349 Old Stockbridge Rd

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).