48$1,299,000
4 bd · 3 ba · 1,569 sqft
101 Trailhead Circle Unit 124, Winter Park, CO
Brian MacMillan · MacMillan Real Estate Group
Homes for Sale in Winter Park, CO
Hide MapHomes for Sale in Winter Park, CO
15 of 176 Listings
48$1,299,000
4 bd · 3 ba · 1,569 sqft
101 Trailhead Circle Unit 124, Winter Park, CO
Brian MacMillan · MacMillan Real Estate Group
40$1,300,000
4 bd · 5 ba · 2,360 sqft
208 Red Quill Way, Winter Park, CO
Melinda Lee
46$899,000
2 bd · 2 ba · 1,307 sqft
400 Baker Drive Unit Te-103, Winter Park, CO
Stacy Strayer · Keller Williams Advantage Realty, LLC
39$385,000
0 bd · 1 ba · 562.1 sqft
79114 US Hwy 40 Unit E-215, Winter Park, CO
Team TREC - The Real Estate Company · The Real Estate Company
45$1,250,000
3 bd · 3 ba · 1,508 sqft
801 Trailhead Circle 823, Winter Park, CO
Keith A Robinson · WK Real Estate
17$1,718,696
3 bd · 4 ba · 1,761 sqft
135 Spruce Tree Way, Winter Park, CO
Paula Mansfield
18$1,745,015
3 bd · 4 ba · 1,761 sqft
149 Spruce Tree Way, Winter Park, CO
Paula Mansfield
41$1,500,000
3 bd · 4 ba · 1,948 sqft
366 Lake Trail, Winter Park, CO
Melinda Lee · LIV Sotheby's International Realty
40$475,000
2 bd · 2 ba · 860 sqft
490 Kings Crossing Road Unit 321, Winter Park, CO
Team TREC - The Real Estate Company · The Real Estate Company
Price Reduced1$539,000
2 bd · 2 ba · 850 sqft
128 County Road 702 Unit 4-202, Winter Park, CO
Elle Soles
Price Reduced26$395,000
1 bd · 1 ba · 460 sqft
471 Hi Country Dr Unit 166, Winter Park, CO
Marina Dubrova
10$499,000
2 bd · 2 ba · 813.3 sqft
520 Kings Crossing Road a201, Winter Park, CO
David L Jamison · Jamison Mountain Properties
31$355,000
0 bd · 1 ba · 416 sqft
313 Iron Horse Way Unit 2013, Winter Park, CO
Lisa Leclair Waldorf · Real Estate of Winter Park
30$460,000
3 bd · 1 ba · 784 sqft
78679 US Hwy 40 Building 2 Unit 7, Winter Park, CO
Carrie Flynn · Real Estate of Winter Park
Open house Fri, Nov 6 · 1:00 PM50$1,599,000
4 bd · 3 ba · 2,223 sqft
119 Wheeler Rd Unit 4, Winter Park, CO
The Highland Team















Grand County Board of REALTORS
IRES MLS
REcoloradoSource: HJN community data
October 2026 · This period is still settling
Selling at 98.1% of asking price
Buyers here are paying below asking. MLS · 13 sales · as of Oct 30, 2026