$296,413Average Value$254Average Price per Sq Ft12Homes For Sale
A quintessential hometown Adirondack community
Celebrating its 225th anniversary in July 2024 with a car show, bounce house, food trucks and corn hole, Chestertown is a small Adirondacks town driven by community. “Events and local businesses separate this small town from larger cities,” says Julia Pucciarelli, local chamber of commerce member and Realtor with Gallow Realty ADK. “The community is driven by wonderful organizations, like the Chestertown Rotary, the Historical Society, Friends of the Library and the Tri-lakes Community Alliance.” Pucciarelli has lived in Chestertown for the past 10 years after getting married and has worked in real estate for the last 5 years. “I fell in love with the people,” she says. “Here, you have your own slice of heaven.” From natural lakes made for swimming, fishing and boating to mountain resorts designed for hiking, ziplining, skiing and snowmobiling, Chestertown offers four seasons of recreation that attract outdoor enthusiasts. “We’re the quintessential hometown USA,” says Angie Mead, the broker of Gallow Realty ADK. “Safety and access to the great outdoors is important to buyers here. I have a five-year-old and am lucky to live and work in Chestertown. It has what kids need — to get outdoors and be kids.”
Eateries and shops along Main Street
Chestertown takes pride in its many businesses and services on Main Street. For example, the town hall is a repurposed schoolhouse and functions more like a community center, housing the town library, food pantry, court and YMCA. Defined as a regional wellness center, the YMCA features cardio equipment, strength training machines, free weights and experienced trainers. Visitors can browse artwork by Adirondack and Capital District artists at Birds of a Feather Studio and Gallery. The Bullhouse Kitchen and Bar is next door in the historic Remington Building. This local eatery specializes in upscale comfort food with a Latin American influence. The Carol Theater is nearby, too. It hosts movies and special events like summer concerts. The Main Street Ice Cream Parlor serves not only ice cream but also breakfast and lunch. Panther Mountain Traders showcases local artisan-made goods, such as nature-inspired children’s books, gifts and home furniture. Tops is the primary grocery store across the street from the town hall on Main.
Catch the latest music show at the Carol theater in Warrensburg.
Explore local art and crafts at Birds of a Feather Studio and Gallery in Chestertown.
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Events for canines, cooks, kids and creatives
Dog lovers in Chestertown delight in Woof Stock each June at the town hall. This annual weekend festival features food and pet vendors, tie-dye pet costume contests, live music, pet adoptions, grooming and a blessing of the animals. June through September, the Chestertown Farmers Market is held at the town hall on Wednesdays. The market features over 30 vendors, including local farmers, woodworkers, jewelry makers and bakers. Another classic Adirondack tradition is February’s Krazy Downhill Derby. Winter enthusiasts can test their imagination and engineering skills by creating hand-crafted sleds for a race down Dynamite Hill in Chestertown. Sleds that resemble a pirate ship, shark, rocket, wide-mouth bass and firetruck have all entered this creative, family-friendly competition.
Enjoy fresh fruits, vegetables, and homemade goods at the Chestertown Farmers Market.
Explore a variety of local treats at the Chestertown Farmers Market.
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Second homes with a growing year-round appeal
Many of the homes on the market in Chestertown are historic houses built in the late 1800s or newer homes from the 1970s. Most are bought for vacationers. “Chestertown remains a second home market,” Mead says. “Eighty percent of sales go to buyers looking for a vacation home.” Yet, since Covid, Pucciarelli has noticed that the quiet beauty of the area has convinced many new buyers to move to Chestertown year-round. “They start with small trips up here and eventually decide to make it their home,” she says. “Recently, I sold a house to a young couple from Albany who want to raise a family. They fell in love with the woods, mountains, lakes and people here.” While inventory remains low, historic and suburban homes along Main Street sell for $200,000 to $350,000. Mountain retreats on 40 acres or more of land can sell for $500,000. The town also offers several commercial properties with a storefront or office space and residential units upstairs. These can range from $300,000 to $750,000.
Chestertown offers a mix of historic and modern homes for every lifestyle.
Discover cozy cottages and spacious estates in Chestertown.
