Siesta Key Homes with Key West Architectural style

Siesta Key Homes with Key West Architectural style

Welcome to Siesta Key, Florida—an enchanting barrier island renowned for its pristine beaches, vibrant sunsets, and a laid-back lifestyle that draws visitors and residents alike. Nestled in Sarasota County, Siesta Key is a tropical paradise that offers a unique blend of natural beauty and community charm. With its powdery white sands, crystal-clear waters, and an array of outdoor activities, this idyllic island is the perfect place to call home.

One of the most captivating features of Siesta Key is its architectural diversity, particularly the charming Key West style homes that dot the landscape. These homes, characterized by their bright, pastel colors, metal roofs, and inviting porches, embody the island’s relaxed coastal vibe. With their airy floor plans and abundant natural light, Key West-style residences are designed for both comfort and style, making them perfect for entertaining friends or enjoying quiet evenings with family.

Living in a Key West-style home in Siesta Key means embracing a lifestyle that celebrates the outdoors. Picture yourself sipping coffee on your front porch, surrounded by lush tropical landscaping, or hosting a sunset barbecue in your spacious backyard. The open, airy designs of these homes encourage a seamless flow between indoor and outdoor living, allowing you to fully appreciate the island’s stunning environment.

Whether you’re looking for a vacation retreat or a permanent residence, Siesta Key offers a unique opportunity to experience the best of Florida living. With its captivating homes and breathtaking surroundings, this charming island is waiting for you to discover your own piece of paradise.

Newest Siesta Key Homes with Key West Architectural style

1209 Sea Plume Way, Sarasota
$1,500,000
3 Beds ⋅ 3 Baths ⋅ Mangroves Sub The SubDv. ⋅ 34242 Zip Code
Virtually Staged. Old Florida Charm on Siesta Key's Quiet South End Hidden beneath a canopy of mature tropical trees on one of South Siesta Key's most desirable residential streets, this distinctive three-story home captures the timeless character and charm that make island living so special. Located within a small enclave of established homes where short-term vacation rentals are restricted, the neighborhood is known for its lush landscaping, beautiful waterfront residences, and authentic sense of community that has become increasingly rare on Siesta Key. Thoughtfully spread across three levels, the home blends timeless coastal architecture with modern updates. Exposed wood beams, a fireplace, and an abundance of outdoor living spaces give the residence a sense of warmth and character rarely found in newer construction. Multiple terraces provide private places to relax throughout the day, while the newly built Trex rooftop deck elevates the experience with sweeping sunset views and refreshing Gulf breezes. Offering 3 bedrooms, 3 bathrooms, a two-car garage, a newer metal roof, high-velocity HVAC system, Hardi board siding, and a generously sized fenced yard, the property strikes a balance between charm, functionality, and laid-back island living. Just a short walk to Point of Rocks, beach access, South Siesta Village, Captain Curt's, Crescent Beach Market, the Crescent Club, and other local favorites, the location places the best of Siesta Key at your doorstep. Spend your days exploring the island by bike, trolley, or on foot, with Siesta Key Beach, Turtle Beach, waterfront dining, and endless coastal activities all nearby. Whether it's a morning walk along the shore, an afternoon spent enjoying the island's vibrant beach culture, or sunset from the rooftop deck, this home is perfectly positioned to experience everything that has made Siesta Key one of Florida's most beloved destinations. Properties like this are becoming increasingly difficult to find on Siesta Key. Combining architectural character, modern improvements, walkability to the beach and dining, a large private yard, and a neighborhood centered around homeowners rather than vacation rentals, this is a rare opportunity to enjoy the authentic charm of island living on the quieter south end of the Key.

1209 Sea Plume Way, Sarasota
5334 Calle Florida, Sarasota
$1,750,000
4 Beds ⋅ 3 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
Discover a rare opportunity on Palm Island, one of Siesta Key’s most distinctive residential enclaves, where quiet island living meets exceptional access to the very best of Sarasota’s Gulf Coast lifestyle. Ideally located at 5334 Calle Florida, this custom-built residence offers privacy and character while remaining just moments from the white sands of Siesta Key Beach, the Village, boating, dining, and everything that makes this part of the island so desirable. Set on a generously sized lot and elevated approximately 10 feet above sea level, the home was thoughtfully constructed with island living in mind. The elevated Key West-inspired design provides an added sense of security, with the main residence having never experienced flooding during any storm. Inside, the home immediately makes an impression. Soaring 20-foot ceilings rise above the dramatic great room, while the open-concept design allows the kitchen, dining, and living spaces to flow naturally together. Abundant natural light and the impressive ceiling height create a bright, airy atmosphere that feels both sophisticated and relaxed. With 2,838 square feet of living space, four bedrooms, and three bathrooms, the home offers the scale and flexibility for full-time living, entertaining, or an exceptional Siesta Key retreat. The oversized primary suite provides a private escape with a custom-built window seat, two walk-in closets, and a spacious primary bath. Built-in speakers extend throughout the residence and onto the back porch, creating a seamless atmosphere for everyday living and entertaining. Outdoor living is equally impressive. The elevated heated pool and hot tub create a private resort-like setting complemented by an outdoor shower and generous areas for relaxing or gathering with friends and family. Thoughtful exterior details include landscape lighting and electrical power in the soffits for seasonal or year-round accent lighting. The home is also well equipped for coastal living with three-zone air conditioning, hurricane-rated Kevlar screens, a hurricane-rated front door and garage door, and a spacious two-car garage with ample storage. Recent improvements include a new roof in 2021, pool resurfacing in 2024, pool cage repainting and rescreening in 2025, and a new water heater in 2025. What truly sets 5334 Calle Florida apart is the combination of location and architecture: a custom, elevated residence with dramatic ceiling heights and open living spaces, tucked away on Palm Island yet remarkably close to the beach and Siesta Key lifestyle. It is a distinctive opportunity to enjoy privacy, elevation, and luxury in one of Sarasota’s most sought-after island settings.

