Refine Search
Map
Sort by
$975,000
2 Beds ⋅ 2 Baths ⋅ Tiffany Plaza SubDv. ⋅ 34228 Zip Code
Longboat Key living has never been easier than with this beachfront property facing the Gulf. This turnkey, 1,456-square-foot condominium offers two bedrooms and two baths. Entering, your breath is taken away by an unobstructed view of the water. The story only gets better as you enjoy a private balcony where you can take in the sights and sounds of the crashing waves and unwind to unforgettable sunsets over the Gulf. It comes fitted with hurricane shutters, a renovated sliding door, a washer and dryer hookup, and the kitchen and baths were remodeled in 2012. Plus, you'll have a reserved parking spot to call your own. Get acquainted with the easygoing neighbors, take the family for a swim in the pool at the renovated clubhouse, or cook a nice meal in the outdoor barbecue area, all set among beautifully landscaped grounds. And if the pool isn't your style, that's okay, you can get acquainted with nature firsthand! The owners note frequently sighting dolphins treading the water and sea turtle nests right outside their door.

4325 Gulf Of Mexico Drive Unit 402, Longboat Key
$1,275,000
2 Beds ⋅ 2 Baths ⋅ Anna Maria Island Club SubDv. ⋅ 34217 Zip Code
Experience coastal living at its finest in the highly sought after Anna Maria Island Club. Located in the heart of Bradenton Beach, this exceptional 2 bedroom, 2 bath end-unit condominium offers stunning Gulf views, direct beach access, and the rare opportunity for bi-weekly rentals. Wake up to the sound of the waves and spend your days enjoying everything island life has to offer. This residence features an open and inviting floor plan filled with natural light, a spacious living and dining area, crown molding, solid wood cabinetry, solid surface countertops, and a covered porch overlooking the beauty of the Gulf of America. Anna Maria Island Club offers resort-style amenities, including a Gulf front community pool with a newly renovated travertine pool deck, elevator access, assigned under building parking, additional storage, and beautifully maintained grounds. Recent community enhancements include new roofs, exterior painting, and refreshed landscaping, providing peace of mind for years to come. Located on the desirable north end of Bradenton Beach, you'll be just moments from local boutiques, waterfront dining, and the free island trolley, making it easy to explore all seven miles of Anna Maria Island. Whether you're searching for a beachfront escape, a full time residence, or an investment opportunity with excellent rental potential, this property offers the perfect blend of luxury, convenience, and island charm. Discover why life is better at the beach and make Anna Maria Island your next address.

2600 Gulf Drive N Unit 30, Bradenton Beach
$885,000
2 Beds ⋅ 2 Baths ⋅ Long Beach SubDv. ⋅ 34228 Zip Code
Never miss another beach day or a green flash sunset in this rarely available 2 bed 2 bath home in the Longbeach Community- a GULF FRONT enclave on the tip of Longboat Key. A short walk to the beach, thoughtfully remodeled and move-in ready, this residence offers spectacular daily views of the Gulf, pool, and lush tropical landscaping- best enjoyed on the 200 sqft screened terrace where there’s plenty of room for reading, relaxing or toasting the sunset and dining. This lovely residence has been loved and meticulously upgraded with superior materials and workmanship. The gourmet kitchen features a spacious central cooking island with Electrolux 6-burner cooktop and hood, brushed stainless GE Monogram and Bosch appliances including a stacked double oven, as well as granite countertops, and solid light cherry cabinets. A breakfast bar, wine rack and built-in office complement this kitchen with added functionality. Additional luxury finishes include raised ceilings, crown molding, hidden surround-sound speakers, and spa-inspired bathrooms with custom mosaic-tile showers, Kohler fixtures, and rain showerheads. The Longbeach Community offers 9.2 acres of Gulffront beach homes just a 5-min walk to the exclusive amenities like private beach access to the quartz-white sand of Longboat Key's beaches, a heated pool, private tennis, and ample parking. In addition to idyllic award-winning beaches, Longboat Key living means exquisite waterfront dining, boutique shopping in St Armands Circle, and unparalleled golf courses and tennis courts. The Longboat Key lifestyle awaits you to create new everlasting memories here in paradise!

7115 Gulf Of Mexico Drive Unit 23, Longboat Key
$1,050,000
2 Beds ⋅ 3 Baths ⋅ Bermuda Bay Club SubDv. ⋅ 34217 Zip Code
***UNBELIEVABLE BRADENTON BEACH VALUE***Imagine waking up just 100 steps from the pristine white-sand beaches of Bradenton Beach on the Gulf of Mexico and ending each day with spectacular Gulf sunsets. Located directly across the street from the beach in the highly sought-after Bermuda Bay Club, this beautifully maintained, Key West-style townhouse offers 2 bedrooms, 2.5 baths, a rare private elevator and oversized 2-3 tandem car garage, water views, and weekly rentals permitted, making it the perfect island getaway, full-time residence, or investment property. The main living level features an open-concept floor plan with a bright family room, dining area, eat-in kitchen with brand-new stainless-steel appliances, guest half bath, and laundry. Step outside to the large Trex-deck balcony and enjoy refreshing coastal breezes along with views of both the Intracoastal Bay and the turquoise waters of the Gulf of Mexico. Recently installed hurricane-impact windows and doors provide peace of mind, energy efficiency, and abundant natural light throughout. Upstairs, you'll find two spacious ensuite bedrooms, each with walk-in closets. The primary suite features a private balcony with water views, creating the perfect place to unwind after a day in the sun. The guest suite offers comfortable accommodations for family and friends, making this property ideal as a personal retreat or income-producing vacation rental. A rare feature for island living, the oversized tandem garage offering plenty of room for vehicles, beach gear, bicycles, kayaks, paddleboards, and even a golf cart. An outdoor shower and rear deck make rinsing off after a day at the beach easy and convenient, while the private elevator provides effortless access to all levels of the home. Bermuda Bay Club offers resort-style amenities including a heated pool and spa, grilling area, and a private boardwalk through the mangroves where you can enjoy watching dolphins, pelicans, and other native wildlife along the Intracoastal Waterway. Perfectly positioned between the Gulf and the Bay, this exceptional property is within walking distance of the popular Historic Bridge Street with restaurants, shopping, bars, and plenty of entertainment. The free Anna Maria Island Trolley stops directly in front of the community, providing convenient access to the entire island without ever needing a car. Start your mornings with a walk along the beach, spend your afternoons by the pool or exploring the island, and end your evenings enjoying breathtaking Florida sunsets Whether you're seeking a full-time residence, vacation getaway, or investment property, Bermuda Bay Club offers weekly rentals permitted, lower condo fees, resort-style amenities, and one of the most desirable locations on Anna Maria Island. Opportunities to own a property with a private elevator, tandem garage, stunning water views, and beach access within 100ft to the Gulf and 50ft to the Bay are rare! Don't Just Dream It... Live It and start living your own Florida Paradise today!

