20 East Dugway Rd, Lenox, MA 01240 (MLS# 249647)

$1,650,000
20 East Dugway Rd
Lenox, MA 01240
MLS# 249647
7 beds  |  7 baths  |  5693 sqft
Main House Exterior Side
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Main House Exterior Side Main House Exterior Main House Exterior Main House Exterior Main House Exterior Front Exterior Screened in Porch Exterior Garage Kitchen Kitchen Eat-In Kitchen First Floor Main Bathroom Dining Room - Virtually Staged Dining Room Sun Room - Virtually Staged Sun Room Living Room Living Room - Virtually Staged Living Room Flex Space off the Living Room Flex Space off the Living Room Living Room First Floor Office - Virtually Staged First Floor Office Primary Bedroom - Virtually Staged First Floor Primary Bedroom Primary Bedroom Ensuite Bathroom First Floor Laundry First Floor Bedroom 2 First Floor Bedroom 2 Family Room - Entry Area Second Floor Entry Second Floor Kitchen - Virtually Staged Second Floor Kitchen Second Floor Kitchen Second Floor Kitchen Second Floor Bedroom 3 Second Floor Bedroom 3 Second Floor Bedroom 3 Second Floor Bath 2 Second Floor Bedroom 4 Second Floor Flex Space-Virtually Staged Second Floor Flex Space Second Floor Flex Space Second Floor Bathroom 1 Main House Exterior Main House Exterior Exterior Guest House Exterior Guest House Exterior Guest House Exterior Front Exterior Front Guest House Guest House Kitchen Guest House Kitchen Guest House Kitchen Guest House - Living Room into Kitchen Guest House Living Room Guest House Living Room Guest - 11 Guest - 10 Main Bathroom Guest House Main Bathroom Guest House Guest House Bedroom 2 Guest House Bedroom 2 Guest House Bedroom 2 Exterior Side Guest House Guest House Garage Driveway to Main House Exterior Side Yard Exterior Guest House - Yard Exterior Exterior Aerial View Aerial View Aerial View Aerial View Aerial View Fire Pit Barn Main House All Floors Main House 1st Floor Main House 2nd Floor Guest House

Property 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.

