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Displaying: For Sale

Location: Winter Haven

Property Type(s): Single Family

Price: $300,000 to $399,000

Winter Haven - 287 properties found

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  • 1742 UPLAND LN, WINTER HAVEN, FL 33884

    $380,99063 Days on yellowkey   MLS ID: W7885110

    For Sale W7885110 - 1742 UPLAND LN, WINTER HAVEN, FL 33884 17 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2250
       Built: 2026
    Monthly Fee: $63

    Community: Ashton Covey
    Single Family


    Estimated Monthly Payment: $2,151 (change assumption)
    Mortgage ($2,088) + Fees ($63) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2026

    Middle School: McLaughlin Academy Of Excellence


  • 643 GROVE ST, WINTER HAVEN, FL 33881

    $340,000142 Days on yellowkey   MLS ID: O6379127

    For Sale O6379127 - 643 GROVE ST, WINTER HAVEN, FL 33881 16 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1853
       Built: 2022
    Monthly Fee: $50
       Tax: $5,200 (2024)
    Community: Inman Groves
    Single Family


    Estimated Monthly Payment: $2,346 (change assumption)
    Mortgage ($1,863) + Fees ($50) + Taxes in 2024 ($433)


    Taxes:$5,200

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Denison Middle


  • 2108 CARTGATE LN, WINTER HAVEN, FL 33884

    $310,00026 Days on yellowkey   MLS ID: P4938873

    For Sale P4938873 - 2108 CARTGATE LN, WINTER HAVEN, FL 33884 56 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1961
       Built: 2023
    Monthly Fee: $18
       Tax: $6,185 (2025)
    Community: Villamar Ph 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,232 (change assumption)
    Mortgage ($1,699) + Fees ($18) + Taxes in 2025 ($515)


    Taxes:$6,185

    Elementary School: Chain O Lakes Elem

    High School: None

    Tax Year: 2025

    Middle School: McLaughlin Academy Of Excellence


  • 144 BEVERLY DR, WINTER HAVEN, FL 33884

    $389,90075 Days on yellowkey   MLS ID: O6397768

    REDUCED by $9,600 (2.4%) on 06/03/2026

    For Sale O6397768 - 144 BEVERLY DR, WINTER HAVEN, FL 33884 20 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2492
       Built: 1963   Tax: $3,785 (2025)
    Community: Eloise Woods Lake Roy Unit
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,452 (change assumption)
    Mortgage ($2,136) + Taxes in 2025 ($315)


    Taxes:$3,785

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 287 INMAN BLVD, WINTER HAVEN, FL 33881

    $315,00082 Days on yellowkey   MLS ID: S5147134

    For Sale S5147134 - 287 INMAN BLVD, WINTER HAVEN, FL 33881 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1560
       Built: 2023
    Monthly Fee: $49
       Tax: $3,542 (2025)
    Community: Inman Grvs Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,070 (change assumption)
    Mortgage ($1,726) + Fees ($49) + Taxes in 2025 ($295)


    Taxes:$3,542

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 3927 PALAZZO PL, WINTER HAVEN, FL 33884

    $300,000125 Days on yellowkey   MLS ID: O6383833

    REDUCED by $3,000 (1.0%) on 06/20/2026

    For Sale O6383833 - 3927 PALAZZO PL, WINTER HAVEN, FL 33884 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1597
       Built: 2023
    Monthly Fee: $40
       Tax: $4,716 (2025)
    Community: Villamar Ph 4
    Single Family


    Estimated Monthly Payment: $2,077 (change assumption)
    Mortgage ($1,644) + Fees ($40) + Taxes in 2025 ($393)


    Taxes:$4,716

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 132 DUVAL RD, WINTER HAVEN, FL 33884

    $309,50023 Days on yellowkey   MLS ID: O6412582

    REDUCED by $5,500 (1.7%) on 06/20/2026

    For Sale O6412582 - 132 DUVAL RD, WINTER HAVEN, FL 33884 38 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1260
       Built: 1975   Tax: $3,491 (2025)
    Community: Eloise Woods East Lake Mariam Unit
    Single Family


