Inside Old Lyme's 5 Priciest Homes Currently On The Market

OLD LYME, CT — A beachfront lot with two houses on it tops Old Lyme's most expensive homes for sale, followed by a modern smart home that just took a $600,000 price cut, according to listings on Zillow.com.

No. 1 on the list is 40 Pond Road, listed at $3,975,000 after a $225,000 price cut on Oct. 20. The 6,098-square-foot beachfront lot holds two homes with views of Long Island Sound, one remodeled and one newly built, according to the listing, which pitches the pair as a primary home, a second home or a rental. Zillow lists the property as new construction and combines the two houses into 5,500 square feet, six bedrooms, seven full bathrooms and two half bathrooms. The new house has concrete floors and an open floor plan. It has been on Zillow for 153 days.

Just behind it is 314 Ferry Road, a modern smart home the listing calls Greystone, listed at $3,397,000 after a $600,000 price cut on Oct. 2. Built in 2024 next to a protected wildlife area, it has 4,505 square feet, three bedrooms, three full bathrooms and one half bathroom on 1.12 acres, a rooftop deck and a kitchen with a 10-by-4-foot island and Wolf and Sub-Zero appliances. It has been on Zillow for 208 days.

Rounding out the top three is 41-1 Whippoorwill Road, a new single-level modern farmhouse at the end of a private drive, listed at $1,899,999. It has 3,345 square feet, four bedrooms, three full bathrooms and one half bathroom, a sunroom and covered porches on 13.44 acres next to protected open space. It has been on Zillow for 55 days.

No. 4 is 30-1 Lords Meadow Lane, a new modern-farmhouse-style home listed at $1,650,000 after a $40,000 price cut on Oct. 13, with a limited-time financing incentive through the builder's lender. Built in 2026, it has 5,418 square feet, four bedrooms, four full bathrooms and one half bathroom on 2.43 acres, a main-level primary suite, an oversized quartz island and a three-car garage. It has been on Zillow for 33 days.

Closing out the top five is 25 Johnny Cake Hill Road, an antique Colonial that Zillow dates to 1730, on 1.2 secluded acres near the Old Lyme Country Club, listed at $1,550,000 after a $109,000 price cut on Sept. 30. Recent updates include a new cedar roof, a new HVAC system and new hardscaping around the pool. It has 2,750 square feet, four bedrooms, three full bathrooms and one half bathroom, and has been on Zillow for 56 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.