REFINE SEARCH
Status
Keywords
Price
 
Bedrooms
Bathrooms
Garages
Liv Area Sq Ft
Min Year
Max Year
Property Types
No Image
Age Restricted
Foreclosure
Short Sale
Pets Allowed
Furnished
Pool
Spa
Reduced Price
Back on yellowkey
Possible Short Term Rental
Carports
Max Association Fee (monthly)
Max Monthly Payment
Search


Displaying: For Sale

Location: Winter Haven

Property Type(s): Single Family

Living Area Square Feet: 2000 to 2499

Winter Haven - 177 properties found

Sort:
  • 5452 SAN PIETRO DR, WINTER HAVEN, FL 33884

    $349,99938 Days on yellowkey   MLS ID: TB8491409

    0 Days Off yellowkey (back on 4/27/2026)

    REDUCED by $10,000 (2.8%) on 04/21/2026

    For Sale TB8491409 - 5452 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: $2,689 (2025)
    Community: Villa Mar
    Single Family


    Estimated Monthly Payment: $2,195 (change assumption)
    Mortgage ($1,918) + Fees ($53) + Taxes in 2025 ($224)


    Taxes:$2,689

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 5457 SAN PIETRO DR, WINTER HAVEN, FL 33884

    $359,99938 Days on yellowkey   MLS ID: TB8491423

    0 Days Off yellowkey (back on 4/27/2026)

    REDUCED by $5,000 (1.4%) on 04/21/2026

    For Sale TB8491423 - 5457 SAN PIETRO DR, WINTER HAVEN, FL 33884 26 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2470
       Built: 2025
    Monthly Fee: $53
       Tax: $2,689 (2025)
    Community: Villa Mar
    Single Family


    Estimated Monthly Payment: $2,250 (change assumption)
    Mortgage ($1,973) + Fees ($53) + Taxes in 2025 ($224)


    Taxes:$2,689

    Elementary School: Pinewood Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 615 ITUNA CIR E, WINTER HAVEN, FL 33881

    $341,900110 Days on yellowkey   MLS ID: L4958575

    2 Days Off yellowkey (back on 4/27/2026)

    For Sale L4958575 - 615 ITUNA CIR E, WINTER HAVEN, FL 33881 5 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2227
       Built: 2026
    Monthly Fee: $50

    Community: Harbor At Lake Henry
    Single Family


    Estimated Monthly Payment: $1,923 (change assumption)
    Mortgage ($1,873) + Fees ($50) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1936 CROSSROADS BLVD, WINTER HAVEN, FL 33881

    $495,00059 Days on yellowkey   MLS ID: L4959864

    REDUCED by $4,900 (1.0%) on 04/13/2026

    For Sale L4959864 - 1936 CROSSROADS BLVD, WINTER HAVEN, FL 33881 49 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2467
       Built: 2018
    Monthly Fee: $133
       Tax: $2,645 (2025)
    Community: Crossroads At Lake Region
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,066 (change assumption)
    Mortgage ($2,712) + Fees ($133) + Taxes in 2025 ($220)


    Taxes:$2,645

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3030 LAUREL OAK LN, WINTER HAVEN, FL 33884

    $339,990133 Days on yellowkey   MLS ID: L4957976

    For Sale L4957976 - 3030 LAUREL OAK LN, WINTER HAVEN, FL 33884 26 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2004
       Built: 2022
    Monthly Fee: $22
       Tax: $6,438 (2024)
    Community: Villamar Ph 4
    Single Family


    Estimated Monthly Payment: $2,421 (change assumption)
    Mortgage ($1,863) + Fees ($22) + Taxes in 2024 ($537)


    Taxes:$6,438

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3971 ISLAND LAKES DR, WINTER HAVEN, FL 33881

