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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

Resources

How selling works
When should I sell?
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Pricing your home
What's worth fixing first
Find a seller's agent

3 beds New construction With a pool

4 Bedroom Homes in Winter Park, CO

8 listings

4 Bedroom Homes in Winter Park, CO

4 Bedroom Homes in Winter Park, CO

8 Listings

4 Bedroom Homes in Winter Park, CO

8 Listings

49Active

Your local brokerage

SM

Steve Merritt

Realty.com

Lic. #ER.100044960

$1,350,000

4 bd · 3 ba · 1,569 sqft

101 Trailhead Circle 124, Winter Park, CO

Brian MacMillan · MacMillan Real Estate Group

$1,650,000

4 bd · 4 ba · 2,046.88 sqft

94 Trademark Drive, Winter Park, CO

Team TREC - The Real Estate Company · The Real Estate Company

$622,500

4 bd · 3 ba · 1,762.7 sqft

78415 US Hwy 40 5, Winter Park, CO

Nazreen Kashani · LIV Sotheby's International DT

$1,238,500

4 bd · 3 ba · 1,588 sqft

201 Trailhead Circle 234, Winter Park, CO

Marian A Waldron · Coldwell Banker Mtn Properties

$1,245,000

4 bd · 3 ba · 1,762.7 sqft

78415 US Hwy 40 5, Winter Park, CO

Nazreen Kashani · LIV Sotheby's International DT

$2,350,000

4 bd · 6 ba · 2,807 sqft

385 Lions Gate Drive G, Winter Park, CO

Skylar Marshall · Real Estate of Winter Park

$1,875,000

4 bd · 6 ba · 2,824 sqft

385 Lions Gate Drive B, Winter Park, CO

Skylar Marshall · Real Estate of Winter Park

$2,150,000

4 bd · 6 ba · 2,807 sqft

385 Lions Gate Drive C, Winter Park, CO

Skylar Marshall · Real Estate of Winter Park

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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

SM

Steve Merritt

Realty.com

Lic. #ER.100044960

Listing data & MLS disclosures

Grand County Board 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 Grand County Board of Realtors, Inc®. All Rights Reserved. Last Updated: 2026-09-14 22:11:48 UTC

Winter Park, CO community profile

Population: 1,066
Median income: $72,015
Housing units: 1,726
People per sq. mi.: 15
Area: 71.3 sq. mi.

Source: HJN community data

Winter Park housing market

August 2026

Selling at 98.7% of asking price

Buyers here are paying below asking. MLS · 17 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $1,160,000$623,500–$1,825,000 typical range
Price per sq. ft.: $712
Sales: 22
Paid in cash: 40.9%

Homes on the market · MLS, as of Aug 31, 2026

Median list price: $985,000
Homes for sale: 167

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -34.3%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,498 sq. ft.