GREENWICH, CT — The most expensive home for sale in Greenwich is listed at $100 million.
Cedar Cliff, a 1930 Mediterranean villa on a gated peninsula in Riverside, leads a list on Zillow.com where every one of the town's five priciest homes is priced above $28 million.
108 Cedar Cliff Road in Riverside is asking $100,000,000, or roughly $7,600 a square foot. The villa, which is the former home of Kathie Lee Gifford, sits on 2.91 acres in the Indian Head Association with more than 1,250 feet of waterfront and views of Long Island Sound and the Manhattan skyline.
According to the listing, the land was once the compound of railroad magnate Henry Francis Shoemaker and later home to the Cedar Cliff Beach Club in the 1920s, and the road takes its name from Shoemaker's villa. The 13,163-square-foot house has eight bedrooms, nine full bathrooms and five half bathrooms, a three-level elevator and antique wood floors. It has been on Zillow for 160 days.
Just behind it is 14 Meadow Lane, a Georgian Colonial on 14.49 acres two miles from Greenwich Avenue, at $34,995,000. Designed by Paul Stephan Marchese & Associates and built by Hobbs Inc. in 2010, the 14,131-square-foot main house has five bedrooms, seven full bathrooms, one half bathroom and an elevator. The compound also includes a stone pool house, two cottages, a tennis court and the original stables of actor George C. Scott, according to the listing. It has been on Zillow for 24 days.
Rounding out the top three is a two-house estate at 38-48 and 58 Quaker Lane, listed at $30,000,000. Behind iron gates, a renovated shingle-style house with five bedrooms and seven fireplaces sits high on 16 acres with western views, orchards, a vineyard, an infinity-edge pool and a one-bedroom guest cottage. The sale also includes a neighboring 12-horse equestrian property with a five-bedroom Mediterranean house. Zillow counts 10,800 square feet, 11 bedrooms, nine full bathrooms and three half bathrooms for the whole package. It has been on Zillow for 26 days.
No. 4 is a building site as much as a house: 500 Round Hill Road, nearly 20 acres at a 560-foot elevation that the listing calls one of the highest points on Round Hill, asking $29,900,000. The property now has a 2015 stone guest house of more than 7,000 square feet with six bedrooms, six full bathrooms and one half bathroom, meant to be lived in while a new main house of 22,000 square feet or more is built. It has been on Zillow for 25 days.
Two estates are tied for No. 5 at $28,500,000. 39 Brookridge Drive is a new white-brick house on 2.43 level acres in town, due in 2027, with 18,370 square feet, seven bedrooms, eight full bathrooms and four half bathrooms, a pool, a sports court and a barn with an office, a half basketball court and a golf simulator. It has been on Zillow for 200 days.
The other, 380 North St., sits on a hilltop the listing says was historically known as "Electric Hill," once part of the estate of Edward H. Johnson, Thomas Edison's associate and a pioneer of electric lighting in homes. The 2008 stone Georgian, designed by Mark Finlay and built by Hobbs, has 12,006 square feet, five bedrooms, six full bathrooms and two half bathrooms on 5.22 acres, with views of the Sound over the treetops. It has been on Zillow for 46 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.
Seven Bridges, a $48 million, 48-acre backcountry property at 114 John St. whose two stone, glass and timber buildings long housed the Seven Bridges art collection, was not ranked.
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