For years, Litchfield County in northwestern Connecticut was a well-kept secret – a place where New Yorkers retreated on Friday afternoons and left by Sunday evening. That dynamic has fundamentally shifted, and the data is hard to ignore. Prices are up roughly 30% since the pandemic. Luxury sales above $3 million, once a handful per year, now number in the dozens. And the buyers showing up today aren’t looking for a weekend escape – they’re planting roots.

Bill Melnick, a luxury real estate specialist with Elyse Harney Real Estate, has had a front-row seat to every stage of this transformation. “The secret is out,” he says flatly. “And the momentum hasn’t stopped.”

The headline story is capital migration, but the underlying engine is more nuanced than pandemic-era flight from the city. Private schools have become one of the most consistent demand drivers in the market. Hotchkiss, ranked among the top boarding schools in the country, routinely draws families who then purchase or rent nearby – often despite the fact that their children are boarding full time. Several elite private day schools in the area are pulling families directly out of New York City’s competitive prep school circuit. “Sometimes both parents move here full time and work remotely,” Melnick explains. “Sometimes one commutes – leaving at 6:30 Monday, back Thursday. It runs the gamut.”

California buyers added another layer in 2025. Wildfires pushed a wave of high-net-worth relocators eastward, with many eyeing both New York and Connecticut simultaneously. Melnick personally closed three transactions with California clients last year, most attracted by the school ecosystem and the area’s proximity to Manhattan – roughly a two-hour commuter rail ride. That specific wave has moderated in 2026, but the underlying interest from out-of-state buyers has not.

The $1.5 to $2.5 million range is currently the most active segment, driven by buyers seeking turnkey properties with views and pools – two features that consistently command significant premiums in this market. Above $2.5 million, sales are growing but more selective. Inventory at the entry level moves quickly when it appears; the challenge is that not much of it does.

At the very top of the market, Melnick’s track record is instructive. His sale of Ivan Lendl’s 400-plus-acre Cornwall estate remains the highest recorded transaction in the county – a deal that required strategic media placement, targeted outreach to brokers in other luxury markets, and direct leveraging of a high-net-worth New York City network built over a 26-year career as an Executive at Ralph Lauren. Luxury properties, he notes, require a fundamentally different marketing approach than the broader market. “It’s proactive,” he says. “You’re not waiting for the right buyer to find the listing.”

Inventory remains constrained at the entry and mid levels. Luxury is outperforming. Out-of-state buyer interest – particularly from families prioritizing education and lifestyle – continues to underpin demand. For investors and market watchers tracking capital flows out of New York, Litchfield County is no longer a footnote. It’s a market worth watching closely.

Bill Melnick is a luxury real estate specialist with Elyse Harney Real Estate, serving Litchfield County and surrounding markets in Connecticut.

Disclosure: Individuals or companies mentioned may have a commercial relationship with KeyCrew.

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