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Winter Haven Homes For Sale & Real Estate - 927 homes

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

Location: Winter Haven

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  • 2968 PLANTATION RD, WINTER HAVEN, FL 33884

    $442,00041 Days on yellowkey   MLS ID: P4938120

    REDUCED by $23,000 (4.9%) on 04/23/2026

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

    Bed: 3   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: $2,837 (change assumption)
    Mortgage ($2,422) + Fees ($149) + Taxes in 2025 ($266)


    Taxes:$3,191

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2964 PLANTATION RD, WINTER HAVEN, FL 33884

    $579,900196 Days on yellowkey   MLS ID: O6352519

    REDUCED by $20,000 (3.3%) on 04/30/2026

    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: $3,366 (change assumption)
    Mortgage ($3,177) + Fees ($137) + Taxes in 2024 ($52)


    Taxes:$618

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1700 6TH ST NW #C31, WINTER HAVEN, FL 33881

    $99,90076 Days on yellowkey   MLS ID: L4959370

    REDUCED by $9,890 (9.0%) on 04/30/2026

    For Sale L4959370 - 1700 6TH ST NW #C31, WINTER HAVEN, FL 33881 22 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 840
       Built: 1964
    Monthly Fee: $350
       Tax: $1,336 (2025)
    Community: Winter Haven Harbour Apts Condo
    Condo


    Estimated Monthly Payment: $1,009 (change assumption)
    Mortgage ($547) + Fees ($350) + Taxes in 2025 ($111)


    Taxes:$1,336

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 693 SQUIRES GROVE DR, WINTER HAVEN, FL 33880

    $285,0001 Day on yellowkey   MLS ID: TB8502032

    For Sale TB8502032 - 693 SQUIRES GROVE DR, WINTER HAVEN, FL 33880 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1690
       Built: 2022
    Monthly Fee: $49
       Tax: $4,173 (2025)
    Community: Squires Grove Ph 2
    Single Family


    Estimated Monthly Payment: $1,958 (change assumption)
    Mortgage ($1,562) + Fees ($49) + Taxes in 2025 ($348)


    Taxes:$4,173

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood Middle


  • 4009 CYPRESS LNDG S, WINTER HAVEN, FL 33884

    $239,00044 Days on yellowkey   MLS ID: TB8487328

    REDUCED by $8,000 (3.2%) on 04/30/2026

    For Sale TB8487328 - 4009 CYPRESS LNDG S, WINTER HAVEN, FL 33884 43 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1291
       Built: 1987
    Monthly Fee: $83
       Tax: $3,230 (2025)
    Community: Cypress Landing Ph 02
    Single Family


    Estimated Monthly Payment: $1,662 (change assumption)
    Mortgage ($1,310) + Fees ($83) + Taxes in 2025 ($269)


    Taxes:$3,230

    Elementary School: Garden Grove Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 601 LAKE PANSY DR NW, WINTER HAVEN, FL 33881

    $795,900106 Days on yellowkey   MLS ID: P4937480

    REDUCED by $19,100 (2.3%) on 04/30/2026

    For Sale P4937480 - 601 LAKE PANSY DR NW, WINTER HAVEN, FL 33881 48 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2140
       Built: 1977   Tax: $760 (2025)
    Community: Not In Subdivision
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,424 (change assumption)
    Mortgage ($4,361) + Taxes in 2025 ($63)


    Taxes:$760

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1290 N LAKE SHIPP DR N, WINTER HAVEN, FL 33880

    $795,00013 Days on yellowkey   MLS ID: L4961193

    For Sale L4961193 - 1290 N LAKE SHIPP DR N, WINTER HAVEN, FL 33880 47 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2001
       Built: 2021   Tax: $7,094 (2025)
    Community: N/A
    Single Family


    Estimated Monthly Payment: $4,947 (change assumption)
    Mortgage ($4,356) + Taxes in 2025 ($591)


