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4600 Gulf Of Mexico Drive Unit 206, Longboat Key
$701,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
$50,000 PRICE IMPROVEMENT – Exceptional Luxury Bayfront Value on Longboat Key! Now offered at an incredible new price, this beautifully updated large END-UNIT condo presents a rare opportunity to own premier bayfront living in Windward Bay. Experience elevated Longboat Key bayfront living in this BEAUTIFULLY UPDATED and impeccably maintained 2-bedroom, 2-bathroom corner END-UNIT condo in the sought-after Windward Bay community. This ELEGANT RESIDENCE offers unobstructed full Sarasota Bay VIEWS from nearly every room through dramatic floor-to-ceiling windows. Exceptionally PRIVATE and boasting the LARGEST FLOOR PLAN in the community, this condo is located on the second floor with convenient elevator access - perfectly blending comfort, sophistication and coastal serenity. The open-concept kitchen features Italian quartz countertops, stainless steel appliances, a large breakfast island and 42"cabinetry with elegant, iridescent Mother-of-Pearl backsplash that flows seamlessly into the great room with tranquil water views. PORCELAIN tile flooring THROUGHOUT enhances the modern coastal aesthetic. The bayfront primary suite is a peaceful retreat and offers direct lanai access, a generous walk-in closet, and a luxurious ensuite bath with custom walk-in shower and dual-sink vanity. The second bedroom also enjoys bay views and lanai access, making it ideal for guests or a home office, and sits adjacent to updated guest bathroom. Additional conveniences include brand new in-unit laundry, private storage, and under-building parking. Recent upgrades include PGT hurricane-impact windows, including a premium, single pane panoramic window in the great room, a 2021 HVAC system, and a 2020 water heater. The monthly HOA fee of $1,325 includes hazard, hurricane and flood insurance, recreational amenities and FULLY FUNDED RESERVES - major value for bayfront condo ownership. There is a modest assessment $293 per month at a low interest rate. Windward Bay spans 26 acres of waterfront and offers resort-style amenities including BOAT SLIPS, kayak storage, three private beach access points, two heated pools, a fitness center, saunas, tennis and pickleball courts, walking paths, BBQ grills, fire pits, and a clubhouse. The community is PET FRIENDLY, allowing two pets up to 75 lbs each, and approved renter pets, making this an excellent primary residence, vacation home, or investment property. Located mid-island, you are minutes from championship golf, full-service marinas, St. Armands Circle, downtown Sarasota, and Anna Maria Island. Whether you are seeking a luxury Longboat Key waterfront condo, a serene island retreat or a strong rental opportunity, this exceptional bayfront residence delivers the ultimate coastal lifestyle!

4600 Gulf Of Mexico Drive Unit 206, Longboat Key
4500 Gulf Of Mexico Drive Unit 3, Longboat Key
$685,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
GORGEOUS BAYFRONT PENTHOUSE VIEWS--RARE TOP FLOOR OPPORTUNITY!! Nestled in the heart of a vibrant Longboat Key Community, this stunning two-bedroom, two-bathroom condo offers unparralled water views of Sarasota bay, creating a great backdrop for both sunrises and sunsets. Step inside and be captivated by the breathtaking scenery and spacious design that blends coastal living with sophistication. Beautifully renovated with new floor to ceiling hurricane windows, this condo seamlessly integrates the living and dining areas with an open kitchen featuring stone countertops, custom cabinets and new Stainless steel appliances. The light-filled primary bedroom boasts two closets, one being a walkin complete with built in ample storage. Both bathrooms have been tastefully renovated, offering a spa-like ambiance that invites relaxation. Take in manatee and dolphin viewing from the expansive Florida Room or relax in style looking out the huge picture window as the sun rises over the bay. This professionally managed, pet friendly community offers an array of amenities including 26 acres of landscaped ground, 2 marinas, 2 heated pools, tennis courts, pickle ball courts, state-of-the art Fitness Center, library and Community Clubhouse. Take advantage of the Deeded Beach Access just steps away. With its prime location, stunning views and extensive amenities, this property represents a rare opportunity to embrace the best of waterfront living.

