Just 3 miles from Tanglewood and moments from the heart of Lenox, this 36+ acre estate offers rare scale, privacy, and flexibility in one of the Berkshires' most sought-after settings.A long, tree-lined driveway creates a strong sense of arrival, unfolding into two separate residences surrounded by woods, open land, and long-range possibility. The acreage offers both seclusion and the ability to selectively open views toward October Mountain State Forest.The main residence is thoughtfully configured for multi-generational living. The first floor centers around a large living and dining room anchored by an oversized stone fireplace, an eat-in kitchen with oak cabinetry and granite counters, and multiple access points to the outdoors.

Property Details

Interior Features

Utilities and Appliances

Community

Based on information submitted to BCMLS as of May 23, 2026 . All data is obtained from various sources and has not been, and will not be, verified by broker or BCMLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

Name

Your Email Address

Phone

Message Send me the deed for 20 East Dugway Road Lenox MA 01240 (ID#:249647)

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Name

Your Email Address

Phone

Message Send me the survey or tax map for 20 East Dugway Road Lenox MA 01240 (ID#:249647)

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Name

Your Email Address

Phone

Message I would like more information for 20 East Dugway Road Lenox MA 01240 (ID#:249647)

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Listing Tools

Property Details of 20 East Dugway Road

Property Details

Basic Information

Building

Location

Water

Interior Features

Bedrooms

Bathrooms

Basement

Utilities and Appliances

Utilities and Appliances

Community

Schools

Map Location

Driving Directions

Alton & Westall Real Estate Agency

Listing Tools

Hi there! How can we help you?

Property Details of 20 East Dugway Road

Property Details

Basic Information

Building

Location

Water

Interior Features

Bedrooms

Bathrooms

Basement

Utilities and Appliances

Utilities and Appliances

Community

Schools

Map Location

Driving Directions

Hi there! How can we help you?

Hi there! How can we help you?

Hi there! How can we help you?

Alton & Westall Real Estate Agency