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Displaying: For Sale

Location: Winter Haven

Property Type(s): Single Family

Living Area Square Feet: 1500 to 1999

Winter Haven - 311 properties found

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  • 430 HILLCREST DR SE, WINTER HAVEN, FL 33884

    $299,90038 Days on yellowkey   MLS ID: L4961985

    REDUCED by $9,100 (2.9%) on 06/19/2026

    For Sale L4961985 - 430 HILLCREST DR SE, WINTER HAVEN, FL 33884 42 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1594
       Built: 1979   Tax: $2,020 (2025)
    Community: Eloise Woods Lake Roy Unit
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $1,812 (change assumption)
    Mortgage ($1,643) + Taxes in 2025 ($168)


    Taxes:$2,020

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3905 OSPREY POINTE CIR, WINTER HAVEN, FL 33884

    $304,00092 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


  • WINTER HAVEN, FL 33881

    $245,0007 Days on yellowkey   MLS ID: P4939088

    For Sale P4939088 - WINTER HAVEN, FL 33881 27 photos

    Bed: 3   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 1700
       Built: 1925   Tax: $2,964 (2025)
    Community: Lake Elbert Heights
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,589 (change assumption)
    Mortgage ($1,342) + Taxes in 2025 ($247)


    Taxes:$2,964

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1199 SOPHIA BLVD, WINTER HAVEN, FL 33881

    $279,9007 Days on yellowkey   MLS ID: S5151706

    For Sale S5151706 - 1199 SOPHIA BLVD, WINTER HAVEN, FL 33881 3 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1690
       Built: 2019
    Monthly Fee: $25
       Tax: $2,791 (2025)
    Community: Buckeye Rdg
    Single Family


    Estimated Monthly Payment: $1,791 (change assumption)
    Mortgage ($1,534) + Fees ($25) + Taxes in 2025 ($233)


    Taxes:$2,791

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 1740 2ND ST NE, WINTER HAVEN, FL 33881

    $230,000255 Days on yellowkey   MLS ID: L4956531

    REDUCED by $5,000 (2.1%) on 06/18/2026

    For Sale L4956531 - 1740 2ND ST NE, WINTER HAVEN, FL 33881 7 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1683
       Built: 2025   Tax: $308 (2024)
    Community: Maud Meadows
    Single Family


    Estimated Monthly Payment: $1,286 (change assumption)
    Mortgage ($1,260) + Taxes in 2024 ($26)


    Taxes:$308

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3155 COUNTRY CLUB CIR, WINTER HAVEN, FL 33881

    $310,00044 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


  • 2700 IDYLRIDGE WAY, WINTER HAVEN, FL 33881

    $399,990106 Days on yellowkey   MLS ID: L4960012

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

    REDUCED by $15,010 (3.6%) on 04/17/2026

    For Sale L4960012 - 2700 IDYLRIDGE WAY, WINTER HAVEN, FL 33881 33 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1968
       Built: 1962   Tax: $1,813 (2025)
    Community: Idyl Ridge View
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,343 (change assumption)
    Mortgage ($2,192) + Taxes in 2025 ($151)


    Taxes:$1,813

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1533 MAJESTIC LN, WINTER HAVEN, FL 33880

    $250,000111 Days on yellowkey   MLS ID: L4960031

    REDUCED by $15,000 (5.7%) on 06/05/2026

    For Sale L4960031 - 1533 MAJESTIC LN, WINTER HAVEN, FL 33880 32 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1957
       Built: 2023
    Monthly Fee: $38
       Tax: $4,059 (2025)
    Community: Eagle Lndg Ph Ii
    Single Family


    Estimated Monthly Payment: $1,746 (change assumption)
    Mortgage ($1,370) + Fees ($38) + Taxes in 2025 ($338)


    Taxes:$4,059

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 4840 OLD LUCERNE PARK RD, WINTER HAVEN, FL 33881

    $425,00016 Days on yellowkey   MLS ID: P4938821

    For Sale P4938821 - 4840 OLD LUCERNE PARK RD, WINTER HAVEN, FL 33881 44 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1927
       Built: 1977   Tax: $2,170 (2025)
    Community: Lucerne Shores
    Single Family


    Estimated Monthly Payment: $2,510 (change assumption)
    Mortgage ($2,329) + Taxes in 2025 ($181)


    Taxes:$2,170

    Elementary School: Lake Alfred Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 4717 MAGNOLIA PRESERVE AVE, WINTER HAVEN, FL 33880

    $300,00069 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

    $349,600171 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


  • 352 ALEXZANDER WAY, WINTER HAVEN, FL 33881

    $270,90090 Days on yellowkey   MLS ID: L4960645

    1 Days Off yellowkey (back on 6/18/2026)

    INCREASED by $1,000 (0.4%) on 06/18/2026

    For Sale L4960645 - 352 ALEXZANDER WAY, WINTER HAVEN, FL 33881 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1867
       Built: 2021
    Monthly Fee: $86
       Tax: $4,088 (2024)
    Community: Jace Lndg
    Single Family


    Estimated Monthly Payment: $1,911 (change assumption)
    Mortgage ($1,484) + Fees ($86) + Taxes in 2024 ($341)


