A recent off-market sale in Sharon, Connecticut, illustrates a growing trend in the luxury real estate market: high-end properties are increasingly changing hands through private transactions rather than public listings. 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, according to Elyse Harney Real Estate agents Bill Melnick and Elyse Harney Morris.
The sale underscores a market where inventory is scarce and buyers are abundant, particularly in Litchfield County, Connecticut. "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 transactions above $3 million in markets like Litchfield County, private sales often offer advantages for both parties. Sellers avoid the disruption of showings and public price history, while buyers escape bidding wars and the emotional risk of losing a property. Both sides gain a cleaner, more controlled process.
The Calkinstown Road property was originally sold in March 2020, just before the pandemic-driven run-up in county values. When approached about selling again, the sellers were well positioned to capitalize on 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 estate itself is a key factor in its quick sale. Built in 2019 by renowned builder Robert Fish, the house features hand-carved fireplace mantles, antique wood library paneling, a slate roof, and copper gutters. It spans 6,280 square feet across three floors, with five en-suite bedrooms, five wood-burning fireplaces, and a chef's kitchen opening to a great room. The 35-acre setting includes a heated gunite pool, bluestone patio, stone walls, and professional landscaping, along with a detached garage and an attached four-car garage. The property borders one of the highest-recorded sales in Litchfield County history—a $10 million adjacent parcel also built by Fish. "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 long."
This sale signals broader trends in the luxury market. While transaction volume has moderated from its pandemic peak, dollar volume is holding or increasing due to activity at the top. Cash buyers, many from finance and technology in New York City, dominate the $3 million and above tier, making mortgage rate fluctuations largely irrelevant. Off-market deals tend to increase when inventory is thin and buyers are serious—both conditions present in Sharon now. Agents with deep community relationships and a base of buyer clients facilitate these transactions, which rely on trust and local knowledge rather than MLS access.
For sellers considering a move but reluctant to go public, the current environment may be worth exploring. The right buyer may already exist in someone's network, and the transaction can be simpler, faster, and more private than anticipated.
