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Winter Haven, FL Homes for Sale | 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 796 Listings
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Homes for Sale in Winter Haven, FL

24 of 796 Listings

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Thomas O'Leary

Realty.com

Lic. #BK3453168

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  1. 1358 Buckeye Trace Blvd — photoNew10Active

    $270,000

    3 bd · 2 ba · 1,820 sqft

    1358 Buckeye Trace Blvd, Winter Haven, FL

    Don Jerue · KELLER WILLIAMS REALTY SMART 1

  2. NewActive

    $295,000

    4 bd · 2 ba · 1,876 sqft

    4956 Jackson St, Winter Haven, FL

    Anthony Medina · KELLER WILLIAMS REALTY SMART 1

  3. 503 William Ave — photoNew25Active

    $269,900

    3 bd · 2 ba · 1,372 sqft

    503 William Ave, Winter Haven, FL

    Miriam Adame · OAKSTRAND REALTY

  4. 4043 Bedford Ave — photoNew65Active

    $359,900

    2 bd · 2 ba · 1,871 sqft

    4043 Bedford Ave, Winter Haven, FL

    Deanna Stone · THE STONES REAL ESTATE FIRM

  5. 668 Reggie Rd — photoNew42Active

    $285,000

    3 bd · 2 ba · 1,432 sqft

    668 Reggie Rd, Winter Haven, FL

    Kenny Medina · LPT REALTY, LLC

  6. 2021 Canton Park Dr — photo3Active

    $325,000

    3 bd · 2 ba · 1,690 sqft

    2021 Canton Park Dr, Winter Haven, FL

    Maria Olmos, LLC · LA ROSA REALTY ORLANDO LLC

  7. 6733 Kensington Dr NE — photoNew71Active

    $165,500

    2 bd · 2 ba · 1,224 sqft

    6733 Kensington Dr NE, Winter Haven, FL

    Cynthia Cole · FLORIDA REALTY MARKETPLACE

  8. 417 Avenue G SE — photoNew42Active

    $380,000

    3 bd · 2 ba · 1,020 sqft

    417 Avenue G SE, Winter Haven, FL

    Arlin De Leon, PA · LA ROSA REALTY KISSIMMEE

  9. 997 Harold Pass — photoNewOpen house Sat, Oct 17 · 12:00 PM34Active

    $299,999

    4 bd · 3 ba · 1,933 sqft

    997 Harold Pass, Winter Haven, FL

    Andrea Heck · KELLER WILLIAMS TAMPA CENTRAL

  10. 125 Whittier Ln — photoNew33Active

    $225,000

    3 bd · 2 ba · 1,245 sqft

    125 Whittier Ln, Winter Haven, FL

    Lori Roberts · GOLD HEART REALTY LLC

  11. 829 Sun Ridge Village Dr — photoNew32Active

    $369,900

    4 bd · 3 ba · 3,020 sqft

    829 Sun Ridge Village Dr, Winter Haven, FL

    Robert Salmons · ENTERA REALTY LLC

  12. 222 Cloverdale Rd — photoNewOpen house Fri, Oct 16 · 9:00 AM22Active

    $300,000

    3 bd · 3 ba · 1,867 sqft

    222 Cloverdale Rd, Winter Haven, FL

    Karen Albright · OPENDOOR BROKERAGE LLC

  13. 240 Westwood Ave — photoNew64Active

    $249,900

    3 bd · 2 ba · 1,140 sqft

    240 Westwood Ave, Winter Haven, FL

    Nicole Silva · RE/MAX COLLECTIVE

  14. 114 Belmont Dr — photoNew39Active

    $459,000

    4 bd · 2 ba · 2,069 sqft

    114 Belmont Dr, Winter Haven, FL

    Mark Bouchard · MLB FREEDOM DESTINATIONS

  15. 1921 Manor Cir SE — photoNew87Active

    $1,295,000

    3 bd · 3 ba · 2,375 sqft

    1921 Manor Cir SE, Winter Haven, FL

    Dee Norris · NEXTHOME NORRIS & COMPANY REAL

  16. 5365 San Pietro Dr — photoNew1Active

    $319,999

    4 bd · 3 ba · 2,039 sqft

    5365 San Pietro Dr, Winter Haven, FL

    Michael Human · CASA FRESCA REALTY

  17. 138 Grove Branch Rd — photoNew46Active

    $289,000

    4 bd · 2 ba · 1,851 sqft

    138 Grove Branch Rd, Winter Haven, FL

    Michael Stone · THE STONES REAL ESTATE FIRM

  18. 6245 Botticella Blvd — photoNew15Active

    $294,990

    5 bd · 3 ba · 2,112 sqft

    6245 Botticella Blvd, Winter Haven, FL

    Ben Goldstein · LENNAR REALTY

  19. 703 Avenue L SE — photoNew22Active

    $278,000

    4 bd · 2 ba · 1,830 sqft

    703 Avenue L SE, Winter Haven, FL

    Sandra Wyhnanskyj, PA · OLYMPUS EXECUTIVE REALTY INC

  20. 1759 Vanilla St — photoNew1Active

    $364,745

    5 bd · 3 ba · 2,470 sqft

    1759 Vanilla St, Winter Haven, FL

    Michael Human · CASA FRESCA REALTY

  21. 1764 Vanilla St — photoNew1Active

    $410,620

    4 bd · 3 ba · 2,292 sqft

    1764 Vanilla St, Winter Haven, FL

    Michael Human · CASA FRESCA REALTY

  22. 1767 Vanilla St — photoNew1Active

    $333,090

    4 bd · 3 ba · 2,039 sqft

    1767 Vanilla St, Winter Haven, FL

    Michael Human · CASA FRESCA REALTY

  23. 219 Terranova Blvd — photoNew31Active

    $428,000

    5 bd · 3 ba · 2,549 sqft

    219 Terranova Blvd, Winter Haven, FL

    Dwight Head · ALLSTATE REALTY SERVICES

  24. 1217 Michelangelo Ln — photo72Active

    $399,999

    4 bd · 4 ba · 2,960 sqft

    1217 Michelangelo Ln, Winter Haven, FL

    Jocelyne Yanez · HOMESMART

12…34

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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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    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 99.9% of asking price

    Sales here are closing essentially at asking. MLS · 138 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 28, 2026

    Median sale price
    $270,000$196,000–$334,500 typical range
    Price per sq. ft.
    $160
    Sales
    175
    Paid in cash
    37.7%

    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
    42 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 (1,217)
    • 34746 (841)
    • 33837 (752)
    • 33896 (574)
    • 33844 (566)
    • 34759 (486)
    • 33897 (441)
    • 33884 (346)

    Cities

    • Kissimmee (2,989)
    • Davenport (1,739)
    • Lakeland (1,164)
    • Haines City (564)
    • Lake Wales (414)
    • Auburndale (249)
    • St. Cloud (235)
    • Orlando (192)