• 542 Water St, Williamstown, MA
• 3 Bedroom
• Contemporary
• 1.23 Acre(s)

Introducing Green River Meadows, a new luxury development that prioritizes healthy, sustainable living--ideal for those seeking an eco-friendly ...more »

• 464 North St, Williamstown, MA
• 3 Bedroom
• NE Farmhouse
• 0.40 Acre(s)

Discover the perfect blend of timeless farmhouse charm and modern updates in this beautifully maintained home, ideally located just a short walk from ...more »

• 7 Swamp Rd, West Stockbridge, MA
• 4 Bedroom
• Colonial
• 0.31 Acre(s)

Don't miss this rare opportunity to own this private, meticulously maintained waterfront sanctuary. The grounds feature a charming English garden, an ...more »

• 5 Pomeroy St, West Stockbridge, MA
• 3 Bedroom
• NE Farmhouse, Other
• 0.32 Acre(s)

Welcome to 5 Pomeroy St. in the heart of charming West Stockbridge, where small-town New England character meets the beauty of the Berkshires. Ideally...more »

• 19 Lakeside Dr, Tyringham, MA
• 3 Bedroom
• Cottage
• 0.54 Acre(s)

Opportunity to complete this renovation. Extensive site work has already been completed. $25,000 of Tree removal in 2022, kerosene tank removal in ...more »

• 1111 Clubhouse Rd, Tolland, MA
• 4 Bedroom
• Log
• 2.04 Acre(s)

One of the Southern Berkshires' best-kept secrets! This private, family-friendly, four-season community is located near the shores of pristine 175-...more »

• 200 Fox Den Rd, Tolland, MA
• 3 Bedroom
• Cape
• 1.40 Acre(s)

Spend peaceful mornings surrounded by nature in a private setting that backs to protected conservation land at the foothills of the Berkshires. Set on...more »

• 1 Massasoit Rd, Stockbridge, MA
• 2 Bedroom
• Cottage
• 0.38 Acre(s)

Turnkey Berkshire Retreat Near Stockbridge Bowl & Tanglewood - Embrace effortless seasonal living in this beautifully maintained, vintage three-season...more »

• 10 Mahkeenac Shores Rd, Stockbridge, MA
• 4 Bedroom
• Contemporary
• 0.12 Acre(s)

Experience the best of Berkshire living in this stunning contemporary waterfront home on Stockbridge Bowl. Thoughtfully designed, this 4 BR, 3 full ...more »

• 7 Wheatley Dr, Stockbridge, MA
• 4 Bedroom
• Contemporary
• 6.20 Acre(s)

At the Lenox/Stockbridge town line on the shore of Lily Pond, sits this architectural gem! Offering a rare combination of privacy artfully aligned ...more »

• 2 Woods Rd, Stockbridge, MA
• 3 Bedroom
• Ranch
• 0.63 Acre(s)

A tranquil oasis in the sought after Beachwood community with its private beach and kayak launch on Stockbridge Bowl. This ranch-style cottage with ...more »

• 6 Grove Rd, Stockbridge, MA
• 4 Bedroom
• Cottage
• 0.21 Acre(s)

Brilliantly located very close to the Beachwood community private beach and kayak launch on Stockbridge Bowl is this atmospheric cottage replete with ...more »

• 10 Mahkeenac Terr, Stockbridge, MA
• 2 Bedroom
• Cape, Timber Frame, Cottage
• 0.44 Acre(s)

Bring your BOAT and enjoy all that the Stockbridge Bowl has to offer. This charming home has deeded rights to the lake, as well as its own dock space!...more »

• 10 Mahkeenac Heights Rd, Stockbridge, MA
• 2 Bedroom
• Cabin, Cottage
• 0.14 Acre(s)

Beach days, porch evenings and Tanglewood concerts make this the perfect three-season Berkshire cottage. Vaulted ceilings and a fieldstone fireplace ...more »