4500 Gulf Of Mexico Drive Unit 3, Longboat Key
4900 Gulf Of Mexico Drive Unit 203, Longboat Key
$671,500
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
A BAYFRONT BEAUTY! VIEWS THAT STEAL THE SHOW! Discover the ultimate in Florida Gulf-to-Bay living with this beautifully remodeled 2-bedroom, 2-bath luxury condo offering jaw-dropping, multi-million-dollar water views of Sarasota Bay. From the moment you enter, you’ll be drawn into a world where comfort, beauty and the quiet grace of nature welcomes you like an old friend. Wake up to spectacular sunrises over the sparkling bay and unwind with mesmerizing sunsets on the Gulf, directly across the street. Watch playful dolphins, jumping fish, gentle manatees, and vibrant Florida birdlife from your Florida Room or while preparing meals in your updated kitchen overlooking the shimmering waters. Your primary suite is a serene waterfront retreat, perfect for moonlit nights and sunrise mornings. Every detail of this condo has been thoughtfully designed to create a lifestyle of tranquility and relaxation, including remote controlled blinds in the Florida Room. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. From dolphins at dawn to sunsets on the Gulf—every day is paradise. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. The Windward Bay Association has been busy with a multitude of improvements and updates in the last few years including: Brand new roofs, resealing the buildings bayfront exteriors and painting of all the midrises in 2023/2024. Private roads were repaved and a new 1/2 mile long salt-tolerant privacy hedge was planted in October 2025. 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 and 2026 Condo Fees only increased by $13 a month. This is more than a home—it’s a lifestyle. Experience the beauty, serenity, convenience, and the maintenance free life you’ve always dreamed of. GREAT NEWS, PAST CAPITAL IMPROVEMENT ASSESSMENTS WERE PAID IN FULL BY SELLER, NOT ADDED TO MONTHLY DUES! Schedule your private showing today and make paradise yours!

4900 Gulf Of Mexico Drive Unit 203, Longboat Key
4900 Gulf Of Mexico Drive Unit 205, Longboat Key
$670,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
Breathtaking full bay views greet you as you enter this delightful 2 Bedroom 2 bath condo at Windward Bay. The interior has been freshly painted and fully updated with brand new Luxury Vinyl Plank flooring and Moen plumbing fixtures. The Unit boasts granite countertops and Brookhill custom wood cabinets in kitchen and baths, GE Profile double oven, Bosch stacking washer/dryer, Hunter Douglas window treatments, large walk-in master bed closet, hurricane impact windows, and Honeywell WiFi thermostat with humidity control. Enjoy the stunning waterfront views as you dine or relax on your private lanai. Windward Bay is a low density, pet friendly community nestled on 26 acres with 1/2 mile of waterfront trails and 3 adjacent beach accesses. (1deeded,2public). It enjoys a prime mid key location near dining, shopping, and world class entertainment in St Armand's Circle, Sarasota, and Anna Maria Island. The property has many recent updates including new roofs, painting of the mid-rises and extensive landscaping. Its numerous amenities include 2 heated pools, tennis and pickleball courts, 2 marinas with 28 boat slips, kayak racks and launches, covered parking, grills, firepits, and seating areas throughout, and a clubhouse with kitchen, meeting room, fitness center, 2 saunas, and a library. One of the very few units at Windward Bay with ALL of its assessments having been fully paid, including the 15 year Community Capital Improvement and the 30 year Longboat Key undergrounding. For added security, the State of Florida Milestone Inspection on all buildings is complete and Windward Bay is certified for an additional 10 years. Whether your're considering a getaway, a new home, or a rental property, don't miss this great opportunity to own your piece of paradise.

4900 Gulf Of Mexico Drive Unit 205, Longboat Key
4500 Gulf Of Mexico Dr Unit 305, Longboat Key
$650,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
Experience breathtaking Sarasota Bay views from every room in this beautifully customized Windward Bay condominium. This coastal retreat offers a seamless blend of elegance and comfort, featuring designer upgrades and thoughtful touches throughout. The open-concept living area is centered around a stunning custom fireplace — a feature that adds warmth and character to the space. Walls of windows fill the home with natural light and frame serene, panoramic bay and marina views, where dolphins, manatees, and pelicans glide across the water. The modern kitchen is equipped with stainless steel appliances and stylish finishes, while the spacious primary suite includes a generous walk-in closet and dressing area. Step onto the enclosed lanai, tiled underfoot, and savor peaceful mornings watching the sunrise over the bay. Every detail has been carefully curated — from updated flooring and custom woodwork to contemporart fixtures and generous storage throughout. Residents of pet friendly Windward Bay enjoy resort-style amenities including two heated pools, tennis and pickleball courts, fitness center, marinas with boat slips(fee and wait list), kayak storage, and deeded beach access just across the street. Perfectly located near Bayfront Park, shopping, dining, and St. Armands Circle, this home offers the best of Longboat Key living — tranquil, refined, and unmistakably coastal. Welcome home to the kind of life you don't just dream of-you live it here!

