Siesta Key Homes with Florida Architectural style

Siesta Key Homes with Florida Architectural style

Welcome to Siesta Key, Florida, a stunning barrier island located in Sarasota County, renowned for its pristine beaches, vibrant culture, and charming coastal lifestyle. With its powdery white sands, Siesta Key Beach consistently ranks among the best beaches in the United States, offering residents and visitors alike a serene escape to sun-soaked shores and azure waters.

Siesta Key is not just a beach lover's paradise; it’s a community where the laid-back island vibe meets modern conveniences. The island boasts an array of dining options, from casual beachside cafes to upscale restaurants, ensuring there's something to satisfy every palate. Explore local boutiques, art galleries, and markets that reflect the unique character of this coastal gem.

When it comes to real estate, Siesta Key offers a diverse selection of homes, many of which embody the enchanting Florida architectural style. Picture charming beach cottages, elegant waterfront estates, and contemporary condos, all designed to harmonize with the island's natural beauty. These homes often feature open floor plans, expansive windows, and outdoor living spaces that invite the Florida sunshine in. Whether you're seeking a cozy retreat or a luxurious waterfront property, Siesta Key has something to fit your lifestyle.

Living in Siesta Key means embracing a vibrant community centered around outdoor activities, cultural events, and a relaxed pace of life. With its stunning scenery and welcoming atmosphere, it’s no wonder that Siesta Key is a sought-after destination for both homebuyers and vacationers. Discover your piece of paradise today!

Newest Siesta Key Homes with Florida Architectural style

1300 N Portofino Drive Unit 102, Sarasota
$449,995
2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
THE SIESTA KEY LIFESTYLE, ALL IN ONE EXCEPTIONAL WATERFRONT COMMUNITY! Imagine starting your day with coffee overlooking a picturesque harbor, spending the afternoon with your toes in Siesta Key’s powdery white sand, and gathering with friends for sunset cocktails as another spectacular Florida day draws to a close. Welcome to Siesta Harbor Condominiums Association, a vibrant 55+ community where boating, beach days, and an inviting social scene come together in one extraordinary island setting. DIRECT WATERFRONT LIVING! Perfectly positioned on the ground floor, this beautifully updated, fully furnished 2-bedroom, 2-bath residence feels more like a private coastal home than a condo. Forget elevators and stairs - simply walk through your front door with groceries or beach bags and you’re home! Inside, a bright, breezy interior features attractive tile floors throughout and an open layout designed for easy entertaining. The remodeled kitchen is a showpiece, with gorgeous granite countertops, crisp white cabinetry, stainless steel appliances, a stylish glass backsplash, a generous breakfast bar opening to the living room, and the everyday luxury of a KITCHEN PANTRY—all with gorgeous views of the harbor! The living room flows into a spectacular glass-enclosed lanai, where walls of impact-resistant glass sliders frame intimate views of the harbor, lush tropical grounds, and boats gently resting along the waterway just beyond your windows. Imagine lingering here with a good book, watching the boats drift by, or savoring an evening cocktail in your own waterfront retreat. Two welcoming bedrooms include a flexible guest room with a Murphy bed, ideal for visitors or a home office. Updated bathrooms include a bidet toilet in the primary suite. Impact glass, tasteful furnishings, a private LOCKED STORAGE CAGE just down the hall, and on-site laundry and covered parking are welcome perks. Beyond your front door, the Florida lifestyle unfolds! Boaters will love the harbor's DIRECT INTRACOASTAL WATERWAY ACCESS WITH NO BRIDGES, situated just north of the South Bridge no-wake zone for convenient cruises south toward Venice. Imagine stepping aboard your boat just outside your home and setting off for a day on the water (slips subject to availability). Beach lovers will treasure DEEDED BEACH ACCESS directly across the street at Crescent Arms, opening the door to Siesta Key’s world-famous white quartz sand and sparkling Gulf waters. Spend sun-drenched afternoons by the community pool, relax in the hot tub, or enjoy the clubhouse, fitness center, library, billiards, and lively social activities. One of Siesta Harbor’s most cherished traditions is sunset happy hour on the waterfront sunset deck, where neighbors gather to toast another beautiful evening in paradise. Tucked into a peaceful waterfront setting, Siesta Harbor is just moments from South Siesta Key Village, with its grocery store, restaurants, bars, and charming boutiques. The nearby South Bridge makes mainland Sarasota wonderfully accessible, while the Breeze transit stops right in front of the clubhouse for a convenient way to explore the island. Whether your perfect day means cruising the Intracoastal, strolling the beach, sharing sunset cocktails, or simply relaxing beside the water, this is more than a condominium—it’s your invitation to live the SIESTA KEY LIFESTYLE you’ve always imagined! WHERE ELSE can you enjoy waterfront living and resort-style amenities under $500K on Siesta Key?

