Many homebuyers seek out the Berkshires and Columbia County in order to find the perfect property to enjoy with their loved ones – but sometimes, a little distance makes the heart grow fonder. Stone House Properties has listed many homes with expansive acreage, square footage, or separate quarters for your guests to spread out and enjoy. We’ve rounded up a few of our favorite exclusive listings across the Massachusetts and New York border for you and your loved ones to cherish for years to come.
520 Ridge Road, Stuyvesant NY
With 481 acres to explore and a 9,565 sq.ft. home, 520 Ridge Road has lots to offer for those seeking both outdoor and indoor recreation. Besides the ample field, trails, and ponds, the property also features a custom media room for movie nights, a spa/hot tub room, a gym and a 2,400 sq. ft. heated garage with finished game room above. The 5 bedrooms and finished walk-out basement lets loved ones spread out with a variety of activities, and come together comfortably for quality time.
Listing Price: $3,850,000
Listing Agent: Tyler Bervy
Learn more about 520 Ridge Rd here.
140 Hancock Rd, Pittsfield MA
This extraordinary home sits just steps away from Pontoosuc Lake: “Designed for both grand entertaining and multi-generational living, the gated estate includes three well-separated additional living quarters, each featuring a living room, and private entrance. This unique layout offers privacy and independence while maintaining the cohesion of a single retreat,” says listing agent Elisha Poirier.
Despite the separate living quarters, you and your guests have plenty to come together and enjoy: the property has a private dock on the lake as well as an in-ground pool overlooking the water, a spacious game room and loft, and a chef's kitchen equipped with high-end Wolf and SubZero appliances at the heart of the home.
Listing Price: $3,800,000
Listing Agents: Elisha Poirier and Randy Thunfors
Learn more about 140 Hancock Rd here.
311 Co Rd 13 Rd, Old Chatham NY
This classic Colonial rests on an exceptional 101-acre landscape with a 2.5 acre swimmable pond, a stone patio with an outdoor fireplace, and even a basketball court and playground for all ages to enjoy. “For the equestrians at heart, the property is thoughtfully equipped with a 12-stall stable, heated tack room, paddocks, and outdoor riding facilities, offering everything needed for both recreational and more serious riding,” adds listing agent Nikki Carchedi.
Inside, the seven bedrooms and 5,000+ sq. ft. of living space offers generous space to gather and unwind with family and friends. There is even a detached office for additional flexibility and privacy, ideal for those who enjoy hosting even while working from home.
Listing Price: $2,895,000
Listing Agent: Nikki Carchedi
Learn more about 311 Co Rd 13 Rd, Old Chatham, NY here.
39 Pine Crest Cross Rd, Egremont MA
Set in one of Egremont's most coveted locations, this home seamlessly integrates sophisticated contemporary architecture with carefully preserved elements of the original 1940s cottage. “The gracious primary suite occupies its own private wing, offering a tranquil retreat with complete separation from the ensuite guest suite on the opposite end of the home,” says listing agent Sheila Thunfors. 39 Pine Crest Cross even has a private office with its own exterior entrance.
From this property, you and your guests can enjoy beautifully curated gardens, an outdoor shower, and plenty of warmth and character inside.
Listing Price: $2,400,000
Listing Agent: Sheila Thunfors
Learn more about 39 Pine Crest Cross Rd here.
176 West Center Rd, West Stockbridge MA
This gorgeous 21-acre estate enjoys views of Tom Ball Mountain and is just a short jaunt to Berkshire staples like No. Six Depot, The Foundry performing arts, and Tanglewood. Beside the 3-4 bed, 2.5 bath main house is an impressive architect-designed guest house, boasting 2 ensuite bedrooms with balconies, dramatic exposed beams, and vaulted ceilings. This property is serene, private, and inviting to family and friends in every season.
Listing Price: $1,895,000
Listing Agents: Randy Thunfors and Susan Calkins
Learn more about 176 West Center Rd here.
1 and 5 Park Ave, Dalton MA
1 and 5 Park Ave is a rare, distinguished Berkshire estate with two residences on six private acres. “The stately main home at 1 Park Avenue showcases exceptional craftsmanship, a grand foyer with sweeping staircase, expansive kitchen with butler's pantry, formal living spaces, sun porch, and multiple covered porches,” writes listing agent Elisha Poirier. “The charming carriage house at 5 Park Avenue features 4 bedrooms and flexible accommodations for guests, extended family, caretakers, home office, or income potential.”
Also on the property is a detached two-car garage, fenced yard areas and mature landscaping to enjoy.
