349 Old Stockbridge Rd

Lenox, MA 01240

$3,750,000 PRICE
40,241 Sqft
16.67 Acres
1903 Built
$93 Price/Sqft

349 Old Stockbridge Road and 40 Frothingham Crossing together represent a rare 16.76± acre contiguous institutional campus and redevelopment opportunity in the heart of Lenox--one of the Berkshires' most established and sought-after destination markets. 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).

Additional Information

LOT DETAILS

WATER: Public

EXTERIOR FEATURES

ROOF: Rubber, Membrane, Metal, Asphalt
EXTERIOR FEATURES: Pool (In Ground)

INTERIOR FEATURES

APPLIANCES INCLUDED: Electric Oven, Washer, Refrigerator, Range Hood, Range, Microwave, Freezer, Dishwasher, Built-In Electric Oven
HEAT: Natural Gas, Oil, Pellet Stove, Forced Air, Hot Water

ADDITIONAL INFORMATION

BASEMENT DESCRIPTION: Concrete, Walk-Out Access, Full
DAYS ON MARKET: 29
ELECTRICAL FEATURES: 200+ Amp Service, Circuit Breakers
LIVING AREA SQFT: 40241
ON MARKET DATE: 2026-05-13
PARKING: Off Street
SEWER: Public Sewer
TAX YEAR: 2026
YEAR BUILT: 1903
ZONING: Residential

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Location for 349 Old Stockbridge Rd, Lenox, MA

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Schools for 349 Old Stockbridge Rd, Lenox, MA

Our community offers residents access to a number of fine private and public schools for all grade levels. Please read below for information on each of the schools in our area.

Elementary School
Unspecified
Middle School
Unspecified
High School
Unspecified

Private Schools

SCHOOL	LOCATION	GRADE
The Montessori School of the Berkshires	21 Patterson Road Lee, MA 01238	PK - 8
Berkshire Country Day School	55 INTERLAKEN ROAD, ROUTE 183 Stockbridge, MA 01262	PK - 8
Frontline Church School	160 High Street Lee, MA 01238	11
St Mary's School	115 Orchard Street Lee, MA 01238	PK - 8
Berkshire Christian Schools	PO BOX 1980 Lenox, MA 01240	PK - 12
Berkshire Waldorf High School	6 Main Street Stockbridge, MA 01262	9 - 12

*UG = ungraded.
Detailed school information provided by GreatSchools.org © . All rights reserved.

Public and private school information is provided by sources including GreatSchools.org and various MLS services including the One Key, SMARTMLS, NCMLS, DARMLS and Greenwich MLS, and is subject to the terms of use on those sites. William Pitt and Julia B. Fee Sotheby’s International Realty believes the information provided by these sources to be accurate but will not be held responsible if any data as well as information such as school districts for listings is inaccurate.

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Community

Lenox

Berkshire County, Massachusetts

Lenox, located in the heart of the Berkshires, is a primary summer resort destination and home to many of the region’s most visited attractions, including Tanglewood Music Center and the Edith Wharton...

Market Stats for Lenox, Massachusetts

An exclusive report that informs you of residential real estate sales activity and trends in Lenox, Massachusetts.

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306 Main Street
Great Barrington, MA 01230
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