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Homes Under $500K in Winter Park, FL

Start here

Homes for sale by state
Home buying tips
Before you start looking
The buying timeline

Afford it

Today's mortgage rates
Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

Save search Advertise Sign In

Saved homes Saved searches Your tours Your inquiries Recently viewed Account settings

Safety & registry resources

Review official public-safety information for any area from these government sources:

U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
FBI: state sex-offender registry directory

3 beds New construction With a pool

2 listings

Selling Options

What's my home worth?
Compare selling options
Get an instant cash offer
Buy before you sell

Resources

How selling works
When should I sell?
Home selling tips
Pricing your home
What's worth fixing first
Find a seller's agent

Homes Under $500K in Winter Park, FL

Homes Under $500K in Winter Park, FL

2 Listings

Homes Under $500K in Winter Park, FL

2 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Price Reduced18Active
$434,990
3 bd · 2 ba · — sqft
405 Lake Fair Lane, Winter Park, FL
Franklyn Fennelys PA · Agent Trust Realty Corporation
Price Reduced28Active
$490,000
4 bd · 2 ba · 2,250 sqft
2008 Houndslake Drive, Winter Park, FL
Kevin McCulty · Mark Spain Real Estate

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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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Listing data & MLS disclosures

Space Coast MLS (Space Coast Association of REALTORS): IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Information is deemed reliable but not guaranteed.
Listing information ©2026 Space Coast MLS, Inc®. All Rights Reserved. Last Updated: 2026-08-28 13:56:01 UTC
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: 2026-08-04 23:51:39 UTC

By feature

New construction
With a pool

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

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

Winter Park housing market

July 2026 · This period is still settling

Selling at 99.3% of asking price

Buyers here are paying below asking. MLS · 51 sales · as of Jul 20, 2026

Homes that sold · County records, as of Jul 6, 2026

Median sale price: $519,000$385,000–$850,000 typical range
Price per sq. ft.: $344
Sales: 25
Paid in cash: 36.0%

Homes on the market · MLS, as of Jul 20, 2026

Median list price: $625,000
Homes for sale: 313
Median days on market: 39 days

Price trend · Assessor repeat sales, as of Jul 31, 2026

Year-over-year: 19.3%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 14, 2026

Median home size: 1,704 sq. ft.