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3 bedsNew constructionWith a pool
Homes with a Pool in Winter Haven, FL
98 listings

Homes with a Pool in Winter Haven, FL

Homes with a Pool in Winter Haven, FL

Show Map
24 of 98 Listings
Map

Homes with a Pool in Winter Haven, FL

24 of 98 Listings

  1. 1151 Carefree Cove Dr — photo24

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$399,000

3 bd · 2 ba · 1,734 sqft

1151 Carefree Cove Dr, Winter Haven, FL

Jonathan Minerick · HOMECOIN.COM

  • 138 Saint Kitts Cir — photo32Active

    $259,000

    3 bd · 2 ba · 1,248 sqft

    138 Saint Kitts Cir, Winter Haven, FL

    Erik McGinnis · HOMEVEST REALTY

  • 1010 Edgewater Dr — photoOpen house Sun, Nov 8 · 11:00 AM48Active

    $795,000

    4 bd · 3 ba · 2,346 sqft

    1010 Edgewater Dr, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  • 6052 Kaley Dr — photoNew56Active

    $375,000

    4 bd · 3 ba · 2,200 sqft

    6052 Kaley Dr, Winter Haven, FL

    Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS

  • 4462 Emerald Palms Ln — photo47Active

    $975,000

    4 bd · 3 ba · 2,825 sqft

    4462 Emerald Palms Ln, Winter Haven, FL

    Stephen Hachey · FLAT FEE MLS REALTY

  • 4925 Cypress Gardens Rd #97 — photo27Active

    $180,000

    2 bd · 2 ba · 1,000 sqft

    4925 Cypress Gardens Rd #97, Winter Haven, FL

    Austin Henry · CENTURY 21 MYERS REALTY LAKE WALES

  • 725 Heritage Dr NE — photo53Active

    $560,000

    4 bd · 3 ba · 3,114 sqft

    725 Heritage Dr NE, Winter Haven, FL

    Erin Floyd · COLDWELL BANKER REALTY

  • 888 Twin Oaks Ln — photo100Active

    $2,000,000

    5 bd · 5 ba · 4,565 sqft

    888 Twin Oaks Ln, Winter Haven, FL

    Brandy Duncan · COLDWELL BANKER REALTY

  • 251 Lake Link — photoOpen house Sat, Oct 31 · 11:00 AM51Active

    $579,900

    3 bd · 2 ba · 2,107 sqft

    251 Lake Link, Winter Haven, FL

    Zachary Lay LLC · WATSON REALTY CORP.

  • 593 Terranova Cir — photo70Active

    $359,000

    3 bd · 2 ba · 1,728 sqft

    593 Terranova Cir, Winter Haven, FL

    Noor Masri, PA · LA ROSA REALTY PREMIER LLC

  • 260 Greenfield Rd — photo54Active

    $349,900

    3 bd · 2 ba · 1,947 sqft

    260 Greenfield Rd, Winter Haven, FL

    Kayly Malinas, PA · JOHN WOOD REALTY, INC.

  • 11 Lake Link Dr SE — photo71Active

    $750,000

    6 bd · 3 ba · 3,438 sqft

    11 Lake Link Dr SE, Winter Haven, FL

    Michael Stone · THE STONES REAL ESTATE FIRM

  • 114 Belmont Dr — photo43Active

    $459,000

    4 bd · 2 ba · 2,069 sqft

    114 Belmont Dr, Winter Haven, FL

    Mark Bouchard · MLB FREEDOM DESTINATIONS

  • 1921 Manor Cir SE — photo88Active

    $1,295,000

    3 bd · 3 ba · 2,375 sqft

    1921 Manor Cir SE, Winter Haven, FL

    Dee Norris · NEXTHOME NORRIS & COMPANY REAL

  • 2022 Kapree Ct — photo25Active

    $515,000

    5 bd · 3 ba · 2,685 sqft

    2022 Kapree Ct, Winter Haven, FL

    Jerome Baker · BAKER REAL ESTATE PRO. GR LLC

  • 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

  • 669 Sarner Pass Way — photo54Active

    $625,000

    5 bd · 3 ba · 3,016 sqft

    669 Sarner Pass Way, Winter Haven, FL

    Miguel Shellie · MARK SPAIN REAL ESTATE

  • 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

  • 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

  • 714 Avenue O SE — photoPrice Reduced33Active

    $329,900

    5 bd · 2 ba · 2,104 sqft

    714 Avenue O SE, Winter Haven, FL

    Ileana Perez · HOUWZER INC

  • 104 13th St SE — photoPrice Reduced21Active

    $197,000

    2 bd · 2 ba · 1,776 sqft

    104 13th St SE, Winter Haven, FL

    Chuck Ferdinandsen · CHARLES RUTENBERG REALTY ORLANDO

  • 10 W Lake Hamilton Cir — photo36Active

    $485,000

    4 bd · 2 ba · 2,400 sqft

    10 W Lake Hamilton Cir, Winter Haven, FL

    John Keller, III · JACK KELLER INC

  • 5809 Windridge Dr — photoPrice ReducedOpen house Sat, Oct 31 · 10:00 AM57Active

    $349,000

    4 bd · 3 ba · 2,836 sqft

    5809 Windridge Dr, Winter Haven, FL

    Kimberly Davis · CROSBY & ASSOCIATES, INC.

  • 13 Bogey Dr — photo61Active

    $1,750,000

    4 bd · 4 ba · 3,476 sqft

    13 Bogey Dr, Winter Haven, FL

    Cathy Kluytenaar · THE K TEAM REAL ESTATE SERVICES LLC

  • 12…5

    Explore Winter Haven homes

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    • Homes Under $100K
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    By type

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    • Homes with a Pool
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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 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.