20 E Dugway Rd

Lenox, MA 01240

$1,650,000
Price
7
Beds
5,693 Sq. Ft.
$290 / Sq. Ft.
5,693
Sq. Ft.
$290
per Sq. Ft.
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Main House Exterior Side
a front view of a house with a yard and garage
a front view of a house with yard and green space
a front view of a house with garden
Main House Exterior Front
a view of a backyard with of a house
Screened in Porch
Exterior Garage
a kitchen with stainless steel appliances granite countertop a stove a refrigerator and a sink
a kitchen with stainless steel appliances a stove sink and cabinets
Eat-In Kitchen
a bathroom with a sink and a mirror
a view of a dining room and livingroom with furniture wooden floor and a large window
a view of an empty room with wooden floor and a window
Sun Room - Virtually Staged
Sun Room
a view of a room with wooden floor fireplace and windows
a living room with furniture a fireplace and a flat screen tv
a view of an empty room with window and fireplace
a view of an empty room with wooden floor and a window
Flex Space off the Living Room
Living Room
a view of a workspace with furniture and a potted plant
First Floor Office
Primary Bedroom - Virtually Staged
First Floor Primary Bedroom
a bedroom with a bed and a sink
a view of entryway with wooden floor
a view of an empty room with wooden floor and a window
a view of an empty room with wooden floor and a window
an empty room with wooden floor and windows
a view of room with window and hardwood floor
a dining room with furniture a chandelier and wooden floor
a kitchen with stainless steel appliances granite countertop a stove a refrigerator and a sink with wooden floor
a view of an empty room with wooden floor and a window
an empty room with wooden floor and windows
Second Floor Bedroom 3
an empty room with wooden floor and windows
an empty room with wooden floor and windows
a bathroom with a toilet a sink and mirror
Second Floor Bedroom 4
a living room with furniture and a large window
an empty room with wooden floor and windows
a view of an empty room with glass door and balcony
a bathroom with a sink a toilet and a mirror
Main House Exterior
Main House Exterior
a view of a field of grass and trees
Guest House Exterior
a view of a house with backyard and garden
a view of a house with backyard and garden
a backyard of a house with table and chairs
a view of a dining room with furniture and a fireplace
a dining room with furniture and window
a view of a dining room with furniture window and wooden floor
Guest House - Living Room into Kitchen
a living room with furniture and a window
a living room with furniture and a flat screen tv
a bedroom with bed and wooden floor
a bathroom with a toilet a sink and a mirror
Main Bathroom Guest House
a bathroom with a sink and a mirror
a bedroom with a bed and a chandelier
Guest House Bedroom 2
a bedroom with a bed and a window
a view of a house with backyard and garden
Guest House Garage
Driveway to Main House
a view of a big yard with large trees
Exterior
Guest House - Yard
Exterior
Exterior
a close up of a plant in a garden
an aerial view of a house with a yard basket ball court and outdoor seating
Aerial View
Aerial View
Aerial View
Fire Pit
Barn
Main House All Floors
a picture of a room with a white wall and a white wall
Main House 2nd Floor
Guest House

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...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.
  1. Listed by Nick Geranios • WILLIAM PITT SOTHEBY'S - LENOX
  2. Listed by Carrie Wright • WILLIAM PITT SOTHEBY'S - LENOX

Property Details for 20 East Dugway Road

Architectural Style
Ranch, NE Farmhouse, Colonial, Cottage
View
Pastoral
Parking Spaces Type
Garaged & Off-Street
Zoning Description
Residential
LISTING UPDATED: 05/26/2026 03:41 PM

Property Details for 20 East Dugway Road

StatusActive
MLS #249647
Days on Market14
Taxes$10,728 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1921
Lot Size36.40 AC / 1,585,584 SF
CountyBerkshire County
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Location

Listing Courtesy of WILLIAM PITT SOTHEBY'S - LENOX, Nick Geranios; WILLIAM PITT SOTHEBY'S - LENOX, Carrie Wright
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Building Information for 20 East Dugway Road

