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.

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.  Read More...

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.
Windward Bay January 20, 2019
11
Listed
43
Avg. DOM
$339.73
Avg. $ / Sq.Ft.
$419,900
Med. List Price
11 Properties Found.
Sort By:
4800 Gulf Of Mexico Drive #205
Longboat Key, FL 34228
4800 Gulf Of Mexico Drive #205 Longboat Key, FL 34228
1 of 34
$560,000
Subdivision: Windward Bay Condo Amd
BEDS
2
BATHS
2
SQ.FT.
1,325
BUILT
1975
ON SITE
53Days
MLS
A4420391
It doesn't get much better than this-----superb renovation, unique kitchen redesign, serene location! Step into this Bayfront residence and experience sweeping bay views, blue sky and lush...
4900 Gulf Of Mexico Drive #PH5
Longboat Key, FL 34228
Open House
4900 Gulf Of Mexico Drive #PH5 Longboat Key, FL 34228
1 of 39
$538,000 ( $7,000 )
Subdivision: Windward Bay Condo Amd
BEDS
2
BATHS
2
SQ.FT.
1,335
BUILT
1975
ON SITE
39Days
MLS
A4421009
Spectacular! You will love the gorgeous, unobstructed views of Sarasota Bay from this beautifully decorated/updated, Turn-Key Furnished, 2 Bed/2 Bath Penthouse. Entering your new home, your first...
4700 Gulf Of Mexico Drive #PH3
Longboat Key, FL 34228
4700 Gulf Of Mexico Drive #PH3 Longboat Key, FL 34228
1 of 38
$525,000
Subdivision: Windward Bay Condo Amd
BEDS
2
BATHS
2
SQ.FT.
1,325
BUILT
1975
ON SITE
28Days
MLS
A4422211
Imagine looking at unobstructed full bay views from downtown Sarasota waterfront to the south, continuing along the bay to northwest Bradenton, nearly 20 miles of shoreline. Sunrises from every room!...
4500 Gulf Of Mexico Drive #PH6
Longboat Key, FL 34228
4500 Gulf Of Mexico Drive #PH6 Longboat Key, FL 34228
1 of 30
$515,000
Subdivision: Windward Bay Condo Amd
BEDS
2
BATHS
2
SQ.FT.
1,523
BUILT
1975
ON SITE
70Days
MLS
A4418795
TREEHOUSE.. PENTHOUSE...BOATHOUSE! Fabulous opportunity for a fully remodeled, 2bed/2bath top floor condo, end location, that appears as if it sits atop lush trees yet is situated overlooking the...
4500 Gulf Of Mexico Drive #201
Longboat Key, FL 34228
4500 Gulf Of Mexico Drive #201 Longboat Key, FL 34228
1 of 38
$420,000 ( $15,000 )
Subdivision: Windward Bay Condo Amd
BEDS
2
BATHS
2
SQ.FT.
1,561
BUILT
1975
ON SITE
55Days
MLS
A4420037
This lovely updated residence with choice large corner location featuring Bay views can be your home in paradise. From every room you are drawn to the Bay where manatees, dolphin and pelicans bring...
4700 Gulf Of Mexico Drive #303
Longboat Key, FL 34228
4700 Gulf Of Mexico Drive #303 Longboat Key, FL 34228
1 of 25
$419,900
Subdivision: Windward Bay Condo Amd
BEDS
2
BATHS
2
SQ.FT.
1,312
BUILT
1975
ON SITE
110Days
MLS
A4415060
Here is the perfect peaceful place to call home. This delightfully updated condominium features a wall of windows ideal for viewing the lovely canvas upon which sunrises and sunsets reveal their...
4540 Gulf Of Mexico Drive #201
Longboat Key, FL 34228
4540 Gulf Of Mexico Drive #201 Longboat Key, FL 34228
1 of 37
$415,000
Subdivision: Windward Bay Condo Amd
BEDS
2
BATHS
2
SQ.FT.
1,337
BUILT
1975
ON SITE
31Days
MLS
A4422082
Stunning waterfront residence has undergone a gorgeous renovation, with views of the inter coastal and mangrove estuary. Highlighted updates include porcelain tile floors, a bright open kitchen which...
4700 Gulf Of Mexico Drive #305
Longboat Key, FL 34228
4700 Gulf Of Mexico Drive #305 Longboat Key, FL 34228
1 of 49
$415,000
Subdivision: Windward Bay Condo
BEDS
2
BATHS
2
SQ.FT.
1,312
BUILT
1975
ON SITE
18Days
MLS
A4422164
Gorgeous Sarasota Bay views are yours to be had from every room in this well-priced 2 bed/2 bath, Turn-Key Furnished beauty! With 25+ feet of waterfront windows and a great location, the expansive...
4540 Gulf Of Mexico Drive #206
Longboat Key, FL 34228
Open House
4540 Gulf Of Mexico Drive #206 Longboat Key, FL 34228
1 of 40
$410,000
Subdivision: Windward Bay Condo Amd
BEDS
2
BATHS
2
SQ.FT.
1,152
BUILT
1975
ON SITE
4Days
MLS
O5756822
Wow!!! Your search has ended with this Amazing 2BD/2BA front end unit at WINDWARD BAY, being offered turnkey furnished for your convenience or income investment purposes. Take in the beautiful serene...
4600 Gulf Of Mexico Drive #202
Longboat Key, FL 34228
4600 Gulf Of Mexico Drive #202 Longboat Key, FL 34228
1 of 36
$409,000
Subdivision: Windward Bay Condo Amd
BEDS
2
BATHS
2
SQ.FT.
1,312
BUILT
1975
ON SITE
68Days
MLS
A4419076
LARGE PET FRIENDLY FOR OWNERS AND TENANTS! MOVE-IN READY PROPERTY! YOU STILL HAVE TIME TO SECURE A SEASONAL TENANT TO START EARNING INCOME AND COVERING COSTS! By doing this, it is like you have a...
4500 Gulf Of Mexico Drive #305
Longboat Key, FL 34228
4500 Gulf Of Mexico Drive #305 Longboat Key, FL 34228
1 of 41
$389,000
Subdivision: Windward Bay Condo Amd
BEDS
2
BATHS
2
SQ.FT.
1,325
BUILT
1975
ON SITE
10Days
MLS
A4423792
Enjoy serene views of Sarasota Bay from every room in this well maintained residence. The placid water in the adjacent marina attracts dolphins and manatees as well as egrets, blue herons, night...

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