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Cypresswood Homes for Sale in Winter Haven - 26 homes

Cypresswood homes for sale are located in Polk County, Florida. Find Cypresswood Homes in Winter Haven for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your search for Cypresswood, Winter Haven homes.

Location: Cypresswood, Winter Haven

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  • 2813 WINGFOOT CT, WINTER HAVEN, FL 33884

    $215,00044 Days on yellowkey   MLS ID: L4959887

    REDUCED by $15,000 (6.5%) on 04/15/2026

    For Sale L4959887 - 2813 WINGFOOT CT, WINTER HAVEN, FL 33884 54 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1682
       Built: 1990
    Monthly Fee: $295
       Tax: $2,981 (2025)
    Community: Cypresswood Golf Villas
    Spa: No

    Villa


    Estimated Monthly Payment: $1,721 (change assumption)
    Mortgage ($1,178) + Fees ($295) + Taxes in 2025 ($248)


    Taxes:$2,981

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 665 BROADMOOR CIR, WINTER HAVEN, FL 33884

    $180,000Listed 04/16/2026 11:24AM   MLS ID: TB8496998

    For Sale TB8496998 - 665 BROADMOOR CIR, WINTER HAVEN, FL 33884 22 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1139
       Built: 1981
    Monthly Fee: $335
       Tax: $1,395 (2025)
    Community: Cypresswood Tennis Villas
    Villa


    Estimated Monthly Payment: $1,438 (change assumption)
    Mortgage ($986) + Fees ($335) + Taxes in 2025 ($116)


    Taxes:$1,395

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2964 PLANTATION RD, WINTER HAVEN, FL 33884

    $599,900182 Days on yellowkey   MLS ID: O6352519

    For Sale O6352519 - 2964 PLANTATION RD, WINTER HAVEN, FL 33884 42 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3614
       Built: 1989
    Monthly Fee: $137
       Tax: $618 (2024)
    Community: Cypresswood Plantations
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,476 (change assumption)
    Mortgage ($3,287) + Fees ($137) + Taxes in 2024 ($52)


    Taxes:$618

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1052 MEDINAH DR, WINTER HAVEN, FL 33884

    $210,0001 Day on yellowkey   MLS ID: L4961077

    For Sale L4961077 - 1052 MEDINAH DR, WINTER HAVEN, FL 33884 47 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1422
       Built: 1980
    Monthly Fee: $334
       Tax: $2,847 (2025)
    Community: Cypresswood
    Villa


    Estimated Monthly Payment: $1,722 (change assumption)
    Mortgage ($1,151) + Fees ($334) + Taxes in 2025 ($237)


    Taxes:$2,847

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 35 ENCLAVE DR, WINTER HAVEN, FL 33884

    $242,500559 Days on yellowkey   MLS ID: P4932313

    For Sale P4932313 - 35 ENCLAVE DR, WINTER HAVEN, FL 33884 26 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2070
       Built: 1997
    Monthly Fee: $429
       Tax: $1,632 (2023)
    Community: Cypresswood Enclave Ph 02
    Villa


    Estimated Monthly Payment: $1,894 (change assumption)
    Mortgage ($1,329) + Fees ($429) + Taxes in 2023 ($136)


    Taxes:$1,632

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 731 CANBERRA RD, WINTER HAVEN, FL 33884

    $335,000146 Days on yellowkey   MLS ID: L4957294

    For Sale L4957294 - 731 CANBERRA RD, WINTER HAVEN, FL 33884 51 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2140
       Built: 1989
    Monthly Fee: $17
       Tax: $2,207 (2024)
    Community: Cypresswood Patio Homes
    Single Family


    Estimated Monthly Payment: $2,036 (change assumption)
    Mortgage ($1,836) + Fees ($17) + Taxes in 2024 ($184)


    Taxes:$2,207

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 47 ENCLAVE DR, WINTER HAVEN, FL 33884

    $260,00050 Days on yellowkey   MLS ID: P4937867

    For Sale P4937867 - 47 ENCLAVE DR, WINTER HAVEN, FL 33884 61 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1444
       Built: 1999
    Monthly Fee: $433
       Tax: $3,221 (2025)
    Community: Cypresswood Enclave Ph 2
    Spa: No