    $474,900168 Days on yellowkey   MLS ID: P4936971

    REDUCED by $5,000 (1.0%) on 04/17/2026

    For Sale P4936971 - 3971 ISLAND LAKES DR, WINTER HAVEN, FL 33881 27 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2023
       Built: 2014
    Monthly Fee: $17
       Tax: $4,603 (2024)
    Community: Island Lakes
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,003 (change assumption)
    Mortgage ($2,602) + Fees ($17) + Taxes in 2024 ($384)


    Taxes:$4,603

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1742 UPLAND LN, WINTER HAVEN, FL 33884

    $380,99012 Days on yellowkey   MLS ID: W7885110

    For Sale W7885110 - 1742 UPLAND LN, WINTER HAVEN, FL 33884 17 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2250
       Built: 2026
    Monthly Fee: $63

    Community: Ashton Covey
    Single Family


    Estimated Monthly Payment: $2,151 (change assumption)
    Mortgage ($2,088) + Fees ($63) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2026

    Middle School: Mclaughlin Academy Of Excellence


  • 4450 RAPALLO AVE, WINTER HAVEN, FL 33884

    $345,00038 Days on yellowkey   MLS ID: O6394240

    For Sale O6394240 - 4450 RAPALLO AVE, WINTER HAVEN, FL 33884 19 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2480
       Built: 2024
    Monthly Fee: $18
       Tax: $6,608 (2025)
    Community: Villamar Ph 5
    Single Family


    Estimated Monthly Payment: $2,459 (change assumption)
    Mortgage ($1,890) + Fees ($18) + Taxes in 2025 ($551)


    Taxes:$6,608

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 23 CASARENA CT, WINTER HAVEN, FL 33881

    $230,00011 Days on yellowkey   MLS ID: S5148554

    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: $1,896 (change assumption)
    Mortgage ($1,260) + 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


  • 3050 CRUMP RD, WINTER HAVEN, FL 33881

    $779,00091 Days on yellowkey   MLS ID: L4959091

    REDUCED by $10,900 (1.4%) on 04/19/2026

    For Sale L4959091 - 3050 CRUMP RD, WINTER HAVEN, FL 33881 98 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2397
       Built: 1982   Tax: $10,845 (2025)
    Community: Magnolia Shores
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,172 (change assumption)
    Mortgage ($4,268) + Taxes in 2025 ($904)


    Taxes:$10,845

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1913 QUAIL FIELDS CIR, WINTER HAVEN, FL 33884

    $335,990167 Days on yellowkey   MLS ID: W7880879

    For Sale W7880879 - 1913 QUAIL FIELDS CIR, WINTER HAVEN, FL 33884 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2021
       Built: 2026
    Monthly Fee: $63

    Community: Ashton Covey
    Single Family


    Estimated Monthly Payment: $1,904 (change assumption)
    Mortgage ($1,841) + Fees ($63) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2026

    Middle School: Mclaughlin Academy Of Excellence


  • 128 AVENUE D SW, WINTER HAVEN, FL 33880

    $235,00010 Days on yellowkey   MLS ID: L4961329

    For Sale L4961329 - 128 AVENUE D SW, WINTER HAVEN, FL 33880 1 photos

    Bed: 5   Bath: 1.5
    Liv Area Sq Ft: 2200
       Built: 1925   Tax: $3,693 (2025)
    Community: South College Add Rev
    Single Family


    Estimated Monthly Payment: $1,595 (change assumption)
    Mortgage ($1,288) + Taxes in 2025 ($308)


    Taxes:$3,693

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6004 KALEY DR, WINTER HAVEN, FL 33880

    $274,99010 Days on yellowkey   MLS ID: S5148589

    For Sale S5148589 - 6004 KALEY DR, WINTER HAVEN, FL 33880 24 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2128
       Built: 2004
    Monthly Fee: $14
       Tax: $4,038 (2025)
    Community: Sunridge Village East
    Single Family


    Estimated Monthly Payment: $1,857 (change assumption)
    Mortgage ($1,507) + Fees ($14) + Taxes in 2025 ($336)


    Taxes:$4,038

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2783 SAN MARCO WAY, WINTER HAVEN, FL 33884

