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

Homes with a Pool in Winter Haven, FL

Homes with a Pool in Winter Haven, FL

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24 of 43 Listings
Map

Homes with a Pool in Winter Haven, FL

24 of 43 Listings

  1. 104 13th St SE — photoNew21

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$200,000

2 bd · 2 ba · 1,776 sqft

104 13th St SE, Winter Haven, FL

Chuck Ferdinandsen · CHARLES RUTENBERG REALTY ORLANDO

  • 304 Corso Loop — photo12Active

    $220,000

    3 bd · 2 ba · — sqft

    304 Corso Loop, Winter Haven, FL

    Soreina Del Valle Gonzalez Medina PA · United Realty Group Inc.

  • 333 Lake Howard Dr NW #302B — photoPrice Reduced12Active

    $99,000

    2 bd · 2 ba · 1,030 sqft

    333 Lake Howard Dr NW #302B, Winter Haven, FL

    Karen Myers · UNITED REALTY GROUP INC

  • 333 Lake Howard Drive NW 302B — photo12Active

    $107,000

    2 bd · 2 ba · 1,030 sqft

    333 Lake Howard Drive NW 302B, Winter Haven, FL

    Karen Myers · UNITED REALTY GROUP INC

  • 276 18th St NE — photo27Active

    $279,900

    3 bd · 2 ba · 1,218 sqft

    276 18th St NE, Winter Haven, FL

    Marcelo Garrido · AGENT TRUST REALTY CORPORATION

  • 276 18th Street NE — photo27Active

    $279,900

    3 bd · 2 ba · 1,218 sqft

    276 18th Street NE, Winter Haven, FL

    Marcelo Garrido · AGENT TRUST REALTY CORPORATION

  • 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

  • 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

  • 116 Harbor Dr — photo28Active

    $289,900

    4 bd · 2 ba · 1,476 sqft

    116 Harbor Dr, Winter Haven, FL

    Allison McDaniel · XCELLENCE

  • 116 Harbor Drive — photo28Active

    $289,900

    4 bd · 2 ba · 1,476 sqft

    116 Harbor Drive, Winter Haven, FL

    Allison McDaniel · XCELLENCE

  • 1557 N Lake Shipp Drive SW — photoPrice Reduced55Active

    $264,900

    3 bd · 2 ba · 1,172 sqft

    1557 N Lake Shipp Drive SW, Winter Haven, FL

    Tiffani Kline · HOUSE OF GLASS REAL ESTATE PM

  • 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

  • 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

  • 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

  • 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

  • 235 6th Street NW 307 — photo55Active

    $125,000

    1 bd · 1 ba · 714 sqft

    235 6th Street NW 307, Winter Haven, FL

    Michael Stone · THE STONES REAL ESTATE FIRM

  • 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

  • 2021 Oliver Pl — photoPrice Reduced45Active

    $274,989

    3 bd · 2 ba · 1,507 sqft

    2021 Oliver Pl, Winter Haven, FL

    Ray Colon · TRUE FLORIDA REALTY LLC

  • 2021 Oliver Place — photo45Active

    $274,990

    3 bd · 2 ba · 1,507 sqft

    2021 Oliver Place, Winter Haven, FL

    Ray Colon · TRUE FLORIDA REALTY LLC

  • 706 Avenue I NE — photoPrice Reduced29Active

    $285,000

    3 bd · 2 ba · 1,925 sqft

    706 Avenue I NE, Winter Haven, FL

    Steve Lockhart · LOCKHART & ASSOCIATES INC

  • 706 Avenue I NE — photo12Active

    $295,000

    3 bd · 2 ba · 1,925 sqft

    706 Avenue I NE, Winter Haven, FL

    Steve Lockhart · LOCKHART & ASSOCIATES INC

  • 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

  • 3357 Timberline Road W — photoPrice Reduced15Active

    $265,000

    4 bd · 2 ba · 1,675 sqft

    3357 Timberline Road W, Winter Haven, FL

    Steven Koleno · BEYCOME OF FLORIDA LLC

  • 132 Duval Road — photoPrice Reduced38Active

    $299,500

    2 bd · 2 ba · 1,260 sqft

    132 Duval Road, Winter Haven, FL

    Steven Koleno · BEYCOME OF FLORIDA LLC

  • 12

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

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    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: 2026-09-17 17:50:51 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

    September 2026 · This period is still settling

    Winter Haven 12-month median sale price trend

    Selling at 99.7% of asking price

    Sales here are closing essentially at asking. MLS · 137 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 18, 2026

    Median sale price
    $270,000$207,500–$329,495 typical range
    Price per sq. ft.
    $161
    Sales
    135
    Paid in cash
    36.3%

    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
    48 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.