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Winter Haven, FL Homes for Sale — Page 27 | 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 1,549 Listings
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Homes for Sale in Winter Haven, FL

24 of 1,549 Listings

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Thomas O'Leary

Realty.com

Lic. #BK3453168

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  1. 1734 Hummingbird Road — photo37Active

    $350,990

    4 bd · 3 ba · 2,308 sqft

    1734 Hummingbird Road, Winter Haven, FL

    Paul King · DR HORTON REALTY OF CENTRAL FLORIDA LLC

  2. 544 Ituna Circle — photoPrice Reduced4Active

    $336,900

    3 bd · 2 ba · 2,005 sqft

    544 Ituna Circle, Winter Haven, FL

    George Lindsey, III · CAMBRIDGE REALTY OF CENTRAL FL

  3. 665 Broadmoor Circle — photo36Active

    $165,000

    2 bd · 2 ba · 1,139 sqft

    665 Broadmoor Circle, Winter Haven, FL

    Rayven Santiago · KELLER WILLIAMS REALTY Y

  4. 1765 Hummingbird Road — photo26Active

    $329,990

    4 bd · 2 ba · 1,828 sqft

    1765 Hummingbird Road, Winter Haven, FL

    Paul King · DR HORTON REALTY OF CENTRAL FLORIDA LLC

  5. 2519 Avenue E SW — photoPrice Reduced24Active

    $299,900

    3 bd · 2 ba · 1,675 sqft

    2519 Avenue E SW, Winter Haven, FL

    Gloria Johnpierre · SIVEN PREMIER REAL ESTATE

  6. 2519 Avenue E SW — photoPrice Reduced24Active

    $299,900

    3 bd · 2 ba · 1,675 sqft

    2519 Avenue E SW, Winter Haven, FL

    Gloria Johnpierre · SIVEN PREMIER REAL ESTATE

  7. 1100 Martinique Dr #106 — photo33Active

    $129,500

    2 bd · 1 ba · 826 sqft

    1100 Martinique Dr #106, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  8. 665 Broadmoor Cir — photo36Active

    $165,000

    2 bd · 2 ba · 1,139 sqft

    665 Broadmoor Cir, Winter Haven, FL

    Rayven Santiago · KELLER WILLIAMS REALTY Y

  9. 790 Avenue Q SE — photo26Active

    $185,000

    2 bd · 1 ba · 934 sqft

    790 Avenue Q SE, Winter Haven, FL

    Amy Reynolds · LOCKHART & ASSOCIATES INC

  10. 1765 Hummingbird Rd — photo26Active

    $355,990

    4 bd · 2 ba · 1,828 sqft

    1765 Hummingbird Rd, Winter Haven, FL

    Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

  11. 144 Waterside Cir — photoPrice Reduced37Active

    $299,000

    3 bd · 2 ba · 1,847 sqft

    144 Waterside Cir, Winter Haven, FL

    Ythamarie Rosario · KELLER WILLIAMS ADVANTAGE III

  12. 128 N Lake Florence Drive — photo50Active

    $399,999

    3 bd · 2 ba · 2,167 sqft

    128 N Lake Florence Drive, Winter Haven, FL

    Trevor Albergo · KELLER WILLIAMS REALTY

  13. 1500 Avenue H NE — photo33Active

    $224,500

    4 bd · 2 ba · 1,784 sqft

    1500 Avenue H NE, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  14. 128 N Lake Florence Dr — photo50Active

    $399,999

    3 bd · 2 ba · 2,167 sqft

    128 N Lake Florence Dr, Winter Haven, FL

    Trevor Albergo · KELLER WILLIAMS REALTY

  15. 2820 Traditions Blvd S — photo44Active

    $309,900

    3 bd · 2 ba · 1,823 sqft

    2820 Traditions Blvd S, Winter Haven, FL

    Stephanie Bombinski · AGENT GROUP REALTY

  16. 1500 Avenue H NE — photo33Active

    $224,500

    4 bd · 2 ba · 1,784 sqft

    1500 Avenue H NE, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  17. 1755 Beth Lane — photo42Active

    $435,000

    3 bd · 2 ba · 2,702 sqft

    1755 Beth Lane, Winter Haven, FL

    Joni Reiter · COLDWELL BANKER REALTY

  18. 2820 Traditions Boulevard S — photo44Active

    $309,900

    3 bd · 2 ba · 1,823 sqft

    2820 Traditions Boulevard S, Winter Haven, FL

    Stephanie Bombinski · AGENT GROUP REALTY

  19. 144 Waterside Circle — photo37Active

    $305,000

    3 bd · 2 ba · 1,847 sqft

    144 Waterside Circle, Winter Haven, FL

    Ythamarie Rosario · KELLER WILLIAMS ADVANTAGE III

  20. 1755 Beth Ln — photo42Active

    $435,000

    3 bd · 2 ba · 2,702 sqft

    1755 Beth Ln, Winter Haven, FL

    Joni Reiter · COLDWELL BANKER REALTY

  21. 6022 Grey Heron Drive — photoPrice Reduced29Active

    $320,000

    5 bd · 3 ba · 2,577 sqft

    6022 Grey Heron Drive, Winter Haven, FL

    Xiomara Pichardo · LPT REALTY, LLC

  22. 6022 Grey Heron Dr — photoPrice Reduced29Active

    $300,000

    5 bd · 3 ba · 2,577 sqft

    6022 Grey Heron Dr, Winter Haven, FL

    Xiomara Pichardo · LPT REALTY, LLC

  23. 2004 Leisure Dr — photoPrice Reduced44Active

    $675,000

    4 bd · 3 ba · 2,312 sqft

    2004 Leisure Dr, Winter Haven, FL

    Ralph Harvey · LISTWITHFREEDOM.COM

  24. 3334 Avenue J NW — photoPrice Reduced45Active

    $249,765

    3 bd · 2 ba · 1,473 sqft

    3334 Avenue J NW, Winter Haven, FL

    Nicki Salas Fuentes · ELEVE REAL ESTATE LLC

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    TO

    Thomas O'Leary

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    Lic. #BK3453168

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    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.

    Nearby areas

    ZIP codes

    • 34747 (2,310)
    • 34746 (1,665)
    • 33837 (1,454)
    • 33896 (1,129)
    • 33844 (1,103)
    • 34759 (925)
    • 33897 (895)
    • 33884 (687)

    Cities

    • Kissimmee (2,913)
    • KISSIMMEE (2,856)
    • DAVENPORT (1,727)
    • Davenport (1,708)
    • Lakeland (1,157)
    • LAKELAND (1,121)
    • HAINES CITY (550)
    • Haines City (549)