Siesta Key Homes with Key West Architectural style

Siesta Key Homes with Key West Architectural style

Welcome to Siesta Key, a charming barrier island located in Sarasota County, Florida. Known for its stunning white sandy beaches and crystal-clear waters, Siesta Key is a sought-after destination for those looking to experience the ultimate beach lifestyle.

One of the unique architectural styles you'll find in Siesta Key is the Key West style. Homes with Key West architecture typically feature bright and cheerful colors, metal roofs, large porches, and louvered shutters. This style is perfect for capturing the essence of island living and creating a laid-back and inviting atmosphere.

Imagine waking up to the sound of waves crashing and enjoying your morning coffee on a spacious porch overlooking lush tropical landscaping. With Key West-style homes in Siesta Key, you can turn this dream into a reality.

Whether you're looking for a vacation home, a retirement retreat, or a permanent residence, Siesta Key offers a wide range of real estate options to suit your needs. From cozy beach cottages to luxurious waterfront estates, there's something for everyone in this vibrant island community.

Come explore the beauty and charm of Siesta Key, where the Key West architectural style perfectly complements the island's relaxed and carefree vibe. Experience the magic of island living and find your slice of paradise in this tropical oasis.

Newest Siesta Key Homes with Key West Architectural style

$2,800,000
4 Beds 2.5 Baths Bay Island Park SubDv. 34242 Zip Code
Welcome to Bay Island, the Gateway to Siesta Key! This beautiful home is the beginning of enjoying the Siesta Key lifestyle. With 3500 sf under roof you can enjoy all the amenities Siesta has to offer. The tropical landscaping of the property alone will make you feel like you are on vacation. The home sits on 2 lots -located on both Anglin Drive and Flamingo Drive - offers you complete and total privacy. The open air pool is surrounded by beautiful travertine, a large area for entertaining, and covered decks on the front and back of the second level. The back deck is completely tiled and has ceiling fans as well as wired for outdoor speakers. It truly feels like you are at a fine resort! Everything from the inside out is just 4 years old. Arrive through a beautiful entryway with new staircase and new LVP flooring throughout. When you turn the corner you are welcomed into an open floor plan that is filled with lots of natural light. The living room has a new natural gas fireplace that adds a beautiful ambiance and a touch of elegance. The kitchen boasts an expansive quartzite island and features all Thermador appliances - including a gas stove, fridge and freezer columns and a dishwasher. The island is filled with storage drawers and undercounter pull out shelving. All cabinet drawers and doors are soft close. Walk out the new French doors onto an oversized, covered deck and take in the beautiful tropical landscaping. The owner's suite is located on the main living level and comes equipped with a spacious walk-in closet, a beautiful bath with a 10' double vanity and large walk-in shower. The main living area also features a nice cozy den that can easily be turned into a 4th bedroom. Located on the third level are two very large guest rooms as well as a fully remodeled bathroom. At the end of the day step out onto the third-floor deck and enjoy spectacular sunsets in your own home! The home as of late 2019 has all new siding, new roof, electrical and plumbing and irrigation. All the French doors and windows are hurricane rated. There are two new HVAC units as well. This home is perfect for weekly short term rentals within Sarasota City limits. Living on the North end of the island is perfect for a quick getaway to the beautiful chrystal sands of Siesta beach or a night in the village. Take a short trip over the bridge and enjoy all the amenities that Sarasota has to offer. You are close to downtown, Selby Gardens or shopping at the beautiful St. Armands.

3458 Anglin Drive, Sarasota

$2,300,000
4 Beds 3.5 Baths Sarasota Beach SubDv. 34242 Zip Code
Experience the ultimate island lifestyle on Siesta Key. This waterfront home offers the ideal blend of luxury, comfort and convenience, making it an ideal full-time residence or vacation retreat for those seeking the quintessential Siesta Key experience. Immerse yourself in the beauty of coastal living and indulge in the myriad of recreational opportunities just steps from your door in this sought-after location. Just two blocks from the pristine white quartz sands and azure water of Siesta Beach on the Gulf of Mexico and less than a mile from the vibrant Siesta Village, this Key West pool home epitomizes luxury coastal living. Boasting four bedrooms and 3.5 baths, this residence offers an open floor plan designed for relaxation and entertainment. The light-and-bright, open-concept floor plan features a spacious great room with high ceilings, all overlooking the pool and waterway. The large open kitchen boasts stainless steel appliances, while easy-care tile and engineered wood flooring flow throughout the home. Additional living spaces include a family room and dining area, ensuring ample room for relaxation and entertainment. A fabulous waterfront primary bedroom suite provides a serene escape with breathtaking views. Enjoy balmy breezes from the private balcony. Outdoor dining and lounge areas create the ideal ambiance for making memories with family and friends. The screened lanai and sparkling heated pool overlook a spacious yard shaded by a majestic oak tree, gently rolling to the waterfront dock on the Grand Canal. You'll delight in living on the water and marvel at the amazing marine life and waterfowl outside your door. Fish from your own backyard, launch your paddleboard or kayak from the dock, or just relax and enjoy living in paradise. For boaters, only one fixed bridge to the bay and Intracoastal Waterway with direct access to the Gulf of Mexico. Less than one mile from Siesta Village's unique boutiques and restaurants and only a 15-minute drive to downtown Sarasota's urban and cultural amenities, shopping, schools and hospital.

