Browse All Winter Park CO Historical Properties for Sale

Don't miss this opportunity to own an affordable 3-bedroom condo in the heart of downtown Winter Park! Thoughtfully updated and fully furnished, this charming mountain retreat is move-in ready and waiting for the 2026-2027 ski season. Warm up after a day on the slopes beside the striking wood-burning fireplace, or relax and enjoy the abundant natural light that fills the home through large windows overlooking mature trees. The unbeatable location puts you just steps from live music, shopping, restaurants, festivals, and everything downtown Winter Park has to offer. Whether you're looking for a weekend getaway, vacation home, or investment property, this turnkey condo offers the perfect combination of comfort, convenience, and mountain lifestyle.

432 Hi Country Drive Unit 10-13, Winter Park

$480,000

3 Beds ⋅ 1 Baths ⋅ 26-1031 MLS

Quietly tucked along the Fraser River in central downtown Winter Park sits a bright end unit, 3 bedroom/ 1 bath condo. This condo is waiting for someone to update and create their own vision. Hanging cabinets and range have been removed and not replaced. The building features an impressive new deck and stairs with a peaceful riverfront garden gathering/sitting area. Roof replaced July 2026. Ideally located for those who want to be in the middle of downtown yet peacefully removed from the hustle of it. The sound of the river will be all you hear with windows open or enjoying some time on the deck out front of your mountain getaway.

78679 Us Hwy 40 Unit Building 2 unit 7, Winter Park

$405,000

1 Beds ⋅ 1 Baths ⋅ 26-920 MLS

See Supplemental Remarks Why drive back to Denver after a long day on the mountain when you can retreat to your own turnkey Winter Park getaway? Welcome to 400 Hi Country Drive #155, a beautifully updated top-floor 1-bedroom, 1-bathroom condo ideally situated along the Fraser River in the heart of downtown Winter Park. This well-maintained mountain retreat offers comfort, convenience, and investment potential, with short-term rentals allowed. Inside, you'll find an inviting open-concept floor plan featuring hard-surface flooring throughout, a wood-burning fireplace, updated bathroom, two new ceiling fans and brand-new stainless steel kitchen appliances. The open kitchen includes ample prep space and bar seating, making it easy to gather after a day of adventure. Head outside onto the deck and enjoy the soothing sounds of the Fraser River, stunning alpenglow views, and convenient exterior storage for all your mountain gear. Whether you've spent the day skiing, biking, hiking, or exploring Grand County, this condo provides the perfect place to unwind. Owners and guests enjoy access to Hi Country Haus amenities, including a recreation center with an indoor pool, hot tubs, fitness center, game room, community gathering spaces, picnic and grilling areas and convenient laundry facilities. Heat, water, cable, internet and clubhouse access are included in the HOA dues. Just moments from downtown Winter Park's restaurants, shops, breweries, live music at Hideaway Park, bowling, and year-round events. The free Lift shuttle stops across the street, providing easy access to Winter Park Resort and world-class skiing. Miles of hiking, biking, and cross-country trails are just moments away, making this a true four-season destination. Whether you're searching for a full-time residence, a mountain escape, or an income-producing investment property, this move-in-ready condo delivers an unbeatable combination of location, amenities, and mountain charm in one of Winter Park's most desirable settings.

400 Hi Country Drive Unit 155, Winter Park

$682,000

3 Beds ⋅ 2 Baths ⋅ 26-805 MLS

Top-floor, move-in ready, and steps from everything Winter Park has to offer. Updated 3-bedroom, 2-bath condo at Hi Country Haus is a rare find that works equally well as a full-time residence, mountain getaway, or income-producing investment. Inside, a bright, open living space centers on a cozy fireplace, with natural light pouring in from the top-floor vantage point. The updated kitchen brings contemporary finishes, stainless steel appliances, and generous storage to the everyday. The primary suite offers a private retreat with a fully renovated en-suite bath, while two additional bedrooms - both served by a second beautifully updated bathroom - flex easily into guest space, family space, or a home office. HCH residents enjoy resort-style amenities: a clubhouse, pool, hot tubs, and fitness center. The location does the rest of the work as it's walkable to Winter Park, trails, restaurants, and entertainment, with a free shuttle stop nearby for easy, car-free access to the Resort and town. Rarely available and ready to enjoy from day one.

518 Hi Country Drive Unit #13-148, Winter Park

$2,449,000

4 Beds ⋅ 3 Baths ⋅ 26-699 MLS

An exceptional opportunity in the heart of Winter Park. This commercially zoned property boasts an UNBEATABLE LOCATION across from Cooper Creek Square, with private frontage on Vasquez Creek and just one property from the town's future gondola. Designed for easy main-level living, the 4-bedroom, 3-bath home features a remodeled chef's kitchen with Viking and Thermador appliances, pantry/laundry, and a main-floor primary suite with French doors which leads to the expansive covered deck where you'll find an outdoor kitchen, hot tub, fire pit, tree house, detached tiny office, towering pines, wildlife, and the soothing sounds of the creek. Tucked behind the oversized garage is a luxurious office with abundant natural light overlooking the creek, and another bath. Finally, a separate charming cabin with a small deck that sits in front of the property: perfect for guests, incredible rental income, or even a caretaker home. This property is zoned Destination Center (D-C) on .26 acres located one block from HWY 40, having close distance to downtown Winter Park amenities, transit and Winter Park Resort access. D-C zoning allows high density residential and mixed use development, subject to the Town of Winter Park approval. Buyer to verify zoning, share potential development plans and uses with the Town of Winter Park. This is a must-see property for homeowners and investors alike.

