20 E Dugway Rd
Lenox, MA 01240
7 Beds
6.5 Baths
5,693 sqft (on 36.40 acres)
$1,650,000
$1,650,000
7 Beds
6.5 Baths
5,693 sqft
(on 36.40 acres)
Local Information
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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. 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.
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.
Home Highlights
Parking
4 Car Garage
Outdoor
Porch, Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
$290
Listed
28 days ago
Home Details for 20 E Dugway Rd
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Interior Details Basement: Unfinished,Interior Entry,Bulk headNumber of Rooms: 18 |
Beds & Baths Number of Bedrooms: 7Number of Bathrooms: 7Number of Bathrooms (full): 6Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 5693 Square Feet |
Appliances & Utilities Utilities: Trash Private, Cable AvailableAppliances: Dishwasher, Dryer, Range, Refrigerator, WasherDishwasherDryerRefrigeratorWasher |
Heating & Cooling Heating: Propane,Oil,Electric,Boiler,Hot Water,Fireplace(s)Has CoolingAir Conditioning: ElectricHas HeatingHeating Fuel: Propane |
Fireplace & Spa Has a Fireplace |
Gas & Electric Electric: 100 Amp Service |
Windows, Doors, Floors & Walls Window: Skylight(s)Flooring: Ceramic Tile, Laminate, Linoleum, Wood |
Levels, Entrance, & Accessibility Accessibility: Accessible Bedroom, Accessible Full Bath, 1st Flr Bdrm w/BathFloors: Ceramic Tile, Laminate, Linoleum, Wood |
View Has a ViewView: Pasture |
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Exterior Home Features Roof: Asphalt Shingles MembranePatio / Porch: Porch, Deck, PatioFencing: PartialOther Structures: Barn/StableExterior: Privacy, Deciduous Shade Trees, Mature Landscaping, Landscaped |
Parking & Garage Number of Garage Spaces: 4Number of Covered Spaces: 4Other Parking: Garaged & Off-StreetHas a GarageHas an Attached GarageParking Spaces: 4Parking: Garaged & Off-Street |
Frontage Not on Waterfront |
Water & Sewer Sewer: Private Sewer |
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Days on Market: 28 |
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Year Built Year Built: 1921 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch,NE Farmhouse,Colonial,Cottage |
Property Information Parcel Number: M:17 B:054 P:0000 U:00 |
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Price List Price: $1,650,000Price Per Sqft: $290 |
Status Change & Dates Possession Timing: Close Of Escrow |
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MLS Status: Active |
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Direction & Address City: Lenox |
School Information Elementary School: MorrisJr High / Middle School: Lenox MemorialHigh School: Lenox Memorial |
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Listing Agent Listing ID: 249647 |
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Building Area Building Area: 5693 Square Feet |
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Lot Area: 36.4 Acres |
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BasementMls Number: 249647 |
Last check for updates: about 13 hours ago
Listing courtesy of Nick Geranios, (413) 822-6598
WILLIAM PITT SOTHEBY'S - LENOX
Carrie Lobovits Wright, (413) 212-1865
WILLIAM PITT SOTHEBY'S - LENOX
Source: BCMLS, MLS#249647
Also Listed on BCMLS.
