Windward Bay Condominiums, FL homes for sale & real estate

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4500 Gulf OF Mexico Dr #202, Longboat Key, FL 34228
4500 Gulf OF Mexico Dr #202, Longboat Key, FL 34228
4500 Gulf OF Mexico Dr #202, Longboat Key, FL 34228
ABOUT THIS HOME
Windward Bay Condominiums, FL Homes for Sale
Spectacular, unobstructed Bay views over the marina and mangrove islands AND the rare opportunity for 2 pets, a feature seldom available among condominiums on Longboat Key! This beach to bay, two-bedroom, two-bath condominium spans 1,312 s. f. and is ideally located across from the Zota Beach Resort, with 3 convenient beach access points. The new kitchen features quartz countertops and an open design that highlights the water views. The open-concept living room is framed by expansive windows overlooking the bay, marina and mangroves and flows seamlessly into the dining area and Florida room. The primary bedroom and second bedroom both capture magical bay views through the Florida room. The

$825,000

2 beds2 baths1,312 sq ft

4500 Gulf OF Mexico Dr #202, Longboat Key, FL 34228

Heated pools • Waterfront trails • New kitchen

OPEN SAT, 1PM TO 4PM

4800 Gulf OF Mexico Dr #205, Longboat Key, FL 34228
4800 Gulf OF Mexico Dr #205, Longboat Key, FL 34228
4800 Gulf OF Mexico Dr #205, Longboat Key, FL 34228
ABOUT THIS HOME
Windward Bay Condominiums, FL Homes for Sale
ASTONISHING SELLER BONUS OFER! Motivated Seller is offering to pay off remaining balance of the $26,490-7/1/2024 special assessment from list price at closing. LOOK NO FURTHER! THIS IS IT! A DESIGNER SHOWPLACE! Behold the quality engineering, true craftmanship, and curated high-end finishes of this exquisitely renovated, highly sought after, two+ bedroom condominium, including an additional Queen size Murphy Bed/Guest Closet situated in the Florida room. Instantly be captivated by the fusion of elegance and natural beauty coupled with an awe-inspiring Sarasota Bay View. The sheer scale of this impeccable remodel defies description. The open-concept floor plan allows for seamles

$768,000

2 beds2 baths1,325 sq ft

4800 Gulf OF Mexico Dr #205, Longboat Key, FL 34228

Deeded beach access • Waterfront trails • 2 marinas

OPEN SAT, 11AM TO 1PM

4840 Gulf OF Mexico Dr Unit Villa 15, Longboat Key, FL 34228
4840 Gulf OF Mexico Dr Unit Villa 15, Longboat Key, FL 34228
4840 Gulf OF Mexico Dr Unit Villa 15, Longboat Key, FL 34228
ABOUT THIS HOME
Windward Bay Condominiums, FL Homes for Sale
LOCATION! LOCATION! LOCATION! Looking for a Beach/Bay Getaway Villa? 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 loca

$524,900

2 beds2 baths1,084 sq ft

4840 Gulf OF Mexico Dr Unit Villa 15, Longboat Key, FL 34228

Heated pools • Waterfront trails • End unit

4800 Gulf OF Mexico Dr #204, Longboat Key, FL 34228
4800 Gulf OF Mexico Dr #204, Longboat Key, FL 34228
4800 Gulf OF Mexico Dr #204, Longboat Key, FL 34228
ABOUT THIS HOME
Windward Bay Condominiums, FL Homes for Sale
JAW-DROPPING WATER VIEWS! Revel & Relax as you experience amazing water views from every room of this inviting two-bedroom and two-bathroom condominium. Prepare to be enthralled by the mesmerizing beauty of the sparkling waters of Sarasota Bay, teaming with playful dolphins, graceful manatees, and the colorful spectacle of Florida's native birds. Witness spectacular sunrises, behold the magnificent moon while casting its illuminating reflection upon Sarasota Bay, all from this incredible place to call "home sweet home" or "home sweet second home. " Lovingly maintained and move-in ready with brand new hurricane windows and a new roof in 2023. Additional highlights i

