The luxury real estate market in Litchfield County, Connecticut, is running short on inventory and long on motivated buyers, pushing more high-end transactions away from public listings and toward private deals that never appear on Zillow until after they close. A recent off-market sale in Sharon, Connecticut, exemplifies this trend: 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 competing offers and the risk of losing a property they have emotionally committed to. Both sides gain a cleaner, more controlled process. The Calkinstown Road property had originally sold in March 2020, before pandemic pricing took hold. 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 house itself, built in 2019 by local builder Robert Fish, is designed in Federal Georgian style, offering historic charm without the maintenance burden of an actual historic home. Details include hand-carved fireplace mantles, antique wood library paneling, a slate roof, copper gutters, five wood-burning fireplaces, 6,280 square feet across three floors, five en-suite bedrooms, and a chef’s kitchen opening to a great room. The 35-acre setting features a heated gunite pool, bluestone patio, stone walls, and professional landscaping. A detached garage accompanies the attached four-car garage. The property borders one of the highest-recorded sales in Litchfield County history, a $10 million transaction on an 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 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 finance and technology sectors in New York City, are active in the $3 million and above tier, making mortgage rate headlines largely irrelevant. Off-market activity tends to increase when inventory is thin and buyers are serious, both conditions present in Sharon and surrounding towns. Agents with deep community relationships and existing buyer clients facilitate these transactions, built on trust and local knowledge rather than MLS access. For sellers considering a move but reluctant to go through a public listing, the current environment may warrant a conversation: the right buyer may already exist in someone’s network, and the transaction may be simpler, faster, and more private than anticipated.