Market trends in Lenox
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
37
7MoM
Price History for 20 E Dugway Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 05/22/2026 | $1,650,000 | Listed For Sale | BCMLS #249647 |
| 11/29/2025 | $1,750,000 | ListingRemoved | BCMLS #246627 |
| 10/10/2025 | $1,750,000 | PriceChange | BCMLS #246627 |
| 07/14/2025 | $1,950,000 | PriceChange | BCMLS #246627 |
| 06/12/2025 | $2,200,000 | Listed For Sale | BCMLS #246627 |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $10,728 |
| Assessment | $1,185,400 |
Home facts updated by county records
Comparable Sales for 20 E Dugway Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.47 | Single-Family Home | $2,200,000 | 03/06/26 | 6 | 6.5 | 7,143 | |
0.40 | Single-Family Home | $1,250,000 | 09/19/25 | 4 | 4.5 | 3,190 | |
0.60 | Single-Family Home | $1,550,000 | 08/06/25 | 4 | 2.5 | 4,049 | |
0.72 | Single-Family Home | $1,800,000 | 01/06/26 | 12 | 10.5 | 7,979 | |
0.43 | Single-Family Home | $625,000 | 08/12/25 | 3 | 2 | 1,687 | |
0.66 | Single-Family Home | $615,250 | 06/25/25 | 4 | 2 | 1,600 | |
0.82 | Single-Family Home | $638,000 | 04/15/26 | 4 | 2.5 | 1,856 | |
1.14 | Single-Family Home | $1,050,000 | 12/18/25 | 4 | 4.5 | 2,995 | |
1.66 | Single-Family Home | $4,000,000 | 06/10/26 | 7 | 7 | 13,261 | |
0.55 | Single-Family Home | $399,000 | 11/25/25 | 3 | 1 | 1,344 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETBarbara K. Greenfeld, Broker, ROBERTS & ASSOC. REALTY, INC
OFF MARKETMary Jo Piretti-Miller, PIRETTI REAL ESTATE
SOLDSEP 19, 2025Mary Jo Piretti-Miller, PIRETTI REAL ESTATE
OFF MARKETPamela Roberts, ROBERTS & ASSOC. REALTY, INC- FOR SALE1.9 ACRESMaureen White-Kirkby, BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
SOLDMAR 6, 2026Maggie Gavin, WILLIAM PITT SOTHEBY'S - LENOX
OFF MARKETMary Jo Piretti-Miller, PIRETTI REAL ESTATE
OFF MARKETPamela Roberts, ROBERTS & ASSOC. REALTY, INC
Assigned Schools
These are the assigned schools for 20 E Dugway Rd.
- Lenox Memorial High School
- 6-12
- Public
- 430 Students
6/10GreatSchools RatingParent Rating Averagegreat education, great communication and built many friendships. Very inclusive of my son coming in during 7th grade without knowing a sole, He had long-lasting friendships from day 1.Parent Review5y ago - Morris Elementary
- PK-5
- Public
- 320 Students
8/10GreatSchools RatingParent Rating AverageOutstanding. Our children feel part of a community, are known and looked after. Class sizes are private school small—often 15 or 16 students. The school is small enough for everyone to feel known as an individual yet big enough to have some choices when it comes to friends. Specialists are excellent. I have complete confidence dropping our children off that they are safe, that anything that comes upwill be handled appropriately, and that they are learning from educators who enjoy being there, love the kids, and love what they do. Really what more can you ask for when it comes down to it? We have personally experienced several instances of care for our children that were moving tributes to the excellent people that make up this school community. I do think more could be done for gifted students in the early grades as attempts to provide enrichment have been uneven, but we have appreciated the efforts of teachers to try to provide some differentiated learning opportunities. In public schools without formal gifted programs (as is the case in MA I believe?) this uneven experience is bound to be the case. I think many of us wish there was more diversity in our town and county but the school choice policy does provide some infusion of diversity. Finally, throughout the pandemic the communication from the superintendent has been regular and clear. We were amazed at the ability of the teachers to transition to online education and provide a sense of emotional support and social connection. Our children continued to practice skills and learn a few new ones before summer hit. I imagine if school is virtual again this fall, it will only be improved. The biggest thing is we trust the school to make careful, sound choices to the students.Parent Review5y ago 
Check out schools near 20 E Dugway Rd.
What Locals Say about Lenox
At least 23 Trulia users voted on each feature.
96 % Say car is needed
91 % Say yards are well-kept
83 % Say it's dog friendly
80 % Say parking is easy
78 % Say people would walk alone at night
72 % Say kids play outside
69 % Say there's wildlife
68 % Say it's walkable to grocery stores
68 % Say there's holiday spirit
61 % Say it's walkable to restaurants
60 % Say it's quiet
60 % Say streets are well-lit
56 % Say there are sidewalks
56 % Say there are community events
52 % Say they plan to stay for at least 5 years
51 % Say neighbors are friendly
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Nick Geranios, WILLIAM PITT SOTHEBY'S - LENOX
Agent Phone: (413) 822-6598
IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed to be reliable but not guaranteed.
The data relating to real estate for sale on this website comes from Berkshire County Board of Realtors and the Broker Reciprocity Program. Copyright 2026 Berkshire County Board of Realtors. All rights reserved.
The data relating to real estate for sale on this website comes from Berkshire County Board of Realtors and the Broker Reciprocity Program. Copyright 2026 Berkshire County Board of Realtors. All rights reserved.
20 E Dugway Rd, Lenox, MA 01240 is a 7 bedroom, 7 bathroom, 5,693 sqft single-family home built in 1921. This property is currently available for sale and was listed by BCMLS on May 22, 2026. The MLS # for this home is MLS# 249647.