    Estimated Monthly Payment: $1,987 (change assumption)
    Mortgage ($1,696) + Taxes in 2025 ($291)


    Taxes:$3,491

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 1966 WHITE HAWK WAY, WINTER HAVEN, FL 33881

    $315,0005 Days on yellowkey   MLS ID: TB8521417

    For Sale TB8521417 - 1966 WHITE HAWK WAY, WINTER HAVEN, FL 33881 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1862
       Built: 2007
    Monthly Fee: $50
       Tax: $1,555 (2025)
    Community: Buckeye Trace
    Single Family


    Estimated Monthly Payment: $1,906 (change assumption)
    Mortgage ($1,726) + Fees ($50) + Taxes in 2025 ($130)


    Taxes:$1,555

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 814 SUN BURST RD, WINTER HAVEN, FL 33880

    $329,00098 Days on yellowkey   MLS ID: S5145959

    5 Days Off yellowkey (back on 4/13/2026)

    For Sale S5145959 - 814 SUN BURST RD, WINTER HAVEN, FL 33880 49 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2616
       Built: 2023
    Monthly Fee: $47
       Tax: $6,036 (2025)
    Community: Squires Grove Ph 2
    Single Family


    Estimated Monthly Payment: $2,353 (change assumption)
    Mortgage ($1,803) + Fees ($47) + Taxes in 2025 ($503)


    Taxes:$6,036

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4519 RAPALLO AVE, WINTER HAVEN, FL 33884

    $339,90026 Days on yellowkey   MLS ID: P4938826

    For Sale P4938826 - 4519 RAPALLO AVE, WINTER HAVEN, FL 33884 46 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2074
       Built: 2025
    Monthly Fee: $18
       Tax: $2,401 (2025)
    Community: Villamar Ph 6 & Ph 6D
    Single Family


    Estimated Monthly Payment: $2,081 (change assumption)
    Mortgage ($1,862) + Fees ($18) + Taxes in 2025 ($200)


    Taxes:$2,401

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1355 BENEVENTO DR, WINTER HAVEN, FL 33884

    $319,9008 Days on yellowkey   MLS ID: P4939067

    For Sale P4939067 - 1355 BENEVENTO DR, WINTER HAVEN, FL 33884 41 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1964
       Built: 2020
    Monthly Fee: $15
       Tax: $5,895 (2025)
    Community: Villamar Ph 2
    Single Family


    Estimated Monthly Payment: $2,259 (change assumption)
    Mortgage ($1,753) + Fees ($15) + Taxes in 2025 ($491)


    Taxes:$5,895

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1802 WHITE ELEPHANT LOOP, WINTER HAVEN, FL 33884

    $344,900459 Days on yellowkey   MLS ID: TB8364884

    For Sale TB8364884 - 1802 WHITE ELEPHANT LOOP, WINTER HAVEN, FL 33884 20 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1863
       Built: 2025
    Monthly Fee: $95

    Community: Peach Crossings
    Single Family


    Estimated Monthly Payment: $1,985 (change assumption)
    Mortgage ($1,890) + Fees ($95) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Denison Middle


  • 1629 NANTUCKET WAY, WINTER HAVEN, FL 33884

    $303,90091 Days on yellowkey   MLS ID: TB8490344

    For Sale TB8490344 - 1629 NANTUCKET WAY, WINTER HAVEN, FL 33884 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1526
       Built: 2025
    Monthly Fee: $95

    Community: Peach Crossings
    Single Family


    Estimated Monthly Payment: $1,760 (change assumption)
    Mortgage ($1,665) + Fees ($95) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Denison Middle


  • 3905 OSPREY POINTE CIR, WINTER HAVEN, FL 33884

    $304,00091 Days on yellowkey   MLS ID: P4938216

    REDUCED by $2,500 (0.8%) on 06/19/2026

    For Sale P4938216 - 3905 OSPREY POINTE CIR, WINTER HAVEN, FL 33884 53 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1729
       Built: 2005
    Monthly Fee: $210
       Tax: $3,251 (2025)
    Community: Osprey Pointe
    Single Family


