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3 bedsNew constructionWith a pool
4 Bedroom Homes in Winter Haven, FL
215 listings

4 Bedroom Homes in Winter Haven, FL

4 Bedroom Homes in Winter Haven, FL

Show Map
24 of 215 Listings
Map

4 Bedroom Homes in Winter Haven, FL

24 of 215 Listings

  1. 4956 Jackson St — photo38Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$295,000

4 bd · 2 ba · 1,876 sqft

4956 Jackson St, Winter Haven, FL

Anthony Medina · KELLER WILLIAMS REALTY SMART 1

  • 3944 Giorgio Dr — photo7Active

    $275,000

    4 bd · 2 ba · 1,607 sqft

    3944 Giorgio Dr, Winter Haven, FL

    Bryan Sumner · MERITAGE HOMES OF FL REALTY

  • 997 Harold Pass — photo34Active

    $299,999

    4 bd · 3 ba · 1,933 sqft

    997 Harold Pass, Winter Haven, FL

    Andrea Heck · KELLER WILLIAMS TAMPA CENTRAL

  • 829 Sun Ridge Village Dr — photo32Active

    $369,900

    4 bd · 3 ba · 3,020 sqft

    829 Sun Ridge Village Dr, Winter Haven, FL

    Robert Salmons · ENTERA REALTY LLC

  • 114 Belmont Dr — photo42Active

    $459,000

    4 bd · 2 ba · 2,069 sqft

    114 Belmont Dr, Winter Haven, FL

    Mark Bouchard · MLB FREEDOM DESTINATIONS

  • 5365 San Pietro Dr — photo1Active

    $319,999

    4 bd · 3 ba · 2,039 sqft

    5365 San Pietro Dr, Winter Haven, FL

    Michael Human · CASA FRESCA REALTY

  • 138 Grove Branch Rd — photo46Active

    $289,000

    4 bd · 2 ba · 1,851 sqft

    138 Grove Branch Rd, Winter Haven, FL

    Michael Stone · THE STONES REAL ESTATE FIRM

  • 1764 Vanilla St — photo1Active

    $410,620

    4 bd · 3 ba · 2,292 sqft

    1764 Vanilla St, Winter Haven, FL

    Michael Human · CASA FRESCA REALTY

  • 1767 Vanilla St — photo1Active

    $333,090

    4 bd · 3 ba · 2,039 sqft

    1767 Vanilla St, Winter Haven, FL

    Michael Human · CASA FRESCA REALTY

  • 703 Avenue L SE — photo21Active

    $278,000

    4 bd · 2 ba · 1,830 sqft

    703 Avenue L SE, Winter Haven, FL

    Sandra Wyhnanskyj, PA · OLYMPUS EXECUTIVE REALTY INC

  • 128 Lagoon Rd — photo24Active

    $340,000

    4 bd · 2 ba · 1,701 sqft

    128 Lagoon Rd, Winter Haven, FL

    Marina Navia, P.A · COLDWELL BANKER REALTY

  • 1217 Michelangelo Ln — photo72Active

    $399,999

    4 bd · 4 ba · 2,960 sqft

    1217 Michelangelo Ln, Winter Haven, FL

    Jocelyne Yanez · HOMESMART

  • 1127 Seedorf Dr — photo48Active

    $319,990

    4 bd · 2 ba · 2,004 sqft

    1127 Seedorf Dr, Winter Haven, FL

    Juan Acevedo · FORTUNE INTERNATIONAL REALTY

  • 221 Avenue P NW — photo49Active

    $327,700

    4 bd · 2 ba · 1,830 sqft

    221 Avenue P NW, Winter Haven, FL

    Madeline Rivera · INNOVATION GROUP REALTY LLC

  • 1652 Lemon Ave — photo19Active

    $380,000

    4 bd · 3 ba · 2,509 sqft

    1652 Lemon Ave, Winter Haven, FL

    Danny Chandler, Jr · COLDWELL BANKER REALTY

  • 7380 Bent Grass Dr — photo65Active

    $559,900

    4 bd · 3 ba · 2,775 sqft

    7380 Bent Grass Dr, Winter Haven, FL

    Twanna Dewdney · LA ROSA REALTY PRESTIGE

  • 6060 Navona Way — photo33Active

    $305,990

    4 bd · 3 ba · 1,866 sqft

    6060 Navona Way, Winter Haven, FL

    Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

  • 2771 Adeline Ave — photo1Active

    $296,990

    4 bd · 2 ba · 1,574 sqft

    2771 Adeline Ave, Winter Haven, FL

    Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

  • 2767 Adeline Ave — photo1Active

    $298,990

    4 bd · 2 ba · 1,574 sqft

    2767 Adeline Ave, Winter Haven, FL

    Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

  • 504 Ituna Cir — photoPrice Reduced4Active

    $319,900

    4 bd · 2 ba · 1,715 sqft

    504 Ituna Cir, Winter Haven, FL

    George Lindsey, III · CAMBRIDGE REALTY OF CENTRAL FL

  • 1831 Carnostie Rd — photo34Active

    $279,000

    4 bd · 2 ba · 1,680 sqft

    1831 Carnostie Rd, Winter Haven, FL

    Jane Rana · CHARLES RUTENBERG REALTY ORLANDO

  • 1020 W Lake Hamilton Dr — photo56Active

    $710,000

    4 bd · 3 ba · 3,428 sqft

    1020 W Lake Hamilton Dr, Winter Haven, FL

    Tony Insua, Jr · LOCKHART & ASSOCIATES INC

  • 1075 8th St NW — photo51Active

    $480,000

    4 bd · 3 ba · 1,985 sqft

    1075 8th St NW, Winter Haven, FL

    Jim Knetsch · LPT REALTY, LLC

  • 1044 Luke Ave — photo26Active

    $309,990

    4 bd · 2 ba · 1,758 sqft

    1044 Luke Ave, Winter Haven, FL

    Nancy Pruitt, PA · OLYMPUS EXECUTIVE REALTY INC

  • 12…9

    Explore Winter Haven homes

    By price

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    By type

    • Single-Family Homes
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    By feature

    • New Construction Homes
    • Homes with a Pool
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    • 55+ Community Homes
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    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Listing data & MLS disclosures

    Stellar MLS
    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.

    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 30, 2026

    Median sale price
    $270,000$195,000–$332,030 typical range
    Price per sq. ft.
    $159
    Sales
    200
    Paid in cash
    38.0%

    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.