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
7 – 12 of 14 Listings
Price, High to Low

3 Bed • 2 Bath • 1,422 Sf


4810 Gulf Of Mexico Dr, Longboat Key

Seasonal. This Tastefully Appointed, Completely Renovated 3 Bedroom/2 Full Bath, End-unit Villa Offers Partial Bay View And Provides All The Comfor...

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2 Bed • 2 Bath • 1,312 Sf


4960 Gulf Of Mexico Dr #ph4, Longboat Key

Bayside Vacation Rental Close To Pool And Beach. Newly Updated With Fabulous Views Of Sarasota Bay From Living Rooms, Bedrooms And Glassed Lanai I...

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2 Bed • 2 Bath • 1,312 Sf


4500 Gulf Of Mexico Dr #g302, Longboat Key

Expansive Views Of Sarasota Bay From This Spacious Bay Front 1,300 S.f., 2-bedroom, 2-bath 3rd Floor Condo. Dolphin, Manatee And Osprey Sightings ...

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2 Bed • 2 Bath • 1,312 Sf


4900 Gulf Of Mexico Dr #b-204, Longboat Key

Bayside Seasonal Rental With Full Bay View - - Full Bay Views Of Sarasota Bay From Every Room In This Preferred "building B" Location At Windward B...

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2 Bed • 2 Bath • 1,096 Sf


4540 Gulf Of Mexico Dr #f-303, Longboat Key

Gorgeous Bay Views - Monthly Rental Available. Spacious Bayside 2-bedroom, 2-bath Condo Close To The Beach. Sweeping Bay Views From This Quiet Re...

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Reduced 16%

2 Bed • 2 Bath • 1,334 Sf


4820 Gulf Of Mexico Dr #10, Longboat Key

Seasonal: Rare Windward Bay 3 Bedroom Ground Floor Villa With A Spacious, Bright And Open Floor Plan. Completely Updated Interior With Granite, Sto...

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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 September 21st, 2018 at 5:31pm EDT.

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