These were the five highest-priced home sales reported across the Greater Waterbury Area, Connecticut for the week ending November 8, 2026, and together they came to $3.45 million. Middlebury accounted for two of them, at the top and bottom of the list, with one each in Watertown, Prospect and Woodbury. Three of the homes are in New Haven County and two in Litchfield County.
The mix runs from a 2011 Colonial on open land to a Cape Cod with a resort-style backyard, a Colonial dating to 1825 and the week’s only new construction, a townhouse in a planned community for buyers 55 and older.
No. 1 — $826,878 · 3 Pine Ridge #23, Middlebury, Connecticut
The week’s highest-priced sale was the home at 3 Pine Ridge #23 in Middlebury, which sold for $826,878. It has two bedrooms, the fewest among the five, along with three bathrooms and 2,290 square feet of living space. The sale record does not identify a listing agent that could be verified.
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No. 2 — $740,000 · 42 Windy Ridge Lane, Watertown, Connecticut
The setting is the first thing to know about 42 Windy Ridge Lane in Watertown. The 2.92-acre lot sits on a cul-de-sac, is level and landscaped, and borders open space, with views across preserved farmland and rolling hills that take in both the sunrise and the sunset. The Colonial was custom built in 2011 and sold for $740,000.
With four bedrooms, the home has the most of any in this week’s group, plus two full baths, a half bath and 2,715 square feet of living space. Hardwood runs across the open first floor. The kitchen has solid wood cabinets, granite counters, stainless steel appliances and a pantry, and it opens to the living room, where a gas-insert fireplace and a surround-sound speaker system are the focus. An inlaid hardwood border trims the dining room floor.
Upstairs, the bedrooms are arranged around a sitting area that looks down into a two-story foyer. The primary suite has hardwood floors, a walk-in closet and a bath with an updated tiled walk-in shower, and the fourth bedroom is set up as a home office. The family bath has a cast iron soaking tub, and the laundry room is on the second floor. The partially finished basement adds a home gym and storage and walks out to a patio, while an oversized Trex deck off the living room and kitchen faces the farmland. The attached three-car garage, with a workbench and built-in storage, leads to a mudroom and powder room, and there is an electric vehicle charging station.
The property last sold for $426,900 in 2012. This time it sold at its full asking price of $740,000. Karen M. Hosking of West View Properties, LLC was the listing agent, and David McDuff of West View Properties, LLC represented the buyer.
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No. 3 — $675,000 · 1 Overlook Court, Prospect, Connecticut
The outdoor centerpiece at 1 Overlook Court in Prospect is a heated saltwater in-ground pool, added in 2022 and set on a 1,500-square-foot pool deck. The property also has a cabana and a shed, and a new vinyl fence encloses it. The 1988 Cape Cod sits on a 0.95-acre corner lot on a quiet cul-de-sac and sold for $675,000.
At 2,762 square feet, it has the most living space of the five homes. The family room has vaulted ceilings, custom built-ins and a stone fireplace that burns wood, and sliders open from it to a large stamped concrete patio. The kitchen, with Viking appliances and a coffee bar, has a picture window above its eat-in area. Pocket doors connect the large dining room to a bar or library, and from there sliders step out to a Trex deck above the yard and pool.
The three bedrooms and two full baths are upstairs, including a primary suite whose bath was recently remodeled, and a half bath completes the count. On the lower level, a bonus room is used as an office and craft space, and the basement has been refinished. There is an attached two-car garage.
The property last sold for $367,500 in 2018. It went under contract three days after it was listed and sold for $25,100 above its asking price of $649,900. Stephanie Oliver of Dave Jones Realty, LLC was the listing agent, and Stephanie Plaza of Lamacchia Realty represented the buyer.
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No. 4 — $625,000 · 27 Middle Quarter Road, Woodbury, Connecticut
The home at 27 Middle Quarter Road in Woodbury is a clapboard Colonial built in 1825 in the Middle Quarter neighborhood. It sold for $625,000. The 1.49-acre lot is level and open, runs along a brook and includes two post-and-beam barns, and the home is about a two-minute walk from coffee shops, restaurants and Woodbury’s historic Main Street.
The home was under restoration when it was listed. The listing says the work calls for new wiring, plumbing, insulation and mechanical systems along with a new kitchen and new baths. The home has wide-board antique floors, a great room with a cathedral ceiling, and formal living and dining rooms. On the second floor, the primary suite has a vaulted ceiling with exposed beams, and two more bedrooms and a walk-up attic share the floor.
The home has three bedrooms, two full baths, a half bath and 2,042 square feet of living space, the least of the five, and parking for four in a detached barn. The Middle Quarter zoning allows a business to be run from the home and the barns to be converted into added living space. The property last sold for $320,000 in 2024.
Timothy Drakeley of Drakeley Real Estate, Inc. was the listing agent. Laura A. Hart of Houlihan Lawrence WD represented the buyer.
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No. 5 — $582,954 · North Benson Road #47, Middlebury, Connecticut
The only new construction among the five, North Benson Road #47 in Middlebury is a two-story townhouse condominium in Aberdeen Estates at Benson Woods, a planned community for adults 55 and older being developed by Newport Realty Group. The neighborhood is planned for 32 attached townhomes in 11 buildings and sits within minutes of restaurants, parks, shopping, health facilities and Interstate 84.
The plans call for three bedrooms, two full baths and a half bath in 2,206 square feet, with the primary suite on the first floor and vaulted, open living and dining areas. A second-level bonus room can be finished as an option. The home also has a full basement, a backyard patio, natural gas and an attached two-car garage.
It sold for $582,954, which was $73,054 above its asking price of $509,900. Renee Lovley of Century 21 AllPoints Realty was the listing agent, and Lysa Napoli of Showcase Realty, Inc. represented the buyer.
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