    $349,99014 Days on yellowkey   MLS ID: O6400792

    For Sale O6400792 - 2783 SAN MARCO WAY, WINTER HAVEN, FL 33884 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2298
       Built: 2025
    Monthly Fee: $18
       Tax: $3,035 (2025)
    Community: Villamar Ph 5
    Single Family


    Estimated Monthly Payment: $2,189 (change assumption)
    Mortgage ($1,918) + Fees ($18) + Taxes in 2025 ($253)


    Taxes:$3,035

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3686 PLYMOUTH DR, WINTER HAVEN, FL 33884

    $369,900188 Days on yellowkey   MLS ID: P4936787

    For Sale P4936787 - 3686 PLYMOUTH DR, WINTER HAVEN, FL 33884 52 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2404
       Built: 2015
    Monthly Fee: $485
       Tax: $3,398 (2025)
    Community: Traditions Ph 02
    Single Family


    Estimated Monthly Payment: $2,795 (change assumption)
    Mortgage ($2,027) + Fees ($485) + Taxes in 2025 ($283)


    Taxes:$3,398

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 803 ANDREW ST, WINTER HAVEN, FL 33881

    $349,990189 Days on yellowkey   MLS ID: O6355618

    0 Days Off yellowkey (back on 4/24/2026)

    REDUCED by $15,000 (4.1%) on 04/07/2026

    For Sale O6355618 - 803 ANDREW ST, WINTER HAVEN, FL 33881 33 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2072
       Built: 2025
    Monthly Fee: $6
       Tax: $2,808 (2025)
    Community: Willowbrook North
    Single Family


    Estimated Monthly Payment: $2,158 (change assumption)
    Mortgage ($1,918) + Fees ($6) + Taxes in 2025 ($234)


    Taxes:$2,808

    Elementary School: Lake Alfred Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 1327 SALISBURY DR, WINTER HAVEN, FL 33881

    $334,90019 Days on yellowkey   MLS ID: TB8498339

    For Sale TB8498339 - 1327 SALISBURY DR, WINTER HAVEN, FL 33881 33 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2358
       Built: 2018
    Monthly Fee: $38
       Tax: $5,334 (2025)
    Community: Dundee Station
    Single Family


    Estimated Monthly Payment: $2,318 (change assumption)
    Mortgage ($1,835) + Fees ($38) + Taxes in 2025 ($445)


    Taxes:$5,334

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 496 TERRANOVA ST, WINTER HAVEN, FL 33884

    $449,00088 Days on yellowkey   MLS ID: O6380041

    REDUCED by $11,000 (2.4%) on 04/11/2026

    For Sale O6380041 - 496 TERRANOVA ST, WINTER HAVEN, FL 33884 45 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2357
       Built: 2004
    Monthly Fee: $56
       Tax: $6,005 (2025)
    Community: Terranova Ph 02
    Single Family


    Estimated Monthly Payment: $3,017 (change assumption)
    Mortgage ($2,460) + Fees ($56) + Taxes in 2025 ($500)


    Taxes:$6,005

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 1138 MICHELANGELO LN, WINTER HAVEN, FL 33884

    $399,90024 Days on yellowkey   MLS ID: S5147440

    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: $2,602 (change assumption)
    Mortgage ($2,191) + Fees ($55) + Taxes in 2025 ($356)


    Taxes:$4,275

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 262 SANTA ROSA DR, WINTER HAVEN, FL 33884

    $350,00054 Days on yellowkey   MLS ID: L4960100

    REDUCED by $45,000 (11.4%) on 04/23/2026

    For Sale L4960100 - 262 SANTA ROSA DR, WINTER HAVEN, FL 33884 41 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2336
       Built: 1987
    Monthly Fee: $46
       Tax: $739 (2025)
    Community: Overlook Estates
    Single Family


    Estimated Monthly Payment: $2,025 (change assumption)
    Mortgage ($1,918) + Fees ($46) + Taxes in 2025 ($62)


    Taxes:$739

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison 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.