Crestwynd Bay

Crestwynd Bay is a community of townhouses in Kissimmee, Florida, with a range of options priced between $240,000 and $272,500. There are currently a total of 7 townhouses for sale in Crestwynd Bay. The smallest Crestwynd Bay townhouse presently available is a three bedroom two bathroom residence that is 1,227 square feet (1,187SF Under Air living space), and the largest of the Crestwynd Bay townhouses currently on the market has three beds and three baths and is a 1,503 square foot (1,362SF Under Air) residence.

Property management fees in Osceola County vary depending on the community and sometimes vary between townhouses in the community. The current HOA fees for townhomes in Crestwynd Bay range from $326 to $1,000. 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, trash removal, sewer, pest control, Cable TV & internet, parking, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Crestwynd Bay townhouse.

Crestwynd Bay amenities include a clubhouse, swimming pool, and a state-of-the-art fitness center. Sports facilities include tennis courts. There is also a community park, as well as a playground.

The Crestwynd 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 four commercial airports that serve Crestwynd Bay - Kissimmee Gateway (ISM), which is ten miles away; Orlando International (MCO), which is nineteen miles away; Orlando Executive (ORL), which is twenty two miles away, and Lakeland Linder International (LAL), which is 35 miles away from Crestwynd Bay.

Crestwynd Bay real estate activity on the Kissimmee MLS during the past year (as of June 2026) reflects four townhouses changing hands, with an average asking price of $273,925 and an average selling price of $266,225. This represents a healthy list-to-sell price ratio of 97% and $205 per square foot. During this period, Crestwynd Bay townhouses for sale have taken an average of 134 days to sell.

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

Crestwynd Bay Townhouses For Sale

$272,500

MLS#MFRS5144966

2680 Mayaguana St
Kissimmee, FL 34747

3

3

1,402 SqFt

0.02 Acres

111 Days

$269,000

MLS#MFRO6404355

2658 Mayaguana St
Kissimmee, FL 34747

3

3

1,503 SqFt

0.02 Acres

51 Days

Under Contract

$259,000

$290,000

MLS#MFRS5131372

2619 Andros Ln
Kissimmee, FL 34747

3

3

1,392 SqFt

0.03 Acres

333 Days

Reduced

$249,990

$299,900

MLS#MFRO6308205

2662 Mayaguana St
Kissimmee, FL 34747

3

3

1,227 SqFt

0.03 Acres

407 Days

Reduced

$249,990

$299,900

MLS#AX-11804727

2662 Mayaguana Street
Kissimmee, FL 34747

3

3

1,227 SqFt

412 Days

Under Contract

$240,000

$289,000

MLS#MFRS5137340

2626 Andros Ln
Kissimmee, FL 34747

3

3

1,392 SqFt

0.02 Acres

241 Days

Reduced

$235,000

$249,900

MLS#MFRS5148531

2666 Andros Ln
Kissimmee, FL 34747

3

3

1,227 SqFt

0.03 Acres

60 Days

7 Active Listings in Crestwynd Bay