Listing Price: $1,795,000 by
Listing Agents: Elisha Poirier and Sheila Thunfors
Learn more about 1 and 5 Park Ave here.
201 Chanterwood Rd, Lee MA
The panoramic views of 201 Chanterwood Rd will stun guests in every season. While the next owner of this home can enjoy the ease of one-level living from a first-floor primary suite, the additional bedrooms and living areas across the 3 finished levels allow plenty of room for guests. “A 4th oversized garage below the house is the perfect place for all of your toys,” listing agent Susan Calkins adds.
Listing Price: $1,250,000
Listing Agent: Susan Calkins
Learn more about 201 Chanterwood Rd here.
21 Stone House Rd, Canaan NY
This 2,935 sq.ft. home was built with luxury, privacy and entertainment in mind. “The spacious first-floor primary suite provides a peaceful retreat, complete with large windows that frame the stunning surroundings, and a freshly updated en-suite bath,” writes listing agent Melissa DiMassimo. Above on the second floor is an additional bedroom, bath, and landing with access to a guest suite situated over the garage. The guest quarters are complete with a kitchenette, bedroom, living area, and bathroom with its own exterior entrance. Together, you and your guests can enjoy breathtaking views by the in-ground pool, cozying up by the fireplace, or cooking in the large eat-in kitchen that is open to the dining area.
Listing Price: $1,137,500
Listing Agent: Melissa DiMassimo
Learn more about 21 Stone House Rd here.
178 US-20, New Lebanon, NY
Ready to enjoy life on the MA-NY border? This property's 17 private acres border the 11,000-acre Pittsfield State Forest, and offers sweeping mountain views. The home was constructed in 2001, with a light-filled open floor plan centered around a fireplace. “Three ensuite bedrooms and a spacious extra room provide flexibility for guests, work, or recreation,” writes listing agent Allison Rada.
Listing price: $1,100,000
Listing agent: Allison Rada
Learn more about 178 US-20 here.
6 Manitauk Heights, Stockbridge MA
This beautiful four-bedroom, three-and-a-half-bathroom home is just 2 miles from the center of charming Stockbridge. Gather comfortably with your guests from the full-length deck, bright sunroom, or the open-floor living room/dining area/kitchen. While you enjoy the spacious primary with multiple closets and a large ensuite bath, your guests will love additional space provided by the walkout lower level, including a second kitchen.
Listing Price: $1,060,200
Listing Agent: Patricia Andrew
Learn more about 6 Manitauk Heights here.
65 Johnny Cake Hill Rd, Petersburgh NY
This idyllic country escape features post-and-beam construction, expansive windows, and 30-foot ceilings. The first-floor primary features an en-suite with a whirlpool tub, and private deck overlooking the back yard. Listing agent Melissa DiMassimo writes that “This home also offers a private, spacious first floor in-law suite with whirlpool tub, plenty of closet space, and sliders leading out to the pool, ideal for extended family or guests.” The primary and guest spaces meet at the den, “AKA the wine room,” for intimate gatherings.
Melissa adds, “There's also a fully finished basement with sliders leading to the hot tub, which provides additional living space for recreation, work, or relaxation. Additionally, there's a loft overlooking the living room that is perfect for a studio, play room, or overflow guest space and has an amazing view of the distant mountains. This home is perfect for entertaining, designed for both comfort and versatility, and privacy, it truly has it all!”
Listing Price: $774,000
Listing Agent: Melissa DiMassimo
Learn more about 65 Johnny Cake Hill Rd here.
709 New Concord Rd, East Chatham NY
This low-maintenance country retreat invites you and your guests to spend your summers by the pool! The 2 bedrooms consist of the primary, a quiet suite with a full bath and washer/dryer and its own entrance to the screened-in porch. The guest suite has its own entry off the driveway and a full bath. Enjoy the sounds of nearby Frisbee Creek, and the ease of access to nearby attractions like Tanglewood.
Listing Price: $560,000
Listing Agent: Melissa DiMassimo
Learn more about 709 New Concord Rd here.
19 Lovers Ln, New Lebanon NY
This large home was once a 2-family! As a result, you’re free to enjoy 2 kitchens, 2 living rooms, and 2 dining rooms. You and your guests can enjoy the great outdoors from the property’s multiple porches, 3.5 acres of grounds, and the Corkscrew Rail Trail located just across the street. 19 Lovers Lane is very close to all the restaurants, brew pubs, and stores in town including the wonderful year-round farmer's market store, as well as Jiminy Peak and other attractions in nearby Berkshire County.
Listing Price: $540,000
Listing Agent: Melissa DiMassimo
Learn more about 19 Lovers Ln here.
