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Winter Haven, FL Homes for Sale — Page 2 | 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

Realty.com

Lic. #BK3453168

Call Thomas
  1. 3304 Costello Cir — photo23Active

    $309,900

    3 bd · 2 ba · 1,525 sqft

    3304 Costello Cir, Winter Haven, FL

    Jason Stone · BHHS FLORIDA PROPERTIES GROUP

  2. 5850 Cypress Gardens Blvd #303 — photo74Active

    $179,000

    3 bd · 3 ba · 1,584 sqft

    5850 Cypress Gardens Blvd #303, Winter Haven, FL

    Michael Stone · THE STONES REAL ESTATE FIRM

  3. 5814 Driftwood Dr — photo30Active

    $295,000

    3 bd · 2 ba · 1,246 sqft

    5814 Driftwood Dr, Winter Haven, FL

    Solomon Gallant · S & D REAL ESTATE SERVICE LLC

  4. 645 Avenue M SE — photo41Active

    $330,000

    3 bd · 2 ba · 1,959 sqft

    645 Avenue M SE, Winter Haven, FL

    Bryan Dicks · COLDWELL BANKER REALTY

  5. 651 Lake Dexter Cir — photo24Active

    $200,000

    3 bd · 2 ba · 1,345 sqft

    651 Lake Dexter Cir, Winter Haven, FL

    Renee Butler · BROKERS REALTY OF CENTRAL FLOR

  6. 4302 Shadow Wood Ln — photo38Active

    $250,000

    2 bd · 2 ba · 1,507 sqft

    4302 Shadow Wood Ln, Winter Haven, FL

    Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS

  7. 624 Lake Elizabeth Dr — photo27Active

    $145,000

    2 bd · 1 ba · 1,209 sqft

    624 Lake Elizabeth Dr, Winter Haven, FL

    Cheryl Kypreos · HOMESMART

  8. 950 14th St NE — photo52Active

    $249,000

    2 bd · 3 ba · 1,380 sqft

    950 14th St NE, Winter Haven, FL

    Laura Slocumb · REMAX EXPERTS

  9. 521 Adriel Ave — photo13Active

    $350,000

    4 bd · 2 ba · 2,280 sqft

    521 Adriel Ave, Winter Haven, FL

    William Ortiz Collazo · LA ROSA REALTY KISSIMMEE

  10. 37 Lake Eloise Ln — photo38Active

    $515,000

    3 bd · 2 ba · 2,638 sqft

    37 Lake Eloise Ln, Winter Haven, FL

    Eileen Belanger · CENTURY 21 MYERS REALTY LAKE WALES

  11. 1215 Fairlane Ct NW — photo66Active

    $335,000

    3 bd · 2 ba · 2,148 sqft

    1215 Fairlane Ct NW, Winter Haven, FL

    Bree Allison · KELLER WILLIAMS TAMPA CENTRAL

  12. 2900 Crump Rd — photo51Active

    $425,000

    4 bd · 3 ba · 2,280 sqft

    2900 Crump Rd, Winter Haven, FL

    Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS

  13. 3039 Captain Jax Way — photo27Active

    $236,990

    3 bd · 3 ba · 1,423 sqft

    3039 Captain Jax Way, Winter Haven, FL

    Ben Goldstein · LENNAR REALTY

  14. 3059 Captain Jax Way — photo27Active

    $236,990

    3 bd · 3 ba · 1,423 sqft

    3059 Captain Jax Way, Winter Haven, FL

    Ben Goldstein · LENNAR REALTY

  15. 6055 Navona Way — photo37Active

    $336,990

    5 bd · 3 ba · 2,447 sqft

    6055 Navona Way, Winter Haven, FL

    Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

  16. 4230 Roberta Dr — photo37Active

    $360,000

    5 bd · 3 ba · 2,616 sqft

    4230 Roberta Dr, Winter Haven, FL

    Giovanni Hernandez · FORTEX REALTY INC

  17. 100 El Camino Dr #301 — photo35Active

    $149,900

    3 bd · 3 ba · 1,622 sqft

    100 El Camino Dr #301, Winter Haven, FL

    Craig Burke · CRAIG BURKE REAL ESTATE GROUP, LLC

  18. 6059 Navona Way — photo33Active

    $309,990

    4 bd · 3 ba · 1,866 sqft

    6059 Navona Way, Winter Haven, FL

    Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

  19. listing photo35Active

    $275,000

    3 bd · 2 ba · 1,285 sqft

    Address withheld · Winter Haven, FL

    Adriana Vazquez · HOME BANKERS REALTY, LLC

  20. 215 S Lake Howard Dr — photo52Active

    $419,000

    3 bd · 2 ba · 2,099 sqft

    215 S Lake Howard Dr, Winter Haven, FL

    Brandy Duncan · COLDWELL BANKER REALTY

  21. 930 Cattleman St — photo16Active

    $345,000

    5 bd · 3 ba · 2,254 sqft

    930 Cattleman St, Winter Haven, FL

    Claudia Lopez · EXP REALTY LLC

  22. 2668 Rutledge Ct — photo25Active

    $232,000

    3 bd · 2 ba · 1,419 sqft

    2668 Rutledge Ct, Winter Haven, FL

    Christa Ramirez · KELLER WILLIAMS REALTY

  23. 124 Edgewater Dr — photo39Active

    $239,999

    3 bd · 1 ba · 1,244 sqft

    124 Edgewater Dr, Winter Haven, FL

    Andres Diaz, Jr · EXP REALTY LLC

  24. 6283 Red Herring Dr — photo33Active

    $275,000

    3 bd · 2 ba · 1,747 sqft

    6283 Red Herring Dr, Winter Haven, FL

    Virgen Torres Soto · EQUINOVA HOME GROUP ,INC

123…33

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Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.
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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

    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)

    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.