertops, stainless steel appliances, and an oversized island with seating that opens seamlessly to the dining and living spaces, made for slow mornings and lively evenings alike. The serene primary suite offers a spa-inspired en-suite bath, while a generous guest bedroom and beautifully renovated guest bath welcome family and friends in comfort. Beyond the walls awaits your private tropical sanctuary: lush, mature landscaping with low maintenance turf framing a heated saltwater pool, an expansive patio for sun-soaked afternoons, and a refreshing outdoor shower. For the boater, this is the dream — deep-water canal frontage, a private dock with a 10,000-lb lift, fish-cleaning station, and no bridge obstructions for swift, open-water access to Tampa Bay and the Gulf. Moments from powder-soft Gulf beaches and the shops and restaurants of Anna Maria Island by car, bike, or golf cart, this is an exceptional residence offering a wonderful opportunity to live the waterfront lifestyle every day — whether as a full-time home or an unforgettable coastal getaway.

520 69th Street, Holmes Beach

$2,495,000

Welcome to Tidal Daze, a beautifully designed coastal sanctuary poised just a short stroll from the sugar-sand shores of Holmes Beach—where turquoise water, gentle Gulf breezes, and legendary sunsets become part of your everyday rhythm. A proven vacation rental with an established income history, this exceptional 4BD/3.5BA residence offers a rare balance of refined style, easy comfort, and lasting investment value. Sunlight pours through walls of windows and a central skylight, washing the open gathering spaces in a bright, airy glow that carries throughout the home. The graceful floor plan unfolds into both a welcoming family room and a separate living room—generous room to entertain, unwind, and settle in after a barefoot day by the water. The kitchen flows seamlessly into the main living areas, while an expansive wrap-around porch invites slow morning coffee, alfresco dining, and golden evening sunsets framed by lush tropical landscaping. Beyond the doors, a private backyard is composed for effortless island living: a sparkling pool, a covered entertaining area, and low-maintenance grounds that give you back your time for the Florida lifestyle. Ample driveway parking welcomes family and guests with ease, while a durable metal roof lends enduring value and coastal character. Best of all, the beach is close enough to leave the car behind—slip on your sandals, wander to the shoreline in minutes, and let sunrise walks and toes-in-the-sand afternoons unfold whenever the mood strikes. Whether you envision a primary residence, a serene second home, or a proven income-producing retreat, Tidal Daze presents an extraordinary opportunity in one of Anna Maria Island's most coveted enclaves—moments from the beach, celebrated dining, boutique shopping, and all the magic of island life.

4 Beds ⋅ 4 Baths ⋅ West Wind Shores SubDv. ⋅ 34217 Zip Code

Welcome to Tidal Daze, a beautifully designed coastal sanctuary poised just a short stroll from the sugar-sand shores of Holmes Beach—where turquoise water, gentle Gulf breezes, and legendary sunsets become part of your everyday rhythm. A proven vacation rental with an established income history, this exceptional 4BD/3.5BA residence offers a rare balance of refined style, easy comfort, and lasting investment value. Sunlight pours through walls of windows and a central skylight, washing the open gathering spaces in a bright, airy glow that carries throughout the home. The graceful floor plan unfolds into both a welcoming family room and a separate living room—generous room to entertain, unwind, and settle in after a barefoot day by the water. The kitchen flows seamlessly into the main living areas, while an expansive wrap-around porch invites slow morning coffee, alfresco dining, and golden evening sunsets framed by lush tropical landscaping. Beyond the doors, a private backyard is composed for effortless island living: a sparkling pool, a covered entertaining area, and low-maintenance grounds that give you back your time for the Florida lifestyle. Ample driveway parking welcomes family and guests with ease, while a durable metal roof lends enduring value and coastal character. Best of all, the beach is close enough to leave the car behind—slip on your sandals, wander to the shoreline in minutes, and let sunrise walks and toes-in-the-sand afternoons unfold whenever the mood strikes. Whether you envision a primary residence, a serene second home, or a proven income-producing retreat, Tidal Daze presents an extraordinary opportunity in one of Anna Maria Island's most coveted enclaves—moments from the beach, celebrated dining, boutique shopping, and all the magic of island life.

203 72nd Street, Holmes Beach

$5,995,000

Tucked along an extraordinary 225 feet of waterfront, this custom coastal retreat distills the very essence of island living—breathtaking water views, exceptional privacy, and thoughtfully designed spaces that move effortlessly between serene relaxation and spirited entertaining. A palm-lined driveway sets the tone, where timeless architecture and lush tropical landscaping leave an unforgettable first impression. This residence carries rare local significance as the very first custom home built by Ross Built Construction, masterfully designed by renowned architect Gene Aubry. It stands as a lasting testament to their craftsmanship and creativity—and their contribution to luxury coastal living on Anna Maria Island. Their influence resonates throughout: a thoughtful floor plan, an exceptional command of natural light, and a seamless connection between indoor and outdoor living. Inside, travertine tile and hand-scraped maple flooring flow through a light-filled interior crowned by soaring vaulted ceilings in the living and kitchen areas. The chef's kitchen is as functional as it is beautiful, appointed with stone countertops, copper sinks, a gas range with pot filler, premium appliances, and a generous center island that anchors the home's main gathering spaces. Five spacious ensuite bedrooms, a dedicated den/office, and an upstairs bonus room offer effortless flexibility for family and guests. The primary suite is a private sanctuary unto itself, featuring a remodeled spa-inspired bath with custom built-in shelving and elegant finishes throughout. Designed to embrace the waterfront lifestyle, expansive glass doors open to an impressive 1,400-square-foot veranda overlooking the sparkling saltwater pool and tranquil waterways beyond. Boaters will appreciate the private dock and 10,000-lb boat lift for effortless access to open water, while an oversized three-car garage, elevator, impact-rated windows and doors, Sonos sound system, mosquito misting system, rainwater cistern, and exterior irrigation system deliver convenience and lasting peace of mind. Perfectly positioned in the heart of Holmes Beach, the property is just moments from the sugar-sand beaches of the Gulf, beloved local restaurants, boutiques, and island shops—a rare pairing of private waterfront sanctuary and walkable island convenience. Whether savoring spectacular sunsets from the veranda, entertaining poolside, strolling to nearby dining, or setting out for a day on the water, this remarkable residence offers something exceedingly rare: not only an extraordinary waterfront home, but a meaningful piece of island history, where inspired architecture, enduring craftsmanship, and an unrivaled setting come together in perfect harmony.

5 Beds ⋅ 5 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code

Tucked along an extraordinary 225 feet of waterfront, this custom coastal retreat distills the very essence of island living—breathtaking water views, exceptional privacy, and thoughtfully designed spaces that move effortlessly between serene relaxation and spirited entertaining. A palm-lined driveway sets the tone, where timeless architecture and lush tropical landscaping leave an unforgettable first impression. This residence carries rare local significance as the very first custom home built by Ross Built Construction, masterfully designed by renowned architect Gene Aubry. It stands as a lasting testament to their craftsmanship and creativity—and their contribution to luxury coastal living on Anna Maria Island. Their influence resonates throughout: a thoughtful floor plan, an exceptional command of natural light, and a seamless connection between indoor and outdoor living. Inside, travertine tile and hand-scraped maple flooring flow through a light-filled interior crowned by soaring vaulted ceilings in the living and kitchen areas. The chef's kitchen is as functional as it is beautiful, appointed with stone countertops, copper sinks, a gas range with pot filler, premium appliances, and a generous center island that anchors the home's main gathering spaces. Five spacious ensuite bedrooms, a dedicated den/office, and an upstairs bonus room offer effortless flexibility for family and guests. The primary suite is a private sanctuary unto itself, featuring a remodeled spa-inspired bath with custom built-in shelving and elegant finishes throughout. Designed to embrace the waterfront lifestyle, expansive glass doors open to an impressive 1,400-square-foot veranda overlooking the sparkling saltwater pool and tranquil waterways beyond. Boaters will appreciate the private dock and 10,000-lb boat lift for effortless access to open water, while an oversized three-car garage, elevator, impact-rated windows and doors, Sonos sound system, mosquito misting system, rainwater cistern, and exterior irrigation system deliver convenience and lasting peace of mind. Perfectly positioned in the heart of Holmes Beach, the property is just moments from the sugar-sand beaches of the Gulf, beloved local restaurants, boutiques, and island shops—a rare pairing of private waterfront sanctuary and walkable island convenience. Whether savoring spectacular sunsets from the veranda, entertaining poolside, strolling to nearby dining, or setting out for a day on the water, this remarkable residence offers something exceedingly rare: not only an extraordinary waterfront home, but a meaningful piece of island history, where inspired architecture, enduring craftsmanship, and an unrivaled setting come together in perfect harmony.

526 56th Street, Holmes Beach

$1,200,000

Location, location, and island living at its best! Enjoy this elevated 2-bedroom 2 bath home located in central Holmes Beach on Anna Maria Island. You are three houses away from beach access and all of a 5 minute walk to watch sunsets and relax on the Gulf Beaches. This home has been renovated, and is turnkey furnished in a beachy décor to continue as a productive vacation rental or bring your things and move right in! The open floor plan includes a kitchen that opens to living room and dining area as well as the outside deck. The large 10x19 open front porch is perfect for entertaining with friends or family. The yard is low maintenance, and the back yard is completely fenced in with a brand-new heated swimming pool and turf. Downstairs is an open area that you can make into your own mancave or entertainment area. Ideas are unlimited. The location makes this home a perfect investment property.

2 Beds ⋅ 2 Baths ⋅ West Wind Shores SubDv. ⋅ 34217 Zip Code

Location, location, and island living at its best! Enjoy this elevated 2-bedroom 2 bath home located in central Holmes Beach on Anna Maria Island. You are three houses away from beach access and all of a 5 minute walk to watch sunsets and relax on the Gulf Beaches. This home has been renovated, and is turnkey furnished in a beachy décor to continue as a productive vacation rental or bring your things and move right in! The open floor plan includes a kitchen that opens to living room and dining area as well as the outside deck. The large 10x19 open front porch is perfect for entertaining with friends or family. The yard is low maintenance, and the back yard is completely fenced in with a brand-new heated swimming pool and turf. Downstairs is an open area that you can make into your own mancave or entertainment area. Ideas are unlimited. The location makes this home a perfect investment property.

