Listed by David Powers • 42 North LP.

For sale

$2,250,000

Est. $14,214/mo —

•

3,034

sq ft

165 High Meadow Rd, Winhall, VT 05340

About this home

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.

Single-familyProperty Type

1988Year Built

1.08 acresLot Size

$742Price/Sq.Ft.

2 car garageParking

Listed by David Powers • 42 North LP

Listing updated: Sep 30, 2026 at 08:05pm

Redfin checked: a minute ago

•Source:PrimeMLS #5111781

Payment calculator

$14,214 per month

Principal and interest$12,586

Property taxes

$1,272

HOA dues

Home insurance

$356

Utilities

Add

5 minutes to get started. No credit impact.

Affordability tools

See this home in person

We'll connect you with a local agent to show you this home, answer your questions, and assist you on your buying journey.

Next available tour time: Tomorrow

Open houses

No upcoming open houses.

Around this home

Schools

K - 12
Preschool & daycare

Mountain School At Winhall

Private K-8 • 1.3mi

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Offer insights

165 High Meadow Rd · $2,250,000

Strong offer

$2.25M and above

75% chance or better to win

Why $2.25M+ is a strong offer

DAYS ON MARKET

The average home goes pending in 72 days.

SALE-TO-LIST

Most homes are selling 3% below list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
8 total rooms
Finished walkout basement
Carpet, hardwood, and tile flooring

Bathrooms
4 full bathrooms
1 half bathroom

Kitchen
Dishwasher
Microwave
Refrigerator

Laundry & utility
Washer
Dryer

Flooring
Carpet
Hardwood
Tile

Heating & cooling
Central air conditioning
Oil heating
Solar heating
Baseboard heat
Heat pump
Hot water heat

Sale and tax history for 165 High Meadow Rd

Sale History
Tax History

Date

Event

Price

PrimeMLS #5111781

Sep 28, 2026

Listed

$2,250,000

$742/sq ft

PrimeMLS #4732265

Sep 4, 2020

Sold

$502,000

$165/sq ft

Sep 2, 2020

Pending

—

Jul 13, 2020

Contingent

—

Jun 26, 2020

Price Changed

$535,000

$176/sq ft

Jun 25, 2019

Price Changed

$545,000

$180/sq ft

Jan 9, 2019

Listed

$589,000

$194/sq ft

+24

High Meadow at Stratton: In Stratton's private community with shuttle to Stratton's slopes on weekends and holidays, this spacious custom home was built for its present owner and very privately sited on a 1.3 acre lot. Kitchen with updated appliances, opens to the generous living/dining area and pretty old brick wood burning fireplace. Living room has views of the top of Stratton's trails and down to a pretty babbling brook. Master bedroom suite is on the mail level with a new master bath. The upper floor has a guest master, third bedroom and bath and spacious loft. The lower level has a family room with stone fireplace and wet bar. A great place for a party! Additionally, there is a 4th bedroom and bath/ Sold furnished. .. Stratton Sports Center Bond Available for Buyer paying transfer fee

Year

Property tax

Land + Additions

Assessment*

2025

$8,753 (−0.8%)

$172,000 + $246,600

$418,600

2024

$8,824 (+18.4%)

$172,000 + $246,600

$418,600

2023

$7,455 (−15.6%)

$172,000 + $246,600

$418,600

2022

$8,828 (−2.6%)

$172,000 + $246,600

$418,600

2021

$9,067

$172,000 + $246,600

$418,600

2020

$9,076 (+5.3%)

$172,000 + $246,600

$418,600

2019

$8,615 (−15.4%)

$172,000 + $246,600

$418,600

2018

$10,183 (+7.5%)

$172,000 + $246,600

$418,600

2017

$9,472 (+2.7%)

$172,000 + $246,600

$418,600

2016

$9,226 (+10.5%)

$172,000 + $246,600

$418,600

2015

$8,346 (−5.4%)

$172,000 + $246,600

$418,600

2014

$8,818

$172,000 + $246,600

$418,600

2013

$172,000 + $246,600

$418,600

Public record

Public record
Zoning

Beds

Baths

3.5

Stories

—

Lot width

—

Lot depth

—

Lot size

1.3 Acres

Year renovated

—

Finished Sq. Ft.

1,688

Unfinished Sq. Ft.

—

Total Sq. Ft.

