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Winter Haven Single Family Homes For Sale - 810 homes

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

Location: Winter Haven

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  • 3006 ELM ST, WINTER HAVEN, FL 33881

    $215,00070 Days on yellowkey   MLS ID: P4938656

    For Sale P4938656 - 3006 ELM ST, WINTER HAVEN, FL 33881 34 photos

    Bed: 3   Bath: 1.5
    Liv Area Sq Ft: 1172
       Built: 1955   Tax: $2,592 (2025)
    Community: Biltmore Shores
    Single Family


    Estimated Monthly Payment: $1,394 (change assumption)
    Mortgage ($1,178) + Taxes in 2025 ($216)


    Taxes:$2,592

    Elementary School: Auburndale Central Elem

    High School: Auburndale High School

    Tax Year: 2025

    Middle School: Westwood Middle


  • 357 RUBY LAKE LOOP, WINTER HAVEN, FL 33884

    $415,000117 Days on yellowkey   MLS ID: L4960449

    For Sale L4960449 - 357 RUBY LAKE LOOP, WINTER HAVEN, FL 33884 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2107
       Built: 1998
    Monthly Fee: $71
       Tax: $2,731 (2025)
    Community: Ruby Lake Ph 01
    Single Family


    Estimated Monthly Payment: $2,573 (change assumption)
    Mortgage ($2,274) + Fees ($71) + Taxes in 2025 ($228)


    Taxes:$2,731

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 820 AVENUE Z NW, WINTER HAVEN, FL 33881

    $197,50048 Days on yellowkey   MLS ID: S5150017

    SHORT SALE S5150017 - 820 AVENUE Z NW, WINTER HAVEN, FL 33881 1 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2082
       Built: 1925   Tax: $3,824 (2025)
    Community: Hartridge Manor
    Single Family


    Estimated Monthly Payment: $1,401 (change assumption)
    Mortgage ($1,082) + Taxes in 2025 ($319)


    Taxes:$3,824

    Elementary School: Frank E. Brigham Academy

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: None


  • 2968 PLANTATION RD, WINTER HAVEN, FL 33884

    $442,000117 Days on yellowkey   MLS ID: P4938120

    0 Days Off yellowkey (back on 5/30/2026)

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

    For Sale P4938120 - 2968 PLANTATION RD, WINTER HAVEN, FL 33884 83 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


  • 780 OVERLOOK GROVE DR, WINTER HAVEN, FL 33884

    $272,50077 Days on yellowkey   MLS ID: L4960255

    REDUCED by $22,500 (7.6%) on 06/12/2026

    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: $1,889 (change assumption)
    Mortgage ($1,493) + Fees ($38) + Taxes in 2025 ($358)


    Taxes:$4,294

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 335 RUBY LAKE LOOP, WINTER HAVEN, FL 33884

    $484,90040 Days on yellowkey   MLS ID: L4962358

    0 Days Off yellowkey (back on 6/12/2026)

    For Sale L4962358 - 335 RUBY LAKE LOOP, WINTER HAVEN, FL 33884 66 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2406
       Built: 1999
    Monthly Fee: $71
       Tax: $3,154 (2025)
    Community: Ruby Lake Ph 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,991 (change assumption)
    Mortgage ($2,657) + Fees ($71) + Taxes in 2025 ($263)


    Taxes:$3,154

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 2540 14TH ST SE, WINTER HAVEN, FL 33884

    $369,90049 Days on yellowkey   MLS ID: O6411362

    2 Days Off yellowkey (back on 6/12/2026)

    For Sale O6411362 - 2540 14TH ST SE, WINTER HAVEN, FL 33884 30 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1753
       Built: 1956   Tax: $3,789 (2025)
    Community: South Roy Shores
    Single Family


    Estimated Monthly Payment: $2,343 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($316)


    Taxes:$3,789

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 1195 TYLER LOOP, WINTER HAVEN, FL 33884