207 71st Street Unit E, Holmes Beach

$880,000

BUY ONE OR BOTH SIDES OF THIS DUPLEX PROPERTY. STEPS TO THE BEACH AND LOCATED IN A WEEKLY RENTAL ZONE! Exceptional Island Investment Opportunity Just a short walk to the Beach! Welcome to 202 Peacock Lane, Unit B, a beautifully remodeled half-duplex perfectly positioned for vacation rental investors, second-home buyers, and those seeking the ultimate Anna Maria Island lifestyle. This spacious three-bedroom, two-bath residence with an impressive three-car garage configuration offers the ideal combination of prime island location, investment potential, and coastal living. Located just one block from the sugar-sand beaches of Anna Maria Island, this property is an outstanding opportunity for those seeking a vacation home, short-term rental investment, income-producing property, or full-time beach residence. Completely renovated from top to bottom, this turnkey property features a new roof, new HVAC system, new water heater, new flooring, new walls, and a stunning designer kitchen, showcasing stainless steel appliances, abundant custom cabinetry, and upgraded countertops. The home also boasts two beautifully updated bathrooms featuring custom vanities and stylish finishes. Nearly everything in this property is new or newer, offering peace of mind and low-maintenance ownership. The spacious layout comfortably accommodates families and groups, making it highly desirable as a high-demand vacation rental property. The expansive garage area includes a two-car tandem garage plus a separate 3 car ove sized garage, lockout garage, providing exceptional space for vehicles, golf carts, beach gear, bicycles, owner's storage, and more. Plus, driveway parking for possible 4 more cars. The versatile space beneath the home (2 car tandem garage space) offers endless possibilities, including a game room, entertainment area, additional living space, or covered parking. Outside, the private fenced backyard offers room to create your own tropical oasis with potential space for a pool (buyer to verify). Location is everything, and this property delivers! Leave the car and golf cart behind you're just steps away from world famous Gulf beaches, waterfront dining, boutique shopping, local attractions, and island entertainment. Everything needed for the perfect island vacation experience is within walking distance, making this property exceptionally attractive to both guests and owners. Sold furnished with a few exclusions. Rental or move in ready! Whether you're expanding your real estate portfolio, searching for a beach investment property, looking for a turnkey vacation rental, or dreaming of owning your own piece of paradise on Anna Maria Island, this exceptional property checks every box. Rarely do island properties this close to the beach offer extensive updates, exceptional walkability, flexible living space, and outstanding rental potential.

3 Beds ⋅ 2 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code

BUY ONE OR BOTH SIDES OF THIS DUPLEX PROPERTY. STEPS TO THE BEACH AND LOCATED IN A WEEKLY RENTAL ZONE! Exceptional Island Investment Opportunity Just a short walk to the Beach! Welcome to 202 Peacock Lane, Unit B, a beautifully remodeled half-duplex perfectly positioned for vacation rental investors, second-home buyers, and those seeking the ultimate Anna Maria Island lifestyle. This spacious three-bedroom, two-bath residence with an impressive three-car garage configuration offers the ideal combination of prime island location, investment potential, and coastal living. Located just one block from the sugar-sand beaches of Anna Maria Island, this property is an outstanding opportunity for those seeking a vacation home, short-term rental investment, income-producing property, or full-time beach residence. Completely renovated from top to bottom, this turnkey property features a new roof, new HVAC system, new water heater, new flooring, new walls, and a stunning designer kitchen, showcasing stainless steel appliances, abundant custom cabinetry, and upgraded countertops. The home also boasts two beautifully updated bathrooms featuring custom vanities and stylish finishes. Nearly everything in this property is new or newer, offering peace of mind and low-maintenance ownership. The spacious layout comfortably accommodates families and groups, making it highly desirable as a high-demand vacation rental property. The expansive garage area includes a two-car tandem garage plus a separate 3 car ove sized garage, lockout garage, providing exceptional space for vehicles, golf carts, beach gear, bicycles, owner's storage, and more. Plus, driveway parking for possible 4 more cars. The versatile space beneath the home (2 car tandem garage space) offers endless possibilities, including a game room, entertainment area, additional living space, or covered parking. Outside, the private fenced backyard offers room to create your own tropical oasis with potential space for a pool (buyer to verify). Location is everything, and this property delivers! Leave the car and golf cart behind you're just steps away from world famous Gulf beaches, waterfront dining, boutique shopping, local attractions, and island entertainment. Everything needed for the perfect island vacation experience is within walking distance, making this property exceptionally attractive to both guests and owners. Sold furnished with a few exclusions. Rental or move in ready! Whether you're expanding your real estate portfolio, searching for a beach investment property, looking for a turnkey vacation rental, or dreaming of owning your own piece of paradise on Anna Maria Island, this exceptional property checks every box. Rarely do island properties this close to the beach offer extensive updates, exceptional walkability, flexible living space, and outstanding rental potential.

202 Peacock Lane Unit B, Holmes Beach

$2,995,000

Experience the ultimate island lifestyle in this exquisite coastal retreat on Anna Maria Island. Nestled on one of the island’s most breathtaking tropical lots, this beautifully updated four-bedroom, three-and-a-half-bath residence offers deepwater canal access to the Gulf and the perfect blend of luxury, comfort, and waterfront living. Sold fully furnished and including a golf cart for added convenience, the home underwent an extensive remodel in 2021 and has been thoughtfully upgraded throughout. Recent improvements include a new seawall and dock with a 10,000-pound boat lift upgraded in 2024, as well as a whole-house propane generator installed in 2026. The property has also had no flood damage. Inside, expansive wood-look plank tile flooring creates a warm and inviting atmosphere throughout the home. The stunning chef’s kitchen features quartz countertops, custom cabinetry, and premium high-end appliances. The main living level includes three spacious guest bedrooms, while the entire upper level is dedicated to a luxurious primary suite complete with dual vanities, a spa-inspired bathroom, and an oversized walk-in closet with washer/dryer. Additional highlights include a 200-square-foot insulated storage attic, a private man cave, and a unique indoor entertainment space featuring an indoor grill, bar, and television area that flows seamlessly to the resort-style pool and outdoor living space. From your private dock, enjoy direct boating access to nearby beaches, waterfront dining, and all the charm that island living has to give. This exceptional property is a rare opportunity to own a true waterfront paradise on one of Florida’s most sought-after islands. Don’t miss your chance to make this dream home your reality.

4 Beds ⋅ 4 Baths ⋅ Bay Palms SubDv. ⋅ 34217 Zip Code

Experience the ultimate island lifestyle in this exquisite coastal retreat on Anna Maria Island. Nestled on one of the island’s most breathtaking tropical lots, this beautifully updated four-bedroom, three-and-a-half-bath residence offers deepwater canal access to the Gulf and the perfect blend of luxury, comfort, and waterfront living. Sold fully furnished and including a golf cart for added convenience, the home underwent an extensive remodel in 2021 and has been thoughtfully upgraded throughout. Recent improvements include a new seawall and dock with a 10,000-pound boat lift upgraded in 2024, as well as a whole-house propane generator installed in 2026. The property has also had no flood damage. Inside, expansive wood-look plank tile flooring creates a warm and inviting atmosphere throughout the home. The stunning chef’s kitchen features quartz countertops, custom cabinetry, and premium high-end appliances. The main living level includes three spacious guest bedrooms, while the entire upper level is dedicated to a luxurious primary suite complete with dual vanities, a spa-inspired bathroom, and an oversized walk-in closet with washer/dryer. Additional highlights include a 200-square-foot insulated storage attic, a private man cave, and a unique indoor entertainment space featuring an indoor grill, bar, and television area that flows seamlessly to the resort-style pool and outdoor living space. From your private dock, enjoy direct boating access to nearby beaches, waterfront dining, and all the charm that island living has to give. This exceptional property is a rare opportunity to own a true waterfront paradise on one of Florida’s most sought-after islands. Don’t miss your chance to make this dream home your reality.

522 68th Street, Holmes Beach

$1,085,000

The ultimate island investment or low-maintenance personal paradise has arrived! This fully remodeled 3-bedroom, 2-bathroom villa offers the rare freedom of zero HOA fees combined with high-income weekly rental potential. Originally built with solid mid-century bones, the property carries an effective year built of 2009 and has just undergone a spectacular, top-to-bottom luxury transformation. Step inside to a bright, airy great room boasting vaulted ceilings and elegant crown molding throughout. The stunning chef’s kitchen features a massive island with counter seating, brand-new cabinetry, quartz countertops, and all-new Stainless Steel appliances. Total peace of mind is yours with BRAND-NEW impact-rated windows, exterior doors, and sliding glass doors, complemented by fresh interior/exterior paint and new ceramic tile flooring. The outdoor space is a private tropical oasis, showcasing fresh landscaping with a full irrigation system/landscape lighting and a fully fenced yard. The sparkling heated pool is ready for year-round enjoyment with a brand-new pool heater and pool pump. Offered completely turnkey furnished, this island gem is move in and rental-ready from day one!

3 Beds ⋅ 2 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code

The ultimate island investment or low-maintenance personal paradise has arrived! This fully remodeled 3-bedroom, 2-bathroom villa offers the rare freedom of zero HOA fees combined with high-income weekly rental potential. Originally built with solid mid-century bones, the property carries an effective year built of 2009 and has just undergone a spectacular, top-to-bottom luxury transformation. Step inside to a bright, airy great room boasting vaulted ceilings and elegant crown molding throughout. The stunning chef’s kitchen features a massive island with counter seating, brand-new cabinetry, quartz countertops, and all-new Stainless Steel appliances. Total peace of mind is yours with BRAND-NEW impact-rated windows, exterior doors, and sliding glass doors, complemented by fresh interior/exterior paint and new ceramic tile flooring. The outdoor space is a private tropical oasis, showcasing fresh landscaping with a full irrigation system/landscape lighting and a fully fenced yard. The sparkling heated pool is ready for year-round enjoyment with a brand-new pool heater and pool pump. Offered completely turnkey furnished, this island gem is move in and rental-ready from day one!

324 64th Street, Holmes Beach

$994,000

This home is a renovated 2-bedroom, 2-bathroom with a private den. The home has an open concept with the kitchen, dining area and living room. The primary suite has an en-suite bathroom. It has a private backyard and a heated and chilled pool. There is an upper deck and a lower covered outdoor living and dining area. It is in a weekly rental zone and has good history and 5-star reviews. This lovely property is convenient to the beach and in a very quiet Holmes Beach residential neighborhood. It has one shared wall with the unit next door that was double insulated during renovation to reduce noise. It's just a short walk to the many shops and restaurants of downtown Holmes Beach, as well as the Island’s only dog park. There is a storage room that includes a ping pong table, a beach cart, beach toys and lots of beach equipment and a propane grill and outdoor propane fire pit ready to enjoy.

2 Beds ⋅ 2 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code

This home is a renovated 2-bedroom, 2-bathroom with a private den. The home has an open concept with the kitchen, dining area and living room. The primary suite has an en-suite bathroom. It has a private backyard and a heated and chilled pool. There is an upper deck and a lower covered outdoor living and dining area. It is in a weekly rental zone and has good history and 5-star reviews. This lovely property is convenient to the beach and in a very quiet Holmes Beach residential neighborhood. It has one shared wall with the unit next door that was double insulated during renovation to reduce noise. It's just a short walk to the many shops and restaurants of downtown Holmes Beach, as well as the Island’s only dog park. There is a storage room that includes a ping pong table, a beach cart, beach toys and lots of beach equipment and a propane grill and outdoor propane fire pit ready to enjoy.