1,688

Year built

1999

Style

Single Family Residential

County

Bennington County

APN

77124511373

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 15, 2026.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

1/10 Heat Factor

9 days above 85° expected this year, 20 days in 30 years

3/10 Wind Factor

7% chance of strong winds in next 30 years

2/10 Air Factor

0 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Winhall, VT • 05340

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.2 hours in June and 3.5 hours in December, placing it below the U.S. average for solar exposure.

8.2 hrs

3.5 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 165 High Meadow Rd

$2,225,684

$24K under list price of $2.25M

Nearby comparable homes

The Redfin Estimate uses 5 recent nearby sales, priced between $799K to $1.6M.

SOLD SEP 1, 2026
$1,310,000 Last sold price
4 beds2.5 baths2,814 sq ft
19 Maple Hill Rd, Winhall, VT 05340
$276/sq ft
larger lot
10 years older
SOLD JUL 10, 2026
$949,000 Last sold price
5 beds3.5 baths4,000 sq ft
178 High Meadow Rd, Winhall, VT 05340
$505/sq ft
1 year older
SOLD JUL 17, 2026
$799,000 Last sold price
4 beds3.5 baths3,078 sq ft
63 Raspberry Hill Rd, Winhall, VT 05340
$482/sq ft
larger lot
8 years older
SOLD DEC 19, 2025
$1,600,000 Last sold price
3 beds4.5 baths4,312 sq ft
14 Stone House Rd, Winhall, VT 05340
$371/sq ft
12 years newer
SOLD APR 10, 2026
$1,550,000 Last sold price
5 beds4 baths4,000 sq ft
147 High Meadow Rd #147, Winhall, VT 05340
$354/sq ft
larger lot
4 years older

Rental earnings

Est. $3,268 per month, based on comparable rentals

Tour for free, no strings attached

Instant answers, or connect with a local agent

Start an offer

Early Access listings

EARLY ACCESSCOMPASS COMING SOON

$439,000

3 beds3 baths1,530 sq ft

11 Suffolk Dr #2, Concord, NH 03303

Nearby similar homes

$1,475,000

2 beds2 baths1,601 sq ft

691 Black Bear Rd, Jamaica, VT 05343

$279,900

3 beds1 bath1,404 sq ft

0 Old Road Nine, Wardsboro, VT 05355

VIDEO TOUR

$1,997,000

4 beds4.5 baths3,631 sq ft

14 Talon Dr, Stratton, VT 05360

$479,000

3 beds2 baths1,994 sq ft

58 Hi Hopes Rd, Wardsboro, VT 05355

$1,130,000

4 beds3 baths3,357 sq ft

153 High Meadow Rd, Winhall, VT 05340

$549,000

4 beds4 baths3,075 sq ft

24 Mowrey Rd, Jamaica, VT 05343

New listings for sale in 05340

$1,235,000

4 beds4.5 baths3,060 sq ft

33 Old Ridge Rd, Winhall, VT 05340

$745,000

3 beds3.5 baths3,600 sq ft

6 Jamie Ln, Winhall, VT 05340

VIDEO TOUR

$2,950,000

4 beds4 baths3,621 sq ft

60 W Ridge Rd, Winhall, VT 05340

$700,000

3 beds3 baths1,650 sq ft

81 Pond View Rd, Winhall, VT 05340

Details provided by PrimeMLS and may not match the public record. Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

05155 homes for sale
05340 homes for sale
05360 homes for sale
05343 homes for sale

Londonderry homes for sale
Plymouth homes for sale
Stratton homes for sale
Dover homes for sale
Guilford homes for sale

Houses for sale near me	Burlington, VT homes for sale	Brattleboro, VT homes for sale
Land for sale near me	Stowe, VT homes for sale	Waterbury, VT homes for sale
Open Houses near me	Woodstock, VT homes for sale	Stratton Mountain Property Records
Condos for sale near me	Montpelier, VT homes for sale	VT New Listings
Agents near me	South Burlington, VT homes for sale	Stratton Mountain Housing Market

Wilmington homes for sale
Manchester homes for sale
Newfane homes for sale

About this home

Payment calculator

Affordability tools

See this home in person

Around this home

Schools

Lifestyle

Offer insights

Property details

Sale and tax history for 165 High Meadow Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 165 High Meadow Rd

Early Access listings

Nearby similar homes

New listings for sale in 05340

More real estate resources