20 E Dugway Rd, Lenox Township, Massachusetts image 1
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20 E Dugway Rd

Lenox Township, MA 01240
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$1,650,000 $6,956/Mo
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Bed 7

Bed

Bath 7

Bath

SqFt5,693

Sqft

Acres36.40

Acres(Lot)

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 li ving 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.

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Detail Ic Property Details

Property Type : Residential

Price : $1,650,000

AD Id : 79125146

MLS Id : 249647

Beds : 7

Lot Size : 36.40 Acres

Living Area Size : 5,693 Sq. Ft

Tax Amount : $10,728

Year Built : 1921

Garage : 4

County : Berkshire

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Feature Features

  • Bedroom Information

    Total beds: 7

    Bathroom Information

    Total Baths: 7 Full Baths: 6 Half Baths: 1

    Room Information

    Rooms Total: 18 Has Basement: Yes Basement: Unfinished

  • Flooring Information

    Vinyl, Ceramic Tile, Laminate, Linoleum, Wood

  • Roofing Information

    Rubber, Membrane

  • Interior Features

    In-Law Floorplan, Vaulted Ceiling(s), Walk-In Closet(s) Roof: Rubber, Membrane Appliances: Dishwasher, Dryer, Range, Refrigerator, Washer Window Features: Skylight(s)

  • Heating & Cooling

    Has Heating: Yes Heating: Propane, Oil, Electric, Hot Water Has Cooling: Yes Cooling: Electric

  • Building Information

    Year Built: 1921 Building Area Total: 5693 Patio And Porch Features: Deck, Patio, Porch Private Pool: No

  • Lot Information

    Lot Dimensions: Irregular Main Square Feet: 36.4 Acres Lot Size Acres: 36.4 Lot Size Square Feet: 1585584 Lot Description: Wooded, Corner Lot, Irregular Lot, Pasture, Landscaped, Few Trees

  • Listing Price Information

    Listing Price: $1650000

  • Tax Information

    Parcel Number: M:17 B:054 P:0000 U:00 Tax Year: 2025 Annual Tax: $10728

  • Parking Information

    Off Street, Attached

    Garage Information

    Has Garage: Yes Has Attached Garage: Yes Garage Space: 4

  • School Information

    Elementary School: Morris
    Junior High School: Lenox Memorial
    Senior High School: Lenox Memorial

  • Utility Information

    Cable Available

  • Location Information

    Direction: 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 WaterSource: Public
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
18 Willow Ln, Lenox Township, MA, 01240 $595,000 3 2 1,562 0.84 Acre
399 Under Mountain Rd, Lenox Township, MA, 01240 $7,975,000 8 7 9,364 11.45 Acres

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.

ByOwner last updated this listing 10/06/2026 @ 02:07

MLS: 249647 LISTED BY: Nick Geranios, WILLIAM PITT SOTHEBY'S - LENOX 413-637-4402 SOURCE: Berkshire County Board of REALTORS

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