How many active listings are available in this area?

There are 14 active listings in this area.

What is the average listing price in this area?

The average listing price for the displayed results is $230,550.

How many active listings are available in this area?

There are 14 active listings in this area.

What is the average listing price in this area?

The average listing price for the displayed results is $230,550.

Home Florida Polk Cypresswood Golf and Country Club

Cypresswood Golf and Country Club

Looking for golf homes on Cypresswood Golf and Country Club? Discover golf properties located in or near golf course communities in Polk, Florida. From luxury estates overlooking the greens to comfortable homes within golf communities, there are options to fit a variety of lifestyles and budgets.

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Showing 1-14 of 14 Homes For Sale

For Sale

Welcome to 2817 Wingfoot Ct, located in the desirable - photo 1

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Welcome to 2817 Wingfoot Ct, located in the desirable - photo 38

$270,000

3 Beds | 2.0 Baths | 1,666 Sqft

2817 Wingfoot Ct, Winter Haven, FL 33884

Welcome to 2817 Wingfoot Ct, located in the desirable Cypresswood Golf Villas. This beautifully maintained villa sits along the 8th fairway of the prestigious Cypresswood...

Ad#: 6501812 • Added: 09/08/2025 • Updated: 05/26/2026

For Sale

New to the market is this *one owner* villa located in the - photo 1

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$259,900

3 Beds | 2.0 Baths | 1,526 Sqft

29 ENCLAVE DR, Winter Haven, FL 33884

New to the market is this *one owner* villa located in the sought-after Enclave neighborhood located in Cypresswood Golf and Country Club in SE Winter Haven. This...

Ad#: 7352695 • Added: 03/04/2026 • Updated: 06/27/2026

For Sale

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$245,000

2 Beds | 2.0 Baths | 1,444 Sqft

47 ENCLAVE DR, Winter Haven, FL 33884

PRICE REDUCED $15,000! Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course...

Ad#: 7321660 • Added: 02/25/2026 • Updated: 06/26/2026

For Sale

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$229,900

2 Beds | 2.0 Baths | 1,368 Sqft

14 ENCLAVE DR, Winter Haven, FL 33884

Fresh on the market is this meticulously maintained and professionally updated 2 bedroom 2 bath villa located in the sought after *Enclave* neighborhood in Cypresswood, a...

Ad#: 6489069 • Added: 08/05/2025 • Updated: 06/27/2026

For Sale

WELCOME TO THIS CHARMING TOWNHOUSE located in the sought-after - photo 1

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WELCOME TO THIS CHARMING TOWNHOUSE located in the sought-after - photo 33

$224,000

2 Beds | 2.0 Baths | 1,368 Sqft

10 ENCLAVE DR, Winter Haven, FL 33884

WELCOME TO THIS CHARMING TOWNHOUSE located in the sought-after Cypresswood Golf & Country Club community in beautiful Winter Haven! This inviting 2 BD / 2 BA home offers...

Ad#: 7724099 • Added: 05/14/2026 • Updated: 06/26/2026

For Sale

Beautiful completely updated condo in the highly desirable gated - photo 1

Beautiful completely updated condo in the highly desirable gated - photo 2

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Beautiful completely updated condo in the highly desirable gated - photo 22

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Beautiful completely updated condo in the highly desirable gated - photo 24

Beautiful completely updated condo in the highly desirable gated - photo 25

Beautiful completely updated condo in the highly desirable gated - photo 26

Beautiful completely updated condo in the highly desirable gated - photo 27

$211,000

2 Beds | 2.0 Baths | 1,017 Sqft

306 EAGLE POND DR, Winter Haven, FL 33884

Beautiful completely updated condo in the highly desirable gated community of Cypresswood Golf and Country Club. It features tile flooring throughout the whole condo...

Ad#: 7805423 • Added: 05/31/2026 • Updated: 06/10/2026

For Sale

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$190,000

2 Beds | 2.0 Baths | 1,422 Sqft

1052 MEDINAH DR, Winter Haven, FL 33884

Welcome to the affordable lifestyle of living in a Villa within a golf course community. Upon entering the front of the home you will notice a courtyard area on the left...