Stories-Year Built1921Building Size-Lot Size36.40 AC / 1,585,584 SF

Payment Calculator

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$9,116 per month

30 year fixed, 6.36% Interest

Principal and Interest

$8,222

Property Taxes

$894

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 20 East Dugway Road

Summary
Location and General Information
  • 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
  • MLS Area Major: Middle Registry
  • Latitude: 42.37
  • Longitude: -73.28
  • MLS Area Minor: Middle Registry
  • Views Pastoral: Yes
Taxes and HOA
  • Tax Book Number: 8001
  • Parcel Number: M:17 B:054 P:0000 U:00
  • Association Fee: $.00
  • Tax Amount: $10,728.00
  • Tax Assessed Value: 1185400
  • Assess Amount: $1,185,400.00
  • Assessed Year: 2025.0
  • Tax Year: 2025
  • Book: 8001
  • Page: 135
School Information
  • Middle Or Junior School: Lenox Memorial
  • High School: Lenox Memorial
  • Elementary School: Morris
  • Elementry School: Morris
  • Middle School: Lenox Memorial
Parking
  • Garage Spaces: 4.00
  • Other Parking: Garaged & Off-Street
  • Attached Garage: Yes
  • Garage Stalls: 4.00
  • Garage Attached: Yes
  • Garage Detached: Yes
Virtual Tour
  • Virtual Tours Count: 0
Property
Lot Information
  • Lot Size Area: 36.4
  • Lot Size Units: Acres
  • Lot Features: Wooded, Pasture, Irregular Shape, Corner, Adj to Protected Ld
  • Lot Size Acres: 36.4
  • Lot Size Dimensions: Irregular
  • Lot Size Square Feet: 1585584.0
  • Square Feet Source: Assessor
  • Living Area: 5693.0
  • Building Area Total: 5693.0
  • Property Type: Residential
  • Lot Description adjacent to Protected Land: Yes
  • Lot Description Corner: Yes
  • Lot Description Irregular Shape: Yes
  • Lot Description Pasture: Yes
  • Lot Description Wooded: Yes
  • Restrict Covenants Unknown: Yes
Property and Assessments
  • Floor Plans Count: 7
  • Total Bathrooms Source: MLS
  • Photos Count: 84
  • Videos Count: 1
  • Documents Count: 2
  • Property Type: Residential
  • Year Built Description: Approximate
  • Betterment: N/A
  • Easement Unknown: Yes
  • Survey No: Yes
  • Year Built: 1921
  • Year Built Source: Assessor
  • Year Built Details: Approximate
  • Flood Hazard Area Unknown: Yes
  • Title V Unknown: Yes
Utilities
  • Sewer: Private
  • Water: Yes
  • Water Access Public: Yes
  • Sewer Private: Yes
  • Stove Permit No: Yes
  • Internet Service Cable Available: Yes
Interior and Exterior Features
Exterior Features
  • Exterior Features: Trash Private, Privacy, Porch, Deciduous Shade Trees, Deck, Barn/Stable, Mature Landscaping, Fenced-Partially, Landscaped, Patio
  • Exterior Amenities Barn Stable: Yes
  • Exterior Amenities Deck: Yes
  • Exterior Amenities FencedPartially: Yes
  • Exterior Amenities Landscaped: Yes
  • Exterior Amenities Patio: Yes
  • Exterior Amenities Porch: Yes
  • Exterior Amenities Privacy: Yes
  • Exterior Amenities Trash Private: Yes
  • Exterior Amenities Deciduous Shade Trees: Yes
  • Exterior Amenities Mature Landscaping: Yes
  • Roof Membrane: Yes
  • Exterior Siding Brick: Yes
  • Exterior Siding Stucco: Yes
  • Exterior Siding Vinyl: Yes
  • Electric Type 100 Amp: Yes
  • Frontage Approximate: 1,304.00
  • Right of Way Unknown: Yes
  • Post Beam Wood Frame: Yes
  • Style Colonial: Yes
  • Style Cottage: Yes
  • Style NE Farmhouse: Yes
  • Style Ranch: Yes
Interior Features
  • Baths Half: 1
  • Baths Total: 7.00
  • Baths Full: 6
  • Total Bathrooms: 7
  • Bathrooms Total Decimal: 6.50
  • Bathrooms Total Notational: 6.10
  • Total Rooms: 18.00
  • Accessibility 1st Floor Full Bath: Yes
  • Heating: Propane, Oil, Electric, Boiler, Hot Water
  • Kitchen Appliances: Dishwasher, Dryer, Range, Refrigerator, Washer
  • Cooling: True
  • Heating: Yes
  • Underground Oil Tank Unk: Yes
  • Building Information Exterior Color: Dove White & Brick
  • Interior Features: Cable Available, Fireplace (s), Granite Counter, Inlaw/Guest Qtrs, Skylight(s), Stone Countertop, Sun Room, Vaulted Ceilings, Walk-In Closet(s)
  • Interior Amenities Fireplaces: Yes
  • Interior Amenities Granite Counter: Yes
  • Interior Amenities In law Guest Quarters: Yes
  • Interior Amenities Skylight: Yes
  • Interior Amenities Sun Room: Yes
  • Interior Amenities Vaulted Ceilings: Yes
  • Interior Amenities WalkIn Closet: Yes
  • Basement Bulk head: Yes
  • Basement Interior Access: Yes
  • Basement Unfinished: Yes
  • Fuel Electric: Yes
  • Fuel Oil: Yes
  • Fuel Propane: Yes
  • Hot Water Electric: Yes
  • Appliances Included Dishwasher: Yes
  • Appliances Included Dryer: Yes
  • Appliances Included Refrigerator: Yes
  • Appliances Included Washer: Yes
  • Floor Laminate: Yes
  • Floor Linoleum: Yes
  • Floor Wood: Yes
  • Heat/Cool/Vent Electric: Yes
  • Heat/Cool/Vent Heat Pump: Yes
  • Heat/Cool/Vent Hot Water: Yes
  • Heat/Cool/Vent Multizone: Yes
  • Heat/Cool/Vent Boiler: Yes
  • Lead Paint Unk: Yes
Room Information
Room Details
  • Rooms Total: 18
Rental
Rental Information
  • Certified Occupancy No: Yes