    Taxes:$7,094

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 780 OVERLOOK GROVE DR, WINTER HAVEN, FL 33884

    $302,5001 Day on yellowkey   MLS ID: L4960255

    For Sale L4960255 - 780 OVERLOOK GROVE DR, WINTER HAVEN, FL 33884 45 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1583
       Built: 2013
    Monthly Fee: $38
       Tax: $4,294 (2025)
    Community: Overlook Rdg
    Single Family


    Estimated Monthly Payment: $2,053 (change assumption)
    Mortgage ($1,657) + Fees ($38) + Taxes in 2025 ($358)


    Taxes:$4,294

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5200 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884

    $475,000304 Days on yellowkey   MLS ID: P4935325

    2 Days Off yellowkey (back on 4/25/2026)

    REDUCED by $35,000 (6.9%) on 04/16/2026

    For Sale P4935325 - 5200 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884 72 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2443
       Built: 2008
    Monthly Fee: $5
       Tax: $6,051 (2024)
    Community: Lake Ashton West Ph 01
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,112 (change assumption)
    Mortgage ($2,603) + Fees ($5) + Taxes in 2024 ($504)


    Taxes:$6,051

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6103 GREY HERON DR, WINTER HAVEN, FL 33881

    $305,000Listed 04/30/2026 8:59AM   MLS ID: O6403532

    For Sale O6403532 - 6103 GREY HERON DR, WINTER HAVEN, FL 33881 1 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1828
       Built: 2018
    Monthly Fee: $9
       Tax: $5,214 (2025)
    Community: Lakeside Landings Ph 01
    Single Family


    Estimated Monthly Payment: $2,115 (change assumption)
    Mortgage ($1,671) + Fees ($9) + Taxes in 2025 ($434)


    Taxes:$5,214

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 126 2ND ST, WINTER HAVEN, FL 33880

    $149,900107 Days on yellowkey   MLS ID: P4937521

    1 Days Off yellowkey (back on 4/30/2026)

    REDUCED by $10,000 (6.3%) on 04/08/2026

    For Sale P4937521 - 126 2ND ST, WINTER HAVEN, FL 33880 40 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 924
       Built: 2023   Tax: $1,796 (2025)
    Community: Leslie J A Sub
    Manufactured Home


    Estimated Monthly Payment: $971 (change assumption)
    Mortgage ($821) + Taxes in 2025 ($150)


    Taxes:$1,796

    Elementary School: John Snively Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 2436 EDWIN ST NE, WINTER HAVEN, FL 33881

    $249,74189 Days on yellowkey   MLS ID: P4937644

    REDUCED by $3 (0.0%) on 04/30/2026

    For Sale P4937644 - 2436 EDWIN ST NE, WINTER HAVEN, FL 33881 36 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1813
       Built: 2026   Tax: $313 (2025)
    Community: Smart Sub
    Spa: No

    Manufactured Home


    Estimated Monthly Payment: $1,394 (change assumption)
    Mortgage ($1,368) + Taxes in 2025 ($26)


    Taxes:$313

    Elementary School: Elbert Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 2 CASARENA CT, WINTER HAVEN, FL 33881

    $320,00093 Days on yellowkey   MLS ID: L4958770

    For Sale L4958770 - 2 CASARENA CT, WINTER HAVEN, FL 33881 44 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2377
       Built: 1983
    Monthly Fee: $310
       Tax: $5,755 (2025)
    Community: Casarena On Lakes
    Single Family


    Estimated Monthly Payment: $2,543 (change assumption)
    Mortgage ($1,753) + Fees ($310) + Taxes in 2025 ($480)


    Taxes:$5,755

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 120 MIRROR LN NW, WINTER HAVEN, FL 33881

    $995,0001 Day on yellowkey   MLS ID: L4961404

    For Sale L4961404 - 120 MIRROR LN NW, WINTER HAVEN, FL 33881 64 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3973
       Built: 1984   Tax: $7,496 (2025)
    Community: The Shores
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,077 (change assumption)
    Mortgage ($5,452) + Taxes in 2025 ($625)