    Villa


    Estimated Monthly Payment: $2,126 (change assumption)
    Mortgage ($1,425) + Fees ($433) + Taxes in 2025 ($268)


    Taxes:$3,221

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 2274 FIRESTONE PL, WINTER HAVEN, FL 33884

    $182,500102 Days on yellowkey   MLS ID: L4957980

    0 Days Off yellowkey (back on 4/7/2026)

    For Sale L4957980 - 2274 FIRESTONE PL, WINTER HAVEN, FL 33884 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1410
       Built: 1984
    Monthly Fee: $285
       Tax: $2,566 (2024)
    Community: Cypresswood Golf Villas Bldg G
    Villa


    Estimated Monthly Payment: $1,499 (change assumption)
    Mortgage ($1,000) + Fees ($285) + Taxes in 2024 ($214)


    Taxes:$2,566

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 634 WEXFORD CT, WINTER HAVEN, FL 33884

    $244,90083 Days on yellowkey   MLS ID: L4958804

    For Sale L4958804 - 634 WEXFORD CT, WINTER HAVEN, FL 33884 30 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1328
       Built: 1980
    Monthly Fee: $130
       Tax: $1,723 (2025)
    Community: Cypresswood Patio Homes
    Single Family


    Estimated Monthly Payment: $1,615 (change assumption)
    Mortgage ($1,342) + Fees ($130) + Taxes in 2025 ($144)


    Taxes:$1,723

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2968 PLANTATION RD, WINTER HAVEN, FL 33884

    $465,00027 Days on yellowkey   MLS ID: P4938120

    0 Days Off yellowkey (back on 4/1/2026)

    For Sale P4938120 - 2968 PLANTATION RD, WINTER HAVEN, FL 33884 82 photos

    Bed: 2   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2433
       Built: 1997
    Monthly Fee: $149
       Tax: $3,191 (2025)
    Community: Cypresswood Plantations
    Single Family


    Estimated Monthly Payment: $2,963 (change assumption)
    Mortgage ($2,548) + Fees ($149) + Taxes in 2025 ($266)


    Taxes:$3,191

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1012 MEDINAH DR SE, WINTER HAVEN, FL 33884

    $187,900231 Days on yellowkey   MLS ID: P4936101

    For Sale P4936101 - 1012 MEDINAH DR SE, WINTER HAVEN, FL 33884 58 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1458
       Built: 1981
    Monthly Fee: $320
       Tax: $2,740 (2025)
    Community: Cypresswood
    Spa: No

    Villa


    Estimated Monthly Payment: $1,578 (change assumption)
    Mortgage ($1,030) + Fees ($320) + Taxes in 2025 ($228)


    Taxes:$2,740

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 606 TURNBERRY CT, WINTER HAVEN, FL 33884

    $280,00029 Days on yellowkey   MLS ID: O6390721

    4 Days Off yellowkey (back on 4/6/2026)

    For Sale O6390721 - 606 TURNBERRY CT, WINTER HAVEN, FL 33884 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1891
       Built: 1980
    Monthly Fee: $17
       Tax: $3,745 (2025)
    Community: Cypresswood Patio Homes
    Single Family


    Estimated Monthly Payment: $1,863 (change assumption)
    Mortgage ($1,534) + Fees ($17) + Taxes in 2025 ($312)


    Taxes:$3,745

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 260 GREENFIELD RD, WINTER HAVEN, FL 33884

    $393,00065 Days on yellowkey   MLS ID: P4937787

    For Sale P4937787 - 260 GREENFIELD RD, WINTER HAVEN, FL 33884 52 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1947
       Built: 1978
    Monthly Fee: $152
       Tax: $5,885 (2025)
    Community: Cypresswood Greenfield Village
    Single Family


    Estimated Monthly Payment: $2,796 (change assumption)
    Mortgage ($2,153) + Fees ($152) + Taxes in 2025 ($490)


    Taxes:$5,885

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 688 AUGUSTA RD, WINTER HAVEN, FL 33884

    $337,00050 Days on yellowkey   MLS ID: P4937966

    For Sale P4937966 - 688 AUGUSTA RD, WINTER HAVEN, FL 33884 24 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1586
       Built: 1980
    Monthly Fee: $137
       Tax: $3,636 (2025)
    Community: Cypresswood Fairway Patio Homes
    Single Family


