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3 bedsNew constructionWith a pool
Homes with a Pool in Winter Garden, FL — Page 3
95 listings

Homes with a Pool in Winter Garden, FL

Homes with a Pool in Winter Garden, FL

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24 of 95 Listings
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Homes with a Pool in Winter Garden, FL

24 of 95 Listings

  1. 2139 Tillman Ave — photoPrice Reduced48

Your Winter Garden agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLCCall Veronica
Active

$840,000

4 bd · 4 ba · 3,078 sqft

2139 Tillman Ave, Winter Garden, FL

Marti Purdy · MARTI PURDY PROPERTIES INC

  • 16736 Gullfloss Ter — photoPrice Reduced41Active

    $765,000

    4 bd · 4 ba · 2,806 sqft

    16736 Gullfloss Ter, Winter Garden, FL

    Frank Benevento · COLDWELL BANKER REALTY

  • 14931 Lebeau Loop — photo87Active

    $799,000

    4 bd · 4 ba · 2,832 sqft

    14931 Lebeau Loop, Winter Garden, FL

    Maqueli Gewehr · WRA BUSINESS & REAL ESTATE

  • 2010 Boss Hewett St — photo94Active

    $1,500,000

    5 bd · 4 ba · 3,781 sqft

    2010 Boss Hewett St, Winter Garden, FL

    Vilmari Caraballo · RE/MAX ASSURED

  • 12248 Encore at Ovation Way — photoPrice Reduced51Active

    $675,000

    4 bd · 3 ba · 2,346 sqft

    12248 Encore at Ovation Way, Winter Garden, FL

    Abraham Ash · Coldwell Banker Realty

  • 8937 Lakeshore Pointe Dr — photoPrice ReducedOpen house Sat, Oct 10 · 1:00 PM39Active

    $575,000

    3 bd · 3 ba · 2,052 sqft

    8937 Lakeshore Pointe Dr, Winter Garden, FL

    Karen Ledet · EXP REALTY LLC

  • 16044 Citrus Knoll Dr — photoPrice Reduced90Active

    $1,020,000

    5 bd · 4 ba · 3,617 sqft

    16044 Citrus Knoll Dr, Winter Garden, FL

    Kaitlin Sidders · HOGAN REALTY GROUP INC

  • 13175 Sunny Retreat Ln — photoPrice Reduced43Active

    $755,000

    3 bd · 2 ba · 2,054 sqft

    13175 Sunny Retreat Ln, Winter Garden, FL

    Sean Popat · BUYER REBATES REALTY

  • 14711 Winter Stay Dr — photoPrice Reduced89Active

    $835,000

    4 bd · 3 ba · 2,662 sqft

    14711 Winter Stay Dr, Winter Garden, FL

    Glauco Pochine · THE FLORIDA LOUNGE REALTY LLC

  • 14312 Sunbridge Cir — photoPrice Reduced51Active

    $1,060,000

    5 bd · 4 ba · 4,225 sqft

    14312 Sunbridge Cir, Winter Garden, FL

    Karen Vasquez Rodriguez · REALTY ONE GROUP MAGIC CITY

  • 214 S Woodland St — photo1Active

    $800,000

    4 bd · 2 ba · 2,868 sqft

    214 S Woodland St, Winter Garden, FL

    Nicole Prince · LPT REALTY, LLC

  • 13092 Sunrise Harvest Dr — photoPrice Reduced44Active

    $845,000

    4 bd · 4 ba · 2,993 sqft

    13092 Sunrise Harvest Dr, Winter Garden, FL

    David Bollet · REDFIN CORPORATION

  • 15741 Sweet Lemon Way — photoPrice Reduced57Active

    $1,080,000

    5 bd · 5 ba · 3,624 sqft

    15741 Sweet Lemon Way, Winter Garden, FL

    Cristiane Carneiro Spindola Rocha Lima · WRA BUSINESS & REAL ESTATE

  • 925 Easley Ave — photoPrice Reduced47Active

    $1,075,000

    4 bd · 4 ba · 2,667 sqft

    925 Easley Ave, Winter Garden, FL

    Matthew McKee · COMPASS FLORIDA LLC

  • 13856 Glynshel Dr — photoOpen house Sun, Oct 11 · 12:00 PM46Active

    $850,000

    5 bd · 4 ba · 3,538 sqft

    13856 Glynshel Dr, Winter Garden, FL

    Mary Dees · CHOICEPOINTE REALTY, INC.

