349 Old Stockbridge Rd, Lenox, MA 01240 (MLS# 249508)


$3,750,000
349 Old Stockbridge Rd
Lenox, MA 01240
MLS# 249508
34 beds  |  31 baths  |  40241 sqft


Overlee House - Entrance
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Overlee House - Entrance Full Campus Aerial View Overlee House - Front View Overlee House - Entrance Overlee House - Rear Facade Overlee House - Exterior Detail 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 Detail 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
Accessory Dwelling Unit: No
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
Elem School: Morris
Middle School: Lenox Memorial
High School: Lenox Memorial
Assessed Year: 2026
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: Residential - Single Family
Total Bathrooms: 31
Parking Spaces Type: Off Street
Sq Ft Source: Assessor
Total Rooms: 118
Total Bedrooms: 34
Year Built Source: Assessor
Yr Blt Description: Approximate
Lot Size Dimensions: 2180x704x2297x88
Lot Size SqFt: 726145
Frontage Apx: 1775
Sq Ft Liv Apx: 40241
Total Full Baths: 16
Total Half Baths: 15
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: Lenox Estate: Rare Opportunity
Restrict Covenants
No: 1
Appliances Incl
Built-In Gas Oven: 1
Counter Grill: 1
Dishwasher: 1
Freezer: 1
Microwave: 1
Range: 1
Range Hood: 1
Refrigerator: 1
Steam Oven: 1
Basement
Concrete Floor: 1
Full: 1
Interior Access: 1
Walkout: 1
Exterior Amenities
Fenced-Partially: 1
Patio: 1
Pool - In Ground: 1
Flood Hazard Area
No: 1
Floor
Carpet: 1
Ceramic Tile: 1
Laminate: 1
Linoleum: 1
Wood: 1
Fuel
Nat Gas: 1
Oil: 1
Garage
Detached: 1
Heat/Cool/Vent
Boiler: 1
Central AC: 1
Forced Air: 1
Multizone: 1
Hot Water
Electric: 1
On Demand: 1
Interior Amenities
Alarm System: 1
Backup Generator: 1
High Speed Wiring: 1
Internet Service
Cable Available: 1
Lead Paint
Unk: 1
Lot Description
Irregular Shape: 1
Paved Drive: 1
Title V
Pass: 1
Title V Date
Title V Date: April 2025
Underground Oil Tank
Yes: 1
Water
Public: 1
Right to Farm Comm
Unk: 1
Sewer
Private: 1
Building Info
Exterior Color: Brick
Easement
Unk: 1
Survey
Unk: 1
Right of Way
Unk: 1
Electric Type
200 Amp: 1
400 Amp: 1
Circuit Breaker: 1
Individual Meter: 1
Views
Distant: 1
Hill/Mountain: 1
Scenic: 1
Seasonal: 1
Construction
2x6 Walls: 1
Concrete: 1
Masonry: 1
Wood Frame: 1
Roof
Membrane: 1
Metal: 1
Asphalt Shingles: 1
Style
Historic: 1
Zoning
Residential: 1
Insulation
Asbestos: 1
Fiberglass: 1
Seller Disc
No: 1
Exterior Siding
Brick: 1
Masonry: 1
Stucco: 1
Vinyl: 1
Possession
Negotiable: 1
Status Change Info
Status Change Date: 2026-05-13
Property Features
Restrict Covenants: No
Title V: Pass
Underground Oil Tank: Yes
Water: Public
Sewer: Private
Easement: Unk
Survey: Unk
Right of Way: Unk
Right to Farm Comm: Unk
Flood Hazard Area: No
Views: Distant; Hill/Mountain; Scenic; Seasonal
Lot Description: Irregular Shape; Paved Drive
Electric Type: 200 Amp; 400 Amp; Circuit Breaker; Individual Meter
Style: Historic
Interior Amenities: Alarm System; Backup Generator; High Speed Wiring
Internet Service: Cable Available
Exterior Amenities: Fenced-Partially; Patio; Pool - In Ground
Appliances Incl: Built-In Gas Oven; Counter Grill; Dishwasher; Freezer; Microwave; Range; Range Hood; Refrigerator; Steam Oven
Construction: 2x6 Walls; Concrete; Masonry; Wood Frame
Exterior Siding: Brick; Masonry; Stucco; Vinyl
Roof: Asphalt Shingles; Membrane; Metal
Basement: Concrete Floor; Full; Interior Access; Walkout
Floor: Carpet; Ceramic Tile; Laminate; Linoleum; Wood
Garage: Detached
Fuel: Nat Gas; Oil
Hot Water: Electric; On Demand
Insulation: Asbestos; Fiberglass
Lead Paint: Unk
Zoning: Residential
Seller Disc: No
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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