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Winter Haven, FL Homes for Sale — Page 22 | Realty.com
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3 bedsNew constructionWith a pool

Homes for Sale in Winter Haven, FL

Homes for Sale in Winter Haven, FL

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24 of 771 Listings
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Homes for Sale in Winter Haven, FL

24 of 771 Listings

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Thomas O'Leary

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  1. 5110 Kinsley Dr — photoPrice ReducedOpen house Wed, Oct 7 · 12:00 PM26Active

    $389,999

    5 bd · 4 ba · 3,030 sqft

    5110 Kinsley Dr, Winter Haven, FL

    Stephanie Morales, LLC · AXEN REALTY, LLC

  2. 150 El Dorado #105 — photoPrice Reduced36Active

    $94,900

    2 bd · 2 ba · 1,372 sqft

    150 El Dorado #105, Winter Haven, FL

    Rosalia Abreu · ALLSTATE REALTY SERVICES

  3. 2121 River Hawk Loop — photo30Active

    $342,900

    3 bd · 2 ba · 1,741 sqft

    2121 River Hawk Loop, Winter Haven, FL

    Rodrigo Gomes De Almeida · KELLER WILLIAMS REALTY SMART 1

  4. 409 21st St SW — photo53Active

    $550,000

    4 bd · 1 ba · 2,322 sqft

    409 21st St SW, Winter Haven, FL

    Joni Reiter · COLDWELL BANKER REALTY

  5. 1709 Teagan Ln — photoPrice Reduced45Active

    $248,000

    3 bd · 1 ba · 1,060 sqft

    1709 Teagan Ln, Winter Haven, FL

    Joel Marrero · KELLER WILLIAMS REALTY AT THE LAKES

  6. 3365 Costello Cir — photoPrice Reduced62Active

    $285,000

    5 bd · 3 ba · 2,522 sqft

    3365 Costello Cir, Winter Haven, FL

    Emily Lietz · ENGEL & VOELKERS LAKELAND

  7. 5780 Lakeside Landings Blvd — photoPrice Reduced39Active

    $299,900

    4 bd · 3 ba · 2,526 sqft

    5780 Lakeside Landings Blvd, Winter Haven, FL

    Harley Holmes · KELLER WILLIAMS REALTY SMART 1

  8. 2122 River Hawk Loop — photo46Active

    $344,900

    4 bd · 2 ba · 1,741 sqft

    2122 River Hawk Loop, Winter Haven, FL

    Rodrigo Gomes De Almeida · KELLER WILLIAMS REALTY SMART 1

  9. 4114 Fishermans Lndg — photo36Active

    $295,000

    3 bd · 2 ba · 1,992 sqft

    4114 Fishermans Lndg, Winter Haven, FL

    Patrick Thurmond · KELLER WILLIAMS REALTY SMART 1

  10. 154 2nd Street SW #Unit 7 — photo25Active

    $495,000

    2 bd · 3 ba · 1,640 sqft

    154 2nd Street SW #Unit 7, Winter Haven, FL

    Zachary Strang · POLK REALTY ADVISORS LLC

  11. 505 Holt Cir — photo16Active

    $185,000

    4 bd · 2 ba · 1,304 sqft

    505 Holt Cir, Winter Haven, FL

    Melissa Victor · MMV REAL ESTATE GROUP LLC

  12. 75 Sunset View Dr #75 — photoPrice Reduced44Active

    $405,000

    2 bd · 2 ba · 2,249 sqft

    75 Sunset View Dr #75, Winter Haven, FL

    Jill Lingenfelter · CENTURY 21 MYERS REALTY

  13. 1213 Michelangelo Ln — photoPrice Reduced13Active

    $549,500

    4 bd · 4 ba · 2,894 sqft

    1213 Michelangelo Ln, Winter Haven, FL

    Steven Koleno · BEYCOME OF FLORIDA LLC

  14. 702 Country Ln NE #702 — photo22Active

    $169,500

    2 bd · 2 ba · 1,252 sqft

    702 Country Ln NE #702, Winter Haven, FL

    Glenda Pruitt · FLORIDA HOME CHOICE REALTY

  15. 329 Lake Daisy Loop — photoPrice Reduced26Active

    $320,000

