349 Old Stockbridge Rd

Taxes: $88,477 (2026)

About this home

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.

Property details

Sewer

On-Site

Style

Low-Rise, Duplex, Chateauesque

Water

City/Town Water

Cooling

Central Air, Wall AC, Ductless Mini-Split System

Heating

Central Heat, Forced Air, Individual

Type

Detached

Flooring

Wood, Tile, Wall to Wall Carpet, Laminate

Appliances

Dishwasher, Microwave, Indoor Grill, Refrigerator, Freezer, Washer, Dryer, Vent Hood

Construction

Aluminum, Brick

Roof

Metal, Asphalt/Composition Shingles

Garage

Detached

Lot

Paved Drive, Underground Storage Tank, Scenic View(s)

Parking

1-10 Spaces, Paved Driveway, Unpaved Driveway

Basement

Walk Out, Interior Access, Concrete Floor

Electric

100 Amps, 200 Amps

Exterior

Patio, Pool - Inground, Storage Shed, Sprinkler System