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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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3 beds New construction With a pool

Homes Under $2M in Winter Park, FL — Page 4

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

Price Reduced38

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Active

$659,900

3 bd · 2 ba · 1,420 sqft

274 N Ranger Blvd, Winter Park, FL

Shannon Lee · EXPLORE FLORIDA REALTY SERVICES LLC

Price Reduced34Active

$629,000

3 bd · 2 ba · 1,783 sqft

508 Brechin Dr, Winter Park, FL

Mary Lowen · MTL REALTY LLC

$299,990

3 bd · 2 ba · 1,467 sqft

2275 Island Run, Winter Park, FL

Yukey Hoo · U KEY REALTY

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.

$425,000

3 bd · 3 ba · 1,755 sqft

2349 Shadowland Loop, Winter Park, FL

Lindsey Hudson · REAL BROKER, LLC

$130,000

1 bd · 1 ba · 645 sqft

2500 Lee Rd #143, Winter Park, FL

Carol Wittman · PALMANO GROUP RE BROKERAGE LLC

$1,350,000

4 bd · 4 ba · 2,998 sqft

1320 Orchid Ave, Winter Park, FL

Isis Sarcos · EXP REALTY LLC

Price Reduced58Active

$1,295,000

3 bd · 4 ba · 2,191 sqft

720 Pansy Ave, Winter Park, FL

Nick McKee · KELLER WILLIAMS WINTER PARK

$739,777

4 bd · 2 ba · 2,267 sqft

4039 Cool Water Ct, Winter Park, FL

Karen Arbutine · RE/MAX CENTRAL REALTY

$365,000

3 bd · 3 ba · 1,861 sqft

7506 Cranes Creek Ct #30, Winter Park, FL

Sylvia Marchese · TRANSCONTINENTAL REALTY GROUP,

$725,000

3 bd · 2 ba · 1,563 sqft

1850 Bryan Ave, Winter Park, FL

Jennifer King · CORCORAN PREMIER REALTY

$309,900

3 bd · 3 ba · 1,545 sqft

7530 Cranes Creek Ct, Winter Park, FL

Edward Hru · ROO REALTY LLC

$269,000

2 bd · 2 ba · 1,008 sqft

5108 Lazy Oaks Dr #5108, Winter Park, FL

Steven Koleno · BEYCOME OF FLORIDA LLC

Price Reduced40Active

$529,000

4 bd · 2 ba · 1,845 sqft

2211 King Richards Ct, Winter Park, FL

Nicole Howell · FANNIE HILLMAN & ASSOCIATES

$575,000

2 bd · 3 ba · 1,648 sqft

1259 Indiana Ave, Winter Park, FL

Karan Wienker · COLDWELL BANKER REALTY

Price Reduced49Active

$999,500

3 bd · 2 ba · 1,487 sqft

1220 Howell Branch Rd, Winter Park, FL

Fook Snipper · PARK PLACE REAL ESTATE

$269,000

2 bd · 1 ba · 710 sqft

151 N Orlando Ave #242, Winter Park, FL

Alexander Scures · COLONIALTOWN REALTY

Price Reduced27Active

$950,000

4 bd · 3 ba · 2,528 sqft

471 Holt Ave, Winter Park, FL

Tina Bollet · FLORIDA HOME TEAM REALTY LLC

Price Reduced17Active

$269,900

3 bd · 2 ba · 1,197 sqft

3302 Royal St, Winter Park, FL

Robert Arnold, Jr · SAND DOLLAR REALTY GROUP INC

$1,598,000

4 bd · 4 ba · 2,916 sqft

2430 Chantilly Ave, Winter Park, FL

Kelly Price · KELLY PRICE & COMPANY LLC

$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

$245,000

2 bd · 2 ba · 913 sqft

1250 S Denning Dr #Unit 233, Winter Park, FL

Samuel Kingsford · STOCKWORTH REALTY GROUP

$189,900

2 bd · 2 ba · 953 sqft

222 Lewfield Cir, Winter Park, FL

Joshua Neudigate · MARKET CONNECT REALTY LLC

1…3 4 5…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 · 84 sales · as of Sep 30, 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 30, 2026

Median list price: $630,000
Homes for sale: 383
Median days on market: 18 days

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

Year-over-year: 38.1%

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.