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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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What's my home worth?
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Get an instant cash offer
Buy before you sell

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What's worth fixing first
Find a seller's agent

3 beds New construction With a pool

5 Bedroom Homes in Winter Park, FL

38 listings

5 Bedroom Homes in Winter Park, FL

5 Bedroom Homes in Winter Park, FL

24 of 38 Listings

5 Bedroom Homes in Winter Park, FL

24 of 38 Listings

11Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

$3,195,000

5 bd · 6 ba · 4,139 sqft

2119 Howard Dr, Winter Park, FL

Laura Earl · CORCORAN PREMIER REALTY

$1,950,000

5 bd · 5 ba · 3,560 sqft

513 Dunraven Dr, Winter Park, FL

Alison Mosley · PREMIER SOTHEBY'S INTL. REALTY

$780,000

5 bd · 3 ba · 2,194 sqft

739 Roughbeard Rd, Winter Park, FL

John Harbuck · SERHANT

$6,195,000

5 bd · 6 ba · 5,096 sqft

698 N New York Ave, Winter Park, FL

Mick Night · PREMIER SOTHEBY'S INTL. REALTY

$2,990,000

5 bd · 5 ba · 4,050 sqft

532 Langholm Dr, Winter Park, FL

Christopher Christensen · ONE LUXURY INTERNATIONAL LLC

$3,495,000

5 bd · 6 ba · 4,478 sqft

662 Granville Drive, Winter Park, FL

Nathalie Bates · PREMIER SOTHEBY'S INTL. REALTY

$6,995,000

5 bd · 6 ba · 5,479 sqft

901 Golfview Ter, Winter Park, FL

Mick Night · PREMIER SOTHEBY'S INTL. REALTY

$5,500,000

5 bd · 7 ba · 5,181 sqft

1166 Palmer Ave, Winter Park, FL

Prentice Williams · KELLER WILLIAMS ADVANTAGE REALTY

$4,325,000

5 bd · 5 ba · 4,853 sqft

250 W Reading Way, Winter Park, FL

Brian Mitnik · RE/MAX 200 REALTY

$5,195,900

5 bd · 7 ba · 5,122 sqft

825 Palmer Ave, Winter Park, FL

Laura Earl · CORCORAN PREMIER REALTY

$2,725,000

5 bd · 5 ba · 3,784 sqft

1773 Walnut Ave, Winter Park, FL

Christopher Christensen · ONE LUXURY INTERNATIONAL LLC

$3,395,000

5 bd · 6 ba · 4,015 sqft

160 W Rockwood Way, Winter Park, FL

Alison Mosley · PREMIER SOTHEBY'S INTL. REALTY

Price Reduced69Active

$775,000

5 bd · 4 ba · 2,840 sqft

1164 Dodd Road, Winter Park, FL

Michael John Rothenburg · Charles Rutenberg Realty FTL

$3,265,000

5 bd · 6 ba · 4,949 sqft

1761 Legion Dr, Winter Park, FL

Harry Pool, III · COLDWELL BANKER REALTY

Open house Fri, Oct 2 · 2:00 PM27Active

$1,574,900

5 bd · 5 ba · 3,252 sqft

1526 Miller Ave, Winter Park, FL

Kim Griffin · RE/MAX EXCLUSIVE COLLECTION

$860,000

5 bd · 4 ba · 3,284 sqft

120 Longbranch Rd, Winter Park, FL

Karen Albright · OPENDOOR BROKERAGE LLC

$2,700,000

5 bd · 5 ba · 3,588 sqft

648 Worthington Dr, Winter Park, FL

Christopher Christensen · ONE LUXURY INTERNATIONAL LLC

$1,625,000

5 bd · 5 ba · 3,133 sqft

2407 Lafayette Ave, Winter Park, FL

Lisa Fleming · FANNIE HILLMAN & ASSOCIATES

$4,650,000

5 bd · 6 ba · 4,827 sqft

857 Brock St, Winter Park, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

$2,299,000

5 bd · 5 ba · 2,868 sqft

1840 Laurel Rd, Winter Park, FL

Matt Tomaszewski · CORCORAN PREMIER REALTY

$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

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

1 2

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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

BeachesMLS: All listings featuring the BMLS logo are provided by Beaches MLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Information is provided exclusively for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Listing information ©2026 Beaches Multiple Listing Service®. All Rights Reserved. Data Last Updated: 2026-10-01 15:48:25 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.