Windward Bay Condos

Windward Bay condos are a great, affordable option for waterview living on Longboat Key. With a beautiful view and beach access, individuals with Windward Bay real estate benefit from the Florida Keys lifestyle without a heavy pricetag. Read more about Windward Bay.

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For your private tour of residences available at Windward Bay, please contact Louis Wery.

Windward Bay

All Listings Under $100,000 $300,000 - $400,000
$400,000 - $500,000 $500,000 - $600,000 $600,000 - $700,000
1 – 6 of 20 Listings
Price, High to Low

3 Bed • 2 Bath • 1,422 Sf


4972 Gulf Of Mexico Dr #v20, Longboat Key

Come Enjoy This Rarely Available, Beautifully Remodeled 3-bedroom, 2-bathroom, Maintenance Free, Waterfront Residence In Longboat Key. This Open Co...

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Reduced 1%

2 Bed • 2 Bath • 1,312 Sf


4700 Gulf Of Mexico Dr #205, Longboat Key

Condo Extraordinaire In Windward Bay! “new” Can Be Used To Describe So Many Aspects Of This 2bd/2ba Bayfront, Picturesque Home. New Porcelain Tile ...

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2 Bed • 2 Bath • 1,533 Sf


4500 Gulf Of Mexico Dr #306, Longboat Key

Panoramic Water Views From This Large, Furnished 2 Bedroom, 2 Bathroom End Unit. In Your Master Retreat, Awaken To The Reflection Of The Sunrise On...

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2 Bed • 2 Bath • 1,312 Sf


4700 Gulf Of Mexico Dr #203, Longboat Key

You Will Enjoy Beautiful Views From Every Room Of This Lovingly Maintained And Never-rented Residence As Much As The Owners Have During Their Annua...

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New Listing

2 Bed • 2 Bath • 1,096 Sf


4600 Gulf Of Mexico Dr #202, Longboat Key

Picturesque And Serene! Upon Entry Into This Updated 2bd/2ba Home You Are Immediately Drawn To The Bayfront Views That Are So Close You Feel As Th...

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2 Bed • 2 Bath • 1,149 Sf


4960 Gulf Of Mexico Dr #204, Longboat Key

This Lovely Residence Has Been Updated With New Tile Floors In The Foyer, Kitchen, And In The Spacious Lanai Which Features Newer Windows And Honey...

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  • Clubhouse
  • Dock
  • Elevator
  • Fitness center
  • Assigned Under-building Parking
  • His/Hers Saunas
  • Suffleboard Courts
  • Two Heated Swimming Pools
  • Tennis Courts


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All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS.

Listing information last updated on November 21st, 2017 at 2:20pm EST.

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