The five highest-priced home sales reported in Litchfield Hills, Connecticut for the week ending November 1, 2026 added up to $3.928 million, with prices running from $850,000 in Winsted to $715,000 in Lakeville.
The sales were spread across Winsted, New Milford, New Hartford and Lakeville, where two homes sold for a combined $1,543,000. In two of the five sales, the same agent was on both sides of the deal.
No. 1 — $850,000 · 359 Winchester Road, Winsted, Connecticut
The top sale of the week was a Colonial in Winsted that sold for $850,000, its full asking price. Built in 2000, the home stands on 7.55 secluded acres with meadows, a stone wall, a barn and a two-stall run-in shed with a tack room. A screened porch off the dining room looks out toward Highland Lake in the distance.
Inside, a two-story foyer leads to an open main level, where a fieldstone fireplace rising from floor to ceiling joins the living and dining rooms. The renovated kitchen has white birch cabinets, soapstone counters, a stone subway tile backsplash, a farmhouse sink and a Sub-Zero refrigerator. A laundry room, a mudroom and a home office are also on the main level.
Over the garage, reached by a second staircase off the kitchen, is a 27-by-21-foot family room finished in 2017, with its own heating and cooling, surround sound and hookups for live music. Upstairs are three bedrooms, including a primary suite with its own bath. The home has 2,943 square feet, three bathrooms and a two-car garage. The property last sold for $653,500 in 2021.
Catherine A. McCahill of William Pitt Sotheby’s Int’l was the listing agent, and Bob B. Ficks of Berkshire Hathaway NE Prop. represented the buyer.
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No. 2 — $828,000 · 106 Indian Mountain Road, Lakeville, Connecticut
The views from 106 Indian Mountain Road in Lakeville face west, across the street toward a protected farm of more than 450 acres with limewashed barns, and they take in the sunset. The property covers 24.10 acres in two parcels and is close to Lakeville village and area schools.
The center-hall Colonial was built in 1940 and has hardwood floors and four bedrooms, one of them with its own bath in finished space above the garage. The home has 3,800 square feet, three full baths and a half bath, and an attached two-car garage. The listing presents it as a home ready for restoration. The property last sold for $140,000 in 1977, 49 years before this sale.
The home sold for $828,000 after going under contract one day after it was listed. William J. Melnick and Elyse Harney Morris, both of Elyse Harney Real Estate, were the listing agents, and Morris also represented the buyer, so the same agent was on both sides of the sale.
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No. 3 — $795,000 · 5 Anthonys Lane, New Milford, Connecticut
The newest home among the five, a Colonial built in 2022 on Anthonys Lane in New Milford, sold for $795,000. It sits on a level 1.76-acre lot on a cul-de-sac.
Past a two-story foyer, the main floor is open, with nine-foot ceilings and hardwood floors. The kitchen has Shaker cabinets, quartzite counters, a 36-inch gas range and an island measuring 81 by 50 inches, and it opens to a family room with custom built-ins and a gas fireplace framed in marble. There is also a wet bar with beverage refrigerators, and a mudroom with a built-in bench leads to the two-car garage.
Upstairs, the primary suite includes a 10-by-9-foot home office, a walk-in closet and a bath with a five-by-five-foot rain shower and two sinks. The laundry room is on that floor as well. In all, the home has four bedrooms, two full baths and a half bath in 2,760 square feet. Outside are granite walkways, a granite patio and copper gutters. The property last sold for $739,000 in 2024.
Christopher Haggerty of Compass Connecticut, LLC was the listing agent, and Andy Sachs, also of Compass Connecticut, LLC, represented the buyer.
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No. 4 — $740,000 · 720 Town Hill Road, New Hartford, Connecticut
The oldest home in the group dates to 1801. The clapboard Colonial on Town Hill Road, in the Town Hill section of New Hartford, sold for $740,000, and it has the most living space of the five, at 3,826 square feet, as well as the most land, at 31 acres.
The listing describes a renovation that reached from the foundation to the roofline. The formal living room and the formal dining room each have a fireplace, out of three in the home, and there is a screened porch. A new kitchen with granite counters and a walk-in pantry is next to a breakfast room, and a back staircase rises from the first floor. Upstairs are five bedrooms with high ceilings and new baths, along with a room that could serve as an au pair suite or a home office. The home has three full baths and a half bath.
Outside are an in-ground gunite pool with a spa, a stream and a pond. The detached two-car garage includes a recreation room, a workshop and a potting room. A separate detached building has two apartments and a studio. The property is near Route 8 and Bradley International Airport.
Laurel Galloway and Pierre Moran, both of William Pitt Sotheby’s Int’l, were the listing agents, and Kathryn C. Bassett, also of William Pitt Sotheby’s Int’l, represented the buyer. William Pitt Sotheby’s Int’l also listed the week’s top sale, in Winsted.
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No. 5 — $715,000 · 33 Wells Hill Road, Lakeville, Connecticut
In a neighborhood at the edge of Lakeville village, a 1945 Ranch at 33 Wells Hill Road sold for $715,000. Salisbury and Sharon, along with Millerton, New York, are within easy reach.
The home, with a clapboard and brick exterior, has two bedrooms, two full baths and 1,931 square feet on a level 1.06-acre lot. The living room has a wood-burning fireplace and connects to a formal dining room. A heated sunporch is used year-round, and there is also an outdoor terrace for summer. A den works as an office, library or media room, and the primary suite has a door to the backyard. The attached one-car garage leads directly into the kitchen. The property last sold for $200,000 in 1999.
Liza C. Reiss and Holly Leibrock, both of Elyse Harney Real Estate, were the listing agents, and Reiss also represented the buyer, putting the same agent on both sides of the sale. Elyse Harney Real Estate also listed the week’s No. 2 sale, on Indian Mountain Road in Lakeville.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, November 1, 2026. The report may exclude private, off-market, delayed or nondisclosed transactions. Prices, property details and professional representation are reported as available at publication and may be updated following confirmation from transaction participants.
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