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20 E Dugway Rd

Lenox, MA 01240

$1,650,000 PRICE
7 Beds
6/1 Baths
5,693 Sqft
36.4 Acres
1921 Built

Just One Mile From The Heart Of Lenox, Nearly 36 Acres Await Your Next Chapter!

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.

Listed by

Nick Geranios
Licensed Real Estate Salesperson
M
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Carrie Lobovits Wright
Licensed Real Estate Salesperson
M
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Additional Information

LOT DETAILS

HAS VIEW: Yes
LOT DESCRIPTION: Wooded, Corner Lot, Irregular Lot, Pasture, Landscaped, Few Trees
WATER: Public

EXTERIOR FEATURES

ROOF: Rubber, Membrane
EXTERIOR FEATURES: Accessible Bedroom, Accessible Full Bath, Deck, Patio, Porch

INTERIOR FEATURES

APPLIANCES INCLUDED: Dishwasher, Dryer, Range, Refrigerator, Washer
BEDS: 7
COOLING: Electric
FLOORING: Vinyl, Ceramic Tile, Laminate, Linoleum, Wood
FULL BATHS: 6
HEAT: Propane, Oil, Electric, Hot Water
INTERIOR FEATURES: In-Law Floorplan, Vaulted Ceiling(s), Walk-In Closet(s)
ROOMS: 18

ADDITIONAL INFORMATION

BASEMENT DESCRIPTION: Unfinished
DAYS ON MARKET: 8
ELECTRICAL FEATURES: 100 Amp Service
ELEMENTARY SCHOOL: Morris
HIGH SCHOOL: Lenox Memorial
LIVING AREA SQFT: 5693
MIDDLE SCHOOL: Lenox Memorial
ON MARKET DATE: 2026-05-22
PARKING: Off Street, Attached
SEWER: Private Sewer
STYLE: Ranch, NE Farmhouse, Colonial, Cottage
TAX YEAR: 2025
UTILITIES: Cable Available
YEAR BUILT: 1921
ZONING: Residential

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Nick Geranios
Licensed Real Estate Salesperson
M

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Community

Lenox

Berkshire County, Massachusetts

Lenox, located in the heart of the Berkshires, is a primary summer resort destination and home to many of the region’s most visited attractions, including Tanglewood Music Center and the Edith Wharton...

Market Stats for Lenox, Massachusetts

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Request More Info for 20 E Dugway Rd, Lenox, MA

Nick Geranios
Licensed Real Estate Salesperson
M

View My Profile
Carrie Lobovits Wright
Licensed Real Estate Salesperson
M

View My Profile

Schedule a Showing Best Day/Time

Yes, I would like more information from Sotheby's International Realty. Please use and/or share my information with a Sotheby's International Realty agent to contact me about my real estate needs.