  • 1812 Lake Roberts Landing Dr — photo69Active

    $1,200,000

    6 bd · 4 ba · 4,247 sqft

    1812 Lake Roberts Landing Dr, Winter Garden, FL

    Alexis Jacobsen · EXP REALTY LLC

  • 14501 Grove Resort Ave #3425 — photo21Active

    $480,000

    2 bd · 2 ba · 1,265 sqft

    14501 Grove Resort Ave #3425, Winter Garden, FL

    Jorge Kupferman · MIAMI LIFE REALTY LLC

  • 14411 Hampshire Bay Cir — photoPrice Reduced46Active

    $870,000

    4 bd · 5 ba · 4,010 sqft

    14411 Hampshire Bay Cir, Winter Garden, FL

    Julie Bettosini, PA · STOCKWORTH REALTY GROUP

  • 20 E Division St — photoPrice Reduced37Active

    $995,000

    4 bd · 3 ba · 2,729 sqft

    20 E Division St, Winter Garden, FL

    Liz Boyce · CHARLES RUTENBERG REALTY ORLANDO

  • 15499 Shorebird Lane — photoPrice Reduced43Active

    $2,380,000

    4 bd · 6 ba · — sqft

    15499 Shorebird Lane, Winter Garden, FL

    Camila Tinjaca Pino · Compass Florida, LLC

  • 9189 Busaco Park Way — photoPrice Reduced74Active

    $1,198,000

    4 bd · 4 ba · 3,424 sqft

    9189 Busaco Park Way, Winter Garden, FL

    Sulamit Sanchez · COLDWELL BANKER REALTY

  • 15505 Shorebird Ln — photo87Active

    $2,500,000

    6 bd · 7 ba · 5,287 sqft

    15505 Shorebird Ln, Winter Garden, FL

    Joao Freitas De Souza Freitas, Jr · WRA BUSINESS & REAL ESTATE

  • 14501 Grove 3425 — photoPrice Reduced24Active

    $420,000

    2 bd · 2 ba · — sqft

    14501 Grove 3425, Winter Garden, FL

    Mailliw Morales Mollegas · Miami Life Realty LLC

  • 9110 Morgana Ct — photoPrice Reduced77Active

    $1,999,000

    5 bd · 5 ba · 4,661 sqft

    9110 Morgana Ct, Winter Garden, FL

    Alie Gattis · MAINFRAME REAL ESTATE

  • 1234

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    Your Winter Garden agent

    VF

    Veronica Figueroa

    The Figueroa Team LLC. eXp Realty, LLC

    The Figueroa Team LLC. eXp Realty, LLCCall Veronica

    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: 2026-09-26 20:59:22 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 Garden, FL community profile

    Population
    50,261
    Median income
    $102,195
    Housing units
    18,962
    People per sq. mi.
    562.2
    Area
    89.4 sq. mi.

    Source: HJN community data

    Winter Garden housing market

    September 2026 · This period is still settling

    Winter Garden 12-month median sale price trend

    Selling at 98.1% of asking price

    Buyers here are paying below asking. MLS · 221 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 23, 2026

    Median sale price
    $632,500$500,125–$1,055,625 typical range
    Price per sq. ft.
    $259
    Sales
    194
    Paid in cash
    39.7%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

    Median list price
    $565,000
    Homes for sale
    795
    Median days on market
    37 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    11.2%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

    Median home size
    2,211 sq. ft.