1300 N Portofino Drive Unit 102, Sarasota

5215 Calle De Costa Rica, Sarasota
$1,175,000
4 Beds ⋅ 3 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
LOCATION AND CHARM!!! Welcome to 5215 Calle De Costa Rica, a single-family home located in Siesta Key, FL just steps away from the highly desired Siesta Key Beach and Village. This charming cottage offers an unbeatable location along with 1,762 square feet of living space featuring 3 bedrooms and 2 bathrooms. The main house can have one interior door closed which creates a private mother-in-law suite with its own exterior entrance. In addition to the main house there is a quaint separate guest house that offers ample space for family and friends, an office or a creative space as a studio. The entire property is fenced and feels like its own private oasis surrounded by lush tropical landscaping and generous private outdoor spaces with brick paths and patios to enjoy your morning coffee or relax in a fabulous serene environment. Inside this 6-room property you will find luxury custom ceramic tile throughout and tongue-and-groove walls and ceilings. The many windows allow in plenty of gorgeous natural light, making every room bright and welcoming. New HVAC in main house in 2024 as well as kitchen flooring. You will also appreciate the quiet street where neighbors often gather while walking their dogs while being only 5 blocks to shopping, dining and the fantastic nightlife that Siesta Key Village offers. Just a half mile walk to Sunset Pier or Beach Access #7 and the powdery quartz sands of the top-rated Siesta Key Beach. This home is perfect as a primary residence, a vacation/second home or a fabulous opportunity as an investment property. Don't miss the opportunity to own this rare and special Siesta Key Cottage located in the most coveted of locations. Bring your bikes and beach chairs because this home offers endless possibilities and the Siesta Key lifestyle offers so much to be explored and enjoyed!!

5215 Calle De Costa Rica, Sarasota

5780 Midnight Pass Road Unit 301, Sarasota
$1,500,000
2 Beds ⋅ 3 Baths ⋅ Gulf & Bay Club SubDv. ⋅ 34242 Zip Code
There is something special about a place where the walk to the beach is nearly as beautiful as the beach itself. Welcome to Gulf & Bay Club, one of Siesta Key's most distinctive beachfront communities, where lush tropical landscaping, winding pathways, islands surrounded by freshwater lagoons, and beautifully manicured grounds create a resort-like atmosphere that feels worlds away from the everyday. Positioned in Building B, just one building removed from the Gulf, this exceptional end-unit residence offers a perspective that is uniquely its own. Expansive windows capture abundant natural light and unparalleled views across the community's picturesque grounds, while the northwest exposure welcomes the warm glow of Siesta Key’s legendary sunsets. One of only 14 residences featuring this generously proportioned two-bedroom, two-bath floor plan, Unit 301 offers the space and flexibility to truly settle into island living. Inside, a comfortable coastal aesthetic creates an inviting backdrop for relaxed days and easy entertaining. Luxury vinyl plank flooring flows throughout, providing a handsome, low-maintenance foundation ideal for beachfront living. The kitchen features ivory cabinetry, solid-surface countertops, generous workspace, and smart stainless appliances, while beautifully updated bathrooms offer crisp white cabinetry, abundant storageand contemporary frameless glass showers. An enclosed lanai extends the living area, creating a wonderful setting to enjoy the surrounding views in year-round comfort. Beyond your front door, Gulf & Bay Club delivers an exceptional collection of amenities, including an incomparable 800 feet of private beach access, swimming pools, state of the art fitness facilities, tennis and pickleball courts, beautifully maintained gathering spaces, and an organized social calendar. With convenient access to both the shoreline and the community's recreational amenities, this residence offers an appealing balance of activity and tranquility. Spacious, welcoming and wonderfully positioned, this is an opportunity to experience Siesta Key from a perspective that is every bit as memorable as Siesta Key itself