1469 Gulf Drive N, Bradenton Beach
$725,000
2 Beds ⋅ 3 Baths ⋅ Summer Sands SubDv. ⋅ 34217 Zip Code
Exclusive waterfront living in Bradenton Beach! On the pristine shores of Anna Maria Island, this exquisite condominium offers an unparalleled blend of luxury, privacy and breathtaking beach and sunset views. In an exclusive 36-residence community, this intimate complex is positioned between a sparkling heated pool with a spa and the sugary sands of the beach. Across the street, the land is owned by Summer Sands Association where no structures will be built to block your view, and also provides direct deeded beach access and a Tiki Hut to relax with a cool beverage. Designed for tranquility and convenience, this spacious two-bedroom, two-and-a-half-bath retreat boasts expansive windows that flood the space with natural light, accentuating the sweeping coastal vistas. Recently designed with luxury vinyl flooring, an updated kitchen and fresh paint, this furnished, move-in-ready home provides impact hurricane-rated windows, high vaulted ceilings, a washer and dryer inside the unit and a split bedroom floor plan, with each bedroom offering an ensuite bath. Culinary enthusiasts can enjoy the gorgeous kitchen, with quartz counters, soft-close drawers and cabinets and stainless steel appliances. The unit is outfitted with the primary bedroom on the first floor plus a half bath just off the main living area, offering convenient access for you and your guest, and a second-floor loft-style guest bedroom or office. This pet-friendly community provides a bayfront heated community pool and spa with an upgraded pool deck, bathhouse, boat and fishing dock, kayak and paddleboard storage and social gatherings. Have peace of mind knowing the association reserves are fully funded and had a new roof installed in 2025, updated the elevators and added beautiful landscaping throughout. With a 30-day minimum rental policy up to four times per year, the community maintains an exclusive, low-turnover atmosphere, ideal for those seeking a more serene coastal escape. Covered parking under the building adds convenience with two parking spots, plus a building elevator, and the community pool and spa provide a picturesque setting for outdoor gatherings and events. Ideally located, this residence offers effortless access to the charming shops, acclaimed dining and vibrant culture of Bradenton Beach and Anna Maria Island. Experience Gulf view living at its finest, where tranquility, luxury and convenience converge. Schedule your private showing today.

1007 Gulf Drive N Unit 208, Bradenton Beach
$4,250,000
5 Beds ⋅ 4 Baths ⋅ Sportsmans Harbor SubDv. ⋅ 34217 Zip Code
Located in the heart of Holmes Beach on Anna Maria Island, this reimagined waterfront home offers deep-water boating access, direct Gulf views, elevator access, and a beach location that is hard to beat, just steps from the front door to the sand. Set on one of the closest canal-front streets to the beach, the property provides protected dockage, quick access to Tampa Bay, downtown St. Petersburg, and the Gulf of Mexico, along with the everyday ease of true island living. Originally rebuilt from the block in 2022 in collaboration with Richard Haas, the home was thoughtfully redesigned with clean architectural lines, quality coastal construction, and low-maintenance ownership in mind. The result is a modern Anna Maria Island waterfront residence built for comfort, efficiency, and long-term durability without sacrificing style, function, or quality. Inside, the living spaces were designed to maximize natural light and keep water views connected to daily life. The main living area, kitchen, and secondary primary suite all capture direct Gulf views, while large glass openings connect the interior spaces to the outdoor terraces. A custom floating red oak staircase serves as a striking architectural focal point and adds warmth to the clean modern design. The kitchen was designed for both entertaining and everyday use, featuring Cosentino Quartz counters, custom full-height cabinetry, JennAir Professional appliances, and a walk-in pantry. More than fifteen slabs of quartz were incorporated throughout the kitchen and bedroom suites, creating a consistent level of finish throughout the home. Smart-home features, remote-controlled shades, custom lighting, elevator access, and thoughtfully curated finishes contribute to a comfortable and efficient living environment. The primary suite offers a private retreat with a custom-built walk-in closet and a spa-inspired bath featuring Toto fixtures, dual vanities, and multi-function shower features. Additional upgrades include dual high-efficiency HVAC systems, buried gas storage, generator readiness, tankless water heaters, and water-softening systems. A newly installed dock and Golden boat lift accommodate larger vessels, while recent dredging improves canal access for serious boaters. Combining modern coastal architecture, deep-water boating access, Gulf views, updated construction, and one of the most walkable beach locations on Anna Maria Island, this Holmes Beach waterfront residence represents a rare opportunity within Florida's luxury coastal market. Easy access to North bridge/Manatee Ave via two different routes. Please note: A pool permit has been approved. Pool plans, specifications, and contractor quote are available in the attachments.