308 60th Street Unit A, Holmes Beach

$2,790,000

Waterfront luxury, exceptional boating, and true peace of mind come together at this beautifully updated Grand Canal home in Holmes Beach on Anna Maria Island. Perfectly positioned on one of the island's most sought-after deep-water canals with no fixed bridges, this 4-bedroom, 3-bath residence offers direct access to Tampa Bay and the Gulf of Mexico, making it an outstanding opportunity for boating enthusiasts. Recently inspected this property has a clean report card and in excellent condition. Meticulously maintained and extensively updated, this furnished home (with a few exclusions) is truly move-in ready. Designed to embrace the island lifestyle, its desirable southern exposure fills the home with natural light while walls of impact-rated sliding glass doors frame breathtaking canal views and create seamless indoor-outdoor living. The private tropical setting features mature landscaping, a producing mango tree, and a fenced backyard centered around a heated pool, oversized spa, and an impressive 12' x 60' dock with a 20,000-pound boat lift—perfect for entertaining, relaxing, or setting off for a day on the water. Inside, white Italian oak-inspired plank tile flooring flows throughout the home. The spacious family room showcases vaulted tongue-and-groove ceilings and a custom entertaining bar, while the beautifully appointed chef's kitchen offers quartz countertops, custom cabinetry with appliance garages, a large center island, and premium Fisher & Paykel and Bosch appliances. The thoughtfully designed floor plan includes spacious guest accommodations, a hidden laundry room, and a private waterfront primary suite featuring a walk-in closet, water closet, and direct access to a peaceful outdoor retreat overlooking the canal. A flexible den easily functions as a fourth bedroom, home office, or additional guest space. Extensive improvements completed in 2021 provide exceptional quality and lasting value, including a new roof, impact windows and sliding glass doors, updated dock and pilings, and all-new Schedule 40 drain piping beneath the slab. In 2025, a 26KW whole-house generator with a 500-gallon propane tank was added, providing dependable backup power. The covered waterfront lanai is already plumbed and wired for a future outdoor kitchen, while the oversized garage, carport, and generous parking offer convenience for family and guests alike. Located in the heart of Holmes Beach, just minutes from Anna Maria Island's world-famous beaches, waterfront restaurants, boutique shopping, and island attractions, this exceptional property offers one of the finest boating locations on the island. Combining luxury, quality construction, extensive recent improvements, and remarkable waterfront access, this is a rare opportunity to own an exceptional canal-front home where all the hard work has already been done.** Property information received from third-party sources is considered reliable but is not guaranteed. All information should be independently verified by buyers and buyer's agent.

4 Beds ⋅ 3 Baths ⋅ Bay Palms SubDv. ⋅ 34217 Zip Code

Waterfront luxury, exceptional boating, and true peace of mind come together at this beautifully updated Grand Canal home in Holmes Beach on Anna Maria Island. Perfectly positioned on one of the island's most sought-after deep-water canals with no fixed bridges, this 4-bedroom, 3-bath residence offers direct access to Tampa Bay and the Gulf of Mexico, making it an outstanding opportunity for boating enthusiasts. Recently inspected this property has a clean report card and in excellent condition. Meticulously maintained and extensively updated, this furnished home (with a few exclusions) is truly move-in ready. Designed to embrace the island lifestyle, its desirable southern exposure fills the home with natural light while walls of impact-rated sliding glass doors frame breathtaking canal views and create seamless indoor-outdoor living. The private tropical setting features mature landscaping, a producing mango tree, and a fenced backyard centered around a heated pool, oversized spa, and an impressive 12' x 60' dock with a 20,000-pound boat lift—perfect for entertaining, relaxing, or setting off for a day on the water. Inside, white Italian oak-inspired plank tile flooring flows throughout the home. The spacious family room showcases vaulted tongue-and-groove ceilings and a custom entertaining bar, while the beautifully appointed chef's kitchen offers quartz countertops, custom cabinetry with appliance garages, a large center island, and premium Fisher & Paykel and Bosch appliances. The thoughtfully designed floor plan includes spacious guest accommodations, a hidden laundry room, and a private waterfront primary suite featuring a walk-in closet, water closet, and direct access to a peaceful outdoor retreat overlooking the canal. A flexible den easily functions as a fourth bedroom, home office, or additional guest space. Extensive improvements completed in 2021 provide exceptional quality and lasting value, including a new roof, impact windows and sliding glass doors, updated dock and pilings, and all-new Schedule 40 drain piping beneath the slab. In 2025, a 26KW whole-house generator with a 500-gallon propane tank was added, providing dependable backup power. The covered waterfront lanai is already plumbed and wired for a future outdoor kitchen, while the oversized garage, carport, and generous parking offer convenience for family and guests alike. Located in the heart of Holmes Beach, just minutes from Anna Maria Island's world-famous beaches, waterfront restaurants, boutique shopping, and island attractions, this exceptional property offers one of the finest boating locations on the island. Combining luxury, quality construction, extensive recent improvements, and remarkable waterfront access, this is a rare opportunity to own an exceptional canal-front home where all the hard work has already been done.** Property information received from third-party sources is considered reliable but is not guaranteed. All information should be independently verified by buyers and buyer's agent.

501 68th Street, Holmes Beach

$3,295,000

Tucked away in a quiet area of the island in a lush, tropical setting just moments from the beach, this beautiful 5BD/4BA residence captures the essence of coastal living with effortless style and thoughtful functionality, offering an exceptional opportunity in a desirable weekly rental zone. Framed by swaying palms and vibrant landscaping, the home welcomes you into a light-filled interior where a spacious living room with soaring ceilings, elegant plantation shutters, and a cozy gas fireplace creates an inviting space to gather and unwind. The open flow continues into a well appointed kitchen equipped with everything the family chef could want including a dining nook, but that family chef will love the scullery area with an additional stove and dishwasher for all the family gatherings. The scullery opens to the exterior where the outdoor grill and pizza oven are right at your finger tips. Two ensuite bedrooms, including a serene primary suite, offer comfort and privacy, while the remaining spacious bedrooms provide generous accommodations for the whole family. Step outside to a private pool area designed for soaking up the Florida sunshine, featuring a pool chiller for year-round comfort and surrounded by ample space for lounging and entertaining, along with two convenient outdoor showers. Practical features abound with natural gas service, a whole house generator, a durable metal roof, impact windows and more. There is also an exterior storage shed for all the beach toys, and abundant parking including two circular driveways on this corner lot. Located in the heart of Holmes Beach this location can’t be beat with a short walk to local shops, eateries and most importantly the sugar white sand and turquoise gulf waters.

5 Beds ⋅ 4 Baths ⋅ Holmes Gulf To Bay Dev Subdivison SubDv. ⋅ 34217 Zip Code

Tucked away in a quiet area of the island in a lush, tropical setting just moments from the beach, this beautiful 5BD/4BA residence captures the essence of coastal living with effortless style and thoughtful functionality, offering an exceptional opportunity in a desirable weekly rental zone. Framed by swaying palms and vibrant landscaping, the home welcomes you into a light-filled interior where a spacious living room with soaring ceilings, elegant plantation shutters, and a cozy gas fireplace creates an inviting space to gather and unwind. The open flow continues into a well appointed kitchen equipped with everything the family chef could want including a dining nook, but that family chef will love the scullery area with an additional stove and dishwasher for all the family gatherings. The scullery opens to the exterior where the outdoor grill and pizza oven are right at your finger tips. Two ensuite bedrooms, including a serene primary suite, offer comfort and privacy, while the remaining spacious bedrooms provide generous accommodations for the whole family. Step outside to a private pool area designed for soaking up the Florida sunshine, featuring a pool chiller for year-round comfort and surrounded by ample space for lounging and entertaining, along with two convenient outdoor showers. Practical features abound with natural gas service, a whole house generator, a durable metal roof, impact windows and more. There is also an exterior storage shed for all the beach toys, and abundant parking including two circular driveways on this corner lot. Located in the heart of Holmes Beach this location can’t be beat with a short walk to local shops, eateries and most importantly the sugar white sand and turquoise gulf waters.

5701 Carissa Street, Holmes Beach

$3,400,000

Experience elevated coastal living in this brand-new, designer-finished 4BR/4.5BA luxury home located just a 5-minute walk to the pristine beaches of Anna Maria Island. Thoughtfully crafted with high-end finishes and a bright, open-concept layout, this residence blends modern elegance with relaxed island charm. Currently utilized as a successful short term vacation rental with proven rental revenue. 4 spacious ensuite bedrooms, including three king suites with walk-in showers Gorgeous open living area with abundant natural light and upscale coastal décor Chef’s kitchen featuring modern cabinetry, stone counters, and stainless appliances Private heated pool with in-ground spa, surrounded by lush tropical landscaping Expansive rooftop deck offering panoramic views and unforgettable sunsets Fully furnished with professionally curated interiors Designed for relaxation and entertaining, the outdoor oasis includes a sparkling pool, spa, covered lounging areas, multiple decks including a rooftop deck ideal for sunrise coffee or sunset cocktails. The fenced yard provides privacy while maintaining a breezy, coastal feel. Situated in the heart of Holmes Beach, this home offers walkable access to sugar-sand beaches, local dining, boutiques, and the island’s free trolley. Enjoy the perfect blend of tranquility and convenience in one of Florida’s most desirable beach communities. This unique property can be utilized as primary residence, second home, or high-performing vacation rental investment property. This property delivers luxury, comfort, and strong rental appeal in a premier island location.

4 Beds ⋅ 5 Baths ⋅ Sportsmans Harbor SubDv. ⋅ 34217 Zip Code

Experience elevated coastal living in this brand-new, designer-finished 4BR/4.5BA luxury home located just a 5-minute walk to the pristine beaches of Anna Maria Island. Thoughtfully crafted with high-end finishes and a bright, open-concept layout, this residence blends modern elegance with relaxed island charm. Currently utilized as a successful short term vacation rental with proven rental revenue. 4 spacious ensuite bedrooms, including three king suites with walk-in showers Gorgeous open living area with abundant natural light and upscale coastal décor Chef’s kitchen featuring modern cabinetry, stone counters, and stainless appliances Private heated pool with in-ground spa, surrounded by lush tropical landscaping Expansive rooftop deck offering panoramic views and unforgettable sunsets Fully furnished with professionally curated interiors Designed for relaxation and entertaining, the outdoor oasis includes a sparkling pool, spa, covered lounging areas, multiple decks including a rooftop deck ideal for sunrise coffee or sunset cocktails. The fenced yard provides privacy while maintaining a breezy, coastal feel. Situated in the heart of Holmes Beach, this home offers walkable access to sugar-sand beaches, local dining, boutiques, and the island’s free trolley. Enjoy the perfect blend of tranquility and convenience in one of Florida’s most desirable beach communities. This unique property can be utilized as primary residence, second home, or high-performing vacation rental investment property. This property delivers luxury, comfort, and strong rental appeal in a premier island location.

