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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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  • 4519 RAPALLO AVE, WINTER HAVEN, FL 33884

    $339,90028 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


  • 390 16TH ST NE, WINTER HAVEN, FL 33881

    $238,900128 Days on yellowkey   MLS ID: P4937879

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

    REDUCED by $1,000 (0.4%) on 04/07/2026

    For Sale P4937879 - 390 16TH ST NE, WINTER HAVEN, FL 33881 25 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2178
       Built: 1959   Tax: $3,631 (2025)
    Community: Lake Elbert Heights Unit 02 02 Rep
    Single Family


    Estimated Monthly Payment: $1,612 (change assumption)
    Mortgage ($1,309) + Taxes in 2025 ($303)


    Taxes:$3,631

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 23 OAKWOOD RD, WINTER HAVEN, FL 33880

    $574,90056 Days on yellowkey   MLS ID: L4961490

    For Sale L4961490 - 23 OAKWOOD RD, WINTER HAVEN, FL 33880 65 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


  • 302 STERLING DR, WINTER HAVEN, FL 33884

    $365,0002 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


  • 6457 DOMIZIO DR, WINTER HAVEN, FL 33884

    $309,49099 Days on yellowkey   MLS ID: O6392165

    2 Days Off yellowkey (back on 6/24/2026)

    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: $53
       Tax: $32 (2024)
    Community: Villa Mar 40'S
    Single Family


    Estimated Monthly Payment: $1,751 (change assumption)
    Mortgage ($1,696) + Fees ($53) + Taxes in 2024 ($3)


    Taxes:$32

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Denison Middle


  • 2323 BRASSIE CT, WINTER HAVEN, FL 33884

    $313,967254 Days on yellowkey   MLS ID: L4956626

    2 Days Off yellowkey (back on 5/21/2026)

    REDUCED by $5,000 (1.6%) on 05/01/2026

    For Sale L4956626 - 2323 BRASSIE CT, WINTER HAVEN, FL 33884 4 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2405
       Built: 2025
    Monthly Fee: $68
       Tax: $7,100 (2025)
    Community: Villa Mar Phase 3
    Single Family


    Estimated Monthly Payment: $2,380 (change assumption)
    Mortgage ($1,720) + Fees ($68) + Taxes in 2025 ($592)


    Taxes:$7,100

    Elementary School: Chain O Lakes Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Berkley Accelerated Middle


  • 1525 LEAMINGTON LN, WINTER HAVEN, FL 33884

    $299,366392 Days on yellowkey   MLS ID: L4952865

    1 Days Off yellowkey (back on 5/21/2026)

    REDUCED by $5,000 (1.6%) on 05/01/2026

    For Sale L4952865 - 1525 LEAMINGTON LN, WINTER HAVEN, FL 33884 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2200
       Built: 2025
    Monthly Fee: $67
       Tax: $7,400 (2025)
    Community: Villa Mar Phase 3
    Single Family


    Estimated Monthly Payment: $2,324 (change assumption)
    Mortgage ($1,640) + Fees ($67) + Taxes in 2025 ($617)


    Taxes:$7,400

    Elementary School: Chain O Lakes Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Berkley Accelerated Middle


  • 1871 EMILY DR, WINTER HAVEN, FL 33884

    $312,50045 Days on yellowkey   MLS ID: S5149517

    For Sale S5149517 - 1871 EMILY DR, WINTER HAVEN, FL 33884 66 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2012
       Built: 2005
    Monthly Fee: $38
       Tax: $3,862 (2025)
    Community: Emily Estates
    Single Family


    Estimated Monthly Payment: $2,072 (change assumption)
    Mortgage ($1,712) + Fees ($38) + Taxes in 2025 ($322)


    Taxes:$3,862

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 6224 BOTTICELLA BLVD, WINTER HAVEN, FL 33884

    $289,4909 Days on yellowkey   MLS ID: O6417853

    1 Days Off yellowkey (back on 6/24/2026)

    REDUCED by $5,000 (1.7%) on 06/19/2026

    For Sale O6417853 - 6224 BOTTICELLA BLVD, WINTER HAVEN, FL 33884 15 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2112
       Built: 2026
    Monthly Fee: $53
       Tax: $32 (2025)
    Community: Villa Mar 40'S
    Single Family


    Estimated Monthly Payment: $1,642 (change assumption)
    Mortgage ($1,586) + Fees ($53) + Taxes in 2025 ($3)


    Taxes:$32

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 58 LAKE LINK CIR SE, WINTER HAVEN, FL 33884

    $398,50049 Days on yellowkey   MLS ID: P4938677

    0 Days Off yellowkey (back on 5/15/2026)

    For Sale P4938677 - 58 LAKE LINK CIR SE, WINTER HAVEN, FL 33884 42 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2000
       Built: 1971   Tax: $5,997 (2025)
    Community: Lake Link Estates
    Single Family


