• 18 Big Island Island, Otis, MA
• 3 Bedroom
• A-Frame, Cape
• 0.45 Acre(s)

Escape to your own island retreat where each day is a peaceful, waterfront sojourn. Nestled on an island in Big Pond, this tranquil waterfront ...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 »

• 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 »

• 2407 County Road 7 Rd, Copake, NY
• 3 Bedroom
• Contemporary, Chalet, Ranch
• 2.55 Acre(s)

Upper Rhoda Pond waterfront in Copake, New York (southern Columbia County) is a very special place. About 2 hours from NYC, it is a private 78 acre ...more »

• 39 Cascade St, Pittsfield, MA
• 4 Bedroom
• Colonial
• 2.33 Acre(s)

Beautiful early 1900's colonial farm house with deeded agricultural and horticultural rights offering 2,104 sq ft of classic charm on a picturesque 2....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 »

• 26 & 30 Cove Ln, Hinsdale, MA
• 2 Bedroom
• Ranch
• 0.12 Acre(s)

Exceptional opportunity to enhance an already ideal waterfront home with the inclusion of the adjoining waterfront parcel, 26 Cove Lane. Offering ...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 »

• 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 »

• 130 Ridge Ave, Pittsfield, MA
• 4 Bedroom
• Cape
• 0.28 Acre(s)

Welcome to life on beautiful Pontoosuc Lake, where breathtaking sunrise views and year-round waterfront living await. This charming, move-in-ready ...more »

• 46 Pinehurst Ave, Pittsfield, MA
• 3 Bedroom
• Cape
• 0.69 Acre(s)

YOUR PRIVATE RETREAT JUST A SHORT WALK TO PONTOOSUC LAKE WITH ENDLESS POTENTIAL!!! Tucked away at the Very End of the Street this 3 Bedroom, 2 Full ...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 »

• 140 Hancock Rd, Pittsfield, MA
• 8 Bedroom
• Contemporary
• 1.10 Acre(s)

Set along the shores of beautiful Pontoosuc Lake, this extraordinary private estate captures the very best of Berkshire waterfront living. Enjoy ...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 »

• 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 »

• 39,41,43,4 Danoff Lane Ln, Otis, MA
• 9 Bedroom
• Cabin
• 2.14 Acre(s)

2.14 acres with over 200 feet of water-frontage , 4, 3 season cottages all on beautiful Big Pond. This property has a long standing, consistent, ...more »

• 354 Woodmere Rd, Becket, MA
• 5 Bedroom
• Log
• 4.89 Acre(s)

A private Berkshire lodge with room for everyone.Set on 4.89 acres in Becket Woods, this five-bedroom, four-bath home offers more than 4,000 square ...more »

• Great Barrington, MA
• 6 Bedroom
• Contemporary, Shingle Style, Cottage
• 16.76 Acre(s)

The thoughtfully renovated and expanded 1940s Main House is full of exceptional spaces--elegant formal dining and living rooms in front, informal ...more »

• 35 South Ext Rd, Peru, MA
• 2 Bedroom
• Cape, Log
• 2.00 Acre(s)

Discover this Gorgeous home, constructed in 2007, presenting modern interior details and a Beautiful log exterior. This attractive property offers a ...more »

• 233 Gentian Hollow, Becket, MA
• 3 Bedroom
• Contemporary
• 2.01 Acre(s)

Bring your vision and make this Berkshire property your own! This property offers a unique renovation opportunity with plenty of space and potential ...more »

• 859 Moberg Rd, Becket, MA
• 3 Bedroom
• Cabin, Raised Ranch, Log
• 2.18 Acre(s)

Fabulous Indian Lakes Property.; Only about 8 homes down from the Lake. Fireplace for cozy nights. This 3 Bedroom 2 bath home has been completely ...more »

• 11 Maple St, Chester, MA
• 3 Bedroom
• NE Farmhouse
• 0.36 Acre(s)

OPEN HOUSE SCHEDULED FOR TODAY HAS BEEN CANCELLED. 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 »

• 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 »

• 2044 State Rd, Richmond, MA
• 3 Bedroom
• Ranch
• 22.00 Acre(s)

With 22+ acres of residential/agricultural zoned land, open fields, wooded borders, and a lovely little pond, the simplistic, quiet, natural beauty of...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 »

• 263 Shore Rd, Richmond, MA
• 1 Bedroom
• Cottage
• 0.18 Acre(s)

A charming year round cottage just steps from the private community beach. This irresistible one bedroom and one bathroom cottage delivers the best of...more »