201 N Harbor Drive, Holmes Beach
$1,595,000
3 Beds ⋅ 3 Baths ⋅ Anna Maria Beach SubDv. ⋅ 34216 Zip Code
FINANCING FELL THROUGH BACK ON THE MARKET!!! Welcome to your dream getaway, an adorable bungalow located on the north end of Anna Maria Island, directly across from the beach and a lovely park. This charming 3-bedroom, 3-bathroom home is perfect for a full-time residence, an income-generating rental, or a part-time retreat—all in an unbeatable location. Step inside to discover a welcoming living room with beautiful hardwood floors and delightful beach views, seamlessly connecting to the dining area for an open and inviting layout. The kitchen features wood cabinets, sleek quartz countertops, and stainless steel appliances, along with convenient countertop seating. The spacious primary bedroom includes a cozy sitting area and French doors that frame stunning beach views, complemented by an updated en-suite bathroom with a stylish glass shower. The second bedroom also boasts its own en-suite, providing comfort and privacy for guests. Outside, enjoy your private deck, ideal for sunbathing and grilling, complete with an outdoor shower for rinsing off after a day at the beach. The heated pool offers a refreshing retreat on warm days, while the covered, screened front porch is the perfect spot to relax with morning coffee and take in the serene blue waters. Located close to Pine Avenue’s boutique shops, delightful restaurants, and the picturesque Bean Point, this property features a durable metal roof, hardy board siding, and newer windows, enhancing its appeal and longevity. Don’t miss the chance to make this charming bungalow your own—schedule your showing today and embrace the island lifestyle!

317 N Bay Boulevard, Anna Maria
$1,100,000
2 Beds ⋅ 2 Baths ⋅ Tiffany Plaza SubDv. ⋅ 34228 Zip Code
Experience coastal living in this two-bedroom, two-bath direct Gulf-front residence ideally on the main floor of a desirable mid-rise community on Longboat Key. Freshly painted and thoughtfully enhanced with quartz countertops in both the kitchen and laundry room, along with recently updated washer and dryer appliances, the residence also features crown molding, updated trim and plantation shutters throughout, as well as Gulf-side hurricane shutters. The covered Gulf-side lanai provides the perfect setting to relax and enjoy the coastal surroundings year-round. The primary bedroom offers a very large walk-in closet. This residence includes a designated covered parking space along with private exterior storage. Residents enjoy an impressive array of amenities, including a clubhouse with a sauna, a heated Gulf-front pool, an interlocking stone patio and barbecue, a covered area and direct beach access. Ideally in a sought-after mid-key location, the property is close to St. Armands Circle, with its renowned boutiques, dining and shopping, while downtown Sarasota is just over the bridge, offering arts, culture, dining and entertainment. Heading north, enjoy convenient access to Anna Maria Island, while heading south, you will find the many amenities of Longboat Key, including Publix, CVS, places of worship, banks, parks, town hall, Bayfront Park, public tennis courts, boat launches and more.

4325 Gulf Of Mexico Drive Unit 103, Longboat Key
$2,990,000
4 Beds ⋅ 4 Baths ⋅ Snead Island SubDv. ⋅ 34221 Zip Code
One or more photo(s) has been virtually staged. Welcome to a reimagined waterfront estate on the exclusive shores of Snead Island, where elevated design meets an effortless Gulf-front lifestyle. Extensive high-end renovations make this residence a thoughtfully transformed, refined coastal-chic retreat. Offering 4 bedrooms, 3.5 bathrooms, and a private office/executive suite, this residence is thoughtfully designed to blend refined interiors with an extraordinary waterfront lifestyle. Stunning natural hardwood floors flow throughout the home, while the beautifully renovated kitchen serves as the heart of the residence, perfectly positioned to overlook the beach and breathtaking Gulf views, creating an inspiring backdrop for everyday living and entertaining. The open-concept floor plan allows for effortless gatherings, seamlessly connecting the main living spaces and inviting the outdoors in through picturesque water vistas. The dining room is ideally situated to capture memorable meals, meaningful conversations, and sunset-filled evenings with family and guests. A private elevator further enhances the home’s comfort and convenience, providing effortless access between levels. The private office or executive suite offers a rare and tranquil work environment, with calming beach views that transform the workday into something exceptional. The primary suite is a peaceful retreat, complete with a beautifully renovated spa-style bathroom, private exterior access, and its own charming porch, an intimate setting to enjoy morning coffee or unwind in the evening breeze. Every space within the home has been curated with a clean, sophisticated aesthetic that balances comfort, elegance, and the unmatched beauty of its coastal surroundings. Beyond the interiors, the property unfolds into an oversized, newly landscaped homesite, leading to your own private beachfront escape where you will experience unobstructed sunset views. A brand-new roof further enhances the home’s turnkey appeal. Perfectly positioned within the coveted Snead Island community, this residence offers an exceptional balance of privacy and accessibility. Conveniently connected to St. Petersburg, Tampa, and Sarasota, surrounded by the tranquil waters of Terra Ceia Bay, Tampa Bay, and the Manatee River, and near the 365-acre Emerson Point Preserve, residents enjoy effortless access to boating, nature trails, kayaking, and some of the region’s most pristine coastal landscapes. Also a great opportunity for a potential income property - Air Bnb or VRBO. An exclusive offering of privacy, design, and waterfront living. Truly a must see!