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A small Adirondack school with big wins
North Warren Central School is a PK-12 public school serving the Chestertown community that received a C from Niche. The student-teacher ratio at this combined elementary, middle and high school is 8 to 1, less than half the national average of 17 to 1. “The school graduates 40 kids per year,” Mead says, emphasizing the small percentage of homeowners who live year-round in the community and send their children here. While total enrollment is 465, the number of works of art, woodshop and floriculture presented at the school’s 2024 Art Show was over 1,000. Also in 2024, the North Warren Central boys basketball team won their first Class D state championship.
The North Warren school offers quality education for PK-12 students in Chestertown.
The North Warren Central school prepares their students for academic success.
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Mountains, lakes and trails around Chestertown
Gore Mountain is a world-renowned, alpine ski resort just 15 miles west of Chestertown. It’s the state’s largest ski area, with four large and three smaller peaks. The resort has also broken ground on its new multimillion-dollar North Creek Ski Bowl project, which includes a new lodge, lift and summer attraction due to be completed in 2025. Another big attraction 20 miles north of town is Pharaoh Lake Wilderness Area, which covers over 45,000 acres and includes Pharaoh Lake, one of the largest lakes in the Adirondacks. Visitors can hike, fish, canoe and hunt there. The park also offers horseback riding, cross-country skiing and snowshoeing trails. Lakes like Loon, Brant and Friends are integral to Chestertown's geography and offer more water recreation opportunities. The town started the Chester Challenge with a grant from Glens Falls Hospital to promote physical fitness and local hiking trails. To receive their challenge pin, hikers must complete six of 11 local trails, such as the Dynamite Hill and Caroline M. Fish Memorial Trails. With a small 65-foot hill good for beginners, Dynamite Hill is also used for skiing, sledding, snowboarding and ice skating. Road and mountain bikers can choose from several routes in the area, from a loop around Friends Lake to a stopover at the Hub, a bike shop, bar and café with live music and stunning views of Brant Lake.
1. Explore the scenic Caroline M. Fish Memorial Trail for a peaceful hike in Chestertown.
The Hub in Brant Lake is your go to place for bike repairs and rentals.
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Transportation and services for Chestertown
Trailways buses offer curbside pickups in Chestertown, southbound on Main Street/Route 9 in front of city hall and northbound in front of Tops Friendly Markets. Chestertown’s historic district, which covers 2 square miles and intersects Route 8 and Route 9/Main Street, is walkable and bikeable from most in-town homes. Interstate 87 is less than 2 miles away and connects with Albany, 80 miles south, and New York City, 230 miles south. Burlington, Vermont, is only 85 miles north. The closest major airport is Albany International Airport, 75 miles south; the closest Amtrak station is in Saratoga Springs, 50 miles south; and the closest hospital is in Gens Falls, a 30-mile drive south. Chestertown also has a handful of churches, which include two Catholic, one Methodist and an Episcopal house of worship.
Flood risk for homes along routes 8 and 9
Established by New Englanders who built mills on streams like Chester Creek, Chestertown is prone to flooding in those areas. A dozen or more properties along routes 8 and 9, where Chester Creek crosses and runs alongside the highway to Faxons Pond, are often affected. These properties include homes and businesses on Pine Street, Laflure Lane, Riverside Drive, North Mill Street and Pine Knolls Road. Other areas of town that experience flooding are undeveloped or do not affect buildings.
Written By
Christopher Kopczynski
Photography Contributed By
Augusto Abreu
Video By
Christine Tranchina
Interested in learning more about homes in this area?
Reach out to
Amanda Gadway,
an experienced agent in this area.
GreatSchools:
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On average, homes in Chestertown, NY sell after 38 days on the market compared to the national average of 50 days. The median sale price for homes in Chestertown, NY over the last 12 months is $335,000, consistent with the median home sale price over the previous 12 months.
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One of a kind setting, this well built beloved Ranch home with 9+ acres, 3 bedrooms, large LR with stone fireplace, 1 bathroom, full basement with laundry area and lots of storage shelves. Exterior with fenced in pet area, huge detached deck, front porch, perennial shrubs surround, paved driveway, 2 car garage with attached workshop. Privacy yet close to the town of Chestertown. With some
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