By KeyCrew Media
Families spanning three generations are purchasing 100-acre properties in northwest Connecticut, the Hudson Valley, and the Southern Berkshires, not as investments or trophy assets, but as shared living arrangements designed around privacy and proximity. According to Elyse Harney Morris, a principal broker at Elyse Harney Real Estate, this buyer profile has grown substantially since the pandemic and now accounts for some of the largest transactions in her market.
A New Motivation for Large-Acreage Purchases
Harney says the multi-generational buyer emerged in her market during the pandemic, when families began rethinking how they wanted to live together. These buyers want a single property large enough to accommodate grandparents, parents, and grandchildren while preserving individual space.
“This is a newer phenomenon for us, and it really came about since the pandemic, where I think people are making a lifestyle choice and wanting to bring grandparents, parents, and the grandkids, and to be able to have that privacy, to have land to explore, to teach your kids how to fish or raise bees,” Harney says.
The scale is significant. Harney points to two recent transactions in the Berkshires, both closed within a two-week period, each involving approximately 100 acres. One buyer came from Boston, the other from New York. Harney says these deals represent a pattern she is seeing with increasing regularity.
Why This Market Attracts Multi-Generational Buyers
The tri-state region offers large parcels with rolling hills, water features, and agricultural history in a way that markets closer to major cities cannot. Strict zoning and active land conservation protect the surrounding landscape from rapid development, a quality that matters to families planning to hold a property across decades.
Harney also points to the region’s four-season lifestyle as a draw for families creating a shared anchor. Winter skiing at Catamount, which recently invested heavily in a new lodge, additional runs, and improved snowmaking, summer hiking on the Appalachian Trail, and year-round cultural programming at venues like Tanglewood give a large property genuine utility beyond a single season.
“Those really special, unique properties that are on a lake with tremendous views, multi-generational properties, those are still pulling off strong, strong numbers,” Harney says. While the $2 million to $3 million range represents the most active segment of the broader market, multi-generational buyers are operating above that threshold with less price sensitivity.
The Value Equation at the Upper End
Harney argues that large-acreage properties in this region offer compelling value compared to alternative luxury markets. The Hamptons, Jackson Hole, and comparable destinations command higher prices for properties with less land and less privacy. The tri-state market offers 100-acre parcels within two and a half hours of New York City.
“When you compare us to the Hamptons, when you compare us to Jackson Hole, it’s a home that you can get to every week,” Harney says. She identifies the two-and-a-half-hour drive as a practical ceiling for families with children, and the Salisbury area falls within that radius from both New York and Boston.
For multi-generational buyers, accessibility functions differently than it does for weekend visitors. When a property must work for grandparents who may not travel frequently and grandchildren who need to return to school on Monday, reaching it in under three hours from a major city is a prerequisite rather than a convenience.
California buyers also represent a growing segment. Harney says they tend to seek more modern contemporary architecture, a style less common in Litchfield County but increasingly available through new construction on the New York side in the Hudson Valley. She describes one couple displaced by the California fires who are building a contemporary home in the region and plan to live there full-time.
How the Firm Serves Cross-Border Buyers
Harney’s firm operates across all three states, Connecticut, New York, and Massachusetts, a structure built by her mother, who founded Elyse Harney Real Estate and was among the first agents in the area to hold licenses in all three states. That tri-state capability matters for multi-generational buyers evaluating properties across state lines.
“We are able to not be pigeonholed into one state, several towns,” Harney says. “Ever since COVID, we are seeing more and more people who really do not care where; they’re looking for that lifestyle, that property that is going to work for their family.”
Each town in the region has a distinct character. Harney describes Salisbury, Connecticut, as a walkable community where families choose to live in town so children can reach restaurants, the lake, and tennis courts on foot. The Hudson Valley offers more acreage and a farm-to-table culture built around local agriculture. The Southern Berkshires provide cultural institutions and mountain access. For buyers who have not yet chosen a specific location, Harney recommends renting for six months before purchasing, a trial period that reveals what daily life looks like on a Tuesday, not just a weekend.
For families assembling a multi-generational purchase, the ability to compare a 100-acre parcel in the Berkshires against a comparable property in Litchfield County or the Hudson Valley with a single firm reduces the complexity of the decision. As more families who made pandemic-era lifestyle changes seek permanent arrangements rather than weekend retreats, demand for large protected parcels within commuting distance of major cities may hold steadier than the broader market correction suggests.
About The Author: Elyse Harney Morris is a principal broker at Elyse Harney Real Estate, an independent brokerage founded in 1987 and operating across Connecticut, New York, and Massachusetts. She specializes in significant country estates, historic farms, and conservation properties across the Litchfield Hills, Hudson Valley, and Southern Berkshires.