5216 13th Street, Palmetto
$5,600,000
Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
Build your dream beachfront estate on nearly three-quarters of an acre on exclusive North Longboat Key. With 100 feet of private Gulf frontage, this rare homesite offers endless views of turquoise waters spectacular sunsets and direct access to powder sand just steps from your future doorstep. Set within a rising luxury enclave, this prime property is moments from the new St. Regis Resort and the Longboat Key Club, offering world-class golf, tennis, dining, and five-star amenities. Enjoy the charm of nearby Anna Maria Island and the upscale shopping and cultural experiences of St. Armands Circle. This is one of the last opportunities to create a custom beachfront retreat in one of the Gulf Coast’s most coveted locations

6441 Gulfside Road, Longboat Key
$4,095,000
4 Beds ⋅ 5 Baths ⋅ Shore Acre Heights SubDv. ⋅ 34216 Zip Code
Located just two blocks from Bean Point on the coveted north end of Anna Maria Island, this beautifully designed 2023 residence offers a rare combination of privacy, walkability, and elevated coastal living. Never used as a rental, the home has been carefully maintained as a private retreat and is offered fully furnished. Professionally designed by Emily Moss Designs and recognized by SRQ Magazine as a 2025 Home of the Year, the residence blends architectural detail with relaxed island elegance. The main living level features an open floor plan with coffered ceilings, gas fireplace, wet bar, powder room, and balcony access. The primary suite includes a private balcony, walk-in closet, dedicated laundry area, and a spacious spa-style bath with soaking tub and multi-feature shower. The large chef’s kitchen is appointed with distinctive cabinetry, Thermador appliances, generous island seating for five, and an inviting eat-in dining area designed for effortless everyday living and entertaining. A detached guest suite connected by a covered walkway offers its own private entrance, refrigerator, full bath, private balcony overlooking the pool, and garage—ideal for extended family or guests seeking independence and privacy. Upstairs, two additional king en-suite bedrooms with vaulted beamed ceilings are centered around a private second-level sitting area with television, balcony access, and laundry room—creating a comfortable and well-separated guest retreat. Two rooftop decks capture sweeping Gulf views and vistas toward the Sunshine Skyway Bridge—perfect for sunrise, sunset, and evening skies. Outdoor living centers around a beautifully landscaped private courtyard complete with pool, heated spa, putting green, and an expansive covered lanai designed for year-round enjoyment. A two-person dry sauna and flexible lower-level space add further comfort and versatility. Constructed in 2023 with elevated hurricane-rated block construction, impact windows and doors, a metal roof, and low-maintenance composite decking, the home combines durability with thoughtful design. Elevator access to all living levels and multiple garage bays with gated boat or RV storage provide exceptional convenience and parking flexibility—rare on the north end. Situated on a desirable corner lot just moments from the Gulf and Pine Avenue, this is a unique opportunity to own a nearly new, designer-furnished island residence in one of Anna Maria’s most sought-after locations. Detailed property brochure available.

416 Alamanda Road, Anna Maria
$6,495,000
Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
Rarely does an estate-sized Gulf-front lot of this stature become available on the northern end of Longboat Key. 6351 Gulf of Mexico Drive presents a truly exceptional 100-foot by 388-foot direct beachfront parcel — nearly 39,000 square feet of pristine Gulf of Mexico frontage. This distinguished property stands as one of the final remaining full beachfront estate-sized lots on Longboat Key, offering a rare and significant opportunity. Commanding sweeping, unobstructed views of the turquoise Gulf waters and the iconic white-sand shoreline, the site serves as a unique blank canvas for the creation of a bespoke oceanfront residence. The expansive and generously proportioned dimensions provide unparalleled design flexibility, allowing the accomplished buyer to fully realize a custom legacy property tailored to the highest standards of coastal elegance, privacy, and sophistication. Ideally situated, the property enjoys convenient proximity to the prestigious Longboat Key Club with its 45 holes of championship golf, tennis facilities, and fine dining. World-class restaurants are moments away, including The Shore, Whitney’s, Mar Vista, Euphemia Haye, and Lazy Lobster. Additionally, St. Armands Circle offers exceptional shopping and dining, while the fine and performing arts venues of downtown Sarasota are easily accessible. Positioned among notable residences yet defined by its substantial scale and immediate beach access, this parcel delivers the rare combination of exclusivity and architectural freedom. It is an offering for the discerning individual who has earned the right to create precisely what they envision — a timeless private sanctuary in one of Florida’s most prestigious coastal communities. Private showings by appointment.

6351 Gulf Of Mexico Drive, Longboat Key
$999,000
2 Beds ⋅ 2 Baths ⋅ Tiffany Plaza SubDv. ⋅ 34228 Zip Code
Direct beachfront living! This beautifully updated 2-bedroom, 2-bath residence offers unobstructed Gulf of Mexico views and front-row access to a slice of Longboat Key’s most quiet and uncrowded shoreline. Available fully furnished and turnkey, this condo is ready for immediate enjoyment as a primary residence, seasonal escape, or investment property. The spacious open layout connects the kitchen, dining, and living areas, creating a bright and functional space designed to maximize natural light and water views. The private balcony is the perfect place to spot dolphins, manatees and other wildlife while enjoying morning coffee or evening sunsets. With only 42 residences, Tiffany Plaza offers a more private and welcoming atmosphere than larger condominium communities, with an active clubhouse and strong sense of community among owners. Residents also enjoy close proximity to Bayfront Park, featuring dog parks, tennis, pickleball, kayak facilities, fitness classes, and beautiful bay front walking paths.