115 Lions Gate Drive, Winter Park

$325,000

1 Baths ⋅ 26-553 MLS

Own a Winter Park mountain residence with the service standards of a Marriott Tribute Portfolio Hotel. The newly constructed Queen + Sleeper Studio Residence at Jane's Edge offers 90 floating days of owner use each year in Winter Park, designed for buyers who want mountain access, easy ownership, and a professionally managed hotel residence structure. Use your time across ski season, summer, or quiet mountain getaways, then leave knowing operations and guest services are handled at a hotel level. When you are not using the residence, it is placed into the hotel-managed rental program, creating a true lock-and-leave ownership experience. Join the reservation list: https://www.residencesatjanesedge.com Prices will range from $325,000 $505,00 for standard king/queen rooms. We will be releasing 20 units on the 2nd floor to purchase in mid-June, with closings estimated in the late fall. However, the first step is to make a Reservation and the link above. Please review the reservation details below. Marriott Bonvoy Benefits & Purchase Process: https://www.residencesatjanesedge.com/terms-conditions.htm Jane's Edge is designed to function like a true hotel residence, with amenities that support both personal use and guest comfort. Owners and guests enjoy an indoor pool, hot tubs, owner's lounge, concierge services, ski lockers, transportation to and from Winter Park Resort and town, on-site laundry, sauna and steam room, fitness center, outdoor patio, firepit, gathering area, full restaurant and bar, ballroom, private meeting spaces, and wedding/event venue options. In-room upgrades include a refrigerator with freezer compartment, wet bar, coffee/tea maker, clothes steamer, hair dryer, alarm clock, HDTV with cable, high-speed internet/WiFi, and power and data ports. Floor-level microwaves and toaster ovens add extra convenience for longer stays. We anticipate closing on the residences in Q4 2026. At that time, your residence will become available for use.

81699 Us Hwy 40 Unit Queen+Sleeper, Winter Park

$325,000

1 Baths ⋅ 26-552 MLS

Own a Winter Park mountain residence with the service standards of a Marriott Tribute Portfolio Hotel. The newly constructed King Studio Residence at Jane's Edge offers 90 floating days of owner use each year in Winter Park, designed for buyers who want mountain access, easy ownership, and a professionally managed hotel residence structure. Use your time across ski season, summer, or quiet mountain getaways, then leave knowing operations and guest services are handled at a hotel level. When you are not using the residence, it is placed into the hotel-managed rental program, creating a true lock-and-leave ownership experience. Join the reservation list: https://www.residencesatjanesedge.com Prices will range from $325,000 $505,00 for standard king/queen rooms. We will be releasing 20 units on the 2nd floor to purchase in mid-June, with closings estimated in the late fall. However, the first step is to make a Reservation and the link above. Please review the reservation details below. Marriott Bonvoy Benefits & Purchase Process: https://www.residencesatjanesedge.com/terms-conditions.htm Jane's Edge is designed to function like a true hotel residence, with amenities that support both personal use and guest comfort. Owners and guests enjoy an indoor pool, hot tubs, owner's lounge, concierge services, ski lockers, transportation to and from Winter Park Resort and town, on-site laundry, sauna and steam room, fitness center, outdoor patio, firepit, gathering area, full restaurant and bar, ballroom, private meeting spaces, and wedding/event venue options. In-room upgrades include a refrigerator with freezer compartment, wet bar, coffee/tea maker, clothes steamer, hair dryer, alarm clock, HDTV with cable, high-speed internet/WiFi, and power and data ports. Floor-level microwaves and toaster ovens add extra convenience for longer stays. We anticipate closing on the residences in Q4 2026. At that time, your residence will become available for use.

81699 Us Hwy 40 Unit King, Winter Park

$450,000

2 Beds ⋅ 1 Baths ⋅ 26-517 MLS

End-unit condo overlooking the Fraser River in the heart of Winter Park. This fully furnished 2BR/1BA is truly turnkey--ideal as a personal retreat or investment with STR's allowed. Enjoy cozy winter nights by the wood fireplace and take in the sounds of the river and alpenglow views from the deck. Plenty of room for gear in the storage locker on the deck. Fun for everyone with modern Clubhouse, pool, 3 hot tubs, fitness area, and game room and laundry room! Hop on the bus to WP or hop on your bike to miles of trails. Building 6 is quiet and the well-managed HOA takes care of everything; heat, cable, wifi and more! Pet friendly! Strong reserves and New Boiler! Live your Colorado dream in this sweet condo, in the heart of WP. Year round mountain adventure awaits! Amazing location close to downtown, Hideaway Park concerts and more! Hop on the free shuttle to Winter Park Resort for world-class skiing. Set in a quiet, well-maintained building with ample parking, just moments from downtown dining, live music, bowling, and more--this is effortless mountain living in a location that delivers year-round adventure.

471 Hi Country Drive Unit 611, Winter Park

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