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31 Beds
29 Baths
38,415 sqft

$2,295,000

349 Old Stockbridge Rd, Lenox MA, 01240

Price per sqft$59.74
Built in1903
Property size38,415 sqft
Property typeResidential
Courtesy of BIRCH PROPERTIES, Selina Lamb Listing Contact: 413-331-7483

Overview

Active

Listed Aug 25, 2026

Updated 2 weeks ago

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.

$15,269/mo

Est. mortgage payment based on a $2,295,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
250639

Interior Features

Bedrooms
31
Bathrooms
29
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
11.9 Acres

Other Property Details

Taxes
$88,477
Tax Frequency
Annually
View
Yes
Pool
Yes

Broker Reciprocity Courtesy of Selina Lamb, BIRCH PROPERTIES Listing Contact: 413-331-7483  

 

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