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.

Listing Tools

More Info

Basic Information

  • PricePerSqFt1066.35

Tax Information

  • Tax Year2026

Parking

  • Parking Spaces2
  • GarageYes
  • Parking DescriptionDriveway, Garage

Rooms

  • Full Bath4

Basic Information

  • MLS Number5111781
  • MLS StatusActive
  • StatusACT
  • Property TypeSingle Family
  • List Price$2,250,000
  • Listing Agent NameDavid Powers
  • Broker Name42 North LP

Location

  • Building Number165
  • StreetHigh Meadow Road
  • TownWinhall
  • StateVT
  • Zip05340
  • CountyBennington
  • SubdivisionHigh Meadows
  • DistrictWinhall School District
  • Flood Zone Y/NUnknown
  • Address165 High Meadow Road

Building

  • Year Built1988
  • Building ConstructionWood Frame, Wood Siding
  • ConstructionExisting
  • Property StyleContemporary, Walkout Lower Level
  • Bedrooms4
  • Bathroom5
  • Total Baths5
  • Half Bath1
  • Total Rooms8
  • Square Feet3,034
  • BasementFinished, Walkout
  • FoundationPoured Concrete

Property

  • Acreage1.08
  • Lot DescriptionMountain View, Ski Area, Wooded, Near Golf Course, Near Skiing
  • AreaVT-Bennington
  • LotE-12R
  • DrivewayCommon/Shared, Gravel
  • RoadsPaved, Privately Maintained

Interior

  • Interior FeaturesWood Fireplace,1 Fireplace, Furnished, Hot Tub, Kitchen/Dining, Primary BR w/ BA, Sauna, Wet Bar
  • FloorsCarpet, Hardwood, Tile
  • Stories2

Exterior

  • Exterior FeaturesDeck, Hot Tub, Patio, In-Ground Pool, Sauna
  • RoofAsphalt Shingle

Utilities

  • Heat SystemOil, Solar, Baseboard, Heat Pump, Hot Water
  • WaterPublic
  • SewerPublic
  • ElectricCircuit Breaker(s)
  • UtilitiesOther

Amenities

  • PetsYes

Other

  • SeasonalNo
  • Page241
  • Date Listed09/28/2026

Map Location

Listed by David Powers of 42 North LP
Broker Reciprocity 

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated September 28, 2026 2:24 PM UTC

 

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