50$625,000
1 bd · 1 ba · 595 sqft
1008 Winter Park Drive 28, Winter Park, CO
Jon Mottern · Serhant Colorado LLC
Homes Under $2M in Winter Park, CO
Hide MapHomes Under $2M in Winter Park, CO
20 of 154 Listings
50$625,000
1 bd · 1 ba · 595 sqft
1008 Winter Park Drive 28, Winter Park, CO
Jon Mottern · Serhant Colorado LLC
63$915,000
2 bd · 2 ba · 1,187.78 sqft
401 Trailhead Circle 434, Winter Park, CO
Team TREC - The Real Estate Company · The Real Estate Company
43$770,000
2 bd · 3 ba · 1,149.2 sqft
78311 US Hwy 40 Ru-Tn-11, Winter Park, CO
Team TREC - The Real Estate Company · The Real Estate Company
41$600,000
2 bd · 2 ba · 940 sqft
214 Gcr 702/Village Dr 1724, Winter Park, CO
Monica D Anderson · Keller Williams Top of the Rockies Grand County
35$1,010,000
3 bd · 3 ba · 1,803 sqft
147 Forest Trail 9, Winter Park, CO
Erin C Jeziorski · Real Estate of Winter Park
45$585,000
2 bd · 2 ba · 899 sqft
51 River Drive 21-16, Winter Park, CO
Team TREC - The Real Estate Company · The Real Estate Company
50$1,240,000
3 bd · 3 ba · 1,507.7 sqft
701 Trailhead Circle #723, Winter Park, CO
Stacy Strayer · Keller Williams Advantage Realty, LLC
37$689,000
3 bd · 2 ba · 1,288 sqft
500 Vasquez Rd #1, Winter Park, CO
Stacy Strayer
50$549,000
1 bd · 1 ba · 595 sqft
1008 Winter Park Drive 31, Winter Park, CO
Jon Mottern
50$815,000
2 bd · 2 ba · 851.2 sqft
78746 US Hwy 40 213, Winter Park, CO
Team TREC - The Real Estate Company · The Real Estate Company
42$499,700
2 bd · 2 ba · 860.4 sqft
490 Kings Crossing Road 331, Winter Park, CO
Monica D Anderson · Keller Williams Top of the Rockies Grand County
25$599,999
1 bd · 1 ba · 649 sqft
510 Baker Drive, Winter Park, CO
Leah Bishop · West and Main Homes
14$534,900
2 bd · 2 ba · 940 sqft
189 Gcr 702 5-203, Winter Park, CO
Erin Life · Keller Williams Advantage Realty, LLC
5$649,500
1 bd · 1 ba · 520 sqft
201 Zephyr Way 2316, Winter Park, CO
Gretchen W Brunke · Playground Destination Property
27$1,099,000
2 bd · 2 ba · 1,376 sqft
97 Kinney Way a, Winter Park, CO
Marcel H Savoie · Equity Colorado, LLC
39$679,000
3 bd · 2 ba · 804 sqft
507 Hi Country #7-87, Winter Park, CO
Julie C Ray · Berkshire Hathaway HomeServices Colorado Real Estate
36$369,900
0 bd · 1 ba · 403 sqft
145 Forest Trail 9, Winter Park, CO
Edmund Rudell · Rudell Realty
27$975,000
3 bd · 3 ba · 1,608.6 sqft
1080 Winter Park Drive 1, Winter Park, CO
Jack M Gerstein · Mountain LifeStyle Realty
33$945,000
3 bd · 2 ba · 1,186 sqft
240 Vasquez Road C-2, Winter Park, CO
Peggy E Smith · Real Estate of Winter Park
34$339,900
1 bd · 1 ba · 349 sqft
411 Hi Country Drive 4-12, Winter Park, CO
Skylar Marshall · Real Estate of Winter Park
Homes Under $2M in Winter Park, CO: 154 active listings as of .
| Property type | Listings | Share |
|---|---|---|
| Condominium | 111 | 72.1% |
| Townhouse | 30 | 19.5% |
| Single Family Residence | 6 | 3.9% |




















Grand County Board of REALTORS
IRES MLS
REcoloradoSource: HJN community data
September 2026 · This period is still settling
Selling at 98.1% of asking price
Buyers here are paying below asking. MLS · 11 sales · as of Sep 29, 2026