349 Old Stockbridge Rd Lenox — Photo 1 of 40
Recent Drop: $555,000
$3,195,000
Investment Analysis — 349 Old Stockbridge Rd
Lenox, MA 01240
Based on HUD Small Area Fair Market Rent for Pittsfield, MA HUD Metro FMR Area, a 34-bedroom in 01240 carries an estimated $2,600/mo in gross rent — about a -2.36% cap rate and $-75,475/yr in estimated NOI at the $3,195,000 list price. Adjust every assumption in the calculator below.
Beds
34
Baths
23.5
SqFt
40,241
Style
Single Family
Built
1903
Rare 16.76± acre contiguous institutional campus and redevelopment opportunity in Lenox, MA, in the heart of the Berkshires. Anchored by Overlee, a historic 1903 estate, the property includes multiple buildings with 32 dormitory-style bedrooms, classroom and administrative space, dining facilities, shared common areas, and a large gymnasium. Existing infrastructure includes internal roadways, parking, public water, sprinkler systems, mixed heating, and up to 600 amp electrical service. Also included is a 1,826 SF residence on 4.74± acres across three contiguous parcels offering additional flexibility. Currently operated as an educational campus, the property offers compelling long-term potential for institutional, residential, wellness, medical, hospitality, or mixed-use concepts. Buyers to conduct due diligence.
ADU Potential
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 40,241 sq ft principal dwelling). Lot size: 726,145 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Electric Water Heater • Dishwasher • Microwave • Indoor Grill • Refrigerator • Freezer • Washer • Dryer • Range Hood
Geography
Property History
$3,195,000
Was $3,750,000
Aug 25, 2026
MLS® 73518284
$2,295,000
Aug 25, 2026
MLS® 73567764
$2,295,000
Aug 25, 2026
MLS® 73567766
$3,750,000
May 13, 2026
MLS® 73518284
$3,195,000
May 13, 2026
MLS® 73518283
Listing Agent: Selina Lamb
Listing Office: Birch Properties
MLS® Number: 73518284
