New Listing
180 High Meadow Road,Winhall, VT 05340
Winhall, VT 05340
Description
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.
Details
| MLS # | 5111779 |
|---|---|
| Listing Type | For Sale |
| Style | House |
| Sub-Type | Resale |
| Status | (10) Active - Active |
| Year | 1987 |
| Days On Site | 1 |
| Listing Provided By | 42 North LP | David Powers |
Features
| Bed(s) | 5 |
|---|---|
| Bath(s) | 4 Total |
| Garage | 2 |
| Basement | Y |
| Story(s) | 2 |
| Zoning | Residential |
| Acreage | 1.00 |
Interior
| Rooms Total | 9 |
|---|---|
| Cooling | Ductless, Mini Split |
| Heating | Oil, Wood, Baseboard, Hot Water, Mini Split |
| Interior Features | Cathedral Ceiling(s), Wood Fireplace, 2 Fireplaces, Furnished, Hot Tub, Kitchen/Dining, Primary BR w/ BA, Walk-In Closet(s), 1st Floor Laundry |
| Appliances | Dishwasher, Dryer, Microwave, Refrigerator, Washer |
Exterior
| Exterior Features | Deck, Hot Tub, Porch |
|---|---|
| Roof | Asphalt Shingle |
| Construction Materials | Wood Frame, Cedar |
| Foundation Details | Poured Concrete |
| Lot Features | Country Setting, Mountain View, Ski Area, Wooded, Near Golf Course, Near Skiing |
Parking
| Garage Yes / No | Yes |
|---|---|
| Parking Features | Driveway, Garage |
Utilities
| Utilities | Other |
|---|---|
| Electric | Circuit Breakers |
| Sewer | Public |
Taxes
| Tax Annual Amount | 16138.59 |
|---|---|
| Tax Assessed Value | 1051100 |
| Tax Year | 2026 |
Area Information
| State | VT |
|---|---|
| County | Bennington |
| City | Winhall |
| Zip Code | 05340 |
| Area | VT Bennington |
| Community Name | High Meadows |
| School District | Winhall School District |
| Listing VS Median (in High Meadows) | |
Price: $1,500,000 low | high Med: $0 On site: 1 low | high Med: | |
Market Activity 05340
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Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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.
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Learn More About This Property
| State | VT |
|---|---|
| County | Bennington |
| City | Winhall |
| Zip Code | 05340 |
| Area | VT Bennington |
| Community Name | High Meadows |
| School District | Winhall School District |
| Listing VS Median (in High Meadows) | |
Price: $1,500,000 low | high Med: $0 On site: 1 low | high Med: | |
 | $2,250,000165 High Meadow RoadWinhall, VT 05340 |
 | $2,350,0006 Sunset Ridge RoadWinhall, VT 05340 |
Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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.
