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3 bedsNew constructionWith a pool
Homes Under $500K in Winter Garden, FL
292 listings

Homes Under $500K in Winter Garden, FL

Homes Under $500K in Winter Garden, FL

Show Map
24 of 292 Listings
Map

Homes Under $500K in Winter Garden, FL

24 of 292 Listings

  1. 14501 Grove Resort Ave #1440 — photoNew67

Your Winter Garden agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLCCall Veronica
Active

$159,999

2 bd · 2 ba · 1,375 sqft

14501 Grove Resort Ave #1440, Winter Garden, FL

James Donovan · TEAM DONOVAN

  • 17138 Arrowhead Blvd — photo22Active

    $499,900

    2 bd · 2 ba · 1,185 sqft

    17138 Arrowhead Blvd, Winter Garden, FL

    Dan Lu · WEICHERT REALTORS HALLMARK PRO

  • 1444 Kenny Ct — photo28Active

    $350,000

    3 bd · 2 ba · 1,352 sqft

    1444 Kenny Ct, Winter Garden, FL

    Jenny Wemert · WEMERT GROUP REALTY LLC

  • 14501 Grove Resort Ave Unit 2333 — photo1Active

    $486,234

    2 bd · 2 ba · 1,396 sqft

    14501 Grove Resort Ave Unit 2333, Winter Garden, FL

    Valentina Grajales · Cervera Real Estate Inc.

  • 15613 Boggy Oak Cir #110a — photo31Active

    $299,900

    2 bd · 2 ba · 1,216 sqft

    15613 Boggy Oak Cir #110a, Winter Garden, FL

    Aileen Frauman · COLEDEV REAL ESTATE LLC

  • 14732 Avenida de Palma 5036 — photo16Active

    $260,000

    2 bd · — ba · 1,568 sqft

    14732 Avenida de Palma 5036, Winter Garden, FL

  • 1210 Brandy Lake View Cir — photo31Active

    $450,000

    3 bd · 2 ba · 1,502 sqft

    1210 Brandy Lake View Cir, Winter Garden, FL

    Erica Diaz · HOMEVEST REALTY

  • 345 E Maple St — photo1Active

    $295,000

    2 bd · 1 ba · 556 sqft

    345 E Maple St, Winter Garden, FL

    Alexia Clemens · EXP REALTY LLC

  • 1300 Eastern Pecan Pl #208 — photo63Active

    $298,500

    3 bd · 2 ba · 1,453 sqft

    1300 Eastern Pecan Pl #208, Winter Garden, FL

    Mildred Hershiser · EXP REALTY LLC

  • 1956 Portcastle Cir — photo30Active

    $429,000

    4 bd · 3 ba · 1,606 sqft

    1956 Portcastle Cir, Winter Garden, FL

    Jason Ding · ORLANDO REGIONAL PROPERTY MANAGEMENT

  • 8067 Glenlloyd Ave — photo25Active

    $399,000

    3 bd · 3 ba · 1,626 sqft

    8067 Glenlloyd Ave, Winter Garden, FL

    Jacquelyn Voigt · KELLER WILLIAMS REALTY AT THE LAKES

  • 14630 Avenida De Palma 5049 — photo11Active

    $149,000

    3 bd · — ba · — sqft

    14630 Avenida De Palma 5049, Winter Garden, FL

  • 159 9th St — photo32Active

    $369,900

    3 bd · 2 ba · 1,188 sqft

    159 9th St, Winter Garden, FL

    Thomas Greenwood · CHARLES RUTENBERG REALTY ORLANDO

  • 14501 Grove Resort Ave #1218 — photo26Active

    $235,000

    2 bd · 2 ba · 1,265 sqft

    14501 Grove Resort Ave #1218, Winter Garden, FL

    Kim Goldin · KELLER WILLIAMS ADVANTAGE REALTY

  • 341 Southern Pecan Cir #202 — photo39Active

    $220,000

    1 bd · 1 ba · 738 sqft

    341 Southern Pecan Cir #202, Winter Garden, FL

    Merly Esgro · IAD REAL ESTATE

  • 1069 Mildred Dixon Way — photo16Active

    $275,000

    3 bd · 2 ba · 1,036 sqft

    1069 Mildred Dixon Way, Winter Garden, FL

    Robert Christiano · COLDWELL BANKER REALTY

  • 9469 Meadow Hunt Way — photo34Active

    $485,000

    4 bd · 3 ba · 1,868 sqft

    9469 Meadow Hunt Way, Winter Garden, FL

    Huimei Yang · HANG SENG REALTY , INC

  • 6270 Sunny Time Avenue — photoOpen house Sat, Oct 24 · 10:00 AM26Active

    $435,890

    3 bd · 3 ba · 1,683 sqft

    6270 Sunny Time Avenue, Winter Garden, FL

    Adrienne Escott · PULTE REALTY OF NORTH FLORIDA LLC

  • 14501 Grove Resort Unit 3419 — photo7Active

    $420,000

    3 bd · 2 ba · 1,396 sqft

    14501 Grove Resort Unit 3419, Winter Garden, FL

    Andrea Rosil PA · Coldwell Banker Realty

  • 14501 Grove Resort Ave #3631 — photo40Active

    $164,900

    2 bd · 2 ba · 1,375 sqft

    14501 Grove Resort Ave #3631, Winter Garden, FL

    Allan Sutton · SUN CREST FLORIDA PROPERTIES

  • 2020 Portcastle Cir — photo36Active

    $455,000

    3 bd · 3 ba · 1,857 sqft

    2020 Portcastle Cir, Winter Garden, FL

    Mike Vein · EXP REALTY LLC

  • 14501 Grove Resort #1723 — photo48Active

    $344,900

    3 bd · 3 ba · 1,544 sqft

    14501 Grove Resort #1723, Winter Garden, FL

    Ciro Noccioli Monteiro Alves · LPT REALTY, LLC

  • 9936 Pallida Hickory Way — photo37Active

    $468,000

    3 bd · 3 ba · 1,744 sqft

    9936 Pallida Hickory Way, Winter Garden, FL

    Erika Gao · RC GROUP REALTY LLC

  • 14501 Grove Resort Ave #2539 — photo41Active

    $163,000

    2 bd · 2 ba · 1,375 sqft

    14501 Grove Resort Ave #2539, Winter Garden, FL

    Bill Traback · MBI REALTY LLC

  • 12…13

    Explore Winter Garden homes

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    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

    NY State MLS
    The data relating to real estate for sale on this website comes in part from the Internet Data exchange (IDX) program of the New York State Alliance MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Real estate listings held by brokerage firms other than Realty.com, are indicated by detailed information about them such as the name of the listing firms. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither the listing broker(s) nor Realty.com shall be responsible for any typographical errors, misinformation, misprints, and shall be held totally harmless. Copyright © 2026 New York State Alliance and participating MLS's - CNYIS, UNYREIS and WNYREIS. All Rights Reserved.
    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: 2026-10-16 19:00:05 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

    Winter Garden 12-month median sale price trend

    Selling at 98.3% of asking price

    Buyers here are paying below asking. MLS · 215 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 30, 2026

    Median sale price
    $635,000$488,300–$925,000 typical range
    Price per sq. ft.
    $256
    Sales
    265
    Paid in cash
    36.2%

    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
    36 days

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

    Year-over-year
    11.8%

    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.