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Homes with a Pool in Winter Haven, FL — Page 3
87 listings

Homes with a Pool in Winter Haven, FL

Homes with a Pool in Winter Haven, FL

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24 of 87 Listings
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Homes with a Pool in Winter Haven, FL

24 of 87 Listings

  1. 2021 Oliver Pl — photo45Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$274,990

3 bd · 2 ba · 1,507 sqft

2021 Oliver Pl, Winter Haven, FL

Ray Colon · TRUE FLORIDA REALTY LLC

  • 315 Lanceolate Dr — photoPrice Reduced71Active

    $469,000

    3 bd · 2 ba · 2,153 sqft

    315 Lanceolate Dr, Winter Haven, FL

    Veronica Bard · LA ROSA REALTY PRESTIGE

  • 706 Avenue I NE — photo29Active

    $295,000

    3 bd · 2 ba · 1,925 sqft

    706 Avenue I NE, Winter Haven, FL

    Steve Lockhart · LOCKHART & ASSOCIATES INC

  • 41 Greenfield Ct — photoPrice Reduced28Active

    $355,000

    3 bd · 2 ba · 2,054 sqft

    41 Greenfield Ct, Winter Haven, FL

    Steven Smith, PA · LOCKHART & ASSOCIATES INC

  • 1826 6th St SE — photoPrice Reduced41Active

    $400,000

    4 bd · 3 ba · 2,112 sqft

    1826 6th St SE, Winter Haven, FL

    Daphne Manning · LA ROSA REALTY PRESTIGE

  • 328 Hamilton Shores Dr NE — photo80Active

    $765,000

    5 bd · 4 ba · 3,812 sqft

    328 Hamilton Shores Dr NE, Winter Haven, FL

    Michael Stone · THE STONES REAL ESTATE FIRM

  • 1801 Sandhill Ln — photoPrice Reduced65Active

    $574,900

    4 bd · 3 ba · 2,916 sqft

    1801 Sandhill Ln, Winter Haven, FL

    Emily Cassidy · LAND SOURCE REALTY, LLC

  • 136 Lake Mariam Rd SE — photoPrice Reduced55Active

    $385,000

    4 bd · 3 ba · 2,356 sqft

    136 Lake Mariam Rd SE, Winter Haven, FL

    Jill Baird, LLC · KELLER WILLIAMS ADVANTAGE III

  • 3357 Timberline Rd W — photoPrice Reduced15Active

    $265,000

    4 bd · 2 ba · 1,675 sqft

    3357 Timberline Rd W, Winter Haven, FL

    Steven Koleno · BEYCOME OF FLORIDA LLC

  • 445 Talamone Dr — photoPrice Reduced57Active

    $519,990

    5 bd · 3 ba · 2,653 sqft

    445 Talamone Dr, Winter Haven, FL

    Jimmy Aguilar · 3D TEAM REALTY LLC

  • 132 Duval Rd — photoPrice Reduced38Active

    $290,000

    2 bd · 2 ba · 1,260 sqft

    132 Duval Rd, Winter Haven, FL

    Steven Koleno · BEYCOME OF FLORIDA LLC

  • 3097 Buckeye Pointe Dr — photoPrice Reduced59Active

    $430,000

    5 bd · 3 ba · 2,577 sqft

    3097 Buckeye Pointe Dr, Winter Haven, FL

    Desiree Carlson · RE/MAX HERITAGE PROFESSIONALS

  • 250 Brigham Rd NW — photo67Active

    $1,195,000

    5 bd · 6 ba · 3,235 sqft

    250 Brigham Rd NW, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  • 1213 Michelangelo Ln — photoPrice Reduced13Active

    $549,500

    4 bd · 4 ba · 2,894 sqft

    1213 Michelangelo Ln, Winter Haven, FL

    Steven Koleno · BEYCOME OF FLORIDA LLC

  • 1108 Sawgrass Dr — photoPrice Reduced33Active

    $422,999

    2 bd · 2 ba · 1,533 sqft

    1108 Sawgrass Dr, Winter Haven, FL

    Samuel Williams · LA ROSA REALTY CENTRAL FLORIDA LLC

  • 136 Lake Ring Dr — photoPrice Reduced41Active

    $299,900

    3 bd · 2 ba · 1,728 sqft

    136 Lake Ring Dr, Winter Haven, FL

    Lamanda Jones · CENTURY 21 WATSON & MYERS REALTY

  • 100 Alachua Dr — photoPrice Reduced63Active

    $499,900

    3 bd · 2 ba · 2,002 sqft

    100 Alachua Dr, Winter Haven, FL

    Scott Kline · KLINE REAL ESTATE SERVICES

  • 1558 Drexel Ave NE — photoPrice Reduced37Active

    $329,900

    3 bd · 2 ba · 1,160 sqft

    1558 Drexel Ave NE, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  • 314 Terranova Blvd — photoPrice Reduced32Active

    $350,000

    3 bd · 2 ba · 1,884 sqft

    314 Terranova Blvd, Winter Haven, FL

    Jeff Jones · MARK SPAIN REAL ESTATE

  • listing photoPrice Reduced28Active

    $265,000

    2 bd · 1 ba · 2,142 sqft

    Address withheld · Winter Haven, FL

    Marcia Rains - Nadal, Mrs · YELLOWFIN REALTY

  • 237 Mclean Point — photo86Active

    $720,000

    4 bd · 4 ba · 2,961 sqft

    237 Mclean Point, Winter Haven, FL

    Luis Perez Garcia · EXP Realty LLC

  • 5365 Hogan Ln — photo100Active

    $599,900

    3 bd · 2 ba · 2,591 sqft

    5365 Hogan Ln, Winter Haven, FL

    Brad Kirwan · GLOBAL LIFESTYLE LLC

  • 2935 Plantation Rd — photoPrice Reduced53Active

    $563,900

    4 bd · 4 ba · 2,724 sqft

    2935 Plantation Rd, Winter Haven, FL

    Lovett Johnson · LBJ REALTY AND ASSOCIATES LLC

  • 1450 W Lake Cannon Dr NW — photoPrice Reduced15Active

    $299,000

    5 bd · 2 ba · 4,053 sqft

    1450 W Lake Cannon Dr NW, Winter Haven, FL

    Veronica Davis · EXP REALTY LLC

  • 1234
    Realty.com

    L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Listing data & MLS disclosures

    MIAMI REALTORS MLS
    The multiple listing information is provided by MIAMI Association of Realtors® from a copyrighted compilation of listings. The compilation of listings and each individual listingare ©2026 MIAMI Association of Realtors®. All Rights Reserved.
    The information provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Last Updated: 2026-04-04 00:01:06 UTC
    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

    August 2026

    Winter Haven 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 187 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 31, 2026

    Median sale price
    $280,000$204,200–$384,975 typical range
    Price per sq. ft.
    $154
    Sales
    290
    Paid in cash
    45.2%

    Homes on the market · MLS, as of Aug 31, 2026

    Median days on market
    34 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    -5.1%