349 Old Stockbridge Rd, Lenox, MA 01240 (MLS# 249507)


$3,750,000
349 Old Stockbridge Rd
Lenox, MA 01240
MLS# 249507
40241 sqft


Overlee House - Front View
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Overlee House - Front View Overlee House - Entrance Full Campus Aerial View Overlee House Entrance Overlee House - Rear Facade Overlee House - Exterior Detail large Stone Wall Stairs Overlee House - Exterior Detail Overlee House - Ballroom Toward Entrance Overlee House - Ballroom From Entrance Overlee House - Ballroom Alcove Overlee House - Ballroom fireplace Detai Overlee House - Dining Room Overlee House - Trim Detail Overlee House - Dining Room Overlee House - Trim Detail Overlee House - 2nd Floor Room Overlee House - 2nd Floor Room Overlee House - Trim Detail Overlee House - 2nd Floor Room Overlee House - View from Dining Room Overlee House - Woodwork Detail Overlee House - Woodwork Detail Overlee House-Interior Staircase Detail Overlee House - Woodwork Detail Campus Aerial Dormitory - Dellea Hall Dormitory - Dellea Hall Common Room Dormitory - Dellea Hall Bedroom Dormitory - Miller Hall Common Room Dormitory - Miller Hall Exterior Gymnasium 40 Frothingham - Exterior 40 Frothingham - House and Garden 40 Frothingham - Living Room to Dining 40 Frothingham - Inglenook w Fireplace 40 Frothingham - Living Room (VS) 40 Frothingham - Dining Area 40 Frothingham - Dining to Florida Room 40 Frothingham - Dining to Kitchen 40 Frothingham - Kitchen 40 Frothingham - Primary BR w Ensuite 40 Frothingham - BR Virtually Staged 40 Frothingham - Florida Room to Studio 40 Frothingham - Florida Room 40 Frothingham - Studio 40 Frothingham - Studio 40 Frothingham - Gardens 40 Frothingham - Exterior Entry Overlee - Campus Aerial Looking South Aerial Overview from 40 Frothingham Overlee - Aerial from South Full Property Orthogonal View Overlee House - Aerial View

Property Description
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.

Details
Maps
Documents
Contract Information
Original List Price: 3750000
Limited Service: No
Agent Interest: None
Current Price: $3,750,000
Status: Active
List Date: 2026-05-13
List Price: $3,750,000
Location, Tax & Legal
Assess Amt: 3625600
Assessed Year: 2025
Taxes: 99186.56
Tax Year: 2026
Page: 74
Registry: Middle Registry
Street #: 349
Street Name: Old Stockbridge
Street Ext: Rd
State/Province: MA
Postal Code: 01240
Map Ref: M: 01 B: 003 P: 0000 U: 00
General Property Description
Surveillance: Yes
Realtor.COM Type: Commercial
Total # Bedrooms: 34
Total Bathrooms: 0
Parking Spaces: 100
Parking Spaces Type: Off Street
Sq Ft Source: Assessor
Lot Square Footage: 726145
Year Built Source: Assessor
Lot Size SqFt: 726145
Betterment: No
Sq Ft Liv Apx: 40241
Year Built Apx: 1903
Acres Apx: 16.67
Remarks & Misc
Directions: From Lenox: Old Stockbridge Road past Elm Court Estates. Property on left. From Lee/Stockbridge: Old Stockbridge Road, property on right.
Marketing/Headline: 16.76± Acre Lenox Campus | Contiguous Institutional & Redevelopment Opportunity
Basement
Concrete Floor: 1
Full: 1
Interior Access: 1
Walkout: 1
Exterior Amenities
Inground Pool: 1
Fuel
Nat Gas: 1
Oil: 1
Hot Water
Electric: 1
Nat Gas: 1
On Demand: 1
Interior Amenities
Air Cond: 1
Alarm System: 1
Emp Break Room: 1
Emp Kitchen: 1
Sprink Sys-Wet: 1
Internet Service
Cable Available: 1
Lead Paint
Unk: 1
Lot Description
Irregular Shape: 1
Paved Drive: 1
Business Type
Education/School: 1
Underground Oil Tank
Yes: 1
Features
Attic: 1
Basement: 1
Outbuilding: 1
Water
Public: 1
Right to Farm Comm
Yes: 1
Sewer
Public: 1
Electric Type
400 Amp: 1
Circuit Breaker: 1
Individual Meter: 1
Construction
2x6 Walls: 1
Concrete: 1
Masonry: 1
Wood Frame: 1
Roof
Asphalt: 1
Membrane: 1
Metal: 1
Heat/Cool
Boiler: 1
Built-In A/C Unit: 1
Central AC: 1
Forced Air: 1
Hot Water: 1
Steam: 1
Window A/C Unit: 1
Bathrooms
# 1/2 Bath: 15
# Full Bath: 16
Zoning
Residential: 1
Insulation
Asbestos: 1
Fiberglass: 1
Seller Disc
No: 1
Appliances Included
Built-In Electric Oven: 1
Counter Grill: 1
Dishwasher: 1
Freezer: 1
Microwave: 1
Range: 1
Range Hood: 1
Refrigerator: 1
Washer: 1
Possession
Negotiable: 1
Status Change Info
Status Change Date: 2026-05-13
Property Features
Business Type: Education/School
Underground Oil Tank: Yes
Water: Public
Sewer: Public
Right to Farm Comm: Yes
Lot Description: Irregular Shape; Paved Drive
Electric Type: 400 Amp; Circuit Breaker; Individual Meter
Interior Amenities: Air Cond; Alarm System; Emp Break Room; Emp Kitchen; Sprink Sys-Wet
Internet Service: Cable Available
Exterior Amenities: Inground Pool
Construction: 2x6 Walls; Concrete; Masonry; Wood Frame
Roof: Asphalt; Membrane; Metal
Basement: Concrete Floor; Full; Interior Access; Walkout
Features: Attic; Outbuilding
Fuel: Nat Gas; Oil
Hot Water: Electric; Nat Gas; On Demand
Insulation: Asbestos; Fiberglass
Lead Paint: Unk
Zoning: Residential
Seller Disc: No
Appliances Included: Built-In Electric Oven; Counter Grill; Dishwasher; Freezer; Microwave; Range; Range Hood; Refrigerator; Washer
Possession: Negotiable
Supplements
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).

Listing Office: BIRCH PROPERTIES
Listing Agent: Selina Lamb

Last Updated: May - 14 - 2026

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