Homes Under $500K in Winter Garden, FL

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24 of 295 Listings

Your Winter Garden agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

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New19Active
$499,900
2 bd · 2 ba · 1,185 sqft
17138 Arrowhead Blvd, Winter Garden, FL
Dan Lu · WEICHERT REALTORS HALLMARK PRO
29Active
$350,000
3 bd · 2 ba · 1,352 sqft
1444 Kenny Ct, Winter Garden, FL
Jenny Wemert · WEMERT GROUP REALTY LLC
1Active
$486,234
2 bd · 2 ba · 1,396 sqft
14501 Grove Resort Ave Unit 2333, Winter Garden, FL
Valentina Grajales · Cervera Real Estate Inc.

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.

About Homes Under $500K in Winter Garden, FL

Homes Under $500K in Winter Garden, FL: 295 active listings as of October 18, 2026, 14:58 UTC.

Property types among these 295 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
Property type	Listings	Share
Condominium	120	40.7%
Townhouse	88	29.8%
Single Family Residence	53	18.0%
Manufactured Home	24	8.1%

Winter Garden housing market

September 2026 · This period is still settling

Selling at 98.2% of asking price

Buyers here are paying below asking. MLS · 212 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 29, 2026

Median sale price: $679,610$500,125–$951,800 typical range
Price per sq. ft.: $260
Sales: 234
Paid in cash: 36.8%

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: 19.4%

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.

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

Homes Under $500K in Winter Garden, FL

Your Winter Garden agent

Listing data & MLS disclosures

About Homes Under $500K in Winter Garden, FL

Winter Garden housing market

Homes that sold · County records, as of Sep 29, 2026

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

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

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

Winter Garden, FL community profile

Explore Winter Garden homes

Listing data & MLS disclosures

Your Winter Garden agent

Your Winter Garden agent

Winter Garden, FL community profile

Winter Garden housing market

Homes that sold · County records, as of Sep 29, 2026

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

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

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