Details
Maps
Documents
Contract Information
Accessory Dwelling Unit: No
Original List Price: 1650000
Limited Service: No
Agent Interest: None
Current Price: $1,650,000
Status: Active
List Date: 2026-05-21
List Price: $1,650,000
Location, Tax & Legal
Assess Amt: 1185400
Elem School: Morris
Middle School: Lenox Memorial
High School: Lenox Memorial
Assessed Year: 2025
Taxes: 10728
Tax Year: 2025
Page: 135
Registry: Middle Registry
Street #: 20
Street Direction: East
Street Name: Dugway
Street Ext: Rd
State/Province: MA
Postal Code: 01240
Map Ref: M:17 B:054 P:0000 U:00
General Property Description
Surveillance: No
Realtor.COM Type: Residential - Single Family
Total Bathrooms: 7
Parking Spaces Type: Garaged & Off-Street
Sq Ft Source: Assessor
Total Rooms: 18
Total Bedrooms: 7
Garage Stalls: 4
Year Built Source: Assessor
Yr Blt Description: Approximate
Lot Size Dimensions: Irregular
Lot Size SqFt: 1585584
Frontage Apx: 1304
Betterment: N/A
Sq Ft Liv Apx: 5693
Total Full Baths: 6
Total Half Baths: 1
Year Built Apx: 1921
Acres Apx: 36.4
Remarks & Misc
Additional Disclosures: *Please respect the privacy of the property--NO DRIVE-BYS. Entry is by appointment only and requires prior approval from the listing agent. *This offering encompasses two parcels sold as one: an 18 acre parcel featuring the residences and a second 18.4 acre parcel of undevelopable land, presenting exceptional possibilities for privacy and expansion. **Total square footage and room counts etc. are for both the main house and the guest house/studio.
Directions: 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
Marketing/Headline: Just one mile from the heart of Lenox, nearly 36 acres await your next chapter! A rare offering!
Restrict Covenants
Unk: 1
Appliances Incl
Dishwasher: 1
Dryer: 1
Range: 1
Refrigerator: 1
Washer: 1
Basement
Bulk head: 1
Interior Access: 1
Unfinished: 1
Exterior Amenities
Barn/Stable: 1
Deck: 1
Fenced-Partially: 1
Landscaped: 1
Patio: 1
Porch: 1
Privacy: 1
Trash Private: 1
Deciduous Shade Trees: 1
Mature Landscaping: 1
Flood Hazard Area
Unk: 1
Floor
Ceramic Tile: 1
Laminate: 1
Linoleum: 1
Wood: 1
Fuel
Electric: 1
Oil: 1
Propane: 1
Garage
Attached: 1
Detached: 1
Heat/Cool/Vent
Boiler: 1
Electric: 1
Heat Pump: 1
Hot Water: 1
Multizone: 1
Hot Water
Electric: 1
Interior Amenities
Cable Available: 1
Fireplace (s): 1
Granite Counter: 1
Inlaw/Guest Qtrs: 1
Skylight(s): 1
Stone Countertop: 1
Sun Room: 1
Vaulted Ceilings: 1
Walk-In Closet(s): 1
Internet Service
Cable Available: 1
Lead Paint
Unk: 1
Lot Description
Adj to Protected Ld: 1
Corner: 1
Irregular Shape: 1
Pasture: 1
Wooded: 1
Title V
Unk: 1
Underground Oil Tank
Unk: 1
Water
Public: 1
Right to Farm Comm
No: 1
Sewer
Private: 1
Building Info
Exterior Color: Dove White & Brick
Easement
Unk: 1
Survey
No: 1
Right of Way
Unk: 1
Accessibility
1st Fl Bdrm: 1
1st Flr Bdrm w/Bath: 1
1st Flr Full Bath: 1
Electric Type
100 Amp: 1
Views
Pastoral: 1
Construction
Wood Frame: 1
Roof
Membrane: 1
Asphalt Shingles: 1
Stove Permit
No: 1
Style
Colonial: 1
Cottage: 1
NE Farmhouse: 1
Ranch: 1
Zoning
Residential: 1
Seller Disc
No: 1
Exterior Siding
Brick: 1
Stucco: 1
Vinyl: 1
Possession
Close Of Escrow: 1
Status Change Info
Status Change Date: 2026-05-22
Property Features
Restrict Covenants: Unk
Title V: Unk
Underground Oil Tank: Unk
Water: Public
Sewer: Private
Easement: Unk
Survey: No
Right of Way: Unk
Right to Farm Comm: No
Flood Hazard Area: Unk
Views: Pastoral
Lot Description: Adj to Protected Ld; Corner; Irregular Shape; Pasture; Wooded
Stove Permit: No
Electric Type: 100 Amp
Style: Colonial; Cottage; NE Farmhouse; Ranch
Interior Amenities: Cable Available; Fireplace (s); Granite Counter; Inlaw/Guest Qtrs; Skylight(s); Stone Countertop; Sun Room; Vaulted Ceilings; Walk-In Closet(s)
Internet Service: Cable Available
Accessibility: 1st Fl Bdrm; 1st Flr Bdrm w/Bath; 1st Flr Full Bath
Exterior Amenities: Barn/Stable; Deck; Fenced-Partially; Landscaped; Patio; Porch; Privacy; Trash Private; Deciduous Shade Trees; Mature Landscaping
Appliances Incl: Dishwasher; Dryer; Range; Refrigerator; Washer
Construction: Wood Frame
Exterior Siding: Brick; Stucco; Vinyl
Roof: Asphalt Shingles; Membrane
Basement: Bulk head; Interior Access; Unfinished
Floor: Ceramic Tile; Laminate; Linoleum; Wood
Garage: Attached; Detached
Fuel: Electric; Oil; Propane
Hot Water: Electric
Lead Paint: Unk
Zoning: Residential
Seller Disc: No
Possession: Close Of Escrow
Supplements
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.
Listing Office: WILLIAM PITT SOTHEBY'S - LENOX
Listing Agent: Nick Geranios

Last Updated: May - 26 - 2026

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