- 7
- beds
- 6 full · 1 half
- baths
- 5,693
- sqft
- 1921
- year built
- Status:
- Active
- MLS #:
- 249647
- County:
- Berkshire
- Listed By:
- Nick Geranios - WILLIAM PITT SOTHEBY'S - LENOX
- Agent Phone:
- (413) 822-6598
- Agent Email:
- ngeranios@wpsir.com
Sponsoring Broker: Derek Eisenberg, Continental Real Estate Group, Inc
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.
Highlights
- Residential
- Single Family Residence
- Built in 1921
- 36.4 Acre Lot
- 4 Car Garage
- 168 days on Market
-
- Bedrooms
- 7
-
- Bathrooms
- 6 full · 1 half
-
- Year Built
- 1921
-
- Architectural Style
- Ranch, Cottage, Colonial, NE Farmhouse
-
- Construction Materials
- Stucco, Brick
-
- Garage Spaces
- 4.0
-
- Parking Features
- Attached, Detached, Off Street
-
- Living Area
- 5693.0
-
- Interior Features
- Walk-In Closet(s), Vaulted Ceiling(s), In-Law Floorplan
-
- Appliances
- Dryer, Dishwasher, Refrigerator, Washer, Range
-
- Flooring
- Laminate, Vinyl, Linoleum, Ceramic Tile, Wood
-
- Heating
- Electric, Heat Pump, Propane, Hot Water, Oil
-
- Basement
- Unfinished
-
- Acres
- 36.4
-
- Lot Features
- Wooded, Corner Lot, Irregular Lot, Pasture
-
- Utilities
- Cable Available
-
- Water
- Private
-
- Area
- Middle Registry
-
- County
- Berkshire
-
- City
- Lenox
-
- Zip Code
- 01240
-
- High School
- Lenox Memorial
-
- Middle School
- Lenox Memorial
-
- Elementary School
- Morris
-
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Estimated Value
$1,607,994
$1,125,595 - $2,090,392
Source: Constellation Data Labs
Price History
| 05/22/2026 | Listed | $1,650,000 |
| Source: Berkshire County Board of REALTORS #249647 | ||
| 06/03/2025 | Off Market | — |
| Source: Berkshire County Board of REALTORS #246627 | ||
Source: MLS Data
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Frequently Asked Questions
How do I schedule a tour of 20 E Dugway Rd?
We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 20 E Dugway Rd.
They know residentials in the area well and can give you the guidance you need to buy with confidence.
How do I get more information about 20 E Dugway Rd?
Click Ask a Question to talk with our team. You already know it is a 7 bed, 6 bath, listed for $1,650,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Lenox, and can even get you in to see the property quickly.
How much is the monthly mortgage payment for 20 E Dugway Rd?
With a 20% down payment and a 30-year fixed loan at an illustrative 6.75% rate, the ez Mortgage Calculator estimates the monthly payment for 20 E Dugway Rd at around $9,840. This includes estimated property taxes and insurance.
Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.
How do I get pre-approved to buy 20 E Dugway Rd?
Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.
Or, let us connect you with our preferred local lender in Berkshire County. They will give you all of your available financing options, based on your specific situation and what is available to you.
Can I negotiate the asking price for 20 E Dugway Rd?
In most cases, yes. Whether 20 E Dugway Rd is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Lenox's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.
How do I make an offer on 20 E Dugway Rd?
We can handle that for you. Our preferred local agent specializes in residentials in Lenox and can guide you through every step of the offer process.
You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.
What is the price per square foot for this home?
This home is listed at $1,650,000 with 5,693 sqft of space—that comes out to approximately $290 per square foot.
How long has this property been on the market?
20 E Dugway Rd was listed on May 22, 2026, which means it's been on the market for 168 days.
Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.
When was this house built?
This home was built in 1921, making it approximately 105 years old.
What is the lot size of this property?
20 E Dugway Rd sits on a 36.4-acre lot, which is 1,585,584 square feet.
What schools are assigned to this property?
Based on MLS info, this home is zoned for:
- Elementary: Morris
- Middle: Lenox Memorial
- High: Lenox Memorial
Want to see how these schools compare? Check out our Berkshire County School Guide to see ratings, reviews, and more for the schools in the area.
What are the property taxes for 20 E Dugway Rd?
The most recent public record shows annual property taxes for 20 E Dugway Rd were approximately $10,728. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.
Is 20 E Dugway Rd still available for sale?
Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.
Source: ez Home Search, MLS Data
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Information from the Berkshire County Board of REALTORS®, Inc. or its Multiple Listing Service, Information herein believed to be accurate, but not warranted. All right, title and interest in the exclusively listed property information represented on this website was created, maintained and copyrighted by the Berkshire County Board of REALTORS®, and in copyrights therein, shall at all times remain vested in the Berkshire County Board of REALTORS®. As a Participant of the Berkshire County Multiple Listing Service, this company was granted a lease to use this information in accordance with all rules and regulations of the Service. This information is being provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Copyright ©2026 Berkshire County Multiple Listing Service. All rights reserved.