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Winter Haven, FL Homes for Sale — Page 13 | 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. 1746 Hummingbird Rd — photo28Active

    $333,990

    3 bd · 2 ba · 1,593 sqft

    1746 Hummingbird Rd, Winter Haven, FL

    Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

  2. 4913 Kaia Ave — photo8Active

    $325,000

    3 bd · 2 ba · 1,300 sqft

    4913 Kaia Ave, Winter Haven, FL

    Lucy Elias · LEGACY REALTY PARTNERS, LLC.

  3. 232 Kings Pond Ave — photoPrice Reduced39Active

    $294,989

    3 bd · 2 ba · 1,417 sqft

    232 Kings Pond Ave, Winter Haven, FL

    Ray Colon · TRUE FLORIDA REALTY LLC

  4. 1124 Sawgrass Dr — photo71Active

    $355,000

    3 bd · 2 ba · 1,917 sqft

    1124 Sawgrass Dr, Winter Haven, FL

    Lori Raath · LAKE ASHTON REALTY INC.

  5. 503 Sweet Bay Cir — photoPrice Reduced58Active

    $224,500

    2 bd · 2 ba · 1,090 sqft

    503 Sweet Bay Cir, Winter Haven, FL

    Michael Stone · THE STONES REAL ESTATE FIRM

  6. 100 El Camino Dr #104 — photoPrice Reduced32Active

    $179,900

    3 bd · 2 ba · 1,579 sqft

    100 El Camino Dr #104, Winter Haven, FL

    Chrissi Jasso · ASSOCIATE REALTY

  7. 489 Village Cir SW — photo31Active

    $150,000

    2 bd · 2 ba · 1,008 sqft

    489 Village Cir SW, Winter Haven, FL

    Lindsey Funderburk · JT REALTY & ASSOCIATES

  8. 5386 San Pietro Dr — photoPrice Reduced25Active

    $321,299

    4 bd · 3 ba · 2,226 sqft

    5386 San Pietro Dr, Winter Haven, FL

    Michael Human · CASA FRESCA REALTY

  9. 3018 Royal Tern Dr — photoPrice Reduced22Active

    $269,900

    3 bd · 2 ba · 1,690 sqft

    3018 Royal Tern Dr, Winter Haven, FL

    Linda Urena · LARIMAR REALTY

  10. 7158 Summit Pl — photo15Active

    $299,000

    4 bd · 2 ba · 1,833 sqft

    7158 Summit Pl, Winter Haven, FL

    Glenda Pruitt · FLORIDA HOME CHOICE REALTY

  11. 819 Andrew St — photo2Active

    $399,990

    4 bd · 3 ba · 2,061 sqft

    819 Andrew St, Winter Haven, FL

    Adam Schott · DRB GROUP REALTY, LLC

  12. 3941 Warbler Dr — photoPrice Reduced41Active

    $219,900

    4 bd · 3 ba · 1,936 sqft

    3941 Warbler Dr, Winter Haven, FL

    Mark D'Italia · PROPERTY LOGIC RE

  13. 1557 N Lake Shipp Dr SW — photoPrice Reduced55Active

    $264,900

    3 bd · 2 ba · 1,172 sqft

    1557 N Lake Shipp Dr SW, Winter Haven, FL

    Tiffani Kline · HOUSE OF GLASS REAL ESTATE PM

  14. 419 Saint Anns Dr — photoPrice Reduced38Active

    $284,900

    3 bd · 2 ba · 1,505 sqft

    419 Saint Anns Dr, Winter Haven, FL

    Stacey Foskey · UNITED COUNTRY SMITH & ASSOCIATES

  15. 1105 Eagle Pond Dr #1105 — photoPrice Reduced40Active

    $160,000

    2 bd · 2 ba · 1,017 sqft

    1105 Eagle Pond Dr #1105, Winter Haven, FL

    Kayly Malinas, PA · JOHN WOOD REALTY, INC.

  16. 1207 32nd St NW — photoPrice Reduced20Active

    $229,000

    3 bd · 1 ba · 1,189 sqft

    1207 32nd St NW, Winter Haven, FL

    Jose Rojo · URBAN-O REAL ESTATE SOLUTIONS

  17. 108 Lagoon Rd — photo23Active

    $340,000

    3 bd · 2 ba · 1,735 sqft

    108 Lagoon Rd, Winter Haven, FL

    Sandy Music · MUSIC REALTY

  18. 408 Coleman Dr — photoPrice Reduced32Active

    $389,900

    4 bd · 2 ba · 2,420 sqft

    408 Coleman Dr, Winter Haven, FL

    Michael Mcgee · MAINSTAY BROKERAGE LLC

  19. 2240 Labrador Loop — photo13Active

    $323,965

    3 bd · 2 ba · 1,549 sqft

    2240 Labrador Loop, Winter Haven, FL

    Bill Maltbie · MALTBIE REALTY GROUP

  20. 2252 Labrador Loop — photo18Active

    $341,565

    3 bd · 2 ba · 1,815 sqft

    2252 Labrador Loop, Winter Haven, FL

    Bill Maltbie · MALTBIE REALTY GROUP

  21. 4498 Rapallo Ave E — photo14Active

    $330,900

    4 bd · 4 ba · 2,227 sqft

    4498 Rapallo Ave E, Winter Haven, FL

    George Lindsey, III · CAMBRIDGE REALTY OF CENTRAL FL

  22. 2236 Labrador Loop — photo21Active

    $350,165

    4 bd · 2 ba · 2,021 sqft

    2236 Labrador Loop, Winter Haven, FL

    Bill Maltbie · MALTBIE REALTY GROUP

  23. 2232 Labrador Loop — photo22Active

    $395,470

    4 bd · 3 ba · 2,797 sqft

    2232 Labrador Loop, Winter Haven, FL

    Bill Maltbie · MALTBIE REALTY GROUP

  24. 4123 Island Lakes Dr — photo48Active

    $470,000

    4 bd · 2 ba · 1,990 sqft

    4123 Island Lakes Dr, Winter Haven, FL

    Michelle Howard · KELLER WILLIAMS REALTY SMART 1

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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 (2,308)
    • 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)