Windward Bay Villas For Sale in Longboat Key - 5 villas

Remarks: Welcome to coastal luxury living in Windward Bay, one of Longboat Key's most sought-after waterfront communities. Perfectly positioned between the sparkling waters of Sarasota Bay and the pristine Gulf beaches, this completely renovated 2-bedroom, 2-bath villa offers an exceptional blend of modern elegance, resort-style amenities, and the coveted island lifestyle buyers dream about. Fully reimagined and rebuilt from the studs, this stunning residence showcases high-end craftsmanship and designer finishes throughout. Every detail has been thoughtfully upgraded, including brand-new electrical systems, plumbing, drywall, insulation, kitchen, bathrooms, fixtures, and finishes—providing the peace of mind and comfort of essentially new construction within an established waterfront community. The bright, open-concept floor plan is flooded with natural light and designed for effortless indoor-outdoor living. The beautifully appointed chef's kitchen flows seamlessly into the living and dining areas, creating an inviting space ideal for entertaining, seasonal gatherings, or everyday enjoyment. A dedicated 220-volt outlet offers convenient electric vehicle charging, adding modern functionality and future-ready convenience. One of the villa's most desirable features is its easy ground-level access with no stairs, making everyday living simple and accessible. Pet lovers will appreciate Windward Bay's generous pet-friendly policy allowing up to two pets, a rare and highly desirable amenity on Longboat Key. Step outside to your private patio retreat surrounded by lush tropical landscaping and mature greenery. Enjoy peaceful mornings with coffee, spectacular sunset skies, and relaxing evenings gathered around the fire pit just moments from beach access. The Gulf of Mexico is only steps away, offering endless opportunities for shelling, beach walks, swimming, paddleboarding, and breathtaking sunsets. Residents of Windward Bay enjoy an unmatched collection of resort-style amenities set across nearly 27 acres of beautifully maintained waterfront property, including: Three beach access points to the powdery sand beaches of Longboat Key. Nearly one-half mile of scenic waterfront walking paths and nature trails. Two heated swimming pools. Six tennis and pickleball courts. Fitness center, sauna, clubhouse, library, and social gathering spaces. Two private marinas with boat slips and jet ski slips (for rent and subject to availability). Private fishing pier with panoramic bay views. Kayak storage and launch areas. Outdoor grilling stations, fire pits, and waterfront gathering areas. Lush park-like grounds with mature tropical landscaping. Whether you're searching for a primary residence, seasonal retreat, second home, snowbird escape, waterfront villa, beach getaway, or investment opportunity, this move-in-ready residence offers an unparalleled combination of location, lifestyle, and value. Ideally located minutes to St. Armands Circle, Sarasota's vibrant arts and dining scene, championship golf courses, boating destinations, waterfront restaurants, and world-renowned Gulf Coast beaches, this exceptional property delivers the very best of Longboat Key living. Experience the ultimate in island living where luxury, comfort, boating, beach access, and resort-style amenities come together in one extraordinary coastal retreat.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)

Listing Agent: Sharon Austin (678-756-4020)

Remarks: AMAZING $51,000 PRICE IMPROVEMENT! YOUR SUNRISE SANCTUARY! YOUR SUNSET ESCAPE! An End Unit Villa—Steps From Both Shores! There’s a moment just before sunrise—when soft light touches the bay and the world feels brand new. From this beautifully updated 1504 sq foot, 3-bedroom, 2-bath end-unit villa, you wake to that glow each morning. And while the bay lies just a short stroll from your door—where dolphins and manatees grace the shoreline—the sense of tranquility begins the moment you step inside your villa. Welcome to your story at Windward Bay, Loved for 33 Years, Transformed for the Next Chapter! Brand-new luxury vinyl plank flooring stretches throughout the living spaces. Custom White wooden plantation shutters open like pages of a book, revealing light-filled rooms, a bright inviting great room and a refreshed kitchen where new soft-closing cabinetry meets the timeless richness of granite countertops. Being a corner end unit means privacy, extra windows, and the kind of natural light you feel more than you see. The great room spills out to your private outdoor patio—perfect for morning coffee, late lunches, or evening breezes. And as evening arrives, simply walk across the street. The Gulf paints the sky in gold and coral, offering unforgettable sunsets that become a treasured part of your daily rhythm. This home offers peace of mind along with beauty. It’s a place where you can truly exhale. This is effortless, maintenance-free living, where parking sits mere steps from your door and bringing in groceries is a breeze. No elevators. No stairs. No inconvenience. Just the freedom of ground-level coastal life. Here, maintenance-free living means all the big things are already done: the entire exterior was upgraded in 2020 with hurricane-impact windows, hurricane-impact sliding doors, and a new roof. "Pet Friendly" Windward Bay is one of Longboat Key's most beloved waterfront communities—known for its mature landscaping, resort-style amenities, and genuine sense of warmth. People don't just move here; they stay here. In fact, the current owner of this villa has lived here for 33 years, a testament to the comfort, community, and connection the neighborhood provides. Windward Bay isn't just a place to live. It's a place to belong. Spanning 26 lush acres, the community offers three beach access points, a 1/2-mile nature trail, two heated pools, fitness center, sauna, clubhouse, tennis and pickleball courts, kayak launches, boat docks (waitlist), covered parking, and storage. Wildlife is abundant throughout the property, adding magic to everyday life. Financially strong, Windward Bay has completed its Milestone Inspection and Capital Reserve Study. Monthly fees were reduced in 2025 and increased only $13 for 2026. With Downtown Sarasota, St. Armands Circle, Bridge Street, renowned restaurants, championship golf, boutique shopping, and cultural attractions just minutes away, you're perfectly positioned between quiet island tranquility and vibrant coastal life. A Home That Feels Like a Vacation—Every Single Day! A place ready for its next chapter—your chapter. Your Windward Bay story starts here—reserve your private viewing today.

Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)

Listing Agent: Debby Mccaig (941-544-1713)

Remarks: UNBEATABLE VALUE! AMAZING PRICE FOR A BRAND NEW BEACH & BAY VILLA! Renovated with precision, the final finishing touches were completed in 2025 (12 weeks in living time since renovation) for this quality engineered, down to the studs, two-bedroom and two-bath beach getaway villa. From the moment you step inside, you'll be greeted by a thoughtfully designed sunny open floor plan boasting recessed lighting and an array of sleek finishes throughout the home. Distinguishing features include the true craftmanship of custom solid core doors, chic beach themed door and cabinet knobs, custom designed laundry closet housing a Full-sized front load Samsung washer & dryer, self-close solid kitchen cabinets with a bonus spice rack cabinet, pull out shelves in the pantry and below the sink, ceramic floor tiling through-out including a curb less shower entry located in the primary suite’s “ensuite bathroom. The pièce de résistance is the Cambria Quartz (lifetime warranty) kitchen countertop chosen for the beach inspired aqua accents that showcase both a breakfast bar and a dual temperature wine/beer refrigerator for added pleasure. The second bedroom is cleverly designed to serve as both an office and a guest space, complete with a comfortable “guest chest” Murphy bed cabinet. For peace of mind while away, the villa is equipped with the latest Wi-Fi enabled keyless smart lock entry system, as well as a smart remote thermostat to monitor and manage remotely. Worry free living with a New A/C (2022), Water Heater (2024) and recent Hurricane Impact Windows/Sliding Doors, Roof, & Carport (2020). Located directly across the street, with 3 beach access points (one private deeded access) is the tranquil Gulf with its crystal-clear turquoise blue waters and uncrowded sandy beaches that attract visitors from all over the world. A low-density residence and a nature lover’s delight: from captivating bird watching to the frolicking dolphins and manatees of Longboat Key. Windward Bay's unparalleled amenities include 2 tennis/pickleball courts, 2 marinas with 28 boat & jet ski slips for a low monthly fee (first come first served), barbecue grills throughout, fishing piers, 2 fish cleaning stations, kayak racks, 2 heated pools, shuffleboard, bike racks, a clubhouse with kitchen, library, fitness room, meeting room, 2 saunas, and community fire pits throughout the property. Conveniently accessible to Downtown Sarasota, St. Armands Circle, Anna Maria Island, Historic Cortez Fishing Village, Championship Golf Courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Welcome home to “Pet Friendly” Windward Bay, where TWO pets are allowed. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete and Monthly Condo Fees for 2025 were actually reduced. This wonderful condominium exemplifies “Florida Gulf to Bay Living” at its finest. Windward Bay: "A Special Place and A Gem of a Community." Whether you're looking for a vacation home or a permanent residence, book your private showing today. Longboat Key and Villa 7 in Windward Bay offer everything you could desire to live the life you have always dreamed of!

Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)

Listing Agent: Debby Mccaig (941-544-1713)

Remarks: Virtually Staged. PRICE REDUCED! Experience the ultimate Longboat Key lifestyle in this waterfront gem featuring stunning Sarasota Bay and canal views. This spacious residence offers two Bedrooms, two Bathrooms, a versatile Bonus Room (ideal as a 3rd Bedroom, Home Office or private In-Law/Nanny Suite), plus a generous laundry room with newer full-size machines. This villa has been completely and meticulously renovated, with no detail overlooked and no expense spared. Beyond its stunning finishes, this home offers something incredibly valuable: Exceptional Peace of Mind! Major infrastructure updates include new electrical and plumbing systems, new Luxury Vinyl Plank flooring, fresh interior paint, and Hurricane-Impact Windows and Doors throughout. EVEN BETTER...exterior Building Maintenance Repairs and Insurance (including Flood, Hurricane, and Hazard coverage) are all included in the monthly HOA fee, creating a truly low-stress ownership experience. Recent updates include stylishly renovated bathrooms with stone countertops and new vanities, while the spacious new kitchen offers stainless appliances, quartz counters, plus abundant storage and counter space. This home also features a light-filled Florida room opening to a private patio, perfect for outdoor grilling, dining under the stars or watching playful manatees and dolphins in the canal. And for ultimate convenience, everyday living is effortless with the attached covered carport. Beyond your private retreat, Windward Bay offers resort-style amenities across 26 pristine, landscaped bay front acres. Enjoy two heated pools with complimentary lounge seating, saunas, tennis and pickleball courts, a fitness center, shuffleboard, boat slips ($50/month or $55/month with owner-provided lift), kayak/paddle board storage and launch ($45/year), fishing, and three private beach access points. Plus, Zota Beach Resort is just across the street for elegant dining and nightly sunsets. Windward Bay is a proactive, well-managed community that has passed its structural integrity inspection and is certified for another 10 years. Owners may rent up to twice per year with a one-month minimum, offering excellent income potential. Best of all—this rare Longboat Key community is pet-friendly for Owners and Renters! Don’t miss your chance to own a slice of island paradise and enjoy a relaxed, coastal lifestyle surrounded by natural beauty and first-class amenities. Your dream retreat awaits!

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Christina Weger (941-773-4154)

Remarks: Virtually Staged. This exquisite turnkey-furnished 2-bedroom, 2-bathroom villa has been completely and meticulously renovated, with no expense spared. Beyond its stunning finishes, this home offers something even more valuable: Exceptional Peace of Mind! Major infrastructure updates include Hurricane-Impact Windows and Sliders throughout, new electrical and plumbing, a 2023 HVAC system, 2026 water heater, 2021 roof, and fresh interior and exterior paint. EVEN BETTER...Insurance (including Flood, Hurricane, and Hazard coverage) and Exterior Building Maintenance/Repairs, are all included in the monthly HOA fee, creating a truly low-stress ownership experience. Inside, the open-concept floor plan is bright, inviting, and effortlessly elegant. A soothing neutral palette, recessed LED lighting, solid-core doors with iron hardware, and wood-look luxury vinyl plank flooring throughout create a sophisticated, modern, and allergen-friendly living environment. The expansive eat-in kitchen is designed for both everyday living and entertaining. Features include GE stainless steel appliances, a slide-in 5-burner convection range, exterior-vented architectural hood, French-door refrigerator with bottom freezer, custom cabinetry with crown molding, soft-close hardware, dovetail drawers, and gorgeous quartzite countertops with a full-height backsplash. The adjacent dining area is enhanced by a custom buffet bar with lighted glass display cabinetry, offering both stylish storage and functionality. A spacious utility and storage area provides ample room for bikes, beach gear, and recreational equipment, along with a 2026 GE stackable washer and dryer for added convenience. Single-story living makes daily life effortless, while the covered carport includes a Tesla charging outlet. Outside, your private patio overlooks lush tropical landscaping, creating the perfect setting for morning coffee, outdoor dining, grilling, or simply relaxing in the Florida sunshine. Windward Bay offers an exceptional resort-style lifestyle on 26 beautifully landscaped bayfront acres. Residents enjoy three beach accesses, direct bay access, kayak and paddleboard launches and storage ($35/year), plus two marinas with boat slips available on a first-come, first-served basis for just $50/month. Owners may even install their own boat lift, as lifts are permitted. Community amenities include two heated pools, tennis courts, pickleball, shuffleboard, a clubhouse with fitness center, locker rooms, saunas, lending library, and a fully equipped catering kitchen with banquet hall for social gatherings and special events. The grounds stretch along nearly half a mile of Sarasota Bay and feature scenic walking and biking paths shaded by majestic banyan trees, accented by colorful bougainvillea and fragrant lemon trees. Windward Bay is both pet-friendly, allowing two pets up to 75 pounds each (for owners and renters!), and rental-friendly, permitting two leases per year with a one-month minimum. Adding another layer of confidence for buyers, the community has successfully completed its structural Milestone Inspection and has been re-certified for 10 years. This is a rare opportunity to own a fully renovated, move-in-ready villa that combines luxury, convenience, storm resilience, and carefree coastal living in one of Longboat Key's most desirable bay-to-beach communities.

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Christina Weger (941-773-4154)