5322 Avenida Del Mare, Sarasota

$1,499,000
3 Beds 3 Baths Siesta Beach SubDv. 34242 Zip Code
Just reduced 100K ! This Unique Coastal Contemporary is completely updated in a highly desirable community on Siesta Key just minutes to the famous Siesta Key Beach! If you are seeking the perfect investment opportunity as a rental or multigenerational living with an in-law suite this is it! The upstairs includes 2bd/2 baths with incredibly spacious living and the first floor features a 1bd/1 bath with living area/studio. Soaring ceilings and natural light make this coastal home so inviting. The exterior travertine marble staircase with sidelights leading to the front door is the first indication of how perfectly planned this renovation was. There was no expense spared with the designer interior finishes as you enter this expansive open floor plan with LVT floors throughout. The kitchen was so well tailored for entertaining with a 10' natural quartzite island with waterfalls and composite sink. The high end Schuster Modico cabinetry is complimented by the Stainless appliances including a Fisher Paykel refrigerator and a GE Profile induction range with convection oven and microwave drawer. Retire to the master suite that will wow you with its size and walk in closet with built-ins. The master bath features gorgeous tile and quartz finishes, dual vanities and a free standing tub and separate shower. The secondary bedroom is spacious as well with plentiful closet space and a fully remodeled bath with quartz finishes. The laundry facility includes brand new stacked washer/dryer and cleverly created storage space. As you venture to the outdoors you can enjoy the cool ocean breezes from the upstairs patio off the living room and master bedroom made of trek decking. You will love the oversized pool cage and as you meander down to the pool / lanai you will be captivated by the beautiful natural travertine marble pavers and plentiful covered area to relax or entertain. The resort style pool with coastal tiles will lure you in to cool off on those hot summer days but enjoy the heated pool on those cool winter nights! You will love the privacy as you are surrounded by tropical landscaping with a fully fenced backyard and maintenance free living at its best ! This is practically a new home with all the numerous updates including, new roof, new electrical and plumbing, new AC, new pool heater, all new appliances, interior and exterior painting with new hardiboard siding, all new LED lighting throughout with windows shades to filter the sunlight. Even the garage is impressive with an epoxy floor and slat board walls. Come enjoy the Florida lifestyle and everything Siesta Key has to offer. Minutes to the Village with restaurants, shopping and the World renowned Siesta Key Beach!

