165 High Meadow Road Winhall, VT $ 2,250,000
165 High Meadow Road
$ 2,250,000
Recently Listed
Share Save

165 High Meadow Road

Winhall, VT, 05340
$ 2,250,000
Bedrooms4 Baths4.1 Sq 3,034

Monthly Estimate*

$ 14,207

Listed by David Powers, 42 North LP, 802-214-2714, david@42n.homes
165 High Meadow Road, Winhall, VT 05340 - Image 1
165 High Meadow Road, Winhall, VT 05340 - Image 2
165 High Meadow Road, Winhall, VT 05340 - Image 3
165 High Meadow Road, Winhall, VT 05340 - Image 4
165 High Meadow Road, Winhall, VT 05340 - Image 5
165 High Meadow Road, Winhall, VT 05340 - Image 6
165 High Meadow Road, Winhall, VT 05340 - Image 7
165 High Meadow Road, Winhall, VT 05340 - Image 8
165 High Meadow Road, Winhall, VT 05340 - Image 9
165 High Meadow Road, Winhall, VT 05340 - Image 10
165 High Meadow Road, Winhall, VT 05340 - Image 11
165 High Meadow Road, Winhall, VT 05340 - Image 12
165 High Meadow Road, Winhall, VT 05340 - Image 13
165 High Meadow Road, Winhall, VT 05340 - Image 14
165 High Meadow Road, Winhall, VT 05340 - Image 15
165 High Meadow Road, Winhall, VT 05340 - Image 16
165 High Meadow Road, Winhall, VT 05340 - Image 17
165 High Meadow Road, Winhall, VT 05340 - Image 18
165 High Meadow Road, Winhall, VT 05340 - Image 19
165 High Meadow Road, Winhall, VT 05340 - Image 20
165 High Meadow Road, Winhall, VT 05340 - Image 21
165 High Meadow Road, Winhall, VT 05340 - Image 22
165 High Meadow Road, Winhall, VT 05340 - Image 23
165 High Meadow Road, Winhall, VT 05340 - Image 24
165 High Meadow Road, Winhall, VT 05340 - Image 25
165 High Meadow Road, Winhall, VT 05340 - Image 26
165 High Meadow Road, Winhall, VT 05340 - Image 27
165 High Meadow Road, Winhall, VT 05340 - Image 28
165 High Meadow Road, Winhall, VT 05340 - Image 29
165 High Meadow Road, Winhall, VT 05340 - Image 30
165 High Meadow Road, Winhall, VT 05340 - Image 31
165 High Meadow Road, Winhall, VT 05340 - Image 32
165 High Meadow Road, Winhall, VT 05340 - Image 33
165 High Meadow Road, Winhall, VT 05340 - Image 34
165 High Meadow Road, Winhall, VT 05340 - Image 35
165 High Meadow Road, Winhall, VT 05340 - Image 36
165 High Meadow Road, Winhall, VT 05340 - Image 37
165 High Meadow Road, Winhall, VT 05340 - Image 38
165 High Meadow Road, Winhall, VT 05340 - Image 39
165 High Meadow Road, Winhall, VT 05340 - Image 40

Single Family Home for sale in Winhall, VT

for $2,250,000 with 4 bedrooms and 4 full baths, 1 half bath. This 3,034 square foot home was built in 1988 on a lot size of 1.08.

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 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.

See more

Single Family Active

Price

$ 2,250,000

Bedrooms

4

Full Bath

4

Half Bath

1

Property Type

Single Family

Taxes

$ 0

Style

Contemporary,Walkout Lower Level

Lot Size

1.08

Year Built

1988

Town/City

Winhall

County/Region

Bennington

MLS | Web ID

5111781

Features
Interior
Basement Description Finished Walkout
Interior Amenities Wood Fireplace 1 Fireplace Furnished Hot Tub Kitchen/Dining Primary BR w/ BA Sauna Wet Bar
Basement Yes
Flooring Carpet Hardwood Tile
Beds 4
Total Rooms 8
Total Number of Units 1
See more
General
Road Frontage TBD
Sewer Public
Heating Oil Solar Baseboard Heat Pump Hot Water
Cooling Central AC
Utilities Other
Possession At Closing
Roof Asphalt Shingle
Appliances Dishwasher Dryer Microwave Refrigerator Washer
Pets Allowed Yes
Garage Yes
Flood Zone Unknown
Zoning Residential
3/4 Baths 0
Full Baths 4
Half Baths 1
Bathrooms 5
Year Built 1988
Electric Circuit Breaker(s)
Subdivision High Meadows
Style Contemporary Walkout Lower Level
Stories Count 2
Type Single Family
Property Condition Existing
Assessment Amount 993800
Tax Year 2026
Status Detail 0
Covenants Yes
Construction Materials Wood Frame Wood Siding
Directions Route 30 to Stratton Mountain Road then to High Meadow Road; number 165.
City Winhall
School District Winhall School District
Seasonal No
DOM 2
Price Per Sq Ft Total AG 1066.35
See more
Exterior
Lot Features Mountain View Ski Area Wooded Near Golf Course Near Skiing
Exterior Amenities Deck Hot Tub Patio In-Ground Pool Sauna
Driveway Common/Shared Gravel
Lot Size Area 1.08
Water Source Public
Parking Features Driveway Garage
Garage Capacity 2
Foundation Poured Concrete
Lot E-12R
See more
* Excluded Features
List By
David Powers

Listing Agent

42 North Lp

Broker

(802) 214-2714

Phone

david@42n.homes

Email

Affordability Calculator

$14,207
Per Month
100%
0%
0%
Monthly Principal & Interest
$14,207
Monthly Property Taxes
--
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
5572120 Elementary School
5554171 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
9/28/2026$2,250,000 Listed Price

Map


See all

165 High Meadow Road, Winhall, VT, 05340 is a Single Family Home for sale at $2,250,000 with 3,034 sqft and a lot size of 1.08. 165 High Meadow Road has 4 bedrooms, 4.1 baths, and was built in 1988. The property's zip code is 05340 which is in Winhall, VT