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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

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

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When should I sell?
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Pricing your home
What's worth fixing first
Find a seller's agent

3 beds New construction With a pool

Homes Under $2M in Winter Park, FL — Page 2

299 listings

Homes Under $2M in Winter Park, FL

Homes Under $2M in Winter Park, FL

24 of 299 Listings

Homes Under $2M in Winter Park, FL

24 of 299 Listings

30Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

$429,900

3 bd · 2 ba · 1,398 sqft

2818 Ambergate Rd, Winter Park, FL

Noella Tinkler · MARK SPAIN REAL ESTATE

$1,890,000

4 bd · 4 ba · 3,307 sqft

2614 Parkland Dr, Winter Park, FL

Ryan Gaston · JW GASTON LLC

$474,900

3 bd · 2 ba · 1,706 sqft

3334 Young St, Winter Park, FL

Jason Alves · EQUITYPRO LLC

$1,450,000

3 bd · 3 ba · 2,756 sqft

100 S Virginia Ave #201, Winter Park, FL

Tiffany Grindstaff · KELLY PRICE & COMPANY LLC

$449,900

4 bd · 2 ba · 1,627 sqft

3209 Heartwood Ave, Winter Park, FL

James Fitzgibbon · LEDGE REAL ESTATE SOLUTIONS LLC

$319,000

2 bd · 2 ba · 1,287 sqft

192 Balfour Dr #2, Winter Park, FL

Tricia Ramsby · BHHS FLORIDA REALTY

$227,000

2 bd · 2 ba · 1,120 sqft

602 Trinidad Ct #602, Winter Park, FL

Clara Herrera · CLARA HERRERA REALTY

$1,250,000

3 bd · 2 ba · 1,747 sqft

120 Broadview Ave, Winter Park, FL

Catherine D'Amico · FANNIE HILLMAN & ASSOCIATES

$659,000

3 bd · 2 ba · 2,265 sqft

5303 Pine Lily Cir, Winter Park, FL

Jonathan Casique · PM ELITE REALTY LLC

$285,000

3 bd · 2 ba · 1,509 sqft

7348 Grand Ave, Winter Park, FL

Joseph Doher · BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

Open house Sat, Oct 3 · 12:00 PM31Active

$1,599,000

4 bd · 4 ba · 2,942 sqft

533 Country Club Dr, Winter Park, FL

Jill Healey · KELLER WILLIAMS WINTER PARK

$599,000

4 bd · 4 ba · 2,322 sqft

4260 Bear Gully Rd, Winter Park, FL

Alexandre Zapparoli LLC · WRA BUSINESS & REAL ESTATE

$150,000

2 bd · 2 ba · 1,063 sqft

7453 Daniel Webster Dr #a5, Winter Park, FL

Laila Dkhissi · LA ROSA REALTY PREMIER LLC

$359,000

2 bd · 1 ba · 830 sqft

1306 S Pennsylvania Ave #5, Winter Park, FL

Lisa Gould · KELLER WILLIAMS WINTER PARK

Open house Sat, Oct 10 · 12:00 PM50Active

$925,000

4 bd · 3 ba · 2,578 sqft

2572 Fifeshire Dr, Winter Park, FL

MaryAnne Branner · PREMIER SOTHEBY'S INTL. REALTY

$249,000

3 bd · 3 ba · 1,720 sqft

2463 Grand Teton Cir #2463, Winter Park, FL

Jessica Polanco · MAINFRAME REAL ESTATE

$299,900

3 bd · 2 ba · 1,078 sqft

5080 Seminole Ave, Winter Park, FL

David Johnston · CREEGAN GROUP

$699,000

3 bd · 2 ba · 1,450 sqft

250 Carolina Ave #202, Winter Park, FL

Kevin McClanahan · FANNIE HILLMAN & ASSOCIATES

Open house Sat, Oct 3 · 10:00 AM48Active

$1,095,000

4 bd · 4 ba · 2,135 sqft

1517 Harmon Ave, Winter Park, FL

Steven Koleno · BEYCOME OF FLORIDA LLC

$850,000

3 bd · 3 ba · 2,488 sqft

2345 Brookshire Ave, Winter Park, FL

Amy Turner · KELLER WILLIAMS WINTER PARK

$134,900

2 bd · 2 ba · 756 sqft

7302 Swallow Run #7302, Winter Park, FL

Katie Nguyen · THE NAVY HOUSE

$427,000

4 bd · 3 ba · 1,714 sqft

1386 Clematis Ln, Winter Park, FL

Michelle Torrente · ROBERT SLACK LLC

Open house Thu, Oct 1 · 4:30 AM41Active

$675,000

4 bd · 2 ba · 1,688 sqft

2215 Woodcrest Dr, Winter Park, FL

Shari Klafter · KELLER WILLIAMS WINTER PARK

Open house Sun, Oct 4 · 11:00 AM64Active

$895,000

4 bd · 3 ba · 1,876 sqft

618 Blairshire Cir, Winter Park, FL

Ken Pozek · REAL BROKER, LLC

1 2 3…13

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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.

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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.