227 S Harbor Drive, Holmes Beach

$1,075,000

Virtually Staged. This 3 bed/2 bath coastal charmer is just steps to the sugar sand beach, with a heated, salt water pool with full spa features! Create your own style in this cute cottage, where the hard work has already been done for you! New Luxury Vinyl Plank throughout, fresh paint, new doors, new bathrooms, new cabinetry and new appliances, means nothing left for you to do but add your personal styling! Bring your coastal creativity and create the perfect décor for you! You will love the ease of relaxing in your open family room and cooking in your updated kitchen with breakfast bar! With 3 bedrooms and a split floor plan, you have room for guests while enjoying the privacy of your own en suite. Make this your full time island escape or enjoy the benefit of income from the short term rentals that are allowed on this quiet street just steps to the soft sand of the Gulf beach! Bring your decorator spirit and make your island dream a reality by making this one your own!

3 Beds ⋅ 2 Baths ⋅ Neptunes Gardens SubDv. ⋅ 34217 Zip Code

Virtually Staged. This 3 bed/2 bath coastal charmer is just steps to the sugar sand beach, with a heated, salt water pool with full spa features! Create your own style in this cute cottage, where the hard work has already been done for you! New Luxury Vinyl Plank throughout, fresh paint, new doors, new bathrooms, new cabinetry and new appliances, means nothing left for you to do but add your personal styling! Bring your coastal creativity and create the perfect décor for you! You will love the ease of relaxing in your open family room and cooking in your updated kitchen with breakfast bar! With 3 bedrooms and a split floor plan, you have room for guests while enjoying the privacy of your own en suite. Make this your full time island escape or enjoy the benefit of income from the short term rentals that are allowed on this quiet street just steps to the soft sand of the Gulf beach! Bring your decorator spirit and make your island dream a reality by making this one your own!

5803 De Palmas Avenue, Holmes Beach

$769,000

Experience the perfect blend of luxury beachfront living and strong investment potential with this rare Gulf-front condo-hotel residence on Anna Maria Island, designed in the timeless style of a charming New England coastal inn. This intimate 12-unit boutique community offers direct access to the sandy beaches of the Gulf of Mexico and delivers one of the most desirable beachfront locations in Florida. Unit #6 is ideally positioned on the second floor and accessed by both an elegant staircase and elevator, offering convenience along with privacy and elevation for enhanced views. This spacious 2-bedroom, 2.5-bath beachfront condo features beautiful original hardwood flooring, crown molding, and a bright open layout designed for coastal comfort. A rare highlight of the residence is its two private balconies, one extending from the living room and the other from the primary suite, providing panoramic Gulf views, pool views, and unforgettable sunset skies—perfect for morning coffee, evening relaxation, or listening to waves rolling onto the shore. The interior is thoughtfully appointed with built-in closets, in-unit washer and dryer, and a fully turnkey package that includes furnishings, décor, beach equipment, kayaks, and paddleboards, allowing for immediate enjoyment without additional setup. As part of a professionally managed condo-hotel investment property, owners benefit from up to 120 days of personal use a year while the on-site management team handles rentals the remainder of the time. With its prime beachfront location on Anna Maria Island, the property consistently achieves strong occupancy rates, making it an attractive income-producing vacation rental investment. Even better, ownership allows you to enjoy months of personal beachfront living annually while rental income helps offset operating costs, creating both lifestyle value and financial efficiency. Offered fully turnkey, this residence checks every box for buyers seeking a luxury beachfront condo on Anna Maria Island, a Gulf-front vacation rental investment property, or a low-maintenance coastal retreat in Florida. Simply bring your swimsuit and start enjoying beachfront living at its finest—where lifestyle, location, and long-term value all come together in one exceptional opportunity.

2 Beds ⋅ 3 Baths ⋅ Anna Maria Island Club SubDv. ⋅ 34217 Zip Code

Experience the perfect blend of luxury beachfront living and strong investment potential with this rare Gulf-front condo-hotel residence on Anna Maria Island, designed in the timeless style of a charming New England coastal inn. This intimate 12-unit boutique community offers direct access to the sandy beaches of the Gulf of Mexico and delivers one of the most desirable beachfront locations in Florida. Unit #6 is ideally positioned on the second floor and accessed by both an elegant staircase and elevator, offering convenience along with privacy and elevation for enhanced views. This spacious 2-bedroom, 2.5-bath beachfront condo features beautiful original hardwood flooring, crown molding, and a bright open layout designed for coastal comfort. A rare highlight of the residence is its two private balconies, one extending from the living room and the other from the primary suite, providing panoramic Gulf views, pool views, and unforgettable sunset skies—perfect for morning coffee, evening relaxation, or listening to waves rolling onto the shore. The interior is thoughtfully appointed with built-in closets, in-unit washer and dryer, and a fully turnkey package that includes furnishings, décor, beach equipment, kayaks, and paddleboards, allowing for immediate enjoyment without additional setup. As part of a professionally managed condo-hotel investment property, owners benefit from up to 120 days of personal use a year while the on-site management team handles rentals the remainder of the time. With its prime beachfront location on Anna Maria Island, the property consistently achieves strong occupancy rates, making it an attractive income-producing vacation rental investment. Even better, ownership allows you to enjoy months of personal beachfront living annually while rental income helps offset operating costs, creating both lifestyle value and financial efficiency. Offered fully turnkey, this residence checks every box for buyers seeking a luxury beachfront condo on Anna Maria Island, a Gulf-front vacation rental investment property, or a low-maintenance coastal retreat in Florida. Simply bring your swimsuit and start enjoying beachfront living at its finest—where lifestyle, location, and long-term value all come together in one exceptional opportunity.

101 66th Street Unit 6, Holmes Beach

$699,000

One-of-a-kind Holmes Beach retreat just minutes from the sand! This completely renovated 1-bedroom, 1-bath home offers everything you need in the perfect beach getaway or income-producing property. Thoughtfully updated throughout, the home features hurricane-impact windows and doors, solid wood cabinetry, stainless steel appliances, tile flooring, and granite countertops. Offered turnkey furnished with a stylish coastal décor, it’s truly move-in or rental ready.Step outside to your private outdoor oasis featuring a large heated free-form pool, spacious patio ideal for entertaining, custom outdoor lighting, and an outdoor shower with rain head—perfect after a day at the beach. Located just two blocks from popular shops and restaurants and only a five-minute walk to the Gulf beaches, this prime island location delivers the best of Anna Maria Island living.Whether you’re seeking a personal island retreat or a strong investment opportunity, this property shines with projected rental income up to $50,000 annually. Don’t miss this rare chance to own a turnkey beach home in the heart of Holmes Beach.

1 Beds ⋅ 1 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code

One-of-a-kind Holmes Beach retreat just minutes from the sand! This completely renovated 1-bedroom, 1-bath home offers everything you need in the perfect beach getaway or income-producing property. Thoughtfully updated throughout, the home features hurricane-impact windows and doors, solid wood cabinetry, stainless steel appliances, tile flooring, and granite countertops. Offered turnkey furnished with a stylish coastal décor, it’s truly move-in or rental ready.Step outside to your private outdoor oasis featuring a large heated free-form pool, spacious patio ideal for entertaining, custom outdoor lighting, and an outdoor shower with rain head—perfect after a day at the beach. Located just two blocks from popular shops and restaurants and only a five-minute walk to the Gulf beaches, this prime island location delivers the best of Anna Maria Island living.Whether you’re seeking a personal island retreat or a strong investment opportunity, this property shines with projected rental income up to $50,000 annually. Don’t miss this rare chance to own a turnkey beach home in the heart of Holmes Beach.

205 Peacock Lane Unit A, Holmes Beach

$5,595,000

Discover the epitome of coastal sophistication with this exquisite British West Indies waterfront residence, perfectly nestled on Anna Maria Island. Spanning over 5,000 square feet, this luxurious home is designed for those who love to entertain and indulge in the finer things in life. Step inside to find two lavish primary suites, an elevator, and multiple terraces that offer breathtaking views. The entertainment options are endless with a stylish media room featuring a beverage center, ideal for movie nights or hosting friends. Every corner of this home exudes elegance, from the solid wood cabinetry and custom millwork to the stunning hardwood and travertine flooring. The open floor plan seamlessly connects to an eat-in kitchen, boasting a large central island, double oven, butler’s pantry, and granite surfaces, making it a chef’s paradise. For more formal gatherings, the separate dining room sets the perfect scene. An office or den is conveniently located on the main level, offering a quiet retreat for work or relaxation. Two additional bedrooms share a spacious bathroom complete with a walk-in shower, ensuring comfort for family or guests. Outdoors, the multiple living areas provide serene views of the canal and Bimini Bay, with direct access to the Intracoastal waterway. The lavish outdoor amenities include a saltwater pool with a sun shelf and spa, and a 70-foot dock equipped with a 13,000-pound boat lift, perfect for boating enthusiasts. Entertain in style on the expansive covered lanai, featuring an outdoor kitchen and ample space for gatherings. Additional features such as plantation shutters, a state-of-the-art security system, oversized closets, and a 3-plus car garage enhance the allure of this property. Don’t miss your chance to own this stunning waterfront retreat. Call today for your private viewing and step into a lifestyle of unparalleled luxury.

5 Beds ⋅ 5 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code

Discover the epitome of coastal sophistication with this exquisite British West Indies waterfront residence, perfectly nestled on Anna Maria Island. Spanning over 5,000 square feet, this luxurious home is designed for those who love to entertain and indulge in the finer things in life. Step inside to find two lavish primary suites, an elevator, and multiple terraces that offer breathtaking views. The entertainment options are endless with a stylish media room featuring a beverage center, ideal for movie nights or hosting friends. Every corner of this home exudes elegance, from the solid wood cabinetry and custom millwork to the stunning hardwood and travertine flooring. The open floor plan seamlessly connects to an eat-in kitchen, boasting a large central island, double oven, butler’s pantry, and granite surfaces, making it a chef’s paradise. For more formal gatherings, the separate dining room sets the perfect scene. An office or den is conveniently located on the main level, offering a quiet retreat for work or relaxation. Two additional bedrooms share a spacious bathroom complete with a walk-in shower, ensuring comfort for family or guests. Outdoors, the multiple living areas provide serene views of the canal and Bimini Bay, with direct access to the Intracoastal waterway. The lavish outdoor amenities include a saltwater pool with a sun shelf and spa, and a 70-foot dock equipped with a 13,000-pound boat lift, perfect for boating enthusiasts. Entertain in style on the expansive covered lanai, featuring an outdoor kitchen and ample space for gatherings. Additional features such as plantation shutters, a state-of-the-art security system, oversized closets, and a 3-plus car garage enhance the allure of this property. Don’t miss your chance to own this stunning waterfront retreat. Call today for your private viewing and step into a lifestyle of unparalleled luxury.

529 77th Street, Holmes Beach

$625,000

**NO HOA** Find me another turnkey island property like this one that is zoned for short term rentals without an HOA... Elevated and fully updated coastal retreat on beautiful Anna Maria Island with NO HOA! Built for peace of mind with a newer metal roof, newer deck, HVAC system with brand new UV light and air scrubber, impact windows and doors with a lifetime warranty. The property has been meticulously maintained with a transferrable termite warranty, updated landscaping, outdoor shower, and covered parking for up to five vehicles. Offered fully furnished and ready for you to enjoy the option of flexible income potential with the ability to short term rent while owning a slice of island life near the Gulf beaches, dining, and laid-back charm of Holmes Beach.