5780 Midnight Pass Road Unit 301, Sarasota

1140 Windsong Lane Unit A, Sarasota
$3,995,000
5 Beds ⋅ 7 Baths ⋅ 1140 Windsong Lane Land Condo SubDv. ⋅ 34242 Zip Code
What if your next luxury vacation home could be just as rewarding when you're away as when you're enjoying it yourself? Welcome to Blue Lagoon, an ultra-high-performing short-term luxury vacation rental on Siesta Key, purpose-built to deliver the best of both worlds: an extraordinary private coastal retreat and a compelling income-producing asset. Your home. Your schedule. Your decision. Built in 2024 and offered turnkey furnished, this five-bedroom, seven-bath residence delivers 3,891 square feet of sophisticated coastal living, with beautifully curated interiors, an expansive gathering kitchen, five en-suite bedrooms, private elevator, and multiple terraces overlooking the island. But the real magic? Step outside. A spectacular private lagoon awaits, complete with a rock waterfall, waterslide, rope swing, jumping platform, and heated saltwater pool, accompanied by outdoor entertaining spaces, miniature golf, and bocce. Above it all, a rooftop terrace captures Gulf views, while deeded beach access places Siesta Key's celebrated shoreline just moments away. Part of Vunique's distinctive collection of luxury vacation homes, Blue Lagoon combines commercial-grade durability with residential sophistication, engineered for the demands of luxury vacation rental performance without compromising the pleasures of private ownership. Enjoy it exclusively, capitalize on its rental potential, or find your own balance between the two. An exceptional lifestyle. A compelling investment. Entirely your decision.

1140 Windsong Lane Unit A, Sarasota

9000 Blind Pass Road Unit B307, Sarasota
$895,000
2 Beds ⋅ 2 Baths ⋅ Fishermans Cove SubDv. ⋅ 34242 Zip Code
Come and see why Fisherman’s Cove is one of the most highly desirable communities on Siesta Key! This is one of the only complexes in which direct beachfront living also offers the boating lifestyle right out the back door! Discover an exceptional opportunity to own a top-floor 2-bedroom, 2-bath condominium offering 1090 square feet of coastal living, complete with an enclosed lanai showcasing breathtaking direct Gulf views and spectacular sunsets. One of the residence’s stunning features are new impact resistant glass sliders with in the lanai, an upgrade that beautifully captures the panoramic water views while allowing abundant natural light to fill the living space. Inside, the residence features attractive laminate flooring with sound-buffered installation throughout, light and bright colors and a spacious walk-in closet with a washer and dryer- very rare for a condominium. Offered turnkey furnished, this condominium is ready to enjoy as a full-time residence, private beach retreat, or investment property as WEEKLY RENTALS ARE ALLOWED! Newer HVAC and water heater are also a huge bonus. Beyond its incredible beachfront setting, Fisherman’s Cove offers a unique combination of Gulf-front living and boating convenience, featuring direct Gulf frontage and access to the Intracoastal Waterway. Residents enjoy approximately 900 feet of beautiful sandy beach, gated access, a heated community pool, kayak storage and dock, fishing from the community docks, and 40 boat slips available to owners and renters at no additional charge. Additional conveniences include elevator access, assigned parking, ample guest parking, storage, on-site management and rental office, and gas grilling areas along the picturesque lagoon. Experience the best of Siesta Key living with breathtaking Gulf sunsets, private beachfront access, exceptional boating amenities, and a welcoming waterfront community. An outstanding opportunity to own your very own piece of paradise!

