Windward Bay Condominiums, FL homes for sale & real estate

Windward Bay Condominiums, FL Homes for Sale

This spacious waterfront villa lives like a single family home but is MAINTENANCE FREE! It offers gorgeous Sarasota Bay and canal views with 1900 SF (the largest home in the community), 2 bedrooms plus a bonus room one that could be a 3rd bedroom, home office or nanny/in-law suite with its exterior entrance, 2 bathrooms, separate spacious laundry room with newer full sized machines (large enough to add a 3rd bathroom), plus Florida room with private patio, perfect for barbecuing the catch of the day, al fresco dining under the stars or watching manatees and dolphins. It's the best of all worlds. .. the size and convenience of a house yet the ease of condo living. As you enter this waterfron

Windward Bay Condominiums, FL Homes for Sale

Direct Gulf and Bay Views on Longboat Key. Enjoy stunning Gulf and Bay views from this 2-bedroom, 2-bath residence at The Castillian, a pet-friendly beachfront community on beautiful Longboat Key. The open, eat-in kitchen flows seamlessly into the living and dining areas— perfect for entertaining or relaxing by the sea. The living room, primary suite, and guest bedroom—all featuring rich wood flooring—open onto a spacious screened beachfront lanai, where you can take in spectacular sunsets and gentle Gulf breezes. The Castillian offers two well-maintained buildings, each with just 30 units and rare underground parking. Recent updates include new roofs on both buildings a

Windward Bay Condominiums, FL Homes for Sale

PENTHOUSE UNIT!! DEEDED BEACH ACCESS DIRECTLY ACROSS THE STREET!! New roof 2025! Top-floor, end-unit living with sparkling water views and everyday coastal ease. This light-filled 2-bed/2-bath residence opens with a reimagined, wall-removed kitchen that flows into the living area—finished with wood-look tile throughout and sleek quartz counters—so the view is the star from the moment you walk in. Step onto the balcony for morning coffee over the canal and watch boats drift by, then head out for a beach day via the community’s deeded Gulf access just across Gulf of Mexico Drive. Back at home, a brand-new roof adds peace of mind, while the gated Longboat Harbour lifestyle br

Windward Bay Condominiums, FL Homes for Sale

Experience the epitome of Island living in this meticulously kept and beautifully renovated retreat located in the beachfront community of The Westchester on Longboat Key. This ground floor walk-out, 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous kitchen opens to the large living/dining area and the spectacular views can be seen through impact resistant sliding doors that open wide for easy indoor/outdoor living. Step out to one of two private screened in lanais and you'll find the perfect spot to enjoy a morning coffee or an evening beverage while watching the sunset. This home is being offered with all the designer furnishings, so all you&rsq

Windward Bay Condominiums, FL Homes for Sale

The Quintessence of Coastal Living: A British West Indies Masterpiece on Longboat Key - Where Architecture Meets Paradise. Offered turn-key, this exquisite 4,000+ sq. ft. , 4-bedroom, 4.5-bath residence in Longboat Key’s prestigious Bonaire subdivision is a rare union of refined British West Indies architecture and the serene beauty of Florida’s Gulf Coast. Every inch of this home has been thoughtfully crafted to evoke a sense of effortless luxury—where sun-kissed days and gentle Gulf breezes blur the line between indoors and out. From the moment you step through the grand entrance, you’re embraced by light, texture, and tranquility. Creamy finishes, warm woods, and

Windward Bay Condominiums, FL Homes for Sale

GREAT NEW PRICE! An exceptional INVESTMENT and lifestyle opportunity awaits in this completely TURNKEY FURNISHED, 2 bedroom/2 bath coastal retreat in the GULF FRONT property of Sand Cay on the world famous barrier island of Longboat Key. Located in a prime Gulf front complex with resort style amenities and its own private beach, this condo offers the perfect blend of relaxation, recreation, and return on investment. Sand Cay’s attractive 3-night minimum rental policy and its efficient, friendly on-site rental office make it easy to maximize your income earning potential while enjoying a private island getaway. The JANUARY-APRIL 2026 HIGH SEASON IS FULLY BOOKED WITH RENTALS, so your 2