8 Winhall Woods Rd

Off Market

8 Winhall Woods Rd

Bennington County VT 05340

1820 sq. ft.

52272 sq. ft.

Single-Family

Last sold for $340,000

Carrie Mathews, last sold this property on 11 March 2026 after 109 days on market.

Overview

Discover this quintessential Vermont ski chalet, perfectly set on a quiet dead-end road with views of Bromley Mountain from the property. Warm and inviting, the home is filled with natural wood throughout, creating the classic mountain-home atmosphere buyers love. Offering both charm and convenience, the location is ideal—just 2.5 miles to Bromley Mountain, 10 miles to Stratton, and only 8 miles to Manchester’s restaurants, shops, indoor ice rink, and year-round amenities. Whether you’re looking for a cozy retreat after a day on the slopes or a peaceful getaway surrounded by nature, this chalet delivers the perfect blend of privacy, comfort, and Vermont mountain living. Seasonal lease in place through April 19, 2026—buyer may close afterward or assume the lease with rental income prorated at transfer.

Features

3 bedrooms

2 bathrooms

1820 sq. ft. floor area

52272 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Bennington County over the last 12 months, the estimated median property value of 8 Winhall Woods Rd is $600k.

Median value

$600k

Estimated value range

$339k - $1.6m

Median days on market

Estimated value trend

-1%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Bennington County. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 8 Winhall Woods Rd

2026

Sold

$340,000

11 Mar 2026 by Carrie Mathews, of William Raveis Winhall

2018

Sold

$115,000

17 Jan 2018 by RON MARCELLUS

Happy sellers in Bennington County

We have insufficient information to provide an overview of customer satisfaction for Bennington County. Viewing the agent profiles, reviews and sales for Bennington County can provide insights for this location.

Local market activity for 3 bedroom single-family properties in Bennington County

In the last 12 months, 12 three-bedroom single-family properties similar to 8 Winhall Woods Rd, have been sold.

This represents a 19% increase in three-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Bennington County for a market analysis.

Tg Glazer

4.8

(6 reviews)

Get a market analysis

Christine Chovan

at The Haven Group

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Tatsiana Clark

at Four Seasons Sotheby's International Realty

Get a market analysis

Laura Beckwith

at Josiah Allen Real Estate, Inc.

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Bennington County

Tg Glazer

Tg Glazer is an award winning recommended agent for Bennington County. They have 2 local sales and collected 2 local reviews across the last 12 months.