349 Old Stockbridge Rd Lenox, MA 01240
34 Beds
31 Baths
40,241 SqFt
UPDATED:
Key Details
Property Type Single Family Home
Listing Status Active
Purchase Type For Sale
Square Footage 40,241 sqft
Price per Sqft $79
MLS Listing ID 249508
Style Historic
Bedrooms 34
Full Baths 16
Half Baths 15
Year Built 1903
Annual Tax Amount $99,186
Tax Year 2026
Lot Size 16.670 Acres
Acres 16.67
Lot Dimensions 2180x704x2297x88
Source Berkshire County Board of REALTORS®
Property Description
At the center of the offering is Overlee, a distinguished Berkshire estate built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan / Jacobean Revival style. Over time, the estate evolved into a fully integrated campus, thoughtfully organized around the original mansion and supported by a collection of dormitory residences, academic and administrative buildings, dining infrastructure, and recreational facilities. Today, the property offers scale and infrastructure that are increasingly difficult to replicate in the Berkshires: 32 dormitory-style bedrooms across multiple buildings, shared common and staff housing spaces, a multi-level academic and dining center, and a substantial gymnasium well-suited for athletics, wellness programming, or event use. Existing systems include public water, commercial sprinklering, mixed heating systems, and electrical capacity up to 600 amps in select buildings.
The offering also includes 40 Frothingham Crossing, a 1,826 SF mid-century residence set on 4.74± acres across three contiguous parcels, offering flexibility for owner occupancy, guest accommodations, staff housing, or future subdivision and development planning.
While currently operated as an educational campus, the property's scale, layout, and existing infrastructure create compelling long-term potential for a range of future uses.
The combined acreage and campus framework lend themselves to a variety of possibilities, including educational or nonprofit continuation, retreat or wellness campus, medical or therapeutic use, hospitality or inn redevelopment, residential or senior living concepts, or a mixed-use institutional setting.
Importantly, the property is not listed on the National Historic Registry nor designated as a Lenox "Great Estate," which may allow for greater flexibility in future planning.
All buyers are encouraged to conduct their own due diligence regarding potential uses and approvals with the Town of Lenox.
Hillcrest Educational Center currently occupies the property under a tenancy expected to conclude in February 2027, providing near-term continuity while allowing time for planning, permitting, and phased repositioning.
Offered at $3,750,000 (combined offering).
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