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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

4 Bedroom Homes in Winter Park, FL — Page 3

103 listings

4 Bedroom Homes in Winter Park, FL

4 Bedroom Homes in Winter Park, FL

22 of 103 Listings

4 Bedroom Homes in Winter Park, FL

22 of 103 Listings

12Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

$1,699,000

4 bd · 4 ba · 2,530 sqft

2308 Mulbry Dr, Winter Park, FL

Brandon Geers · COMPASS FLORIDA LLC

$1,725,000

4 bd · 4 ba · 3,727 sqft

1840 Bryan Ave, Winter Park, FL

Jennifer Draper · REAL BROKER, LLC

Price Reduced37Active

$665,000

4 bd · 3 ba · 1,770 sqft

1122 Wildmeadow Run, Winter Park, FL

Ken Pozek · REAL BROKER, LLC

Price Reduced92Active

$985,000

4 bd · 3 ba · 2,868 sqft

2667 Cochise Trl, Winter Park, FL

Beverley Kistler · COLDWELL BANKER REALTY

$1,749,000

4 bd · 4 ba · 2,715 sqft

2525 Lafayette Ave, Winter Park, FL

Matt Tomaszewski · CORCORAN PREMIER REALTY

$1,250,000

4 bd · 1 ba · 1,260 sqft

230 Killarney Dr, Winter Park, FL

Shandy Ortiz · PREMIER SOTHEBYS INT'L REALTY

$775,000

4 bd · 3 ba · 1,899 sqft

1562 Arbor Park Dr, Winter Park, FL

Abby Greenberg · COMPASS FLORIDA LLC

Price Reduced30Active

$1,875,000

4 bd · 4 ba · 3,440 sqft

922 N Pennsylvania Ave, Winter Park, FL

Mick Night · PREMIER SOTHEBY'S INTL. REALTY

$1,600,000

4 bd · 4 ba · 2,568 sqft

250 Killarney, Winter Park, FL

Nancy Rossman · FLORIDA PROPERTY SPECIALIST

Price Reduced46Active

$699,500

4 bd · 3 ba · 2,197 sqft

1418 Lone Feather Trl, Winter Park, FL

Harif Hazera LLC · PREMIER SOTHEBY'S INTL. REALTY

Price Reduced26Active

$399,999

4 bd · 2 ba · 1,653 sqft

1401 Aster Ct, Winter Park, FL

Brian Dodd · SPARROW REALTY & RENTALS

Price Reduced38Active

$368,000

4 bd · 2 ba · 1,240 sqft

885 Carnation Dr, Winter Park, FL

Tashania Brown · RADIUS REALTY GROUP LLC

Price ReducedOpen house Sun, Oct 4 · 2:00 PM57Active

$1,525,000

4 bd · 4 ba · 3,723 sqft

341 E Reading Way, Winter Park, FL

Wendy Williams Crumit · FANNIE HILLMAN & ASSOCIATES

Price ReducedOpen house Sat, Oct 3 · 1:00 PM46Active

$925,000

4 bd · 3 ba · 2,075 sqft

3006 Northwood Blvd, Winter Park, FL

Daren Ellington · ORLANDO HOMES GROUP LLC

$450,000

4 bd · 3 ba · 1,980 sqft

1564 Lawndale Cir, Winter Park, FL

Yahya Chhotani LLC · SET HOMES REALTY LLC

Price ReducedOpen house Sat, Oct 3 · 12:00 PM31Active

$1,262,500

4 bd · 4 ba · 3,024 sqft

2015 Summerfield Rd, Winter Park, FL

Courtney Lindsay · UNITED REAL ESTATE PREFERRED

$475,000

4 bd · 2 ba · 2,250 sqft

2008 Houndslake Drive, Winter Park, FL

Kevin McCulty · Mark Spain Real Estate

$725,000

4 bd · 3 ba · 2,196 sqft

1316 Blue Stem Ln, Winter Park, FL

Matthew Fong · AFFINITY REALTY LLC

Price Reduced59Active

$455,000

4 bd · 3 ba · 1,903 sqft

8433 Commander CV, Winter Park, FL

Brandi Cepeda · CEPEDA REAL ESTATE 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

Price Reduced28Active

$655,000

4 bd · 3 ba · 1,647 sqft

2831 Mulford Ave, Winter Park, FL

Patrick Arenson · UNITED REAL ESTATE PREFERRED

$3,500,000

4 bd · 4 ba · 4,036 sqft

2240 Venetian Way, Winter Park, FL

Johnny Hurlburt · COLDWELL BANKER REALTY

1 2 3 4 5

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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

Daytona Beach Area Association of REALTORS: IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Information is deemed reliable but not guaranteed.
Listing information ©2026 Daytona Beach Area Association of Realtors, Inc®. All Rights Reserved. Last Updated: 2026-10-02 19:57:02 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 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.