Cypresswood Golf And Country Club

Cypresswood Golf And Country Club is a country club community of single family homes, condos, and townhomes in Winter Haven, Florida, with a range of options priced between $149,900 and $599,900. There are currently a total of 26 homes for sale in Cypresswood Golf And Country Club. The smallest Cypresswood Golf And Country Club home presently available is a two bedroom two bathroom residence that is 1,037 square feet (1,017SF Under Air living space), and the largest of the Cypresswood Golf And Country Club homes currently on the market has four beds and three baths and is a 5,456 square foot (3,614SF Under Air) residence.

Property management fees in Polk County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Cypresswood Golf And Country Club range from $200 to $1,825 and range from $335 to $375 for a Cypresswood Golf And Country Club condo and $280 to $433 for a townhome. This fee includes common area maintenance, grounds maintenance, building maintenance, maintaining the community roads, the community pool, and security. Also included is a 24-hour guard, real estate taxes for common areas, property insurance, water, trash removal, sewer, pest control, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Cypresswood Golf And Country Club home. Golf communities typically entail membership fees (sometimes mandatory) that are in addition to the HOA fees, so please check with your Realtor® or the club membership office.

Cypresswood Golf And Country Club amenities include a clubhouse, swimming pool, spa / hot tub, and a state-of-the-art fitness center. Sports facilities include a championship golf course, tennis courts, pickleball courts, racquetball, and basketball court. Onsite dining venues consist of a restaurant, and a bar / lounge. There is also a community park, as well as a playground.

The Cypresswood Golf And Country Club 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 Cypresswood Golf And Country Club - Lakeland Linder International (LAL), which is twenty three miles away; Kissimmee Gateway (ISM), which is twenty three miles away; Orlando International (MCO), which is 36 miles away, and Orlando Executive (ORL), which is 42 miles away from Cypresswood Golf And Country Club.

Cypresswood Golf And Country Club real estate activity on the Winter Haven MLS during the past year (as of May 2026) reflects 63 homes changing hands, with an average asking price of $300,005 and an average selling price of $288,814. This represents a healthy list-to-sell price ratio of 96% and $120 per square foot. During this period, Cypresswood Golf And Country Club homes for sale have taken an average of 98 days to sell.

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

Cypresswood Golf And Country Club Homes For Sale

$598,900

MLS#MFRL4959891

2935 Plantation Rd
Winter Haven, FL 33884

4

4

2

2,724 SqFt

Pool

0.35 Acres

48 Days

Reduced

$579,900

$650,000

MLS#MFRO6352519

2964 Plantation Rd
Winter Haven, FL 33884

4

4

3

5,456 SqFt

Pool

0.46 Acres

208 Days

Reduced

$442,000

$465,000

MLS#MFRP4938120

2968 Plantation Rd
Winter Haven, FL 33884

3

2

3

4,138 SqFt

0.42 Acres

53 Days

Reduced

$359,950

$379,950

MLS#MFRL4959462

241 Greenfield Rd
Winter Haven, FL 33884

2

2

2

3,342 SqFt

0.37 Acres

83 Days

Reduced

$340,000

$349,000

MLS#MFRO6404080

3322 Oak Hill Pl
Winter Haven, FL 33884

3

2

2

2,699 SqFt

0.15 Acres

11 Days

$337,000

MLS#MFRP4937966

688 Augusta Rd
Winter Haven, FL 33884

3

2

2

2,302 SqFt

Pool

0.14 Acres

76 Days

Under Contract

$325,000

$335,000

MLS#MFRL4957294

731 Canberra Rd
Winter Haven, FL 33884

3

2

2

2,683 SqFt

0.14 Acres

172 Days

$300,000

MLS#MFRS5148089

69 Enclave Dr
Winter Haven, FL 33884

3

2

2

2,149 SqFt

0.05 Acres

14 Days

$299,999

MLS#MFRP4937209

469 Muirfield Ct
Winter Haven, FL 33884

2

2

2

1,931 SqFt

0.14 Acres

155 Days

$289,000

MLS#MFRL4960230

428 Gleneagles Ct
Winter Haven, FL 33884

2

2

2

2,557 SqFt

0.13 Acres

60 Days

Reduced

$270,000

$280,000

MLS#MFRP4935798

2817 Wingfoot Ct
Winter Haven, FL 33884

3

2

1,682 SqFt

0.05 Acres

277 Days

Reduced

$259,900

$269,900

MLS#MFRL4959890

29 Enclave Dr
Winter Haven, FL 33884

3

2

2

2,149 SqFt

0.05 Acres

69 Days

26 Active Listings in Cypresswood Golf And Country Club