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Winter Haven, FL Homes for Sale — Page 31 | 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 776 Listings
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Homes for Sale in Winter Haven, FL

24 of 776 Listings

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Thomas O'Leary

Realty.com

Lic. #BK3453168

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  1. 239 Golf Aire Blvd — photoPrice Reduced87Active

    $349,999

    3 bd · 3 ba · 2,263 sqft

    239 Golf Aire Blvd, Winter Haven, FL

    Christina Ashley · DALTON WADE INC

  2. 400 El Camino Dr #223 — photoPrice Reduced11Active

    $59,900

    1 bd · 1 ba · 850 sqft

    400 El Camino Dr #223, Winter Haven, FL

    Scott Cohara · KELLER WILLIAMS CLASSIC

  3. 21 Casarena Ct — photo51Active

    $285,000

    2 bd · 3 ba · 2,045 sqft

    21 Casarena Ct, Winter Haven, FL

    Kami Rickert · HOMETRUST REAL ESTATE & PTY MGT

  4. 5331 Mickey Ave — photoPrice ReducedOpen house Wed, Oct 7 · 12:00 PM21Active

    $354,999

    4 bd · 3 ba · 2,670 sqft

    5331 Mickey Ave, Winter Haven, FL

    Stephanie Morales, LLC · AXEN REALTY, LLC

  5. 6033 Grand Oaks Dr SE — photoPrice Reduced32Active

    $129,900

    2 bd · 2 ba · 1,120 sqft

    6033 Grand Oaks Dr SE, Winter Haven, FL

    Peggy Lewellen · COLDWELL BANKER REALTY

  6. 2307 Scarlet Ave — photoPrice Reduced26Active

    $260,000

    3 bd · 2 ba · 1,343 sqft

    2307 Scarlet Ave, Winter Haven, FL

    Stephanie Florez · CENTURY 21 WOLF'S CROSSING REALTY

  7. 1601 Roselawn St SW — photoPrice Reduced13Active

    $256,500

    2 bd · 1 ba · 1,099 sqft

    1601 Roselawn St SW, Winter Haven, FL

    Gabriel Rivera Gonzalez · LA ROSA REALTY PRESTIGE

  8. 344 Alexzander Way — photoPrice Reduced36Active

    $385,000

    5 bd · 3 ba · 2,696 sqft

    344 Alexzander Way, Winter Haven, FL

    Andres Ramirez · DALTON WADE INC

  9. listing photoPrice Reduced13Active

    $370,900

    4 bd · 3 ba · 2,242 sqft

    Address withheld · Winter Haven, FL

    Erica Ranson · BROOKS REALTY GROUP LLC

  10. 919 Avenue S SE — photoPrice Reduced36Active

    $330,000

    3 bd · 2 ba · 1,751 sqft

    919 Avenue S SE, Winter Haven, FL

    Emily Ward · EXP REALTY LLC

  11. 1122 Brimstone Cir — photo17Active

    $325,000

    3 bd · 2 ba · 1,690 sqft

    1122 Brimstone Cir, Winter Haven, FL

    Carolina Cruz Acedo · LPT REALTY, LLC

  12. 757 Reggie Rd — photo18Active

    $303,000

    3 bd · 2 ba · 1,432 sqft

    757 Reggie Rd, Winter Haven, FL

    Maria Cendon · LPT REALTY, LLC

  13. 649 Broadmoor Cir — photoPrice Reduced33Active

    $120,000

    2 bd · 2 ba · 1,278 sqft

    649 Broadmoor Cir, Winter Haven, FL

    Bill Sprys · SUCCESS INVESTMENT REALTY

  14. 1740 2nd St NE — photoPrice Reduced7Active

    $225,000

    3 bd · 2 ba · 1,683 sqft

    1740 2nd St NE, Winter Haven, FL

    Daryl Ash, II · KELLER WILLIAMS REALTY SMART

  15. 3843 Eloise Estates Ct — photoPrice Reduced32Active

    $280,000

    3 bd · 2 ba · 1,600 sqft

    3843 Eloise Estates Ct, Winter Haven, FL

    Lamanda Jones · CENTURY 21 WATSON & MYERS REALTY

  16. 602 Taylor Blvd — photoPrice Reduced19Active

    $220,000

    3 bd · 2 ba · 1,242 sqft

    602 Taylor Blvd, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  17. 136 Madera Dr — photo19Active

    $170,380

    3 bd · 2 ba · 1,448 sqft

    136 Madera Dr, Winter Haven, FL

    Casandra Vann · KELLER WILLIAMS REALTY SMART

  18. 3307 Fox Ridge Dr — photoPrice Reduced26Active

    $230,000

    3 bd · 2 ba · 1,253 sqft

    3307 Fox Ridge Dr, Winter Haven, FL

    Casandra Vann · KELLER WILLIAMS REALTY SMART

  19. 1100 Martinique Dr #117 — photo13Active

    $95,000

    1 bd · 1 ba · 1,078 sqft

    1100 Martinique Dr #117, Winter Haven, FL

    Monique Morgan · LA ROSA REALTY LLC

  20. 1709 Linz Ct — photoPrice Reduced71Active

    $248,000

    2 bd · 2 ba · 1,164 sqft

    1709 Linz Ct, Winter Haven, FL

    Marti Sutton · CENTURY 21 WATSON & MYERS REALTY

  21. 1997 26th St NW — photoPrice Reduced30Active

    $189,900

    3 bd · 2 ba · 1,166 sqft

    1997 26th St NW, Winter Haven, FL

    Angela Chapman · CAPITAL REALTY GROUP FLORIDA

  22. 1818 6th St SE — photoPrice Reduced69Active

    $479,000

    5 bd · 3 ba · 2,006 sqft

    1818 6th St SE, Winter Haven, FL

    Washington Costa · GARCIA REALTY GROUP

  23. 3923 Baldwin Ln — photoPrice Reduced41Active

    $253,900

    3 bd · 2 ba · 1,719 sqft

    3923 Baldwin Ln, Winter Haven, FL

    Brian Reeves · LPT REALTY, LLC

  24. 601 Avenue U NE — photoPrice Reduced39Active

    $199,900

    2 bd · 1 ba · 1,274 sqft

    601 Avenue U NE, Winter Haven, FL

    Brian Reeves · LPT REALTY, LLC

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    TO

    Thomas O'Leary

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    Lic. #BK3453168

    Call Thomas

    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)