The five highest-priced home sales reported in the Greater Waterbury Area, Connecticut for the week ending November 1, 2026 came to a combined $4.03 million. All five were single-family homes, two in Southbury, two in Woodbury and one in Middlebury, and prices ran from $705,000 to $890,000.
The group spans three decades of building, from a mid-1990s home in Woodbury to the only new construction on the list, and lots ranging from under an acre to more than four acres.
No. 1 — $890,000 · 309 South Britain Road, Southbury, Connecticut
The highest-priced sale of the week was a home no one had yet lived in. The new Colonial at 309 South Britain Road in Southbury, built in 2026, sold for $890,000. Finished in clapboard, it stands on a wooded 3.28-acre lot with both level and sloping ground and wetlands on the property.
The home has four bedrooms, two full baths and a half bath in 3,200 square feet, with an open plan and engineered wood floors throughout. On the main level, the eat-in kitchen is built around a center island topped in quartz and has a large walk-in pantry. A propane fireplace anchors the family room, and a combined living and dining room and a den that could serve as an office complete the floor.
Upstairs, the primary suite has a walk-in closet and a bath with a soaking tub and a separate glass-enclosed shower. Three more bedrooms, another full bath and the laundry room share the second floor. Outside, granite steps climb from the parking area to a large patio and the front porch, and the home also has a deck. The lower level holds the two-car garage along with unfinished storage space.
Bob Warner of Coldwell Banker Realty was the listing agent for the week’s top sale, and Christopher Haggerty of Compass Connecticut, LLC represented the buyer.
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No. 2 — $844,760 · 29 Cambridge Court, Middlebury, Connecticut
The Contemporary at 29 Cambridge Court in Middlebury is part of Avalon Farms, a subdivision whose homes, the listing says, draw on Cotswold architecture. The home sits on a level 0.80-acre lot on a cul-de-sac, and an 18-by-30-foot mahogany deck at the back offers distant views of Avalon Farm Pond for much of the year.
Built in 2002, the home has three bedrooms, two full baths and a half bath in 2,796 square feet. The primary suite is on the first floor, with a tray ceiling, two walk-in closets and an updated bath fitted with towel warmers. Hardwood runs across the first floor, the living room rises to a cathedral ceiling, and the kitchen pairs an oversized granite island with updated Jenn Air stainless steel appliances. Laundry is on the main level as well. Upstairs, two carpeted bedrooms share a Jack and Jill bath, and the unfinished basement has a walkout. The property last sold for $515,000 in 2017.
The home went under contract 24 days after it was listed and sold for $844,760, above its asking price of $829,900. Tracy Wilson of Lamacchia Realty was the listing agent, and Cheri L. Coleman of BHGRE Gaetano Marra Homes represented the buyer.
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No. 3 — $840,000 · 8 Curtiss Meadows, Woodbury, Connecticut
Curtiss Meadows lies at the southern end of Woodbury, along the Southbury line, and the Colonial at 8 Curtiss Meadows sold for $840,000. The home is set back from the entrance to the cul-de-sac on a level 3.12-acre lot, and at 3,865 square feet it has the most living space of the five homes on this week’s list.
Built in 2007, it has four bedrooms and five baths, three full and two half, also the most in the group. The first floor combines a kitchen with granite counters and a large center island, a great room under a cathedral ceiling, formal living and dining rooms, and a den with one of the home’s two fireplaces. Upstairs, an open foyer and sitting area leads to the primary suite and three more bedrooms. A 550-square-foot recreation room adds space in the walkout lower level.
Outdoors there is a rear patio and a porch, along with a stone wall, a privacy fence and a shed, and the owners added solar panels. The three-car garage is attached. The property last sold for $550,000 in 2013.
Joyce Drakeley and Timothy Drakeley, both of Drakeley Real Estate, Inc., were the listing agents, and Lisa Briscoe of William Raveis Real Estate represented the buyer.
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No. 4 — $752,500 · 33 Pond View Drive, Southbury, Connecticut
At 4.52 acres, 33 Pond View Drive in Southbury had the largest lot of the week. The property is on a pond, with water views, its own access to the water and a dock or mooring, and the pond is used for kayaking, canoeing and swimming in summer. The home sold for $752,500, above its asking price.
The Colonial was built in 1998 and has four bedrooms, two full baths and a half bath in 2,748 square feet. Its rooms include an eat-in kitchen, an updated custom office, and a primary suite with a full bath and a walk-in closet. Part of the basement is finished and could serve as a gym, a media room or a place for recreation, and an irrigation system waters the grounds. The property last sold for $688,500 in 2023.
Katie Ruopp of BHGRE Gaetano Marra Homes was the listing agent, and Jordan Jones of Dave Jones Realty, LLC represented the buyer. BHGRE Gaetano Marra Homes listed two of the five homes in this week’s Top 5.
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No. 5 — $705,000 · 15 Saxony Lane, Woodbury, Connecticut
The oldest home on the list, built in 1995, is a center-hall Colonial with a wraparound front porch at 15 Saxony Lane in the Good Hill neighborhood of Woodbury. It sits on a 1.47-acre lot on a cul-de-sac, a few minutes from the town centers of Woodbury and Roxbury.
The home has four bedrooms, two full baths and a half bath in 3,017 square feet. From the foyer, a formal dining room and a living room that also works as a den or office open off the entry. The remodeled kitchen has granite counters, stainless steel appliances, a gas range and a large center island that opens to an eat-in area, and the family room has a wood-burning fireplace. Upstairs, the primary suite has its own fireplace, a walk-in closet and a bath with a soaking tub and a separate shower, and three more bedrooms complete the floor.
The finished lower level offers room for work or recreation, and a mudroom and laundry room off the attached two-car garage includes a half bath. An oversized shed with a storage loft stands on the grounds. The property last sold for $275,000 in 1998, 28 years before this sale.
The home sold for $705,000, above its asking price of $699,900. Stephanie Chapman of BHGRE Gaetano Marra Homes was the listing agent, giving the brokerage its second listing in this week’s Top 5, and Dawn Bucciarelli of Century 21 Bette Real Estate represented the buyer.
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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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