Windward Passage Homes with Beach Front Water Frontage

Welcome to Windward Passage, a picturesque subdivision nestled in the heart of Siesta Key, Florida, where sun-soaked beaches and serene waterfront living converge. Known for its stunning natural beauty and vibrant community, Windward Passage offers an idyllic retreat for those seeking a slice of paradise.

This charming enclave boasts exquisite homes with beach front waterfrontage, allowing residents to wake up to the soothing sounds of the ocean and breathtaking views of the Gulf of Mexico. With direct access to powdery white sands, homeowners can enjoy leisurely beach days, sunset strolls, and the invigorating sea breeze right at their doorstep.

Windward Passage is not just about stunning homes; it’s a lifestyle. The community is designed for those who appreciate the finer things in life, featuring beautifully landscaped grounds, spacious outdoor living areas, and private docks for boating enthusiasts. Whether you’re an avid sailor or simply love the tranquility of waterfront living, this subdivision caters to all your desires.

Located in the vibrant city of Siesta Key, residents have easy access to a plethora of local amenities, including boutique shops, gourmet dining, and lively entertainment options. The area is also renowned for its rich cultural scene and outdoor activities, making it a perfect destination for families, retirees, and anyone in between.

If you’re looking for a home that embodies the essence of coastal living, Windward Passage is your perfect match. Experience the ultimate in beachfront luxury and make this stunning subdivision your new home in paradise!

Newest Windward Passage Homes with Beach Front Water Frontage

$2,450,000

4 Beds ⋅ 4 Baths ⋅ Windward Passage SubDv. ⋅ 34242 Zip Code ⋅ A4688159 MLS ⋅ Active Status ⋅ Windward Passage BLDG.

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, Siesta Key

Start Your Search

This information is deemed reliable but not guaranteed. You should rely on this information only to decide whether or not to further investigate a particular property. BEFORE MAKING ANY OTHER DECISION, YOU SHOULD PERSONALLY INVESTIGATE THE FACTS (e.g. square footage and lot size) with the assistance of an appropriate professional. You may use this information only to identify properties you may be interested in investigating further. All uses except for personal, non-commercial use in accordance with the foregoing purpose are prohibited. Redistribution or copying of this information, any photographs or video tours is strictly prohibited. This information is derived from the Internet Data Exchange (IDX) service provided by San Diego MLS®. Displayed property listings may be held by a brokerage firm other than the broker and/or agent responsible for this display. The information and any photographs and video tours and the compilation from which they are derived is protected by copyright. Compilation © 2026 San Diego MLS®,