20 E Dugway Rd, Lenox, MA

Name: 20 E Dugway Rd, For Sale in Lenox - Zoocasa
Brand: WILLIAM PITT SOTHEBY'S - LENOX
SKU: 249647
Price: 1650000 USD

House

For Sale

Listed price in listed location currency (USD).

$1,650,000

774

MLS® 249647

Overview

Key Facts

Type Single Family Residence

Levels Residential

Size 5693 sqft

Garage Yes

Taxes $10,728

Days Active 0

Lot Size

Approx. Age 1921

Avg. Price Per Sqft $289

MLS® Number 249647

Property Address: 20 E Dugway Rd, Lenox, MA, 01240-2111

Average square foot calculated using Size range provided by listing agent.

Description

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. A heated sunroom and screened porch extend the living experience across seasons. The primary suite includes an en-suite bath, and this level is further enhanced by a second kitchen and laundry hookups, creating true independence within the home. The second floor functions as its own private level, featuring three bedrooms and two full baths. The guest house feels like a second home entirely. With two bedrooms, two full baths, a dramatic stone fireplace, and a kitchen finished with Caesarstone quartz, it offers independence without compromise. Mini-split systems provide year-round comfort, while a private laundry and generous scale make it equally suited for extended stays or full-time living. Both residences feature claw-foot tubs and roofs replaced within the past three years. A two-car garage at both houses, potting shed, fire pit ring, and expansive grounds complete the offering. This is a property defined by flexibility and scale--where multiple generations can live together while maintaining independence, and where land, light, and structure align to create lasting possibility.

MLS® Number249647

Laundry Level

Central VacNo

FireplaceNo

Acreage

Exterior

GarageYes

Approx. Age1921

Basement

DrivewayGaraged & Off-Street

Garage Spaces

Heat

A/C

Heating Fuel

Extras

Price History

-End Date

Not Sold YetSold Price

For Sale

May 22, 2026List Date

$1,650,000List Price

Map

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