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

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

Save search Advertise Sign In

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

Registered offenders on the map

Show registered offenders

Registered offenders on the map

Show registered offenders

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

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

Rentals
Commercial

Registered offenders on the map

Show registered offenders

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

3 beds New construction With a pool

3 Bedroom Homes in Winter Park, FL

26 listings

3 Bedroom Homes in Winter Park, FL

3 Bedroom Homes in Winter Park, FL

24 of 26 Listings

3 Bedroom Homes in Winter Park, FL

24 of 26 Listings

39

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Active

$1,450,000

3 bd · 3 ba · 2,756 sqft

100 S Virginia Ave #201, Winter Park, FL

Tiffany Grindstaff · KELLY PRICE & COMPANY LLC

$1,250,000

3 bd · 2 ba · 1,747 sqft

120 Broadview Ave, Winter Park, FL

Catherine D'Amico · FANNIE HILLMAN & ASSOCIATES

$3,790,000

3 bd · 2 ba · 1,277 sqft

4870 Seminole Ave, Winter Park, FL

Tamara Mazo Ferro · COLDWELL BANKER REALTY

$1,300,000

3 bd · 3 ba · 2,563 sqft

504 W Swoope Ave, Winter Park, FL

Jennifer Sloan · COMPASS FLORIDA LLC

$2,475,000

3 bd · 3 ba · 2,316 sqft

311 E Morse Blvd #1-5, Winter Park, FL

Skip Kirst · COLLADO REAL ESTATE

$2,350,000

3 bd · 4 ba · 3,110 sqft

200 S Interlachen Ave #350, Winter Park, FL

Rhonda Chesmore · KELLY PRICE & COMPANY LLC

Price Reduced54Active

$1,095,000

3 bd · 3 ba · 1,873 sqft

1922 Hammerlin Ave, Winter Park, FL

Felicia Donatelli · PALM PROPERTIES OF CF, INC.

Price Reduced58Active

$1,295,000

3 bd · 4 ba · 2,191 sqft

720 Pansy Ave, Winter Park, FL

Nick McKee · KELLER WILLIAMS WINTER PARK

$1,600,000

3 bd · 3 ba · 2,733 sqft

2207 Kindel Ave, Winter Park, FL

Sandra Velasquez · THE SIMON SIMAAN GROUP

$1,950,000

3 bd · 4 ba · 2,703 sqft

751 Pansy Ave, Winter Park, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

Price Reduced21Active

$1,449,000

3 bd · 3 ba · 2,080 sqft

150 E Reading Way, Winter Park, FL

Wendy Williams Crumit · FANNIE HILLMAN & ASSOCIATES

Price Reduced75Active

$1,949,500

3 bd · 4 ba · 2,422 sqft

1420 Aloma Ave, Winter Park, FL

Alejandra Silva · METROPOLITAN R.E SOLUTIONS INC

$3,895,000

3 bd · 5 ba · 3,878 sqft

125 S Interlachen Ave #1, Winter Park, FL

Skip Kirst · COLLADO REAL ESTATE

$1,275,000

3 bd · 3 ba · 1,329 sqft

240 Killarney Dr, Winter Park, FL

Shandy Ortiz · PREMIER SOTHEBYS INT'L REALTY

Price Reduced21Active

$1,999,900

3 bd · 2 ba · 1,765 sqft

1133 Bella Lago CV, Winter Park, FL

Hang Kendall · LPT REALTY, LLC

Price Reduced28Active

$1,495,000

3 bd · 3 ba · 1,944 sqft

462 W Lyman Ave, Winter Park, FL

Mick Night · PREMIER SOTHEBY'S INTL. REALTY

Price Reduced72Active

$2,695,000

3 bd · 4 ba · 3,286 sqft

660 W Morse Blvd, Winter Park, FL

Jennifer Sloan · COMPASS FLORIDA LLC

$1,399,000

3 bd · 3 ba · 2,585 sqft

512 W Swoope Ave, Winter Park, FL

Carmen Quintana · COLDWELL BANKER REALTY

Price ReducedOpen house Sat, Oct 3 · 11:00 AM39Active

$1,775,000

3 bd · 4 ba · 3,112 sqft

101 S New York Ave #311, Winter Park, FL

Tiffany Grindstaff · KELLY PRICE & COMPANY LLC

$3,150,000

3 bd · 5 ba · 3,244 sqft

125 S Interlachen Ave #2, Winter Park, FL

Erin Legler · CHARLES RUTENBERG REALTY ORLANDO

Price ReducedOpen house Sat, Oct 3 · 1:00 PM37Active

$1,499,000

3 bd · 5 ba · 2,756 sqft

641 Northwood Circle, Winter Park, FL

Sandra Cuba · PREMIER SOTHEBY'S INTL. REALTY

Price Reduced29Active

$2,625,000

3 bd · 4 ba · 3,048 sqft

413 W Morse Blvd, Winter Park, FL

AV Blalock · COLDWELL BANKER REALTY

Price Reduced33Active

$1,498,000

3 bd · 4 ba · 2,467 sqft

1841 Lake Spier Drive, Winter Park, FL

Nicole Seybold · FANNIE HILLMAN & ASSOCIATES

Price Reduced49Active

$1,150,000

3 bd · 2 ba · 2,158 sqft

1600 S Pennsylvania Ave, Winter Park, FL

Jami Giles · EXIT REAL ESTATE PROPERTY SOL

1 2

Explore Winter Park 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
Homes Under $1.25M
Homes Under $1.5M
Homes Under $1.75M
Homes Under $2M
Homes Under $2.25M
Homes Under $2.5M
Homes Over $3M
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

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

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.

© 2026 Realty.com. All rights reserved.PrivacyTermsCalifornia Privacy RightsAccessibilityLicensing

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

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 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

September 2026 · This period is still settling

Selling at 97.9% of asking price

Buyers here are paying below asking. MLS · 73 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 16, 2026

Median sale price: $632,500$389,375–$1,088,750 typical range
Price per sq. ft.: $379
Sales: 60
Paid in cash: 50.0%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $630,000

Homes for sale

383

Median days on market

17 days

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

Year-over-year: 40.9%

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.