Siesta Key Homes with Florida Architectural style

Siesta Key Homes with Florida Architectural style

Welcome to Siesta Key, Florida – a sun-kissed paradise nestled in Sarasota County that epitomizes coastal living at its finest. Renowned for its powdery white sands and crystal-clear waters, Siesta Key is not just a destination; it’s a lifestyle. This charming barrier island boasts a vibrant community where the laid-back atmosphere invites you to unwind and embrace the beauty of nature.

Siesta Key’s homes reflect the alluring Florida architectural style, characterized by open floor plans, spacious verandas, and bright, airy spaces that seamlessly blend indoor and outdoor living. Whether you're captivated by the classic coastal cottages or the luxurious beachfront estates, each property is designed to maximize the stunning views and gentle breezes that define this idyllic locale. Imagine sipping your morning coffee on a sun-drenched patio or hosting sunset gatherings in your beautifully landscaped backyard.

The community is rich with amenities, from boutique shops and gourmet dining to vibrant nightlife and cultural attractions. The nearby Siesta Key Village offers a delightful mix of local charm and modern conveniences, making it easy to indulge in everything this enchanting area has to offer.

With year-round sunshine and a welcoming atmosphere, Siesta Key is the perfect place to call home. Whether you’re looking for a vacation retreat or a permanent residence, the homes here embody the essence of Florida living, inviting you to create lasting memories in a setting that feels like a dream. Come discover your slice of paradise on Siesta Key!

Newest Siesta Key Homes with Florida Architectural style

4938 Commonwealth Drive, Sarasota
$2,650,000
4 Beds ⋅ 4 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Exceptional luxury coastal living on Siesta Key! Positioned on Siesta Key’s Grand Canal with quick access to Sarasota Bay, this fully renovated estate offers the perfect blend of high-end comfort and modern efficiency. Powered by solar panels with battery storage, this eco-conscious home delivers peace of mind and low utility costs. The sprawling open floor plan highlights a newly integrated primary guest suite and seamless indoor-outdoor flow opening to a resort-style heated cocktail pool and spa. A standout feature is the expansive, grandfathered 1,300 sq. ft. bonus space—providing endless possibilities for a game room, home gym, or customized lounge. Complete with high-end boating amenities and located just minutes from world-famous Siesta Key Beach and Village. Move-in ready perfection!

4938 Commonwealth Drive, Sarasota
6910 Midnight Pass Road, Sarasota
$5,400,000
10 Beds ⋅ 14 Baths ⋅ Point Of Rocks Terrace SubDv. ⋅ 34242 Zip Code
TWO LUXURY RESIDENCES. ONE SIESTA KEY ESTATE. OVER HALF A MILLION IN 2025 GROSS RENTAL REVENUE. Rent them. Keep them for yourself. Or enjoy the best of both worlds. Welcome to 6910 Midnight Pass Road, where luxury coastal living meets proven investment performance at less than 10× GRM. Just moments from Crescent Beach and iconic Point of Rocks, this remarkable offering features ten bedrooms, fourteen bathrooms, 5,767 square feet of living space, private elevators, resort-style pools and spas, and expansive indoor-outdoor entertaining spaces. Purpose-built as luxury short-term vacation rentals, both residences blend sophisticated coastal design with commercial-grade durability and resort-level amenities. Built for memories. Engineered for performance. With historical average daily rental rates exceeding $1,000, approximately 250 booked nights annually per residence, and potential STR-related tax strategies worth exploring with your tax advisor, this is more than a vacation home. It's an asset with options. Currently configured as two separately titled condominium residences, offered together as a single purchase. Financial performance and rental history available upon request

