• 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 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 »

• 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 »

• 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 »

• 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 »

• 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 »

• 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 »

• 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 »

• 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 »

• 295 Blair Rd, Williamstown, MA
• 7 Bedroom
• Victorian
• 0.00 Acre(s)

Own a piece of Williamstown history with this beautifully preserved Greek Revival modern farmhouse, set along the Green River on just under 20 ...more »