Siesta Key Real Estate

Luxury Homes for Sale in Siesta Key, FL

Welcome to your dedicated resource for luxury homes for sale in Siesta Key, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Siesta Key, FL agents, Dave Jones Realty specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the luxury properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Luxury Homes for Sale in Siesta Key, FL

$3,347,500
3 Beds 5 Baths A4676707 MLS
Freshly completed and built safely 10 feet above the island’s flood plain, 5103 Windward is a spectacular new waterfront residence where elevated design meets effortless island living. Set on nearly one-third of an acre along the Grand Canal, with 90 feet of new seawall and saltwater boating access to the Intracoastal Waterway and Gulf beyond, this is the kind of home that turns everyday life into a vacation. And the location? Hard to beat. From this central Siesta Key setting, the island’s legendary white-sand beaches and the laid-back charm of Siesta Village are just minutes away. Beach morning, boat afternoon, cocktails by the pool — it’s all within easy reach. Inside, 3,034 square feet of beautifully designed living space unfolds with an easy, open flow made for both relaxing and entertaining. The great room immediately draws you in with soaring double-height ceilings, rich architectural details, and a dramatic floor-to-ceiling fireplace wall. Walls of glass bring the outdoors in, framing expansive views of the pool, backyard, and sparkling canal beyond. Step outside and the fun really begins. A stylish outdoor lounge with wood ceiling accents, a professional grill station, and a heated pool and spa create the perfect backdrop for everything from lazy afternoons to unforgettable evenings with family and friends. As the sun goes down, thoughtfully designed landscape lighting takes over, casting the backyard in a warm, magical glow. The kitchen is every bit as impressive — and ready for everything from morning coffee to dinner parties. A premium Sub-Zero and Wolf appliance package, beautiful stone countertops, designer fixtures and finishes, a walk-in pantry, and adjoining laundry combine style with serious functionality. When it’s time to dine, the formal dining room delivers with a custom built-in buffet and French doors opening to a brick-paver patio. Picture dinner under the stars, a cool island breeze, and nowhere else you need to be. Need a little more room to play? The bonus room checks all the wit a pool bath, and two walls of glass sliders opening to the expansive outdoor living areas and picturesque water views. It’s the perfect spot for game day, movie night, guests, or simply kicking back after a day on the water. The primary suite is your private retreat. An adjoining office with custom built-ins, an oversized wardrobe designed for two, and a spa-inspired bath create a serene escape of your own. Soak in the freestanding tub, refresh in the frameless glass shower with rain head, or start the day at separate stone-topped vanities designed for effortless mornings. Two additional en-suite bedrooms give family and guests their own comfortable spaces to relax and recharge. Outside, the details continue with a brick-paver driveway, three-car garage, professional landscaping with timed irrigation, and exceptional curb appeal. Inside and out, thoughtful custom touches reflect the quality and craftsmanship you’d expect from Allegra Homes’ award-winning team. This is more than brand-new construction. It’s an invitation to embrace the Siesta Key way of life — mornings on the water, afternoons by the pool, evenings under the stars, and the beach always just a short drive away.Fresh. Waterfront. Effortlessly luxurious. Completely island. Your Siesta Key paradise is ready.

5103 Windward Avenue, Siesta Key

$3,295,000
4 Beds 4 Baths A4668457 MLS
One or more photo(s) has been virtually staged. This exquisitely reimagined waterfront estate embodies modern luxury and serene exclusivity, offering 174 feet of prime waterfrontage in the prestigious Sanderling Club on Siesta Key. On a lush, nearly half-acre parcel, the residence enjoys a southern orientation, where panoramic views of a bridgeless bay unfold through walls of glass. A backdrop of meticulously landscaped greenery ensures privacy, all just near the water’s edge. At the heart of the home lies a state-of-the-art culinary haven. The chef’s kitchen is equipped with premium Wolf and Sub-Zero appliances, including a gas range and integrated espresso system, set within rich Merillat solid-wood cabinetry and dual islands designed for function and entertaining. Flowing seamlessly into the sunlit living and dining areas, the open-plan design creates an effortless connection between indoors and out. The living space extends gracefully to a sophisticated entertainment patio, where a firelit lounge, sparkling pool and fully appointed outdoor kitchen echo the refinement found within. The primary suite offers a tranquil retreat, framed by a garden and oak vista, and complemented by a spa-inspired bath featuring a deep soaking tub, dual vanities, and indoor and outdoor showers. An adjoining office doubles as a guest suite, while additional en-suite accommodations ensure privacy and comfort for visitors. Modern conveniences and peace of mind abound such as remote-controlled wrought-iron gates, impact-resistant windows and doors, whole-house water treatment, advanced smart-home systems, new roof, backup generator and environmentally conscious amenities, including a 500-gallon propane supply and integrated mosquito-repellent system. As a resident of Sanderling Club, you’ll enjoy access to a private beach, boat slips, tennis courts, clubhouse and 24-hour security, an unrivaled blend of leisure, privacy and coastal sophistication. This residence has been meticulously curated for those who seek the ultimate fusion of luxury and tranquility, an invitation to a lifestyle defined by elegance, ease and timeless waterfront living.

1253 N Basin Lane, Siesta Key

$3,250,000
4 Beds 4 Baths A4643229 MLS
Under Construction. A rare opportunity to own a beautifully crafted custom home on Siesta Key by Nutter Custom Construction. This stunning custom residence is now nearing completion, with anticipated delivery in September 2026. Every detail has been thoughtfully curated to deliver an exceptional luxury living experience. This Coastal Contemporary residence offers 3,200 sq. ft. of interior living space and over 5,500 sq. ft. of total indoor/outdoor living, thoughtfully designed to maximize both luxury and comfort. Enjoy three spacious balconies, an outdoor kitchen, and a generous covered lanai that seamlessly blends indoor and outdoor living. Inside, the open floor plan is filled with natural light and features a stunning chef’s kitchen equipped with luxury appliances, custom cabinetry, and a walk-in pantry. The kitchen flows effortlessly into the dining area and great room, creating the perfect space for entertaining or relaxing with family. The home includes 4 bedrooms and 4 full bathrooms, providing ample space for family and guests. The expansive primary suite offers dual walk-in closets, a private balcony, and a serene retreat for homeowners. Upstairs, a versatile loft with access to a private balcony makes an ideal office or second living area. Additional highlights include an oversized 2.5-car garage, elevator access to all levels, and a full utility room for added convenience. The private backyard oasis features a beautiful pool and lush surroundings for year-round enjoyment. Located just minutes from Siesta Key’s world-famous beaches, as well as the vibrant shopping and dining options in The Village, this is a unique opportunity to personalize your dream home during this phase of construction. Don’t miss your chance to own a custom-built home in one of Sarasota’s most sought-after coastal communities. Please note: Some photos have been virtually staged for illustration purposes.

4903 Commonwealth Drive, Siesta Key

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