349 Old Stockbridge Rd, Lenox, MA 01240
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349 Old Stockbridge Rd, Lenox, MA 01240
349 Old Stockbridge Rd, Lenox, MA 01240
349 Old Stockbridge Rd, Lenox, MA 01240
349 Old Stockbridge Rd, Lenox, MA 01240
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$ 2,295,000
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349 Old Stockbridge Rd Lenox, MA 01240

31 Beds

29 Baths

38,415 SqFt


UPDATED:

Key Details

Property Type Single Family Home

Listing Status Active

Purchase Type For Sale

Square Footage 38,415 sqft

Price per Sqft $59

MLS Listing ID 250639

Style Historic

Bedrooms 31

Full Baths 14

Half Baths 15

Year Built 1903

Annual Tax Amount $88,477

Tax Year 2026

Lot Size 11.900 Acres

Acres 11.9

Lot Dimensions 2180x704x2297x88

Source Berkshire County Board of REALTORS®

Property Description

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.

Location

State MA

Area Middle Registry

Direction From Lenox: Old Stockbridge Road past Elm Court Estates. Property on left. From Lee/Stockbridge: Old Stockbridge Road, property on right.

Rooms

Basement Walkout, Interior Access, Full, Concrete Floor

Interior

Interior Features Alarm System, Backup Generator, High Speed Wiring

Heating Nat Gas, Oil, Boiler, Forced Air

Flooring Carpet, Ceramic Tile, Laminate, Linoleum, Wood

Appliance Built-In Gas Oven, Counter Grill, Dishwasher, Freezer, Microwave, Range, Range Hood, Refrigerator, Steam Oven

Exterior

Exterior Feature Pool - In Ground, Fenced-Partially, Patio

Parking Features false

Garage Description Off Street

View Seasonal, Scenic, Hill/Mountain, Distant

Roof Type Asphalt Shingles,Membrane,Metal

Porch true

Garage false

Building

Lot Description Paved Drive, Irregular Shape

Sewer Private Sewer

Water Public

Architectural Style Historic

Schools

Elementary Schools Morris

Middle Schools Lenox Memorial

High Schools Lenox Memorial


Listed by BIRCH PROPERTIES

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349 Old Stockbridge Rd