    3 bd · 2 ba · 1,563 sqft

    329 Lake Daisy Loop, Winter Haven, FL

    Jasmin Vargas · LA ROSA RTY WINTER GARDEN LLC

  16. 6194 Grey Heron Dr — photoPrice Reduced48Active

    $290,000

    3 bd · 2 ba · 1,711 sqft

    6194 Grey Heron Dr, Winter Haven, FL

    Amalia Lucena · TRUE FLORIDA REALTY LLC

  17. 10 Enclave Dr — photoPrice Reduced33Active

    $214,900

    2 bd · 2 ba · 1,368 sqft

    10 Enclave Dr, Winter Haven, FL

    Erin Floyd · COLDWELL BANKER REALTY

  18. 1757 Hummingbird Rd — photo30Active

    $428,900

    4 bd · 3 ba · 2,336 sqft

    1757 Hummingbird Rd, Winter Haven, FL

    Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

  19. 419 Avenue M NE — photoPrice Reduced17Active

    $244,999

    3 bd · 2 ba · 1,232 sqft

    419 Avenue M NE, Winter Haven, FL

    Stephen Hachey · FLAT FEE MLS REALTY

  20. 1004 Medinah Dr — photoPrice Reduced52Active

    $165,000

    2 bd · 2 ba · 1,278 sqft

    1004 Medinah Dr, Winter Haven, FL

    Susan Human · HUMAN TOUCH REAL ESTATE FIRM

  21. 1100 Carefree Cove Dr — photoPrice ReducedOpen house Wed, Oct 7 · 9:00 AM18Active

    $200,000

    3 bd · 2 ba · 1,019 sqft

    1100 Carefree Cove Dr, Winter Haven, FL

    Karen Albright · OPENDOOR BROKERAGE LLC

  22. 1871 Emily Dr — photoPrice Reduced66Active

    $304,900

    4 bd · 2 ba · 2,012 sqft

    1871 Emily Dr, Winter Haven, FL

    Cisco Romero · REALTY OF AMERICA

  23. 317 Avenue G SE — photoPrice Reduced21Active

    $240,000

    4 bd · 3 ba · 1,610 sqft

    317 Avenue G SE, Winter Haven, FL

    Paola Arias · MBA REALTY GROUP, INC

  24. 2734 Rochelle Dr — photo38Active

    $450,000

    4 bd · 3 ba · 2,829 sqft

    2734 Rochelle Dr, Winter Haven, FL

    Roberta San Juan · GATAP REALTY

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  • Your local brokerage

    TO

    Thomas O'Leary

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    Nearby areas

    ZIP codes

    • 34747 (2,308)
    • 34746 (1,655)
    • 33837 (1,450)
    • 33896 (1,137)
    • 33844 (1,103)
    • 34759 (922)
    • 33897 (894)
    • 33884 (682)

    Cities

    • Kissimmee (5,756)
    • Davenport (3,437)
    • Lakeland (2,278)
    • Haines City (1,100)
    • Lake Wales (766)
    • Auburndale (504)
    • Bartow (267)
    • Lake Alfred (266)

    Winter Haven, FL community profile

    Population
    58,351
    Median income
    $56,564
    Housing units
    26,800
    People per sq. mi.
    605.3
    Area
    96.4 sq. mi.

    Source: HJN community data

    Winter Haven housing market

    September 2026 · This period is still settling

    Winter Haven 12-month median sale price trend

    Selling at 99.7% of asking price

    Sales here are closing essentially at asking. MLS · 137 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 18, 2026

    Median sale price
    $270,000$207,500–$329,495 typical range
    Price per sq. ft.
    $161
    Sales
    135
    Paid in cash
    36.3%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

    Median list price
    $294,400
    Homes for sale
    762
    Median days on market
    48 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    -18.2%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

    Median home size
    1,632 sq. ft.