Property Description
Trailhead Lodges at Winter Park
Trailhead Lodges at Winter Park is the premier address in downtown Winter Park. Directly behind Hideaway Park and one block from the main road, it is the ideal location to walk to all of downtown Winter Park’s shops, restaurants and activities. It is only a short shuttle ride to Winter Park Ski Resort.
Trailhead Lodges has one, two and three bedroom condominiums in 8 buildings. It has a clubhouse with pool, hot tub exercise room and meeting room.
Trailhead Lodges
Property Details
Property Name
Trailhead Lodges
Property Type
Condominiums
Location
Winter Park Downtown
Lots / Units
96
Sizes*
One, two & three bedroom units
Water / Sewer
municipal
Mgmt Co.
municipal
HOA Name
Trailhead Lodges
HOA Dues Range
varies
Amenities
Swimming Pool, Hot Tub & Clubhouse
Features
Located in the heart of downtown Winter Park right behind Hideaway Park
Property Images
Trailhead Lodges units for sale
5
matches found
Listings Per Page
5 10 15 20 25
Sort By
List price (High to Low) List price (Low to High) # Bedrooms # Bathrooms Year Built Square Footage Recently Updated
$675,000
# of Bedrooms: 1
# of Bathrooms: 1
Square Footage: 899.8
Year Built: 2008
Area: Winter Park Area
Subdivision: TRAILHEAD LODGES
Description: Opportunities like this don't come along often. This 1-bedroom, 1-bath cond...
Last Updated: July - 13 - 2026
IDX
$880,000
# of Bedrooms: 2
# of Bathrooms: 2
Square Footage: 1284.25
Year Built: 2008
Area: Winter Park Area
Subdivision: TRAILHEAD LODGES
Description: Turnkey and ready for its next owners, this spacious 2-bedroom condo offers...
Last Updated: July - 13 - 2026
IDX
$895,000
# of Bedrooms: 2
# of Bathrooms: 2
Square Footage: 1286.77
Year Built: 2008
Area: Winter Park Area
Subdivision: TRAILHEAD LODGES
Description: This Trailhead Lodge top floor unit is located in the heart of downtown Win...
Last Updated: July - 07 - 2026
IDX
$1,238,500
# of Bedrooms: 4
# of Bathrooms: 3
Square Footage: 1862
Year Built: 2015
Area: Winter Park Area
Subdivision: TRAILHEAD LODGES
Description: Welcome to this spectacular 4-bedroom (1 non-conforming), 3-bath spacious c...
Last Updated: July - 07 - 2026
IDX
$1,250,000
# of Bedrooms: 3
# of Bathrooms: 3
Square Footage: 1558
Year Built: 2008
Area: Winter Park Area
Subdivision: TRAILHEAD LODGES
Description: Enjoy the best of mountain living and investment potential with this beauti...
Last Updated: July - 07 - 2026
IDX
Information deemed reliable but not guaranteed.