4325 Gulf Of Mexico Drive Unit 305, Longboat Key
$675,000
1 Beds ⋅ 2 Baths ⋅ Whitney Beach SubDv. ⋅ 34228 Zip Code
Finally, you have the opportunity to own your own "Walk-Out", Gulf Front, Beach Condo. Tucked just behind a beach grass sand dune and situated on a grassy knoll, this unit is perfectly positioned to benefit from refreshing sea breezes while offering spectacular sunset views. This rare one-bedroom condo has been completely remodeled and now features a unique two-bathroom floorplan. Remodeled Interior and Modern Upgrades: The spacious living area boasts premium appliances and upgraded stone countertops on new cabinetry within a newly designed open kitchen. Updates abound throughout the unit: new hurricane impact resistant sliding doors and a front window, along with modern bathrooms. The property is being sold turn-key—everything stays, making it a seamless move-in experience. Step inside and discover a bright, inviting interior with an open, light-filled layout designed to maximize both space and natural beauty. Large glass sliders connect the interior to the outdoors, bathing the kitchen and living area in sunlight and blending innovative functionality with coastal charm. The thoughtfully designed bedroom and bathrooms provide serene retreats, perfectly balancing comfort and style. Private Outdoor Oasis: The unique ground floor “Whitney Beach Gulfside” floorplan offers both a front privacy-fenced enclosed patio—ideal for alfresco dining or beachfront gardening—and a rear open patio for relaxation. Whether enjoying a quiet morning coffee or an evening cocktail, the gentle sea breeze creates the perfect setting for unwinding. Resort-Style Community Amenities: Enhance your lifestyle with a range of well-maintained community amenities, including a sparkling pool, tennis courts, shuffleboard, beach chairs, boat slips available for lease, and a tranquil pavilion by the bayou for water enthusiasts. Unmatched Location and Lifestyle: Experience the best of coastal living on Longboat Key. Whitney Beach is located on the quiet, northern end of Longboat Key, close to fantastic restaurants, shops, and shopping—just steps away, an easy bike ride, or a short drive to visit St Armands Circle. This condo combines a highly desirable location with the privacy and comfort of a casual beachfront lifestyle—perfect for year-round living, a seasonal retreat, or a smart investment. With one-month minimum rentals allowed up to 12 times per year, the property offers excellent investment potential. BONUS: the community features two-story buildings and is exempt from Florida’s Milestone inspection and reporting requirements, ensuring a NO SURPRISE experience. Discover Longboat Key: Enjoy the finest Longboat Key has to offer, where luxury meets laid-back coastal charm. Schedule your private tour today!

6701 Gulf Of Mexico Drive Unit 332, Longboat Key
$699,000
2 Beds ⋅ 2 Baths ⋅ Seagrass Flats SubDv. ⋅ 34217 Zip Code
Turnkey beachside investment with a strong, proven rental history and loyal repeat guests—exceptionally positioned and priced to stand out, just steps from the sugar-white sands of the Gulf. This beautifully updated 2-bedroom, 2-bath condo effortlessly blends coastal charm with income-producing potential in a 4-unit boutique setting. Fully renovated and offered fully furnished, the home showcases a light, airy interior with shiplap and wainscoting accents, durable luxury vinyl plank flooring, and an updated kitchen with newer appliances. A convenient laundry closet with recently replaced washer and dryer adds everyday ease. Two king bedrooms plus a sleeper sofa maximize comfort and guest capacity, while both bathrooms feature quartz countertops and refined designer finishes. With a consistent history of repeat guests, this property is as enjoyable as it is profitable. Recent upgrades—including a new roof (2024), hurricane impact windows (2025), updated plumbing (2022), water heater and AC (2020)—provide lasting value and added peace of mind. Begin your mornings with coffee and a sea breeze from your front porch, spend afternoons poolside or on the beach just across the street, and unwind with unforgettable Gulf sunsets. With dining, shops, parks, and the island trolley all nearby, every day feels effortlessly like a getaway. Whether you're seeking a high-performing investment, a personal retreat, or both, this is island living at its finest.

101 25th Street N Unit 1, Bradenton Beach
$10,950,000
5 Beds ⋅ 8 Baths ⋅ Shore Acres SubDv. ⋅ 34216 Zip Code
Experience one of the most extraordinary waterfront settings on the coveted North End of Anna Maria Island, just moments from the world-renowned shores of Bean Point. Set on over an acre of Gulf-front beachfront land, this rare estate provides exceptional privacy, expansive shoreline, and breathtaking panoramic views of the Gulf of Mexico. In 2019, the property underwent a comprehensive structural and architectural redevelopment that transformed the residence into a modern coastal estate, including major infrastructure upgrades such as updated electrical, plumbing, and HVAC systems, along with new flooring, custom millwork, redesigned bathrooms, cabinetry, lighting, and modern coastal finishes throughout. Originally constructed as an elevated coastal residence, the home was extensively expanded, redesigned, and structurally reimagined to create a three-level retreat designed for elevated island living. The redevelopment included the addition of a private master suite level, construction of a large elevated pool and entertainment deck, and installation of a dramatic three-story architectural water feature, while completely reconfiguring the interior floor plan. Privately gated and approached by a palm-lined drive, the residence welcomes you with a striking 20-foot waterfall entry. Expansive windows capture nearly 270-degree Gulf views, filling the open living spaces with natural light and coastal breezes. The main living areas flow seamlessly to spacious outdoor terraces finished in Brazilian Walnut (IPE) decking—ideal for sunset entertaining overlooking the Gulf. The chef’s kitchen features custom rosewood cabinetry, three ranges, three ovens, a built-in coffee bar, wine refrigeration, and premium Sub-Zero, Wolf, Cove, and Miele appliances. Multiple bedroom suites include ensuite baths and water views, while a dedicated entertainment level features shuffleboard, a poker table, pool table, and lounge space. The top-floor owner’s retreat, accessible by elevator, captures sweeping Gulf views and includes oversized walk-in closets, a private coffee bar, and a spa-style bath with soaking tub and rain shower. Outdoor amenities include a heated ozone saltwater pool with lap feature, elevated entertainment deck, private gym, infrared sauna, and a two-car garage with additional golf cart space. Direct beach access leads to one of the most peaceful stretches of shoreline on Anna Maria Island. Located near the shops and restaurants of Pine Avenue, this property is a rare opportunity to own a fully transformed Gulf-front estate on over an acre of beachfront land on the North End of Anna Maria Island.

811 N Shore Drive, Anna Maria
$1,100,000
2 Beds ⋅ 2 Baths ⋅ Sunset Terrace SubDv. ⋅ 34217 Zip Code
This two-bedroom, two-bathroom condominium offers one of the finest unobstructed views of the Gulf. Recently updated, the coastal-inspired interior features tiled floors and an unbeatable vantage point for watching amazing sunsets. Guests can enjoy the heated pool or take a short stroll to the beach to enjoy the sugar-sand shores and jeweled waters of the Gulf. The private porch provides the perfect space to relax, while the well-maintained unit ensures comfort with a modern kitchen featuring granite countertops and a large in-unit washer and dryer. This property serves as an excellent vacation rental.