6910 Midnight Pass Road, 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
5950 Midnight Pass Road Unit 101, Sarasota
$485,999
1 Beds ⋅ 1 Baths ⋅ Siesta Beach House SubDv. ⋅ 34242 Zip Code
An exceptional opportunity to own a beautifully updated and turn-key beach condominium in the heart of Siesta Key, offering the flexibility of a strong rental investment, seasonal getaway, or your own private coastal retreat. Built a solid foundation of bookings into February and March bookings. Repeat Guests and higher demand! Located within Siesta Beach House this residence places you just a short walk to both Siesta Beach and Crescent Beach, while also offering the rare advantage of private beach access exclusively for residents and guests. Inside, the condo has been thoughtfully upgraded and meticulously maintained, creating a bright and modern coastal atmosphere. The kitchen features quartz countertops, ceramic tile backsplash, under-cabinet lighting, stainless steel appliances, and solid wood cabinetry, all opening seamlessly into the main living space. Porcelain ceramic tile flooring runs throughout, enhancing the clean, beach-inspired feel of the home. Additional improvements provide peace of mind and long-term value, including a new elevated A/C system installed in 2024 and a brand-new electrical panel completed in 2025. Beautiful upgraded baseboards in the living room, extra hallway storage, and tasteful finishes throughout further separate this condo from many others currently available on the island. The spacious bedroom includes a walk-in closet, while the open-concept floor plan maximizes functionality and comfort within the space. Being sold fully furnished and turnkey, this property is truly ready for immediate enjoyment or rental use. The Siesta Beach House community offers a community pool and direct private beach access, all within a highly desirable location. With a flexible minimum lease period of just 3 days, this property also presents excellent income-producing potential for investors seeking short-term rental opportunities. Whether you are searching for a beachside investment property, a lock-and-leave vacation home, or a cozy private condominium steps from world-renowned beaches, this Siesta Key opportunity delivers exceptional lifestyle and value in one of Sarasota’s most sought-after coastal destinations. Schedule your private showing today and experience the island lifestyle firsthand.

5950 Midnight Pass Road Unit 101, Sarasota
6020 Midnight Pass Road Unit 61, Sarasota
$650,000
2 Beds ⋅ 2 Baths ⋅ Aloha Kai Apts SubDv. ⋅ 34242 Zip Code
Villa 61 at Aloha Kai | Upscale Coastal Living on Siesta Key Completely Remodeled | Quality Finishes | Fully Furnished | Turnkey Ready | Gated Community Discover your own slice of paradise at Villa 61 at Aloha Kai, a beautifully remodeled two-bedroom, two-bathroom with washer & dryer nestled within a desirable gated beachside community on Siesta Key, Florida. Showcasing quality finishes, inviting coastal décor, and a fresh, sophisticated style, this charming villa combines modern comfort with the relaxed elegance of island living. Whether you’re searching for a personal vacation retreat, a second home, or an investment property, Villa 61 offers an exceptional opportunity to enjoy the best of Florida’s Gulf Coast. Step inside this beautiful remodeled coastal retreat and experience a thoughtfully updated interior designed for comfort, style, and effortless living. The two-bedroom, two-bathroom open floor plan provides a welcoming space for owners and guests, while the screened-in porch offers the perfect spot to enjoy morning coffee, unwind after a day at the beach, or savor the warm Florida evenings. Sold fully furnished and turnkey ready, Villa 61 makes owning a beach getaway wonderfully easy. The furnishings are included, so you can settle in for your first owner stay or prepare to welcome your first vacation guests with ease. Gated Resort Living in a Premier Beach Location Located within Aloha Kai, a gated, family-friendly resort community in the heart of Crescent Beach, this villa offers a wonderful combination of privacy, convenience, and resort-style amenities with easy access to the spectacular white quartz sands of Crescent Beach, the emerald-green waters of the Gulf of Mexico, and Aloha Kai’s expansive heated swimming pool. Relax beneath shaded beach pavilions, take peaceful walks along the shoreline, and experience the unforgettable sunsets that make Siesta Key one of Florida’s most beloved coastal destinations. This Turnkey Vacation Home with Rental Potential offers the flexibility to enjoy your own highly sought-after Siesta Key,Florida retreat while the location make this an appealing opportunity for buyers looking for both lifestyle and investment potential exploring short-term rental opportunities. With a three-day minimum rental period, the property may accommodate vacation guests when you’re not enjoying it yourself, subject to applicable community rules and local regulations. Your Beachside Lifestyle Awaits, Imagine arriving at your own beautifully furnished turnkey costal villa located in a gated community setting , spending sun-filled days by the beach or pool, and ending each evening with a spectacular Gulf Coast sunset. Make Villa 61 your own and start living the Siesta Key lifestyle!