9000 Blind Pass Road Unit B307, Sarasota

925 Beach Road Unit 208, Sarasota
$565,000
2 Beds ⋅ 1 Baths ⋅ La Siesta SubDv. ⋅ 34242 Zip Code
Enjoy the island lifestyle at La Siesta, ideally located directly across from world-famous Siesta Key Beach! This inviting, turnkey-furnished, two-bedroom, second-floor condominium is situated in highly desirable Building B, known for its close proximity to the beach. With a 7-day minimum rental policy and convenient on-site rental management, La Siesta offers the best of both worlds, your own beach getaway with the added benefit of generating rental income when you're not enjoying it yourself! Thoughtful recent improvements include new carpeting (2026), a beautifully resurfaced lanai (2026), a new air conditioning system and water heater (2025), an updated electrical panel (2024), and newer appliances (2024). The kitchen was also renovated by a previous owner. The private screened-in lanai provides a wonderful space to relax and unwind while enjoying the refreshing coastal breezes. Adding even more appeal, La Siesta has benefited from recent community-wide improvements, including exterior painting (2026), further enhancing this desirable beachside destination. Residents and guests enjoy an array of resort-style amenities, including a heated community pool, fitness center, clubhouse, grilling areas, and convenient on-site laundry facilities. In addition, the condominium includes one assigned carport parking space and a storage locker for your beach toys. Enjoy the ultimate peace of mind, whether you live near or far, with professional on-site management handling everything from cleaning and guest check-ins and check-outs to responsive maintenance and everyday needs, you can enjoy the benefits of ownership without the day-to-day responsibilities. Just across the street, you'll love the powdery white sands and breathtaking sunsets of Siesta Key Beach! You're also close to the charming boutiques, restaurants, and entertainment of Siesta Key Village, with convenient access to the mainland via the Stickney Point Bridge plus a free trolley that stops in front of La Siesta to get you anywhere on the island. This exceptional location puts the best of island living right at your fingertips. Whether you're seeking your own coastal escape or an opportunity to generate rental income, this well-maintained condominium offers the perfect combination. Your slice of Siesta Key paradise awaits!

925 Beach Road Unit 208, Sarasota

8900 Blind Pass Road Unit A303, Sarasota
$799,900
1 Beds ⋅ 1 Baths ⋅ Fishermans Cove SubDv. ⋅ 34242 Zip Code
Top-floor, turnkey beachfront living with your own assigned boat slip—experience the best of both worlds on the quiet southern end of world-renowned Siesta Key in Sarasota, Florida. Breathtaking Gulf views greet you from every room of this beautifully remodeled 1-bedroom, 1-bathroom condo, where tranquil turquoise waters and a beachfront setting create an extraordinary coastal retreat. An enclosed patio with hurricane-impact windows offers a cruise-ship-like perspective over the Gulf. Open the windows to welcome coastal breezes and the soothing sound of waves along the shore. With the Gulf on one side and Blind Pass Lagoon on the other, enjoy both sunrise and sunset, sand between your toes, and boating adventures from your assigned slip. Launch a kayak or paddleboard to explore the waterways, or head out by boat toward Sarasota Bay and the open Gulf with no bridges along the way. Thoughtfully remodeled throughout, the interior features ceramic wood-look tile, soft coastal colors, updated fans and light fixtures, and an open floor plan designed to showcase the views. The beautifully renovated kitchen features granite countertops, custom wood cabinetry with soft-close doors, a tile backsplash, and stainless steel appliances. An opened kitchen wall enhances sightlines, while an additional glass door brings in views of Blind Pass Lagoon, where wildlife, kayakers, and boaters provide an ever-changing backdrop. Beautifully appointed furnishings complement inviting spaces for dining and entertaining, including a kitchen breakfast bar, a full dining area, and additional dining space on the enclosed patio. Thoughtful furniture with built-in storage and an additional interior closet provide room for beach essentials. Wake to water views in the primary bedroom, complete with an expansive walk-in closet housing a full-size washer and dryer—a rare convenience in this community for owners and renters alike. The thoughtfully renovated bathroom features a glass-enclosed walk-in shower, an updated vanity with a granite countertop, and updated lighting. Additional highlights include air conditioning updated in 2023 and a new building roof in 2025. Monthly fees include water, sewer, internet, and cable. Enjoy long beach walks, a heated community swimming pool, boating, kayaking, and fishing—all at your fingertips. Walk to waterfront dining at Turtles Restaurant and Ophelia’s on the Bay, or take the free trolley to Siesta Key Village for dining, live entertainment, and charming shops. Discover downtown Sarasota’s cultural offerings, including ballet, symphony performances, the Van Wezel Performing Arts Hall, and the farmers market, with convenient access to Sarasota Bradenton International Airport. Whether you seek a turnkey beachfront escape, an investment opportunity with one-week minimum rentals, or a full-time coastal residence, this exceptional Fishermans Cove condo brings together beachfront beauty and a bonus boating lifestyle if desired!

