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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?
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Get an instant cash offer
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Find a seller's agent

3 beds New construction With a pool

Homes Under $2M in Winter Park, FL — Page 3

295 listings

Homes Under $2M in Winter Park, FL

Homes Under $2M in Winter Park, FL

24 of 295 Listings

Homes Under $2M in Winter Park, FL

24 of 295 Listings

62Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

$850,000

3 bd · 3 ba · 2,488 sqft

2345 Brookshire Ave, Winter Park, FL

Amy Turner · KELLER WILLIAMS WINTER PARK

$427,000

4 bd · 3 ba · 1,714 sqft

1386 Clematis Ln, Winter Park, FL

Michelle Torrente · ROBERT SLACK LLC

$675,000

4 bd · 2 ba · 1,688 sqft

2215 Woodcrest Dr, Winter Park, FL

Shari Klafter · KELLER WILLIAMS WINTER PARK

$895,000

4 bd · 3 ba · 1,876 sqft

618 Blairshire Cir, Winter Park, FL

Ken Pozek · REAL BROKER, LLC

$380,000

3 bd · 2 ba · 1,277 sqft

4870 Seminole Ave, Winter Park, FL

Tamara Mazo Ferro · COLDWELL BANKER REALTY

$1,579,000

4 bd · 4 ba · 2,718 sqft

2417 Chantilly Ave, Winter Park, FL

Amanda Wood · RE/MAX EXCLUSIVE COLLECTION

$1,300,000

3 bd · 3 ba · 2,563 sqft

504 W Swoope Ave, Winter Park, FL

Jennifer Sloan · COMPASS FLORIDA LLC

$960,000

2 bd · 1 ba · 1,290 sqft

447 N Phelps Ave, Winter Park, FL

Prentice Williams · KELLER WILLIAMS ADVANTAGE REALTY

Price Reduced28Active

$440,000

4 bd · 2 ba · 2,189 sqft

2301 Conifer Ave, Winter Park, FL

Gregory Buckley · LOKATION

$1,095,000

4 bd · 3 ba · 2,803 sqft

443 Broadview Ave, Winter Park, FL

Nancy Bagby · FANNIE HILLMAN & ASSOCIATES

$950,000

3 bd · 2 ba · 1,887 sqft

913 Moss Ln, Winter Park, FL

Peter Rodriguez · VECTOR REALTY

$234,900

2 bd · 2 ba · 1,295 sqft

2383 Sun Valley Cir #2383, Winter Park, FL

Carmen Aridas · RE/MAX PRIME PROPERTIES

$170,000

2 bd · 3 ba · 1,031 sqft

7476 Woodburn Ct #38, Winter Park, FL

Habib Fahs · COLDWELL BANKER REALTY

Price Reduced73Active

$769,000

4 bd · 3 ba · 2,141 sqft

2410 Sherbrooke Rd, Winter Park, FL

Li Ju Huang · AMERICA REAL ESTATE COMPANY LL

$295,000

2 bd · 2 ba · 1,544 sqft

2302 Barbados Dr, Winter Park, FL

George Freelove · KELLER WILLIAMS REALTY AT THE PARKS

$1,925,000

5 bd · 4 ba · 3,246 sqft

2260 Mulbry Dr, Winter Park, FL

Alex Bogumil · KONA REALTY SERVICES LLC

$365,000

3 bd · 2 ba · 1,185 sqft

2136 Linden Rd, Winter Park, FL

Patty Hru · PAM REAL ESTATE

Price Reduced89Active

$1,550,000

6 bd · 5 ba · 5,239 sqft

1257 Wading Waters Cir, Winter Park, FL

Rob Breese, III · RE/MAX TOWN & COUNTRY REALTY

$380,000

3 bd · 1 ba · 1,143 sqft

2626 Ambergate Rd, Winter Park, FL

Brett Winters · OLDE TOWN BROKERS INC

Price Reduced35Active

$675,000

4 bd · 2 ba · 1,509 sqft

2260 Coldstream Dr, Winter Park, FL

Steven Ritz · KELLER WILLIAMS WINTER PARK

Price Reduced69Active

$775,000

5 bd · 4 ba · 2,840 sqft

1164 Dodd Road, Winter Park, FL

Michael John Rothenburg · Charles Rutenberg Realty FTL

$495,000

4 bd · 2 ba · 1,756 sqft

3020 Nicholson Dr, Winter Park, FL

Kristin Duncan · CHARLES RUTENBERG REALTY ORLANDO

$165,000

2 bd · 2 ba · 840 sqft

3651 N Goldenrod Rd #C109, Winter Park, FL

Valerie Wanzer · REAL ESTATE PROFESSIONALS SE

$245,000

2 bd · 2 ba · 908 sqft

1250 S Denning Dr #127, Winter Park, FL

Drew Henner · PREMIER SOTHEBY'S INTL. REALTY

1 2 3 4…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

BeachesMLS: All listings featuring the BMLS logo are provided by Beaches MLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Information is provided exclusively for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Listing information ©2026 Beaches Multiple Listing Service®. All Rights Reserved. Data Last Updated: 2026-10-04 18:02:54 UTC
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 23, 2026

Median sale price: $602,500$441,750–$1,016,350 typical range
Price per sq. ft.: $358
Sales: 78
Paid in cash: 46.2%

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.