Chester’s small-town identity
Chester’s quiet, small-town identity attracts homebuyers to central Vermont looking for a close-knit community. “Chester is a quintessential Vermont Town,” says Thaddeus Abare, a Realtor with Barrett & Valley Associates, and a long-time Chester resident that's been selling houses here for nearly 4 years. “I really enjoy it. It’s really quaint, everyone knows each other.” Potential residents can choose to live in the town’s center closer to local businesses, or on the outskirts with several acres of land. While Main Street and accompanying roads are paved, there’s a large amount of dirt backroads throughout that complement the town’s rustic identity.
Older Cape Cods starting in the $200,000s
Homebuyers can find colonials and Cape Cods from the early- to mid-1900s, ranch-style homes from the late-1900s and contemporary-style houses built in the last 25 years. “There’s definitely more new construction happening in Chester compared to surrounding towns, but there’s still a lot of old and antique homes,” says Abare. Homes in the town’s center sit in subdivisions or are tightly arranged along Main Street, while properties on the outskirts sit along winding country roads with two to twenty acres of land. Houses near the village center typically sell for $200,000 to $600,000, while homes on the outskirts usually go for $300,000 to $700,000. There are also properties boasting several hundred acres of land, selling for between $1 million and $2 million.
Local market, restaurants in town
Locals can find popular local restaurants like Country Girl Diner, which has been serving American favorites in Chester since 1966. There’s also Pizza Stone VT on Pleasant Street and MacLaomainn's Scottish Pub on Main Street. Southern Pie Cafe is also the town’s go-to spot for dessert. “As far as newer places go, Maria’s is a cute little Mexican restaurant here now too,” adds Abare. Smitty's Chester Market is a local grocer on Depot Street, while Dollar General is also in town for essentials. Residents can also travel to Ludlow or Springfield for more shopping.
Fall Fest in September
In September, Chester Festival on the Green celebrates the town’s art and culture. The annual event, which has been held for over 50 years, features over 70 craft vendors, live music and street performers, activities for the family and food vendors. “Last year we had around 3 or 4 times the town’s population come through for it,” says Abare.
Outdoor amenities along Lowers Lane Road
Locals can find the town’s recreation options along Lovers Lane Road, including a municipal pool, skatepark, playground, basketball court, disc golf course, tennis courts and baseball diamonds. Chester Town Forest, which stretches 550 acres, also offers two hiking trails. The Butternut Hill Trail goes to the top of Butternut Hill, while the Lost Mine Loop leads to the town’s abandoned talc-mining site from the late-1800s.
Low student-teacher ratio at Green Mountain Union High
Students may start at Chester Andover Elementary, which teaches kindergarten through sixth grade and gets a C-plus from Niche. They may then attend Green Mountain Union High, teaches seventh through 12th grade with a C and operates with a student to teacher ratio of 11 to 1.
Commuting via Route 11, 103
Because of its rural streetscape, Chester is car dependent. Commuters can take State Route 11 east 8 miles to Springfield, and State Route 103 north 13 miles to Ludlow. The Springfield Hospital is just over 7 miles east, while Albany International Airport is 88 miles south.
Important to Know
Due to Vermont’s unique climate, the state has a mud season that usually lasts from March to June. As the winter snow and frost melts, the area’s dirt and soil are turned into muddy terrain. There are over 1,200 miles of dirt roads throughout Windsor County, meaning commuters may encounter hazardous road conditions and complete road closures during mud season.
![Logan Soter-Reardon]()
Written By
Logan Soter-Reardon
