Windward Bay

Longboat Key Condos for Sale


Windward Bay condos are located in a small complex on the Bayside at the northern end of Longboat Key. Owners are assigned covered parking spaces and also outside storage. They also have deeded beach access across the street. Boaters love the deep water boat dockage here which are available for a modest monthly fee.  Read More...

In addition to boating, residents enjoy walking, biking, shelling and sunbathing on this tropical island. Downtown Sarasota, Florida is within a short drive for cultural excursions to the ballet, opera, symphony, museums and theater. St. Armands Circle, also a short drive, is a shoppers paradise.

Building Amenities

  • Elevator
  • Two pools
  • Fitness Room
  • Tennis Courts
  • Parking
  Show Less...

Browse all condo listings currently available in Windward Bay on Longboat Key. Check out your options and call or email us if you would like details on any of these properties. You can also click the "Request More Info" button for a quick reply on any property.

Current Listings - Windward Bay Condominiums

Showing 1-9 of 9  | 
Page   of 1
$425,000
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1312
4700 Gulf Of Mexico Drive #303
Longboat Key, FL 34228
MLS #: A4209141
Subdivision: windward bay condo amd
When a Vacation home becomes a Place to Call Home. Welcome to Windward Bay, Building D with the best water views. After a WOW entry to this fully updated condo...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$414,900
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1312
4540 Gulf Of Mexico Drive #202 (Pending)
Longboat Key, FL 34228
MLS #: T2924427
Subdivision: windward bay condo amd
Pristine light and bright 2 BR/2BA condo with beautiful views from all rooms in a quiet location. Spend your mornings and evenings on the 22' lanai enjoying...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$409,000
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1312
4600 Gulf Of Mexico Drive #202
Longboat Key, FL 34228
MLS #: A4201897
Subdivision: windward bay condo amd
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 though you are...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$390,000
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1325
4960 Gulf Of Mexico Drive #A305
Longboat Key, FL 34228
MLS #: A4401652
Subdivision: windward bay condo amd
Love at first sight! Extraordinary bay views greet you as you enter this residence. The serene beauty of the water with the mainland in the distance will...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$385,000
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1561
4960 Gulf Of Mexico Drive #A206
Longboat Key, FL 34228
MLS #: A4215444
Subdivision: windward bay condo amd
Calling all boat lovers! This large end unit with over 1500 sq/ft overlooks Sarasota Bay AND one of the two community marinas. Whether loving the wind in your...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$350,000
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1561
4500 Gulf Of Mexico Drive #301 (Pending)
Longboat Key, FL 34228
MLS #: A4211441
Subdivision: windward bay condo amd
New Lower Price! This large 2 bedroom, 2 bathroom end unit with over 1500 sq/ft offers gorgeous water and sunrise views of Sarasota Bay and the community...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$339,500
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1312
4700 Gulf Of Mexico Drive #203 (Pending)
Longboat Key, FL 34228
MLS #: A4195618
Subdivision: windward bay condo amd
Enjoy beautiful water views from every room of this perfectly maintained, never-rented residence. The bright kitchen features a raised ceiling, new lighting,...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$330,000
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1312
4900 Gulf Of Mexico Drive #B305
Longboat Key, FL 34228
MLS #: A4215585
Subdivision: windward bay condo amd
Gorgeous, expansive, "so close you feel like you can touch the water" views of Sarasota Bay from this well located 2 bedroom, 2 bathroom condo. Great...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$314,900
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1523
4960 Gulf Of Mexico Drive #201 (Pending)
Longboat Key, FL 34228
MLS #: A4177049
Subdivision: windward bay condo amd
ACCEPTING BACK-UP CONTRACTS. Lowest priced residence at Windward Bay. Motivated Seller. Enjoy bay and marina views from this first floor (over parking)...
Contact Annette Smith at (941) 504-3922 to inquire about this property.

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