4939 Commonwealth Drive, Sarasota

$4,950,000
4 Beds 4.5 Baths Midnight Harbor Sub SubDv. 34242 Zip Code
Welcome to 1243 Starboard, a residence where luxury and design unite in a harmonious blend of grandeur. This 4-bedroom+Office/4.5-bathroom/3+ car garage home, built by one of the finest local builders, Voigt Construction, sits on nearly a half acre of deep sailboat Siesta Key waterfront and offers unrivaled island life. Spanning 5142 sqft of air-conditioned space, this home offers a lifestyle of unparalleled sophistication. The spectacular Great Room is a masterpiece, adorned with soaring pecky cypress ceilings that draw the eye upward, complemented by the warmth of mahogany wood floors that flow seamlessly throughout. The heart of this home is its chef's dream kitchen, boasting white hardwood cabinetry, pristine countertops, and an extra-large island for both culinary artistry and casual gatherings. The ocean-inspired blue backsplash adds a touch of coastal charm, creating a culinary space that is as visually stunning as it is functionally exquisite. The open-concept kitchen and living room combination make this floor plan versatile — functional for everyday activities and entertaining. Go to your 220+ bottle wine refrigerator and take a glass to open living concept, where you'll find the perfect spot to enjoy winter evenings. Light up your gas fireplace, and open your impact glass sliders effortlessly to connect you to the outdoors to feel the cool Florida seaside breeze. The standard of living here is high as you indulge in opulence within the expansive master suite of this remarkable residence. The generously sized owner's retreat is a haven of serenity, offering a luxurious escape within the confines of your own home. A sprawling walk-in closet provides ample room for your wardrobe, ensuring a clutter-free sanctuary. The master bathroom is a spa-like oasis, featuring high-end finishes, dual vanities, a soaking tub, and a separate, oversized shower. Every detail has been meticulously crafted to create a private haven where relaxation and rejuvenation seamlessly coexist. Whether winding down after a long day or waking up to the promise of a new one, the master suite is a testament to refined living. Each of the other three bedrooms in this residence is a retreat in its own right, featuring spacious walk-in closets and en-suite bathrooms. These thoughtfully crafted private sanctuaries offer the perfect amount of comfort, ensuring that every resident enjoys a restful escape within the confines of their personal haven. The best is yet to come as the outdoor space embraces the epitome of Siesta Key living. A captivating pool beckons for refreshing dips, an expansive outdoor balcony offers water views, and a cozy fire pit sets the scene for unforgettable evenings, creating an idyllic haven for relaxation under the starlit skies. Boasting deep sailboat water access & a 30,000 lb boat lift, the property invites maritime enthusiasts to embark on aquatic adventures from their own backyard. Plus, with the addition of a new automatic generator, you can rest assured knowing that your home is equipped for any unforeseen power outages, providing peace of mind for you and your loved ones. This meticulously designed residence offers a sanctuary for those who appreciate the finer things in life. This Siesta Key gem is not just a home; it's a testament to the allure of coastal living. Come discover your blend of elegance and waterfront bliss in this extraordinary residence.

1243 Starboard Lane, Sarasota

$2,999,000
3 Beds 3.5 Baths Bay Island SubDv. 34242 Zip Code
New price! Experience the pinnacle of island living on coveted Bay Island on north Siesta Key with this exceptional waterfront residence on deep sailboat water. Enjoy direct access to Sarasota Bay, Big Pass, and the Gulf of Mexico, and quick connections to the Sarasota mainland, making it a boater's paradise. This impressive home boasts an open floor plan, high ceilings, and natural light and offers spectacular views. Step into the soaring two-story foyer, illuminated by a grand atrium window and a stunning chandelier, guiding you into the open-concept layout. The kitchen, a haven for culinary enthusiasts, showcases Cucine Lube cabinetry, granite countertops, a Sub-Zero refrigerator, a Wolf oven, and a Wolf 5-burner natural gas-cook top centered around an elegantly curved oversized island. Adjoining the kitchen, a planning desk overlooks the serene waterway, seamlessly connecting to the open dining area, family room, and living room, featuring a natural gas fireplace with a mother-of-pearl fascia with panoramic views of the pool and waterway through French doors. Completing the main level is a spacious first-floor guest suite, a full and half bath, and a laundry room. Recent enhancements include new LVP flooring, motorized blinds on French doors, and plantation shutters. Ascend the new staircase to the second level, housing two private suites and an expansive IPE wood balcony with access from each suite overlooking the pool, spa, and waterfront. The luxurious owner’s suite invites relaxation with a window seat and a large walk-in closet. Double doors open to a lavish bathroom with separate vanities, a soaking tub, and an oversized two-person glass-enclosed shower. The second suite features a generous bedroom and ensuite bathroom with dual vanities and a shower. The outdoor oasis boasts a fabulous pool and spa, perfect for unwinding or entertaining guests while reveling in mesmerizing sunsets. A sprawling composite dock on Hanson Bayou includes a 16,000-lb. boat lift, dual jet ski dock, and fishing station. Indulge in paddleboarding, fishing, or kayaking from your backyard and frequent visits from playful dolphins. Also, discover an expansive paver pool deck, tropical landscaping, a circular driveway, an irrigation system, a fenced yard, and an insulated, air-conditioned two-car garage. This waterfront gem, featuring recent upgrades including new interior paint, baseboards & trim, LVP flooring, staircase, fireplace surround, carpets, lighting, hardware, water heater, and more, offers excellent weekly rental potential within Sarasota City limits. Close to Siesta Beach, Siesta Village, downtown Sarasota, St. Armands Circle, Sarasota Memorial Hospital, and top-notch schools, this residence epitomizes the ideal island lifestyle in a prime Sarasota location.

