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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 4

103 listings

4 Bedroom Homes in Winter Park, FL

4 Bedroom Homes in Winter Park, FL

24 of 103 Listings

4 Bedroom Homes in Winter Park, FL

24 of 103 Listings

5Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

$500,000

4 bd · 3 ba · 2,031 sqft

2054 Eastbrook Blvd, Winter Park, FL

Melissa Stalzer · LPT REALTY, LLC

$695,000

4 bd · 3 ba · 2,312 sqft

715 S Ranger Blvd, Winter Park, FL

Chuck Tolfa · DAHLIA REALTY GROUP

Price Reduced38Active

$1,075,000

4 bd · 4 ba · 2,469 sqft

1404 Border Dr, Winter Park, FL

Brian Hyser · THE AGENCY FL

Price Reduced55Active

$469,900

4 bd · 2 ba · 1,624 sqft

1320 Gladiolas Dr, Winter Park, FL

Deborah Morgan · OPTIMA REAL ESTATE

Price Reduced76Active

$1,425,000

4 bd · 4 ba · 2,642 sqft

1581 Magnolia Ave, Winter Park, FL

Jo Ann Lamar · PREMIER SOTHEBY'S INTL. REALTY

Price ReducedOpen house Sun, Oct 4 · 1:00 PM50Active

$1,600,000

4 bd · 4 ba · 3,065 sqft

723 Symonds Ave, Winter Park, FL

Nick McKee · KELLER WILLIAMS WINTER PARK

Price Reduced37Active

$599,000

4 bd · 3 ba · 2,102 sqft

1946 Strathaven Rd, Winter Park, FL

Youbel Montesino · LPT REALTY, LLC

Price Reduced44Active

$999,000

4 bd · 5 ba · 2,638 sqft

616 Brechin Dr, Winter Park, FL

Alison Mosley · PREMIER SOTHEBY'S INTL. REALTY

$390,000

4 bd · 2 ba · 1,607 sqft

2512 Eastbrook Blvd, Winter Park, FL

Joseph Firmin · LPT REALTY, LLC

$1,249,900

4 bd · 4 ba · 2,936 sqft

Address withheld · Winter Park, FL

Kim Griffin · RE/MAX EXCLUSIVE COLLECTION

Price Reduced39Active

$1,495,000

4 bd · 2 ba · 2,640 sqft

446 Melrose Ave, Winter Park, FL

Audra Wilks · PREMIER SOTHEBY'S INTL. REALTY

Price Reduced85Active

$3,995,000

4 bd · 6 ba · 4,066 sqft

1441 Cardinal Ct, Winter Park, FL

Damian Bergler · CHARLES RUTENBERG REALTY ORLANDO

Price Reduced39Active

$1,299,000

4 bd · 4 ba · 2,459 sqft

102 Bell Pl, Winter Park, FL

Nick McKee · KELLER WILLIAMS WINTER PARK

Price Reduced46Active

$775,000

4 bd · 4 ba · 2,589 sqft

1369 Blue Stem Ln, Winter Park, FL

He Gao · U S GLORY REALTY

$1,250,000

4 bd · 4 ba · 2,525 sqft

1870 Staunton Ave, Winter Park, FL

Vinny Lay · COMPASS FLORIDA LLC

$825,000

4 bd · 4 ba · 2,589 sqft

1131 Wildmeadow Run, Winter Park, FL

Joann Beck · BECK REALTY LLC

Price Reduced36Active

$1,595,000

4 bd · 4 ba · 3,048 sqft

1570 Palmer Ave, Winter Park, FL

David Auerbach · PARK TOWN REAL ESTATE LLC

Price Reduced51Active

$2,495,000

4 bd · 4 ba · 3,553 sqft

541 W Canton Ave, Winter Park, FL

Bianca Khoury · PREMIER SOTHEBY'S INTL. REALTY

Price Reduced46Active

$1,750,000

4 bd · 4 ba · 3,249 sqft

1750 Carollee Lane, Winter Park, FL

Michelle Hochfelder · PREMIER SOTHEBY'S INTL. REALTY

$1,550,000

4 bd · 4 ba · 2,756 sqft

905 Enclave Pl, Winter Park, FL

Matthew Burks · CORCORAN PREMIER REALTY

$1,550,000

4 bd · 4 ba · 2,738 sqft

901 Enclave Pl, Winter Park, FL

Laura Earl · CORCORAN PREMIER REALTY

Price Reduced42Active

$1,649,000

4 bd · 4 ba · 2,807 sqft

1903 N Park Ave, Winter Park, FL

Chris Creegan · CREEGAN GROUP

Price Reduced20Active

$419,000

4 bd · 2 ba · 1,376 sqft

501 Heritage Blvd, Winter Park, FL

Bernardo Carrasquel · EXP REALTY LLC

Price Reduced9Active

$918,000

4 bd · 3 ba · 2,662 sqft

Lot #21 Karolina Ave, Winter Park, FL

Vinny Lay · COMPASS FLORIDA LLC

1…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

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.