$650,000

2 beds2 baths1,325 sq ft

4800 Gulf OF Mexico Dr #204, Longboat Key, FL 34228

Hurricane windows • Waterfront trails • Owner's closet

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Nearby homes that match your criteria

4545 Gulf Of Mexico Dr #511, Longboat Key, FL 34228
4545 Gulf Of Mexico Dr #511, Longboat Key, FL 34228
4545 Gulf Of Mexico Dr #511, Longboat Key, FL 34228
ABOUT THIS HOME
Windward Bay Condominiums, FL Homes for Sale
It's all about the breathtaking direct Gulf and Sarasota Bay views from this updated 2 bedroom/2 bath penthouse, located in the pet-friendly Castillian, on fabulous Longboat Key! Offering a wonderful blend of comfort and relaxation, this residence has been meticulously maintained and thoughtfully designed for immediate enjoyment. The eat-in kitchen seamlessly connects to the living/dining room, making entertaining a breeze. A bonus feature includes an in-residence washer and dryer, adding to the ease of beachfront living. The master suite, guest bedroom, and great room, open up to the beachfront terrace, bringing the serene landscape indoors. This residence is just 3 miles north of the Town

$1,050,000

2 beds2 baths1,398 sq ft

4545 Gulf Of Mexico Dr #511, Longboat Key, FL 34228

$1,333 HOA • Garage • Community pool

5005 Gulf OF Mexico Dr #5, Longboat Key, FL 34228
5005 Gulf OF Mexico Dr #5, Longboat Key, FL 34228
5005 Gulf OF Mexico Dr #5, Longboat Key, FL 34228
ABOUT THIS HOME
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

$4,599,000

4 beds4.5 baths4,044 sq ft

5005 Gulf OF Mexico Dr #5, Longboat Key, FL 34228

0.23 acre lot • $571 HOA • 3 garage spots

4725 Gulf OF Mexico Dr #212, Longboat Key, FL 34228
4725 Gulf OF Mexico Dr #212, Longboat Key, FL 34228
4725 Gulf OF Mexico Dr #212, Longboat Key, FL 34228
ABOUT THIS HOME
Windward Bay Condominiums, FL Homes for Sale
PRICE IMPROVEMENT! 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

$875,000

2 beds2 baths1,071 sq ft

4725 Gulf OF Mexico Dr #212, Longboat Key, FL 34228

4.94 acre lot • $1,466 HOA • Community pool

4805 Gulf OF Mexico Dr #105, Longboat Key, FL 34228
4805 Gulf OF Mexico Dr #105, Longboat Key, FL 34228
4805 Gulf OF Mexico Dr #105, Longboat Key, FL 34228
ABOUT THIS HOME
Windward Bay Condominiums, FL Homes for Sale
Experience direct Gulf-front living in this turnkey-furnished, first-floor walkout residence at The Westchester on Longboat Key. Enjoy turquoise water views from nearly every room, with miles of pristine beach just outside your door. This two-bedroom, two-bath condominium is tastefully decorated in a coastal style and features a spacious split floor plan designed for comfort and privacy, along with seamless indoor-outdoor access to the pool and beach. The living and dining areas include a built-in entertainment center and serving buffet. The kitchen is appointed with stainless steel appliances, generous counter space, and abundant storage. Both bedrooms offer en suite baths and generous wal

$725,000

2 beds2 baths1,393 sq ft

4805 Gulf OF Mexico Dr #105, Longboat Key, FL 34228

$1,998 HOA • Community pool • Car-dependent

4420 Exeter Dr Unit L303, Longboat Key, FL 34228
4420 Exeter Dr Unit L303, Longboat Key, FL 34228
4420 Exeter Dr Unit L303, Longboat Key, FL 34228
ABOUT THIS HOME
Windward Bay Condominiums, FL Homes for Sale
Significant Reduction ! Enjoy breathtaking water views from most rooms in this beautifully renovated top-floor 2-bedroom, 2-bath condo located on the 3rd floor of the highly desirable Longboat Harbour community. Styled with a touch of French flair, the interior features plush velvety carpet throughout—luxurious underfoot and easy on the knees. The kitchen is outfitted with sleek stainless steel appliances, and both bathrooms have been tastefully updated. Impact windows provide peace of mind, and a stacked washer and dryer are conveniently located inside the unit. Offered fully furnished, this home is completely move-in ready. Longboat Harbour is a vibrant waterfront community offerin

