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Winter Haven Short Sales - 48 homes

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

Location: Winter Haven

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  • 1040 CAMBRIDGE DR, WINTER HAVEN, FL 33881

    $235,00010 Days on yellowkey   MLS ID: OM727915

    0 Days Off yellowkey (back on 7/13/2026)

    SHORT SALE OM727915 - 1040 CAMBRIDGE DR, WINTER HAVEN, FL 33881 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1727
       Built: 2021
    Monthly Fee: $17
       Tax: $7,188 (2025)
    Community: Lucerne Park Reserve
    Single Family


    Estimated Monthly Payment: $1,904 (change assumption)
    Mortgage ($1,288) + Fees ($17) + Taxes in 2025 ($599)


    Taxes:$7,188

    Elementary School: Lake Alfred Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 415 GARRETT RIDGE CT, WINTER HAVEN, FL 33880

    $140,000143 Days on yellowkey   MLS ID: O6383855

    0 Days Off yellowkey (back on 3/6/2026)

    SHORT SALE O6383855 - 415 GARRETT RIDGE CT, WINTER HAVEN, FL 33880 19 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1248
       Built: 2006   Tax: $3,078 (2025)
    Community: Tanamora
    Single Family


    Estimated Monthly Payment: $1,024 (change assumption)
    Mortgage ($767) + Taxes in 2025 ($257)


    Taxes:$3,078

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 400 EL CAMINO DR #210, WINTER HAVEN, FL 33884

    $120,000168 Days on yellowkey   MLS ID: S5142500

    REDUCED by $10,000 (7.7%) on 07/10/2026

    SHORT SALE S5142500 - 400 EL CAMINO DR #210, WINTER HAVEN, FL 33884 33 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1666
       Built: 1974
    Monthly Fee: $448
       Tax: $1,368 (2025)
    Community: Orchid Spgs Vill 400 San Miguel
    Spa: No

    Condo


    Estimated Monthly Payment: $1,220 (change assumption)
    Mortgage ($658) + Fees ($448) + Taxes in 2025 ($114)


    Taxes:$1,368

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 404 COUNTRY LN NE #404, WINTER HAVEN, FL 33881

    $80,000102 Days on yellowkey   MLS ID: L4960788

    REDUCED by $25,000 (23.8%) on 07/10/2026

    SHORT SALE L4960788 - 404 COUNTRY LN NE #404, WINTER HAVEN, FL 33881 21 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1252
       Built: 1985
    Monthly Fee: $325
       Tax: $1,415 (2025)
    Community: Country Lake Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $881 (change assumption)
    Mortgage ($438) + Fees ($325) + Taxes in 2025 ($118)


    Taxes:$1,415

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 113 CITRUS DR, WINTER HAVEN, FL 33884

    $259,000151 Days on yellowkey   MLS ID: O6382305

    REDUCED by $4,500 (1.7%) on 07/10/2026

    SHORT SALE O6382305 - 113 CITRUS DR, WINTER HAVEN, FL 33884 3 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2016
       Built: 1960   Tax: $3,241 (2024)
    Community: Elwood Heights
    Single Family


    Estimated Monthly Payment: $1,689 (change assumption)
    Mortgage ($1,419) + Taxes in 2024 ($270)


    Taxes:$3,241

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 503 HOLT CIR, WINTER HAVEN, FL 33880

    $185,000429 Days on yellowkey   MLS ID: TB8384455

    0 Days Off yellowkey (back on 6/1/2026)

    SHORT SALE TB8384455 - 503 HOLT CIR, WINTER HAVEN, FL 33880 70 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1305
       Built: 1974   Tax: $2,956 (2024)
    Community: Jan Phyl Village
    Single Family


    Estimated Monthly Payment: $1,260 (change assumption)
    Mortgage ($1,014) + Taxes in 2024 ($246)


    Taxes:$2,956

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Westwood Middle


  • 3935 PALAZZO PL, WINTER HAVEN, FL 33884

    $290,000126 Days on yellowkey   MLS ID: L4960079

    SHORT SALE L4960079 - 3935 PALAZZO PL, WINTER HAVEN, FL 33884 43 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2601
       Built: 2023
    Monthly Fee: $250
       Tax: $6,788 (2025)
    Community: Villamar
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,405 (change assumption)
    Mortgage ($1,589) + Fees ($250) + Taxes in 2025 ($566)


    Taxes:$6,788

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: McLaughlin Academy Of Excellence


