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Displaying: For Sale

Location: Winter Haven

Property Type(s): Single Family

Price: $300,000 to $399,000

Winter Haven - 251 properties found

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  • 2638 SAN MARCO WAY, WINTER HAVEN, FL 33884

    $333,000259 Days on yellowkey   MLS ID: S5132867

    SHORT SALE S5132867 - 2638 SAN MARCO WAY, WINTER HAVEN, FL 33884 23 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1707
       Built: 2023
    Monthly Fee: $17
       Tax: $5,812 (2024)
    Community: Villamar Ph Four
    Single Family


    Estimated Monthly Payment: $2,326 (change assumption)
    Mortgage ($1,825) + Fees ($17) + Taxes in 2024 ($484)


    Taxes:$5,812

    Elementary School: Chain O Lakes Elem

    High School: None

    Tax Year: 2024

    Middle School: None


  • 260 GREENFIELD RD, WINTER HAVEN, FL 33884

    $370,00083 Days on yellowkey   MLS ID: P4937787

    REDUCED by $23,000 (5.9%) on 05/02/2026

    For Sale P4937787 - 260 GREENFIELD RD, WINTER HAVEN, FL 33884 52 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1947
       Built: 1978
    Monthly Fee: $152
       Tax: $5,885 (2025)
    Community: Cypresswood Greenfield Village
    Single Family


    Estimated Monthly Payment: $2,670 (change assumption)
    Mortgage ($2,027) + Fees ($152) + Taxes in 2025 ($490)


    Taxes:$5,885

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 740 SQUIRES GROVE DR, WINTER HAVEN, FL 33880

    $364,99072 Days on yellowkey   MLS ID: S5144206

    REDUCED by $5,000 (1.4%) on 05/02/2026

    For Sale S5144206 - 740 SQUIRES GROVE DR, WINTER HAVEN, FL 33880 35 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2616
       Built: 2022
    Monthly Fee: $64
       Tax: $5,142 (2025)
    Community: Squires Grove Ph 2
    Single Family


    Estimated Monthly Payment: $2,492 (change assumption)
    Mortgage ($2,000) + Fees ($64) + Taxes in 2025 ($429)


    Taxes:$5,142

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 265 LAKE THOMAS DR, WINTER HAVEN, FL 33880

    $348,95069 Days on yellowkey   MLS ID: L4959685

    REDUCED by $1,000 (0.3%) on 05/02/2026

    For Sale L4959685 - 265 LAKE THOMAS DR, WINTER HAVEN, FL 33880 41 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1517
       Built: 1985   Tax: $1,169 (2025)
    Community: Timber Wood
    Single Family


    Estimated Monthly Payment: $2,009 (change assumption)
    Mortgage ($1,912) + Taxes in 2025 ($97)


    Taxes:$1,169

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1640 NW PEARCE RD, WINTER HAVEN, FL 33881

    $330,000278 Days on yellowkey   MLS ID: L4954651

    REDUCED by $15,000 (4.3%) on 05/02/2026

    For Sale L4954651 - 1640 NW PEARCE RD, WINTER HAVEN, FL 33881 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1421
       Built: 2025
    Community: Lake View Sub Pb 3 Pg 80
    Single Family


    Estimated Monthly Payment: $1,808 (change assumption)
    Mortgage ($1,808) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2024

    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


  • 136 LAKE RING DR, WINTER HAVEN, FL 33884

    $324,9003 Days on yellowkey   MLS ID: P4938606

    For Sale P4938606 - 136 LAKE RING DR, WINTER HAVEN, FL 33884 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1728
       Built: 1975   Tax: $2,508 (2025)
    Community: Eloise Woods Lake Mariam Unit
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,989 (change assumption)
    Mortgage ($1,780) + Taxes in 2025 ($209)


    Taxes:$2,508

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1633 NANTUCKET WAY, WINTER HAVEN, FL 33884

    $338,9003 Days on yellowkey   MLS ID: O6403149

    For Sale O6403149 - 1633 NANTUCKET WAY, 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: $1,952 (change assumption)
    Mortgage ($1,857) + Fees ($95) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2024

    Middle School: Denison Middle


  • 2519 AVENUE E SW, WINTER HAVEN, FL 33880

    $309,000131 Days on yellowkey   MLS ID: TB8458652

    REDUCED by $3,000 (1.0%) on 04/25/2026

    For Sale TB8458652 - 2519 AVENUE E SW, WINTER HAVEN, FL 33880 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1675
       Built: 2025   Tax: $310 (2024)
    Community: West Winter Haven
    Single Family


