Cypress Woods Kissimmee

Cypress Woods is a gated community of single family homes in Kissimmee, Florida, with a range of options priced between $259,900 and $569,999. There are currently a total of 18 homes for sale in Cypress Woods. The smallest Cypress Woods home presently available is a three bedroom two bathroom residence that is 1,599 square feet (1,179SF Under Air living space), and the largest of the Cypress Woods homes currently on the market has five beds and three baths and is a 3,603 square foot (3,047SF 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 $23 to $1,332. This fee includes grounds maintenance, the community pool, 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 September 2025) reflects twenty five homes changing hands, with an average asking price of $347,920 and an average selling price of $343,544. This represents a healthy list-to-sell price ratio of 99% and $121 per square foot. During this period, Cypress Woods homes for sale have taken an average of 91 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 ZFC Real Estate agent, who would happily assist you further with all your Central Florida real estate needs.

Cypress Woods Homes For Sale

$449,500

MLS#MFRS5132467

4455 Cherry Branch Ct
Kissimmee, FL 34758

4

3

2

3,603 SqFt

0.18 Acres

50 Days

Reduced

$443,000

$455,000

MLS#MFRO6332141

536 Pinehurst Cv
Kissimmee, FL 34758

5

3

2

3,176 SqFt

Pool

0.28 Acres

61 Days

Reduced

$435,000

$440,000

MLS#MFRO6333152

418 Marlberry Leaf Ct
Kissimmee, FL 34758

4

3

2

3,134 SqFt

0.31 Acres

56 Days

$430,000

MLS#MFRO6334634

4573 Ficus Tree Rd
Kissimmee, FL 34758

4

3

2

3,603 SqFt

0.21 Acres

52 Days

$394,900

MLS#MFRO6334184

4491 Maple Chase Trl
Kissimmee, FL 34758

4

3

2

3,603 SqFt

0.23 Acres

49 Days

Reduced

$370,000

$385,000

MLS#1051446

462 Peppermill Cir
Kissimmee, FL 34758

4

3

2

2,318 SqFt

0.25 Acres

81 Days

Reduced

$370,000

$385,000

MLS#MFRO6326246

462 Peppermill Cir
Kissimmee, FL 34758

4

3

2

3,049 SqFt

0.25 Acres

81 Days

$370,000

MLS#MFRS5131288

468 Acacia Tree Way
Kissimmee, FL 34758

4

3

2

3,049 SqFt

0.19 Acres

71 Days

Reduced

$360,000

$390,000

MLS#MFRS5121935

466 Peppermill Cir
Kissimmee, FL 34758

4

3

2

3,049 SqFt

Pool

0.29 Acres

210 Days

Under Contract

$350,000

MLS#MFRO6331233

453 Peppermill Cir
Kissimmee, FL 34758

4

3

2

3,049 SqFt

Pool

0.26 Acres

47 Days

Reduced

$340,000

$350,000

MLS#MFRS5131318

580 Oak Branch Cir
Kissimmee, FL 34758

4

2

2

2,505 SqFt

0.19 Acres

69 Days

$315,999

MLS#MFRO6326770

603 Pinehurst Ct
Kissimmee, FL 34758

3

2

2

2,738 SqFt

0.18 Acres

69 Days

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18 Active Listings in Cypress Woods