For Sale
Single family home for sale at 165 High Meadow Rd, Winhall, VT 05340 | MLS# 5111781 | Listing updated on 2026-09-30
Photo 1 of Single family home for sale at 165 High Meadow Rd, Winhall, VT 05340 | MLS# 5111781 | Listing updated on 2026-09-30
Photo 2 of Single family home for sale at 165 High Meadow Rd, Winhall, VT 05340 | MLS# 5111781 | Listing updated on 2026-09-30
Photo 3 of Single family home for sale at 165 High Meadow Rd, Winhall, VT 05340 | MLS# 5111781 | Listing updated on 2026-09-30
Photo 4 of Single family home for sale at 165 High Meadow Rd, Winhall, VT 05340 | MLS# 5111781 | Listing updated on 2026-09-30
36+
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Street View

Listed by: David Powers | 42 North LP (802) 214-2714

$2,250,000

Monthly Est:$11,199

  • Beds Icon4 Beds
  • Beds Icon
    5 Baths
  • Beds Icon2,110sqft

165 High Meadow Rd, Winhall, VT 05340

$11,199/moEst:

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  • Single Family Residence

  • Built in 1988

  • $-- HOA

  • 1.08 acres lot

  • $1,066/sq.ft

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. 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.

  • Houzeo last checked: 12 hours ago
  • Listing updated: September 30, 2026 at 5:05 pm
  • Source: NEREN/Prime MLS-NH | MLS#: 5111781 NEREN/Prime MLS-NH

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Vt Bennington County

  • City

    Winhall

  • Neighborhood

    --

  • Year Built

    1988

  • HOA Fees

    -

  • Finished Area

    2,110 sqft

  • Lot Size

    1.08 acres lot

  • Basement Area

    - sqft

  • MLS Name

    NEREN/Prime MLS

  • MLS Number

    5111781

  • MLS Status

    (10) Active - Active

  • Days on Market

    9

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 5

Interior

  • Heating

    Oil, Solar, Baseboard, Heat Pump, Hot Water

  • Appliances

    Dishwasher, Dryer, Microwave, Refrigerator, Washer

  • Flooring

    Carpet, Hardwood, Tile

  • Interior Features

    Wood Fireplace, 1 Fireplace, Furnished, Hot Tub, Kitchen/dining, Primary Br W/ Ba, Sauna, Wet Bar

  • Exterior Features

    Deck, Hot Tub, Patio, In Ground Pool, Sauna

  • Sewer

    Public

  • Cooling

    Central Air

Construction

  • Year Built

    Year Built: 1988

  • Home type

    Single Family Residence

  • Property Condition

    Existing

  • Construction Materials

    Wood Frame, Wood Siding

  • Roof

    Asphalt Shingle

  • Foundation Details

    Poured Concrete

  • Architectural Style

    Contemporary, Walkout Lower Level

Utilities & Energy

  • Water Source

    Public

  • Electric

    Circuit Breakers

  • Utilities

    Other

  • Parking Features

    Driveway, Garage

  • Basement

    Finished, Walk Out Access

Other Features

  • Lot Features

    Mountain View, Ski Area, Wooded, Near Golf Course, Near Skiing

  • Subdivision Name

    High Meadows

Price History

DateEventPrice

09/30/2026

Source: mls_logoNEREN/Prime MLS-NH #5111781

Listed for Sale

$2,250,000 +348.21%

$1,066/sqft

09/05/2020

Source: mls_logoNEREN/Prime MLS-NH #4732265

Sold

$502,000

$238/sqft

Getting Around 165 High Meadow Rd

Bike Score®

Bike Score

Somewhat Bikeable

5/100

Walk Score®

Walk Score

Car-Dependent

0/100

Data provided by Redfin

Nearby Homes

Based on information from PrimeMLS Inc. through Oct 07, 2026, 06:00AM. This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information. The listing broker's offer of compensation is made only to other real estate licensees who are participant members of PrimeMLS. 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 Oct 07, 2026, 06:00AM. © 2026 PrimeMLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group