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20 E Dugway Rd

Lenox, MA 01240

  • $1,650,000
  • 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.

READ MORELESS
Property Highlights
  • NEIGHBORHOOD : Middle Registry
  • STYLE : Ranch, NE Farmhouse, Colonial, Cottage
  • EXTERIOR FEATURES : Accessible Bedroom, Accessible Full Bath, Deck, Patio, Porch
  • PRICE/SQFT : $290
  • DAYS ON MARKET : 24
  • MLS : 249647
  • Floor Plans

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: 24
  • 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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Floor Plans for 20 E Dugway Rd, Lenox, MA

Location for 20 E Dugway Rd, Lenox, MA

Schools for 20 E Dugway Rd, Lenox, MA

Our community offers residents access to a number of fine private and public schools for all grade levels. Please read below for information on each of the schools in our area.

Private Schools
SCHOOL LOCATION GRADE
Berkshire Christian Schools PO BOX 1980 Lenox, MA 01240 PK - 12
The Montessori School of the Berkshires 21 Patterson Road Lee, MA 01238 PK - 8
Housatonic Academy 788 South Street Pittsfield, MA 01201 2 - 12
Berkshire Country Day School 55 INTERLAKEN ROAD, ROUTE 183 Stockbridge, MA 01262 PK - 8
The Center School 788 South Street Pittsfield, MA 01201 5 - 12
Hillcrest Educational Center - Brookside 788 South Street Pittsfield, MA 01201 3 - 12
Miss Hall's School 492 Holmes Road Pittsfield, MA 01201 9 - 12
Frontline Church School 160 High Street Lee, MA 01238 11
St Mary's School 115 Orchard Street Lee, MA 01238 PK - 8
GreatSchools

*UG = ungraded.
Detailed school information provided by GreatSchools.org © . All rights reserved.

Public and private school information is provided by sources including GreatSchools.org and various MLS services including the One Key, SMARTMLS, NCMLS, DARMLS and Greenwich MLS, and is subject to the terms of use on those sites. William Pitt and Julia B. Fee Sotheby’s International Realty believes the information provided by these sources to be accurate but will not be held responsible if any data as well as information such as school districts for listings is inaccurate.

Community

Lenox>

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

Listing Courtesy of Nick Geranios of WILLIAM PITT SOTHEBY'S - LENOX (413.637.4402).

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