2312 Gulf Drive N Unit 103, Bradenton Beach
$38,450,000
11 Beds ⋅ 17 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code
Under Construction. Set on nearly two private Gulf-front acres, this visionary estate is emerging as one of the most architecturally significant residences ever conceived on Longboat Key. Designed by the internationally acclaimed firm Sweet Sparkman Architecture & Interiors, the home represents a rare convergence of sculptural design, coastal sensitivity, and modern livability. Bold in concept yet timeless in execution, the main residence unfolds with intention. A dramatic foyer introduces expansive living spaces designed to capture light, scale, and uninterrupted Gulf views. The primary suite is conceived as a private sanctuary, complete with dual spa-inspired baths and bespoke dressing rooms. A stately office, refined lounge, formal dining room, and temperature-controlled wine cellar complement the open-concept great room, which transitions seamlessly to a sweeping Gulf-front terrace. Dual kitchens, a showpiece entertaining kitchen and a separate chef’s kitchen, elevate both daily living and grand-scale hosting. The estate continues upward to a rooftop deck with panoramic coastal vistas, while other levels offer a private cinema, multiple guest suites, and a dedicated guest-level kitchenette. A thoughtfully designed guest house and separate pool house provide additional privacy and flexibility for extended stays or staff accommodations. Outdoors, the setting transforms into a private coastal resort. Lush, layered landscaping surrounds a dramatic resort-style pool and spa, expansive entertaining terraces, tranquil water features, and potential for a private tennis and pickleball court — all oriented toward the Gulf’s endless horizon. Positioned along one of the most coveted stretches of Longboat Key, the property offers both seclusion and proximity to the best of the region, including The Resort at Longboat Key Club, The St. Regis Longboat Key Resort, St. Armand's Circle, and the cultural vibrancy of downtown Sarasota. With construction advancing and pricing evolving accordingly, this is a rare opportunity to secure a generational Gulf-front legacy estate at a pivotal stage. Longboat Key’s global recognition, including its inclusion among Forbes Travel Guide’s Top 12 Destinations, further underscores the enduring value of this extraordinary offering.

5965 Gulf Of Mexico Drive, Longboat Key
$775,000
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
$6,245,000
Sunset Cove At Holmes Beach SubDv. ⋅ 34217 Zip Code
Very rare opportunity to own one of the most coveted addresses on Anna Maria Island—Sunset Lane. This estate-sized, over ½-acre beachfront parcel offers 80’ of direct Gulf frontage with an impressive 470’ depth. DEP state permit in hand allows for up to 6,558 sq ft of living space (Ground: 74’ x 58.6’, First Living: 74’ x 58’, Second Living: 67’ x 48.6’). Design and build your dream coastal estate with unobstructed sunset views from every room.

102 Sunset Lane, Holmes Beach
$789,900
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
$13,995,000
4 Beds ⋅ 5 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code
This Seaward Homes Curated Collection residence at 6489 Gulfside is ready for occupancy. Enjoy the ultimate Longboat Key lifestyle with your own direct Gulf-front private access and stunning views of the Gulf of Mexico. Designed by DSDG Architects, this home epitomizes exceptional quality and attention to detail. Come and witness the cutting edge of enhanced hurricane construction, wander and enjoy the exquisite staging by Clive Daneil Homes. Situated on a coveted 90' Gulf/Beach-front lot, the property offers soft sands, endless Gulf views, and miles of walkability. In 2025, Longboat Key completed a significant beach re-nourishment project, giving Gulfside Road homeowners one of the widest and deepest stretches of beach on the entire island. Equally notable, Gulfside Road is one of the rare Gulf-side streets set back from the main highway, offering a tranquil, private environment that feels worlds away from the activity of Gulf of Mexico Drive. The main house, elevated over 15 feet, features 11' ceilings, four oversized en-suite bedrooms, and more than 6,600 sq ft of air-conditioned living space, including a grade-level, air-conditioned multipurpose room that can be tailored for wellness, fitness, or a variety of additional lifestyle needs. The wide-open floor plan, generous room sizes, and large impact-rated safety glass sliding doors and windows fill the home with natural light. Two nearly 40' terraces on the main and second floors provide ideal spaces to enjoy the outdoor island lifestyle and breathtaking Gulf views. Interior finishes by Studio G Homes elevate luxury living to the next level. The interior finishes include large-format porcelain tile and hardwood flooring, Italian-imported cabinetry, a custom floating steel-and-wood staircase, a three-stop elevator, 8' solid interior doors, high-efficiency mechanical systems, a top-of-the-line Thermador™ appliance package, AXOR™ and Hansgrohe™ plumbing fixtures, temperature-controlled wine storage, and detailed AV, lighting control, and security systems. Exterior features include solid concrete and masonry construction on all floors, a deep concrete piling foundation for added strength, Longboard™ premium aluminum architectural details, and a fine light-sand exterior stucco finish. The resort-like pool area and custom spa are surrounded by a lush tropical landscape package. The garage accommodates four cars, with the option to add car lifts. Longboat Key, an 11-mile barrier island, is just minutes from St. Armands Circle and downtown Sarasota. The Sarasota Bradenton International Airport is approximately 25 minutes away. Embrace the opportunity to own this unparalleled residence and experience the pinnacle of coastal luxury living.

6489 Gulfside Road, Longboat Key
$499,000
1 Beds ⋅ 1 Baths ⋅ Covert Condominium SubDv. ⋅ 34228 Zip Code
Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? This is by far the lowest priced direct beachfront condo on the entire island and it is already completely updated! Whether you decide to use it yourself or use it as an investment with outstanding monthly rental income availability, this is the one. With a fabulous ground floor location, you can have your toes in the sand in only a few steps! This condo offers Italian porcelain tile throughout and a completely new kitchen with beautiful counter tops, all new cabinets and new appliances. The bathroom has been beautifully updated as well and features custom tile work in a seaside theme. The view is fabulous in either direction with the sparkling pool out front and the gorgeous Gulf of Mexico out back. The open living and dining area allows plenty of space to entertain or to quietly contemplate whether it’s a beach day, a day for a soak in the pool or a walk to the Covert bayside fishing pier. The bedroom offers the same stunning beach view and features storm rated sliders to the screened in lanai. The midkey location allows for easy access to multiple restaurants and shopping. The tree filled mangrove trails of Joan Durante Park are a birders’ paradise and the 12 mile long bike path give you many options to soak in the sun while getting in your daily exercise. This is island living at its best at a price you may never thought you could find!

