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: 11
Average Price: $670,364
Highest Price: $800,000
Lowest Price: $499,000
Average Size: 1,304 ft²
Average Price Per Square Foot: $523 per ft²

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Listings for Sale at Windward Bay

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Image 0: A4652683

4840 Gulf Of Mexico Drive Villa 15, LONGBOAT KEY, FL - $499,000

Residential, Villa
  • 2 Beds
  • 2 Baths
  • 1,084 SQFT
  • 235 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...

4860 Gulf Of Mexico Drive Villa 13, LONGBOAT KEY, FL - $510,000

Residential, Villa
  • 2 Beds
  • 2 Baths
  • 1,025 SQFT
  • 13 DOM
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This Exquisite Turnkey Furnished 2-bed, 2-bath Villa Has Been Fully And Meticulously Renovated—not A Detail Overlooked, Not An Expense Spared. Step Inside And Instantly Feel The Difference: An Open-concept Layout, A Serene Neutral Palette, Elegant...

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

Residential, Villa
  • 2 Beds
  • 2 Baths
  • 931 SQFT
  • 61 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 ...

Image 3: A4667631

4540 Gulf Of Mexico Drive 204, LONGBOAT KEY, FL - $649,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,312 SQFT
  • 96 DOM
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Welcome To Your Island Retreat, An Impeccably Renovated 2-bedroom, 2-bath Residence Offering Luxury Longboat Key Living At Its Finest With Preserved Mangrove And Sarasota Bay Views. Every Detail Has Been Thoughtfully Updated ,this Home Has Been Re...

Image 4: A4677420

4960 Gulf Of Mexico Drive 204, LONGBOAT KEY, FL - $650,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,096 SQFT
  • 0 DOM
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Welcome To Your Dream Retreat! This Exquisite Two-bedroom, Two-bathroom Condominium Offers An Unparalleled Living Experience, Nestled Within An Amenity-rich Community That Defines Coastal Luxury. Picture Yourself Waking Up To Breathtaking Marina V...

Image 5: A4664363

4500 Gulf Of Mexico Drive 202, LONGBOAT KEY, FL - $695,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,312 SQFT
  • 127 DOM
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Price Reduced To Sell! Seller Says All Offers Considered. Wake Up To Shimmering Bay Views And Peaceful Marina Life In This Updated, Turnkey Furnished, 2-bed, 2-bath Longboat Key Retreat On 26 Bayfront Acres, With Half A Mile Of Walking Trails Alon...

Image 6: A4671087

4900 Gulf Of Mexico Drive 205, LONGBOAT KEY, FL - $698,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,312 SQFT
  • 68 DOM
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Breathtaking Full Bay Views Greet You As You Enter This Delightful 2 Bedroom 2 Bath Condo At Windward Bay. The Interior Has Been Freshly Painted And Fully Updated With Brand New Luxury Vinyl Plank Flooring And Moen Plumbing Fixtures. The Unit Boa...

Image 7: A4665034

4976 Gulf Of Mexico Drive Villa 18, LONGBOAT KEY, FL - $725,000

Residential, Condominium
  • 3 Beds
  • 2 Baths
  • 1,900 SQFT
  • 79 DOM
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This Spacious Waterfront Villa Lives Like A Single-family Home Yet Offers The Ease Of Maintenance-free Living! Enjoy Breathtaking Sarasota Bay And Canal Views From This 1,900 Sq. Ft. Residence—the Largest In The Community. Thoughtfully Designed,...

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 January 15th, 2026 at 5:10pm EST.

Map of Windward Bay

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