    Estimated Monthly Payment: $2,287 (change assumption)
    Mortgage ($1,847) + Fees ($137) + Taxes in 2025 ($303)


    Taxes:$3,636

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 649 BROADMOOR CIR, WINTER HAVEN, FL 33884

    $149,900183 Days on yellowkey   MLS ID: O6352259

    3 Days Off yellowkey (back on 3/9/2026)

    For Sale O6352259 - 649 BROADMOOR CIR, WINTER HAVEN, FL 33884 35 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1278
       Built: 1981
    Monthly Fee: $290
       Tax: $2,570 (2024)
    Community: Cypresswood Golf Villas
    Villa


    Estimated Monthly Payment: $1,326 (change assumption)
    Mortgage ($821) + Fees ($290) + Taxes in 2024 ($214)


    Taxes:$2,570

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2984 PLANTATION RD, WINTER HAVEN, FL 33884

    $455,00031 Days on yellowkey   MLS ID: P4938154

    0 Days Off yellowkey (back on 4/1/2026)

    For Sale P4938154 - 2984 PLANTATION RD, WINTER HAVEN, FL 33884 38 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2520
       Built: 1991
    Monthly Fee: $137
       Tax: $3,236 (2025)
    Community: Cypresswood Plantations
    Single Family


    Estimated Monthly Payment: $2,900 (change assumption)
    Mortgage ($2,493) + Fees ($137) + Taxes in 2025 ($270)


    Taxes:$3,236

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 241 GREENFIELD RD, WINTER HAVEN, FL 33884

    $369,95057 Days on yellowkey   MLS ID: L4959462

    REDUCED by $10,000 (2.6%) on 03/31/2026

    For Sale L4959462 - 241 GREENFIELD RD, WINTER HAVEN, FL 33884 43 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 2523
       Built: 1976
    Monthly Fee: $152
       Tax: $4,915 (2025)
    Community: Cypresswood
    Single Family


    Estimated Monthly Payment: $2,589 (change assumption)
    Mortgage ($2,027) + Fees ($152) + Taxes in 2025 ($410)


    Taxes:$4,915

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 730 CANBERRA RD, WINTER HAVEN, FL 33884

    $250,00051 Days on yellowkey   MLS ID: P4937918

    For Sale P4937918 - 730 CANBERRA RD, WINTER HAVEN, FL 33884 42 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1571
       Built: 1985
    Monthly Fee: $17
       Tax: $1,363 (2025)
    Community: Cypresswood Patio Homes
    Single Family


    Estimated Monthly Payment: $1,500 (change assumption)
    Mortgage ($1,370) + Fees ($17) + Taxes in 2025 ($114)


    Taxes:$1,363

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14 ENCLAVE DR, WINTER HAVEN, FL 33884

    $239,900254 Days on yellowkey   MLS ID: P4935733

    For Sale P4935733 - 14 ENCLAVE DR, WINTER HAVEN, FL 33884 31 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1368
       Built: 1995
    Monthly Fee: $429
       Tax: $3,033 (2024)
    Community: Cypresswood Enclave Ph 01
    Villa


    Estimated Monthly Payment: $1,996 (change assumption)
    Mortgage ($1,314) + Fees ($429) + Taxes in 2024 ($253)


    Taxes:$3,033

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 459 PINEHURST CT, WINTER HAVEN, FL 33884

    $214,90056 Days on yellowkey   MLS ID: P4937883

    0 Days Off yellowkey (back on 3/29/2026)

    For Sale P4937883 - 459 PINEHURST CT, WINTER HAVEN, FL 33884 50 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1258
       Built: 1979
    Monthly Fee: $144
       Tax: $1,449 (2025)
    Community: Cypresswood Patio Homes
    Single Family


    Estimated Monthly Payment: $1,442 (change assumption)
    Mortgage ($1,178) + Fees ($144) + Taxes in 2025 ($121)


    Taxes:$1,449

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


12


Why Bother Searching Elsewhere for Cypresswood Homes for Sale and Other Winter Haven Real Estate?

Cypresswood home, townhome, condo, villa, and other listing sales data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on houses for sale in Cypresswood. You can use our website to view Multiple Listing Service (MLS) data on Cypresswood Real Estate. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our Cypresswood. Winter Haven listings.



Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.