1574-1579 Pleasant St

Taxes: $5,694 (2026)

About this home

Historic 1815 compound — 3 independent income-producing units — $154K gross revenue in 2025. 1815 Greek Revival farmhouse duplex + converted barn — an investment rental property or family compound minutes from Main Street Stockbridge. Turnkey 5-star Airbnb, 6 years running, $154K/year. On historic registry as birthplace of a U.S. Supreme Court Justice. Compact, low-maintenance parcel — all the Berkshires, none of the yard work. Original wide-beam floors, log rafters, double-sided fireplace with brick vaulted bread oven, mature gardens with bistro tables. Three addresses — 1574, 1577 & 1579 Pleasant St. Each unit fully self-contained with own entrance, kitchen, W/D, electricity meter, and heat source. 1574: 2BR/1BA downstairs.1579: 2+BR/2BA upstairs 1577: converted barn with king bed, queen futon loft, and full bath. The hard work is done; you simply take over a fully operational hospitality business. THE NUMBERS 2025 Gross Revenue: $153,702 | NOI: $136,526 | Cap Rate: 10.84% | Gross Yield: 12.20%5-yr avg NOI: $122,423. No pro forma. No projections. All actual. Revenue documented across all seasons— summer STR, fall/winter: remote professionals, insurance relocation, medical professionals. No stabilization period needed. THE LOCATION Minutes to Tanglewood, Kripalu, Stockbridge Bowl. 2.5 hrs NYC · 2 hrs Boston. Peak STR demand June–Aug; remote professionals and corporate tenants fill all three units Sept–May. Twelve months of documented revenue, no seasonal gap over 6 years. THE OPPORTUNITY Historic designation as birthplace of U.S. Supreme Court Justice Henry Billings Brown — a permanent differentiator no new build can replicate. Active STR/MTR listings, 4.88-star brand, 180+ reviews, active forward bookings, guest handbook, host handbook, and operating playbook all convey. Municipal sewer (no Title 5) · public water · FEMA Zone X · dual residential + commercial zoning · electrical updated · 4th unit potential in unfinished barn garage. Furniture, kitchenware, linens + digital marketing assets excluded; available by separate agreement. Active STR — all units occupied.

Property details

Basement

Dirt Floor

Electric

110 Volts, 220 Volts, Circuit Breakers, Individually Metered

Waterview Features

River