  • 909 CAMBRIDGE DR, WINTER HAVEN, FL 33881

    $266,90087 Days on yellowkey   MLS ID: G5111142

    REDUCED by $5,000 (1.8%) on 07/07/2026

    SHORT SALE G5111142 - 909 CAMBRIDGE DR, WINTER HAVEN, FL 33881 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1506
       Built: 2022
    Monthly Fee: $13
       Tax: $3,310 (2025)
    Community: Lucerne Park Reserve
    Single Family


    Estimated Monthly Payment: $1,751 (change assumption)
    Mortgage ($1,462) + Fees ($13) + Taxes in 2025 ($276)


    Taxes:$3,310

    Elementary School: Fred G. Garnier Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 884 CAMBRIDGE DR, WINTER HAVEN, FL 33881

    $287,50077 Days on yellowkey   MLS ID: TB8502061

    INCREASED by $12,500 (4.5%) on 07/06/2026

    SHORT SALE TB8502061 - 884 CAMBRIDGE DR, WINTER HAVEN, FL 33881 26 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2368
       Built: 2021
    Monthly Fee: $17
       Tax: $7,314 (2025)
    Community: Lucerne Park Reserve
    Single Family


    Estimated Monthly Payment: $2,202 (change assumption)
    Mortgage ($1,575) + Fees ($17) + Taxes in 2025 ($610)


    Taxes:$7,314

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4913 JACKSON ST, WINTER HAVEN, FL 33884

    $239,900176 Days on yellowkey   MLS ID: O6374521

    2 Days Off yellowkey (back on 3/30/2026)

    SHORT SALE O6374521 - 4913 JACKSON ST, WINTER HAVEN, FL 33884 10 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1425
       Built: 2023
    Monthly Fee: $67
       Tax: $3,152 (2025)
    Community: Jackson Lndg
    Single Family


    Estimated Monthly Payment: $1,644 (change assumption)
    Mortgage ($1,314) + Fees ($67) + Taxes in 2025 ($263)


    Taxes:$3,152

    Elementary School: Garden Grove Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 440 KENSINGTON VIEW DR, WINTER HAVEN, FL 33880

    $263,000211 Days on yellowkey   MLS ID: G5105497

    1 Days Off yellowkey (back on 4/15/2026)

    INCREASED by $23,000 (9.6%) on 04/15/2026

    SHORT SALE G5105497 - 440 KENSINGTON VIEW DR, WINTER HAVEN, FL 33880 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1688
       Built: 2020
    Monthly Fee: $53
       Tax: $3,809 (2024)
    Community: Kensington View
    Single Family


    Estimated Monthly Payment: $1,812 (change assumption)
    Mortgage ($1,441) + Fees ($53) + Taxes in 2024 ($317)


    Taxes:$3,809

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6518 CRESCENT LOOP, WINTER HAVEN, FL 33884

    $249,000142 Days on yellowkey   MLS ID: O6384613

    1 Days Off yellowkey (back on 7/1/2026)

    REDUCED by $2,250,000 (90.0%) on 04/24/2026

    SHORT SALE O6384613 - 6518 CRESCENT LOOP, WINTER HAVEN, FL 33884 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1894
       Built: 2016
    Monthly Fee: $50
       Tax: $4,986 (2025)
    Community: Crescent View
    Single Family


    Estimated Monthly Payment: $1,830 (change assumption)
    Mortgage ($1,364) + Fees ($50) + Taxes in 2025 ($415)


    Taxes:$4,986

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3815 POMELO, WINTER HAVEN, FL 33884

    $304,900140 Days on yellowkey   MLS ID: O6384844

    REDUCED by $3,000 (1.0%) on 06/30/2026

    SHORT SALE O6384844 - 3815 POMELO, WINTER HAVEN, FL 33884 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1672
       Built: 2026
    Monthly Fee: $30
       Tax: $155 (2025)
    Community: Harmony On Lake Eloise
    Single Family


    Estimated Monthly Payment: $1,714 (change assumption)
    Mortgage ($1,671) + Fees ($30) + Taxes in 2025 ($13)


    Taxes:$155

    Elementary School: John Snively Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 124 CENTER ST, WINTER HAVEN, FL 33880