3532 Flamingo Avenue, Sarasota

$1,800,000
4 Beds 2.5 Baths Siesta Woods SubDv. 34242 Zip Code
Experience the essence of Siesta Key living in this meticulously renovated four-bedroom haven on Siesta Key. In a small enclave minutes from the world-famous powdery white sands of Siesta Beach and the azure waters of the Gulf of Mexico. Boasting two stories of refined living space, this home is designed for hosting large families or accommodating guests effortlessly. Step into an inviting ambiance highlighted by a glass French door entry, tile and hardwood floors and an expansive open concept living area featuring vaulted ceilings. The central kitchen seamlessly connects to the living and dining spaces, offering a breakfast countertop, stainless steel appliances, granite countertops and bespoke wood cabinetry. French doors lead to an expansive covered balcony, ideal for entertaining or unwinding, with easy access to your private saltwater pool via a staircase. The upper level features a split floor plan housing a spacious primary bedroom and bath suite, two additional bedrooms, a full bath and a convenient laundry room. Downstairs, discover a spacious family room, an office, an oversized fourth bedroom, a bonus area and a half-bath, all tiled throughout. French doors open to an oversized screened-in lanai and a large free-form saltwater pool, ideal for relaxation and play. A tropical paradise, the lushly landscaped, walled and gated property offers unparalleled privacy, complemented by a circular paver driveway and picturesque walkways. Enjoy easy-care composite decks and stairs with aluminum railings, PGT impact glass windows and doors, and an oversized two-car garage with additional storage space for bikes and beach essentials. Just a mile from the renowned Siesta Key Beach, indulge in sun-soaked days and captivating sunsets. Close to the charming eateries and boutiques of Siesta Village, offering a quaint and vibrant local scene. Only 15 minutes by car across the North Bridge to downtown Sarasota, where a world of restaurants, shopping and cultural amenities awaits. This property encapsulates the essence of Siesta Key's allure, offering an unparalleled blend of elegance, comfort and coastal bliss. Whether it's relaxation by the pool or venturing into the island's vibrant offerings, this sanctuary promises the island lifestyle.

5188 Siesta Woods Drive, Sarasota

$7,995,000
5 Beds 5.5 Baths Hidden Harbor SubDv. 34242 Zip Code
Experience the epitome of waterfront living at 1250 Hidden Harbor Way, Siesta Key, FL, a custom-built sanctuary where coast elegance meets timeless serenity. Nestled on a private, peninsula lot, the home has sweeping bay views all the way to the Sarasota skyline, with 409 ft. of water frontage, offering 280-degree unobstructed water views. This lavish 5 bed, 5 1/2 bath residence boasts 7,506 sq ft under air, a 5-car garage that includes an additional several thousand sq ft of finished space and sits on over half an acre of lush grounds. Embrace the boating lifestyle with direct access to the sparkling waters of Sarasota Bay from your secluded deepwater dock, discreetly tucked away and equipped with two boat lifts. The outdoor haven features a gated entrance, newly painted exterior (2023), natural seawall, terraced yard, infinity pool with spa, waterfall, and slide, several large outdoor terraces with a summer kitchen sporting a brand new grill. Inside, some of the amenities you'll find are cathedral ceilings, Lutron lighting system, speaker system, built-in cabinetry features, crown molding, solid core doors, an electric/hydraulic 3-stop elevator, and a security system. The newly painted main living space is completed surrounded with bay views and is comprised of a living room with cathedral ceilings, dining room, a two-story office with loft, art niches, a gourmet kitchen with butcher block island, custom cabinetry and top-of-the-line appliances, a family room, theater room, and large laundry room with loads of storage. The primary suite features a private terrace, with dual walk-in closets and a spa-like bath with marble floors and countertops, a free-standing soaking tub, dual vanities, glass walled double shower and two water closets. On the upper level, you’ll find 4 generous bedrooms. Each has ensuite custom tiled baths and spacious walk-in closets. Three of the bedrooms have views of the bay, and the other has its view overlooking the front yard from a private alcove. Additional highlights include a crow’s nest reading/yoga room with 280-degree bay views, enormous non-conforming space, 5-car split garage with ample storage, 600 sq ft exercise center, and hobby craft room. The bayfront infinity pool with fiber optic lighting, an outdoor 'cave' shower, rock water slide, and heated spa. Just two miles from the world-renowned Siesta Key Beach, you'll find yourself drawn to the powdery white sands and azure waters that have made this locale one of the most sought-after destinations in the world. The exclusive location of this magnificent property allows for easy access to the vibrant dining, shopping, and cultural experiences that Sarasota has to offer. Yet, it retains the tranquility and privacy that one would expect from a sophisticated coastal retreat, providing the perfect balance of luxury and leisure. SELLER FINANCING AVAILABLE. **Subject to credit qualification and lender approval.

1250 Hidden Harbor Way, Sarasota

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