The highest-priced home sales reported in the New Haven metro area for the week ending October 18, 2026, came from five different towns: New Haven, Cheshire, Madison, Middlebury and North Haven. Together the five sales totaled $6.19 million.
All five are single-family homes in New Haven County, and they span more than a century of building, from a 19th-century home in the city to one sold as new construction in the suburbs.
No. 1 — $1,800,000 · 8 Saint Ronan Terrace, New Haven, Connecticut
The week’s top sale came from New Haven’s Prospect Hill neighborhood, where 8 Saint Ronan Terrace sold for $1,800,000. The home sits on a cul-de-sac and dates to 1890, making it the oldest of the five. Its exterior pairs shingle siding with stone, and its sloped lot of 9,583 square feet is the smallest in this week’s group.
Inside are 4,345 square feet, with four bedrooms, three full baths and a half bath, and four fireplaces. Beyond the bedrooms, the home has a library and two flex rooms that could become extra bedrooms, an office, a gym or a studio. The kitchen has been renovated and is fitted with Wolf and Sub-Zero appliances. The primary suite comes with its own sunroom, a custom closet and a newly redone bath.
Parking is in a detached one-car garage, and a newly installed EV charger has been added. The home is in the Worthington Hooker Elementary district. The property last sold for $1.25 million in 2022.
Laura Roselinsky of Compass Connecticut, LLC was the listing agent, and the home sold for $205,000 above its asking price of $1.595 million. Jennifer M. D’Amato of Real Broker CT, LLC represented the buyer.
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No. 2 — $1,370,632 · 17 Melrose Drive Lot 3, Cheshire, Connecticut
The newest home in this week’s Top 5 was sold before it was built. The buyer of 17 Melrose Drive Lot 3, in Cheshire’s Orchard View subdivision, purchased a new-construction Colonial on the expanded Essex plan, set on a lot of 1.03 acres. The plans call for 4,011 square feet, four bedrooms, three full baths and two half baths, along with an attached three-car garage and a full, unfinished basement.
On the main level, the plans show nine-foot ceilings, a large kitchen and a family room with a cathedral ceiling and a propane fireplace. A mudroom off the garage includes a half bath and a walk-in pantry. The entrance foyer has an open ceiling and a split staircase, and a dining room, a guest suite and a large study complete the first floor.
The bedrooms and a laundry room are planned for the second floor. The primary bedroom has a vaulted ceiling, a large walk-in closet and its own bath, and one of the other three upstairs bedrooms also has an en-suite bath.
The home went under contract the day it was listed and sold for $1,370,632, above its asking price of $1.299 million. Dori Degennaro of William Raveis Real Estate was the listing agent; William Raveis Real Estate also listed the No. 4 sale this week, 25 Avalon Drive in Middlebury. Betsy B. Anderson of William Pitt Sotheby’s Int’l represented the buyer.
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No. 3 — $1,350,000 · 77 Hickory Lane, Madison, Connecticut
The largest lot among the five belongs to 77 Hickory Lane in Madison: 2.11 level, landscaped acres, with more than seven acres of land trust property behind the home. The grounds were professionally landscaped, and a heated in-ground pool is set amid greenery. The property also has a deck and an underground sprinkler system.
The Colonial was custom-built in 2001 for its original owners. Its 4,421 square feet, spread across the first and second floors, is the most living area of the five, and it has four bedrooms, four full baths and a half bath, and an attached three-car garage. On the main level, the family room has a vaulted ceiling and a wood-burning fireplace, and the home has two separate home offices.
Above the garage is a bonus room with its own full bath and laundry area, suited to guest quarters or an au pair suite. The basement is partially finished. The home is near Route 80, with easy access to New Haven. The property last sold for $582,000 in 2001.
Kirsten Adams of William Pitt Sotheby’s Int’l was the listing agent for the home, which went under contract nine days after it was listed and sold for $1,350,000, $100,000 over its asking price of $1.25 million. Susan Santoro, also of William Pitt Sotheby’s Int’l, represented the buyer.
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No. 4 — $865,000 · 25 Avalon Drive, Middlebury, Connecticut
Avalon Farms, the Middlebury subdivision where 25 Avalon Drive sold for $865,000, has streetlights and streets lined with Belgian block. The home stands on a flat 0.69-acre lot ringed by mature pines. Built in 2002, it has 3,494 square feet, three bedrooms, three full baths and a half bath, and an attached two-car garage. The property last sold for $765,000 in 2024.
A two-story foyer opens the interior, and the primary suite is on the first floor, with an oversized closet and its own bath. The great room has a soaring ceiling and a fireplace, and a large study has a second fireplace. The eat-in kitchen has a Bertazzoni gas cooktop and a double oven, and the main level also has the laundry and a pantry.
Upstairs are two more bedrooms and a loft that could work as an office or extra living space. Outside, a paver patio sits among established gardens with landscape lighting, and the lower level is unfinished.
Connie Widmann of William Raveis Real Estate was the listing agent, one of two sales in this week’s Top 5 listed by the firm. Bonnie Wilson of Berkshire Hathaway NE Prop. represented the buyer.
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No. 5 — $805,000 · 47 Windsor Road, North Haven, Connecticut
In North Haven’s Ridge Road neighborhood, the home at 47 Windsor Road is a 1958 ranch finished in brick and wood siding, with a circular driveway and an attached two-car garage on a level, landscaped lot of 0.57 acres. It has 2,396 square feet, two bedrooms and two baths, the smallest living area and fewest bedrooms in the group.
A sunroom with skylights, slate floors and walls of glass sits off the living room, which has a gas fireplace and custom wainscoting. A den with parquet floors has a second gas fireplace. The formal dining room leads to the kitchen, which has double ovens, and a family room off the kitchen has its own door to the backyard. The primary bedroom has built-ins, three closets including a walk-in, and a large updated bath.
The lower level has a custom wine cellar and the laundry. Outside, the fenced backyard has mature plantings, among them a cactus garden, along with a bluestone patio and a deck at ground level. An audio system serves both the inside and outside of the home. The property last sold for $580,000 in 2022.
The home went under contract one day after it was listed and sold for $805,000, $110,000 above its asking price of $695,000. Jill Nathanson-Zaengel of Press/Cuozzo Realtors listed the home with Dave Candido, also of Press/Cuozzo Realtors, and Eileen Smith of Pearce 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, October 18, 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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