A recent off-market sale in Sharon, Connecticut, illustrates the growing trend of private luxury real estate transactions in Litchfield County. The property at 338 Calkinstown Road, a custom-built Federal Georgian estate on 35 acres, sold for $5,750,000 without ever being publicly listed. Bill Melnick and Elyse Harney Morris of Elyse Harney Real Estate represented the transaction, approaching the seller on behalf of a buyer whose needs could not be met by current market listings.
“We knew what the buyer needed, and it simply was not available,” Melnick said. “So we approached the seller directly and asked if they were open to a private sale. They were, and from there it came together.”
For buyers and sellers operating above $3 million in markets like Litchfield County, a private sale is often the preferred outcome. Sellers avoid the disruption of showings, open houses, and public price history. Buyers avoid the anxiety of competing offers and the risk of losing a property they have committed to emotionally. Both sides get a cleaner, more controlled process.
The Calkinstown Road property had originally been sold in March 2020, at the beginning of the pandemic, before COVID pricing had taken hold. The sellers entered that transaction without the benefit of what was about to become a 30 percent run-up in county values. When approached about selling again, they were well positioned to capitalize on the appreciation.
“Sellers who agree to a private sale want to know it is worth their while,” Melnick said. “The price has to be fair, the process has to be easy, and they need confidence that the buyer is serious. When all of that lines up, it can actually be a better outcome than going to market.”
The house itself is the kind of property that sells the moment the right buyer sees it. Built in 2019 and designed in a traditional Federal Georgian style, it reads as historic without the maintenance burden of an actual historic home. Robert Fish, a local builder known throughout the county for quality and authenticity, constructed it with hand-carved fireplace mantles, antique wood library paneling, a slate roof, and copper gutters. The 6,280-square-foot home across three floors includes five en-suite bedrooms, a chef’s kitchen opening to a great room, and five wood-burning fireplaces. The 35-acre setting features a heated gunite pool and bluestone patio, stone walls, and professional landscaping, along with a detached garage alongside an attached four-car garage.
“Rob Fish’s houses are traditional in styling and very high quality,” Melnick said. “They tend to sit on exceptional building sites with big views or conservation land. When one comes available, it does not stay that way for long.”
Litchfield County is in an unusual moment. Transaction volume has moderated from its pandemic peak, but dollar volume is holding or increasing, driven by movement at the top of the market. Cash buyers, many from the finance and technology sectors in New York City, are active in the $3 million and above tier, making mortgage rate headlines largely irrelevant to how this segment moves.
Off-market activity tends to increase when inventory is thin and buyers are serious. Both conditions are present in Sharon and surrounding towns. Agents with deep community relationships and an existing base of buyer clients are facilitating these transactions, built on trust and local knowledge rather than MLS access.
For sellers considering a move but reluctant to go through a full public listing, the current environment may offer an opportunity. The right buyer may already exist in someone’s network, and the transaction may be simpler, faster, and more private than anticipated.