    Taxes:$7,496

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6502 OAK HAMMOCK LN, WINTER HAVEN, FL 33884

    $169,000177 Days on yellowkey   MLS ID: P4936840

    For Sale P4936840 - 6502 OAK HAMMOCK LN, WINTER HAVEN, FL 33884 32 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1512
       Built: 1998
    Monthly Fee: $65
       Tax: $1,088 (2025)
    Community: Garden Grove Oaks
    Manufactured Home


    Estimated Monthly Payment: $1,082 (change assumption)
    Mortgage ($926) + Fees ($65) + Taxes in 2025 ($91)


    Taxes:$1,088

    Elementary School: Garden Grove Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 961 DREXEL AVE NE, WINTER HAVEN, FL 33881

    $315,00066 Days on yellowkey   MLS ID: L4959592

    REDUCED by $5,000 (1.6%) on 04/19/2026

    For Sale L4959592 - 961 DREXEL AVE NE, WINTER HAVEN, FL 33881 57 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1856
       Built: 1948   Tax: $3,409 (2025)
    Community: Anna Mar
    Single Family


    Estimated Monthly Payment: $2,010 (change assumption)
    Mortgage ($1,726) + Taxes in 2025 ($284)


    Taxes:$3,409

    Elementary School: Inwood Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Westwood Middle


  • 116 MANDOLIN DR, WINTER HAVEN, FL 33884

    $370,0001 Day on yellowkey   MLS ID: O6403313

    For Sale O6403313 - 116 MANDOLIN DR, WINTER HAVEN, FL 33884 51 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2248
       Built: 2009
    Monthly Fee: $56
       Tax: $5,678 (2025)
    Community: Mandolin
    Single Family


    Estimated Monthly Payment: $2,557 (change assumption)
    Mortgage ($2,027) + Fees ($56) + Taxes in 2025 ($473)


    Taxes:$5,678

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 316 LAKE SMART CIR, WINTER HAVEN, FL 33881

    $289,9001 Day on yellowkey   MLS ID: L4961472

    FORECLOSURE L4961472 - 316 LAKE SMART CIR, WINTER HAVEN, FL 33881 23 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1500
       Built: 2022
    Monthly Fee: $50
       Tax: $4,224 (2025)
    Community: Lake Smart Pointe
    Single Family


    Estimated Monthly Payment: $1,990 (change assumption)
    Mortgage ($1,588) + Fees ($50) + Taxes in 2025 ($352)


    Taxes:$4,224

    Elementary School: Lake Alfred Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 811 22ND ST NW, WINTER HAVEN, FL 33881

    $269,9901 Day on yellowkey   MLS ID: S5148769

    For Sale S5148769 - 811 22ND ST NW, WINTER HAVEN, FL 33881 39 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1408
       Built: 1953   Tax: $4,020 (2025)
    Community: Hutton Rep
    Single Family


    Estimated Monthly Payment: $1,814 (change assumption)
    Mortgage ($1,479) + Taxes in 2025 ($335)


    Taxes:$4,020

    Elementary School: Inwood Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Westwood Middle


  • 554 EAGLE LANDING BLVD, WINTER HAVEN, FL 33880

    $312,0001 Day on yellowkey   MLS ID: O6402516

    For Sale O6402516 - 554 EAGLE LANDING BLVD, WINTER HAVEN, FL 33880 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1628
       Built: 2021
    Monthly Fee: $38
       Tax: $3,739 (2025)
    Community: Eagle Lndg Ph I
    Single Family


    Estimated Monthly Payment: $2,059 (change assumption)
    Mortgage ($1,710) + Fees ($38) + Taxes in 2025 ($312)


    Taxes:$3,739

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle




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

Winter Haven 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 Winter Haven . You can use our website to view Multiple Listing Service (MLS) data on Winter Haven 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 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.