Our agents work with prospective buyers that are attracted to homes on the NY/MA border for a variety of reasons. They may seek second homes an easy commute away from New York City and Boston. Or they’re searching for that forever home in a quiet town that offers wide spaces and privacy. Perhaps they want to be a part of the thriving cultural scene that real estate near Hudson, NY or Lenox, MA offers proximity to.
By being licensed in both Massachusetts and New York, our team of agents make it easy to find assistance when you’re searching across state lines. There are a wide variety of towns and hamlets along the border for you to explore, but in this article, we’ll highlight just a few neighboring towns. Our team is happy to help you find that home with the perfect blend of convenience, privacy and connection to suit your individual lifestyle.
The Southern Gateway: Egremont, MA, and Hillsdale, NY
Egremont, MA Real Estate: Rural Charm Near Great Barrington
For those seeking the classic "Berkshire experience" with the shortest possible commute from NYC, southern Massachusetts towns like Great Barrington, Lenox, and Stockbridge are top choices. Egremont is situated just south of Great Barrington. This places its residents at a convenient distance from these well-known scenic downtowns and their many cultural attractions (The Mahaiwe, Tanglewood, etc.) while offering a more rural feel.
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Property Highlights: Active homes for sale in Egremont can frequently feature stunning mountain views and significant acreage.
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Outdoor Lifestyle: Residents enjoy immediate access to Prospect Lake, Marsh Pond, and a variety of scenic hiking trails.
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Local Amenities: Living in Egremont opens doors to a lifestyle that welcomes privacy and outdoor recreation without sacrificing access to amenities like nearby restaurants, fitness facilities and healthcare (Fairview Hospital in Great Barrington).
A standout for outdoor fun nearby is Catamount Mountain Resort, which straddles the line of Egremont’s New York neighbor…
Hillsdale, NY Real Estate: An Idyllic Escape
If you have ever fantasized about escaping the city for a quiet town with just one traffic light, Hillsdale is as idyllic as it gets.
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Diverse Architecture: Real estate in Hillsdale ranges from charming historic restorations to modern builds, often nestled in private settings with expansive views.
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Community Hubs: In addition to being a quick drive over into those southern Berkshire amenities, Hillsdale is rich with farm stands, pop-up markets and breweries where the community gathers.
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Recreation: Opportunities to get out into nature are plentiful with their public trails, nearby ski area, and proximity to Copake Lake.
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Hudson Valley Access: Residents are just a short drive from the city of Hudson, providing access to Hudson Hall, Columbia Memorial Health, and an Amtrak station with direct lines to Penn Station.
The Central Corridor: Canaan, NY, and Richmond, MA
Richmond, MA Real Estate: The Heart of the Berkshires
Moving further north, Richmond is about a 2-hour drive for second home owners coming out of Boston and puts all of the Berkshires at your fingertips. Richmond, like Egremont, has a rural, bucolic feel and, notably, does not have a "true" downtown of its own.
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Ultimate Privacy: The lack of a commercial center lends itself to many properties that feel private, but Richmond residents enjoy easy access to some of the Berkshires’ most vibrant downtowns. From your Richmond home, you might reach the main strips of West Stockbridge, Stockbridge, and Lenox in 10 minutes or less.
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Urban Proximity: Richmond shares a border with Pittsfield, making it easy to reach more urban amenities, from Berkshire Medical Center to some popular “Big-Box” retailers.
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Culture & Nature: Residents may be within 30 minutes of Barrington Stage, Tanglewood, and Berkshire Theatre Group’s various stages. Hiking trails, water recreation via Richmond Pond, and popular ski areas like Jiminy Peak and Bousquet offer year-round connection to nature.
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Fine art hotspots like The Clark or MASS MoCA are still about 50 minutes north of Richmond, but you’ll find an easy, scenic drive awaiting you on your day trip up to northern Berkshire County.
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Community Spotlights: Balderdash Cellars is a year-round Richmond favorite, offering live music and yoga on an expansive lawn where families often gather in the summer months.
Canaan, NY Real Estate: A Slower Pace Near Chatham
Directly across the border from Richmond is Canaan, NY, which offers a similar pace of life while keeping you close to a truly charming downtown experience in Chatham.
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Chatham’s Local Flavor: While you can enjoy your privacy and views in Canaan, nearby downtown Chatham invites you to get to know your neighbors. Visitors tick up with summer tourists, but you’ll find locals meeting each other in Chatham’s independently-owned restaurants and retail spots year-round.
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Renowned Arts: Nearby Chatham is home to the Mac-Haydn Theatre, which features popular musicals on its in-the-round stage each summer. The historic Crandell Theatre, famous for hosting the FilmColumbia festival every October, is in the center of Main Street.
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Breathtaking Views: In Canaan, you can enjoy mountain views from Home Range Winery with a glass of wine in hand and your dog by your side. Queechy Lake offers boating, fishing and more nearby. Between Beebe Hill and Bash Bish Falls alone, you’ll find no shortage of breathtaking views on your next hike.
Buy a Home near New York and Massachusetts
Are you ready to find a quiet retreat that is minutes away from both New York farm stands and Massachusetts cultural venues? Either view our current exclusive listings, or contact the area experts at Stone House Properties today to begin exploring homes on both sides of the state line.
