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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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  • 6308 PINEHURST LOOP, WINTER HAVEN, FL 33884

    $456,900110 Days on yellowkey   MLS ID: A4678252

    For Sale A4678252 - 6308 PINEHURST LOOP, WINTER HAVEN, FL 33884 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2045
       Built: 2022
    Monthly Fee: $5
       Tax: $9,887 (2025)
    Community: Lake Ashton West Ph Ii North
    Single Family


    Estimated Monthly Payment: $3,332 (change assumption)
    Mortgage ($2,503) + Fees ($5) + Taxes in 2025 ($824)


    Taxes:$9,887

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4502 RAPALLO AVE, WINTER HAVEN, FL 33884

    $340,99021 Days on yellowkey   MLS ID: L4961043

    0 Days Off yellowkey (back on 4/13/2026)

    For Sale L4961043 - 4502 RAPALLO AVE, WINTER HAVEN, FL 33884 4 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2005
       Built: 2026
    Monthly Fee: $18

    Community: Villamar
    Single Family


    Estimated Monthly Payment: $1,886 (change assumption)
    Mortgage ($1,868) + Fees ($18) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3033 BUCKEYE POINTE DR, WINTER HAVEN, FL 33881

    $305,000264 Days on yellowkey   MLS ID: L4955159

    For Sale L4955159 - 3033 BUCKEYE POINTE DR, WINTER HAVEN, FL 33881 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2070
       Built: 2004
    Monthly Fee: $33
       Tax: $4,035 (2024)
    Community: Buckeye Pointe
    Single Family


    Estimated Monthly Payment: $2,040 (change assumption)
    Mortgage ($1,671) + Fees ($33) + Taxes in 2024 ($336)


    Taxes:$4,035

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 108 LAKE REGION BLVD N, WINTER HAVEN, FL 33881

    $425,000152 Days on yellowkey   MLS ID: L4957549

    REDUCED by $14,000 (3.2%) on 04/13/2026

    For Sale L4957549 - 108 LAKE REGION BLVD N, WINTER HAVEN, FL 33881 52 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2495
       Built: 1996
    Monthly Fee: $85
       Tax: $3,479 (2025)
    Community: Gates Of Lake Region
    Single Family


    Estimated Monthly Payment: $2,704 (change assumption)
    Mortgage ($2,329) + Fees ($85) + Taxes in 2025 ($290)


    Taxes:$3,479

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 1444 KINGFISH LN, WINTER HAVEN, FL 33884

    $270,00098 Days on yellowkey   MLS ID: P4937632

    REDUCED by $15,000 (5.3%) on 03/31/2026

    For Sale P4937632 - 1444 KINGFISH LN, WINTER HAVEN, FL 33884 58 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2005
       Built: 2004
    Monthly Fee: $45
       Tax: $2,715 (2025)
    Community: Lake Dexter Moorings
    Single Family


    Estimated Monthly Payment: $1,751 (change assumption)
    Mortgage ($1,479) + Fees ($45) + Taxes in 2025 ($226)


    Taxes:$2,715

    Elementary School: Garden Grove Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 21 CASARENA CT, WINTER HAVEN, FL 33881

    $285,000182 Days on yellowkey   MLS ID: L4956453

    For Sale L4956453 - 21 CASARENA CT, WINTER HAVEN, FL 33881 51 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 2045
       Built: 1984
    Monthly Fee: $310
       Tax: $3,325 (2024)
    Community: Casarena On Lakes
    Single Family


    Estimated Monthly Payment: $2,149 (change assumption)
    Mortgage ($1,562) + Fees ($310) + Taxes in 2024 ($277)


    Taxes:$3,325

    Elementary School: Inwood Elem

    High School: Winter Haven Senior

    Tax Year: 2024

    Middle School: Westwood Middle


  • 5323 MICKEY AVE, WINTER HAVEN, FL 33884

    $329,999263 Days on yellowkey   MLS ID: S5132794

    INCREASED by $5,000 (1.5%) on 04/13/2026

    For Sale S5132794 - 5323 MICKEY AVE, WINTER HAVEN, FL 33884 20 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2050
       Built: 2025
    Monthly Fee: $3

    Community: Seasons At Annabelle Estates
    Single Family


    Estimated Monthly Payment: $1,811 (change assumption)
    Mortgage ($1,808) + Fees ($3) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4494 RAPALLO AVE, WINTER HAVEN, FL 33884

    $316,90039 Days on yellowkey   MLS ID: L4960627

    1 Days Off yellowkey (back on 4/13/2026)

    For Sale L4960627 - 4494 RAPALLO AVE, WINTER HAVEN, FL 33884 22 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2005
       Built: 2026
    Monthly Fee: $18

    Community: Villamar
    Single Family


    Estimated Monthly Payment: $1,754 (change assumption)
    Mortgage ($1,736) + Fees ($18) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5268 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884

    $579,90026 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


  • 5389 SAN PIETRO DR, WINTER HAVEN, FL 33884

    $354,99961 Days on yellowkey   MLS ID: TB8482823

    0 Days Off yellowkey (back on 3/23/2026)

    For Sale TB8482823 - 5389 SAN PIETRO DR, WINTER HAVEN, FL 33884 25 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2470
       Built: 2025
    Monthly Fee: $53
       Tax: $2,688 (2025)
    Community: Villa Mar
    Single Family


    Estimated Monthly Payment: $2,222 (change assumption)
    Mortgage ($1,945) + Fees ($53) + Taxes in 2025 ($224)


