Siesta Woods Real Estate

Siesta Woods Real Estate

Welcome to Siesta Woods, a hidden gem nestled in the heart of Siesta Key, Florida. This charming subdivision offers a unique blend of tranquility and vibrant coastal living, making it a sought-after destination for those seeking a slice of paradise. With its lush landscapes and serene surroundings, Siesta Woods is perfect for families, retirees, and anyone in between who desires a peaceful yet engaging lifestyle.

Siesta Woods is conveniently located just minutes away from the world-renowned Siesta Key Beach, famous for its powdery white sands and stunning sunsets. Residents can enjoy easy access to a variety of outdoor activities, including kayaking, paddleboarding, and biking along scenic trails. The nearby Siesta Key Village is brimming with delightful shops, restaurants, and entertainment options, ensuring that there’s always something to explore.

The subdivision itself features beautifully designed homes that reflect the laid-back charm of coastal living. With a range of architectural styles and sizes, Siesta Woods caters to diverse preferences, making it easy for prospective homeowners to find their dream abode. The community is known for its friendly atmosphere, where neighbors become friends, and gatherings are a regular occurrence.

Siesta Woods is not just a place to live; it’s a lifestyle. Embrace the Florida sunshine and the vibrant culture of Siesta Key while enjoying the peace and privacy that this enchanting subdivision provides. Whether you’re looking to invest in a vacation home or a permanent residence, Siesta Woods is the perfect choice for those who appreciate the best of both worlds. Come discover your new home in this idyllic community today!

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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