Windward Bay Real Estate

Welcome to Windward Bay, a picturesque subdivision located in the sunny state of Florida. This charming community offers a unique blend of tranquility and convenience, making it an ideal place to call home.

Situated in the heart of Florida, Windward Bay is known for its beautiful homes, lush green spaces, and close-knit atmosphere. Residents here enjoy a peaceful lifestyle with easy access to a variety of amenities, including shopping centers, restaurants, and top-rated schools.

One of the highlights of Windward Bay is its proximity to the stunning beaches of Florida's Gulf Coast. Residents can spend their days soaking up the sun, swimming in the crystal-clear waters, or simply relaxing on the sandy shores.

In addition to its natural beauty, Windward Bay also offers a range of recreational activities for residents to enjoy. From community parks and playgrounds to walking and biking trails, there is something for everyone to explore and experience.

Whether you are looking to raise a family, retire in style, or simply enjoy the Florida lifestyle, Windward Bay has something for everyone. Come and discover the beauty and charm of this vibrant community – you may just find your perfect place to call home.

Newest Listings in Windward Bay

4540 Gulf Of Mexico Drive Unit 204, Longboat Key image

4540 Gulf Of Mexico Drive Unit 204, Longboat Key — F $595,000

Welcome to your island retreat, an impeccably renovated 2-bedroom, 2-bath residence offering the best of Longboat Key living with beautiful views of the preserved mangrov...

2 Beds
2 Baths
Windward Bay SubDv.

4800 Gulf Of Mexico Drive Unit PH 3, Longboat Key image

4800 Gulf Of Mexico Drive Unit PH 3, Longboat Key — Windward Bay $799,999

Welcome to your Longboat Key PENTHOUSE, where unobstructed PANORAMIC WATER VIEWS from every room create a breathtaking backdrop from the moment you walk through the door....

2 Beds
2 Baths
Windward Bay SubDv.

5322 124th Avenue E, Parrish $755,000 ▼

NO CDD-GATED-HALF ACRE+POOL&SPA Welcome to Windwater, one of Parrish’s gated communities offering spacious homesites, community amenities, and no CDD fees. Built in 2025 ...

4 Beds
3 Baths
Windward Bay SubDv.

4825 Gulf Of Mexico Drive Unit 504, Longboat Key image

4825 Gulf Of Mexico Drive Unit 504, Longboat Key — C504 $725,000 ▼

Discover coastal living at its finest in this beautifully positioned 2-bedroom, 2-bath condominium on one of Longboat Key’s most sought-after stretches. This residence of...

2 Beds
2 Baths
Windward Bay SubDv.

1882 Tarpon Bay Drive S Unit 101, Naples image

1882 Tarpon Bay Drive S Unit 101, Naples $364,000 ▼

Rarely available three-bedroom, two-bath first-floor end residence in the active, gated community of Tarpon Bay. This residence features tile flooring, a desirable split ...

3 Beds
2 Baths
Windward Bay SubDv.

4720 Gulf Of Mexico Drive Unit Villa 2, Longboat Key image

4720 Gulf Of Mexico Drive Unit Villa 2, Longboat Key — K $585,000 ▼

Completely renovated two-bedroom and two-bathroom walkout (no stairs to take) on Longboat Key! Welcome to coastal luxury living in Windward Bay, one of Longboat Key's mos...

2 Beds
2 Baths
Windward Bay SubDv.

4750 Gulf Of Mexico Drive Unit Villa 8, Longboat Key image

4750 Gulf Of Mexico Drive Unit Villa 8, Longboat Key — 'J' $680,000 ▼

THE BAY! THE GULF! THE BEST OF BOTH! Imagine a place where every day begins with the peaceful beauty of Longboat Key's sparkling bay and ends beneath the breathtaking col...

3 Beds
2 Baths
Windward Bay SubDv.

4500 Gulf Of Mexico Drive Unit 206, Longboat Key image

4500 Gulf Of Mexico Drive Unit 206, Longboat Key — G-Building $769,000 ▼

This residence is now available for public and private showings. "One Chance! One Corner-End Condo! One Dream! Don’t Let It Slip Away!” Restricted access resulted in onl...