2 Beds ⋅ 2 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code

**NO HOA** Find me another turnkey island property like this one that is zoned for short term rentals without an HOA... Elevated and fully updated coastal retreat on beautiful Anna Maria Island with NO HOA! Built for peace of mind with a newer metal roof, newer deck, HVAC system with brand new UV light and air scrubber, impact windows and doors with a lifetime warranty. The property has been meticulously maintained with a transferrable termite warranty, updated landscaping, outdoor shower, and covered parking for up to five vehicles. Offered fully furnished and ready for you to enjoy the option of flexible income potential with the ability to short term rent while owning a slice of island life near the Gulf beaches, dining, and laid-back charm of Holmes Beach.

4909 Gulf Drive Unit 6B, Holmes Beach

$3,300,000

Nestled along a serene canal and embraced by a curtain of mature tropical palms, this custom-remodeled residence unfolds as a private coastal estate, an intimate sanctuary where luxury, tranquility, and effortless island living exist in perfect harmony. Masterfully re-imagined by Eason Builder Group, the home was completely gutted and rebuilt just four years ago, and last year the entire first level was once again fully renovated, resulting in a residence that feels both newly crafted and timelessly refined. From the moment you arrive, a sense of seclusion and calm sets in. As you walk up to the home, an old-growth Gumbo Limbo greets you. Sunlight filters through new hurricane-impact windows, illuminating interiors designed to feel open yet intimate, grand yet soothing. The main living space becomes a natural gathering place, anchored by a custom-built-in entertainment center and a coffee station. An elegant touch that invites slow mornings, refined evenings, and effortless entertaining. Sonos surround sound flows throughout the home, creating an ambient soundtrack for daily life, while a fully integrated security and camera system offers peace of mind and quiet confidence. Complementing the home's HURRICANE-IMPACT WINDOWS, professionally INSTALLED FLOOD PANELS provide an additional safeguard, reflecting the thoughtful attention to both luxury and long-term resilience found throughout the property. The kitchen stands as a statement of both beauty and performance, where quartz countertops, solid-wood glass-front cabinetry, a sculptural range hood, designer pendant lighting, and stainless-steel Bosch appliances come together in a space crafted for culinary artistry and connection. It opens seamlessly to the dining area, where a wood-burning travertine stone fireplace adds warmth and architectural presence, setting the stage for candlelit dinners and lingering conversations. Two luxurious primary suites, one on each level offers the rare indulgence of privacy and flexibility. Each is finished with shiplap walls, porcelain tile, recessed lighting, and abundant natural light. The upper-level retreat opens to a private balcony overlooking the pool and tropical grounds, a serene perch for sunrise reflections and evening breezes. Its spa-inspired ensuite features a quartz walk-in shower, while the first-floor primary bath is appointed with a solid-wood double vanity, continuing the home’s narrative of tailored craftsmanship and understated elegance. Completing the residence are two additional bedrooms with a shared bath and an upstairs bonus room ideal for recreation, fitness, or creative pursuits. Beyond the interiors, the estate reveals its most captivating chapter. The backyard unfolds as a secluded resort, where a glistening pool and spa are framed by layered, well-established tropical landscaping that has matured into a living wall of privacy. Covered and open-air lounges invite both sun-drenched afternoons and starlit evenings, while a turf-lined grilling and gathering area provides an elevated setting for alfresco dining. Just beyond the palms, the canal stretches quietly behind the property, creating the illusion that the waterway is an extension of your own grounds and inviting a lifestyle of boating, paddleboarding, and sunset cruises from your private dock. When you venture beyond this sanctuary, the unmistakable charm of Holmes Beach awaits.

4 Beds ⋅ 6 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code

Nestled along a serene canal and embraced by a curtain of mature tropical palms, this custom-remodeled residence unfolds as a private coastal estate, an intimate sanctuary where luxury, tranquility, and effortless island living exist in perfect harmony. Masterfully re-imagined by Eason Builder Group, the home was completely gutted and rebuilt just four years ago, and last year the entire first level was once again fully renovated, resulting in a residence that feels both newly crafted and timelessly refined. From the moment you arrive, a sense of seclusion and calm sets in. As you walk up to the home, an old-growth Gumbo Limbo greets you. Sunlight filters through new hurricane-impact windows, illuminating interiors designed to feel open yet intimate, grand yet soothing. The main living space becomes a natural gathering place, anchored by a custom-built-in entertainment center and a coffee station. An elegant touch that invites slow mornings, refined evenings, and effortless entertaining. Sonos surround sound flows throughout the home, creating an ambient soundtrack for daily life, while a fully integrated security and camera system offers peace of mind and quiet confidence. Complementing the home's HURRICANE-IMPACT WINDOWS, professionally INSTALLED FLOOD PANELS provide an additional safeguard, reflecting the thoughtful attention to both luxury and long-term resilience found throughout the property. The kitchen stands as a statement of both beauty and performance, where quartz countertops, solid-wood glass-front cabinetry, a sculptural range hood, designer pendant lighting, and stainless-steel Bosch appliances come together in a space crafted for culinary artistry and connection. It opens seamlessly to the dining area, where a wood-burning travertine stone fireplace adds warmth and architectural presence, setting the stage for candlelit dinners and lingering conversations. Two luxurious primary suites, one on each level offers the rare indulgence of privacy and flexibility. Each is finished with shiplap walls, porcelain tile, recessed lighting, and abundant natural light. The upper-level retreat opens to a private balcony overlooking the pool and tropical grounds, a serene perch for sunrise reflections and evening breezes. Its spa-inspired ensuite features a quartz walk-in shower, while the first-floor primary bath is appointed with a solid-wood double vanity, continuing the home’s narrative of tailored craftsmanship and understated elegance. Completing the residence are two additional bedrooms with a shared bath and an upstairs bonus room ideal for recreation, fitness, or creative pursuits. Beyond the interiors, the estate reveals its most captivating chapter. The backyard unfolds as a secluded resort, where a glistening pool and spa are framed by layered, well-established tropical landscaping that has matured into a living wall of privacy. Covered and open-air lounges invite both sun-drenched afternoons and starlit evenings, while a turf-lined grilling and gathering area provides an elevated setting for alfresco dining. Just beyond the palms, the canal stretches quietly behind the property, creating the illusion that the waterway is an extension of your own grounds and inviting a lifestyle of boating, paddleboarding, and sunset cruises from your private dock. When you venture beyond this sanctuary, the unmistakable charm of Holmes Beach awaits.

506 58th Street, Holmes Beach

$749,900

Set within the beachfront enclave of Playa Encantada, this beautifully maintained two-bedroom, two-bath residence offers an effortless coastal lifestyle just steps from the sand and the island trolley — placing the area's finest shops, restaurants, and attractions within easy reach. Inside, an open and light-filled layout creates an inviting sense of space. The kitchen is appointed with granite countertops, stainless steel appliances, and generous cabinetry, while the living and dining areas flow seamlessly onto a private balcony overlooking the heated pool — an ideal setting to take in the Gulf breezes and glimpses of the water beyond. Both bedrooms are generously sized, with the primary suite featuring a private en-suite bath. Residents enjoy a thoughtful collection of resort-style amenities, including a heated pool, tennis courts, shuffleboard, and private beach access. A flexible two-week minimum rental policy further enhances its appeal, offering an exceptional opportunity as a seasonal retreat or income-producing investment.

2 Beds ⋅ 2 Baths ⋅ Playa Encantada Condominium SubDv. ⋅ 34217 Zip Code

Set within the beachfront enclave of Playa Encantada, this beautifully maintained two-bedroom, two-bath residence offers an effortless coastal lifestyle just steps from the sand and the island trolley — placing the area's finest shops, restaurants, and attractions within easy reach. Inside, an open and light-filled layout creates an inviting sense of space. The kitchen is appointed with granite countertops, stainless steel appliances, and generous cabinetry, while the living and dining areas flow seamlessly onto a private balcony overlooking the heated pool — an ideal setting to take in the Gulf breezes and glimpses of the water beyond. Both bedrooms are generously sized, with the primary suite featuring a private en-suite bath. Residents enjoy a thoughtful collection of resort-style amenities, including a heated pool, tennis courts, shuffleboard, and private beach access. A flexible two-week minimum rental policy further enhances its appeal, offering an exceptional opportunity as a seasonal retreat or income-producing investment.

6006 Gulf Drive Unit 214, Holmes Beach

$1,399,000

OVER 150K INCOME OVER LAST 12 MONTHS!!! Embrace the pinnacle of island luxury with this impeccably designed, turnkey Holmes Beach duplex—operating as a successful Airbnb and ready for seamless ownership transition. Each side features two spacious bedrooms and one bath, complete with gleaming marble countertops, white shaker cabinetry, elegant, natural-flow tile backsplashes and breathtaking remodeled bathrooms. With fresh paint, brand-new flooring, and a 2022 roof, the home is both stunning and secure. Every door and window is hurricane-rated and newly installed—offering peace of mind in every detail. Outdoors, one side boasts a heated pool with newly installed heater and a gorgeous waterfall feature, while the other side offers a soothing hot tub just installed in 2025 as well. Two outdoor showers add to the coastal experience, surrounded by lush, meticulously maintained landscaping. With five parking spots and separate entrances, you can host larger groups as a whole or individual parties in each unit and your guests will fall in love with this location when they find out public beach access is less than a block away! This duplex is uniquely positioned for maximum rental flexibility. Weekly rentals are fully allowed, making this a prime investment. High-end furnishings down to the last detail—silverware, plates, bedding, towels—ensure a seamless guest experience. Just steps from the vibrant charm of historic Bridge Street—known for its waterfront dining, boutique shops, and lively atmosphere—and minutes from the serene Bean Point, this property is at the heart of one of Florida’s top destinations. This is more than a home; it’s a fully operational, luxurious escape. Whether you’re continuing its rental success or claiming it for yourself, this is an unparalleled opportunity for coastal living and investment combined.

4 Beds ⋅ 2 Baths ⋅ Casanas Sub SubDv. ⋅ 34217 Zip Code

OVER 150K INCOME OVER LAST 12 MONTHS!!! Embrace the pinnacle of island luxury with this impeccably designed, turnkey Holmes Beach duplex—operating as a successful Airbnb and ready for seamless ownership transition. Each side features two spacious bedrooms and one bath, complete with gleaming marble countertops, white shaker cabinetry, elegant, natural-flow tile backsplashes and breathtaking remodeled bathrooms. With fresh paint, brand-new flooring, and a 2022 roof, the home is both stunning and secure. Every door and window is hurricane-rated and newly installed—offering peace of mind in every detail. Outdoors, one side boasts a heated pool with newly installed heater and a gorgeous waterfall feature, while the other side offers a soothing hot tub just installed in 2025 as well. Two outdoor showers add to the coastal experience, surrounded by lush, meticulously maintained landscaping. With five parking spots and separate entrances, you can host larger groups as a whole or individual parties in each unit and your guests will fall in love with this location when they find out public beach access is less than a block away! This duplex is uniquely positioned for maximum rental flexibility. Weekly rentals are fully allowed, making this a prime investment. High-end furnishings down to the last detail—silverware, plates, bedding, towels—ensure a seamless guest experience. Just steps from the vibrant charm of historic Bridge Street—known for its waterfront dining, boutique shops, and lively atmosphere—and minutes from the serene Bean Point, this property is at the heart of one of Florida’s top destinations. This is more than a home; it’s a fully operational, luxurious escape. Whether you’re continuing its rental success or claiming it for yourself, this is an unparalleled opportunity for coastal living and investment combined.

