Living in Berkshire County, MA and Columbia County, NY means having a front-row seat to some of the most beautiful landscapes in the Northeast. While the mountains and their hiking/skiing are often big draws to the MA and NY border, there is a unique magic to living on the water. With more than 50 lakes in the Berkshires alone, plus countless hidden rivers and streams, these features define the local lifestyle. We’ve pulled some of our exclusive listings and asked our agents how best to enjoy the water from each unique property.
140 Hancock Rd: Pittsfield, MA
This extraordinary estate is a true waterfront property, just steps away from Pontoosuc Lake in Pittsfield.
“Pontoosuc Lake is one of the Berkshires’ most sought-after lake destinations because it offers the perfect balance of recreation and natural beauty,” says listing agent Elisha Poirier. “Residents enjoy boating, kayaking, paddleboarding, swimming, and fishing throughout the warmer months, while the northern-facing views provide stunning sunrises and picturesque mountain scenery year-round.”
This home boasts 7,494 square feet of total space, including an expansive deck, in-ground pool, gas fire pit, outdoor kitchen, built-in BBQ, and thoughtfully designed open floor plan that flows seamlessly toward the water–truly designed to maximize lakefront living.
“One of the most unique aspects of this property is its versatility,” Elisha adds. “In addition to the main residence, the home includes three separate living quarters, each with private entrances and living spaces, making it ideal for multi-generational living, guest accommodations, or extended stays. The property also offers garage capacity and parking for 18+ vehicles, a rare feature in the Berkshires and especially appealing for car collectors or hobbyists. Combined with the gated entry, whole-house audio system, high-end finishes, and eco-conscious design, this is truly a one-of-a-kind Berkshire legacy property.”
Currently listed at $3,800,000 by Elisha Poirier and Randy Thunfors, you can learn more about 140 Hancock Road here.
34 Queechy Shore Beach Rd: East Chatham, NY
Welcome to Peggy's Cottage, a charming log cabin near Queechy Lake. “The owner, a cellist, originally chose this Queechy Lake home for its proximity to Tanglewood and the cathedral ceilings in the family room, which served as her music room,” says listing agent Nancy Cuddihy. “She quickly grew to love the lake community's friendly neighbors, walking trails, and private beach.”
While not directly on the water, the next owner of 34 Queechy Shore Beach Road is sure to enjoy the lovely gardens and latticed entertainment deck right outside their cabin door. The home is a part of the Queechy Shores Beach Association, which provides members with access to a boat launch, a dock, a private beach, and a recreation pavilion.
Nancy adds that Residents of the association “enjoy a variety of seasonal activities” on Queechy Lake, “from boating and kayaking in the summer to cross-country skiing and ice fishing in the winter.” Queechy Lake’s proximity to the NY/MA border offers the best of both worlds within easy reach: from the home, the next buyer can drive 15 minutes to Tanglewood or the Village of Chatham, and 23 minutes to Jiminy Peak Ski Resort.
Currently listed at $529,000 by Nancy Cuddihy, you can learn more about 34 Queechy Shore Beach Rd here.
98 Loop Dr: Otis, MA
98 Loop Drive offers a rare opportunity to experience both tranquility and excitement with waterfront living. This classic cottage with a window wall and screened porch enjoys frontage on quiet Benton Pond, with more action-packed water recreation available close by.
“Owners love the peace and quiet of this location,” says listing agent Jeff Wilkinson. “This is the second-to-last home on the Lane, so there is no traffic noise. Benton Pond is a non-motorboat lake; you can swim, canoe, kayak or fish undisturbed. If you wish to use a motorboat, you have deeded rights to Big Pond and Otis Reservoir is nearby.”
On the perks of life in Otis, Jeff says: “The historic Knox Trail is nearby, as is the Knox Trail Inn and Katie's Take Out for dining. Jacob's Pillow, Tanglewood and most other Berkshire cultural attractions are an easy drive and there are several State Forests and the Appalachian Trail nearby, yet it is only 2.5 hrs to NYC and 2 hrs to Boston. You will love the low Otis tax rate.”
