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Start here

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3 bedsNew constructionWith a pool
55+ Community Homes in Winter Garden, FL
13 listings

55+ Community Homes in Winter Garden, FL

55+ Community Homes in Winter Garden, FL

Show Map
13 Listings
Map

55+ Community Homes in Winter Garden, FL

13 Listings

  1. 15066 Canopy Cover Dr — photo63Active

Your Winter Garden agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLCCall Veronica

$967,500

3 bd · 4 ba · 2,955 sqft

15066 Canopy Cover Dr, Winter Garden, FL

Eileen Winfrey · IAD REAL ESTATE

  • 15193 Aqua Sol Ln — photo35Active

    $459,900

    3 bd · 2 ba · 1,579 sqft

    15193 Aqua Sol Ln, Winter Garden, FL

    Eliane Hoffmann · WRA BUSINESS & REAL ESTATE

  • 1606 Beulah Rd — photo27Active

    $409,000

    3 bd · 2 ba · 1,539 sqft

    1606 Beulah Rd, Winter Garden, FL

    Saad Mrini · WEICHERT REALTORS HALLMARK PRO

  • 13418 Princess St — photoPrice Reduced21Active

    $425,000

    2 bd · 2 ba · 1,574 sqft

    13418 Princess St, Winter Garden, FL

    Nader Alhawamdeh · TURBO REAL ESTATE GROUP LLC

  • 13056 Sandcastle Drive — photoPrice Reduced22Active

    $699,430

    2 bd · 2 ba · 1,889 sqft

    13056 Sandcastle Drive, Winter Garden, FL

    Adrienne Escott · PULTE REALTY OF NORTH FLORIDA LLC

  • 13360 Sunny Retreat Ln — photo73Active

    $595,000

    3 bd · 2 ba · 2,000 sqft

    13360 Sunny Retreat Ln, Winter Garden, FL

    Alan Martin · FRONTLINE FLORIDA REALTY, INC.

  • 13355 Sunny Retreat Ln — photo60Active

    $899,000

    3 bd · 3 ba · 2,710 sqft

    13355 Sunny Retreat Ln, Winter Garden, FL

    John Hart, PLLC · PREMIER SOTHEBYS INT'L REALTY

  • 15000 Canopy Cover Drive — photoPrice Reduced35Active

    $849,990

    3 bd · 4 ba · 2,861 sqft

    15000 Canopy Cover Drive, Winter Garden, FL

    Adrienne Escott · PULTE REALTY OF NORTH FLORIDA LLC

  • 2139 Tillman Ave — photoPrice Reduced48Active

    $840,000

    4 bd · 4 ba · 3,078 sqft

    2139 Tillman Ave, Winter Garden, FL

    Marti Purdy · MARTI PURDY PROPERTIES INC

  • 13361 Sunny Retreat Ln — photoPrice Reduced73Active

    $859,900

    4 bd · 3 ba · 3,172 sqft

    13361 Sunny Retreat Ln, Winter Garden, FL

    Tony Cruz, PA · EXP REALTY LLC

  • 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

  • 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

  • 15806 Gem View St — photoPrice Reduced37Active

    $465,000

    2 bd · 2 ba · 1,574 sqft

    15806 Gem View St, Winter Garden, FL

    Yanely Fernandez · FAST ACTION REALTY INC

  • Explore Winter Garden homes

    By price

    • Homes Under $200K
    • Homes Under $300K
    • Homes Under $400K
    • Homes Under $500K
    • Homes Under $600K
    • Homes Under $700K
    • Homes Under $800K
    • Homes Under $900K
    • Homes Under $1M
    • Luxury Homes

    By bedrooms

    • 2 Bedroom Homes
    • 3 Bedroom Homes
    • 4 Bedroom Homes
    • 5 Bedroom Homes

    By type

    • Single-Family Homes
    • Townhomes
    • Condos

    By feature

    • New Construction Homes
    • Homes with a Pool
    • Waterfront Homes
    • Foreclosures & Short Sales
    • 55+ Community Homes
    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

    Equal Housing OpportunityEqual Housing Lender

    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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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

    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.