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Redefining Boston Real Estate

349 Old Stockbridge Rd, Lenox, MA

Lenox Single Family Get directions

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Unit Information

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 buildings added during its later evolution into an educational campus. Much of the character of the original country house remains, including handsome woodwork, substantial fireplaces, gracious rooms, and a beautiful ballroom. Most recently used for classrooms and administrative functions, the mansion was originally designed as a residence, with bedrooms on its upper floors.Beyond the main house are 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, offices, recreation, wellness, or a multi-generational Berkshire estate, subject to applicable approvals.The gymnasium could accommodate fitness, indoor tennis, pickleball, squash, or other private amenities. Existing infrastructure includes public water, multiple electrical services, mixed heating systems, central air in the dormitories and gymnasium, commercial sprinklering in select buildings, extensive parking, and established internal circulation.Hillcrest currently operates on the campus under a lease through June 2027 and presently anticipates vacating in February/March 2027.This offering is for 349 Old Stockbridge Road only. The property is also marketed as part of a combined offering with 40 Frothingham Crossing; see MLS #73518284.For its next steward, Overlee offers the rare chance to inherit not simply a house, but an entire Berkshire estate—historic architecture, expansive grounds, and a collection of buildings ready to support a new vision.Offered at $2,295,000.

Additional Details
Status: ACT
Type: Single Family, Single Family Residence
Zip Code: 01240
Parking
Garage Capacity: 99
Parking: Paved,Detached,Off Street,Unpaved
Parking Spaces: 99
Rooms and Dimensions
Total Rooms: 99
Has Basement: Yes
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$2,295,000

  • Listing ID: 73567764
  • Bedrooms: 31
  • Full Baths: 14
  • Half Baths: 15
  • Living Area: 38,415 sqft Convert
  • Lot Size: 518,364 sqft Convert
  • Acres: 11.9

  • View description
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Luxury Residential Group

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Content © 2026 MLS Property Information Network, Inc. The information in this listing was gathered from third party resources including the seller and public records. Listing information provided courtesy of Selina Lamb of Birch Properties. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations or warranties as to the accuracy of this information.

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