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Winter Haven, FL Homes for Sale — Page 3 | 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 775 Listings
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Homes for Sale in Winter Haven, FL

24 of 775 Listings

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Thomas O'Leary

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  1. 5281 Pebble Beach Blvd — photo90Active

    $279,900

    3 bd · 2 ba · 1,495 sqft

    5281 Pebble Beach Blvd, Winter Haven, FL

    Brad Kirwan · GLOBAL LIFESTYLE LLC

  2. 815 Lake Jessie Dr — photo30Active

    $595,000

    4 bd · 4 ba · 4,128 sqft

    815 Lake Jessie Dr, Winter Haven, FL

    Aline Oliveira · META ONE REALTY GROUP LLC

  3. 716 Avenue I NE — photo42Active

    $258,500

    3 bd · 2 ba · 1,559 sqft

    716 Avenue I NE, Winter Haven, FL

    Maria Deary · COLDWELL BANKER REALTY

  4. 5369 San Pietro Dr — photoPrice Reduced8Active

    $344,390

    4 bd · 3 ba · 2,226 sqft

    5369 San Pietro Dr, Winter Haven, FL

    Michael Human · CASA FRESCA REALTY

  5. 1540 S Lake Shipp Dr — photo21Active

    $215,000

    2 bd · 1 ba · 1,350 sqft

    1540 S Lake Shipp Dr, Winter Haven, FL

    Flo Orphee · LPT REALTY, LLC

  6. 117 Homewood Dr — photo51Active

    $350,000

    3 bd · 2 ba · 1,762 sqft

    117 Homewood Dr, Winter Haven, FL

    Lisa Matheny · ENGEL & VOELKERS LAKELAND

  7. 4064 Phoenician Way — photo75Active

    $449,900

    3 bd · 2 ba · 2,354 sqft

    4064 Phoenician Way, Winter Haven, FL

    Lori Raath · LAKE ASHTON REALTY INC.

  8. 1711 Garden Lake Dr #1711 — photo11Active

    $170,000

    1 bd · 1 ba · 828 sqft

    1711 Garden Lake Dr #1711, Winter Haven, FL

    Kayly Malinas, PA · JOHN WOOD REALTY, INC.

  9. 948 Summer Glen Dr — photo39Active

    $259,990

    3 bd · 2 ba · 1,690 sqft

    948 Summer Glen Dr, Winter Haven, FL

    Ivette Penalver Cancine · AXEN REALTY LLC

  10. 1631 Linz Ct — photo34Active

    $190,500

    2 bd · 2 ba · 1,231 sqft

    1631 Linz Ct, Winter Haven, FL

    Pat Pearson · VIEWPOINT VALUE REALTY

  11. 4028 Phoenician Way — photo67Active

    $330,000

    2 bd · 2 ba · 1,784 sqft

    4028 Phoenician Way, Winter Haven, FL

    Lori Raath · LAKE ASHTON REALTY INC.

  12. 7808 Waterview Way — photo26Active

    $115,000

    2 bd · 2 ba · 559 sqft

    7808 Waterview Way, Winter Haven, FL

    Ashley Adams · HARPER REALTY FL, LLC

  13. 7002 Summit Cir — photo25Active

    $340,000

    3 bd · 2 ba · 1,888 sqft

    7002 Summit Cir, Winter Haven, FL

    Angela Fowler · ANGELA FOWLER REAL ESTATE, LLC

  14. 1117 Michelangelo Ln — photo67Active

    $375,000

    4 bd · 3 ba · 2,626 sqft

    1117 Michelangelo Ln, Winter Haven, FL

    Nellymar Albelo PLLC · ORANGE SLICE PROPERTIES

  15. 9504 Waterford Oaks Blvd — photo66Active

    $725,000

    5 bd · 3 ba · 2,916 sqft

    9504 Waterford Oaks Blvd, Winter Haven, FL

    Brooke Boyette · KELLER WILLIAMS TAMPA PROPERTIES

  16. 3005 Captain Jax Way — photoPrice Reduced27Active

    $236,990

    3 bd · 3 ba · 1,423 sqft

    3005 Captain Jax Way, Winter Haven, FL

    Ben Goldstein · LENNAR REALTY

  17. 1475 Grand Cayman Cir — photo59Active

    $359,000

    3 bd · 2 ba · 2,066 sqft

    1475 Grand Cayman Cir, Winter Haven, FL

    Tina Heim, PA · KELLER WILLIAMS REALTY

  18. 400 Bayou Rd — photo72Active

    $258,000

    2 bd · 2 ba · 1,277 sqft

    400 Bayou Rd, Winter Haven, FL

    Tina McDonald · OLYMPUS EXECUTIVE REALTY INC

  19. 2796 Whispering Trails Dr — photo1Active

    $190,000

    3 bd · 2 ba · 1,158 sqft

    2796 Whispering Trails Dr, Winter Haven, FL

    Lucy Martinez · KELLER WILLIAMS REALTY SMART 1

  20. 4750 Osprey Way — photo59Active

    $305,000

    4 bd · 2 ba · 1,986 sqft

    4750 Osprey Way, Winter Haven, FL

    William Figueroa · SOVEREIGN REAL ESTATE GROUP

  21. 1210 32nd St NW — photo36Active

    $179,900

    3 bd · 1 ba · 936 sqft

    1210 32nd St NW, Winter Haven, FL

    Teresa Homan · MAINSTAY BROKERAGE LLC

  22. 5707 E Lake Fox Dr — photo38Active

    $260,000

    4 bd · 3 ba · 2,300 sqft

    5707 E Lake Fox Dr, Winter Haven, FL

    Susan Brown · COLDWELL BANKER REALTY

  23. 2 Casarena Ct — photo37Active

    $309,900

    3 bd · 3 ba · 2,377 sqft

    2 Casarena Ct, Winter Haven, FL

    Craig Burke · CRAIG BURKE REAL ESTATE GROUP, LLC

  24. 1205 Eagle Pond Dr #1205 — photo21Active

    $162,000

    2 bd · 2 ba · 1,017 sqft

    1205 Eagle Pond Dr #1205, Winter Haven, FL

    Gabriel Silva Andrada · FLORIDA SPIRIT HOMES

1234…33

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    Thomas O'Leary

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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)