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Homes with a Pool in Winter Haven, FL — Page 2
86 listings

Homes with a Pool in Winter Haven, FL

Homes with a Pool in Winter Haven, FL

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24 of 86 Listings
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Homes with a Pool in Winter Haven, FL

24 of 86 Listings

  1. 318 Hamilton Shores Dr NE — photoPrice Reduced58

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$533,000

4 bd · 2 ba · 2,806 sqft

318 Hamilton Shores Dr NE, Winter Haven, FL

Dani Borow · KELLER WILLIAMS REALTY

  • 215 Santa Rosa Dr — photoPrice Reduced25Active

    $304,900

    4 bd · 2 ba · 2,355 sqft

    215 Santa Rosa Dr, Winter Haven, FL

    Cynthia Fernandez · XCLUSIVE HOMES LLC

  • 25 Lakewood Cswy — photo52Active

    $849,900

    5 bd · 4 ba · 4,108 sqft

    25 Lakewood Cswy, Winter Haven, FL

    Melissa Meyer · KEENE'S POINTE REALTY

  • 3640 Crump Rd — photo63Active

    $1,399,900

    4 bd · 3 ba · 3,309 sqft

    3640 Crump Rd, Winter Haven, FL

    Amy Reynolds · LOCKHART & ASSOCIATES INC

  • 153 Browning Cir — photo48Active

    $269,000

    3 bd · 2 ba · 1,144 sqft

    153 Browning Cir, Winter Haven, FL

    Kimberly Jones · RE/MAX HERITAGE PROFESSIONALS

  • 9469 Waterford Oaks Dr — photoPrice Reduced59Active

    $789,900

    4 bd · 3 ba · 3,648 sqft

    9469 Waterford Oaks Dr, Winter Haven, FL

    Zach Zehnder · KELLER WILLIAMS ST PETE REALTY

  • 5888 Windridge Dr — photo30Active

    $330,000

    4 bd · 3 ba · 2,836 sqft

    5888 Windridge Dr, Winter Haven, FL

    Danique Haywood · MARK SPAIN REAL ESTATE

  • 506 Clayton Cir — photoPrice Reduced26Active

    $309,900

    4 bd · 3 ba · 2,004 sqft

    506 Clayton Cir, Winter Haven, FL

    Anne Halbert · LIVE FLORIDA REALTY

  • 280 Santa Rosa Dr — photoPrice Reduced44Active

    $415,000

    3 bd · 2 ba · 2,251 sqft

    280 Santa Rosa Dr, Winter Haven, FL

    Ashley James · KELLER WILLIAMS REALTY SMART 1

  • 1019 W Lake Eloise Ter — photoPrice Reduced56Active

    $880,000

    2 bd · 3 ba · 2,768 sqft

    1019 W Lake Eloise Ter, Winter Haven, FL

    Ashley Adams · HOGAN & ASSOCIATES REAL ESTATE FIRM

  • 3035 Buckeye Pointe Dr — photo17Active

    $369,900

    4 bd · 3 ba · 2,070 sqft

    3035 Buckeye Pointe Dr, Winter Haven, FL

    Wil Sanders · EXP REALTY LLC

  • 205 Thomas Ct — photoPrice Reduced50Active

    $435,000

    3 bd · 3 ba · 2,352 sqft

    205 Thomas Ct, Winter Haven, FL

    Stephanie Mayo · REGAL REAL ESTATE LLC

  • 116 Harbor Dr — photo28Active

    $289,900

    4 bd · 2 ba · 1,476 sqft

    116 Harbor Dr, Winter Haven, FL

    Allison McDaniel · XCELLENCE

  • 228 W Lake Ina Dr — photoPrice Reduced64Active

    $389,000

    3 bd · 4 ba · 1,675 sqft

    228 W Lake Ina Dr, Winter Haven, FL

    Casandra Vann · KELLER WILLIAMS REALTY

  • 1557 N Lake Shipp Dr SW — photoPrice Reduced55Active

    $264,900

    3 bd · 2 ba · 1,172 sqft

    1557 N Lake Shipp Dr SW, Winter Haven, FL

    Tiffani Kline · HOUSE OF GLASS REAL ESTATE PM

  • 408 Coleman Dr — photoPrice Reduced32Active

    $389,900

    4 bd · 2 ba · 2,420 sqft

    408 Coleman Dr, Winter Haven, FL

    Michael Mcgee · MAINSTAY BROKERAGE LLC

  • 4040 Palma Ceia Cir — photo100Active

    $749,000

    3 bd · 4 ba · 2,493 sqft

    4040 Palma Ceia Cir, Winter Haven, FL

    Deanna Stone · THE STONES REAL ESTATE FIRM

  • 5009 Strada Dr — photo48Active

    $425,000

    4 bd · 3 ba · 2,434 sqft

    5009 Strada Dr, Winter Haven, FL

    Florentino Beltran · KELLER WILLIAMS ADVANTAGE 2 REALTY

  • 144 Waterside Cir — photoPrice Reduced37Active

    $299,000

    3 bd · 2 ba · 1,847 sqft

    144 Waterside Cir, Winter Haven, FL

    Ythamarie Rosario · KELLER WILLIAMS ADVANTAGE III

  • 1755 Beth Ln — photo42Active

    $435,000

    3 bd · 2 ba · 2,702 sqft

    1755 Beth Ln, Winter Haven, FL

    Joni Reiter · COLDWELL BANKER REALTY

  • 3334 Avenue J NW — photoPrice Reduced45Active

    $249,765

    3 bd · 2 ba · 1,473 sqft

    3334 Avenue J NW, Winter Haven, FL

    Nicki Salas Fuentes · ELEVE REAL ESTATE LLC

  • 906 Avenue M SE — photoPrice Reduced35Active

    $349,900

    3 bd · 2 ba · 1,890 sqft

    906 Avenue M SE, Winter Haven, FL

    Joleigh Nolen · COLDWELL BANKER REALTY

  • 235 6th St NW #307 — photo55Active

    $125,000

    1 bd · 1 ba · 714 sqft

    235 6th St NW #307, Winter Haven, FL

    Michael Stone · THE STONES REAL ESTATE FIRM

  • 6704 Winterset Gardens Rd — photoPrice Reduced69Active

    $399,000

    3 bd · 2 ba · 2,418 sqft

    6704 Winterset Gardens Rd, Winter Haven, FL

    Rachel Santos · WEICHERT REALTORS HALLMARK PRO

  • 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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    Your local brokerage

    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

    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%