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3 bedsNew constructionWith a pool
Single-Family Homes in Winter Haven, FL
606 listings

Single-Family Homes in Winter Haven, FL

Single-Family Homes in Winter Haven, FL

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24 of 606 Listings
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Single-Family Homes in Winter Haven, FL

24 of 606 Listings

  1. 420 Avenue U NE — photoNew39

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$155,900

3 bd · 2 ba · 1,216 sqft

420 Avenue U NE, Winter Haven, FL

Twanna Dewdney · LA ROSA REALTY PRESTIGE

  • 183 Osprey Heights Dr — photo27Active

    $189,900

    3 bd · 2 ba · 1,426 sqft

    183 Osprey Heights Dr, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  • 732 Bayside Blvd — photoNew9Active

    $281,900

    3 bd · 2 ba · 1,486 sqft

    732 Bayside Blvd, Winter Haven, FL

    George Lindsey, III · CAMBRIDGE REALTY OF CENTRAL FL

  • 504 Ituna Cir — photoNew4Active

    $331,020

    4 bd · 2 ba · 1,715 sqft

    504 Ituna Cir, Winter Haven, FL

    George Lindsey, III · CAMBRIDGE REALTY OF CENTRAL FL

  • 1831 Carnostie Rd — photoNewOpen house Fri, Oct 16 · 1:00 PM34Active

    $279,000

    4 bd · 2 ba · 1,680 sqft

    1831 Carnostie Rd, Winter Haven, FL

    Jane Rana · CHARLES RUTENBERG REALTY ORLANDO

  • 736 Bayside Blvd — photoNew4Active

    $279,900

    3 bd · 2 ba · 1,479 sqft

    736 Bayside Blvd, Winter Haven, FL

    George Lindsey, III · CAMBRIDGE REALTY OF CENTRAL FL

  • 6159 Coronari Ln — photoNew37Active

    $336,990

    5 bd · 3 ba · 2,447 sqft

    6159 Coronari Ln, Winter Haven, FL

    Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

  • 640 Avenue I NW — photo10Active

    $325,000

    3 bd · 3 ba · 3,753 sqft

    640 Avenue I NW, Winter Haven, FL

    Lisa Deese · TOWN & COUNTRY REAL ESTATE

  • 1020 W Lake Hamilton Dr — photoNew56Active

    $710,000

    4 bd · 3 ba · 3,428 sqft

    1020 W Lake Hamilton Dr, Winter Haven, FL

    Tony Insua, Jr · LOCKHART & ASSOCIATES INC

  • 2433 Avenue F NW — photoNew12Active

    $294,997

    3 bd · 2 ba · 1,270 sqft

    2433 Avenue F NW, Winter Haven, FL

    Adan Ordonez · ADAN INVESTMENTS REAL ESTATE GROUP, PLLC

  • 2415 Brassie Ct — photoNew41Active

    $279,000

    3 bd · 2 ba · 1,629 sqft

    2415 Brassie Ct, Winter Haven, FL

    Eileen Belanger · CENTURY 21 MYERS REALTY LAKE WALES

  • 444 Avenue I SE — photo32Active

    $119,000

    2 bd · 2 ba · 1,036 sqft

    444 Avenue I SE, Winter Haven, FL

    Katherine Hatton · SOUTH CEDAR REAL ESTATE, INC

  • 828 30th St NW — photo24Active

    $215,000

    3 bd · 2 ba · 1,100 sqft

    828 30th St NW, Winter Haven, FL

    Catherine Nolan · HOUSEWELL.COM REALTY OF FLORIDA LLC

  • 1075 8th St NW — photo52Active

    $480,000

    4 bd · 3 ba · 1,985 sqft

    1075 8th St NW, Winter Haven, FL

    Jim Knetsch · LPT REALTY, LLC

  • 6216 Pinehurst Loop — photo68Active

    $429,000

    3 bd · 2 ba · 2,045 sqft

    6216 Pinehurst Loop, Winter Haven, FL

    Lori Raath · LAKE ASHTON REALTY INC.

  • 218 6th Jpv St — photo25Active

    $255,000

    3 bd · 2 ba · 1,228 sqft

    218 6th Jpv St, Winter Haven, FL

    Renee Butler · BROKERS REALTY OF CENTRAL FLOR

  • 2426 6th St NE — photo46Active

    $240,000

    3 bd · 2 ba · 1,447 sqft

    2426 6th St NE, Winter Haven, FL

    Frankie Eizere · RE/MAX HERITAGE PROFESSIONALS

  • 1097 Carefree Cove Dr — photoOpen house Sat, Oct 17 · 11:00 AM50Active

    $319,900

    3 bd · 2 ba · 1,484 sqft

    1097 Carefree Cove Dr, Winter Haven, FL

    Frankie Eizere · RE/MAX HERITAGE PROFESSIONALS

  • 1331 Haines Dr — photo36Active

    $249,000

    3 bd · 2 ba · 1,471 sqft

    1331 Haines Dr, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  • 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

  • 1048 Luke Ave — photo1Active

    $314,990

    4 bd · 2 ba · 1,938 sqft

    1048 Luke Ave, Winter Haven, FL

    Nancy Pruitt, PA · OLYMPUS EXECUTIVE REALTY INC

  • 1056 Luke Ave — photo1Active

    $309,990

    4 bd · 2 ba · 1,938 sqft

    1056 Luke Ave, Winter Haven, FL

    Nancy Pruitt, PA · OLYMPUS EXECUTIVE REALTY INC

  • 5288 Green Dr — photo64Active

    $314,000

    3 bd · 2 ba · 1,847 sqft

    5288 Green Dr, Winter Haven, FL

    Pat Pearson · VIEWPOINT VALUE REALTY

  • 714 Avenue O SE — photo33Active

    $359,900

    5 bd · 2 ba · 2,104 sqft

    714 Avenue O SE, Winter Haven, FL

    Ileana Perez · HOUWZER INC

  • 12…26

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    TO

    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 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.