Cypress Woods Kissimmee

Cypress Woods is a gated community of single family homes in Kissimmee, Florida, with a range of options priced between $302,999 and $569,999. There are currently a total of 10 homes for sale in Cypress Woods. The smallest Cypress Woods home presently available is a three bedroom two bathroom residence that is 1,731 square feet (1,459SF Under Air living space), and the largest of the Cypress Woods homes currently on the market has four beds and three baths and is a 3,603 square foot (2,847SF Under Air) residence.

Property management fees in Osceola County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Cypress Woods range from $90 to $400. This fee includes grounds maintenance, the community pool, trash removal, Cable TV & internet, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Cypress Woods home.

Cypress Woods amenities include a clubhouse, swimming pool, and a state-of-the-art fitness center. Sports facilities include tennis courts, pickleball courts, racquetball, and basketball court. There is also a community park, a playground, as well as walking or jogging trails.

The Cypress Woods 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. Dogs and cats are allowed.

There are four commercial airports that serve Cypress Woods - Kissimmee Gateway (ISM), which is ten miles away; Orlando International (MCO), which is twenty two miles away; Orlando Executive (ORL), which is twenty eight miles away, and Lakeland Linder International (LAL), which is 35 miles away from Cypress Woods.

Cypress Woods real estate activity on the Kissimmee MLS during the past year (as of June 2026) reflects twenty seven homes changing hands, with an average asking price of $362,214 and an average selling price of $352,181. This represents a healthy list-to-sell price ratio of 97% and $117 per square foot. During this period, Cypress Woods homes for sale have taken an average of 84 days to sell.

In addition, there are numerous other communities in Kissimmee to choose from, or you may browse all available Kissimmee Real Estate, including some new construction opportunities. Homes for sale in Cypress Woods are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Cypress Woods 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.

Cypress Woods Homes For Sale

Reduced

$415,990

$425,000

MLS#MFRS5149608

4556 Ficus Tree Rd
Kissimmee, FL 34758

4

3

2

3,603 SqFt

0.22 Acres

45 Days

Reduced

$405,000

$435,000

MLS#MFRO6386701

4417 Canopy Ct
Kissimmee, FL 34758

4

3

2

3,603 SqFt

0.19 Acres

113 Days

$390,000

MLS#MFRS5148605

442 Tamarind Parke Ln
Kissimmee, FL 34758

4

3

2

3,049 SqFt

Pool

0.2 Acres

60 Days

$380,000

MLS#MFRS5145640

418 Marlberry Leaf Ct
Kissimmee, FL 34758

4

3

2

3,134 SqFt

0.31 Acres

104 Days

Reduced

$359,900

$364,990

MLS#MFRO6388748

468 Acacia Tree Way
Kissimmee, FL 34758

4

3

2

2,308 SqFt

0.19 Acres

108 Days

Under Contract

$345,000

$355,000

MLS#MFRO6356521

206 Redwood Bark Trl
Kissimmee, FL 34758

4

3

2

2,824 SqFt

Water Front

0.34 Acres

231 Days

$340,000

MLS#MFRS5151383

577 Pinehurst Cv
Kissimmee, FL 34758

3

3

2

2,622 SqFt

0.24 Acres

18 Days

$314,900

MLS#MFRTB8519530

4526 Ficus Tree Rd
Kissimmee, FL 34758

3

3

2

3,049 SqFt

0.27 Acres

1 Days

Reduced

$301,999

$334,500

MLS#MFRS5137421

540 Oak Branch Cir
Kissimmee, FL 34758

3

2

2

1,899 SqFt

0.19 Acres

232 Days

$299,000

MLS#MFRO6417948

102 Saffron Way
Kissimmee, FL 34758

3

2

2

2,190 SqFt

0.17 Acres

4 Days

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10 Active Listings in Cypress Woods