Take A Tour: Darien's 5 Priciest Homes On The Market Right Now

DARIEN, CT — A waterfront house once owned by actor Christopher Plummer, who played Captain von Trapp in "The Sound of Music," tops Darien's most expensive homes for sale. Long Neck Point holds the top two spots on Zillow.com, both priced near $17 million.

No. 1 on the list is 207-209 Long Neck Point Road, asking $16,995,000. The listing says the 1866 house was once Plummer's and has been carefully renovated and restored by builder Significant Homes and interior designer Cindy Rinfret. Its 8,248 square feet hold five bedrooms, eight full bathrooms and one half bathroom, and most rooms face east over the water. The 2.17-acre property is made up of two separately deeded parcels with 200 feet of waterfront and a private beach. The house is also listed by itself on about an acre, as 209 Long Neck Point Road, for $12,995,000. The two-parcel listing has been on Zillow for 198 days.

Just behind it, down the road at 155 Long Neck Point Road, is a waterfront Colonial on 2.93 acres listed at $16,495,000. The 1850 main house has eight bedrooms, seven full bathrooms, three half bathrooms and eight fireplaces, and a two-bedroom guest cottage brings the property to 11,944 square feet with 10 bedrooms. There's a pool and a private dock. It has been on Zillow for 34 days.

Rounding out the top three is new construction by K&C Builders at 175 Brookside Road, listed at $8,750,000 after a $500,000 price cut on Oct. 5. Zillow lists the house at 11,314 square feet over four finished levels, while the description says about 11,000. It has six bedrooms, eight full bathrooms and one half bathroom on 2.54 acres, with a great room, a study and a cabana-style room that opens to the pool. It has been on Zillow for 147 days.

No. 4 is 3 Coves End Road, a 1912 Colonial reimagined as a light-filled contemporary on a protected cove that, the listing says, never turns to mud flats even at low tide. It hit Zillow three days ago at $7,995,000. The 5,172-square-foot house has five bedrooms, six full bathrooms and one half bathroom on 0.8 acres, long water views and a kitchen with a six-burner Wolf cooktop, two Wolf wall ovens and two Miele dishwashers.

Closing out the top five is the historic Eliaseph Whitney House at 246 Brookside Road, built in 1770 and listed at $7,900,000. The 8,100-square-foot home sits on 4.12 acres, which the listing calls one of the largest parcels of its kind in town, and has seven bedrooms, seven full bathrooms and two half bathrooms, wood-beamed ceilings, several fireplaces and garage space for six cars. It has been on Zillow for 201 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.