DERBY, CT — Derby's most expensive homes for sale are clustered just under $600,000, and two of the top three are in the Hilltop neighborhood. The priciest listing on Zillow.com is a modern Colonial with a pool and views from its bedrooms.
No. 1 on the list is 17 General Wooster Road in the Hilltop area, listed at $598,000. Built in 2000, the 2,996-square-foot house has four bedrooms, three full bathrooms and one half bathroom on 0.57 acres, with hardwood floors and a fireplace on the main level and a deck overlooking the pool. It has been on Zillow for nine days.
Just behind it is 66 E St., an updated 1994 raised ranch on an elevated lot with views, which hit Zillow two days ago at $580,000. The 1,276-square-foot house has three bedrooms, two full bathrooms and one half bathroom, an opened-up main level, a finished lower level and several outdoor entertaining areas on a quarter-acre.
Rounding out the top three is 29 Commodore Hull Drive, a 1999 Colonial in Hilltop listed at $579,000 after a $10,900 price cut on Sept. 17. The 2,442-square-foot home has three bedrooms, two full bathrooms and one half bathroom on 0.35 acres, and a foyer with ceilings more than 11 feet high. It has been on Zillow for 82 days.
No. 4 is 63 Academy Hill Road, a 2010 house built with the same layout on each floor: three bedrooms, a full bathroom and a kitchen upstairs and downstairs. It's listed at $549,000 after a $45,000 price cut on Oct. 17, as an executor sale with no disclosures. The 2,040-square-foot house has 9-foot ceilings, a large basement and a shed on 0.46 acres. It has been on Zillow for 98 days.
Closing out the top five is 39 Sodom Lane, a 2002 ranch on a flat corner lot with one owner since it was built, listed at $474,900 after a $10,100 price cut on Oct. 22. The 1,442-square-foot house has three bedrooms and two full bathrooms and has been updated with quartz counters, new floors, new bathrooms and new appliances. It has been on Zillow for 15 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.
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