8900 Blind Pass Road Unit A303, Sarasota

3458 Anglin Drive, Sarasota
$2,495,000
4 Beds ⋅ 3 Baths ⋅ Bay Island Park SubDv. ⋅ 34242 Zip Code
Located in the highly desirable Bay Island neighborhood, this beautifully updated, move-in-ready Key West-style residence offers an appealing combination of privacy, space, and convenience. Known as the "Gateway to Siesta Key," Bay Island enjoys a prime location near the north bridge, providing easy access to Siesta Key's beaches and village, as well as downtown Sarasota's dining, shopping, and cultural attractions. Set on an expansive 14,400-square-foot double lot—an uncommon offering on Siesta Key—the property is surrounded by mature tropical landscaping, creating a private setting with generous outdoor living spaces. The home's open floor plan features vaulted ceilings, abundant natural light, and a natural gas fireplace. French doors connect the main living areas to multiple covered terraces, extending the living space outdoors. The kitchen features a large quartzite island, custom cabinetry, generous storage, and a full suite of Thermador appliances. The primary suite is located on the main living level, along with a flexible fourth bedroom or den. On the third floor, two spacious guest bedrooms share a newly renovated bathroom and enjoy access to an elevated terrace. Outdoor amenities include a heated saltwater pool, travertine decking, an outdoor shower, and ample space for relaxing or entertaining within the landscaped grounds. Extensively renovated in 2019 and further improved in subsequent years, the home features updated major systems, hurricane-rated windows and French doors, retractable screens, whole-house water filtration, and additional upgrades. Meticulously maintained and move-in ready, this Bay Island property offers an uncommon combination of lot size, privacy, location, and updated living spaces on Siesta Key.

3458 Anglin Drive, Sarasota

7535 Midnight Pass Road, Sarasota
$4,500,000
5 Beds ⋅ 2 Baths ⋅ Sub Of Us Lt 7 Of 20-37-18 SubDv. ⋅ 34242 Zip Code
For the first time since 1925, the same Sarasota family is bringing 7535 and 7539 Midnight Pass Road to market, offered together as nearly one acre on Siesta Key. The two parcels total 0.95 acres, with 7535 offering over 100 feet of direct waterfrontage on Little Sarasota Bay, a reinforced concrete seawall, and access to the Intracoastal Waterway. The main home was designed by Jack West, a celebrated architect of the Sarasota School of Architecture. The charming second home on the adjoining parcel was designed by his onetime partner, Elizabeth Boylston, the first woman in Florida elected to the American Institute of Architects. This second residence offers two bedrooms, one bathroom, and 1,016 square feet, in addition to the MLS-listed totals. A detached two-car garage provides additional parking and storage. Walls of sliding glass and graceful midcentury lines open the main house to the garden and the water. Framed by lush tropical greenery, the combined site presents a rare opportunity to create a waterfront compound with a main residence, guest house and gardens. An additional adjacent 0.53-acre lot may also be available for purchase at an additional price, offering an opportunity to expand the property even further. A 2016 dock with a 13,000 lb boat lift provides access to the Intracoastal Waterway, where mornings begin with soft golden light over Little Sarasota Bay. Turtle Beach, Crescent Beach, and the powder-soft white sand of Siesta Beach are minutes away, with Siesta Key Village, downtown Sarasota, and Sarasota Bradenton International Airport all within easy reach. For the buyer who has been waiting for the right piece of Siesta Key, this is it: nearly an acre of land with direct bayfrontage, a seawall, dock and lift already in place, complemented by an architectural legacy and history that cannot be replicated. Create the waterfront home you have always imagined on land that has been cherished by the same family for over a century and is now ready for its next chapter.

