DEEP RIVER, CT — The most expensive home for sale in Deep River costs more than four times as much as the next one on the list: a Connecticut River estate with its own dock, according to Zillow.com.
No. 1 on the list is 323 River Road, listed at $3,750,000 after a $200,000 price cut on Oct. 13. The 1996 house sits on 2.52 acres on the river, with a dock and lift and panoramic views across protected conservation land. It has 5,557 square feet, five bedrooms, five full bathrooms and one half bathroom, and the listing says every room takes in the river. It has been on Zillow for 101 days.
Just behind it is 170 Bushy Hill Road, a modern-style 1990 house on 3 acres, listed at $850,000. The 2,606-square-foot home has three bedrooms, two full bathrooms and two half bathrooms, with vaulted ceilings, a striking firebox in the living room, a four-season sunroom, a custom bar, a vegetable garden and mature fruit trees. It has been on Zillow for 91 days.
Rounding out the top three, just $1,000 behind, is 42 Laurel Wood Drive, a Cape Cod the listing calls "The Grand Gathering at Laurel Wood," listed at $849,000. It sits on 1.17 acres at the end of a cul-de-sac with a huge two-story, three-car detached garage and room to park boats and trailers. The 1989 house has 2,989 square feet, three bedrooms, two full bathrooms and one half bathroom and a great room with a soaring ceiling. It has been on Zillow for nine days.
No. 4 is 26 Spring St., an antique the listing dates to about 1830 and Zillow dates to 1832, originally the home of Asahel and Adelia Watrous, listed at $695,000. Restored by its current owners, the 2,052-square-foot house has four bedrooms and two full bathrooms on 0.7 acres, with an eat-in kitchen under vaulted tin ceilings, a living room with a wood stove and a library with built-in bookcases. It has been on Zillow for five days.
Closing out the top five is 2 Pinewood Trail, a modern Cape-style home with its own private pond on a dead-end street, listed at $685,000. The 1990 house has 2,403 square feet, three bedrooms, three full bathrooms and one half bathroom on 1.96 acres, a cathedral ceiling and a finished walkout lower level. It has been on Zillow for seven 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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