    Estimated Monthly Payment: $1,719 (change assumption)
    Mortgage ($1,693) + Taxes in 2024 ($26)


    Taxes:$310

    Elementary School: Inwood Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Westwood Middle


  • 1569 LEMON AVE, WINTER HAVEN, FL 33881

    $349,90019 Days on yellowkey   MLS ID: TB8490457

    2 Days Off yellowkey (back on 4/22/2026)

    For Sale TB8490457 - 1569 LEMON AVE, WINTER HAVEN, FL 33881 15 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2151
       Built: 2016
    Monthly Fee: $23
       Tax: $5,582 (2025)
    Community: Eagle Crest
    Single Family


    Estimated Monthly Payment: $2,405 (change assumption)
    Mortgage ($1,917) + Fees ($23) + Taxes in 2025 ($465)


    Taxes:$5,582

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2323 BRASSIE CT, WINTER HAVEN, FL 33884

    $313,967201 Days on yellowkey   MLS ID: L4956626

    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


  • 1533 LEAMINGTON LN, WINTER HAVEN, FL 33884

    $304,366294 Days on yellowkey   MLS ID: L4954446

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

    For Sale L4954446 - 1533 LEAMINGTON LN, WINTER HAVEN, FL 33884 5 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2200
       Built: 2025
    Monthly Fee: $17
       Tax: $3,122 (2024)
    Community: Villa Mar Phase 3
    Single Family


    Estimated Monthly Payment: $1,945 (change assumption)
    Mortgage ($1,668) + Fees ($17) + Taxes in 2024 ($260)


    Taxes:$3,122

    Elementary School: Chain O Lakes Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Berkley Accelerated Middle


  • 1522 ECKART DR, WINTER HAVEN, FL 33881

    $379,90033 Days on yellowkey   MLS ID: L4959745

    REDUCED by $10,099 (2.6%) on 05/01/2026

    For Sale L4959745 - 1522 ECKART DR, WINTER HAVEN, FL 33881 60 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1524
       Built: 1982   Tax: $3,192 (2025)
    Community: Rochelle Gardens
    Single Family


    Estimated Monthly Payment: $2,348 (change assumption)
    Mortgage ($2,082) + Taxes in 2025 ($266)


    Taxes:$3,192

    Elementary School: Lake Alfred Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 132 ALACHUA DR, WINTER HAVEN, FL 33884

    $320,00069 Days on yellowkey   MLS ID: P4937917

    REDUCED by $1,000 (0.3%) on 05/01/2026

    For Sale P4937917 - 132 ALACHUA DR, WINTER HAVEN, FL 33884 43 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2466
       Built: 1976   Tax: $3,975 (2025)
    Community: Eloise Woods Lake Mariam Un
    Single Family


    Estimated Monthly Payment: $2,085 (change assumption)
    Mortgage ($1,753) + Taxes in 2025 ($331)


    Taxes:$3,975

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • WINTER HAVEN, FL 33880

    $390,000192 Days on yellowkey   MLS ID: TB8441385

    REDUCED by $9,500 (2.4%) on 04/22/2026

    SHORT SALE TB8441385 - WINTER HAVEN, FL 33880 13 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2242
       Built: 2007
    Monthly Fee: $15
       Tax: $3,305 (2024)
    Community: Ridge Acres Ph Ii
    Single Family


    Estimated Monthly Payment: $2,427 (change assumption)
    Mortgage ($2,137) + Fees ($15) + Taxes in 2024 ($275)


    Taxes:$3,305

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 715 GROVE ST, WINTER HAVEN, FL 33881

    $300,00046 Days on yellowkey   MLS ID: O6383497

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

    For Sale O6383497 - 715 GROVE ST, WINTER HAVEN, FL 33881 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1560
       Built: 2023
    Monthly Fee: $42
       Tax: $3,611 (2025)
    Community: Inman Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $1,987 (change assumption)
    Mortgage ($1,644) + Fees ($42) + Taxes in 2025 ($301)


    Taxes:$3,611

    Elementary School: Fred G. Garnier Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Westwood Middle


  • 555 LUCERNE BLVD, WINTER HAVEN, FL 33881

    $300,00056 Days on yellowkey   MLS ID: S5145385

    For Sale S5145385 - 555 LUCERNE BLVD, WINTER HAVEN, FL 33881 38 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1980
       Built: 2016
    Monthly Fee: $49
       Tax: $2,414 (2025)
    Community: Lakes/Lucerne Park Ph 4
    Single Family


    Estimated Monthly Payment: $1,894 (change assumption)
    Mortgage ($1,644) + Fees ($49) + Taxes in 2025 ($201)


    Taxes:$2,414

    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.