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 of Windward Bay 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.

View Current Listings - Windward Bay

Showing 1-10 of 10  | 
Page   of 1
$465,000
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1337
4600 Gulf Of Mexico Drive #301 (Pending)
Longboat Key, FL 34228
MLS #: A4169240
Subdivision: windward bay condo amd
Located in one of the most preferred buildings in the very desirable pet-friendly Windward Bay, this renovated third floor end unit enjoys big bay views...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$464,000
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1312
4800 Gulf Of Mexico Drive #PH3
Longboat Key, FL 34228
MLS #: A4183170
Subdivision: windward bay condo amd
Arrival into this 2BD/2BA penthouse has the feel of sitting on the balcony of a cruise ship with sites of land in the distance, and nothing but calming waters...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$459,000
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1325
4800 Gulf Of Mexico Drive #302
Longboat Key, FL 34228
MLS #: A4166724
Subdivision: windward bay condo amd
Not many places can claim ability to capture the serene beauty of Sarasota Bay on such a grandeur scale; but this one can! The view is apparent and striking...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$422,500
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1096
4600 Gulf Of Mexico Drive #202
Longboat Key, FL 34228
MLS #: A4169400
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.
$420,000
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1561
4900 Gulf Of Mexico Drive #301
Longboat Key, FL 34228
MLS #: A4179881
Subdivision: windward bay condo amd
Enjoy stunning views of Sarasota Bay from every room in this preferred "Building B" location at Windward Bay, a 25-acre bayside community on beautiful Longboat...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$409,500
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1523
4500 Gulf Of Mexico Drive #206
Longboat Key, FL 34228
MLS #: A4177537
Subdivision: windward bay condo amd
Wow! Now listed at $8,500 BELOW appraisal! Watch manatees frolic in the marina. Watch ospreys build their nests on the posts. Enjoy bay and marina views as...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$399,000
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1523
4500 Gulf Of Mexico Drive #PH6
Longboat Key, FL 34228
MLS #: A4168620
Subdivision: windward bay condo amd
Tenant occupied until 4/15/17.Rarely available corner penthouse in this desirable bay front community. The view of Sarasota Bay with the skyline of Bradenton...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$395,000
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1523
4960 Gulf Of Mexico Drive #201
Longboat Key, FL 34228
MLS #: A4177049
Subdivision: windward bay condo amd
Enjoy bay and marina views from this first floor (over parking) residence.Updates include new electrical panel in (2016);new HVAC (2/18/2016), laminate...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$389,000
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1325
4500 Gulf Of Mexico Drive #G305
Longboat Key, FL 34228
MLS #: A4162445
Subdivision: windward bay condo amd
BRING YOUR INVESTORS to this move-in ready condo. This beautifully furnished residence is being offered furnished (with some exclusions.) Features include new...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$335,000
Bedrooms: 2
Baths: 2
Approx Sq Ft: 1325
4500 Gulf Of Mexico Drive #PH2
Longboat Key, FL 34228
MLS #: A4167934
Subdivision: windward bay condo amd
Wow! What a view. This 2/2 penthouse residence has been upgraded with travertine floors in some areas and beautiful tile in the kitchen, hallways and baths;...
Contact Annette Smith at (941) 504-3922 to inquire about this property.

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