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Before you start looking
The buying timeline

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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

5 Bedroom Homes in Winter Park, FL — Page 2

46 listings

5 Bedroom Homes in Winter Park, FL

5 Bedroom Homes in Winter Park, FL

22 of 46 Listings

5 Bedroom Homes in Winter Park, FL

22 of 46 Listings

49Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

$1,800,000

5 bd · 5 ba · 4,029 sqft

281 Brewer Ave, Winter Park, FL

John Henthorn · HENTHORN REAL ESTATE

$2,549,000

5 bd · 5 ba · 3,479 sqft

1823 Sunset Dr, Winter Park, FL

Christopher Christensen · ONE LUXURY INTERNATIONAL LLC

$5,600,000

5 bd · 6 ba · 5,152 sqft

2228 Azalea Pl, Winter Park, FL

Quentin Green, II · COMPASS FLORIDA LLC

$2,995,000

5 bd · 3 ba · 3,523 sqft

1591 Cardinal Court, Winter Park, FL

DJ Diamond · Sunset Lakes Realty

Price Reduced70Active

$2,995,000

5 bd · 7 ba · 4,168 sqft

1836 Whitehall Dr, Winter Park, FL

Bianca Khoury · PREMIER SOTHEBY'S INTL. REALTY

Price ReducedOpen house Sun, Oct 4 · 2:00 PM44Active

$2,050,000

5 bd · 5 ba · 2,889 sqft

240 N Phelps Ave, Winter Park, FL

Nick McKee · KELLER WILLIAMS WINTER PARK

Price Reduced38Active

$1,369,000

5 bd · 4 ba · 2,446 sqft

1473 Berkshire Ave, Winter Park, FL

Gilson Rodrigues · KARDOSH REALTY

$6,000,000

5 bd · 8 ba · 7,397 sqft

1571 Woodland Ave, Winter Park, FL

Vonda Fields · CHARLES RUTENBERG REALTY ORLANDO

$2,375,000

5 bd · 5 ba · 3,989 sqft

946 Enclave Pl, Winter Park, FL

Matthew Burks · CORCORAN PREMIER REALTY

Price Reduced49Active

$1,049,900

5 bd · 5 ba · 3,652 sqft

1448 Lake Florence Way, Winter Park, FL

Abby Nelson · RE/MAX 200 REALTY

$2,475,000

5 bd · 5 ba · 4,150 sqft

926 Enclave Pl, Winter Park, FL

Laura Earl · CORCORAN PREMIER REALTY

$2,300,000

5 bd · 5 ba · 3,865 sqft

938 Enclave Pl, Winter Park, FL

Laura Earl · CORCORAN PREMIER REALTY

$3,300,000

5 bd · 6 ba · 3,421 sqft

1627 Mizell Ave, Winter Park, FL

Bianca Khoury · PREMIER SOTHEBY'S INTL. REALTY

$2,275,000

5 bd · 5 ba · 3,813 sqft

930 Enclave Pl, Winter Park, FL

Matthew Burks · CORCORAN PREMIER REALTY

$2,500,000

5 bd · 6 ba · 4,572 sqft

450 Lakewood Dr, Winter Park, FL

Vonda Fields · CHARLES RUTENBERG REALTY ORLANDO

$1,599,000

5 bd · 4 ba · 3,028 sqft

1864 Grinnell Ter, Winter Park, FL

Robyn Brehne-Glass · COLDWELL BANKER REALTY

Price Reduced48Active

$1,049,000

5 bd · 3 ba · 2,656 sqft

2702 Parkland Dr, Winter Park, FL

Elizabeth Nordquist · NORDQUIST & COMPANY INC

$2,070,000

5 bd · 5 ba · 3,617 sqft

914 Enclave Pl, Winter Park, FL

Matthew Burks · CORCORAN PREMIER REALTY

Price ReducedOpen house Sat, Oct 3 · 11:00 AM68Active

$799,000

5 bd · 3 ba · 2,242 sqft

1927 Eland Ave, Winter Park, FL

Ryan Leitter · CHARLES RUTENBERG REALTY ORLANDO

Price Reduced30Active

$605,000

5 bd · 3 ba · 2,472 sqft

2612 Roxbury Rd, Winter Park, FL

Laura Mcadams · EXP REALTY LLC

Price Reduced12Active

$3,600,000

5 bd · 5 ba · 3,719 sqft

207 E Kings Way, Winter Park, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

Price ReducedOpen house Sat, Oct 3 · 12:00 PM39Active

$3,075,000

5 bd · 6 ba · 3,863 sqft

1821 Englewood Rd, Winter Park, FL

Mick Night · PREMIER SOTHEBY'S INTL. REALTY

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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

Space Coast MLS (Space Coast 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 Space Coast MLS, Inc®. All Rights Reserved. Last Updated: 2026-06-20 07:15:48 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.