Windward Bay Real Estate

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Windward Bay and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest Listings in Windward Bay

4600 Gulf Of Mexico Drive Unit 301, Longboat Key image

4600 Gulf Of Mexico Drive Unit 301, Longboat Key — E Building $660,000 ▼

Welcome to Paradise! Fall in love with this turnkey furnished two- bedroom two bath End Unit condo! Relax and enjoy beautiful unobstructed views of Sarasota Bay from nea...

2 Beds
2 Baths
Windward Bay SubDv.
34228 Zip Code

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

4800 Gulf Of Mexico Drive Unit PH 3, Longboat Key — Windward Bay $795,000 ▼

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.
34228 Zip Code

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.
34219 Zip Code

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.
34228 Zip Code

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

4750 Gulf Of Mexico Drive Unit Villa 8, Longboat Key — 'J' $649,900 ▼

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.
34228 Zip Code