    $299,997188 Days on yellowkey   MLS ID: O6371574

    For Sale O6371574 - 1195 TYLER LOOP, WINTER HAVEN, FL 33884 21 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1933
       Built: 2024
    Monthly Fee: $16
       Tax: $7,112 (2025)
    Community: Peace Crk Reserve
    Single Family


    Estimated Monthly Payment: $2,252 (change assumption)
    Mortgage ($1,644) + Fees ($16) + Taxes in 2025 ($593)


    Taxes:$7,112

    Elementary School: South Pointe Elementary

    High School: None

    Tax Year: 2025

    Middle School: McLaughlin Academy Of Excellence


  • 5445 CHANDLER DR, WINTER HAVEN, FL 33884

    $305,000120 Days on yellowkey   MLS ID: S5146003

    REDUCED by $9,500 (3.0%) on 06/11/2026

    For Sale S5146003 - 5445 CHANDLER DR, WINTER HAVEN, FL 33884 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3010
       Built: 2006
    Monthly Fee: $48
       Tax: $5,827 (2025)
    Community: Bentley Place
    Single Family


    Estimated Monthly Payment: $2,205 (change assumption)
    Mortgage ($1,671) + Fees ($48) + Taxes in 2025 ($486)


    Taxes:$5,827

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1192 NORMANDY HEIGHTS CIR, WINTER HAVEN, FL 33880

    $338,00089 Days on yellowkey   MLS ID: L4961188

    REDUCED by $6,900 (2.0%) on 05/08/2026

    For Sale L4961188 - 1192 NORMANDY HEIGHTS CIR, WINTER HAVEN, FL 33880 48 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2093
       Built: 2009
    Monthly Fee: $50
       Tax: $4,839 (2025)
    Community: Normandy Heights
    Single Family


    Estimated Monthly Payment: $2,305 (change assumption)
    Mortgage ($1,852) + Fees ($50) + Taxes in 2025 ($403)


    Taxes:$4,839

    Elementary School: Lake Shipp Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 1454 GRAND CAYMAN CIR, WINTER HAVEN, FL 33884

    $249,990101 Days on yellowkey   MLS ID: O6396319

    REDUCED by $10,000 (3.8%) on 06/10/2026

    For Sale O6396319 - 1454 GRAND CAYMAN CIR, WINTER HAVEN, FL 33884 50 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1596
       Built: 1987
    Monthly Fee: $45
       Tax: $2,901 (2025)
    Community: Lake Dexter Moorings
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,656 (change assumption)
    Mortgage ($1,370) + Fees ($45) + Taxes in 2025 ($242)


    Taxes:$2,901

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 250 BRIGHAM RD NW, WINTER HAVEN, FL 33881

    $1,195,00054 Days on yellowkey   MLS ID: L4962128

    For Sale L4962128 - 250 BRIGHAM RD NW, WINTER HAVEN, FL 33881 67 photos

    Bed: 5   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 3235
       Built: 1971   Tax: $8,444 (2025)
    Community: Na
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,251 (change assumption)
    Mortgage ($6,548) + Taxes in 2025 ($704)


    Taxes:$8,444

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5125 SYLAS JAX AVE, WINTER HAVEN, FL 33884

    $259,900111 Days on yellowkey   MLS ID: L4960626

    REDUCED by $6,000 (2.3%) on 06/10/2026

    For Sale L4960626 - 5125 SYLAS JAX AVE, WINTER HAVEN, FL 33884 10 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1358
       Built: 2025
    Monthly Fee: $18

    Community: Villamar
    Single Family


    Estimated Monthly Payment: $1,442 (change assumption)
    Mortgage ($1,424) + Fees ($18) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5456 SAN PIETRO DR, WINTER HAVEN, FL 33884

    $349,49973 Days on yellowkey   MLS ID: TB8504505

    0 Days Off yellowkey (back on 6/9/2026)

    REDUCED by $500 (0.1%) on 05/19/2026

    For Sale TB8504505 - 5456 SAN PIETRO DR, WINTER HAVEN, FL 33884 19 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2471
       Built: 2026
    Monthly Fee: $53
       Tax: $4,690 (2025)
    Community: Villa Mar
    Single Family