6020 Midnight Pass Road Unit 61, Sarasota
5300 Ocean Boulevard Unit 301, Sarasota
$1,195,000
2 Beds ⋅ 2 Baths ⋅ Terrace East SubDv. ⋅ 34242 Zip Code
RELISTED WITH AN ALMOST $200,000 PRICE ADJUSTMENT. This unique beach condo with sunrise, sunset and 270-degree views is an excellent opportunity. A beachy 1,446 square-foot, 2-bedroom 2-bath corner residence with extra space for a den boasts a special sunny, oversized corner, south-facing wraparound balcony with views of the beach, Gulf of Mexico, heated pool and Siesta Village. The unusual 1,130 square foot terrace adds extra space and is very useful for romantic alfresco dining, entertaining family and friends, special parties, kid's play space, put-put golf, shuffleboard, Florida sunning and more, which is not available in other condos. From this incredible Siesta Key location, you just walk out to the sugar-white sands of #1 Siesta Key beach for a relaxing swim in the azure-blue Gulf of Mexico or get some exercise walking the 3 miles of beachfront, snorkel, paddleboard, or take your beach bike for a spin on the beach. Enjoy your morning coffee or a cocktail from your extensive terrace balconies while watching the colorful hues of the Florida sunrise and sunset without having to leave your condo. For an entertaining experience, you are steps from quaint Siesta Village to indulge in fun shopping, dining and live music. The floor plan flows from the balcony on the beachside through to the back of the building with views looking east over Siesta Village and west over the Gulf of Mexico. This delightful light & bright larger corner residence features tile throughout perfect for beach living, a covered parking space and is just waiting for your personal touch. The elevator serves only two condos per floor with an updated private foyer and private laundry facilities shared by two condos. Private & exclusive Terrace East has a modern updated lobby and social room, newly refinished pool with new grills & refrigerator, new pool furniture, new roof in 2025, and equipped fitness center. All the fixed windows in all the condos will be replaced by the association by January 2028. This is a secure gated building with onsite full-time manager and maintenance man, very well-run association with active board and no current special assessments, and a secure surveillance system. Amenities include a heated pool for laps, a tennis court, pickleball, active fitness center, beautifully landscaped garden and grounds, and bicycle & paddleboard storage. Come make this your future Florida home!

5300 Ocean Boulevard Unit 301, Sarasota
5302 Las Rosas, Sarasota
$749,000
2 Beds ⋅ 2 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
Welcome to Palm Island, the Heart of Siesta Key!! Palm Island is an Island on an Island, located a short walk to World Famous Sugery Sands of Siesta Key Beach (Beach Access 10) and Siesta Village. With only one small humpback bridge on & off, this beachy neighborhood is a quiet oasis that is close the beach, restaurants and nightlife that makes this area so desirable. Great opportunity to build your dream home or use the current home as an investment or just enjoy the Island lifestyle. Current home has 2 bedrooms, 2 baths and a 2-car garage. Terrazzo floors throughout. The fenced back yard is a Tropical Paradise for taking in the soothing Gulf Breeze.

5302 Las Rosas, Sarasota
528 Ralph Street, Sarasota
$990,000
2 Beds ⋅ 2 Baths ⋅ Ocean Beach SubDv. ⋅ 34242 Zip Code
Virtually Staged. WATERFRONT OPPORTUNITY ON SIESTA KEY! ATTENTION BUILDERS, INVESTORS AND BUYERS: Turnkey waterfront property offering coastal living and excellent potential. This move-in-ready home comfortably accommodates up to eight guests and features durable terrazzo flooring throughout, recently completed exterior paint (2025), an updated kitchen with Corian countertops, extensive cabinetry and a new gas range, plus renovated bathrooms with clean, modern finishes and replacement windows. Enjoy a newer seawall and direct boat access to open water with just one bridge. The property also features a newly constructed front deck, parking for up to six vehicles and a converted garage/storage area ideal for beach equipment, bicycles and tools. A flexible bonus space could be used as a third bedroom, art studio, sunroom or home office. There is ample room to add an in-ground pool, subject to buyer verification and applicable approvals. Located on a street with surrounding homes reportedly valued up to $7 million, this property is well suited for investors, seasonal residents or anyone seeking a low-maintenance, lock-and-leave coastal home.

528 Ralph Street, Sarasota
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