The regional real estate market spanning Massachusetts, Connecticut, and New York recorded several high-value transactions in mid-September, including a property sale exceeding $3 million in Columbia County. Data from public records shows a dynamic market with significant activity in luxury homes, commercial properties, and land parcels across Berkshire, Litchfield, and Columbia counties.
Among the dozens of sales finalized, a property in Livingston, New York, sold for $3.1 million, while a home in Sheffield, Massachusetts, changed hands for $2.3 million. These transactions highlight continued strength at the upper end of the market, complemented by steady sales across all price points.
Key Takeaways
- A property at 55 Willowbrook Road in Livingston, New York, sold for $3,100,000, marking the highest sale in the region for the period.
- In Massachusetts, a home at 771 West Road in Sheffield was the top sale at $2,300,000.
- Berkshire County, Massachusetts, saw the highest volume of transactions, with notable sales in Egremont, Lee, and Lenox.
- Commercial activity included sales to LLCs in Lee, Massachusetts, and Winchester, Connecticut, indicating ongoing business investment.
- Several nominal $1 sales were recorded in Otis and Savoy, Massachusetts, typically representing property transfers from municipal ownership.
Massachusetts Market Highlights Major Transactions
Berkshire County in Massachusetts was a hub of real estate activity, with sales recorded in nearly twenty different towns between September 15 and September 19, 2025. The transactions ranged from modest land deals to multi-million dollar residential estates.
Luxury Sales Drive Market Value
The high-end market showed significant strength. In Sheffield, a property at 771 West Road was sold by Jill Freidlander and Michael Goroff to Gregory and Cynthia Schneider for $2,300,000. This was the highest-priced transaction recorded in Massachusetts during this period.
Another major sale occurred in Egremont, where the property at 206 Hillsdale Road was sold for $1,450,000. Irwin and Laura Brenner sold the home to Kenneth Ambach and Mary Kelsh-Ambach. Lee also saw a seven-figure sale, with Devonfield Farm LLC selling 95 Devon Road to Gregory and Amy Eagan for $1,384,500.
Lenox Real Estate Activity
The town of Lenox was particularly active, with seven separate property transactions recorded. Sales included a $1,250,000 home on E Dugway Road, a $900,000 property on Dunmore Court, and several other residential sales ranging from $100,000 to $700,000, showcasing a diverse market within the town.
Notable Sales Across Berkshire County
Great Barrington also saw robust activity, led by the sale of 49 South Street for $938,250. Amy Gill and Judson Ehrbar purchased the property from the Scura-Iseyama Ft and Allya Scura. Other sales in the town included a home on Commonwealth Avenue for $500,000 and a property on Park Street for $388,000.
In Richmond, a waterfront property at 292 Shore Road sold for $689,000. Pittsfield had numerous transactions, with the highest being a home at 225 Williams Street that sold for $510,000.
Understanding Nominal Sales
The towns of Otis and Savoy each recorded property sales for just $1. These transactions, such as 23 North Street in Otis and 26 Loop Road in Savoy, are not typical market-rate sales. They often represent transfers of property from a municipality to a private owner for purposes of development, conservation, or to resolve tax issues, returning the property to the tax rolls.
Steady Market in Connecticut's Litchfield County
In Connecticut, Litchfield County reported a steady stream of property sales, primarily concentrated in the towns of Torrington, Winchester, and North Canaan. The transactions reflect a healthy mid-range market for residential homes.
Winchester Leads in Sales Volume
Winchester saw the most activity, including a significant lakefront sale. A property at 740 Lake Drive was sold by the Concetta T Scutt RET to Jill and Mark Ricci for $880,000. The town also recorded multiple commercial transactions, including the sale of 920 Main Street to Gar Don Holdings LLC for $275,000 and 267 Rockwell Street to Springwood Rlty Inv LLC for $302,500.
Transactions in Torrington and North Canaan
Torrington reported five sales, with the highest being a home at 23 Lynn Heights Road that sold for $330,000. Other sales included residential properties and a commercial unit at 839 Main Street for $150,000.
In North Canaan, a home at 43 Greene Avenue was sold by Justin and Candice Roberts to Deann Hemmerich for $412,000. Another property on Cedar Lane sold for $250,000.
These sales figures, based on public records, provide a snapshot of market health, indicating strong buyer interest in both primary residences and investment properties across the Litchfield County area.
New York's Columbia County Posts Top Regional Sale
Columbia County, New York, recorded the single most expensive transaction in the tri-state region for the period reviewed. The data, covering late August and early September, shows a market characterized by high-value rural and residential properties.
Livingston Property Sells for $3.1 Million
The standout sale was at 55 Willowbrook Road in Livingston, where Kenneth Sheffer Jr and Kenneth Sheffer sold a property to 55 Willowbrook LLC for an impressive $3,100,000. This transaction underscores the continued demand for premium properties in the Hudson Valley area.
Other Significant New York Sales
Several other sales in Columbia County surpassed the half-million-dollar mark, demonstrating a consistently strong upper market.
- Kinderhook: A property at 2548 Route 203 sold for $765,000, and another at 118 Blossom Lane sold for $700,000.
- Canaan: A home at 70 Reardon York was purchased by Robert L. Larocca for $715,000.
- Hudson: A Renover LLC sold the property at 225 Robinson Street to Ryan and Jessica Naylor for $685,000.
- Ghent: The property at 106 Konig Road was sold to Faisal A. Saud and Eric Prejean for $684,000.
These transactions collectively illustrate a vibrant and valuable real estate market in Columbia County, attracting significant investment into both homes and land.