5231 Gulf Of Mexico Drive Unit 104, Longboat Key
$5,950,000
Bay Manor Pb7/23 SubDv. ⋅ 34217 Zip Code
Rich in history and ripe with potential on one of the area’s most desirable coastal locations—formerly home to the iconic Queens Gate Resort, the property has been cleared following storm damage and now stands ready for its next chapter. This expansive assemblage of three contiguous parcels and a fourth adjacent parcel offers a clean slate for your vision, whether you’re imagining a boutique lodging experience, a landmark residential development, or a custom dream estate. Zoned R-3, the property presents immense possibilities in a prime location that visionaries will immediately recognize. This is more than a vacant piece of land—it’s your legacy project.

1101 Gulf Drive N, Bradenton Beach
$8,250,000
3 Beds ⋅ 4 Baths ⋅ Shore Acres SubDv. ⋅ 34216 Zip Code
Rising gracefully on the sugar-white sands of Bean Point, The Golden Dolphin is a timeless Gulf-front residence that blends enduring craftsmanship with inspired artistry. The main living level unfolds into a grand living and dining area, where a full wall of sliders frame endless Gulf views and spectacular sunsets. The expansive balcony is an entertainer’s dream, featuring a fully equipped Lynx outdoor kitchen and a beautifully carved fireplace—an inviting setting for al fresco dining or evenings by the fire. Inside, the chef’s kitchen is outfitted with Sub-Zero, Viking, and Miele appliances, seamlessly combining performance and elegance. A refined library retreat, complete with a fireplace and exquisitely carved bookcases, offers a quiet haven for reading or reflection. The third floor is devoted to luxurious private living. The palatial primary ensuite is a serene sanctuary with spa-like amenities and opens to its own Gulf-facing balcony. Here, a soaking tub, rain shower, and an additional fireplace create an indulgent, resort-style experience. Also on this level are a gracious guest suite, a whimsical children’s ensuite bedroom, and a conveniently located laundry room. The first floor welcomes you with a dramatic foyer featuring soaring ceilings and an elevator. Just beyond lies the imaginative Captain’s Quarters, a fantastical space designed to replicate the galley of a pirate’s lair—both playful and unforgettable. An expansive office follows, showcasing granite countertops and intricately carved walls with integrated drawers and shelving, offering both beauty and function. Outdoors, the home transforms into a private oasis. The grotto-style pool provides shaded comfort and is adorned with multiple water features, while a surrounding fireplace and dining area create an intimate setting for gathering. Beyond the pool, a sun-drenched private patio invites leisurely afternoons of relaxation and sunbathing. Built to stand the test of time, The Golden Dolphin is constructed with concrete and rebar throughout and engineered with advanced drainage systems designed to reroute floodwaters. This exceptional residence has sustained no damage from past hurricanes, offering peace of mind alongside its unparalleled beauty. A rare offering on Anna Maria Island, The Golden Dolphin is a masterful expression of luxury, resilience, and coastal elegance—where art, architecture, and the Gulf converge in perfect harmony.

801 N Shore Drive, Anna Maria
$3,150,000
6 Beds ⋅ 6 Baths ⋅ Ilexhurst SubDv. ⋅ 34217 Zip Code
BEACH & GULF VIEWS from this spectacular 6 bedroom, four full + two 1/2 bath luxury pool home located just steps to the beach with easy access. This gorgeous, newer home offers a "reverse floor plan" allowing for amazing views of the beach and sunsets from the top floor. This upper level floor comprises of an open living, dining & kitchen space as well as a beach side deck and powder bath. Two King bedrooms are on this top floor with a shared, "Jack & Jill" bath. A spiral staircase from the beach-side balcony leads to your roof-top sundeck with panoramic water views of BOTH the beach AND the bay... The first living level brings you to a sunlit den and sitting room. The master bedroom on this floor offers views of the beach as well as a spacious, ensuite master bath with large, glass shower. The second bedroom on this level also offers an ensuite bath. Two additional bedrooms (king & full sized bunk) on this floor have a "Jack & Jill" bath with double sinks and a shared tub/shower. The private backyard offers lush landscaping, a fenced yard and a great pool with jacuzzi. A shady, covered dining area, bar, and grilling area make this pool area hard to leave! The garage offers space for shaded parking, a game area & beach supply storage. Tasteful, turn-key furnishings allow for a continuation of vacation rental income. Location allows for NIGHTLY and WEEKLY vacation stays to help maximize your rental potential!

