Cypress Woods Kissimmee

Cypress Woods is a gated community of single family homes in Kissimmee, Florida, with a range of options priced between $279,000 and $569,999. There are currently a total of 12 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 (2,930SF 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 $257. 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 January 2026) reflects twenty six homes changing hands, with an average asking price of $355,008 and an average selling price of $349,062. This represents a healthy list-to-sell price ratio of 98% and $125 per square foot. During this period, Cypress Woods homes for sale have taken an average of 87 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

$465,000

MLS#MFRS5136813

565 Pinehurst
Kissimmee, FL 34758

4

3

2

3,603 SqFt

Pool

0.2 Acres

67 Days

Reduced

$460,000

$480,000

MLS#MFRS5136420

4574 Ficus Tree Rd N
Kissimmee, FL 34758

4

3

2

3,603 SqFt

Pool

0.2 Acres

83 Days

$443,999

MLS#MFRS5132467

4455 Cherry Branch Ct
Kissimmee, FL 34758

4

3

2

3,603 SqFt

0.18 Acres

144 Days

Reduced

$410,000

$440,000

MLS#MFRO6333152

418 Marlberry Leaf Ct
Kissimmee, FL 34758

4

3

2

3,134 SqFt

0.31 Acres

150 Days

Reduced

$350,000

$385,000

MLS#1051446

462 Peppermill Cir
Kissimmee, FL 34758

4

3

2

2,318 SqFt

0.25 Acres

175 Days

Reduced

$350,000

$385,000

MLS#MFRO6326246

462 Peppermill Cir
Kissimmee, FL 34758

4

3

2

3,049 SqFt

0.25 Acres

175 Days

Under Contract

$349,999

$365,000

MLS#MFRS5135423

501 Oak Branch Ct
Kissimmee, FL 34758

3

2

2

2,727 SqFt

Pool

0.31 Acres

98 Days

Under Contract

$349,990

$390,000

MLS#MFRS5121935

466 Peppermill Cir
Kissimmee, FL 34758

4

3

2

3,049 SqFt

Pool

0.29 Acres

304 Days

Reduced

$319,999

$334,500

MLS#MFRS5137421

540 Oak Branch Cir
Kissimmee, FL 34758

3

2

2

1,899 SqFt

0.19 Acres

60 Days

Under Contract

$299,000

MLS#MFRO6364507

207 Redwood Bark Trl
Kissimmee, FL 34758

4

3

2

3,463 SqFt

0.26 Acres

31 Days

$294,900

MLS#MFRS5139192

447 Acacia Tree Way
Kissimmee, FL 34758

4

3

2

3,463 SqFt

0.26 Acres

38 Days

Reduced

$279,000

$289,900

MLS#MFRO6331484

409 Spice Ct
Kissimmee, FL 34758

3

2

2

1,895 SqFt

0.16 Acres

155 Days

You may also be interested in Cypress Woods in Lake Worth, Cypress Woods in Naples, Cypress Woods in Orlando, Cypress Woods in Cocoa or Cypress Woods in Fort Myers.

12 Active Listings in Cypress Woods