    Estimated Monthly Payment: $2,683 (change assumption)
    Mortgage ($2,184) + Taxes in 2025 ($500)


    Taxes:$5,997

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5268 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884

    $579,90079 Days on yellowkey   MLS ID: L4960893

    For Sale L4960893 - 5268 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884 75 photos

    Bed: 3   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2354
       Built: 2007
    Monthly Fee: $5
       Tax: $4,690 (2025)
    Community: Lake Ashton West Ph 01
    Single Family


    Estimated Monthly Payment: $3,573 (change assumption)
    Mortgage ($3,177) + Fees ($5) + Taxes in 2025 ($391)


    Taxes:$4,690

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 516 REGGIE RD, WINTER HAVEN, FL 33884

    $325,0003 Days on yellowkey   MLS ID: O6418177

    For Sale O6418177 - 516 REGGIE RD, WINTER HAVEN, FL 33884 56 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2109
       Built: 2024
    Monthly Fee: $16
       Tax: $7,811 (2025)
    Community: Peace Crk Reserve
    Single Family


    Estimated Monthly Payment: $2,448 (change assumption)
    Mortgage ($1,781) + Fees ($16) + Taxes in 2025 ($651)


    Taxes:$7,811

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood Middle


  • 1138 MICHELANGELO LN, WINTER HAVEN, FL 33884

    $394,90077 Days on yellowkey   MLS ID: S5147440

    0 Days Off yellowkey (back on 6/23/2026)

    REDUCED by $5,000 (1.3%) on 05/29/2026

    For Sale S5147440 - 1138 MICHELANGELO LN, WINTER HAVEN, FL 33884 72 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2386
       Built: 2023
    Monthly Fee: $55
       Tax: $4,275 (2025)
    Community: Estates/Lk Florence
    Single Family


    Estimated Monthly Payment: $2,575 (change assumption)
    Mortgage ($2,164) + Fees ($55) + Taxes in 2025 ($356)


    Taxes:$4,275

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6337 BOTTICELLA BLVD, WINTER HAVEN, FL 33884

    $295,99069 Days on yellowkey   MLS ID: W7884986

    11 Days Off yellowkey (back on 6/23/2026)

    For Sale W7884986 - 6337 BOTTICELLA BLVD, WINTER HAVEN, FL 33884 16 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2370
       Built: 2026
    Monthly Fee: $19

    Community: Villa Mar
    Single Family


    Estimated Monthly Payment: $1,641 (change assumption)
    Mortgage ($1,622) + Fees ($19) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 23 CASARENA CT, WINTER HAVEN, FL 33881

    $219,90064 Days on yellowkey   MLS ID: S5148554

    REDUCED by $10,100 (4.4%) on 06/19/2026

    For Sale S5148554 - 23 CASARENA CT, WINTER HAVEN, FL 33881 50 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2045
       Built: 1984
    Monthly Fee: $310
       Tax: $3,909 (2025)
    Community: Casarena/Lks
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,841 (change assumption)
    Mortgage ($1,205) + Fees ($310) + Taxes in 2025 ($326)


    Taxes:$3,909

    Elementary School: Inwood Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Westwood Middle


  • 3614 PLYMOUTH DR, WINTER HAVEN, FL 33884

    $320,0004 Days on yellowkey   MLS ID: TB8522011

    For Sale TB8522011 - 3614 PLYMOUTH DR, WINTER HAVEN, FL 33884 57 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2109
       Built: 2006
    Monthly Fee: $504
       Tax: $2,165 (2025)
    Community: Traditions Ph 01
    Single Family


    Estimated Monthly Payment: $2,438 (change assumption)
    Mortgage ($1,753) + Fees ($504) + Taxes in 2025 ($180)


    Taxes:$2,165

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: None


  • 2820 SAM MARCY WAY E, WINTER HAVEN, FL 33884

    $351,3704 Days on yellowkey   MLS ID: L4962977

    0 Days Off yellowkey (back on 6/22/2026)

    For Sale L4962977 - 2820 SAM MARCY WAY E, WINTER HAVEN, FL 33884 5 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2227
       Built: 2026
    Monthly Fee: $18

    Community: Villamar
    Single Family


    Estimated Monthly Payment: $1,943 (change assumption)
    Mortgage ($1,925) + Fees ($18) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2112 RIVER HAWK LOOP, WINTER HAVEN, FL 33880

    $429,90057 Days on yellowkey   MLS ID: S5148856

    For Sale S5148856 - 2112 RIVER HAWK LOOP, WINTER HAVEN, FL 33880 39 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


  • 2108 RIVER HAWK LOOP, WINTER HAVEN, FL 33880

    $384,90057 Days on yellowkey   MLS ID: S5148855

    For Sale S5148855 - 2108 RIVER HAWK LOOP, WINTER HAVEN, FL 33880 24 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


  • 2008 RIVER HAWK LOOP, WINTER HAVEN, FL 33880

    $385,00062 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






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.