4500 Gulf Of Mexico Dr Unit 305, Longboat Key
4500 Gulf Of Mexico Drive Unit 202, Longboat Key
$650,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
UNDER CONTRACT. ACCEPTING BACKUP OFFERS.Wake up to shimmering Bay views and peaceful marina life in this updated, turnkey furnished, 2-bed, 2-bath Longboat Key retreat on 26 bayfront acres, with half a mile of walking trails along the Bay. This 1,312 sq ft residence features an open coastal layout, a bright remodeled kitchen with quartz countertops, and an oversized living area designed to frame the waterfront views. Step into the lanai and look out over the marina, mangroves, and wildlife — a tranquil backdrop that changes with the tides. The building’s rare pet policy allowing two pets, combined with its waterfront lifestyle, makes this one of the most desirable opportunities on Longboat Key. Enjoy beach access, 2 heated pools, 6 pickleball courts and tennis courts, kayak storage, bike storage, walking trails, fitness amenities, firepits, barbecue grills, picnic tables, 2 marinas, fishing piers, shuffleboard, clubhouse with a kitchen, library, fitness room, meeting room, 2 saunas, and walkability to restaurants. Whether you’re seeking a seasonal escape or a full-time coastal home, #202 delivers a relaxed, elevated lifestyle with a view you’ll never forget.

4500 Gulf Of Mexico Drive Unit 202, Longboat Key
4960 Gulf Of Mexico Drive Unit 206, Longboat Key
$644,950
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
Public showings are now available for the first time. After months of restricted access due to a tenant, this residence is finally available for public showings. Restricted access resulted in only a handful of private showings, giving today’s buyers a rare chance to discover a home that’s been under the radar. Unbeatable opportunity at $649,900 for a full Bayfront Waterview, corner end-unit on Longboat Key. Exceptionally priced below market value—this residence represents the lowest-priced Bayfront end unit in the highly desirable community of Windward Bay, in over 5 years. A compelling price point, providing rare access for those seeking to own a premium waterfront residence at an extraordinary price. Encompassing 1,523 square feet, this stylishly furnished, two-bedroom, two-bath residence is thoughtfully designed to showcase uninterrupted panoramic Bay views from every room. Natural light fills the open living and dining areas, where expansive windows frame ever-changing Bay views from sunrise through the evening’s sunset. The remodeled 2024 kitchen opens seamlessly to the main living area and features recently completed upper cabinetry and a sophisticated yet functional layout ideal for both relaxed daily living and entertaining. Recently acquired “chic” French doors in both bedrooms open to the Florida Room, a signature feature for Longboat Key residences, offering additional living space to enjoy morning light and serene Bay vistas. The spacious primary suite includes a private en-suite bath and a generous walk-in closet, providing comfort, supporting everyday living, and abundant storage. “Pet Friendly” Windward Bay is a well-established waterfront community known for its mature landscaping, waterfront setting, resort-style amenities, a strong proactive association with solid reserves, and an enduring reputation as one of Longboat Key’s most welcoming communities. (Attributes that continue to attract owners who value lifestyle as much as long-term stability.) The Milestone Inspection and Capital Reserve Study are complete. Windward Bay’s Monthly Condo Fees for 2025 were actually reduced and for 2026 only increased slightly by $13 a month, demonstrating a financially healthy Condo Association. Offered furnished and move-in ready, this corner end-unit provides flexibility as a full-time residence, seasonal retreat, or investment opportunity. From dolphins at dawn to sunsets on the Gulf—every day is paradise. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. An uncommon offering distinguished by exceptional value, location, and the timeless appeal of gulf to bay living. Private showings are available for those seeking a rare chance to own a premium waterfront residence at an extraordinary price.

4960 Gulf Of Mexico Drive Unit 206, Longboat Key
4960 Gulf Of Mexico Drive Unit 204, Longboat Key
$585,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
Welcome to your dream retreat! This exquisite two-bedroom, two-bathroom condominium offers an unparalleled living experience, nestled within an amenity-rich community that defines coastal luxury. Picture yourself waking up to breathtaking marina views, with every window framing a picturesque panorama that will leave you in awe. As you step inside, you will notice the seamless blend of modern updates and timeless comfort. The open-concept living space is accentuated by floor-to-ceiling viewing windows, bathing the interior in natural light while providing unobstructed views of the tranquil waters. The updated kitchen is equipped with new cabinets, stone counters while the spacious primary suite includes a generous walk-in closet and dressing area. Both bathrooms have been tastefully renovated, offering a spa-like ambiance that invites relaxation. Beyond the walls of your stunning condo, this professionally managed, pet friendly community encompasses 26 acres of beautifully landscaped grounds, providing a serene environment for leisure and recreation. Enjoy life to the fullest with an impressive array of amenities at your fingertips. Take advantage of the deeded beach access just steps away, where sun-soaked days and salty breezes await you. The community clubhouse serves as a hub for social gatherings, while two inviting pools provide refreshing escapes on warm afternoons. For the active lifestyle enthusiast, there are boat slips and kayak launches ready for your aquatic adventures, along with tennis and pickleball courts to keep you engaged and fit. Miles of walking trails weave through the property, perfect for leisurely strolls or invigorating jogs amidst nature’s beauty. This condominium isn't just a home; it's a lifestyle. With its prime location, stunning views, and extensive amenities, this property represents a rare opportunity to embrace the best of waterfront living. Don’t miss your chance to make this beautiful bayfront condo your own. Schedule a private showing today and experience the allure for yourself!