2201 Avenue C, Bradenton Beach
$7,495,000
4 Beds ⋅ 5 Baths ⋅ Bonaire Bayou SubDv. ⋅ 34228 Zip Code
Designed by award-winning architect, John Cooney, and built by Sarasota’s premier coastal homebuilder, Perrone Construction, this mid-Key classic is simply among Longboat Key’s finest homes. Walk in to this fully furnished home which is steps from the beach and with expansive Gulf and Bay views, this masterpiece offers more than 4300 square feet of refined interiors on the main living floors together with multiple large lanais and balconies. A beautiful foyer, large family room, and home gym are featured on the ground floor, along with an oversized three-car garage and storage room. The quality of the home’s design and construction are matched by the charm of the interior finishes and amenities. The living areas incorporate beautiful ceiling elevations, along with custom wide-plank hardwood, Italian porcelain tile, and custom plantation shutters and drapes. The Great Room flows into the chef’s kitchen which features custom cabinetry, quartz countertops, Wolf and SubZero appliances, and a temperature-controlled 275 bottle wine room. Designed for easy entertaining, the Great Room opens onto a large lanai with its gas fireplace and grill, and gorgeous Gulf and sunset views. Adjoining the kitchen is a perfect dining room with its own balcony and Gulf views, as well as a large family office/bonus room with custom cabinetry and bookshelves. The Lutron system controls both the lighting and the custom drapes and shades. The home’s elegant chandeliers and sconces bathe its interior with gracious warmth. The beautiful master suite on the main floor includes a bedroom cathedral ceiling and access to the outdoor lanai. The master bath features custom cabinetry, porcelain tile, a large steam shower, and is plumbed for a master bathtub. Three spacious guest suites, a gathering lounge, and balconies with Gulf views are found on the second living floor. A private elevator connects all levels. Both the home and exterior grounds are designed for year-round, low-maintenance living. An extensive landscape refresh in 2023 included new turf and lighting, an outdoor shower, and a great fire pit area for entertaining. Lush landscaping and a tranquil pool setting provide both screening and privacy. The home features remote controlled screening and storm shutters, extensive use of Azek composite, and other low-maintenance materials, along with a gas generator, whole-house water filtration system, central vacuum, and much more. With miles of pristine beach and bay to explore and with the abundant cultural, dining, and shopping amenities of Sarasota, St. Armand’s Circle, and Anna Maria Island nearby, this timeless home delivers the very best of Longboat Key living.

5005 Gulf Of Mexico Drive Unit 4, Longboat Key
$5,000,000
4 Beds ⋅ 5 Baths ⋅ Shore Acres SubDv. ⋅ 34216 Zip Code
DIRECT BEACHFRONT - This residence generated nearly $500,000 in income for 2025!  Positioned on the pristine shores of the north end of Anna Maria Island, this extraordinary direct beachfront estate offers a rare opportunity to own a luxury coastal retreat while building lasting generational wealth through an exceptional income-producing opportunity. Offered turnkey furnished, this stunning residence seamlessly combines refined beachfront living with an impressive history of high-performing short-term rental revenue. Thoughtfully updated with numerous recent enhancements—including new upper-level sliding glass doors—this home is designed to maximize breathtaking panoramic views of Tampa Bay and the iconic Sunshine Skyway Bridge. Expansive walls of glass flood the open-concept living and dining spaces with natural light, while floor-to-ceiling sliders lead to a spacious waterfront balcony, creating the perfect setting for entertaining or simply enjoying the serenity of the Gulf Coast lifestyle. The gourmet kitchen is beautifully appointed with shaker-style cabinetry, quartz countertops, an oversized island with seating, and premium stainless-steel appliances, including a gas range. Each of the four spacious bedroom suites serves as a private retreat, complete with its own en-suite bath and private balcony surrounded by lush tropical scenery.  Additional upgrades include refreshed tropical landscaping with exterior lighting, new ground-level outdoor furnishings, and freshly painted interior and exterior spaces. The covered poolside lounge and dining area provides the ultimate waterfront experience, just steps from the sugar-sand beaches of Anna Maria Island. In the evenings, unwind as the illuminated Skyway Bridge creates a spectacular backdrop across the bay. Beyond its timeless coastal architecture and unmatched beachfront setting, this property presents a truly remarkable investment opportunity with a proven track record and substantial rental income. The residence generated nearly $500,000 in income for 2025, with $456,000 booked in 2024 and $464,000 in 2023. Future reservations for 2026--2027 are already in place, offering immediate continuity of revenue and long-term wealth-building potential. Comprehensive rental history and future booking details for 2025-2027 are available upon request.  A rare offering that blends luxury, lifestyle, and legacy investment potential—this is beachfront ownership at its finest.

915 N Shore Drive, Anna Maria
$2,750,000
3 Beds ⋅ 5 Baths ⋅ Grande At Longboat Key SubDv. ⋅ 34228 Zip Code
Spectacular North west corner three bedroom condo with direct beachfront views at The Grande, a oasis with only 8 residences. This is Florida living at its very best! This second floor corner location has breathtaking views of the Gulf of Mexico and miles of beautiful sandy beach plus some views of Sarasota Bay and amazing sunsets. A fantastic wrapping terrace on the Gulfside offers outdoor enjoyment from the main living area and master suite. Two other terraces off the additional bedrooms with privacy and wonderful views. This true three bedroom, all with private baths, is 3260 square feet. A Gulf front gourmet kitchen with high end appliances has an adjacent family gathering area. The open plan flows from the living room area to the dining room and the floor to ceiling windows that dramatically overlook the Gulf of Mexico and beach, enhance the brightness and open feeling of this home. This home has 10 foot ceilings, and comes with a private enclosed two car garage with direct access.This Longboat location is near many outstanding restaurants and Anna Maria Island. Watch dolphins and manatees and so many Florida birds glide past your backyard. The azure waters of the Gulf of Mexico and the beach are just steps away.

4561 Gulf Of Mexico Drive Unit 202, Longboat Key
$3,890,000
Wells Sub SubDv. ⋅ 34216 Zip Code
Presenting LOT 25 a rare opportunity to secure a beautiful buildable bayfront lot on the north end of Anna Maria Island, offering sweeping unobstructed water views, Skyway bridge views and an unparalleled coastal lifestyle. Located just moments from the pristine shores of Bean Point, this property provides coveted beach access to one of the island’s most peaceful stretches of sand. This exceptional lot is ready for your dream home, and the seller is offering a custom build-to-convey option, allowing you to enjoy a seamless design-and-build experience. Create a luxury coastal retreat tailored to your style—whether modern, elevated coastal, or classic island architecture. Perfectly positioned near the beach, shops, dining, and the island’s natural beauty, this property is ideal for a full-time residence, vacation home, or high-end investment with the property zoned for nightly rentals. You do also have the option to purchase both lots 24 and 25.

837 N Shore Drive, Anna Maria