Windward Bay

Windward Bay is a waterfront community of townhouses in Longboat Key, Florida, with a range of options priced between $410,000 and $1,200,000. There are currently a total of 9 townhouses for sale in Windward Bay. The smallest Windward Bay townhouse presently available is a two bedroom two bathroom residence that is 911 square feet (812SF Under Air living space), and the largest of the Windward Bay townhouses currently on the market has three beds and two baths and is a 2,283 square foot (1,900SF Under Air) residence.

Property management fees in Sarasota County vary depending on the community and sometimes vary between townhouses in the community. The current HOA fees for Windward Bay are $1,526. This fee includes common area maintenance, grounds maintenance, building maintenance, maintaining the community roads, the community pool, and security. Also included is real estate taxes for common areas, property insurance, water, electric, trash removal, sewer, pest control, Cable TV & internet, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Windward Bay townhouse.

Windward Bay amenities include a clubhouse, swimming pool, a state-of-the-art fitness center, sauna, and laundry facilities. Sports facilities include tennis courts, pickleball courts, basketball court, and shuffleboard. There is also a community park, as well as walking or jogging trails.

The Windward Bay HOA rules do allow homeowners to have pets although there are certain breed restrictions. There is a limit of how many pets you may have, and there is a restriction on pet size. Dogs and cats are allowed.

There are two commercial airports that serve Windward Bay - Sarasota Bradenton International (SRQ), which is six miles away, and Tampa International (TPA), which is 40 miles away.

Windward Bay real estate activity on the Longboat Key MLS during the past year (as of November 2025) reflects nine townhouses changing hands, with an average asking price of $600,711 and an average selling price of $565,939. This represents a healthy list-to-sell price ratio of 94% and $407 per square foot. During this period, Windward Bay townhouses for sale have taken an average of 138 days to sell.

In addition, there are numerous other communities in Longboat Key to choose from, or you may browse all available Townhouses for sale in Longboat Key. Townhouses for sale in Windward Bay are selling quickly. Set up a new listing alert, and we will notify you immediately when a new waterfront townhouse in Windward Bay hits the market. You can also always contact your ZFC Real Estate agent, who would happily assist you further with all your Florida real estate needs.

Windward Bay Townhouses For Sale

$1,200,000

MLS#MFRA4650036

4968 Gulf Of Mexico Dr #villa 22
Longboat Key, FL 34228

3

2

1,422 SqFt

Water Front

26.13 Acres

186 Days

Reduced

$775,000

$825,000

MLS#MFRA4664363

4500 Gulf Of Mexico Dr #202
Longboat Key, FL 34228

2

2

1

1,312 Sq Ft

Water Front

26 Acres

65 Days

$775,000

MLS#MFRA4670932

4900 Gulf Of Mexico Dr #203
Longboat Key, FL 34228

2

2

1

1,325 Sq Ft

Water Front

26.67 Acres

9 Days

$735,000

MLS#MFRA4665034

4976 Gulf Of Mexico Dr #villa 18
Longboat Key, FL 34228

3

2

2,283 Sq Ft

Water Front

26 Acres

18 Days

$698,000

MLS#MFRA4671087

4900 Gulf Of Mexico Dr #205
Longboat Key, FL 34228

2

2

1

1,312 Sq Ft

Water Front

7 Days

$695,000

MLS#MFRA4667631

4540 Gulf Of Mexico Dr #204
Longboat Key, FL 34228

2

2

1

1,312 Sq Ft

Water Front

35 Days

$689,000

MLS#MFRA4668880

4500 Gulf Of Mexico Dr #305
Longboat Key, FL 34228

2

2

1,312 Sq Ft

Water Front

21.13 Acres

9 Days

$595,000

MLS#MFRA4671823

4760 Gulf Of Mexico Dr. Villa 7
Longboat Key, FL 34228

2

2

931 SqFt

26.67 Acres

0 Days

Reduced

$499,000

$569,900

MLS#MFRA4652683

4840 Gulf Of Mexico Dr #villa 15
Longboat Key, FL 34228

2

2

1,084 SqFt

26.67 Acres

182 Days

9 Active Listings in Windward Bay