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

Homes Over $3M in Winter Park, FL

30 listings

Homes Over $3M in Winter Park, FL

Homes Over $3M in Winter Park, FL

24 of 30 Listings

Homes Over $3M in Winter Park, FL

24 of 30 Listings

11Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

$3,195,000

5 bd · 6 ba · 4,139 sqft

2119 Howard Dr, Winter Park, FL

Laura Earl · CORCORAN PREMIER REALTY

$6,195,000

5 bd · 6 ba · 5,096 sqft

698 N New York Ave, Winter Park, FL

Mick Night · PREMIER SOTHEBY'S INTL. REALTY

$3,695,999

4 bd · 5 ba · 3,658 sqft

1742 Temple Dr, Winter Park, FL

Mark Anthony Buot · ROI AVE LLC

$3,495,000

5 bd · 6 ba · 4,478 sqft

662 Granville Drive, Winter Park, FL

Nathalie Bates · PREMIER SOTHEBY'S INTL. REALTY

$6,995,000

5 bd · 6 ba · 5,479 sqft

901 Golfview Ter, Winter Park, FL

Mick Night · PREMIER SOTHEBY'S INTL. REALTY

$5,500,000

5 bd · 7 ba · 5,181 sqft

1166 Palmer Ave, Winter Park, FL

Prentice Williams · KELLER WILLIAMS ADVANTAGE REALTY

$3,790,000

3 bd · 2 ba · 1,277 sqft

4870 Seminole Ave, Winter Park, FL

Tamara Mazo Ferro · COLDWELL BANKER REALTY

$4,400,000

4 bd · 6 ba · 3,720 sqft

702 Via Bella, Winter Park, FL

Mick Night · PREMIER SOTHEBY'S INTL. REALTY

$3,950,000

4 bd · 2 ba · 1,652 sqft

540 N Pennsylvania Ave, Winter Park, FL

Mary Heidrich · COLDWELL BANKER REALTY

$4,325,000

5 bd · 5 ba · 4,853 sqft

250 W Reading Way, Winter Park, FL

Brian Mitnik · RE/MAX 200 REALTY

$5,195,900

5 bd · 7 ba · 5,122 sqft

825 Palmer Ave, Winter Park, FL

Laura Earl · CORCORAN PREMIER REALTY

$3,395,000

5 bd · 6 ba · 4,015 sqft

160 W Rockwood Way, Winter Park, FL

Alison Mosley · PREMIER SOTHEBY'S INTL. REALTY

$5,999,990

4 bd · 5 ba · 3,880 sqft

2661 Via Tuscany, Winter Park, FL

Nohora Gomez · COLDWELL BANKER REALTY

$3,265,000

5 bd · 6 ba · 4,949 sqft

1761 Legion Dr, Winter Park, FL

Harry Pool, III · COLDWELL BANKER REALTY

$3,600,000

4 bd · 5 ba · 4,202 sqft

276 Detmar Dr, Winter Park, FL

Melanie Johnston · CALL IT CLOSED INTL REALTY

Price Reduced72Active

$3,750,000

4 bd · 3 ba · 3,377 sqft

2622 Lake Howell Ln, Winter Park, FL

Brian Hyser · THE AGENCY FL

$3,890,000

6 bd · 5 ba · 4,677 sqft

620 Virginia Dr, Winter Park, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

$4,650,000

5 bd · 6 ba · 4,827 sqft

857 Brock St, Winter Park, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

$3,895,000

3 bd · 5 ba · 3,878 sqft

125 S Interlachen Ave #1, Winter Park, FL

Skip Kirst · COLLADO REAL ESTATE

$5,600,000

5 bd · 6 ba · 5,152 sqft

2228 Azalea Pl, Winter Park, FL

Quentin Green, II · COMPASS FLORIDA LLC

Price Reduced67Active

$4,700,000

4 bd · 7 ba · 5,550 sqft

231 Chelton Cir, Winter Park, FL

Joseph Doher · BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

$3,150,000

3 bd · 5 ba · 3,244 sqft

125 S Interlachen Ave #2, Winter Park, FL

Erin Legler · CHARLES RUTENBERG REALTY ORLANDO

$3,500,000

4 bd · 4 ba · 4,036 sqft

2240 Venetian Way, Winter Park, FL

Johnny Hurlburt · COLDWELL BANKER REALTY

$6,000,000

5 bd · 8 ba · 7,397 sqft

1571 Woodland Ave, Winter Park, FL

Vonda Fields · CHARLES RUTENBERG REALTY ORLANDO

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.