These are the five highest-priced home sales reported in Litchfield Hills, Connecticut for the week ending October 25, 2026, and together they came to $6.5 million. All five are single-family homes in Litchfield County, spread across Litchfield, Morris and New Milford.
The group runs from a country estate with pastures and a converted barn to a pair of lake places in Morris, one a cabin-style home with its own dock and the other a 1920 cottage in a shared waterfront community. Two New Milford Colonials from the late 1980s and mid-1990s fill out the middle of the list. W. Raveis Lifestyles Realty listed three of the five homes, and in two of the sales the same agent was on both sides.
No. 1 — $3,400,000 · 287 Prospect Mountain Road, Litchfield, Connecticut
Known as Arcadia, the property at 287 Prospect Mountain Road in Litchfield sold for $3,400,000, the top price of the week. Its 19.60 acres, the largest parcel in this Top 5, are bordered by protected land: the Litchfield Land Trust’s Prospect Mountain Preserve and private holdings of the Marshepaug Club surround it. The owners also bought three acres across the street to keep the setting rural, and that parcel is counted in the acreage and protected as well. The land is cleared and rolling, with pastures, meadows, gardens and fruit trees.
The main home is a clapboard Colonial built in 2010, the newest of the five, and at 5,861 square feet it is also the largest. It has five bedrooms, each with its own bath, and six bathrooms in all, five full and one half. A Vermont slate roof tops the home, and inside there are antique beams, wide-plank oak floors and two fireplaces. The kitchen is built around a Lacanche range, and a wellness area pairs a sauna with space for a gym. The full basement is heated, cooled and finished as living space, and the home is wired for an integrated smart-home system that runs security, lighting, climate and irrigation.
The barn is the other half of the story. It has been restored and reworked for entertaining, with a party room, a bar, a wine cellar and a catering scullery, along with a guest suite, a loft and a workroom. A hot tub sits inside a screened porch there. Outside are stone patios, pergolas and mahogany decking. Skiing at Mohawk Mountain is minutes away, as are the centers of Bantam and Litchfield. The property last sold for $1.65 million in 2020.
Jessica Travelstead of W. Raveis Lifestyles Realty was the listing agent, and Holly Parker of Compass Connecticut, LLC represented the buyer. The sale was the first of three listings from W. Raveis Lifestyles Realty in this week’s Top 5.
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No. 2 — $1,060,000 · 144 Island Trail, Morris, Connecticut
In the Deer Island community of Morris, 144 Island Trail sold for $1,060,000. The cabin-style Cape Cod is a waterfront home with open views across the lake. Its main living space is built around a stone fireplace, and French doors lead out to a deck overlooking the water. Below the deck is a stone terrace with an outdoor kitchen, and steps continue from there to the dock.
Built in 1949, the main home has three bedrooms, two bathrooms and 1,257 square feet, the smallest living area of the five, on a sloped lot of 8,712 square feet. A separate guest house has two bedrooms, a bath, a kitchen and a living area of its own. Deer Island residents share a tennis and pickleball court, and the villages of Bantam, Litchfield, Washington and New Preston are a short drive away. The listing invites a buyer to restore the property. It last sold for $359,000 in 2000.
Stacey Matthews of W. Raveis Lifestyles Realty was on both sides of the sale, as the listing agent and as the agent who represented the buyer. It was one of two sales in this Top 5 that Matthews handled on both sides, and the second of three W. Raveis Lifestyles Realty listings on the list.
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No. 3 — $695,000 · 20 Timber Lane, New Milford, Connecticut
At the end of a private drive in the Northville section of New Milford, 20 Timber Lane sold for $695,000, matching its asking price. The 1989 Colonial sits on 4.89 secluded acres that border open space, and the listing says the home has panoramic views, framed by large windows in the living room, the kitchen and a bedroom.
Much of the appeal is outdoors. A heated, fenced in-ground concrete pool comes with a pool house, and there are two decks for sitting out. Inside, the 2,347-square-foot home has four bedrooms and four bathrooms, three full and one half. The kitchen has been remodeled with quartzite counters, stainless steel appliances, a pantry and a breakfast bar, and the primary suite has a remodeled bath of its own. The partially finished basement has walk-out access, and there is an attached two-car garage. The historic New Milford Green is about nine minutes away by car. The property last sold for $219,500 in 1996.
Jeff Jones of Keller Williams Realty was the listing agent, and Jamie Morelli of Coldwell Banker Realty represented the buyer.
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No. 4 — $690,000 · 4 Ayrshire Drive, New Milford, Connecticut
Also in New Milford, 4 Ayrshire Drive sold for $690,000, above its $685,000 asking price. The vinyl-sided Colonial was built in 1995 and has 2,364 square feet, four bedrooms and three bathrooms, two full and one half, on a level, landscaped lot of 1.41 acres.
The family room runs from the front of the home to the back under a vaulted ceiling, with a gas fireplace and custom built-ins. Formal living and dining rooms have hardwood floors, and the kitchen has been remodeled with granite counters, a tiled backsplash and a gas range. Radiant heat warms the first floor. Upstairs, the primary suite has built-ins, a walk-in closet and a full bath. Outside are an above-ground pool, a large custom deck, fruit trees, a garden, a storage shed and a circular driveway, and the home has solar panels and a whole-house generator. The property last sold for $207,900 in 1995.
Joe Chemero of Coldwell Banker Realty was the listing agent, and Lori J. Campbell, also of Coldwell Banker Realty, represented the buyer.
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No. 5 — $657,500 · 420 Bantam Lake Road, Morris, Connecticut
The oldest home in this Top 5, the 1920 cottage at 420 Bantam Lake Road in Morris sold for $657,500. It is part of Breezy Knoll, a lakefront association on Bantam Lake where the homes reach the water across flat ground with no road in between. Owners share about 10 acres of waterfront grounds with a sandy beach, docks for swimming and boats, a red clay tennis court and a playground. The community has two private parking areas, and the cottage is a walk of about 250 feet across flat lawn from the parking lot.
The clapboard cottage is a seasonal home with three bedrooms, two bathrooms and 1,376 square feet on a 6,098-square-foot lot, the smallest of the five. A wraparound porch has partial views of the lake, and there is a sunroom, a renovated kitchen, a fireplace and a deck. Off the property, West Shore Seafood is across the street, and the Bantam Cinema, the Litchfield Hills Rowing Club and the trails of White Memorial are within walking distance.
Stacey Matthews of W. Raveis Lifestyles Realty was the listing agent and also represented the buyer, the second sale in this week’s Top 5 in which Matthews was on both sides. It was the third W. Raveis Lifestyles Realty listing on the list.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 25, 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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