3604 Gulf Drive Unit A and B, Holmes Beach

$2,399,000

Welcome to Sands of Time, a recently updated six-bedroom, four-and-a-half-bathroom coastal retreat located less than two blocks from the white-sand beaches in the heart of Holmes Beach on Anna Maria Island. Thoughtfully designed and professionally decorated, this home blends relaxed beach style with upscale comfort, making it ideal as a primary residence, second home, or high-performing investment property. Inside, the spacious layout comfortably accommodates family and guests, with multiple living areas and a fully equipped kitchen designed for entertaining and everyday living alike. High-capacity laundry is conveniently located on the main floor, perfect after long days at the beach. Four private balconies invite you to enjoy morning coffee or evening breezes, while the home’s open flow creates a welcoming atmosphere throughout. The outdoor living space is a true highlight. A private heated pool and spa with a waterslide anchor a beautifully updated backyard featuring a bar with seating, lounge chairs, a large outdoor dining area, an outdoor shower, and a stainless-steel grill. A covered lanai beside the pool offers ample seating and an outdoor television, making it an ideal gathering place day or night. As evening falls, the backyard transforms into a tropical oasis with illuminated palms and ambient lighting. Entertainment continues indoors and in the oversized garage, which has been converted into a game space complete with a ping pong table, foosball table, and arcade game. When it’s time to unwind, the home offers six well-appointed bedrooms, each with a flat-screen television. Four bedrooms feature king beds, including three with en suite bathrooms and private balconies. One bedroom includes two twin beds, while another offers two sets of bunk beds, creating a perfect space for kids or guests. A half bath is located on the main floor, with an additional full bathroom upstairs. Situated on a quiet stretch of Holmes Boulevard, the property offers both privacy and convenience. Shops, restaurants, and island favorites along Pine Avenue are just minutes away, and the free island trolley stops nearby, providing easy access to all seven miles of Anna Maria Island. From boutique shopping and dining to fishing, boating, kayaking through mangroves, dolphin tours, and unforgettable sunsets, everything the island is known for is within easy reach. Sands of Time delivers the best of island living with space, style, and an unbeatable location in the heart of Holmes Beach. Schedule your private showing today!

6 Beds ⋅ 6 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code

Welcome to Sands of Time, a recently updated six-bedroom, four-and-a-half-bathroom coastal retreat located less than two blocks from the white-sand beaches in the heart of Holmes Beach on Anna Maria Island. Thoughtfully designed and professionally decorated, this home blends relaxed beach style with upscale comfort, making it ideal as a primary residence, second home, or high-performing investment property. Inside, the spacious layout comfortably accommodates family and guests, with multiple living areas and a fully equipped kitchen designed for entertaining and everyday living alike. High-capacity laundry is conveniently located on the main floor, perfect after long days at the beach. Four private balconies invite you to enjoy morning coffee or evening breezes, while the home’s open flow creates a welcoming atmosphere throughout. The outdoor living space is a true highlight. A private heated pool and spa with a waterslide anchor a beautifully updated backyard featuring a bar with seating, lounge chairs, a large outdoor dining area, an outdoor shower, and a stainless-steel grill. A covered lanai beside the pool offers ample seating and an outdoor television, making it an ideal gathering place day or night. As evening falls, the backyard transforms into a tropical oasis with illuminated palms and ambient lighting. Entertainment continues indoors and in the oversized garage, which has been converted into a game space complete with a ping pong table, foosball table, and arcade game. When it’s time to unwind, the home offers six well-appointed bedrooms, each with a flat-screen television. Four bedrooms feature king beds, including three with en suite bathrooms and private balconies. One bedroom includes two twin beds, while another offers two sets of bunk beds, creating a perfect space for kids or guests. A half bath is located on the main floor, with an additional full bathroom upstairs. Situated on a quiet stretch of Holmes Boulevard, the property offers both privacy and convenience. Shops, restaurants, and island favorites along Pine Avenue are just minutes away, and the free island trolley stops nearby, providing easy access to all seven miles of Anna Maria Island. From boutique shopping and dining to fishing, boating, kayaking through mangroves, dolphin tours, and unforgettable sunsets, everything the island is known for is within easy reach. Sands of Time delivers the best of island living with space, style, and an unbeatable location in the heart of Holmes Beach. Schedule your private showing today!

6908 Holmes Boulevard, Holmes Beach

$2,995,000

A rare waterfront opportunity just became irresistible!!! Luxury 5 Bedroom Waterfront + Dock | 3-Min Walk to Beach -Exceptional waterfront retreat perfectly positioned in the heart of Anna Maria Island. Just a three-minute stroll to the soft sugar sands of Manatee Beach, this stunning five-bedroom, three-and-a-half-bath residence delivers coastal luxury at every turn—complete with a private dock with ladder where manatees often glide by, a heated pool and spa, and a show-stopping rooftop deck with Gulf and Bay views. Designed for unforgettable gatherings, Coral Castle seamlessly blends upscale comfort with relaxed island charm! Outdoor Living at Its Finest, the rooftop deck is the crown jewel of Coral Castle—offering breathtaking sunrise and sunset views over both the Gulf and Bay. Start your mornings with coffee and ocean breezes or unwind in the evening with a cocktail as the sky glows in brilliant island hues. The tropical backyard is a private sanctuary featuring a heated pool, spa, lounge seating, and outdoor grill, perfect for post-beach relaxation or entertaining under the stars. From the private dock, enjoy peaceful water views—and keep watch for friendly manatees passing by, an unforgettable hallmark of island living. Stylish Interiors Made for Comfort-Step inside to a bright, open-concept living space filled with natural light and coastal elegance. The living room offers plush seating, a flat-screen TV, and sliding glass doors that open directly to the outdoor patio—blurring the line between indoor and outdoor living. The chef-inspired kitchen is fully equipped with stainless steel appliances, generous counter space, and a wine fridge, making meal prep effortless. Gather inside at the dining table or dine alfresco beneath the covered patio for a true island experience. Sleep in Luxury- Primary Suite: King bed, private balcony, vaulted shiplap ceiling, walk-in closet, spa-style ensuite with soaking tub and walk-in shower; Second Bedroom: King bed, Jack-and-Jill bathroom with walk-in shower; Third Bedroom: King bed, Jack-and-Jill bathroom with walk-in shower; Fourth Bedroom: Full bed, Jack-and-Jill bathroom with shower/tub combo; and Fifth Bedroom: Full bed, Jack-and-Jill bathroom with shower/tub combo. Prime Island Location- Enjoy peaceful mornings fishing from the dock or take a short drive to Pine Avenue and Bridge Street, where you’ll discover charming boutiques, local dining, and island favorites. Whether your days are spent boating, lounging by the pool, or soaking in rooftop views, Coral Castle delivers the perfect balance of relaxation and adventure. Every detail is designed to create lasting memories—from manatee sightings to sunset cocktails on the rooftop. This is more than a stay—it’s a true Anna Maria Island experience. Currently operating as a vacation rental with solid history and a strong start to 2026—ideal personal-use + income opportunity.

5 Beds ⋅ 4 Baths ⋅ Sportsmans Harbor SubDv. ⋅ 34217 Zip Code

A rare waterfront opportunity just became irresistible!!! Luxury 5 Bedroom Waterfront + Dock | 3-Min Walk to Beach -Exceptional waterfront retreat perfectly positioned in the heart of Anna Maria Island. Just a three-minute stroll to the soft sugar sands of Manatee Beach, this stunning five-bedroom, three-and-a-half-bath residence delivers coastal luxury at every turn—complete with a private dock with ladder where manatees often glide by, a heated pool and spa, and a show-stopping rooftop deck with Gulf and Bay views. Designed for unforgettable gatherings, Coral Castle seamlessly blends upscale comfort with relaxed island charm! Outdoor Living at Its Finest, the rooftop deck is the crown jewel of Coral Castle—offering breathtaking sunrise and sunset views over both the Gulf and Bay. Start your mornings with coffee and ocean breezes or unwind in the evening with a cocktail as the sky glows in brilliant island hues. The tropical backyard is a private sanctuary featuring a heated pool, spa, lounge seating, and outdoor grill, perfect for post-beach relaxation or entertaining under the stars. From the private dock, enjoy peaceful water views—and keep watch for friendly manatees passing by, an unforgettable hallmark of island living. Stylish Interiors Made for Comfort-Step inside to a bright, open-concept living space filled with natural light and coastal elegance. The living room offers plush seating, a flat-screen TV, and sliding glass doors that open directly to the outdoor patio—blurring the line between indoor and outdoor living. The chef-inspired kitchen is fully equipped with stainless steel appliances, generous counter space, and a wine fridge, making meal prep effortless. Gather inside at the dining table or dine alfresco beneath the covered patio for a true island experience. Sleep in Luxury- Primary Suite: King bed, private balcony, vaulted shiplap ceiling, walk-in closet, spa-style ensuite with soaking tub and walk-in shower; Second Bedroom: King bed, Jack-and-Jill bathroom with walk-in shower; Third Bedroom: King bed, Jack-and-Jill bathroom with walk-in shower; Fourth Bedroom: Full bed, Jack-and-Jill bathroom with shower/tub combo; and Fifth Bedroom: Full bed, Jack-and-Jill bathroom with shower/tub combo. Prime Island Location- Enjoy peaceful mornings fishing from the dock or take a short drive to Pine Avenue and Bridge Street, where you’ll discover charming boutiques, local dining, and island favorites. Whether your days are spent boating, lounging by the pool, or soaking in rooftop views, Coral Castle delivers the perfect balance of relaxation and adventure. Every detail is designed to create lasting memories—from manatee sightings to sunset cocktails on the rooftop. This is more than a stay—it’s a true Anna Maria Island experience. Currently operating as a vacation rental with solid history and a strong start to 2026—ideal personal-use + income opportunity.

203 N Harbor Drive, Holmes Beach

$1,100,000

Welcome to "Captains Quarters" this luxury duplex is recently renovated and centrally located on Anna Maria Island with over $140k in projected rental revenue for 2026. This property underwent a full renovation in 2023 with full permits for new windows, electric, ac, and plumbing. This island retreat features a brand new heated saltwater pool and spa nestled among the palm trees with a secluded beach alley access. Each side features it's own kitchen, living and dining area. The gourmet kitchen in both units features quartz countertops, new shaker cabinets and stainless steel appliances. This home is being sold turn-key furnished. Property is currently being used as a vacation rental. Call today for your private showing!

