First Chair Lair: a proven, turnkey Stratton rental on High Meadow, on the complimentary winter-weekend Stratton shuttle route and about 5 minutes to the base. Two-story great room with brick wood-burning fireplace and cathedral pine ceilings, renovated 2024-25 kitchen and baths, dining for 12, private hot-tub deck, and a lower-level game room (pool table, arcade, darts, foosball). Five bedrooms including a king suite with soaking tub, a fireplace queen, and a bunk room; 4 full baths; 2-car garage; town water and sewer. INCOME: $158,731 gross in 2025; $147,057 trailing 12 months; about $115,000 in confirmed future bookings on the books (11 stays, including long winter stays). Currently marketed for 8 guests; capacity can increase to 12 with a fire-alarm system upgrade (quote on file). Sold fully furnished with bookings, website presence and optional continued professional management by 42 North. 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 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

  • PricePerSqFt411.97

Tax Information

  • Tax Year2026

Parking

  • Parking Spaces2
  • GarageYes
  • Parking DescriptionDriveway, Garage

Rooms

  • Full Bath4

Basic Information

  • MLS Number5111779
  • MLS StatusActive
  • StatusACT
  • Property TypeSingle Family
  • List Price$1,500,000
  • Listing Agent NameDavid Powers
  • Broker Name42 North LP

Location

  • Building Number180
  • StreetHigh Meadow Road
  • TownWinhall
  • StateVT
  • Zip05340
  • CountyBennington
  • SubdivisionHigh Meadows
  • DistrictWinhall School District
  • Flood Zone Y/NUnknown
  • Address180 High Meadow Road

Building

  • Year Built1987
  • Building ConstructionWood Frame, Cedar Exterior
  • ConstructionExisting
  • Property StyleContemporary
  • Bedrooms5
  • Bathroom4
  • Total Baths4
  • Total Rooms9
  • Square Feet4,173
  • APX Unfin Below Grade651
  • BasementPartially Finished
  • FoundationPoured Concrete

Property

  • Acreage1
  • Lot DescriptionCountry Setting, Mountain View, Ski Area, Wooded, Near Golf Course, Near Skiing
  • AreaVT-Bennington
  • DrivewayGravel
  • RoadsPaved, Privately Maintained

Interior

  • Interior FeaturesCathedral Ceiling, Wood Fireplace,2 Fireplaces, Furnished, Hot Tub, Kitchen/Dining, Primary BR w/ BA, Walk-in Closet,1st Floor Laundry
  • FloorsCarpet, Hardwood, Tile
  • Stories2

Exterior

  • Exterior FeaturesDeck, Hot Tub, Porch
  • RoofAsphalt Shingle

Utilities

  • Heat SystemOil, Wood, Baseboard, Hot Water, Mini Split
  • WaterPublic
  • SewerPublic
  • ElectricCircuit Breaker(s)
  • UtilitiesOther

Amenities

  • PetsYes

Other

  • SeasonalNo
  • Page627
  • 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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