    $180,00033 Days on yellowkey   MLS ID: L4962572

    REDUCED by $10,000 (5.3%) on 07/01/2026

    SHORT SALE L4962572 - 124 CENTER ST, WINTER HAVEN, FL 33880 36 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1306
       Built: 1952   Tax: $2,590 (2025)
    Community: Lake Shipp Heights
    Single Family


    Estimated Monthly Payment: $1,202 (change assumption)
    Mortgage ($986) + Taxes in 2025 ($216)


    Taxes:$2,590

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 273 HAYLEY ST, WINTER HAVEN, FL 33884

    $243,000171 Days on yellowkey   MLS ID: O6375357

    0 Days Off yellowkey (back on 7/1/2026)

    INCREASED by $3,000 (1.3%) on 07/01/2026

    SHORT SALE O6375357 - 273 HAYLEY ST, WINTER HAVEN, FL 33884 14 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1432
       Built: 2024
    Monthly Fee: $16
       Tax: $6,815 (2025)
    Community: Peace Crk Reserve
    Single Family


    Estimated Monthly Payment: $1,915 (change assumption)
    Mortgage ($1,331) + Fees ($16) + Taxes in 2025 ($568)


    Taxes:$6,815

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4223 SAN ROCCO WAY, WINTER HAVEN, FL 33884

    $280,000263 Days on yellowkey   MLS ID: S5137072

    1 Days Off yellowkey (back on 6/29/2026)

    REDUCED by $45,000 (13.8%) on 06/17/2026

    SHORT SALE S5137072 - 4223 SAN ROCCO WAY, WINTER HAVEN, FL 33884 47 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2522
       Built: 2023
    Monthly Fee: $22
       Tax: $7,612 (2024)
    Community: Villamar Ph 5
    Single Family


    Estimated Monthly Payment: $2,191 (change assumption)
    Mortgage ($1,534) + Fees ($22) + Taxes in 2024 ($634)


    Taxes:$7,612

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Denison Middle


  • 3098 LAUREL OAK LN, WINTER HAVEN, FL 33884

    $245,000102 Days on yellowkey   MLS ID: O6390090

    REDUCED by $15,000 (5.8%) on 06/26/2026

    SHORT SALE O6390090 - 3098 LAUREL OAK LN, WINTER HAVEN, FL 33884 13 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1978
       Built: 2023
    Monthly Fee: $18
       Tax: $6,208 (2025)
    Community: Villamar Ph 5
    Single Family


    Estimated Monthly Payment: $1,878 (change assumption)
    Mortgage ($1,342) + Fees ($18) + Taxes in 2025 ($517)


    Taxes:$6,208

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 602 TAYLOR BLVD, WINTER HAVEN, FL 33880

    $220,000283 Days on yellowkey   MLS ID: P4936558

    1 Days Off yellowkey (back on 6/26/2026)

    SHORT SALE P4936558 - 602 TAYLOR BLVD, WINTER HAVEN, FL 33880 19 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1242
       Built: 1973   Tax: $3,093 (2024)
    Community: Jan Phyl Village
    Single Family


    Estimated Monthly Payment: $1,463 (change assumption)
    Mortgage ($1,205) + Taxes in 2024 ($258)


    Taxes:$3,093

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Westwood Middle


  • 3530 EVENING STAR DR, WINTER HAVEN, FL 33881

    $315,00019 Days on yellowkey   MLS ID: TB8523082

    SHORT SALE TB8523082 - 3530 EVENING STAR DR, WINTER HAVEN, FL 33881 1 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1822
       Built: 2025
    Monthly Fee: $58
       Tax: $951 (2025)
    Community: Sunset Hills
    Single Family


    Estimated Monthly Payment: $1,863 (change assumption)
    Mortgage ($1,726) + Fees ($58) + Taxes in 2025 ($79)


    Taxes:$951

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 302 STERLING DR, WINTER HAVEN, FL 33884

    $365,00019 Days on yellowkey   MLS ID: O6419370

    SHORT SALE O6419370 - 302 STERLING DR, WINTER HAVEN, FL 33884 13 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2460
       Built: 1994
    Monthly Fee: $24
       Tax: $2,764 (2025)
    Community: Berryhill
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,254 (change assumption)
    Mortgage ($2,000) + Fees ($24) + Taxes in 2025 ($230)


    Taxes:$2,764

    Elementary School: Garden Grove Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


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Winter Haven home, townhome, and 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 short sale homes in Winter Haven. You can use our website to view Multiple Listing Service (MLS) data on Winter Haven short sale properties. 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 short sale 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.