Winhall, VT | 165 High Meadow Road

Christie's International Real Estate
$2,250,000
MLS#: 5111781
3,034
Sq Ft
1.08
Acres
5
Baths
4
Bedrooms
General Property Information
Property Status
Active
Price
$2, 250, 000
Property Type
Single Family
County
VT-Bennington
Agency / Brokerage
David Powers
42 North LP
List Date
9/27/2026 8:00 PM
Assessed
$993,800
Assessed Year
2026
Acres
1.08
Year Built
1988
Bedrooms
4
Total Baths
5
Sq. Ft. (Total)
3,034
Tax Year
2026
Taxes
$15,259

Description

Wandering Moose: a rare heated-pool ski house on High Meadow, on the Stratton winter shuttle route. Rebuilt top to bottom in 2024 with a designer interior, then finished with a heated in-ground pool (2025), hot tub, barrel sauna, Level 2 EV charger and rooftop solar. Open great room with stone wood-burning fireplace and indoor swing, open kitchen and dining, walkout lower level with wet bar and arcade, 4 bedrooms and 4.5 baths. One of the only private heated-pool rentals near Stratton, and it earns like it: $155, 716 gross in 2025 and $216, 999 trailing 12 months; about $102, 000 in confirmed future bookings on the books (9 stays). GOLF-COURSE ESTATE OPPORTUNITY: the seller also owns the adjoining Indian Paint Brush building lots (Lots E-13R & E-14R, 2.48± ac), which abut the Stratton golf course and are listed separately at $500, 000. Buy both: live in or rent the Moose while you build your estate next door. Featured on the Destination Channel's Staycation TV program. PORTFOLIO FOR SALE: This property is one of five 42 North properties in Winhall offered individually or together (four turnkey short-term rentals + the Indian Paint Brush building lot; ~$560K combined trailing-12-month gross rental revenue). Ask about package pricing. Listing broker David Powers is a principal and beneficial owner of the selling entity. Potential tax advantages for STR buyers (non-passive treatment, cost segregation, bonus depreciation) - consult your tax advisor. Revenue figures are gross rental revenue excluding taxes, before expenses; unaudited; past results do not guarantee future results.

Map

Interior Features
# Of Stories
2
Sq. Ft. (Total)
3,034
Sq. Ft. (Above Ground)
2,110
Sq. Ft. (Below Ground)
924
Rooms
8
Bedrooms
4
Baths
5
Interior Desc
Wood Fireplace, 1 Fireplace, Furnished, Hot Tub, Kitchen/Dining, Primary BR w/ BA, Sauna, Wet Bar
Appliances Included
Dishwasher, Dryer, Microwave, Refrigerator, Washer
Flooring
Carpet, Hardwood, Tile
Heating
Oil, Solar, Baseboard, Heat Pump, Hot Water
Basement Desc
Finished, Walkout

Town Market Snapshot

Source: Data provided by PrimeMLS, graph generated by Pall Spera Company

Exterior Features
Style of Residence
Contemporary, Walkout Lower Level
Time Share
No
Exterior Details
Deck, Hot Tub, Patio, In-Ground Pool, Sauna
Land Desc.
Mountain View, Ski Area, Wooded, Near Golf Course, Near Skiing
Roof Desc.
Asphalt Shingle
Driveway Desc.
Common/Shared, Gravel
Foundation Desc.
Poured Concrete
Sewer Desc.
Public
Garage / Parking
Yes
Garage Spaces
2
Road Frontage
0
Zoning
Residential

Affordability Estimate

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