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Displaying: For Sale

Location: Winter Haven

Property Type(s): Single Family

Living Area Square Feet: 2000 to 2499

Winter Haven - 177 properties found

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  • 312 TOWHEE RD, WINTER HAVEN, FL 33881

    $339,000153 Days on yellowkey   MLS ID: B4902119

    REDUCED by $10,000 (2.9%) on 04/27/2026

    For Sale B4902119 - 312 TOWHEE RD, WINTER HAVEN, FL 33881 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2020
       Built: 2005
    Monthly Fee: $34
       Tax: $2,621 (2024)
    Community: Hamilton West Ph 01
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,110 (change assumption)
    Mortgage ($1,857) + Fees ($34) + Taxes in 2024 ($218)


    Taxes:$2,621

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Denison Middle


  • 5456 SAN PIETRO DR, WINTER HAVEN, FL 33884

    $359,9991 Day on yellowkey   MLS ID: TB8504505

    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: $2,416 (change assumption)
    Mortgage ($1,973) + 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


  • 5464 SAN PIETRO DR, WINTER HAVEN, FL 33884

    $369,9991 Day on yellowkey   MLS ID: TB8504144

    For Sale TB8504144 - 5464 SAN PIETRO DR, WINTER HAVEN, FL 33884 16 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2470
       Built: 2026
    Monthly Fee: $53
       Tax: $4,690 (2025)
    Community: Villa Mar
    Single Family


    Estimated Monthly Payment: $2,471 (change assumption)
    Mortgage ($2,027) + 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


  • 1290 N LAKE SHIPP DR N, WINTER HAVEN, FL 33880

    $795,00017 Days on yellowkey   MLS ID: L4961193

    For Sale L4961193 - 1290 N LAKE SHIPP DR N, WINTER HAVEN, FL 33880 47 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2001
       Built: 2021   Tax: $7,094 (2025)
    Community: N/A
    Single Family


    Estimated Monthly Payment: $4,947 (change assumption)
    Mortgage ($4,356) + Taxes in 2025 ($591)


    Taxes:$7,094

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6457 DOMIZIO DR, WINTER HAVEN, FL 33884

    $309,49046 Days on yellowkey   MLS ID: O6392165

    INCREASED by $500 (0.2%) on 04/07/2026

    For Sale O6392165 - 6457 DOMIZIO DR, WINTER HAVEN, FL 33884 31 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2326
       Built: 2025
    Monthly Fee: $320
       Tax: $32 (2024)
    Community: Villa Mar 40'S
    Single Family


    Estimated Monthly Payment: $2,018 (change assumption)
    Mortgage ($1,696) + Fees ($320) + Taxes in 2024 ($3)


    Taxes:$32

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Denison Middle


  • 271 INMAN BLVD, WINTER HAVEN, FL 33881

    $350,000150 Days on yellowkey   MLS ID: W7881213

    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: $2,079 (change assumption)
    Mortgage ($1,918) + 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


  • 731 CANBERRA RD, WINTER HAVEN, FL 33884

    $325,000164 Days on yellowkey   MLS ID: L4957294

    REDUCED by $10,000 (3.0%) on 04/25/2026

    For Sale L4957294 - 731 CANBERRA RD, WINTER HAVEN, FL 33884 51 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2140
       Built: 1989
    Monthly Fee: $17
       Tax: $2,207 (2024)
    Community: Cypresswood Patio Homes
    Single Family


    Estimated Monthly Payment: $1,982 (change assumption)
    Mortgage ($1,781) + Fees ($17) + Taxes in 2024 ($184)


    Taxes:$2,207

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2108 RIVER HAWK LOOP, WINTER HAVEN, FL 33880

    $384,9004 Days on yellowkey   MLS ID: S5148855

    For Sale S5148855 - 2108 RIVER HAWK LOOP, WINTER HAVEN, FL 33880 1 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2032
       Built: 2026
    Monthly Fee: $98
       Tax: $228 (2025)
    Community: Residences At Winter Haven
    Single Family


    Estimated Monthly Payment: $2,226 (change assumption)
    Mortgage ($2,109) + 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


  • 2112 RIVER HAWK LOOP, WINTER HAVEN, FL 33880

    $429,9004 Days on yellowkey   MLS ID: S5148856

    For Sale S5148856 - 2112 RIVER HAWK LOOP, WINTER HAVEN, FL 33880 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2378
       Built: 2026
    Monthly Fee: $98
       Tax: $228 (2025)
    Community: Residences Of Winter Haven
    Single Family


    Estimated Monthly Payment: $2,473 (change assumption)
    Mortgage ($2,356) + 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


  • 2008 RIVER HAWK LOOP, WINTER HAVEN, FL 33880

    $385,0009 Days on yellowkey   MLS ID: S5148468

    For Sale S5148468 - 2008 RIVER HAWK LOOP, WINTER HAVEN, FL 33880 37 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2032
       Built: 2026
    Monthly Fee: $98
       Tax: $228 (2025)
    Community: Residences At Winter Haven
    Single Family