Ad#: 7567288 • Added: 04/14/2026 • Updated: 06/27/2026

For Sale

FLORIDA LIVING AT IT'S BEST!!! Don't miss out on this end unit - photo 1

FLORIDA LIVING AT IT'S BEST!!! Don't miss out on this end unit - photo 2

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$189,900

2 Beds | 2.0 Baths | 1,278 Sqft

645 BROADMOOR CIR 645, Winter Haven, FL 33884

FLORIDA LIVING AT IT'S BEST!!! Don't miss out on this end unit, spacious 2 bedroom 2 bath townhome in a gated community. This unit is conveniently located right across...

Ad#: 7910422 • Added: 06/19/2026 • Updated: 06/26/2026

For Sale

Enjoy the Florida Country Club Lifestyle in this affordable and - photo 1

Enjoy the Florida Country Club Lifestyle in this affordable and - photo 2

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$185,000

2 Beds | 2.0 Baths | 1,398 Sqft

1026 MEDINAH DR, Winter Haven, FL 33884

Enjoy the Florida Country Club Lifestyle in this affordable and updated 2 bedroom 2 bath villa. Recent updates include new luxury vinyl flooring, new dishwasher and new...

Ad#: 7906145 • Added: 06/18/2026 • Updated: 06/27/2026

For Sale

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$170,000

2 Beds | 2.0 Baths | 1,139 Sqft

665 BROADMOOR CIR, Winter Haven, FL 33884

Discover how easy life can feel in this beautifully maintained 2-bedroom, 2-bath villa offering over 1,100 square feet of comfortable, thoughtfully designed living space...

Ad#: 7915087 • Added: 06/09/2026 • Updated: 06/23/2026

Sale Pending

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$330,000

3 Beds | 2.0 Baths | 1,964 Sqft

318 GREENFIELD RD, Winter Haven, FL 33884

Nestled on a beautifully landscaped and tree shaded lot this well maintained 3 bedroom 2 bathroom home features split bedrooms with ample closets, formal living and...

Ad#: 7724029 • Added: 05/14/2026 • Updated: 06/27/2026

Sale Pending

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$289,000

2 Beds | 2.0 Baths | 1,621 Sqft

428 GLENEAGLES CT, Winter Haven, FL 33884

Under contract-accepting backup offers. Now is your chance! Come and be a part of this active, Golf Course community and live in this beautifully maintained, updated...

Ad#: 7402086 • Added: 03/13/2026 • Updated: 06/27/2026

Sale Pending

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$249,000

2 Beds | 2.0 Baths | 1,660 Sqft

460 PINEHURST CT, Winter Haven, FL 33884

Relaxed golf community living inside the gated and guarded Cypresswood Golf & Country Club. Welcome to 460 Pinehurst Ct in Winter Haven, Florida -- an updated and...

Ad#: 7790906 • Added: 05/28/2026 • Updated: 06/27/2026

Sale Pending

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$185,000

2 Beds | 2.0 Baths | 1,439 Sqft

2270 FIRESTONE PLACE, Winter Haven, FL 33884

Under contract-accepting backup offers. Welcome to this spacious and well-maintained villa in Cypresswood Golf & Country Club, offering comfortable living in one of...

Ad#: 6858128 • Added: 11/20/2025 • Updated: 06/26/2026

Cypresswood Golf and Country Club Real Estate Agent Info

About Cypresswood Golf and Country Club

Course Location:

1099 Clubhouse Rd

Winter Haven, FL 33884-1200

Polk County

Toll Free Phone: -

Phone: (863) 324-6174

Fax: (863) 325-8802

Facility Information

Facility Type:

Daily Fee Facility

Facility Category:

Real Estate Development

# of Regulation Holes:

# of Executive Holes:

Year Open:

1974

Month Open:

January

# of Tee Stations:

Course Information

Course Name:

Cypresswood

Course Designer:

Ron Garl

Course Type:

Daily Fee Course

Course Category:

Real Estate Development

# of Holes:

Slope:

126

Rating:

# of Yards:

6912

Par:

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Cypresswood Golf and Country Club Real Estate Agent Info

About Cypresswood Golf and Country Club

Facility Information

Course Information