349 Old Stockbridge Rd, Lenox Township, Massachusetts image 1
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349 Old Stockbridge Rd

Lenox Township, MA 01240
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$3,195,000 $13,470/Mo
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Bed 34

Bed

Bath 31

Bath

SqFt40,241

Sqft

Acres16.67

Acres(Lot)

349 Old Stockbridge Road and 40 Frothingham Crossing together represent a rare 16.76± acre contiguous institutional campus and redevelopment opportunity in the heart of Lenox--one of the Berkshires' most established and sought-after destination markets. At the center of the offering is Overlee, a distinguished Berkshire estate built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan / Jacobean Revival style. Over time, the estate evolved into a fully integrated campus, thoughtfully organized around the original mansion and supported by a collection of dormitory residences, academic and administrative buildings, dining infrastructure, and recreational facilities. Today, the property offers scale and infrastructure that are increasingly difficult to replicate in the Berkshires: 32 dormitory-style bedrooms across multiple buildings, shared common and staff housing spaces, a multi-level academic and dining center, and a substantial gymnasium well-suited for athletics, wellness programming, or event use. Existing systems include public water, commercial sprinklering, mixed heating systems, and electrical capacity up to 600 amps in select buildings. The offering also includes 40 Frothingham Crossing, a 1,826 SF mid-century residence set on 4.74± acres across three contiguous parcels, offering flexibility for owner occupancy, guest accommodations, staff housing, or future subdivision and development planning. While currently operated as an educational campus, the property's scale, layout, and existing infrastructure create compelling long-term potential for a range of future uses. The combined acreage and campus framework lend themselves to a variety of possibilities, including educational or nonprofit continuation, retreat or wellness campus, medical or therapeutic use, hospitality or inn redevelopment, residential or senior living concepts, or a mixed-use institutional setting. Importantly, the property is not listed on the National Historic Registry nor designated as a Lenox "Great Estate," which may allow for greater flexibility in future planning. All buyers are encouraged to conduct their own due diligence regarding potential uses and approvals with the Town of Lenox. Hillcrest Educational Center currently occupies the property under a tenancy expected to conclude in February 2027, providing near-term continuity while allowing time for planning, permitting, and phased repositioning. Offered at $3,750,000 (combined offering).

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Detail Ic Property Details

Property Type : Residential

Price : $3,195,000

AD Id : 78482659

MLS Id : 249508

Beds : 34

Lot Size : 16.67 Acres

Living Area Size : 40,241 Sq. Ft

Tax Amount : $99,186.56

Year Built : 1903

County : Berkshire

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Feature Features

  • Bedroom Information

    Total beds: 34

    Bathroom Information

    Total Baths: 31 Full Baths: 16 Half Baths: 15

    Room Information

    Rooms Total: 118 Has Basement: Yes Basement: Concrete, Walk-Out Access, Full

  • Flooring Information

    Vinyl, Carpet, Ceramic Tile, Laminate, Linoleum, Wood

  • Roofing Information

    Rubber, Membrane, Metal

  • Interior Features

    Roof: Rubber, Membrane, Metal Appliances: Gas Oven, Oven, Built-In Gas Oven, Dishwasher, Freezer, Microwave, Range, Range Hood, Refrigerator

  • Heating & Cooling

    Has Heating: Yes Heating: Natural Gas, Oil, Forced Air

  • Building Information

    Year Built: 1903 Building Area Total: 40241 Patio And Porch Features: Patio Pool Features: In Ground Private Pool: No View: Mountain(s), Scenic

  • Lot Information

    Lot Dimensions: 2180x704x2297x88 Main Square Feet: 16.67 Acres Lot Size Acres: 16.67 Lot Size Square Feet: 726145 Lot Description: Irregular Lot

  • Listing Price Information

    Listing Price: $3195000 Original Price: $3750000

  • Tax Information

    Parcel Number: M: 01 B: 003 P: 0000 U: 00 Tax Year: 2026 Annual Tax: $99186.56

  • Parking Information

    Paved, Off Street

  • School Information

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

  • Location Information

    Direction: From Lenox: Old Stockbridge Road past Elm Court Estates. Property on left. From Lee/Stockbridge: Old Stockbridge Road, property on right. WaterSource: Public Security Features: Security System
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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 @ 04:55

MLS: 249508 LISTED BY: Selina Lamb, BIRCH PROPERTIES 415-515-3750 SOURCE: Berkshire County Board of REALTORS

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