The five highest-priced home sales reported in the New Haven metro area for the week ending October 4, 2026, added up to $7.03 million. All five were single-family homes in New Haven County, spread across Middlebury, Madison, Cheshire and Branford, with Madison accounting for two of them.
The group runs from a Colonial built in 1930 to one finished in 2026, and from a property of nearly 15 acres to a lot of a little over 5,600 square feet. Water figures in several of the stories, from a lake cove inland to the beaches and harbors of the shoreline.
No. 1 — $1,925,000 · 397 White Deer Rock Road, Middlebury, Connecticut
The top sale of the week sits on 14.85 acres on Lake Quassapaug in Middlebury, along Big Cove, where a path leads down to the property’s own frontage on the cove. The land is wooded and landscaped, with level ground and rolling slopes, stone walls and gardens. The property at 397 White Deer Rock Road sold for $1,925,000.
The architect-designed home was built in 2008 and has three bedrooms, three bathrooms and 3,863 square feet of living space. Its living room is anchored by a fireplace built of stone taken from the property itself. The kitchen has Custom Point cabinetry and honed granite, with Wolf and Bosch appliances and a Sub-Zero refrigerator, and it opens to terraces, gardens and a conservatory. Floors are quarter-sawn white oak, and radiant heat warms the kitchen, the conservatory and the baths.
The primary suite is on the main level, with two walk-in closets and its own access to a terrace. The upper floor has a family room and a small office along with two more bedrooms. Below, a walk-out lower level adds a heated recreation space, a wine room and a gym.
Outside, the property is reached by a gated drive and has a stone outdoor fireplace and an outdoor shower. Its outbuildings include two garages, one of them heated and cooled, an equipment barn with a greenhouse, and potting and wood sheds. The property last sold for $1.7 million in 2024.
The home went under contract the same day it was listed. Peter Klemm and Maria Taylor of Klemm Real Estate Inc were the listing agents, and Taylor also represented the buyer, so the same agent was on both sides of the sale.
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No. 2 — $1,775,000 · 50 Webster Point Road, Madison, Connecticut
Built in 1930, the oldest home in this week’s group is a Colonial at 50 Webster Point Road in Madison, on a cul-de-sac in a beach neighborhood south of Route 1. Two beaches are a short distance away in one direction, and the Shoreline Greenway Trail leads off in the other. The home sold for $1,775,000.
Classic trim work runs through the rooms, with chair rails and picture-frame molding. A formal foyer leads into a bright living room with a brick gas fireplace. The kitchen is large, with granite counters, several work areas, a breakfast bar, a walk-in pantry and a six-burner gas range, and a mudroom sits nearby. On the main floor, an office and a guest room share a Jack and Jill bath, and the primary suite is upstairs. The home has three bedrooms, three bathrooms and 2,674 square feet. Downstairs, two finished rooms with heat and air conditioning share the lower level with a second gas fireplace.
The 10,018-square-foot lot borders open space. Brick paths lead through pollinator and vegetable gardens, and the private backyard has a patio and a firepit. There is also an outdoor shower room with hot and cold water, and a detached two-car garage. The property last sold for $368,000 in 1999.
The home went under contract two days after it was listed and sold for $75,000 above its $1.7 million asking price. Todd Gould of William Pitt Sotheby’s Int’l was the listing agent, and Lisa A. Sweeney of William Raveis Real Estate represented the buyer. William Pitt Sotheby’s Int’l also had the listing on the No. 4 sale this week.
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No. 3 — $1,310,659 · 15 Melrose Drive, Cheshire, Connecticut
The only new construction in the group, 15 Melrose Drive in Cheshire was built in 2026 on the last lot in the Orchard View subdivision. It is also the largest home of the five, with 4,379 square feet, and it has the most bathrooms, with three full and two half baths. Its four bedrooms tie for the most in the group. The Colonial sold for $1,310,659.
The main level was designed around an open kitchen and family room, with hardwood floors and nine-foot ceilings. The family room rises to the second floor. A study, a dining room and a separate living room fill out the first floor, and a split staircase leads up to the bedrooms. The primary suite has its own bath, a walk-in closet and a sitting room.
The home stands on 2.07 sloping acres and has an attached three-car garage and a walk-out basement that is partly finished.
The home went under contract the day it was listed and sold above its $1.3 million asking price. Dori Degennaro of William Raveis Real Estate was the listing agent, and Michael Reiman, also of William Raveis Real Estate, represented the buyer.
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No. 4 — $1,100,000 · 177 Warpas Road, Madison, Connecticut
Set well back from the road at 177 Warpas Road in Madison, this cedar-sided Colonial sits on 1.84 acres that border 185 acres of land trust property. A lighted stone column entrance marks the drive. The home sold for $1,100,000.
Much of the life of the property happens outdoors. A two-level patio includes a 630-square-foot Timbertech deck with an automatic awning, and across the lawn are an in-ground saltwater pool, a pool house and a putting green. The grounds are professionally landscaped and fully irrigated.
Inside, the family room has a stone fireplace, a cathedral ceiling and a wall of glass facing the backyard. A den with custom built-ins opens to an eat-in kitchen, and the dining area and living room also look out over the grounds. Upstairs, the primary bedroom has a tray ceiling, and a newly created attic space allows room to expand. Built in 1969, the home has four bedrooms, three bathrooms and 2,493 square feet, along with an attached two-car garage. Madison’s town green is about two miles away.
The home went under contract 26 days after it was listed and sold at its full asking price. Margaret Muir of William Pitt Sotheby’s Int’l was the listing agent, giving the firm two of the week’s top five listings, along with the No. 2 sale on Webster Point Road. Barbara Duncan of Real Broker CT, LLC represented the buyer.
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No. 5 — $920,000 · 34 Howard Avenue, Branford, Connecticut
Architect Peter Jackson designed the living spaces of 34 Howard Avenue in Branford to face Long Island Sound, and the water view shapes the home from the kitchen onward. The Contemporary home sold for $920,000. It sits on a 5,662-square-foot lot in a harbor community within walking distance of the water, and its interiors and landscaping were shaped with design input from Atelier Cho Thompson and a professional landscape designer.
The home was built in 1940 and has three bedrooms, three bathrooms and 2,077 square feet, with an open floor plan. The kitchen is set up for serious cooking, with a Thermador induction cooktop, convection oven and hood, a Bosch dishwasher and a Fisher & Paykel refrigerator behind custom cabinet panels. Each of the three bathrooms has heated floors, skylights and wall-mounted faucets, and the primary bath is built around a large stone soaking tub. A six-foot linear gas fireplace heats the living space, and a heat pump with gas backup provides the main heat. Outside are a deck, a balcony and a patio.
The property last sold for $30,000 in 1999.
Lisa Liscio and Marci Palluzzi of Century 21 AllPoints Realty were the listing agents, and John Hill of Seabury Hill REALTORS represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 4, 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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