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Winter Haven Single Family Homes For Sale - 778 homes

Winter Haven Single Family Homes for Sale are located in Polk County, Florida. Find single family homes for sale in Winter Haven with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Haven single family houses.

Location: Winter Haven

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  • 6165 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884

    $469,000191 Days on yellowkey   MLS ID: P4937082

    1 Days Off yellowkey (back on 4/30/2026)

    For Sale P4937082 - 6165 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884 99 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2045
       Built: 2019
    Monthly Fee: $5
       Tax: $4,742 (2025)
    Community: Lake Ashton West Ph Ii North
    Single Family


    Estimated Monthly Payment: $2,970 (change assumption)
    Mortgage ($2,570) + Fees ($5) + Taxes in 2025 ($395)


    Taxes:$4,742

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2964 PLANTATION RD, WINTER HAVEN, FL 33884

    $579,900237 Days on yellowkey   MLS ID: O6352519

    REDUCED by $20,000 (3.3%) on 04/30/2026

    For Sale O6352519 - 2964 PLANTATION RD, WINTER HAVEN, FL 33884 42 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3614
       Built: 1989
    Monthly Fee: $137
       Tax: $618 (2024)
    Community: Cypresswood Plantations
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,366 (change assumption)
    Mortgage ($3,177) + Fees ($137) + Taxes in 2024 ($52)


    Taxes:$618

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3865 OSPREY POINTE CIR, WINTER HAVEN, FL 33884

    $255,000156 Days on yellowkey   MLS ID: S5141071

    REDUCED by $10,000 (3.8%) on 04/29/2026

    For Sale S5141071 - 3865 OSPREY POINTE CIR, WINTER HAVEN, FL 33884 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1603
       Built: 2006
    Monthly Fee: $210
       Tax: $3,716 (2025)
    Community: Osprey Pointe
    Single Family


    Estimated Monthly Payment: $1,917 (change assumption)
    Mortgage ($1,397) + Fees ($210) + Taxes in 2025 ($310)


    Taxes:$3,716

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 20 BREVARD DR SE, WINTER HAVEN, FL 33884

    $515,00048 Days on yellowkey   MLS ID: L4961284

    0 Days Off yellowkey (back on 4/29/2026)

    For Sale L4961284 - 20 BREVARD DR SE, WINTER HAVEN, FL 33884 67 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2340
       Built: 1976   Tax: $2,154 (2025)
    Community: Eloise Woods Lake Mariam Unit
    Single Family


    Estimated Monthly Payment: $3,001 (change assumption)
    Mortgage ($2,822) + Taxes in 2025 ($179)


    Taxes:$2,154

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3410 FOX RIDGE ST, WINTER HAVEN, FL 33884

    $275,000118 Days on yellowkey   MLS ID: P4937797

    0 Days Off yellowkey (back on 4/29/2026)

    For Sale P4937797 - 3410 FOX RIDGE ST, WINTER HAVEN, FL 33884 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1369
       Built: 1986   Tax: $1,686 (2025)
    Community: Fox Ridge Ph 02
    Single Family


    Estimated Monthly Payment: $1,647 (change assumption)
    Mortgage ($1,507) + Taxes in 2025 ($141)


    Taxes:$1,686

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 131 RUBY LAKE DR, WINTER HAVEN, FL 33884

    $375,00063 Days on yellowkey   MLS ID: P4938379

    For Sale P4938379 - 131 RUBY LAKE DR, WINTER HAVEN, FL 33884 62 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1914
       Built: 2000
    Monthly Fee: $71
       Tax: $4,453 (2025)
    Community: Ruby Lake Ph 01
    Single Family


    Estimated Monthly Payment: $2,497 (change assumption)
    Mortgage ($2,055) + Fees ($71) + Taxes in 2025 ($371)


    Taxes:$4,453

    Elementary School: Chain O Lakes Elem

    High School: Lake Region High

    Tax Year: 2025

    Middle School: Denison Middle


  • 3108 BUCKEYE POINTE DR, WINTER HAVEN, FL 33881

    $423,000114 Days on yellowkey   MLS ID: L4959442

    1 Days Off yellowkey (back on 4/28/2026)

    REDUCED by $3,000 (0.7%) on 04/23/2026

    For Sale L4959442 - 3108 BUCKEYE POINTE DR, WINTER HAVEN, FL 33881 39 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2249
       Built: 2004
    Monthly Fee: $25
       Tax: $5,809 (2025)
    Community: Buckeye Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,827 (change assumption)
    Mortgage ($2,318) + Fees ($25) + Taxes in 2025 ($484)


    Taxes:$5,809

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1454 GRAND CAYMAN CIR, WINTER HAVEN, FL 33884

    $259,99066 Days on yellowkey   MLS ID: O6396319

    REDUCED by $12,010 (4.4%) on 04/28/2026

    For Sale O6396319 - 1454 GRAND CAYMAN CIR, WINTER HAVEN, FL 33884 50 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1596
       Built: 1987
    Monthly Fee: $45
       Tax: $2,901 (2025)
    Community: Lake Dexter Moorings
    Spa: No

    Single Family


    Estimated Monthly Payment: $1,711 (change assumption)
    Mortgage ($1,425) + Fees ($45) + Taxes in 2025 ($242)


    Taxes:$2,901

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 132 BROAD ST, WINTER HAVEN, FL 33881

