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Displaying: For Sale

Location: Winter Haven

Property Type(s): Single Family

Price: $300,000 to $399,000

Winter Haven - 286 properties found

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  • 3905 OSPREY POINTE CIR, WINTER HAVEN, FL 33884

    $304,00093 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

    $329,990133 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

    $310,00045 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

    $340,000203 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

    $333,00051 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


  • 4577 BACK NINE DR, WINTER HAVEN, FL 33884

    $349,600172 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


  • 0 38TH ST NW, WINTER HAVEN, FL 33881

    $350,0009 Days on yellowkey   MLS ID: TB8520450

    For Sale TB8520450 - 0 38TH ST NW, WINTER HAVEN, FL 33881 8 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1322
       Built: 2026   Tax: $356 (2025)
    Community: 38Th Street Subdivision
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,947 (change assumption)
    Mortgage ($1,918) + Taxes in 2025 ($30)


    Taxes:$356

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 0 38TH ST NW, WINTER HAVEN, FL 33881

    $350,0009 Days on yellowkey   MLS ID: TB8520435

    For Sale TB8520435 - 0 38TH ST NW, WINTER HAVEN, FL 33881 8 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1322
       Built: 2026   Tax: $356 (2025)
    Community: 38Th Street Subdivision
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,947 (change assumption)
    Mortgage ($1,918) + Taxes in 2025 ($30)


    Taxes:$356

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 0 38TH ST NW, WINTER HAVEN, FL 33881

    $350,0009 Days on yellowkey   MLS ID: TB8520422

    For Sale TB8520422 - 0 38TH ST NW, WINTER HAVEN, FL 33881 8 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1322
       Built: 2026   Tax: $356 (2025)
    Community: 38Th Street Subdivision
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,947 (change assumption)
    Mortgage ($1,918) + Taxes in 2025 ($30)


    Taxes:$356

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 0 38TH ST NW, WINTER HAVEN, FL 33881

    $350,0009 Days on yellowkey   MLS ID: TB8520402

    For Sale TB8520402 - 0 38TH ST NW, WINTER HAVEN, FL 33881 10 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1327
       Built: 2026   Tax: $356 (2025)
    Community: 38Th Street Subdivision
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,947 (change assumption)
    Mortgage ($1,918) + Taxes in 2025 ($30)


    Taxes:$356

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3932 GIORGIO DR, WINTER HAVEN, FL 33884

    $319,1909 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

    $340,0009 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


  • 1819 SANDHILL LN, WINTER HAVEN, FL 33884

    $354,00010 Days on yellowkey   MLS ID: K4903563

    For Sale K4903563 - 1819 SANDHILL LN, WINTER HAVEN, FL 33884 80 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2045
       Built: 2002
    Monthly Fee: $149
       Tax: $3,960 (2025)
    Community: Sand Hill Lane
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,419 (change assumption)
    Mortgage ($1,940) + Fees ($149) + Taxes in 2025 ($330)


    Taxes:$3,960

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1782 WHITE ELEPHANT, WINTER HAVEN, FL 33884

    $342,90050 Days on yellowkey   MLS ID: O6405643

    INCREASED by $4,000 (1.2%) on 05/18/2026

    For Sale O6405643 - 1782 WHITE ELEPHANT, WINTER HAVEN, FL 33884 34 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1863
       Built: 2025
    Monthly Fee: $95
       Tax: $760 (2025)
    Community: Peach Crossings
    Single Family


    Estimated Monthly Payment: $2,037 (change assumption)
    Mortgage ($1,879) + Fees ($95) + Taxes in 2025 ($63)


    Taxes:$760

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 811 ANDREW ST, WINTER HAVEN, FL 33881

    $319,99031 Days on yellowkey   MLS ID: O6410787

    REDUCED by $2,500 (0.8%) on 06/17/2026

    For Sale O6410787 - 811 ANDREW ST, WINTER HAVEN, FL 33881 2 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1600
       Built: 2026
    Monthly Fee: $6
       Tax: $2,695 (2025)
    Community: Willowbrook North
    Single Family


    Estimated Monthly Payment: $1,984 (change assumption)
    Mortgage ($1,753) + Fees ($6) + Taxes in 2025 ($225)


    Taxes:$2,695

    Elementary School: Fred G. Garnier Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 1396 AXEL CIR, WINTER HAVEN, FL 33880

    $389,90028 Days on yellowkey   MLS ID: TB8512920

    REDUCED by $10,100 (2.5%) on 06/10/2026

    For Sale TB8512920 - 1396 AXEL CIR, WINTER HAVEN, FL 33880 34 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3022
       Built: 2022
    Monthly Fee: $71
       Tax: $4,961 (2025)
    Community: Pinnacle Point
    Single Family


    Estimated Monthly Payment: $2,621 (change assumption)
    Mortgage ($2,136) + Fees ($71) + Taxes in 2025 ($413)


    Taxes:$4,961

    Elementary School: Lake Shipp Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Westwood Middle


  • 116 MANDOLIN DR, WINTER HAVEN, FL 33884

    $365,00058 Days on yellowkey   MLS ID: O6403313

    REDUCED by $5,000 (1.4%) on 05/18/2026

    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: $2,529 (change assumption)
    Mortgage ($2,000) + 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


  • 131 RUBY LAKE DR, WINTER HAVEN, FL 33884

    $369,00079 Days on yellowkey   MLS ID: P4938379

    REDUCED by $6,000 (1.6%) on 06/17/2026

    For Sale P4938379 - 131 RUBY LAKE DR, WINTER HAVEN, FL 33884 62 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1914
       Built: 2000
    Monthly Fee: $71
       Tax: $4,453 (2025)
    Community: Ruby Lake Ph 01
    Single Family


    Estimated Monthly Payment: $2,464 (change assumption)
    Mortgage ($2,022) + Fees ($71) + Taxes in 2025 ($371)


    Taxes:$4,453

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 2122 RIVER HAWK LOOP, WINTER HAVEN, FL 33880

    $344,90039 Days on yellowkey   MLS ID: S5149889

    For Sale S5149889 - 2122 RIVER HAWK LOOP, WINTER HAVEN, FL 33880 1 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1741
       Built: 2026
    Monthly Fee: $98
       Tax: $228 (2025)
    Community: Residences/Winter Haven
    Single Family


    Estimated Monthly Payment: $2,007 (change assumption)
    Mortgage ($1,890) + Fees ($98) + Taxes in 2025 ($19)


    Taxes:$228

    Elementary School: Lake Shipp Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood Middle


  • 2121 RIVER HAWK LOOP, WINTER HAVEN, FL 33880

    $342,90036 Days on yellowkey   MLS ID: S5149725

    For Sale S5149725 - 2121 RIVER HAWK LOOP, WINTER HAVEN, FL 33880 1 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1741
       Built: 2026
    Monthly Fee: $98
       Tax: $228 (2025)
    Community: Residences At Winter Haven
    Single Family


    Estimated Monthly Payment: $1,996 (change assumption)
    Mortgage ($1,879) + Fees ($98) + Taxes in 2025 ($19)


    Taxes:$228

    Elementary School: Lake Shipp Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood Middle






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.