NEW HAVEN, CT — The most expensive properties for sale in New Haven are apartment buildings, led by a $3.9 million building on Chapel Street. For buyers looking for a home, the five priciest single-family houses and condos on Zillow.com run from a Westville Colonial with a wraparound porch to a condo carved out of a former church on Wooster Square.
No. 1 on the list is 352 McKinley Ave., a Westville Colonial built in 1928 and listed at $995,000 after a $55,000 price cut on Oct. 16. Zillow lists 4,693 square feet, while the description says more than 3,800. It has six bedrooms, three full bathrooms and two half bathrooms on 0.39 acres, plus a wraparound porch, high ceilings, decorative fireplaces and hardwood floors. The neighborhood's cafes, farmers market and library are steps away. It has been on Zillow for 25 days.
Just behind it is 476 Norton Parkway, a 1925 house renovated top to bottom with a new roof, plumbing and electrical, listed at $850,000. Zillow lists six bedrooms, three full bathrooms and two half bathrooms in 2,541 square feet, while the description says five bedrooms plus two spaces that could become more. It also has a finished basement and attic. It has been on Zillow for 54 days.
Rounding out the top three is a house directly on the Quinnipiac River at 329 Front St., listed at $779,900. The 1,368-square-foot house has three bedrooms, two full bathrooms and one half bathroom, river views from its open living and dining areas and a shared dock. Zillow dates it to 1820, while the listing describes it as newer construction. It has been on Zillow for 107 days.
No. 4 is a condo in The Gables, a former church and parish house on Wooster Square Park: unit 9 at 329 Greene St., asking $749,000. The 1,802-square-foot unit has two bedrooms, two full bathrooms and one half bathroom. Its great room is 23 feet square and 16 feet high, with tall windows and a balconied office overlooking the space. It has been on Zillow for 14 days.
Closing out the top five is 114 Colony Road, a 1929 Tudor Colonial in Beaver Hills listed at $699,000. The 2,753-square-foot house has four bedrooms, two full bathrooms and one half bathroom, and a big kitchen with four ovens and two sinks. It has been on Zillow for 103 days.
Prices, listing status and days on market are from each property's Zillow.com listing as of Oct. 26, 2026, and may change. Only homes marked "For sale" or offered as new construction were included; pending, coming-soon, land-only and multifamily listings were left out. Multifamily buildings, including a new four-unit townhouse building on Colby Court, were left out, as were two Yale-area buildings now used as offices: 1455 Chapel St., listed at $1,895,000, and the William DeForest House at 445 Orange St., listed at $1,495,000.
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