Siesta Woods Real Estate

Siesta Woods Real Estate

Welcome to Siesta Woods, an enchanting subdivision nestled in the heart of Siesta Key, Florida. This charming community is perfectly situated in Sarasota County, known for its stunning beaches and vibrant culture. Siesta Woods offers a delightful blend of tranquility and convenience, making it the ideal location for families, retirees, and anyone seeking a serene lifestyle by the sea.

The homes in Siesta Woods are characterized by their unique architectural styles, beautifully landscaped yards, and a welcoming atmosphere that fosters a strong sense of community. Residents enjoy spacious living areas, modern amenities, and the opportunity to personalize their homes to reflect their individual tastes. The subdivision’s layout encourages friendly interactions among neighbors, making it a great place to build lasting friendships.

One of the standout features of Siesta Woods is its proximity to the world-renowned Siesta Beach, frequently ranked among the best beaches in the United States. Here, residents can bask in the sun, stroll along the powdery white sands, or indulge in water sports like kayaking and paddleboarding. Additionally, the nearby Siesta Village offers an array of boutique shops, delicious dining options, and lively entertainment, ensuring that there’s always something to do.

Nature enthusiasts will appreciate the nearby parks and nature trails, perfect for hiking, biking, or simply enjoying the beautiful Florida weather. With its prime location, friendly community, and access to stunning natural beauty, Siesta Woods is not just a place to live; it’s a lifestyle waiting to be embraced. Come discover the charm of Siesta Woods, where your dream home awaits!

Newest Listings in Siesta Woods

14195 Siesta Road, Largo
$1,825,000
6 Beds ⋅ 5 Baths ⋅ Siesta Woods SubDv. ⋅ 33774 Zip Code
Welcome to your ultimate private estate! This masterfully designed luxury executive home offers the pinnacle of grand-scale entertaining and seamless multigenerational living with TWO OWNERS SUITES all completely and beautifully remodeled in 2026. Sitting on an expansive 0.65-acre lot, this spectacular 6-bedroom, 4.5-bathroom sanctuary pairs turnkey elegance with a resort-style backyard, flawlessly designed for high-end comfort, modern luxury, and exceptional functionality with abundant storage spaces thoughtfully integrated throughout the entire home. The sprawling main level is anchored by a gourmet chef's kitchen, newly reimagined for the ultimate culinary experience with a massive central island featuring comfortable seating for 8, sleek quartz countertops, dual sinks, and a sophisticated dry bar perfect for staging refreshments. The kitchen opens seamlessly to a sunlit breakfast area, a welcoming family room with a cozy fireplace, and elegant formal living and dining spaces. Designed for effortless hosting, a game room/flex space flows directly out to the pool area. Step into this amazing FIRST LEVEL PRIMARY SUITE featuring dual walk-in closets and a spa-like bath. Rounding out the lower level is a spacious second bedroom with direct access to a beautiful full bath with modern finishes. Upstairs acts as its own private retreat, headlined by the second luxurious owner's suite complete with a cedar-lined walk-in closet, a stunning bathroom, and direct access to a generously sized upstairs deck—a sprawling, fantastic vantage point to host intimate gatherings or watch breathtaking nightly sunsets over the pool below. Three additional oversized bedrooms and another beautifully appointed bathroom complete the top floor. For ultimate convenience, full laundry rooms are located on both levels. The backyard is an absolute entertainer's paradise engineered for fun across all generations. Dive into the oversized pool, enjoy the convenience of a dedicated pool bath, practice your golf swing on your own PUTT PUTT COURSE or host tournaments on your private VOLLEYBALL COURT . The grounds feature premium artificial turf for effortless, low-maintenance beauty year-round, alongside massive patio spaces perfect for hosting unforgettable gatherings. For the hobbyist, car enthusiast, or anyone dreaming of the ultimate man cave, the property features a massive, DETACHED THREE CAR GARAGE perfect for a custom workshop, vehicle collection, or private home gym. This space offers a spacious loft with endless opportunities! Perfectly situated for peace of mind and convenience, the property is located in a highly coveted NON FLOOD ZONE just a 5-minute drive from the beautiful sands of Indian Rocks Beach, with premier shopping , golf courses, and many excellent restaurants located just minutes away.

14195 Siesta Road, Largo
5188 Siesta Woods Drive, Sarasota
$1,650,000
4 Beds ⋅ 3 Baths ⋅ Siesta Woods SubDv. ⋅ 34242 Zip Code
Experience the best of Siesta Key living at 5188 Siesta Woods Drive, a spacious four-bedroom home offering exceptional privacy, expansive indoor and outdoor living and a resort-style pool setting just one mile from Siesta Key Beach. Surrounded by extensive tropical landscaping and enclosed by a privacy wall and gated entrance, the property feels wonderfully secluded while remaining close to everything that makes island living so desirable. Additional pool privacy screens and thoughtfully designed landscaping further enhance the sense of seclusion. The elevated main living level is bright and open, with vaulted ceilings, tile and hardwood floors and an easy flow between the living, dining and kitchen areas. The remodeled kitchen features granite countertops, custom wood cabinetry, stainless steel appliances, abundant workspace, breakfast bar seating and a Culligan reverse osmosis water system. Three new refrigerators, located in the kitchen, garage and bar area, provide added convenience. French doors with impact glass open to a spacious covered balcony overlooking the pool and tropical surroundings, with plenty of room for dining, entertaining or relaxing. A split bedroom plan provides privacy, with a spacious primary suite featuring two thoughtfully redesigned walk-in closets. Two additional bedrooms, a full bath and laundry room complete the main level. The lower level adds tremendous flexibility with a large family room, office, oversized fourth bedroom, bonus area and half bath, creating wonderful options for guests, recreation or working from home. French doors lead directly to the expansive screened lanai and heated, free-form saltwater pool, one of the home’s standout features. A generous paver deck offers both sunny and shaded areas for lounging, dining and entertaining, complemented by multiple covered areas, privacy screens, lush landscaping and an outdoor shower. A new pool pump and chlorinator were added in 2024. Impact windows and doors provide additional peace of mind, complemented by a metal roof, three-zone air conditioning, composite decking and stairs and an oversized two-car garage with additional storage. Recent 2025 improvements include a new washer and dryer, a resurfaced and sealed garage floor and newly resurfaced pavers surrounding the pool and along the driveway. Meticulously maintained and in excellent condition, with a pre-listing inspection completed, this home offers an uncommon combination of privacy, space and exceptional outdoor living. An extensive collection of furnishings is also available for purchase separately, offering buyers the opportunity for a turnkey, move-in-ready island home. Ideally situated approximately one mile from Siesta Key Beach and convenient to Siesta Key Village, with downtown Sarasota’s dining, shopping, arts and cultural attractions just a short drive away. (Garage refrigerator, TVs and Sono system are not included)

5188 Siesta Woods Drive, Sarasota
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