Currently listed at $698,500 by Jeff Wilkinson, you can learn more about 98 Loop Drive here.
311 Co Rd 13 Rd: Old Chatham, NY
This 101-acre property is aspirational for equestrian enthusiasts, ATV riders, or anyone seeking a retreat to gather loved ones together and enjoy the great outdoors.
“At its center, the kitchen and living areas are designed for connection,” says listing agent Nikki Carchedi. “The open kitchen and dining space flows easily into the main living room, where a stone fireplace anchors the room and creates a natural place to come together after a day outdoors.”
Right outside the walls of the classic Colonial, you’ll find a stone patio with an outdoor fireplace, a basketball court and playground, a 12-stall stable and detached office. The home also looks out on a beautiful 2.5 acre swimmable pond for those hot summer days.
In Nikki’s words, “The land is what truly sets the tone. Whether on horseback, on foot, or exploring by ATV, the acreage offers a sense of freedom and room to roam that's increasingly rare. Trails wind through meadow and forest, eventually leading to a private stretch of Kinderhook Creek with its own natural pebble beach, an ideal spot for quiet afternoons, summer swims, or simply taking in the setting.”
Currently listed at $2,895,000 by Nikki Carchedi, you can learn more about 311 Co Rd 13 Rd here.
11 Mahkeenac Ter: Stockbridge, MA
Life on “The Bowl” is coveted by many prospective home buyers in the Berkshires and beyond. Stockbridge Bowl offers a rare mix of both recreational and cultural attractions. On one hand, there are ample opportunities to boat, swim, kayak and more–the famous Josh Billings Runaground Triathlon even holds its paddling leg on the Bowl, a treat to watch from your own backyard each year. On the other hand, the world-renowned cultural venue Tanglewood also has frontage on Stockbridge Bowl. Tanglewood season pass holders won’t have to travel far to catch the Boston Symphony Orchestra’s latest show, or may even catch a few notes drifting across the water.
11 Mahkeenac Terrace is “perfectly positioned to capture stunning water views and an abundance of natural light throughout,” says listing agent Patricia Andrew. This cozy cottage’s next owner can enjoy evening sunsets overlooking the water from their screened-in porch. While Stockbridge Bowl does have a public beach and boat launch, the owner of 11 Mahkeenac Ter can utilize their removable dock for swimming and boating right from their own backyard.
Currently listed at $2,998,000 by Patricia Andrew, you can learn more about 11 Mahkeenac Ter here.
327 Chester Rd: Becket, MA
This 220-acre property is a dream for those seeking a private sanctuary to reconnect with nature, with extensive groomed trails for walking or horseback riding that abut the Becket State Forest.
Just outside of its freshly renovated cape-style home, 327 Chester Rd’s next buyer can enjoy views of multiple ponds right outside their window. “Walker and Spark Brooks both feed the ponds and offer good fishing,” says listing agent Jeff Wilkinson. “The town of Becket also has a beach and boat launch on beautiful Center Pond just a few minutes drive from the house.”
The impressive parcel also includes a large post & beam barn plus stone foundations from an earlier barn. Currently listed at $2,750,000 by Jeff Wilkinson, you can learn more about 327 Chester Rd here.
520 Ridge Rd: Stuyvesant, NY
This private paradise in rural Stuyvesant is full of amenities inside and out. The home itself is a whopping 9,565 sq. ft. with spacious living areas, a custom media room perfect for movie nights, a home gym, and a spa/hot tub room. Also on the 481-acre property are two accessory buildings and a 2,400 sq. ft. heated garage with a finished game room above.
Right outside the home is one of three ponds on the property, offering idyllic views. “The ponds are better suited for fishing than swimming,” says listing agent Tyler Bervy. “They have a healthy bass population, and you have canoe/kayak storage right by the water.”
With expansive fields, 7+ miles of trails, and a stream, the possibilities at 520 Ridge Rd are endless for ATV riders, hunters, or anyone who finds peace in exploring nature.
Currently listed at $3,850,000 by Tyler Bervy, you can learn more about 520 Ridge Rd here.