Property History for 20 East Dugway Road

DateEvent & SourcePriceAppreciation
May 21, 2026

Listed (Active)

Berkshire County Board of REALTORS #249647

$1,650,000—
Nov 29, 2025

Canceled

Berkshire County Board of REALTORS #246627

—
Jun 4, 2025

Listed (Active)

Berkshire County Board of REALTORS #246627

$2,200,000—
DateEvent & SourcePrice
05/21/2026

Listed (Active)

Berkshire County Board of REALTORS #249647

$1,650,000
11/29/2025

Canceled

Berkshire County Board of REALTORS #246627

—
06/04/2025

Listed (Active)

Berkshire County Board of REALTORS #246627

$2,200,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 20 East Dugway Road

Taxable ValueLand$601,700Additions$583,700Total$1,185,400
Tax Record2025$10,728 ($894 / month)
Home Facts
Beds0Lot Size784,080 SqFtStyleSingle Family ResidenceZoningR-1ACountyBERKSHIREAPNLENO M:17 B:054 P:0000 U:00

Schools near 20 East Dugway Road

This home is within Lenox School District.
Rating
School
Type
Grades
Distance
Morris Elementary
Public - PK to 5
Lenox Memorial High School
Public - 6 to 12
The Montessori School of the Berkshires
Private - PK to 8
Berkshire Christian Schools
Private - PK to 12
Rating
School
Distance
Morris Elementary
PublicPK to 5

Lenox Memorial High School
Public6 to 12

The Montessori School of the Berkshires
PrivatePK to 8

Berkshire Christian Schools
PrivatePK to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 20 East Dugway Road, Lenox, MA 01240

20 East Dugway Road is a single family home for sale in Lenox, MA 01240. This property was listed for sale on May 21, 2026 by WILLIAM PITT SOTHEBY'S - LENOX, it's currently listed at $1,650,000. This listing's school district is Lenox School District. Nearby schools include Morris Elementary, Lenox Memorial High School and The Montessori School of the Berkshires. 20 East Dugway Road is a 7-bed, 7-bath, 5,693 sqft single family home built in 1921.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of WILLIAM PITT SOTHEBY'S - LENOX, Nick Geranios; WILLIAM PITT SOTHEBY'S - LENOX, Carrie Wright

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.