    Taxes:$4,088

    Elementary School: Walter Caldwell Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: None


  • 2415 BRASSIE CT, WINTER HAVEN, FL 33884

    $295,00072 Days on yellowkey   MLS ID: P4938435

    INCREASED by $6,000 (2.1%) on 06/18/2026

    For Sale P4938435 - 2415 BRASSIE CT, WINTER HAVEN, FL 33884 51 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1629
       Built: 2022
    Monthly Fee: $18
       Tax: $2,101 (2025)
    Community: Villamar Ph 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,809 (change assumption)
    Mortgage ($1,616) + Fees ($18) + Taxes in 2025 ($175)


    Taxes:$2,101

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 111 KRENSON BAY LOOP, WINTER HAVEN, FL 33881

    $284,999112 Days on yellowkey   MLS ID: S5145191

    REDUCED by $1 (0.0%) on 05/15/2026

    SHORT SALE S5145191 - 111 KRENSON BAY LOOP, WINTER HAVEN, FL 33881 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1543
       Built: 2023
    Monthly Fee: $83
       Tax: $3,628 (2025)
    Community: Krenson Bay
    Single Family


    Estimated Monthly Payment: $1,947 (change assumption)
    Mortgage ($1,562) + Fees ($83) + Taxes in 2025 ($302)


    Taxes:$3,628

    Elementary School: Frank E. Brigham Academy

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 6304 RED HERRING DR, WINTER HAVEN, FL 33881

    $235,00038 Days on yellowkey   MLS ID: S5149412

    0 Days Off yellowkey (back on 6/10/2026)

    REDUCED by $10,000 (4.1%) on 06/09/2026

    For Sale S5149412 - 6304 RED HERRING DR, WINTER HAVEN, FL 33881 40 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1592
       Built: 2016
    Monthly Fee: $15
       Tax: $3,864 (2025)
    Community: Lakeside Landings Ph 01
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,625 (change assumption)
    Mortgage ($1,288) + Fees ($15) + Taxes in 2025 ($322)


    Taxes:$3,864

    Elementary School: Fred G. Garnier Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 2018 MARILYN AVE, WINTER HAVEN, FL 33881

    $299,9008 Days on yellowkey   MLS ID: O6417950

    For Sale O6417950 - 2018 MARILYN AVE, WINTER HAVEN, FL 33881 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1651
       Built: 1968   Tax: $2,604 (2025)
    Community: Leisure Shores
    Single Family


    Estimated Monthly Payment: $1,860 (change assumption)
    Mortgage ($1,643) + Taxes in 2025 ($217)


    Taxes:$2,604

    Elementary School: Fred G. Garnier Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Westwood Middle


  • 3932 GIORGIO DR, WINTER HAVEN, FL 33884

    $319,1908 Days on yellowkey   MLS ID: TB8520161

    For Sale TB8520161 - 3932 GIORGIO DR, WINTER HAVEN, FL 33884 12 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1695
       Built: 2026
    Monthly Fee: $154
       Tax: $1 (2026)
    Community: Villamar
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,903 (change assumption)
    Mortgage ($1,749) + Fees ($154) + Taxes in 2026 ($0)


    Taxes:$1

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2026

    Middle School: Denison Middle


  • 937 CATTLEMAN ST, WINTER HAVEN, FL 33881

    $340,0008 Days on yellowkey   MLS ID: W7886749

    For Sale W7886749 - 937 CATTLEMAN ST, WINTER HAVEN, FL 33881 18 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1828
       Built: 2023
    Monthly Fee: $50
       Tax: $5,045 (2025)
    Community: Inman Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $2,333 (change assumption)
    Mortgage ($1,863) + Fees ($50) + Taxes in 2025 ($420)


    Taxes:$5,045

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 265 MAJESTIC GARDENS LN, WINTER HAVEN, FL 33880

    $299,99917 Days on yellowkey   MLS ID: L4962565

    REDUCED by $10,001 (3.2%) on 06/17/2026

    For Sale L4962565 - 265 MAJESTIC GARDENS LN, WINTER HAVEN, FL 33880 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1951
       Built: 2006
    Monthly Fee: $33
       Tax: $4,273 (2025)
    Community: Gardens Ph 01
    Single Family


    Estimated Monthly Payment: $2,033 (change assumption)
    Mortgage ($1,644) + Fees ($33) + Taxes in 2025 ($356)


    Taxes:$4,273

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 255 HAINES BLVD, WINTER HAVEN, FL 33881

    $294,99926 Days on yellowkey   MLS ID: B4902269

    REDUCED by $5,000 (1.7%) on 06/17/2026

    For Sale B4902269 - 255 HAINES BLVD, WINTER HAVEN, FL 33881 59 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1793
       Built: 2017
    Monthly Fee: $3
       Tax: $4,634 (2025)
    Community: Lakes At Lucerne Park Ph 02
    Single Family


    Estimated Monthly Payment: $2,006 (change assumption)
    Mortgage ($1,616) + Fees ($3) + Taxes in 2025 ($386)


    Taxes:$4,634

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None






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