STONINGTON, CT — A European-style estate in Stonington Borough, whose gardens have long been a highlight of the borough's garden tour, tops Stonington's most expensive homes for sale on Zillow.com. All five of the town's priciest listings are above $3.9 million, and most come with water or serious acreage.
No. 1 on the list is 40 Grand St., asking $5,950,000. The 1928 house has 9,914 square feet, five bedrooms, six full bathrooms and one half bathroom on 0.7 acres in the heart of the historic borough. Stone terraces and an upper balcony overlook the gardens and an in-ground pool. Inside are a renovated kitchen with Thermador appliances, a separate catering kitchen and butler's pantry, hand-painted wallpaper, a crystal chandelier and six fireplaces. It has been on Zillow for 51 days.
Just behind it is the Crossover Estate at 455 Stonington Road, listed at $4,459,000. The 1956 house offers one-level living in 9,009 square feet, with seven bedrooms, three full bathrooms and three half bathrooms. The property is bordered by a pond and brook on one side and an estuary leading to Long Island Sound on the other. Zillow lists 20 acres; the description says 21. It has been on Zillow for 125 days.
Rounding out the top three is a 96.3-acre coastal estate at 305 Pequot Trail in Pawcatuck, listed at $4,395,000 after a $230,000 price cut on Oct. 1. Zillow lists the 2012 main house at 3,000 square feet with three bedrooms, two full bathrooms and one half bathroom. The listing adds a two-level guest house of about 2,000 square feet, for about 5,000 square feet, four bedrooms, three full bathrooms and two half bathrooms in all. It has been on Zillow for 142 days.
No. 4 is a package at 152 & 156 Whitehall Ave. in Mystic, listed at $4,350,000. It includes a 2005 main house and a carriage house rented out, plus a separate legal parcel with a two-family house or a building lot, according to the listing. Zillow counts 9,872 square feet, 10 bedrooms, eight full bathrooms and two half bathrooms on 4 acres for the whole package. A boat launch onto the Mystic River is just down Whitehall Avenue. The package has been on Zillow for 199 days.
Closing out the top five is 39 Chippechaug Trail on Masons Island, listed at $3,995,000 after a $1 million price cut on Oct. 22. The 1968 house has 4,293 square feet, four bedrooms, three full bathrooms and one half bathroom on 2.05 acres with more than 250 feet of waterfront, 180-degree water views, a private sandy beach, deep-water access and its own dock. It has been on Zillow for 172 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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