Not every great town in the Berkshires makes the weekend guides—and that’s exactly the point. While Lenox and Great Barrington often get the spotlight, those who live here year-round or own second homes quietly know where the real magic—and value—can be found.
At Birch Properties, we spend our days in the field, and these are the places we’re most excited about right now: towns that blend beauty, character, and community without the hype. If you’re looking to buy smart this summer, start here.
Lanesborough
With Mt. Greylock rising in the distance and Lake Pontoosuc shimmering at its edge, Lanesborough offers a powerful mix of outdoor beauty and low-key living. Many locals choose it for its access to year-round recreation—hiking, skiing, paddling—all within minutes of home. It’s also just a short drive from Pittsfield’s shops, dining, and medical services, making it ideal for full-time or hybrid residents. Inventory here moves quickly, especially near the lake or tucked into the hills. For those who want space without isolation, Lanesborough delivers.
Richmond
If you're after quiet sophistication with a strong sense of privacy, Richmond belongs on your radar. Bordering both Lenox and New York State, it’s a pastoral haven filled with open fields, historic farmhouses, and just the right touch of refinement. It's where buyers often end up when they want proximity to culture—but not the foot traffic. Homes here tend to sit on larger lots, many with views, and the community skews toward long-term residents who value conservation and quiet. This is a town that doesn’t try to impress—but inevitably does.
New Marlborough
Tucked in the Southern Berkshires, New Marlborough is often overlooked—and that’s exactly why people fall in love with it. It’s home to understated elegance: white clapboard colonials, winding roads, and a deeply artistic undercurrent. The village of Southfield has become a favorite among second-home buyers looking for charm and privacy, while the rest of town boasts miles of conserved land and hidden gems. Plus, with nearby access to Great Barrington and cultural destinations like The Mount and Music & More, it’s perfectly positioned for those who want rural living with richness nearby.
What These Towns Have in Common
They’re not destinations for weekenders—they’re communities. They offer the kind of low-key Berkshire living that locals cherish: good neighbors, dark night skies, generous porches, and real connection to the land.
They also represent smart investments. These towns tend to have limited inventory, well-maintained homes, and long-term appeal. In a market that’s cooled slightly from its peak, they offer both stability and potential upside.
A Word from Selina
“We always tell our clients: the prettiest towns aren’t always the loudest. The real Berkshires are lived in quietly—by those who know where to look. And those places? That’s where the heart of this region really beats.”
Thinking of buying? Let’s take a closer look at these towns together. Whether you're planning a move now or mapping out your future, Birch Properties is here to guide you—every back road, every hidden listing, every step of the way.
