Windward Bay Condos

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Overview

Below are all of the condos for sale in the Windward Bay condominium on Longboat Key Florida. All real estate listings are updated daily from the Multiple Listing Service (MLS).

To learn more about any of these condos or receive email updates when new listings hit the market, simply give us a call at 941-544-6467 or send us an email. We are here to help!

MLS® Listing Statistics

Total Listings: 9
Average Price: $728,200
Highest Price: $1,200,000
Lowest Price: $569,900
Average Size: 1,281 ft²
Average Price Per Square Foot: $568 per ft²

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Listings for Sale at Windward Bay

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4840 Gulf Of Mexico Drive Villa 15, LONGBOAT KEY, FL - $569,900

Residential, Villa
  • 2 Beds
  • 2 Baths
  • 1,084 SQFT
  • 26 DOM
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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 St...

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4600 Gulf Of Mexico Drive 202, LONGBOAT KEY, FL - $590,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,312 SQFT
  • 112 DOM
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Exciting Low Price - $590,000! Welcome To Your Bay Front Condo On Longboat Key, Where Every Day Begins With Breathtaking Sunrises And Panoramic Views Of Sarasota Bay. This Updated And Partially Furnished 2-bedroom, 2-bathroom Residence Features Ea...

4760 Gulf Of Mexico Dr. Villa 7, LONGBOAT KEY, FL - $595,000

Residential, Villa
  • 2 Beds
  • 2 Baths
  • 931 SQFT
  • 70 DOM
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Brand New Beach & Bay Villa! Renovated With Precision, The Final Finishing Touches Were Completed March 26, 2025 For This Quality Engineered, Down To The Studs, Two-bedroom And Two-bath Beach Getaway Villa. From The Moment You Step Inside, You'll ...

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4800 Gulf Of Mexico Drive Ph 3, LONGBOAT KEY, FL - $599,900

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,312 SQFT
  • 174 DOM
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Perched Above It All, This 2 Bedroom 2 Bath Penthouse Residence Offers Breathtaking And Sweeping Bayfront Views As Well As The Enchantment Of The Sparkling Evening City Lights. Featuring Walls Of Expansive Pgt Hurricane Windows, Bathing The Space...

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4500 Gulf Of Mexico Drive Ph4, LONGBOAT KEY, FL - $675,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,312 SQFT
  • 42 DOM
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Exquisite Waterfront Penthouse Condo With Stunning Water Views From Every Window Nestled In The Heart Of A Vibrant Longboat Key Community, This Stunning 2-bedroom, 2-bathroom Condo Offers Unparalleled Water Views Of Sarasota Bay, Creating A Perfe...

Image 5: A4632746

4900 Gulf Of Mexico Drive 205, LONGBOAT KEY, FL - $725,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,312 SQFT
  • 171 DOM
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Beauty On The Bay Will Be Found In This Delightful 2 Bedroom 2 Bath Condo At Windward Bay. In Fact, One Of The Very Few Units Currently On The Market At Windward Bay With All Assessments Fully Paid Off, Including The 15 Year Community Capital Impr...

4800 Gulf Of Mexico Drive 205, LONGBOAT KEY, FL - $799,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,325 SQFT
  • 37 DOM
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Look No Further! This Is It! Designer Showplace! Behold The Quality Engineering, True Craftmanship, Curated High-end Finishes Of This Exquisitely Renovated, Highly Sought After, Two+ Bedroom Including Additional Queen Size Murphy Bed/guest Closet...

Image 7: A4636663

4600 Gulf Of Mexico Drive 206, LONGBOAT KEY, FL - $800,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,523 SQFT
  • 140 DOM
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Total Price Reduction Of $50,000! Inviting And Impeccably Maintained, This Large, Beautiful 2-bedroom, 2-bathroom Corner End-unit Condo (1,523 Sf) Is Incredibly Private And Offers Breathtaking Full Views Of Sarasota Bay From Every Room Through Flo...

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 DBA Stellar MLS.

Listing information last updated on June 19th, 2025 at 3:50pm EDT.

Map of Windward Bay

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