4960 Gulf Of Mexico Drive Unit 204, Longboat Key
4800 Gulf Of Mexico Drive Unit PH3, Longboat Key
$537,500
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
Sold Data Entry Only

4800 Gulf Of Mexico Drive Unit PH3, Longboat Key
12329 49th Street East, Parrish
$489,268
4 Beds ⋅ 3 Baths ⋅ Windward Bay SubDv. ⋅ 34219 Zip Code
Sold Data Entry Only.

12329 49th Street East, Parrish
4500 Gulf Of Mexico Drive Unit 203, Longboat Key
$400,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
Calling All Remodelers, Investors & Visionaries! Outstanding Value and a unique opportunity to reimagine a stunning coastal residence exactly as you envision it. Opportunity awaits in this Windward Bay 2-bedroom, 2-bath residence offering 1,325 square feet in one of Longboat Key's most desirable coastal communities. The kitchen and bathrooms are preserved in their original 1975 condition, an exciting opportunity to transform a time capsule into a showplace. Properties offering this level of renovation potential on Longboat Key are increasingly difficult to find. Roll up your sleeves and reap the rewards. A rare chance to create a completely personalized island retreat, a true blank canvas for a buyer with imagination and ambition. The floor plan offers excellent potential for a stunning modern transformation. With strong bones, generous living spaces, and an exceptional island location, this property is ready for its next chapter. For buyers who see potential where others see projects, this is your chance to renovate, redesign, and customize every finish to your exact vision. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Whether you're an investor seeking your next renovation project or a buyer eager to create a dream island getaway from the ground up, this condominium offers exceptional value, unlimited design potential, and the chance to secure a coveted Longboat Key lifestyle at an attractive price point, exceptional value and long-term upside. Bring your imagination and discover what this hidden gem can become.

4500 Gulf Of Mexico Drive Unit 203, Longboat Key
4840 Gulf Of Mexico Drive Unit Villa 15, Longboat Key
$399,999
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
Looking for a Beach/Bay Getaway Villa? LOCATION! LOCATION! LOCATION! This cozy End Unit Beach/Bay 2-bedroom/2-bath Sunny Villa boasts 1084 square feet of Longboat Key Florida Fun! Single story living with a convenient covered carport only a few steps away from your front door. Villa 15 is located directly across the street from the tranquil Gulf with its crystal-clear turquoise blue waters and uncrowded soft sandy beaches that attract visitors from all over the world. (Take joy with 3 beach access points, one private deeded) Enjoy walks along the shore, kayaking on the bay or read a book, unwind and soak up the sun on your own private patio while taking in the beauty of this incredible location. The patio is an ideal spot for morning coffee, watching a game of shuffleboard, hosting friends for sunset libations, evening grilling, or simply relaxing in solitude. Your beach/bay lifestyle possibilities are endless. Worry free living with recent Hurricane Impact Windows/Sliding Doors, Roof, & Carport (2020). As an added bonus with the sale of this Villa, the longtime owner since 1976, former Canadian Navy-Man, and a wonderful Nonagenarian, will be leaving most of his nautical treasures gathered from lands around the world for you to enjoy. Set like a jewel on the barrier island of Longboat Key, the community of Windward Bay is a magical wildlife haven nestled mid-island, flourishing on 26 acres and graced with 1/2 a mile of waterfront trails to relish. A low-density residence and a nature lover’s delight to gaze both frolicking dolphins and manatees as they play. Bird enthusiasts jubilate with their front-row seat of the magnificent Florida birds that call Windward Bay their home. Witness the vibrant plumage and graceful flights of these majestic creatures as they effortlessly navigate the glorious skies above. Windward Bay offers numerous amenities that make it an exceptional value including: 2 tennis/pickleball courts, 2 marinas with 28 boat & jet ski slips for a low monthly fee, 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. Monthly Condos Fees in 2025 were actually reduced and since 2024 have only increased by $2 a month. The Milestone Inspection and Capital Reserve Study are complete. THIS VILLA HAS NO PREVIOUS ASSESSMENT ADDED TO MONTHLY HOA FEES! This wonderful villa exemplifies “Florida Gulf to Bay Living” at its finest. Perfect for couples or individuals seeking paradise! Schedule your private tour today and make these experiences a reality.

4840 Gulf Of Mexico Drive Unit Villa 15, Longboat Key