5334 Calle Florida, Sarasota
4114 Roberts Point Circle, Sarasota
$995,000
4 Beds ⋅ 3 Baths ⋅ Roberts Point SubDv. ⋅ 34242 Zip Code
Reduced $155,000! This is the lowest-priced waterfront property on Siesta Key. Set along a quiet bayou in Roberts Point, one of North Siesta Key’s most coveted and established neighborhoods, this well-cared-for waterfront residence offers an appealing combination of immediate livability, flexible space and exceptional future potential. Enjoy the home as it is, thoughtfully update it over time or create an entirely new island retreat among the neighborhood’s impressive luxury residences. The primary living spaces are positioned on the upper level, where vaulted ceilings and an open layout create a bright, comfortable setting for everyday living and entertaining. Multiple decks extend the living areas outdoors, offering peaceful views of the water and surrounding tropical landscape. A hot tub overlooking the bayou provides a relaxing place to unwind at the end of the day. The legal ground level (non-conforming) adds valuable versatility with a private bedroom and bath, bonus room, screened lanai and two-car garage, well suited for guests, extended family, a home office or a recreational space. A new roof completed in August 2023, hurricane shutters and completed storm remediation provide added peace of mind. The property offers direct water access to Sarasota Bay for watercraft, kayaks and paddleboards, making it easy to enjoy Siesta Key’s natural surroundings from your own backyard. Ideally located near Siesta Beach, Siesta Village, shopping, dining, and entertainment, and easy access to mainland Sarasota, this is a distinctive opportunity to live, renovate or rebuild in a coveted North Siesta Key setting.

4114 Roberts Point Circle, Sarasota
6901 Bochi Circle, Sarasota
$2,675,000
4 Beds ⋅ 4 Baths ⋅ Coronas Park SubDv. ⋅ 34242 Zip Code
Under Construction. Discover La Linda, an exclusive collection of eight custom-built, modern homes offering breathtaking Gulf views just off Ocean Boulevard. Nestled in the highly sought- after Siesta Key, these elevated residences are crafted to the highest standards, featuring solid block construction on all levels, impact-resistant windows and doors, and private elevators for ultimate safety, security, and convenience. Perfectly situated, La Linda is just 5 minutes from Siesta Village and 8 minutes from the world-famous, sugar sands of Siesta Key Beach, providing the ideal balance of privacy and accessibility. Each four- bedroom, fourand-a-half-bathroom home is a masterpiece of refined design, boasting luxury finishes, impeccable craftsmanship, and modern aesthetics throughout. Designed for Comfort, Elegance & Entertainment - First Level: A spacious four-car garage leads to a beautifully designed lanai and pool deck, creating a private outdoor retreat. Second Level: The serene primary suite features a walk-in closet and spa-like bathroom with a freestanding tub, frameless glass shower, and double vanity. Two additional guest bedrooms, and additional living space, balcony access, and a dedicated laundry room complete this level. Third Level: The heart of the home, the open-concept great room, is designed for seamless indooroutdoor living. High ceilings and wraparound balconies maximize the Gulf views, while the chef’s kitchen impresses with a premium Viking appliance package, solid wood cabinetry, and stunning Calacatta Quartz countertops. A guest suite/office adds versatility to the space. Step outside to your own private oasis, where lush landscaping surrounds a sparkling pool and patio area—ideal for relaxation or entertaining. With its prime location, unparalleled craftsmanship, and luxury amenities, La Linda offers an exceptional opportunity to own a modern coastal masterpiece on Siesta Key. Don’t miss your chance to experience the pinnacle of island living—schedule your private tour today!

