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Before you start looking
The buying timeline

Afford it

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How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
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3 beds New construction With a pool

4 Bedroom Homes in Winter Park, FL — Page 5

101 listings

4 Bedroom Homes in Winter Park, FL

4 Bedroom Homes in Winter Park, FL

5 of 101 Listings

4 Bedroom Homes in Winter Park, FL

5 of 101 Listings

Price Reduced50Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

$1,380,000

4 bd · 4 ba · 2,170 sqft

1751 Goodrich Ave, Winter Park, FL

Stephanie Baldner · EXP REALTY LLC

Price Reduced20Active

$680,000

4 bd · 4 ba · 2,664 sqft

432 W Swoope Ave, Winter Park, FL

Thomas Bonner · COLDWELL BANKER RESIDENTIAL RE

$1,750,000

4 bd · 3 ba · 2,350 sqft

1840 Anzle Ave, Winter Park, FL

Oscar Rodriguez · B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE

Price Reduced34Active

$485,000

4 bd · 2 ba · 2,092 sqft

2217 Sussex Rd, Winter Park, FL

Justin Hilton · PREFERRED REAL ESTATE BROKERS

Price Reduced27Active

$389,900

4 bd · 2 ba · 1,627 sqft

1849 Viburnum Ln, Winter Park, FL

Lesly Hijar · REAL BROKER, LLC

1…4 5

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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.