    $469,00078 Days on yellowkey   MLS ID: P4938236

    For Sale P4938236 - 132 BROAD ST, WINTER HAVEN, FL 33881 60 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2672
       Built: 2016
    Monthly Fee: $74
       Tax: $3,868 (2025)
    Community: Hampton Cove
    Single Family


    Estimated Monthly Payment: $2,966 (change assumption)
    Mortgage ($2,570) + Fees ($74) + Taxes in 2025 ($322)


    Taxes:$3,868

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 218 DENNIS AVE, WINTER HAVEN, FL 33880

    $246,90044 Days on yellowkey   MLS ID: L4961409

    For Sale L4961409 - 218 DENNIS AVE, WINTER HAVEN, FL 33880 27 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 1174
       Built: 1962   Tax: $2,994 (2025)
    Community: Jan Phyl Village Unit 03 A
    Single Family


    Estimated Monthly Payment: $1,602 (change assumption)
    Mortgage ($1,353) + Taxes in 2025 ($250)


    Taxes:$2,994

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 884 CAMBRIDGE DR, WINTER HAVEN, FL 33881

    $275,00044 Days on yellowkey   MLS ID: TB8502061

    SHORT SALE TB8502061 - 884 CAMBRIDGE DR, WINTER HAVEN, FL 33881 26 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2368
       Built: 2021
    Monthly Fee: $17
       Tax: $7,314 (2025)
    Community: Lucerne Park Reserve
    Single Family


    Estimated Monthly Payment: $2,133 (change assumption)
    Mortgage ($1,507) + Fees ($17) + Taxes in 2025 ($610)


    Taxes:$7,314

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5452 SAN PIETRO DR, WINTER HAVEN, FL 33884

    $349,99975 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

    $359,99975 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


  • 272 MEREDITH BLVD, WINTER HAVEN, FL 33881

    $274,99081 Days on yellowkey   MLS ID: G5109923

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale G5109923 - 272 MEREDITH BLVD, WINTER HAVEN, FL 33881 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1598
       Built: 2025
    Monthly Fee: $6
       Tax: $500 (2025)
    Community: Willowbrook North
    Single Family


    Estimated Monthly Payment: $1,554 (change assumption)
    Mortgage ($1,507) + Fees ($6) + Taxes in 2025 ($42)


    Taxes:$500

    Elementary School: Fred G. Garnier Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 1742 UPLAND LN, WINTER HAVEN, FL 33884

    $380,99049 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


  • 202 SAINT LUCIE RD, WINTER HAVEN, FL 33884

    $328,99948 Days on yellowkey   MLS ID: L4961340

    For Sale L4961340 - 202 SAINT LUCIE RD, WINTER HAVEN, FL 33884 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1764
       Built: 1973   Tax: $3,069 (2025)
    Community: Eloise Woods East Lake Mariam Unit
    Single Family


    Estimated Monthly Payment: $2,058 (change assumption)
    Mortgage ($1,803) + Taxes in 2025 ($256)


    Taxes:$3,069

    Elementary School: Elbert Elem

    High School: Winter Haven Senior

    Tax Year: 2025

    Middle School: Denison Middle


  • 153 LAKE OTIS RD, WINTER HAVEN, FL 33884

    $749,00089 Days on yellowkey   MLS ID: L4959536

    REDUCED by $26,000 (3.4%) on 04/24/2026

    For Sale L4959536 - 153 LAKE OTIS RD, WINTER HAVEN, FL 33884 93 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3913
       Built: 1968
    Monthly Fee: $100
       Tax: $5,530 (2025)
    Community: Lakewood
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,665 (change assumption)
    Mortgage ($4,104) + Fees ($100) + Taxes in 2025 ($461)


    Taxes:$5,530

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 920 GOTTHARD PASS DR, WINTER HAVEN, FL 33881

    $394,999140 Days on yellowkey   MLS ID: S5142092

    For Sale S5142092 - 920 GOTTHARD PASS DR, WINTER HAVEN, FL 33881 55 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2654
       Built: 2021   Tax: $5,532 (2025)
    Community: Lake Lucerne Ph 5
    Single Family


    Estimated Monthly Payment: $2,625 (change assumption)
    Mortgage ($2,164) + Taxes in 2025 ($461)


    Taxes:$5,532

    Elementary School: Lake Alfred Elem

    High School: Haines City Senior High

    Tax Year: 2025

    Middle School: Boone Middle


  • 1739 UPLAND LN, WINTER HAVEN, FL 33884

    $326,99049 Days on yellowkey   MLS ID: W7885115

    For Sale W7885115 - 1739 UPLAND LN, WINTER HAVEN, FL 33884 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1815
       Built: 2026
    Monthly Fee: $63

    Community: Ashton Covey
    Single Family


    Estimated Monthly Payment: $1,855 (change assumption)
    Mortgage ($1,792) + 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


  • 1726 UPLAND LN, WINTER HAVEN, FL 33884

    $386,99049 Days on yellowkey   MLS ID: W7885114

    For Sale W7885114 - 1726 UPLAND LN, WINTER HAVEN, FL 33884 21 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2797
       Built: 2026
    Monthly Fee: $63

    Community: Ashton Covey
    Single Family


    Estimated Monthly Payment: $2,183 (change assumption)
    Mortgage ($2,120) + 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




Why Bother Searching Elsewhere for Winter Haven Single Family Homes for Sale?

Winter Haven home, townhome, and condo, villa, and other listing sale data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on single family homes for sale in Winter Haven . You can use our website to view Multiple Listing Service (MLS) data on Winter Haven single family homes. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our Winter Haven single family home listings.



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.