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

20 East Dugway Rd, Lenox, MA 01240

New Listing

$1,650,000

Second Floor Flex Space-Virtually Staged

Property Type: Residential Bedrooms: 7 Baths: 7 Square Footage: 5,693 Lot Size (sq. ft.): 1,585,584 Status: Active

Current Price: $1,650,000 List Date: 5/22/2026 Last Modified: 5/22/2026

Overview

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.

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 ... (Read more)

Listing Details MLS# 249647

Location, Tax & Legal

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
Assess Amt: 1185400
Elem School: Morris
Middle School: Lenox Memorial
High School: Lenox Memorial
Assessed Year: 2025
Taxes: 10728
Tax Year: 2025
Page: 135

Contract Information

Accessory Dwelling Unit: No
Original List Price: 1650000
Limited Service: No
Agent Interest: None

General Property Description

Realtor.COM Type: Residential - Single Family
Sq Ft Liv Apx: 5693
Sq Ft Source: Assessor
Total Rooms: 18
Total Bedrooms: 7
Total Full Baths: 6
Total Half Baths: Yes
Total Bathrooms: 7
Garage Stalls: 4
Parking Spaces Type: Garaged & Off-Street
Surveillance: No
Year Built Apx: 1921
Year Built Source: Assessor
Yr Blt Description: Approximate
Lot Size Dimensions: Irregular
Acres Apx: 36.4
Lot Size SqFt: 1585584
Frontage Apx: 1304
Betterment: N/A

Status Change Info

Status Change Date: 2026-05-22

Building Info

Exterior Color: Dove White & Brick

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!

More Information

Restrict Covenants

Unk: Yes

Appliances Incl

Dishwasher: Yes
Dryer: Yes
Range: Yes
Refrigerator: Yes
Washer: Yes

Basement

Bulk head: Yes
Interior Access: Yes
Unfinished: Yes

Exterior Amenities

Barn/Stable: Yes
Deck: Yes
Fenced-Partially: Yes
Landscaped: Yes
Patio: Yes
Porch: Yes
Privacy: Yes
Trash Private: Yes
Deciduous Shade Trees: Yes
Mature Landscaping: Yes

Flood Hazard Area

Unk: Yes

Floor

Ceramic Tile: Yes
Laminate: Yes
Linoleum: Yes
Wood: Yes

Fuel

Electric: Yes
Oil: Yes
Propane: Yes

Garage

Attached: Yes
Detached: Yes

Heat/Cool/Vent

Boiler: Yes
Electric: Yes
Heat Pump: Yes
Hot Water: Yes
Multizone: Yes

Hot Water

Electric: Yes

Interior Amenities

Cable Available: Yes
Fireplace (s): Yes
Granite Counter: Yes
Inlaw/Guest Qtrs: Yes
Skylight(s): Yes
Stone Countertop: Yes
Sun Room: Yes
Vaulted Ceilings: Yes
Walk-In Closet(s): Yes

Internet Service

Cable Available: Yes

Lead Paint

Unk: Yes

Lot Description

Adj to Protected Ld: Yes
Corner: Yes
Irregular Shape: Yes
Pasture: Yes
Wooded: Yes

Title V

Unk: Yes

Underground Oil Tank

Unk: Yes

Water

Public: Yes

Right to Farm Comm

No: Yes

Sewer

Private: Yes

Easement

Unk: Yes

Survey

No: Yes

Right of Way

Unk: Yes

Accessibility

1st Fl Bdrm: Yes
1st Flr Bdrm w/Bath: Yes
1st Flr Full Bath: Yes

Electric Type

100 Amp: Yes

Views

Pastoral: Yes

Construction

Wood Frame: Yes

Roof

Membrane: Yes
Asphalt Shingles: Yes

Stove Permit

No: Yes

Style

Colonial: Yes
Cottage: Yes
NE Farmhouse: Yes
Ranch: Yes

Zoning

Residential: Yes

Seller Disc

No: Yes

Exterior Siding

Brick: Yes
Stucco: Yes
Vinyl: Yes

Possession

Close Of Escrow: Yes

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

Documents

Lead Paint Disclosure ›

MA Home Inspection Disclosure ›

Listing Office: WILLIAM PITT SOTHEBY'S - LENOX

Listing Agent: Nick Geranios

Last Updated: May - 22 - 2026

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