6901 Bochi Circle, Sarasota
6907 Bochi Circle, Sarasota
$2,800,000
4 Beds ⋅ 5 Baths ⋅ Coronas Park SubDv. ⋅ 34242 Zip Code
Under Construction. Discover La Linda, an exclusive collection of eight custom-built, modern homes offering breathtaking Gulf views just off Ocean Boulevard. Nestled in the highly sought-after Siesta Key, these elevated residences are crafted to the highest standards, featuring solid block construction on all levels, impact-resistant windows and doors, and private elevators for ultimate safety, security, and convenience. Perfectly situated, La Linda is just 5 minutes from Siesta Village and 8 minutes from the world-famous, sugar-white sands of Siesta Key Beach, providing the ideal balance of privacy and accessibility. Each four-bedroom, four- and-a-half-bathroom home is a masterpiece of sophisticated design, boasting luxury finishes, impeccable craftsmanship, and modern aesthetics throughout. Designed for Comfort, Elegance & Entertainment - First Level: A spacious four-car garage leads to a beautifully designed lanai and pool deck, creating a private outdoor retreat. Second Level: The serene primary suite features a walk-in closet and spa-like bathroom with a freestanding tub, frameless glass shower, and double vanity. Two additional guest bedrooms, and additional living space, balcony access, and a dedicated laundry room complete this level. Third Level: The heart of the home, the open-concept great room, is designed for seamless indoor- outdoor living. High ceilings and wraparound balconies maximize the Gulf views, while the chef’s kitchen impresses with a premium Viking appliance package, solid wood cabinetry, and stunning Calacatta Quartz countertops. A guest suite/office adds versatility to the space. Step outside to your own private oasis, where lush landscaping surrounds a sparkling pool and patio area—ideal for relaxation or entertaining. With its prime location, unparalleled craftsmanship, and luxury amenities, La Linda offers an exceptional opportunity to own a modern coastal masterpiece on Siesta Key. Don’t miss your chance to experience the pinnacle of island living—schedule your private tour today!

6907 Bochi Circle, Sarasota
3750 Bayou Louise Lane, Sarasota
$12,900,000
5 Beds ⋅ 7 Baths ⋅ Phillippi Shores SubDv. ⋅ 34242 Zip Code
Tucked on the coveted north end of Siesta Key, this extraordinary double-lot point estate is positioned at the tip of a protected peninsula, offering panoramic water views and unforgettable sunsets. Surrounded by water and set directly across from protected parkland, the setting feels like your own private island. The property features three separate structures: a main residence, a guest house, and a separate waterfront cabana with bath. In total, the compound offers six bedrooms and six bathrooms, with gourmet kitchens in both the main house and guest house — each outfitted with high-end appliances throughout — ideal for multigenerational living, guest accommodations, or an exceptional private retreat. Throughout both residences, the finish detail is exceptional. Designer-selected materials create a cohesive and elevated aesthetic carried seamlessly across the entire compound. Custom wood flooring with intricate stone inlays, handcrafted stairwells featuring wood and stone risers, extensive crown molding, and refined architectural millwork highlight the level of craftsmanship invested in every space. Specialty stonework and thoughtfully curated finishes blend warmth with sophistication, creating interiors that feel timeless, substantial, and unmistakably high-end. Outdoor living is nothing short of spectacular. A dramatic infinity-edge pool with swim-assist system overlooks the water, enhanced by a striking waterfall feature that spills elegantly into the pool. New pool equipment (2025) supports the system. Natural rock waterfront frontage and a sculptural rock formation lead down to the shoreline, creating a one-of-a-kind coastal backdrop. Two docks serve the property — one with a double lift — offering outstanding boating access and rare protection on both sides of the point, with additional lift capacity for multiple watercraft. An outdoor shower provides added convenience after boating or swimming. Perched at the edge of the peninsula, the waterfront cabana and adjacent hot tub create a private, spa-like retreat suspended over the water — an unforgettable setting to take in sweeping sunset views. The residences were renovated separately: main house (2009) and guest house (2012). All A/C units have been renewed recently, along with the electric unit, and a new transformer (2024) services both properties. Sonos surround sound extends throughout all structures. Located on the highly desirable north end of Siesta Key, the estate offers convenient on-and-off island access while remaining just minutes from Southside Village and downtown Sarasota.

3750 Bayou Louise Lane, Sarasota
6732 Sarasea Circle Unit 104C, Sarasota
$639,900
2 Beds ⋅ 2 Baths ⋅ Siesta SubDv. ⋅ 34242 Zip Code
Reduced over 60K! Excellent resort investment opportunity with a proven rental history at The Beach Club on Siesta Key, located just steps from the world-famous sugar-sand beach. This beautifully maintained residence looks and feels brand new, featuring a functional floor plan, deeded beach access, and a complete 2021 update with elegant sea-inspired décor, flat-screen TVs, free Wi-Fi, and a full kitchen with stainless steel appliances. Owners enjoy up to 120 days of personal use per year while benefiting from professional on-site management or the option to self-manage for added flexibility. TripAdvisor rates the property 4.5 stars with outstanding reviews. Resort amenities include a heated pool, hot tub, and complimentary beach chairs and umbrellas. Built in 2009 on stem walls, the building is elevated and sustained no storm damage. Ideally located mid-island just 1,000 feet south of the Stickney Point Bridge for easy mainland access, and within walking distance to popular restaurants, shops, marinas, rentals, and local favorites such as Captain Curt’s and Daiquiri Deck—making this a true turnkey beach getaway and income-producing investment. Ask your agent for the Rental History attached to the MLS listing too!

6732 Sarasea Circle Unit 104C, Sarasota
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