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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$2,295,000 $9,675/Mo
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Bed 31

Bed

Bath 29

Bath

SqFt38,415

Sqft

Acres11.90

Acres(Lot)

A singular opportunity to reimagine one of Lenox's historic Berkshire estates. Set on 11.90± acres just minutes from downtown Lenox and the cultural attractions of the Berkshires, Overlee was built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan/Jacobean Revival style. The original mansion remains at the heart of the property, surrounded by broad lawns and a collection of buildings added during its later evolution into an educational campus. Despite decades of institutional use, much of the character of the original country house remains. Handsome woodwork, substantial fireplaces, gracious rooms, and a beautiful ballroom recall Overlee's Gilded Age origins. Most recently used for classrooms and administrative functions, the mansion was originally designed as a residence, with bedrooms on its upper floors, creating an intriguing foundation for its return to residential use. Beyond the main house, the campus includes two dormitory residences with approximately 24 bedrooms and shared common spaces, a separate multi-level building with commercial kitchen and dining facilities, classrooms, offices, library, conference and infirmary spaces, a substantial gymnasium, and additional support buildings. For a residential buyer, this unusual collection offers possibilities for guest and staff accommodations, studios and offices, recreation, wellness, or a multi-generational Berkshire estate, subject to applicable approvals. The gymnasium offers particularly compelling recreational potential, with space adaptable for fitness, indoor tennis, pickleball, squash, or other private amenities. Existing infrastructure includes public water, multiple electrical services, commercial sprinklering in select buildings, mixed heating systems, central air in the dormitories and gymnasium, extensive parking, and established internal circulation. Hillcrest Educational Center currently operates on the campus under a lease through June 2027 and presently anticipates vacating in February/March 2027. This offering is for the 349 Old Stockbridge Road campus only. The property is also being marketed as part of a separate combined offering with 40 Frothingham Crossing. See MLS #249508. For its next steward, Overlee offers the unusual chance to inherit not simply a house, but an entire Berkshire estate: a remarkable historic residence, expansive grounds, and a collection of buildings capable of supporting a deeply personal vision for how the property might live again. Offered at $2,295,000.

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Detail Ic Property Details

Property Type : Residential

Price : $2,295,000

AD Id : 90029367

MLS Id : 250639

Beds : 31

Lot Size : 11.90 Acres

Living Area Size : 38,415 Sq. Ft

Tax Amount : $88,477

Year Built : 1903

County : Berkshire

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Feature Features

  • Bedroom Information

    Total beds: 31

    Bathroom Information

    Total Baths: 29 Full Baths: 14 Half Baths: 15

    Room Information

    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: 38415 Patio And Porch Features: Patio Pool Features: In Ground Private Pool: No View: Mountain(s), Scenic

  • Lot Information

    Lot Dimensions: 2180x704x2297x88 Main Square Feet: 11.9 Acres Lot Size Acres: 11.9 Lot Size Square Feet: 518364 Lot Description: Irregular Lot

  • Listing Price Information

    Listing Price: $2295000

  • Tax Information

    Tax Year: 2026 Annual Tax: $88477

  • 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 10/07/2026 @ 14:53

MLS: 250639 LISTED BY: Selina Lamb, BIRCH PROPERTIES 415-515-3750 SOURCE: Berkshire County Board of REALTORS

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