2 Beds ⋅ 2 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code

Welcome to "Captains Quarters" this luxury duplex is recently renovated and centrally located on Anna Maria Island with over $140k in projected rental revenue for 2026. This property underwent a full renovation in 2023 with full permits for new windows, electric, ac, and plumbing. This island retreat features a brand new heated saltwater pool and spa nestled among the palm trees with a secluded beach alley access. Each side features it's own kitchen, living and dining area. The gourmet kitchen in both units features quartz countertops, new shaker cabinets and stainless steel appliances. This home is being sold turn-key furnished. Property is currently being used as a vacation rental. Call today for your private showing!

3016 Gulf Drive, Holmes Beach

$1,125,000

Welcome to "Pineapple Paradise" this luxury duplex is recently renovated and centrally located on Anna Maria Island with over $140k in rental revenue projected for 2026. This property underwent a full renovation in 2023 with full permits for new windows, electric, ac, and plumbing. This island retreat features a brand new heated saltwater pool and spa nestled among the palm trees with a secluded beach alley access. Each side features it's own kitchen, living and dining area. The gourmet kitchen in both units features quartz countertops, new shaker cabinets and stainless steel appliances. This home is being sold turn-key furnished. Property is currently being used as a vacation rental. Call today for your private showing!

2 Beds ⋅ 2 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code

Welcome to "Pineapple Paradise" this luxury duplex is recently renovated and centrally located on Anna Maria Island with over $140k in rental revenue projected for 2026. This property underwent a full renovation in 2023 with full permits for new windows, electric, ac, and plumbing. This island retreat features a brand new heated saltwater pool and spa nestled among the palm trees with a secluded beach alley access. Each side features it's own kitchen, living and dining area. The gourmet kitchen in both units features quartz countertops, new shaker cabinets and stainless steel appliances. This home is being sold turn-key furnished. Property is currently being used as a vacation rental. Call today for your private showing!

3014 Gulf Drive, Holmes Beach

$659,000

GULF FRONT - Spacious and Beautifully Maintained and Renovated 1 Bedroom/1 Bath Condo in the Heart of Holmes Beach. Breathtaking Gulf Views to behold from every room. The kitchen, windows and sliding doors have been updated and the AC was replaced in 2025. This unit features a covered, open balcony allowing for your own Private Outdoor Space while relishing in the balmy Gulf breezes. Commodious Open living/dining area is painted in calm, neutral colors and ceramic tile flows throughout. The bedroom features full gulf views, a large walk-in closet and ensuite bath with separate vanity area and combination tub/shower. The updated kitchen provides plentiful and aesthetic cabinetry, a closet pantry, newer appliances, desk area and Washer and Dryer. Martinique South offers a Gulf side pool, tennis/pickle ball courts, an elevator, secure entrance, large Community living space with full Gulf Views, a complete kitchen, bathrooms, and outdoor covered patio. The Community Room is ideal for parties and large gatherings. Pride of ownership shines in this community where friends are neighbors and neighbors are friends. This lovely unit is offered turn-key furnished, with room for your personal touches as well as a carport and storage room. Located within walking distance of Holmes Beach amenities. Magnificent sunsets, strolls along the white sand beach, passing dolphins, the cry of the seabirds and the comforting sound of the surf await...

1 Beds ⋅ 1 Baths ⋅ Martinique Condo SubDv. ⋅ 34217 Zip Code

GULF FRONT - Spacious and Beautifully Maintained and Renovated 1 Bedroom/1 Bath Condo in the Heart of Holmes Beach. Breathtaking Gulf Views to behold from every room. The kitchen, windows and sliding doors have been updated and the AC was replaced in 2025. This unit features a covered, open balcony allowing for your own Private Outdoor Space while relishing in the balmy Gulf breezes. Commodious Open living/dining area is painted in calm, neutral colors and ceramic tile flows throughout. The bedroom features full gulf views, a large walk-in closet and ensuite bath with separate vanity area and combination tub/shower. The updated kitchen provides plentiful and aesthetic cabinetry, a closet pantry, newer appliances, desk area and Washer and Dryer. Martinique South offers a Gulf side pool, tennis/pickle ball courts, an elevator, secure entrance, large Community living space with full Gulf Views, a complete kitchen, bathrooms, and outdoor covered patio. The Community Room is ideal for parties and large gatherings. Pride of ownership shines in this community where friends are neighbors and neighbors are friends. This lovely unit is offered turn-key furnished, with room for your personal touches as well as a carport and storage room. Located within walking distance of Holmes Beach amenities. Magnificent sunsets, strolls along the white sand beach, passing dolphins, the cry of the seabirds and the comforting sound of the surf await...

5200 Gulf Drive Unit 302, Holmes Beach

$3,495,000

Striking modern luxury meets investment potential at The Black Pearl, a four-bedroom, five-and-a-half-bath residence located just a short walk from the beaches of Holmes Beach, downtown shopping and dining, and the island trolley. This architecturally distinctive black-and-white home features a private black-bottom infinity-edge pool, resort-style outdoor living, and a rooftop deck with panoramic Gulf views. Designed for both lifestyle and performance, the home offers a bright open-concept interior, gourmet kitchen with island seating, and four king bedroom suites—each with a private ensuite bath—plus a bonus den with additional sleeping flexibility. Outdoor amenities include a full outdoor kitchen, multiple lounge and dining areas, outdoor shower, and ample on-site parking. Currently part of the Exclusive Vacations luxury rental program, the property offers immediate access to a professionally managed, high-end short-term rental platform focused on premium positioning, elevated guest experience, and revenue optimization. A rare opportunity to own a visually iconic, walkable luxury home with proven short-term rental appeal on Anna Maria Island.

4 Beds ⋅ 6 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code

Striking modern luxury meets investment potential at The Black Pearl, a four-bedroom, five-and-a-half-bath residence located just a short walk from the beaches of Holmes Beach, downtown shopping and dining, and the island trolley. This architecturally distinctive black-and-white home features a private black-bottom infinity-edge pool, resort-style outdoor living, and a rooftop deck with panoramic Gulf views. Designed for both lifestyle and performance, the home offers a bright open-concept interior, gourmet kitchen with island seating, and four king bedroom suites—each with a private ensuite bath—plus a bonus den with additional sleeping flexibility. Outdoor amenities include a full outdoor kitchen, multiple lounge and dining areas, outdoor shower, and ample on-site parking. Currently part of the Exclusive Vacations luxury rental program, the property offers immediate access to a professionally managed, high-end short-term rental platform focused on premium positioning, elevated guest experience, and revenue optimization. A rare opportunity to own a visually iconic, walkable luxury home with proven short-term rental appeal on Anna Maria Island.

5612 Guava Street, Holmes Beach

$2,150,000

Discover a versatile two-unit property in Holmes Beach offering the flexibility many buyers seek on Anna Maria Island. With a combined total of 5 bedrooms and 4 bathrooms, this property includes two fully turnkey residences: Pool Party South, a 3-bedroom, 2-bath main home, and Pool Party North, a 2-bedroom, 2-bath secondary unit. This configuration is well suited for those looking for a two-unit island home, a vacation property with short-term rental potential, or a second home that can help offset expenses when not in use. Both units feature coastal-inspired updates, including modern tile flooring, granite countertops, stainless steel appliances, newer roofs, and comfortable furnishings. Offered turnkey, the property is ready for immediate enjoyment or rental use. Weekly rentals are permitted, providing owners the flexibility to enjoy the island on their own schedule while generating income when away—an important consideration for buyers seeking short-term rental options on Anna Maria Island. The outdoor living area enhances the relaxed Florida lifestyle with a heated pool and spa, outdoor bar with sink, and multiple areas for dining and lounging. The oversized lot adds a sense of privacy, creating an inviting retreat for both owners and guests. This layout appeals to a variety of uses, including a multi-residence setup, a dual-unit investment property, or a home offering separation between living space and guest accommodations while maintaining rental flexibility. Located just a short walk to the Gulf beaches, as well as nearby dining, shopping, and island amenities, this property captures the ease and charm of Holmes Beach living. For buyers searching for an updated two-unit home with a pool, walkable beach access, and strong rental potential, Pool Party South and Pool Party North provide a compelling blend of lifestyle and opportunity on Anna Maria Island.

5 Beds ⋅ 4 Baths ⋅ Holmes Beach SubDv. ⋅ 34217 Zip Code

Discover a versatile two-unit property in Holmes Beach offering the flexibility many buyers seek on Anna Maria Island. With a combined total of 5 bedrooms and 4 bathrooms, this property includes two fully turnkey residences: Pool Party South, a 3-bedroom, 2-bath main home, and Pool Party North, a 2-bedroom, 2-bath secondary unit. This configuration is well suited for those looking for a two-unit island home, a vacation property with short-term rental potential, or a second home that can help offset expenses when not in use. Both units feature coastal-inspired updates, including modern tile flooring, granite countertops, stainless steel appliances, newer roofs, and comfortable furnishings. Offered turnkey, the property is ready for immediate enjoyment or rental use. Weekly rentals are permitted, providing owners the flexibility to enjoy the island on their own schedule while generating income when away—an important consideration for buyers seeking short-term rental options on Anna Maria Island. The outdoor living area enhances the relaxed Florida lifestyle with a heated pool and spa, outdoor bar with sink, and multiple areas for dining and lounging. The oversized lot adds a sense of privacy, creating an inviting retreat for both owners and guests. This layout appeals to a variety of uses, including a multi-residence setup, a dual-unit investment property, or a home offering separation between living space and guest accommodations while maintaining rental flexibility. Located just a short walk to the Gulf beaches, as well as nearby dining, shopping, and island amenities, this property captures the ease and charm of Holmes Beach living. For buyers searching for an updated two-unit home with a pool, walkable beach access, and strong rental potential, Pool Party South and Pool Party North provide a compelling blend of lifestyle and opportunity on Anna Maria Island.

314 61st Street, Holmes Beach

$5,140,000

Experience the ultimate island paradise in this practically NEW CONSTRUCTION LUXURY WATERFRONT HOME, thoughtfully designed with solid concrete block construction and cutting-edge design and technology. Spanning over 3,300+ square feet, this stunning residence offers 4 bedrooms and 5 full bathrooms, blending elegance, durability, and effortless coastal living. Perfectly positioned just a few short blocks from the Gulf of America, the home also boasts PANORAMIC Intracoastal waterfront views, creating a rare and breathtaking dual-water lifestyle. The half-elevated design provides peace of mind while enhancing views and architectural appeal. Indoors, no detail has been overlooked. Highlights include a butler’s pantry, an upstairs coffee bar just outside the primary suite, and expansive open-concept living spaces ideal for both everyday comfort and entertaining. The luxurious primary retreat offers a serene escape with spa-inspired finishes and seamless indoor-outdoor flow. Step outside to your private waterfront oasis featuring an infinity pool, hot tub, and a fully equipped outdoor kitchen, all designed to maximize sunset views and coastal breezes. Whether hosting guests or enjoying a quiet evening under the stars, this outdoor space is truly exceptional. With waterfront living, modern luxury, and a premier island location, this home offers everything you could ask for—and more. A rare opportunity to own a refined coastal sanctuary that perfectly balances style, comfort, and location. Schedule your private showing today!