$675,000

2 beds2 baths1,152 sq ft

4420 Exeter Dr Unit L303, Longboat Key, FL 34228

$1,351 HOA • Community pool • Car-dependent

4380 Exeter Dr #204, Longboat Key, FL 34228
4380 Exeter Dr #204, Longboat Key, FL 34228
4380 Exeter Dr #204, Longboat Key, FL 34228
ABOUT THIS HOME
Windward Bay Condominiums, FL Homes for Sale
Make your dreams come true with this beautiful waterfront condominium located at the popular Longboat Harbour resort! Enjoy gorgeous views of the water the moment you step in. This newly renovated 2BD/2BA second floor unit offers a roomy open floor plan with plenty of natural light, is being sold turnkey furnished. New Luxury Vinyl flooring and hurricane windows has been installed throughout. The updated kitchen has Granite countertops and new appliances. Benefit from your own private washer and dryer located in the guest bathroom. The inclusive patio with new sliders oversees the canal as well as a partial view of the gulf. One assigned covered parking space is included. Sorry, no pets are

$579,000

2 beds2 baths992 sq ft

4380 Exeter Dr #204, Longboat Key, FL 34228

$1,351 HOA • Community pool • Car-dependent

Property at 4621 Gulf OF Mexico Dr Unit 2F, Longboat Key, FL 34228, 2 beds, 2 baths

$625,000

2 beds2 baths756 sq ft

4621 Gulf OF Mexico Dr Unit 2F, Longboat Key, FL 34228

Property at 4835 Gulf OF Mexico Dr #106, Longboat Key, FL 34228, 2 beds, 2 baths

$800,000

2 beds2 baths1,393 sq ft

4835 Gulf OF Mexico Dr #106, Longboat Key, FL 34228

Property at 4765 Gulf OF Mexico Dr Unit B202, Longboat Key, FL 34228, 3 beds, 3.5 baths

$5,995,000

3 beds3.5 baths3,368 sq ft

4765 Gulf OF Mexico Dr Unit B202, Longboat Key, FL 34228

Property at 4835 Gulf OF Mexico Dr Unit 302B, Longboat Key, FL 34228, 2 beds, 2 baths

$1,150,000

2 beds2 baths1,393 sq ft

4835 Gulf OF Mexico Dr Unit 302B, Longboat Key, FL 34228

Property at 4621 Gulf OF Mexico Dr Unit 19B, Longboat Key, FL 34228, 2 beds, 2 baths

$675,000

2 beds2 baths900 sq ft

4621 Gulf OF Mexico Dr Unit 19B, Longboat Key, FL 34228

Property at 4621 Gulf OF Mexico Dr Unit 16B, Longboat Key, FL 34228, 2 beds, 2 baths

$720,000

2 beds2 baths900 sq ft

4621 Gulf OF Mexico Dr Unit 16B, Longboat Key, FL 34228

Property at 4651 Gulf OF Mexico Dr #402, Longboat Key, FL 34228, 4 beds, 4.5 baths

$5,999,000

4 beds4.5 baths3,989 sq ft

4651 Gulf OF Mexico Dr #402, Longboat Key, FL 34228

Based on information submitted to the MLS GRID as of Thu Sep 11 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Average home prices near Windward Bay Condominiums, FL

Cities

Windward Bay Condominiums, FL real estate trends

$565K

Sale price

$382

Sale $/sq ft

Under list price

10.9%

Days on market

145

Down payment

—

Total homes sold

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