Berkshire County, MA Real Estate Search

Berkshire County, MA 4 Bathroom Homes for Sale

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Newest Berkshire County, MA 4 Bathroom Homes for Sale

$724,900
5 Beds ⋅ 4 Baths ⋅ 73564933 MLS
Tucked away on 3.24 private wooded acres, this one-of-a-kind Contemporary offers 3,744 sq. ft. of living space across three finished levels. Soaring ceilings, exposed timber beams, hardwood floors, and dramatic center chimney create a warm yet impressive setting. The open floor plan is anchored by multiple wood-burning fireplaces, a pellet stove, and abundant natural light. Offering a total of five bedrooms and 3.5 baths, including a private in-law suite above the oversized attached two-car garage, this home provides exceptional flexibility for guests or extended living. Enjoy an owned 9.52 kW solar system, spacious decks, beautifully maintained grounds, and the privacy of a true Berkshire retreat just a short drive from everything the Berkshires and Northampton have to offer.

255 High St Hill Rd, Windsor
$1,260,000
5 Beds ⋅ 4 Baths ⋅ 73563141 MLS
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.

1574-1579 Pleasant St, Lee
$325,000
6 Beds ⋅ 4 Baths ⋅ 73557707 MLS
Don't miss this recently renovated two-family property in a desirable location close to downtown! Each spacious unit offers 3 bedrooms and 1.5 bathrooms, featuring updated kitchens and baths, beautifully refinished hardwood floors, and functional layouts. Whether you're looking to expand your investment portfolio or owner-occupy while generating rental income, this property checks all the boxes. Conveniently located near shopping, dining, schools, and local amenities, this is an excellent opportunity in a sought-after neighborhood.

34-36 Crandall St, Adams
$399,000
8 Beds ⋅ 4 Baths ⋅ 73554619 MLS
Presenting a distinguished multi-family property located at 53 Orchard St, Pittsfield, MA.. This expansive 4 unit spans 2688 square feet of living area, offering a rare opportunity for sophisticated urban living or a strategic investment. This property includes six generously proportioned bedrooms, providing ample private accommodations across its two stories. The property's substantial lot size of 4160 square feet provides a significant footprint within the urban landscape. We invite you to discover the potential and unique character of this Pittsfield address. Three Units are vacant and recently remodeled with market rents averaging about 1395.00 in the area. One Unit is rented month to month at 950.00. All units are lead certified.

53.5 Orchard St, Pittsfield
$375,000
7 Beds ⋅ 4 Baths ⋅ 73554585 MLS
Turnkey 3-unit multifamily investment in Pittsfield, just minutes from downtown. 100% occupied, generating $4,173/month ($50,076/year) in gross rent from all-current tenants. Unit mix: 98A (1BR/1BA) at $1,199/mo, 98B (2BR/1BA) at $1,324/mo, and 100 (3BR/2BA) at $1,650/mo. All three units have gas heat and hot water; owner covers snow removal, landscaping, and water & sewer. 2025 operating expenses: taxes $3,102.87, insurance $3,168, electric $365.34, water & sewer $2,265.48. Priced at just $102/SF — well below nearby comparable sales at 91 Dalton Ave ($114.50/SF) and 1 Rostone Pl ($119.50/SF). A stable, cash-flowing asset with strong relative value in a growing rental market. Buyer to do Due Diligence.

98 Lincoln St, Pittsfield
$1,650,000
4 Beds ⋅ 4 Baths ⋅ 73520634 MLS
Pre-Construction: Step into a brand-new construction home designed to bring together modern comfort, generous space, and the natural beauty of the Berkshires. The heart of the home is an expansive open kitchen, dining, and family room area made for entertaining, slow mornings, and everyday living, complete with a walk-in pantry and seamless access to the rear deck. A separate study and additional living room offer flexibility for working from home, guests, or quiet retreat space. Upstairs, the vaulted primary suite features oversized walk-in closets and a spacious bath, joined by 3 additional bedrooms, multiple full baths, and second-floor laundry. A full unfinished basement offers future expansion potential, solar-ready design, and an attached 2-car garage add modern convenience. Ideally situated in Becket, moments from hiking, lakes, skiing, local trails, and the renowned Jacob’s Pillow arts destination, with year-round access to everything the Berkshires is known for.

79-B Woodmere, Becket
$1,650,000
4 Beds ⋅ 4 Baths ⋅ 73520630 MLS
Pre-Construction: Step into a brand-new construction home designed to bring together modern comfort, generous space, and the natural beauty of the Berkshires. The heart of the home is an expansive open kitchen, dining, and family room area made for entertaining, slow mornings, and everyday living, complete with a walk-in pantry and seamless access to the rear deck. A separate study and additional living room offer flexibility for working from home, guests, or quiet retreat space. Upstairs, the vaulted primary suite features oversized walk-in closets and a spacious bath, joined by 3 additional bedrooms, multiple full baths, and second-floor laundry. A full unfinished basement offers future expansion potential, solar-ready design, and an attached 2-car garage add modern convenience. Ideally situated in Becket, moments from hiking, lakes, skiing, local trails, and the renowned Jacob’s Pillow arts destination, with year-round access to everything the Berkshires is known for.

79-A Woodmere, Becket
$624,900
4 Beds ⋅ 4 Baths ⋅ 73515295 MLS
Welcome to your private retreat in the Crystal Pond community, set on just over 2 wooded acres. This 4-bedroom, 3.5-bath home blends comfort and natural beauty in a peaceful Berkshire setting. Cathedral ceilings, skylights, and expansive windows fill the home with natural light, highlighting rich wood plank flooring throughout. The main living area features a fireplace, while a separate den includes a wood stove insert for added warmth. One second-floor bedroom offers a private loft, and two additional bedrooms feature private balconies with wooded views. Enjoy a screened-in back porch and brand new front decks, ideal for relaxing or entertaining. A two-car garage with storage above provides space for vehicles, gear, and kayaks for nearby pond access.

135 Mallard Dr, Becket
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