4 Beds ⋅ 5 Baths ⋅ Sunrise Park SubDv. ⋅ 34217 Zip Code

Experience the ultimate island paradise in this practically NEW CONSTRUCTION LUXURY WATERFRONT HOME, thoughtfully designed with solid concrete block construction and cutting-edge design and technology. Spanning over 3,300+ square feet, this stunning residence offers 4 bedrooms and 5 full bathrooms, blending elegance, durability, and effortless coastal living. Perfectly positioned just a few short blocks from the Gulf of America, the home also boasts PANORAMIC Intracoastal waterfront views, creating a rare and breathtaking dual-water lifestyle. The half-elevated design provides peace of mind while enhancing views and architectural appeal. Indoors, no detail has been overlooked. Highlights include a butler’s pantry, an upstairs coffee bar just outside the primary suite, and expansive open-concept living spaces ideal for both everyday comfort and entertaining. The luxurious primary retreat offers a serene escape with spa-inspired finishes and seamless indoor-outdoor flow. Step outside to your private waterfront oasis featuring an infinity pool, hot tub, and a fully equipped outdoor kitchen, all designed to maximize sunset views and coastal breezes. Whether hosting guests or enjoying a quiet evening under the stars, this outdoor space is truly exceptional. With waterfront living, modern luxury, and a premier island location, this home offers everything you could ask for—and more. A rare opportunity to own a refined coastal sanctuary that perfectly balances style, comfort, and location. Schedule your private showing today!

511 Bayview Drive, Holmes Beach

$1,399,900

The fabulously updated kitchen and open floor plan, make this 3 bedroom/2 bath half duplex a picture perfect island escape. Ideally situated on a quiet corner lot in the heart of the island, it is a straight walk down the street to the sugar sand beach, making it a popular vacation rental too! The split bedroom plan is perfect for hosting, and the updated, private, heated pool and trellis invite you to step out your wall of sliders and enjoy the Florida sunshine. You will love the coastal charm of the beach inspired décor, with wainscoted walls, freshly painted interior, white wood trim, tile flooring throughout, recessed lighting, stainless steel appliances, quartz counters, farmhouse sink and white shaker style cabinetry to the ceiling. Step out for a dip in the pool from your large primary en suite with high ceilings, and a bathroom with dual vanity and a walk in shower. Your spacious guest rooms on the other side of the house, are privately situated and enjoy ample natural light through large windows. This slice of paradise is perfectly situated, with easy beach access and just down the street from the free trolley stop. Enjoy your island time stress free in this like-new home!

3 Beds ⋅ 2 Baths ⋅ 67th Coastal Cottages Or2448/1887 SubDv. ⋅ 34217 Zip Code

The fabulously updated kitchen and open floor plan, make this 3 bedroom/2 bath half duplex a picture perfect island escape. Ideally situated on a quiet corner lot in the heart of the island, it is a straight walk down the street to the sugar sand beach, making it a popular vacation rental too! The split bedroom plan is perfect for hosting, and the updated, private, heated pool and trellis invite you to step out your wall of sliders and enjoy the Florida sunshine. You will love the coastal charm of the beach inspired décor, with wainscoted walls, freshly painted interior, white wood trim, tile flooring throughout, recessed lighting, stainless steel appliances, quartz counters, farmhouse sink and white shaker style cabinetry to the ceiling. Step out for a dip in the pool from your large primary en suite with high ceilings, and a bathroom with dual vanity and a walk in shower. Your spacious guest rooms on the other side of the house, are privately situated and enjoy ample natural light through large windows. This slice of paradise is perfectly situated, with easy beach access and just down the street from the free trolley stop. Enjoy your island time stress free in this like-new home!

302 67th Street, Holmes Beach

$4,295,000

Welcome to "Black Pearl"! Discover refined island living in this exceptional 2024 custom-built residence, ideally situated just 1.5 blocks from the pristine Gulf beaches. Designed with sophistication and comfort in mind, this 4-bedroom, 4-bath elevated home offers a seamless blend of modern elegance and coastal charm. The light-filled great room showcases designer furnishings, premium finishes, and expansive living and dining spaces. The gourmet kitchen is a true showpiece, featuring quartz countertops, custom wood cabinetry, Dacor high end appliances, large island and wet bar with ice maker just off the dining room. Four spacious bedrooms and bathrooms provide privacy and luxury for residents and guests alike. An elevator services every level from the outside pool area all the way up to the roof top deck complete with firepit, enhancing ease of living. Step outside to your private resort-style sanctuary complete with a heated pool, spa, and lush tropical landscaping with turf. Multiple covered balconies and outdoor living areas create inviting spaces for relaxation or elevated entertaining. Offered fully furnished, this residence embodies turnkey luxury on Anna Maria Island. A rare opportunity to own a newly constructed coastal retreat in one of Holmes Beach’s most desirable locations on a dead end street. The home is barely lived in and is just being started as a weekly rental the end of November which will become a superb investment property or make it your very own. Do not miss out on this amazing property! Schedule your showing today!

4 Beds ⋅ 4 Baths ⋅ Holmes Beach 11th Unit SubDv. ⋅ 34217 Zip Code

Welcome to "Black Pearl"! Discover refined island living in this exceptional 2024 custom-built residence, ideally situated just 1.5 blocks from the pristine Gulf beaches. Designed with sophistication and comfort in mind, this 4-bedroom, 4-bath elevated home offers a seamless blend of modern elegance and coastal charm. The light-filled great room showcases designer furnishings, premium finishes, and expansive living and dining spaces. The gourmet kitchen is a true showpiece, featuring quartz countertops, custom wood cabinetry, Dacor high end appliances, large island and wet bar with ice maker just off the dining room. Four spacious bedrooms and bathrooms provide privacy and luxury for residents and guests alike. An elevator services every level from the outside pool area all the way up to the roof top deck complete with firepit, enhancing ease of living. Step outside to your private resort-style sanctuary complete with a heated pool, spa, and lush tropical landscaping with turf. Multiple covered balconies and outdoor living areas create inviting spaces for relaxation or elevated entertaining. Offered fully furnished, this residence embodies turnkey luxury on Anna Maria Island. A rare opportunity to own a newly constructed coastal retreat in one of Holmes Beach’s most desirable locations on a dead end street. The home is barely lived in and is just being started as a weekly rental the end of November which will become a superb investment property or make it your very own. Do not miss out on this amazing property! Schedule your showing today!

305 55th Street, Holmes Beach

$1,079,000

PRIME LOCATION | BRAND NEW RENOVATIONS | ELEVATED-LUXURY-LIVING | ELEVATOR | FENCED SALTWATER POOL | MOVE-IN READY | Located on a peaceful street and embraced by the natural beauty of a mangrove preserve, this elevated coastal residence delivers privacy, modern luxury, and a coveted Holmes Beach lifestyle. Thoughtfully renovated over seven months between 2023 and 2024 with the owners investing $275,000 in premium renovations and high-end additions, the home blends timeless design with state-of-the-art upgrades—creating a tranquil retreat just moments from award-winning Gulf beaches, local dining, and island conveniences. Inside, sunlit living spaces showcase elegant finishes and open-concept design. The kitchen is a modern showpiece, featuring sleek granite countertops, white shaker cabinetry, under-cabinet lighting, and a reverse osmosis water system. Two spacious bedrooms and two spa-inspired bathrooms offer comfort and style, complemented by plantation shutters, smooth ceilings, and a whole-home water filtration system. No detail has been overlooked—from new electrical wiring and panel with underground service to a NEW GARAGE DOOR AND OPENER (2025) and a fully accessible 750-LB CAPACITY ELEVATOR for effortless living. Outdoors, a private fenced backyard oasis invites relaxation with a BRAND NEW ELEVATED SALTWATER POOL (2025) surrounded by lush tropical landscaping enhanced with $20,000 in new plantings, including orange trees and lavender bushes. The serene mangrove backdrop ensures rare tranquility, natural beauty, and panoramic views from your bedroom. The lower level includes a TWO-CAR TANDEM GARAGE and an additional 480 SQUARE FOOT BONUS ROOM with durable polyaspartic-coated flooring. Currently serving as a spacious room for entertainment this can easily be turned into a gym or extra office space—plus an outdoor shower and additional storage. Zoned for MONTHLY VACATION RENTALS and already having a strong rental history, this property offers both investment appeal and a luxurious personal retreat. Located minutes from the Manatee Bridge, Bridge Street, and the North End of Anna Maria Island, this Holmes Beach jewel captures the essence of refined coastal island living. Don’t miss your slice of paradise — schedule your private tour today!

2 Beds ⋅ 2 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code

PRIME LOCATION | BRAND NEW RENOVATIONS | ELEVATED-LUXURY-LIVING | ELEVATOR | FENCED SALTWATER POOL | MOVE-IN READY | Located on a peaceful street and embraced by the natural beauty of a mangrove preserve, this elevated coastal residence delivers privacy, modern luxury, and a coveted Holmes Beach lifestyle. Thoughtfully renovated over seven months between 2023 and 2024 with the owners investing $275,000 in premium renovations and high-end additions, the home blends timeless design with state-of-the-art upgrades—creating a tranquil retreat just moments from award-winning Gulf beaches, local dining, and island conveniences. Inside, sunlit living spaces showcase elegant finishes and open-concept design. The kitchen is a modern showpiece, featuring sleek granite countertops, white shaker cabinetry, under-cabinet lighting, and a reverse osmosis water system. Two spacious bedrooms and two spa-inspired bathrooms offer comfort and style, complemented by plantation shutters, smooth ceilings, and a whole-home water filtration system. No detail has been overlooked—from new electrical wiring and panel with underground service to a NEW GARAGE DOOR AND OPENER (2025) and a fully accessible 750-LB CAPACITY ELEVATOR for effortless living. Outdoors, a private fenced backyard oasis invites relaxation with a BRAND NEW ELEVATED SALTWATER POOL (2025) surrounded by lush tropical landscaping enhanced with $20,000 in new plantings, including orange trees and lavender bushes. The serene mangrove backdrop ensures rare tranquility, natural beauty, and panoramic views from your bedroom. The lower level includes a TWO-CAR TANDEM GARAGE and an additional 480 SQUARE FOOT BONUS ROOM with durable polyaspartic-coated flooring. Currently serving as a spacious room for entertainment this can easily be turned into a gym or extra office space—plus an outdoor shower and additional storage. Zoned for MONTHLY VACATION RENTALS and already having a strong rental history, this property offers both investment appeal and a luxurious personal retreat. Located minutes from the Manatee Bridge, Bridge Street, and the North End of Anna Maria Island, this Holmes Beach jewel captures the essence of refined coastal island living. Don’t miss your slice of paradise — schedule your private tour today!

2915 Avenue C, Holmes Beach