7535 Midnight Pass Road, Sarasota

5376 Shadow Lawn Drive, Sarasota
$2,400,000
5 Beds ⋅ 5 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code
Some homes on Siesta Key are about the beach. Others are about boating. This one lets you have both. Set along a protected canal with direct boating access to Sarasota Bay through the Grand Canal, and from there to the Intracoastal Waterway and the Gulf, this Siesta Key waterfront home is made for the way life is meant to be lived. Take the boat out for the morning, launch a kayak or paddleboard from your own waterfront, spend some time at Siesta Key Beach, then come home to your private saltwater pool, outdoor kitchen and quiet canal view. The important updates are already here too: a 2021 reroof, impact windows and sliders installed in 2022, plus new first floor flooring, fresh interior paint, a luxury renovation of the first floor primary bath, an outdoor kitchen and waterfront pavers, all completed in 2026. Plantation shutters finish every window and slider. At the center of the home, a fully screened courtyard lanai with a tabletop fire pit extends the living space. Seven impact sliders connect several rooms directly to the courtyard, filling the home with natural light and creating an easy indoor outdoor flow toward the pool and waterfront. Additional sliders from the flex room open toward the pool. The home and pool sustained no storm damage during the 2024 storms. If you haven’t dropped anchor yet, wait until you see the two amazing primary suites. The first floor primary offers courtyard access, two walk in closets and a beautifully renovated 2026 ensuite bath with upscale finishes. Upstairs, the entire second level becomes a private retreat with canal views, a spacious bath, two more walk in closets and its own waterfront balcony. One closet is so large you may wonder if it could qualify as a New York City apartment. When it is time for a little quiet, open the sliders and take in sunset over the canal, or start your morning with fresh air and coffee on the balcony. A redesigned media and flex area now includes an additional bedroom while preserving an approximately 424 square foot flex room for a media room, gym, game room or lounge. Another bedroom includes a Murphy bed and built in desk, making it an easy guest room, home office or both. Outside is where this home really earns its Siesta Key address. The private saltwater pool is surrounded by tropical landscaping and spaces for relaxing, dining and entertaining. The seawall, bulkhead and davits were replaced in 2021, with the waterfront setup planned around a 45 foot Sea Ray. This is a home for boaters who want to use the water, not simply look at it. Set in the heart of Siesta Key, the home is just minutes from Siesta Key Beach, named the No. 1 in the U.S. for 2026 and recognized among the nation’s best many times over. Known for its powdery quartz sand and Gulf waters, it is one of the reasons living here is so special. Siesta Key Village is close by for restaurants, bars, live music and boutiques. Sarasota is just beyond the North Bridge, with downtown waterfront dining, shopping, galleries, theaters, performing arts and cultural attractions close at hand. Whether you are looking for a full time Siesta Key waterfront home or a second home for family and friends, 5376 Shadow Lawn Drive offers true boating access, a private saltwater pool, substantial updates, flexible living space and an exceptional island location. This is the kind of home where every day can include the beach, the boat and dinner by the pool. That is a pretty wonderful way to live.

5376 Shadow Lawn Drive, Sarasota

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