WILTON, CT — Wilton's five most expensive homes for sale on Zillow.com are all priced above $3.3 million, led by a newly finished house just shy of $5 million. The list also includes a glass-walled modern retreat and a midcentury post-and-beam home by an architect who studied under Mies van der Rohe.
No. 1 on the list is 48 Old Farm Road, a newly completed house behind stone walls, listed at $4,999,999 after a $190,000 price cut on Oct. 13. The 8,368-square-foot home has five bedrooms, five full bathrooms and three half bathrooms on 2.27 acres. It pairs New England architecture with a modern interior: pale oak floors, a staircase with black metal balusters and bedrooms with vaulted ceilings. It has been on Zillow for 82 days.
Just behind it is 300 Sturges Ridge Road, a 2008 modern house on 2.6 acres next to protected open space, at $4,695,000. The 7,907-square-foot home has five bedrooms, four full bathrooms and one half bathroom, walls of glass, a Poliform kitchen, a glass mosaic wine cellar and a skylit gym. Outside are a heated saltwater pool and spa, an outdoor kitchen, a fire pit and a Zen garden. It has been on Zillow for 40 days.
Rounding out the top three is 21 School Road, a fully fenced estate of more than 4 acres in the center of town, listed at $3,999,999. The 1966 house has 7,793 square feet, six bedrooms, five full bathrooms and two half bathrooms, double-gated entrances and a chef's kitchen with a fireplace. It has been on Zillow for 19 days.
No. 4 is 24 Graenest Ridge Road, asking $3,800,000. The original 1950s post-and-beam house was designed by Robert Peterson, who studied under Mies van der Rohe. A zinc-and-glass addition by architect Zehra Kuz Mackin was built to hold an art collection, guests and vintage cars. The 4,386-square-foot home has three bedrooms, three full bathrooms and one half bathroom on 2.32 acres. It has been on Zillow for 61 days.
Closing out the top five is 112 Vista Road, a fully renovated 2006 house overlooking the Silvermine River near Wilton Center, at $3,350,000. The 6,899-square-foot home has six bedrooms, five full bathrooms and two half bathrooms on 2.14 acres, with 9-foot ceilings, Brazilian cherry and red oak floors, smart-home technology and a designated pool site. It has been on Zillow for 121 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.
Sign up for free local newsletters and alerts for the
Wilton Patch
Patch.com is the nationwide leader in hyperlocal news.
Visit Patch.com to find your town today.