The border of New York and Connecticut
Sherman is a quiet lakeside haven set in the foothills of Connecticut wine country. “It’s a laid-back bedroom type of community,” says Realtor Barbara Sivba of the Barbara Sivba Team with Coldwell Banker, who’s sold real estate in the area for 32 years. “It’s right on the lake, and you’re only an hour from the theater district in New York City. Manhattan loves to have second homes here.” Residents come to Sherman for the small-town atmosphere and for access to Candlewood Lake, one of the most popular outdoor recreation spots in the state. With access to nearby necessities and directly bordering New York, Sherman is an option worthy of consideration.
Candlewood Lake
“Access to Candlewood Lake is a major draw,” Sivba says. “It’s one of the most sought-after locations. There’s over 60 miles of shoreline.” During the summer, locals head out on this man-made lake in boats and inner tubes or hike the area’s many trails. When the lake freezes over, ice skating, cross-country skiing and ice fishing are popular activities. “There’s also local skiing at Mohawk Mountain,” Sivba continues. “That’s just about 25 miles away, and of course people like to head to Massachusetts and Vermont to ski as well.”
Life by the Connecticut lakeshore
“There’s a wide variety of home styles here,” Sivba says. Options include Modern-influenced three-bedroom split levels priced around $500,000, five-bedroom Modern Traditional homes priced around $770,000, and four-bedroom lakeside lodges costing almost $3.5 million. There are also undeveloped lots available, from 5-acre plots selling for $250,000 to 164-acre plots that reach nearly $3 million. Homes are surrounded by woodland, often sitting on multi-acre lots in the rolling hills of Connecticut wine country.
The Sherman School
Students begin at The Sherman School, which Niche rates a B-plus and was named a National Blue Ribbon School by the Department of Education in 2023. The Sherman School serves students from kindergarten through eighth grade. “After eighth grade, kids can go to any of the high schools in other towns,” Sivba says. This includes Shepaug Valley School, which scores an A-minus and is rated the No. 1 best public high school in the county by Niche. Shepaug offers an agriscience academy program for students interested in agriculture and features a 29-set planetarium on campus for less terrestrial pursuits.
Connecticut wine country
Sherman is settled in the heart of Connecticut wine country, so from April to December locals and visitors often flock to tastings and events. “We have White Silo Farm, which is part of the Connecticut Wine Trail,” Sivba says. “The rhubarb festival is a fun annual event.” White Silo hosts several other produce festivals throughout the summer and weekly Sunday music events from spring to winter. Sherman’s small downtown area is also home to the Sherman Playhouse, which has held community theater performances steadily since 1949.
Necessities in New Milford
Locals can head to the Sherman IGA Supermarket to shop for groceries, or they can drive 6 miles east to New Milford to shop at Big Y. New Milford is also home to the nearest Home Depot and Starbucks. “Everyone wants to know where the Starbucks is,” Sivba says. “You can grab all your essentials in New Milford.” Residents also head to New Milford for Housatonic Brewing, where they can enjoy local beers, live music and weekend visits from food trucks. For a more relaxed atmosphere, Johana’s is a low-key classic diner that serves breakfast all day.
Southeast Station
Sherman residents can travel south 20 miles to Danbury via Route 7, where they can catch Interstate 84 north to Hartford. I-84 also heads 8 miles west to Brewster, where Southeast Station awaits. Trains run from Southeast on the Harlem line to Grand Central Station in just under two hours.
A small New England town
Sherman’s sense of small-town America is most evident during celebrations of national holidays. “People boat down the lake to see the fireworks on the Fourth of July,” Sivba says. “They line the streets with American flags for Memorial Day. It really feels like a hometown. People love that about Sherman.”
![Collin Quinlivan]()
Photography Contributed By
Collin Quinlivan
