Homes Under $500K in Winter Park, FL

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24 of 151 Listings

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Thomas O'Leary

Realty.com

Lic. #BK3453168

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29Active
$305,000
3 bd · 1 ba · 1,216 sqft
2640 Beverly Ave, Winter Park, FL
Celeste Martinez · REAL BROKER, LLC
New16Active
$329,000
3 bd · 2 ba · 1,229 sqft
1740 Puritan Ave, Winter Park, FL
Brenda Brooks · KELLER WILLIAMS REALTY SMART 1
Open house Sun, Oct 18 · 12:00 PM30Active
$415,900
3 bd · 2 ba · 1,412 sqft
3409 Ferndell Dr, Winter Park, FL
Veronica Lewis · LPT REALTY, LLC

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.

About Homes Under $500K in Winter Park, FL

Homes Under $500K in Winter Park, FL: 151 active listings as of October 18, 2026, 00:32 UTC.

Property types among these 151 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	69	45.7%
Single Family Residence	61	40.4%
Townhouse	18	11.9%

Winter Park housing market

September 2026

Selling at 97.9% of asking price

Buyers here are paying below asking. MLS · 84 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 28, 2026

Median sale price: $565,000$410,000–$952,600 typical range
Price per sq. ft.: $342
Sales: 92
Paid in cash: 44.6%

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

Median list price: $630,000
Homes for sale: 383
Median days on market: 18 days

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

Year-over-year: 28.1%

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

Median home size: 1,731 sq. ft.

Winter Park, FL community profile

Population: 31,855
Median income: $98,252
Housing units: 15,404
People per sq. mi.: 1,409.5
Area: 22.6 sq. mi.

Source: HJN community data

Homes Under $500K in Winter Park, FL

Your local brokerage

Listing data & MLS disclosures

About Homes Under $500K in Winter Park, FL

Winter Park housing market

Homes that sold · County records, as of Sep 28, 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 Park, FL community profile

Explore Winter Park homes

Listing data & MLS disclosures

Your local brokerage

Your local brokerage

Winter Park, FL community profile

Winter Park housing market

Homes that sold · County records, as of Sep 28, 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