    Taxes:$2,688

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 6212 PINEHURST LOOP, WINTER HAVEN, FL 33884

    $405,000255 Days on yellowkey   MLS ID: P4935966

    For Sale P4935966 - 6212 PINEHURST LOOP, WINTER HAVEN, FL 33884 79 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2175
       Built: 2022
    Monthly Fee: $5
       Tax: $5,880 (2024)
    Community: Lake Ashton West Ph Ii North
    Single Family


    Estimated Monthly Payment: $2,714 (change assumption)
    Mortgage ($2,219) + Fees ($5) + Taxes in 2024 ($490)


    Taxes:$5,880

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 232 COLLEGE GROVE CIR NE, WINTER HAVEN, FL 33881

    $350,00027 Days on yellowkey   MLS ID: L4960890

    For Sale L4960890 - 232 COLLEGE GROVE CIR NE, WINTER HAVEN, FL 33881 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2087
       Built: 1985   Tax: $2,372 (2025)
    Community: College Grove Rep
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,115 (change assumption)
    Mortgage ($1,918) + Taxes in 2025 ($198)


    Taxes:$2,372

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 191 MANDOLIN DR, WINTER HAVEN, FL 33884

    $399,14949 Days on yellowkey   MLS ID: G5109690

    5 Days Off yellowkey (back on 4/8/2026)

    For Sale G5109690 - 191 MANDOLIN DR, WINTER HAVEN, FL 33884 8 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2486
       Built: 2007
    Monthly Fee: $56
       Tax: $3,900 (2025)
    Community: Mandolin
    Single Family


    Estimated Monthly Payment: $2,568 (change assumption)
    Mortgage ($2,187) + Fees ($56) + Taxes in 2025 ($325)


    Taxes:$3,900

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2733 ATTWATER LOOP, WINTER HAVEN, FL 33884

    $359,500115 Days on yellowkey   MLS ID: P4937444

    For Sale P4937444 - 2733 ATTWATER LOOP, WINTER HAVEN, FL 33884 57 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2032
       Built: 2018
    Monthly Fee: $485
       Tax: $2,824 (2025)
    Community: Traditions Ph 02
    Single Family


    Estimated Monthly Payment: $2,690 (change assumption)
    Mortgage ($1,970) + Fees ($485) + Taxes in 2025 ($235)


    Taxes:$2,824

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 126 HOMEWOOD DR, WINTER HAVEN, FL 33880

    $335,00082 Days on yellowkey   MLS ID: L4959293

    For Sale L4959293 - 126 HOMEWOOD DR, WINTER HAVEN, FL 33880 83 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 1994   Tax: $1,396 (2025)
    Community: Homewood Sub
    Single Family


    Estimated Monthly Payment: $1,952 (change assumption)
    Mortgage ($1,836) + Taxes in 2025 ($116)


    Taxes:$1,396

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1051 LENA RUN CT, WINTER HAVEN, FL 33880

    $477,55582 Days on yellowkey   MLS ID: L4959294

    For Sale L4959294 - 1051 LENA RUN CT, WINTER HAVEN, FL 33880 43 photos

    Bed: 4   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2428
       Built: 2016
    Monthly Fee: $123
       Tax: $3,613 (2025)
    Community: Hidden Creek
    Single Family


    Estimated Monthly Payment: $3,041 (change assumption)
    Mortgage ($2,617) + Fees ($123) + Taxes in 2025 ($301)


    Taxes:$3,613

    Elementary School: Eagle Lake Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Westwood Middle


  • 1215 26TH ST NW, WINTER HAVEN, FL 33881

    $379,00054 Days on yellowkey   MLS ID: S5145609

    For Sale S5145609 - 1215 26TH ST NW, WINTER HAVEN, FL 33881 40 photos

    Bed: 4   Bath: 4.0
    Liv Area Sq Ft: 2083
       Built: 1940   Tax: $4,946 (2025)
    Community: Inwood #1
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,489 (change assumption)
    Mortgage ($2,077) + Taxes in 2025 ($412)


    Taxes:$4,946

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


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

    $238,90075 Days on yellowkey   MLS ID: P4937879

    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


  • 111 SUNSET DR E, WINTER HAVEN, FL 33881

    $215,00068 Days on yellowkey   MLS ID: P4937961

    For Sale P4937961 - 111 SUNSET DR E, WINTER HAVEN, FL 33881 44 photos

    Bed: 4   Bath: 1.0
    Liv Area Sq Ft: 2078
       Built: 1964   Tax: $1,193 (2025)
    Community: Chris Brown Cemetery Replat
    Single Family


    Estimated Monthly Payment: $1,277 (change assumption)
    Mortgage ($1,178) + Taxes in 2025 ($99)


    Taxes:$1,193

    Elementary School: Jewett School of the Arts

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 21 LAKE AVE, WINTER HAVEN, FL 33880

    $550,00070 Days on yellowkey   MLS ID: L4959669

    5 Days Off yellowkey (back on 4/7/2026)

    For Sale L4959669 - 21 LAKE AVE, WINTER HAVEN, FL 33880 27 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2018
       Built: 1957   Tax: $5,302 (2025)
    Community: Aqualane Heights
    Single Family


    Estimated Monthly Payment: $3,455 (change assumption)
    Mortgage ($3,014) + Taxes in 2025 ($442)


    Taxes:$5,302

    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.