20 East Dugway Rd, Lenox, MA 01240
Local realty services provided by:CENTURY 21 North East
20 East Dugway Rd,Lenox, MA 01240
$1,650,000
- 7 Beds
- 7 Baths
- 5,693 sq. ft.
- Single family
- Active
Listed by: nick geranios, carrie lobovits wright
Office: william pitt sotheby's - lenox
MLS#:249647
Source:MA_BCMLS
Price summary
- Price:$1,650,000
- Price per sq. ft.:$289.83
About this home
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....
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Home facts
- Year built:1921
- Listing ID #:249647
- Added:151 day(s) ago
- Updated:September 16, 2026 at 03:46 PM
Rooms and interior
- Bedrooms:7
- Total bathrooms:7
- Full bathrooms:6
- Half bathrooms:1
- Rooms Total:18
- Flooring:Ceramic Tile, Laminate, Linoleum, Wood
- Kitchen Description:Dishwasher, Granite Counter, Range, Refrigerator
- Basement Description:Bulk head, Interior Access, Unfinished
- Living area:5,693 sq. ft.
Heating and cooling
- Cooling:Electric, Heat Pump, Multizone
- Heating:Boiler, Electric, Heat Pump, Hot Water, Multizone
Structure and exterior
- Roof:Membrane
- Year built:1921
- Building area:5,693 sq. ft.
- Lot area:36.4 Acres
- Lot Features:Adjacent to Protected Land, Corner, Irregular Shape, Pasture, Wooded
- Architectural Style:Colonial, Cottage, Farmhouse, Ranch
- Construction Materials:Brick, Stucco, Vinyl
- Exterior Features:Barn/Stable, Deciduous Shade Trees, Deck, Fenced-Partially, Landscaped, Mature Landscaping, Patio, Porch, Privacy
Schools
- High school:Lenox Memorial
- Middle school:Lenox Memorial
- Elementary school:Morris
Utilities
- Water:Public
- Sewer:Private
Finances and disclosures
- Price:$1,650,000
- Price per sq. ft.:$289.83
- Tax amount:$10,728 (2025)
Features and amenities
- Appliances:Dishwasher, Range, Refrigerator, Washer
- Laundry features:Dryer, Washer
- Amenities:Cable Internet, Electric Water Heater, Inlaw/Guest Qtrs, Skylight(s), Sun Room, Vaulted Ceilings, Walk-In Closet(s)
Parking
- Parking description:Attached, Detached, Garaged & Off-Street
- Garage spaces:4
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