The real estate market in the Litchfield Hills, Hudson Valley, and Southern Berkshires is witnessing a notable shift: buyers who initially sought weekend retreats are increasingly choosing to make these regions their permanent homes. Elyse Harney Morris, principal broker and owner at Elyse Harney Real Estate, observes this pattern across her tri-state firm. 'They stay for a year,' she says, 'and then one of them starts commuting a few days a week, and then the whole thing just stops, and they go: we're staying.'
The regions retain buyers because they deliver across all four seasons. Winter is anchored by Catamount Mountain Resort, which recently invested in a new lodge, expanded trails, and improved snowmaking. The resort also hosts ski jumping competitions and will welcome the Junior Olympics for the second time. Summer belongs to Tanglewood in Lenox, Massachusetts, where the Boston Symphony Orchestra performs and James Taylor's concerts draw crowds. The Appalachian Trail, land trust properties, and growing electric bike trails provide year-round outdoor activities.
Cultural offerings run deep: the Yale School of Music's summer programs in Norfolk, Connecticut, are open to the public, and prep schools like Hotchkiss and Salisbury School host lectures and performances. Millbrook Winery in the Hudson Valley hosts weekend music and farm dinners that become part of the local rhythm.
Community infrastructure is crucial for retention. Town centers like Salisbury offer walkable access to restaurants and lake activities. The prep school network—Hotchkiss, Salisbury School, Berkshire School, and feeder schools—creates an educational draw for families. Farm-to-table culture, farmers markets, and food and wine events add to the local lifestyle.
Permanent buyers approach the market differently, prioritizing school systems, medical facilities, and the character of towns in winter. Morris notes that the $2 million to $3 million price point is most active, driven by buyers who have already spent time in the region. Strict zoning and land conservation ensure the region's character remains intact, which is a key factor for those making a long-term commitment.
Elyse Harney Morris is principal broker and owner at Elyse Harney Real Estate, an independent brokerage founded in 1987, operating across Connecticut, New York, and Massachusetts, specializing in country estates, historic farms, and conservation properties.
