Cypresswood Homes For Sale

Welcome to Cypresswood located in Winter Haven FL.  The community has a homeowner's association. The amenities include a community swimming pool, golf course, tennis courts, clubhouse, full time security guard and restaurant. The homes for sale in Cypresswood are updated every day from the local MLS. If you would like to schedule a showing or have any questions about any of these homes for sale, please call David Shippey at 863-521-4517 or just click the "More Info" button on any property detail page.

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Displaying results 11-18 of 18
61 Photos 47 Enclave Drive Winter Haven, FL 33884

47 Enclave Drive
Winter Haven, FL 33884
Cypresswood Enclave Ph 2
Residential

MLS# P4937867 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1444 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Enclave Ph 2

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

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$245,000
Reduced -$15,000
Provided courtesy of XCELLENCE REALTY, INC
35 Photos 649 Broadmoor Circle Winter Haven, FL 33884

649 Broadmoor Circle
Winter Haven, FL 33884
Cypresswood Golf Villas
Residential

MLS# O6352259 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1278 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Golf Villas

UNDER MARKET VALUE!!! Brand NEW AC Fan motor, AC Amp Fuse and AC capacitor installed May 2026. Brand NEW fire/carbon monoxide detector alarms throu... 

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$149,700
Reduced -$1,800
Provided courtesy of SUCCESS INVESTMENT REALTY
39 Photos 2817 Wingfoot Court Winter Haven, FL 33884

2817 Wingfoot Court
Winter Haven, FL 33884
Cypresswood Golf Villas Gc-2
Residential

MLS# P4935798 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1666 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Golf Villas Gc-2

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

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$270,000
Provided courtesy of NEXTHOME NORRIS & COMPANY REALTY
61 Photos 419 Greenfield Road Winter Haven, FL 33884

419 Greenfield Road
Winter Haven, FL 33884
Cypresswood Mdws
Residential

MLS# TB8513442 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1924 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Mdws

Cypresswood Golf & Country Club welcomes you to 419 Greenfield Drive. This desirable gated golf community has a host of activities and treasures, b... 

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$349,990
Provided courtesy of BOARDWALK REALTY ASSOCIATES, LLC
42 Photos 2964 Plantation Road Winter Haven, FL 33884

2964 Plantation Road
Winter Haven, FL 33884
Cypresswood Plantations
Residential

MLS# O6352519 / Active
4 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 3614 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Plantations

Welcome to this refined sanctuary where timeless elegance meets Floridas tranquil landscape. On a premium golf-adjacent lot within the guarded, gat... 

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$579,900
Reduced -$20,000
Provided courtesy of PREMIER SOTHEBYS INT'L REALTY
22 Photos 665 Broadmoor Circle Winter Haven, FL 33884

665 Broadmoor Circle
Winter Haven, FL 33884
Cypresswood Tennis Villas
Residential

MLS# TB8496998 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1139 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Tennis Villas

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

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$170,000
Reduced -$10,000
Provided courtesy of COMPASS FLORIDA LLC
27 Photos 306 Eagle Pond Drive Winter Haven, FL 33884

306 Eagle Pond Drive
Winter Haven, FL 33884
Eagle Pond Condo
Residential

MLS# TB8509154 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1017 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Eagle Pond Condo

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

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$211,000
Provided courtesy of COLDWELL BANKER REALTY
36 Photos 704 Eagle Pond Drive UNIT #704 Winter Haven, FL 33884

704 Eagle Pond Drive UNIT #704
Winter Haven, FL 33884
Eagle Pond Condo
Residential

MLS# P4938866 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1017 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Eagle Pond Condo

Don't miss this rare opportunity to own this lovely GROUND FLOOR Eagle Pond condominium in the highly sought-after gated community of Cypresswood G... 

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$179,900
Provided courtesy of JOHN WOOD REALTY, INC.

Broker Reciprocity The information being provided by © 2026 My Florida Regional MLS DBA Stellar MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the My Florida Regional MLS DBA Stellar MLS. XCELLENCE is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of XCELLENCE, a broker participant of My Florida Regional MLS DBA Stellar MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. MLS IDX data last updated on 06-06-2026 2:00 AM EST.

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