    Estimated Monthly Payment: $2,147 (change assumption)
    Mortgage ($1,666) + Fees ($210) + Taxes in 2025 ($271)


    Taxes:$3,251

    Elementary School: Garden Grove Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 4121 GIORGIO DR, WINTER HAVEN, FL 33884

    $329,990131 Days on yellowkey   MLS ID: O6382578

    4 Days Off yellowkey (back on 5/8/2026)

    For Sale O6382578 - 4121 GIORGIO DR, WINTER HAVEN, FL 33884 34 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2447
       Built: 2026
    Monthly Fee: $18
       Tax: $3,035 (2025)
    Community: Villamar Phase 6 And Phase 6D
    Single Family


    Estimated Monthly Payment: $2,079 (change assumption)
    Mortgage ($1,808) + Fees ($18) + Taxes in 2025 ($253)


    Taxes:$3,035

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: McLaughlin Academy Of Excellence


  • 3155 COUNTRY CLUB CIR, WINTER HAVEN, FL 33881

    $310,00043 Days on yellowkey   MLS ID: S5149714

    REDUCED by $20,000 (6.1%) on 06/18/2026

    For Sale S5149714 - 3155 COUNTRY CLUB CIR, WINTER HAVEN, FL 33881 19 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1851
       Built: 2020
    Monthly Fee: $30
       Tax: $3,236 (2025)
    Community: Country Walk/Winter Haven
    Single Family


    Estimated Monthly Payment: $1,998 (change assumption)
    Mortgage ($1,699) + Fees ($30) + Taxes in 2025 ($270)


    Taxes:$3,236

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 271 INMAN BLVD, WINTER HAVEN, FL 33881

    $340,000201 Days on yellowkey   MLS ID: W7881213

    REDUCED by $10,000 (2.9%) on 06/18/2026

    For Sale W7881213 - 271 INMAN BLVD, WINTER HAVEN, FL 33881 41 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2274
       Built: 2024
    Monthly Fee: $49
       Tax: $1,347 (2024)
    Community: Inman Groves
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,024 (change assumption)
    Mortgage ($1,863) + Fees ($49) + Taxes in 2024 ($112)


    Taxes:$1,347

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Denison Middle


  • 339 LAKE SMART CIRCLE, WINTER HAVEN, FL 33881

    $333,00049 Days on yellowkey   MLS ID: S5149280

    REDUCED by $5,000 (1.5%) on 06/18/2026

    For Sale S5149280 - 339 LAKE SMART CIRCLE, WINTER HAVEN, FL 33881 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2173
       Built: 2021
    Monthly Fee: $50
       Tax: $3,879 (2025)
    Community: Lake Smart Pointe
    Single Family


    Estimated Monthly Payment: $2,198 (change assumption)
    Mortgage ($1,825) + Fees ($50) + Taxes in 2025 ($323)


    Taxes:$3,879

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4717 MAGNOLIA PRESERVE AVE, WINTER HAVEN, FL 33880

    $300,00068 Days on yellowkey   MLS ID: L4961135

    REDUCED by $4,900 (1.6%) on 06/18/2026

    For Sale L4961135 - 4717 MAGNOLIA PRESERVE AVE, WINTER HAVEN, FL 33880 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1874
       Built: 2016
    Monthly Fee: $32
       Tax: $3,902 (2025)
    Community: Magnolia Preserve Ph 2
    Single Family


    Estimated Monthly Payment: $2,001 (change assumption)
    Mortgage ($1,644) + Fees ($32) + Taxes in 2025 ($325)


    Taxes:$3,902

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4577 BACK NINE DR, WINTER HAVEN, FL 33884

    $349,600170 Days on yellowkey   MLS ID: P4937386

    For Sale P4937386 - 4577 BACK NINE DR, WINTER HAVEN, FL 33884 71 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1918
       Built: 2009
    Monthly Fee: $5
       Tax: $5,155 (2025)
    Community: Lake Ashton West Ph 01
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,350 (change assumption)
    Mortgage ($1,916) + Fees ($5) + Taxes in 2025 ($430)


    Taxes:$5,155

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None






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.