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

Homes with a Pool in Winter Haven, FL

Homes with a Pool in Winter Haven, FL

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24 of 96 Listings
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Homes with a Pool in Winter Haven, FL

24 of 96 Listings

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Thomas O'Leary

Realty.com

Lic. #BK3453168

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  1. 9457 Waterford Oaks Dr — photo24Active

    $710,000

    3 bd · 3 ba · 3,292 sqft

    9457 Waterford Oaks Dr, Winter Haven, FL

    Amy Riggleman · SIGNATURE PROPERTIES OF CENTRAL FLORIDA LLC

  2. 1151 Carefree Cove Dr — photo24Active

    $399,000

    3 bd · 2 ba · 1,734 sqft

    1151 Carefree Cove Dr, Winter Haven, FL

    Jonathan Minerick · HOMECOIN.COM

  3. 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

  4. 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

  5. 6052 Kaley Dr — photoOpen house Sat, Nov 7 · 11:00 AM56Active

    $375,000

    4 bd · 3 ba · 2,200 sqft

    6052 Kaley Dr, Winter Haven, FL

    Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS

  6. 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

  7. 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

  8. 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

  9. 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

  10. 251 Lake Link — photo51Active

    $579,900

    3 bd · 2 ba · 2,107 sqft

    251 Lake Link, Winter Haven, FL

    Zachary Lay LLC · WATSON REALTY CORP.

  11. 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

  12. 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.

  13. 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

  14. 114 Belmont Dr — photo43Active

    $459,000

    4 bd · 2 ba · 2,069 sqft

    114 Belmont Dr, Winter Haven, FL

    Mark Bouchard · MLB FREEDOM DESTINATIONS

  15. 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

  16. 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

  17. 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

  18. 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

  19. 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

  20. 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

  21. 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

  22. 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

  23. 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

  24. 5809 Windridge Dr — photoPrice Reduced57Active

    $349,000

    4 bd · 3 ba · 2,836 sqft

    5809 Windridge Dr, Winter Haven, FL

    Kimberly Davis · CROSBY & ASSOCIATES, INC.

12…4

About Homes with a Pool in Winter Haven, FL

Homes with a Pool in Winter Haven, FL: 96 active listings as of November 1, 2026, 15:12 UTC.

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    Thomas O'Leary

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    Lic. #BK3453168

    Call Thomas

    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

    October 2026 · This period is still settling

    Winter Haven 12-month median sale price trend

    Selling at 99.8% of asking price

    Sales here are closing essentially at asking. MLS · 84 sales · as of Oct 23, 2026

    Homes that sold · County records, as of Oct 9, 2026

    Median sale price
    $293,750$222,500–$2,063,500 typical range
    Price per sq. ft.
    $171
    Sales
    106
    Paid in cash
    48.1%

    Homes on the market · MLS, as of Oct 18, 2026–Oct 23, 2026

    Median list price
    $295,000
    Homes for sale
    713
    Median days on market
    43 days

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

    Year-over-year
    5.4%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

    Median home size
    1,632 sq. ft.