Berkshire County, MA Real Estate Search

Berkshire County, MA 5 Bedroom Homes for Sale

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Newest Berkshire County, MA 5 Bedroom 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
$269,900
5 Beds ⋅ 2 Baths ⋅ 73558023 MLS
Lovely five bedroom two bath Colonial on 5500+ sq.ft. of land.Lots of space, front porch for relaxing on beautiful summer evenings. Two bedrooms on the first floor and three bedrooms on the second floor with a deck off the bedroom and off the kitchen on the first floor. Two driveways for plenty of parking!!!Three sheds on property for storage will stay. Or not.

12 Lincoln Street, Pittsfield
$219,000
5 Beds ⋅ 2 Baths ⋅ 73552615 MLS
Welcome to this spacious 2 family home. The work has been done for you. Interior has been completely remodeled, floors, walls, bathrooms kitchen and a new roof. Don’t miss your chance to make this your new home!

54 Marietta St, North Adams
$150,000
5 Beds ⋅ 2 Baths ⋅ 73547265 MLS
Bring this charming 1800s farmhouse back to life! Offering nearly 3,000 square feet of living space, this property is packed with potential for investors, contractors, or buyers looking for their next renovation project. Previously configured with an in-law apartment, it may offer the opportunity to convert to a two-family home with the proper permits and approvals. With its generous footprint and endless possibilities, this property is ready for a complete transformation. Investors take note—once renovated, this could become a truly exceptional property with significant upside.

842 Church St, North Adams
$329,900
5 Beds ⋅ 3 Baths ⋅ 73544041 MLS
Turn-key investment opportunity! This well-maintained three-family property is a proven income producer featuring two long-term leases with the Brien Center, providing reliable rental income. Recently renovated and easy to maintain, this property offers strong cash flow with minimal upkeep and seperate utilities. Situated in a highly walkable location close to downtown amenities, shopping, dining, and services, this is an ideal addition to any investment portfolio.

25 Spring St, Adams
$320,000
5 Beds ⋅ 2 Baths ⋅ 73543785 MLS
Great Two family with some updates. Hardwood floor in dining room and bedrooms. Kitchen and bathroom with Ceramic floor. Newer Roof. Parking off street for 4 cars

89 Robbins Ave, Pittsfield
$325,000
5 Beds ⋅ 3 Baths ⋅ 73542282 MLS
Discover the perfect blend of space, versatility, and charm in this distinctive five bedroom, three bathroom home on a quiet one-way street just minutes from downtown. Rich in unique character and history, this property showcases timeless architectural details and a flexible layout to accomodate a variety of needs. A separate apartment offers excellent potential for extended family, guests, or rental income. A three-bay attached garage provides ample storage space, room for hobbies, or the opportunity to create a workshop to suit your needs. With generous living space, endless potential, and a prime location, this one-of-a-kind property is ready for it's next chapter.

58 Quincy Street, North Adams
$660,000
5 Beds ⋅ 3 Baths ⋅ 73522628 MLS
Tucked away on a serene & private lot just minutes from the sparkling waters of Otis Reservoir, this stunningly renovated 5-bedroom, 3-bath Colonial offers the perfect blend of luxury, comfort, and natural beauty. Designed for both elegant entertaining and everyday living, the heart of the home is the spectacular chef’s kitchen featuring quartz countertops, abundant cabinetry, and refined finishes throughout. The thoughtfully designed 1st flr offers a formal living room, sophisticated dining area, two spacious bedrooms, and a beautifully updated full bath — ideal for guests or flexible living arrangements. Upstairs, retreat to the luxurious primary suite complete with a private ensuite bath, along with two additional generously sized bedrooms and a third full bath. Surrounded by peaceful nature views, trails and exceptional privacy, this remarkable property is a rare opportunity to enjoy upscale living in a tranquil setting to enjoy all the beauty the Berkshires have to offer.

23 Old Blandford Road, Otis
$3,998,000
5 Beds ⋅ 6 Baths ⋅ 24142076 MLS
WHERE THE WORLD FALLS AWAY 227 acres. 227 years. At East Hill Road's summit, East Hill Farm is a fully realized estate where infrastructure, land, and possibility are complete and in place. The 1798 Thomas Shepard House-museum-quality restoration featuring 5 bedrooms, 5.5 baths, 5 fireplaces, original King's board floors, hand-blown glass windows-awaits your vision for kitchens and baths. Modern additions: radiant heat, elevator, sun-filled library, luminous sunroom overlooking formal gardens and 4-acre spring-fed pond. The 227 acres aren't just land-they're composition. Meadow unfolding to pond positioned where morning & evening light catch it. Mature forest giving way to unbroken views. Trails looping you gently home by blue hour. Stone walls, pool, tennis court, greenhouse. Magnificent 3,550sf hand-hewn barn moved here. Northern land borders State Forest; southern abuts conservation land-permanent privacy. Guest house (6,668sf): 4 residences replete with possibilities-multigenerational living, art studios, writing spaces, media rooms, yoga, creative sanctuary. Cathedral ceilings, fireplaces, soaring light. The quiet money cannot buy: depth of silence settling at dusk, Milky Way stretching clear across valley, no light pollution. Architecture, land, and sky speaking the same language. Where hosting feels like breathing, completely natural. 5 families in 227 years. You'll be 5th. 5 min to dining, 20 min to Great Barrington, 2.5 hrs to Boston/NYC. Complete and irrepla

764 E Hill Rd, New Marlborough
$3,998,000
5 Beds ⋅ 6 Baths ⋅ 73451336 MLS
East Hill Farm offers 227 acres of protected quiet, anchored by the elegant 1798 Thomas Shepard House. A private hilltop world.Main house: Georgian-Federal; 5 BR, 5.5 BA, ~5,000 SF; 5 fireplaces; unusually high ceilings, wide-board floors, antique glass, rooms that hold the light, views that connect. Graceful, welcoming.A complete estate that also can be a working-farm or equine property: barns + outbuildings, pastures, private trails + roads, 4+ acre pond, gardens + orchard, pool, pool house, greenhouse, tennis.A vast former Arabian horse barn, now guest compound, or for you to reimagine. Preserved with rigor, lived in with joy, and rooted in the land and history that defines the Berkshires. One of the most complete and intact agricultural landscapes remaining in Southern Berkshire County, has no true comparable. Read the history. Experience East Hill Farm. Reach out.

764 East Hill Road, New Marlboro
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