    Estimated Monthly Payment: $2,227 (change assumption)
    Mortgage ($2,110) + 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


  • 2 CASARENA CT, WINTER HAVEN, FL 33881

    $320,00097 Days on yellowkey   MLS ID: L4958770

    For Sale L4958770 - 2 CASARENA CT, WINTER HAVEN, FL 33881 44 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2377
       Built: 1983
    Monthly Fee: $310
       Tax: $5,755 (2025)
    Community: Casarena On Lakes
    Single Family


    Estimated Monthly Payment: $2,543 (change assumption)
    Mortgage ($1,753) + Fees ($310) + Taxes in 2025 ($480)


    Taxes:$5,755

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 104 SANDERLING DR, WINTER HAVEN, FL 33881

    $419,00041 Days on yellowkey   MLS ID: O6392989

    REDUCED by $6,000 (1.4%) on 05/02/2026

    For Sale O6392989 - 104 SANDERLING DR, WINTER HAVEN, FL 33881 38 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2277
       Built: 2004
    Monthly Fee: $34
       Tax: $6,245 (2025)
    Community: Hamilton West Ph 01
    Single Family


    Estimated Monthly Payment: $2,850 (change assumption)
    Mortgage ($2,296) + Fees ($34) + Taxes in 2025 ($520)


    Taxes:$6,245

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 353 MANDOLIN LN, WINTER HAVEN, FL 33884

    $379,00018 Days on yellowkey   MLS ID: L4961166

    For Sale L4961166 - 353 MANDOLIN LN, WINTER HAVEN, FL 33884 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2035
       Built: 2010
    Monthly Fee: $46
       Tax: $2,370 (2025)
    Community: Mandolin
    Single Family


    Estimated Monthly Payment: $2,320 (change assumption)
    Mortgage ($2,077) + Fees ($46) + Taxes in 2025 ($198)


    Taxes:$2,370

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 5460 SAN PIETRO DR, WINTER HAVEN, FL 33884

    $339,9993 Days on yellowkey   MLS ID: TB8504154

    For Sale TB8504154 - 5460 SAN PIETRO DR, WINTER HAVEN, FL 33884 22 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2038
       Built: 2026
    Monthly Fee: $53
       Tax: $4,690 (2025)
    Community: Villa Mar
    Single Family


    Estimated Monthly Payment: $2,307 (change assumption)
    Mortgage ($1,863) + 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


  • 3322 OAK HILL PL, WINTER HAVEN, FL 33884

    $349,0003 Days on yellowkey   MLS ID: O6404080

    For Sale O6404080 - 3322 OAK HILL PL, WINTER HAVEN, FL 33884 37 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2109
       Built: 2006
    Monthly Fee: $155

    Community: Oakgrove Sub
    Single Family


    Estimated Monthly Payment: $2,067 (change assumption)
    Mortgage ($1,912) + Fees ($155) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4263 STAFFORD DR, WINTER HAVEN, FL 33880

    $380,0003 Days on yellowkey   MLS ID: O6404043

    For Sale O6404043 - 4263 STAFFORD DR, WINTER HAVEN, FL 33880 63 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2234
       Built: 1986   Tax: $1,977 (2025)
    Community: Lake Thomas Woods Add 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,247 (change assumption)
    Mortgage ($2,082) + Taxes in 2025 ($165)


    Taxes:$1,977

    Elementary School: Clarence Boswell Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood Middle


  • 23 OAKWOOD RD, WINTER HAVEN, FL 33880

    $574,9003 Days on yellowkey   MLS ID: L4961490

    For Sale L4961490 - 23 OAKWOOD RD, WINTER HAVEN, FL 33880 54 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2125
       Built: 1994   Tax: $5,836 (2025)
    Community: N/A
    Single Family


    Estimated Monthly Payment: $3,636 (change assumption)
    Mortgage ($3,150) + Taxes in 2025 ($486)


    Taxes:$5,836

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 100 ALACHUA DR, WINTER HAVEN, FL 33884

    $575,0003 Days on yellowkey   MLS ID: B4902232

    For Sale B4902232 - 100 ALACHUA DR, WINTER HAVEN, FL 33884 63 photos

    Bed: 3   Bath: 1.5
    Liv Area Sq Ft: 2002
       Built: 1963   Tax: $3,744 (2025)
    Community: Eloise Woods Lake Mariam Unit
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,463 (change assumption)
    Mortgage ($3,151) + Taxes in 2025 ($312)


    Taxes:$3,744

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 144 BEVERLY DR, WINTER HAVEN, FL 33884

    $409,90024 Days on yellowkey   MLS ID: O6397768

    REDUCED by $10,100 (2.4%) on 04/28/2026

    For Sale O6397768 - 144 BEVERLY DR, WINTER HAVEN, FL 33884 63 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: $2,561 (change assumption)
    Mortgage ($2,246) + Taxes in 2025 ($315)


    Taxes:$3,785

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2968 PLANTATION RD, WINTER HAVEN, FL 33884

    $442,00045 Days on yellowkey   MLS ID: P4938120

    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






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.