    Estimated Monthly Payment: $2,359 (change assumption)
    Mortgage ($1,915) + Fees ($53) + Taxes in 2025 ($391)


    Taxes:$4,690

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 693 SQUIRES GROVE DR, WINTER HAVEN, FL 33880

    $264,90077 Days on yellowkey   MLS ID: TB8502032

    REDUCED by $5,100 (1.9%) on 06/09/2026

    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: $1,848 (change assumption)
    Mortgage ($1,451) + 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


  • 1601 ROSELAWN ST SW, WINTER HAVEN, FL 33880

    $256,500257 Days on yellowkey   MLS ID: O6356028

    REDUCED by $500 (0.2%) on 06/09/2026

    For Sale O6356028 - 1601 ROSELAWN ST SW, WINTER HAVEN, FL 33880 13 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1099
       Built: 1960   Tax: $3,654 (2024)
    Community: Tranquility Park 02 Rep
    Single Family


    Estimated Monthly Payment: $1,710 (change assumption)
    Mortgage ($1,405) + Taxes in 2024 ($305)


    Taxes:$3,654

    Elementary School: Lake Shipp Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Denison Middle


  • 217 4TH JPV ST, WINTER HAVEN, FL 33880

    $245,00040 Days on yellowkey   MLS ID: L4962456

    For Sale L4962456 - 217 4TH JPV ST, WINTER HAVEN, FL 33880 20 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1064
       Built: 1962   Tax: $1,280 (2025)
    Community: Jan Phyl Village Unit 03 A
    Single Family


    Estimated Monthly Payment: $1,449 (change assumption)
    Mortgage ($1,342) + Taxes in 2025 ($107)


    Taxes:$1,280

    Elementary School: Fred G. Garnier Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood Middle


  • 6003 LIVE OAK DR, WINTER HAVEN, FL 33880

    $364,999125 Days on yellowkey   MLS ID: S5145500

    2 Days Off yellowkey (back on 6/9/2026)

    REDUCED by $4,000 (1.1%) on 05/16/2026

    For Sale S5145500 - 6003 LIVE OAK DR, WINTER HAVEN, FL 33880 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1907
       Built: 2006
    Monthly Fee: $20
       Tax: $2,549 (2025)
    Community: Oak Preserve Ph 02
    Single Family


    Estimated Monthly Payment: $2,232 (change assumption)
    Mortgage ($2,000) + Fees ($20) + Taxes in 2025 ($212)


    Taxes:$2,549

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 276 MEREDITH BLVD, WINTER HAVEN, FL 33881

    $329,99037 Days on yellowkey   MLS ID: G5113493

    0 Days Off yellowkey (back on 6/8/2026)

    For Sale G5113493 - 276 MEREDITH BLVD, WINTER HAVEN, FL 33881 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2110
       Built: 2025
    Monthly Fee: $7
       Tax: $500 (2025)
    Community: Willowbrook North
    Single Family


    Estimated Monthly Payment: $1,857 (change assumption)
    Mortgage ($1,808) + Fees ($7) + Taxes in 2025 ($42)


    Taxes:$500

    Elementary School: Fred G. Garnier Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 151 1ST ST S, WINTER HAVEN, FL 33880

    $258,00037 Days on yellowkey   MLS ID: O6413676

    For Sale O6413676 - 151 1ST ST S, WINTER HAVEN, FL 33880 2 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1259
       Built: 2024   Tax: $2,032 (2025)
    Community: Leslie J A Sub
    Single Family


    Estimated Monthly Payment: $1,583 (change assumption)
    Mortgage ($1,414) + Taxes in 2025 ($169)


    Taxes:$2,032

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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Winter Haven home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Winter Haven. You can use our website to view Multiple Listing Service (MLS) data on Winter Haven single family homes. 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 single family home 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.