Windward Passage Homes with Gulf/Ocean Frontage

Windward Passage Homes with Gulf/Ocean Frontage

Welcome to Windward Passage, a stunning subdivision nestled in the heart of Siesta Key, Florida, where the sun-kissed shores of the Gulf of Mexico meet luxurious coastal living. This exclusive community is a hidden gem in Sarasota County, offering residents an unparalleled lifestyle defined by breathtaking ocean views, pristine beaches, and a vibrant atmosphere.

Windward Passage is renowned for its exquisite homes that boast direct Gulf and ocean frontage, allowing you to wake up to the soothing sounds of waves and the gentle sea breeze every day. These meticulously designed residences feature spacious layouts, modern amenities, and expansive outdoor spaces perfect for entertaining or simply soaking in the sun. Imagine sipping your morning coffee on a private balcony while watching dolphins play in the surf or enjoying sunset dinners with panoramic views of the horizon.

Beyond the allure of the homes, Windward Passage offers a unique sense of community. Residents can enjoy leisurely strolls along the sandy beaches, partake in water sports, or explore the charming boutiques and gourmet restaurants that Siesta Key has to offer. With its close-knit atmosphere and friendly neighbors, you'll feel right at home from the moment you arrive.

Whether you’re looking for a permanent residence, a vacation getaway, or an investment opportunity, Windward Passage presents an idyllic setting that combines luxury, relaxation, and the beauty of Florida’s coastline. Discover your dream home in this enchanting subdivision and experience the best of coastal living in Siesta Key!

Newest Windward Passage Homes with Gulf/Ocean Frontage

4712 Ocean Boulevard Unit W5, Sarasota
$1,359,000
2 Beds ⋅ 2 Baths ⋅ Windward Passage SubDv. ⋅ 34242 Zip Code
Virtually Staged - Perfectly positioned to capture the ever-changing beauty of the Gulf, this northwest-facing residence offers a front-row seat to nature’s daily masterpiece. From the lush green lawn and swaying palm fronds to the Gulf’s ever-changing shades of turquoise, blue, and emerald, the views unfold in layers of coastal color. As the day draws to a close, the western sky ignites in brilliant sunset hues, transforming the landscape into a breathtaking panorama that never looks quite the same twice. Here, the view isn’t just something you see—it’s an experience to savor. Welcome to Windward Passage, where the beauty of Siesta Key meets the comfort of an exceptionally spacious coastal retreat. Offering 1,626 square feet of living space, this two-bedroom, two-bath residence blends timeless Gulf views with thoughtful modern updates. Renovated kitchen and bathrooms, luxury vinyl plank flooring throughout, impact-resistant windows on the waterfront facing side, and a newer air-conditioner provide the perfect balance of style, comfort, and peace of mind. Situated on the third floor, the home enjoys an ideal elevation—high enough to embrace sweeping coastal scenery while maintaining a wonderful connection to the tropical landscape below. An oversized private garage adds a level of convenience and storage rarely found in condominium living. Beyond the residence, the best of Siesta Key is practically at your doorstep. Just a leisurely 10-minute stroll brings you to the heart of Siesta Key Village, where lively tiki bars, exceptional dining, boutique shops, and live music create an atmosphere that’s distinctly island. And when the beach calls, the nearest public beach access lies just beyond "The Village" or an even easier 5-minute bike ride away. Whether you’re seeking a full-time residence or a cherished coastal getaway, this is a place to slow down, settle in, and appreciate the extraordinary beauty of everyday life on Siesta Key. Some properties are defined by their features. Others are remembered for how they make you feel. This one offers both.

4712 Ocean Boulevard Unit W5, Sarasota
4708 Ocean Boulevard Unit E4, Sarasota
$2,199,000
3 Beds ⋅ 3 Baths ⋅ Windward Passage SubDv. ⋅ 34242 Zip Code
Expansive floor-to-ceiling sliders open wide to welcome refreshing Gulf breezes and showcase unobstructed, panoramic water views, turning your open-floorplan living space into an indoor/outdoor oasis. With over 2,300 square feet, this light-filled condominium lives like a private home suspended above shimmering waters. The gourmet kitchen is both elegant and functional, featuring quartz countertops, custom wood cabinetry, and premium appliances, including a Thermador refrigerator and freezer, Wolf double ovens, Wolf microwave, and a Thermador induction cooktop. Panel-ready finishes, a built-in beverage cooler, and exceptional storage make this space ideal for both everyday living and entertaining. Rich acacia engineered wood flooring adds warmth and sophistication throughout the main living areas. The spacious primary suite captures sweeping Gulf views and offers a serene escape, complete with a beautifully renovated spa-inspired bath featuring split vanities and a large walk-in shower. Two additional bedrooms and stylishly updated baths are thoughtfully positioned on the opposite side of the residence for added privacy. Impact-rated windows and sliders provide peace of mind, eliminating the need for hurricane shutters. A private two-car garage with ample storage adds to the home’s convenience. Windward Passage features a Gulf-side pool, lushly landscaped grounds, and a pet-friendly setting. Perfectly positioned on the sought-after north end of the key, you’re just a short walk to the Village for charming boutiques, dining, and live entertainment.

4708 Ocean Boulevard Unit E4, Sarasota
4712 Ocean Boulevard Unit W10, Sarasota
$2,450,000
4 Beds ⋅ 4 Baths ⋅ Windward Passage SubDv. ⋅ 34242 Zip Code
Repriced $250,000! A rare opportunity to reimagine a Gulf-front penthouse on Siesta Key. Set in a boutique condominium community near Siesta Village, this expansive four-bedroom, four-bath residence offers over 3,900 air-conditioned square feet, full Gulf views and the kind of scale, frontage and location that are seldom available. With nearly 80 feet of linear Gulf frontage, the penthouse captures sweeping vistas of the azure Gulf waters, Big Pass, Lido Key and downtown Sarasota from nearly every room. The floor plan is exceptionally spacious, with grand living areas, high ceilings, a fireplace, two balconies, an attached two-car garage and the rare flexibility that comes with a residence of this size and presence. The two-building, 22-unit complex features a pool overlooking the Gulf, offering a relaxed setting to enjoy the waterfront lifestyle. This residence presents a unique canvas for a complete custom renovation. A new owner can transform this property into a spectacular coastal showplace, tailored to today’s luxury lifestyle. The existing floor plan includes generous entertaining spaces, a large kitchen footprint, two primary-suite areas, one with a private sauna, all ready to be reinterpreted with a fresh vision and design. Just moments from Siesta Village, with its restaurants, boutiques, boating and waterfront activities, this residence also enjoys proximity to Siesta Key’s world-famous white quartz sand beach. It is an extraordinary chance to create a one-of-a-kind Gulf-front penthouse in one of the island’s desirable locations. Beyond the island, vibrant downtown Sarasota’s cultural, shopping, dining and entertainment areas are just minutes away.

4712 Ocean Boulevard Unit W10, Sarasota
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