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349 Old Stockbridge Rd, Lenox MA 01240

$2,295,000

Estimated $21,514/month Calculator

Single Family

31 Bedrooms

Baths

38415

Total Parking: 99

518,364 (11.90)

Built in 1903

A singular opportunity to reimagine one of Lenox's historic Berkshire estates. Set on 11.90± acres just minutes from downtown Lenox and the cultural attractions of the Berkshires, Overlee was built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan/Jacobean Revival style.The original mansion remains at the heart of the property, surrounded by broad lawns and buildings added during its later evolution into an educational campus. Much of the character of the original country house remains, including handsome woodwork, substantial fireplaces, gracious rooms, and a beautiful ballroom. Most recently used for classrooms and administrative functions, the mansion was originally designed as a residence, with bedrooms on its upper floors.Beyond the main house are two dormitory residences with approximately 24 bedrooms and shared common spaces, a separate multi-level building with commercial kitchen and dining facilities, classrooms, offices, library, conference and infirmary spaces, a substantial gymnasium, and additional support buildings. For a residential buyer, this unusual collection offers possibilities for guest and staff accommodations, studios, offices, recreation, wellness, or a multi-generational Berkshire estate, subject to applicable approvals.The gymnasium could accommodate fitness, indoor tennis, pickleball, squash, or other private amenities. Existing infrastructure includes public water, multiple electrical services, mixed heating systems, central air in the dormitories and gymnasium, commercial sprinklering in select buildings, extensive parking, and established internal circulation.Hillcrest currently operates on the campus under a lease through June 2027 and presently anticipates vacating in February/March 2027.This offering is for 349 Old Stockbridge Road only. The property is also marketed as part of a combined offering with 40 Frothingham Crossing; see MLS #73518284.For its next steward, Overlee offers the rare chance to inherit not simply a house, but an entire Berkshire estate—historic architecture, expansive grounds, and a collection of buildings ready to support a new vision.Offered at $2,295,000.

This home has been viewed 4 times

Last Checked: September 15th, 2026 at 2:18pm (Source: MLS PIN #73567764)

Air Conditioning

Waterview

Lead Paint Free

General Information for 349 Old Stockbridge Rd, Lenox MA 01240

Listing ID73567764

Property TypeSingle Family / Detached

Price$2,295,000 ($59.74/SqFt)

StyleColonial

CityLenox

CountyBerkshire

Neighborhood(s)

Garage Parking0

ZoningR1A

Year Built1903

Year Built SourceAppraiser

Year Built DetailsActual

Interior Features for 349 Old Stockbridge Rd, Lenox MA 01240

Approximate Living Area Total38415

Living Area Includes BasementNo

Rooms99

Bedrooms31

Primary En Suite BathroomYes

BasementFull

Cooling1, Split

Fireplaces

AppliancesRange

FlooringTile

Electric220 Volts

Exterior Features for 349 Old Stockbridge Rd, Lenox MA 01240

Approximate Lot Size (Acres)11.9

Approximate Lot Size (Square Feet)518364

Total Parking99

Garage Parking0

WaterPublic

SewerPrivate Sewer

Lot FeaturesGentle Sloping

Parking Features1

Exterior FeaturesPorch

Foundation Materials

Construction MaterialsFrame

Road Frontage Type

Patio & PorchCovered

Roof MaterialAsphalt/fiberglass Shingles

Utility Connections

Water ViewsNo

Water Views Features

Waterfront0

Waterfront Features

Pool FeaturesAssociation

Horse Permitted0

Horse Amenities

Disclosures for 349 Old Stockbridge Rd, Lenox MA 01240

Lead PaintNone

UFFI

Living Area Includes BasementNo

Living Area Disclosure

Building Area SourcePublic Records

Special Listing Conditions

ExclusionsWasher

Title 5A

Compensation Based On

Financial Information for 349 Old Stockbridge Rd, Lenox MA 01240

Association Fee

Association Fee Frequency

Association Fee Includes

Real Estate Tax88477

Tax Year2026

Assessed Value$3,150,700

Location Information for 349 Old Stockbridge Rd, Lenox MA 01240

Elementary SchoolMorris

Middle SchoolLenox Memorial

High SchoolLenox Memorial

Neighborhood(s)

Area Amenities

Contact Information for 349 Old Stockbridge Rd, Lenox MA 01240

Agent

Name: Selina Lamb

Office

Name: Birch Properties

Phone: 413-613-4363

Payment Calculator

, Interest

Property Taxes 7373.08

Principal & Interest 14141.06

HOA Dues

Term

Interest

Home Price

Down Payment

Exclusive Listing Agent

Birch Properties

Selina Lamb

Agent Phone

Office Phone

(413) 613-4363

Text Agent Call Agent Call Office

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EXIT

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