Deb Rees
REALTOR®
BEDS4
BATHS4 full 1 partial
SQUARE FEET3,034
MLS#5111781
STATUSActive
PROPERTY TYPEResidential - Single Family
SUBDIVISIONHigh Meadows
SCHOOLWinhall
Listing Courtesy of:
42 North LP
Agency Phone: 802-214-2714
Associate Name: David Powers
Property 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. 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.
Property Features
Property Type: Residential - Single Family
Basement: Yes
Basement: Finished, Walkout
Cooling: Central AC
Garage: 2
Heating: Oil, Solar, Baseboard, Heat Pump, Hot Water
Home Style: Contemporary, Walk-Out
Lot Size: 1.08 Acres
Roof Type: Asphalt Shingle
Stories: 2.0
Taxes: $15,258
Year Built: 1988
Amenities
Wood Fireplace
1 Fireplace
Furnished
Hot Tub
Kitchen/Dining
Primary BR w/ BA
Sauna
Wet Bar
Deck
Hot Tub
Patio
In-Ground Pool
Sauna
Feature Descriptions
Appliances: Dishwasher, Dryer, Microwave, Refrigerator, Washer
Baths 1/2: 1
Baths Full: 4
Construction: Wood Frame, Wood Siding
Days on Site: 39
Driveway: Common/Shared, Gravel
Electric: Circuit Breaker(s)
Exterior: Wood Frame, Wood Siding
Flood Zone: Unknown
Flooring: Carpet, Hardwood, Tile
Foundation: Poured Concrete
Hot Tub: Yes
Lot: Mountain View, Ski Area, Wooded, Near Golf Course, Near Skiing
Number of Rooms: 8
Parking: Driveway, Garage
Roads: Paved, Privately Maintained
Sale Inclusions: Furnishings
Sewer: Public
Sq. Ft. Above Grade Finished: 2110
Sq. Ft. Below Grade Finished: 924
Sq. Ft. Total Finished: 3034
Total Stories: 2
Units: 1
Water: Public
Zoning: Residential
Local Schools
School District: Winhall
Listed By / Shown By
Listed By
Agency Name: 42 North LP
Agent Name: David Powers
Agency Phone: 802-214-2714
Shown By
Agent Name: Deb Rees
Agent Phone: Cell: (603) 454-8380
Agency Title: Better Homes and Gardens Real Estate The Masiello Group
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Estimated Payment
$ 6,935.27 per month $5,007.52 Principal & Interest $1,271.50 Property Tax $656.25 Homeowner's Insurance
Listing data compilation and photo(s) 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 2026-11-05 23:33:23 
165 High Meadow Road | MLS# 5111781
This single family home located at 165 High Meadow Road, Winhall, VT 05340 is currently listed for sale with an asking price of $2,250,000. This property was built in 1988 and has 4 bedrooms and 4 full and 1 partial baths with 3034 sq. ft. High Meadow Road is located in the High Meadows subdivision within the Winhall school district. Search High Meadows real estate on debrees.masiellogrouprealestate.com today.