20 E Dugway Rd Lenox, MA 01240
7 Beds
7 Baths
5,693 SqFt
UPDATED:
Key Details
Property Type Single Family Home
Listing Status Active
Purchase Type For Sale
Square Footage 5,693 sqft
Price per Sqft $289
MLS Listing ID 249647
Style Ranch,NE Farmhouse,Colonial,Cottage
Bedrooms 7
Full Baths 6
Half Baths 1
Year Built 1921
Annual Tax Amount $10,728
Tax Year 2025
Lot Size 36.400 Acres
Acres 36.4
Lot Dimensions Irregular
Source Berkshire County Board of REALTORS®
Property Description
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.
Location
State MA
Area Middle Registry
Direction From East Street in Lenox, turn onto East Dugway Road and continue uphill toward the end of the road (towards Route 7). The private driveway for 20 East Dugway will be on the left. Shown by appointmen
Rooms
Basement Unfinished, Interior Access, Bulk head
Interior
Interior Features Cable Available, Fireplace (s), Granite Counter, Inlaw/Guest Qtrs, Skylight(s), Stone Countertop, Sun Room, Vaulted Ceilings, Walk-In Closet(s)
Heating Propane, Oil, Electric, Boiler, Hot Water
Cooling Electric
Flooring Ceramic Tile, Laminate, Linoleum, Wood
Appliance Dishwasher, Dryer, Range, Refrigerator, Washer
Exterior
Exterior Feature Trash Private, Privacy, Porch, Deciduous Shade Trees, Deck, Barn/Stable, Mature Landscaping, Fenced-Partially, Landscaped, Patio
Parking Features true
Garage Spaces 4.0
Garage Description Garaged & Off-Street
View Pastoral
Roof Type Asphalt Shingles,Membrane
Accessibility Accessible Bedroom, Accessible Full Bath, 1st Flr Bdrm w/Bath
Porch true
Total Parking Spaces 4
Garage true
Building
Lot Description Wooded, Pasture, Irregular Shape, Corner, Adj to Protected Ld
Sewer Private Sewer
Water Public
Architectural Style Ranch, NE Farmhouse, Colonial, Cottage
Schools
Elementary Schools Morris
Middle Schools Lenox Memorial
High Schools Lenox Memorial