• 525 Andrea Dr, Stamford, VT
• 5 Bedroom
• Contemporary
• 38.46 Acre(s)

The Ultimate Vermont Mountain Sanctuary:Discover total serenity at the end of a winding gravel road. Encircled by 37 acres of pristine woods, a ...more »

• 6 Redwood Ln, Sheffield, MA
• 5 Bedroom
• Cottage
• 0.42 Acre(s)

Enjoy comfortable, move-in-ready living at this inviting Sheffield property, complete with a barn and access to a nearby pond for fishing and kayaking...more »

• 304 Hickey Hill Rd, Sheffield, MA
• 4 Bedroom
• Colonial, NE Farmhouse, Historic
• 16.49 Acre(s)

This historic farmhouse, originally built in the 1790s, underwent a complete renovation in 2012, including a new foundation, septic system, roof, ...more »

• 729 Hewins St, Sheffield, MA
• 5 Bedroom
• Contemporary
• 70.00 Acre(s)

Marcel Breuer partner Tician Papachristou designed this home as a private paradise for his three-generation family: a long driveway leads past a ...more »

• 369 Deer Run Rd, Sandisfield, MA
• 3 Bedroom
• Contemporary
• 1.00 Acre(s)

Little Acorn House - a warm and inviting Otis Wood Lands Contemporary with three bedrooms and three full bathrooms. The dappled morning light ...more »

• 307 Sanctuary Ln, Sandisfield, MA
• 4 Bedroom
• Contemporary
• 1.00 Acre(s)

Light, airy & effortlessly inviting this 4 bedroom & 3 full bath home is made for Berkshire Living. Walls of windows & a sun filled sunroom bring the ...more »

• 311 Tamarack Trail, Sandisfield, MA
• 3 Bedroom
• Contemporary
• 1.00 Acre(s)

This 1,320-square-foot contemporary retreat at 311 Tamarack Trail is refreshed and ready for immediate move-in. Tucked away in the private Otis Wood ...more »

• 19 Roberts Rd, Sandisfield, MA
• 5 Bedroom
• Timber Frame, Shingle Style
• 1484.25 Acre(s)

Introducing 
FREE QUARTER FARMNearly 1,500 Acres | Sandisfield, the Southern Berkshires | $4,500,000Miles of private trails for hiking, hunting, ...more »

• 303 Lakeshore Dr, Sandisfield, MA
• 4 Bedroom
• Contemporary
• 1.00 Acre(s)

Discover the epitome of lakeside living in this exceptional 4-bedroom, 2-bath home nestled in the desirable Otis Wood Lands community. This fully ...more »

• 132 North Main Rd, Sandisfield, MA
• 3 Bedroom
• Split Level
• 94.00 Acre(s)

Cross the charming historic-style covered bridge and enter a world of privacy, nature, and endless possibilities. This remarkable 94-acre sportsman's ...more »

• 14 Roosterville Rd, Sandisfield, MA
• 4 Bedroom
• NE Farmhouse
• 4.61 Acre(s)

At the end of a quiet dead-end road in Sandisfield, this c.1892 four-bedroom farmhouse sits less than twenty feet from the Wild and Scenic West Branch...more »

• 317 Lakeshore Dr, Sandisfield, MA
• 4 Bedroom
• Contemporary
• 1.00 Acre(s)

Otis Wood Lands lakefront Contemporary on OWL Lake with four bedrooms and three full bathrooms. Open kitchen/dining/living area with views of the ...more »

• 309 Tamarack Trail, Sandisfield, MA
• 3 Bedroom
• Contemporary
• 1.00 Acre(s)

Rustic Contemporary in Otis Wood Lands that abuts the State Forest! This cozy home has an open concept kitchen/living/dining area with vaulted ...more »

• 51 Cherry Rd, Richmond, MA
• 2 Bedroom
• Other
• 0.40 Acre(s)

The keyword for this spacious Richmond Shores 2 bedroom with extra loft sleeping space/2 bath lake property is ''new''! New roof, new hot water heater...more »