$326,767Average Value$190Average Price per Sq Ft6Homes For Sale
Small Massachusetts community offers seclusion and relaxation
Chester is a sparsely populated hillside community about 30 miles west of Springfield. Living out in the Massachusetts countryside appeals to those who want privacy, like “musicians who want quiet to write and play music where no one’s gonna’ hear ya’,” says Denise DeSellier, a Broker Associate at Berkshire Hathaway HomeServices with over three decades of real estate experience. “My neighbor once had three bands playing outside and no one ever complained in Chester,” DeSellier says. “When you’re out there, you’re just vegging out.”
Homes are surrounded by thick forests with leaves that turn vivid colors in the fall. Four-season recreation here revolves around the forests, from hiking to cross-country skiing. This rural area requires a drive for major grocery hauls, but residents don’t have to go far for entertainment: the Chester Theatre Company produces highly regarded shows every summer. While some properties in the area are second homes, Chester’s laid-back atmosphere has turned a lot of those into primary residences, and the vast majority of those living here do so on a full-time basis. “These are year-round homes in Chester, not necessarily vacation homes,” DeSellier says.
Hampden Street Park in Chester offers wooded trails and quiet paths through 8 acres of natural beauty.
Chester features contemporary-style homes that blend modern design with a peaceful rural setting.
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Chester’s countryside dwellings
Sidewalks line streets in the center of the community, but Chester is generally too spread-out to be considered walkable or bikeable. Architectural styles here span the centuries, from Colonials to Cape Cods to contemporary styles. Many houses have decks or porches where homeowners can enjoy the peace and quiet from the comfort of a rocking chair. Some homes are clustered in the heart of Chester, and others sit out in the forest surrounded by trees. “There’s not a lot on the market out there, but it’s stable,” DeSellier says. Prices range from about $200,000 to $520,000. Buyers will also typically find that acreage is also for sale.
Chester features a colonial-style duplex that reflects the town’s mix of historic charm and multifamily housing.
A Cape-style home in Chester sits quietly among trees, offering classic New England charm.
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Arts, culture and community events in Chester
For a community of its size, Chester has a thriving theater scene. Known for contemporary theatre, The Chester Theater Company has presented summer shows since 1990, many of which have gone on to tour internationally and have an Off Broadway run. The venue is located across from the recently renovated Hamilton Memorial Library and near the Chester Railway Station & Museum, which invites overnight guests to rent out the wooden caboose. Additionally, the nearby Littleville Fair has been entertaining the area for over a century. Every August, this country fair features activities like truck pulls, raffles and square dancing.
The Chester Rail Museum tells the story of the town's historic railroad legacy.
Chester Theatre Company stages contemporary plays in an intimate setting inside the historic town hall.
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Exploring the forests of northwest Hampden County
In Chester, four-season recreation revolves around the great outdoors. Amongst the forests, nature preserves and campgrounds, locals can choose from hiking trails of all difficulty levels. Chester-Blandford State Forest offers snowmobile trails and dog-friendly hiking trails that pass by a waterfall. The state forest is also a hub for mountain biking, horseback riding, fishing, hunting, picnicking and cross-country skiing. John J. Kelly Wildlife Management Area is a prime spot for birdwatching. Chester Town Park has fields for soccer and baseball, and Hampden Street Park offers walking paths alongside tall trees and a babbling brook.
Chester-Blandford State Forest offers scenic trails and waterfalls in a landscape shaped by old mining roads.
Chester Town Park offers open green space, a playground, and spots to relax in the heart of town.
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The public-school pipeline in Chester
Chester is zoned for the Gateway Regional School District, rated C-plus on Niche. Chester Elementary School, rated C-plus, has a student-to-teacher ratio of ten to one, lower than the national average. Students may advance to Gateway Regional Middle School, rated C, and Gateway Regional High School, rated C-plus. Students at the high school have the opportunity to participate in school-sponsored clubs that include performing arts, academic achievement and the annual yearbook, and they can play 10 different varsity-level sports.
Chester Elementary School serves students from pre-K through sixth grade and is in Chester.
All students love attending the Gateway Regional School in Huntington.
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Chester’s modest shopping and dining scene with more options in Westfield
Chester offers a very small selection of locally owned shops and restaurants. At Carm’s Restaurant and Coffee Shop, folks can enjoy brunch on the porch seven days a week. Chester Village Market has some essentials, but major grocery hauls require a 20-mile drive to Westfield, where the nearest supermarket, Stop & Shop, is located. Other shopping and dining options in Westfield include CVS, Walmart and watering holes like Westwood Restaurant and Pub.
Carm’s Restaurant in Chester serves comfort food in a cozy diner that’s a local favorite for breakfast and lunch.
Chester Village Market offers groceries and essentials in a central location along Route 20 in Chester.
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Navigating the roads of Hampden County
Two-lane roads cut through dense trees, connecting Chester to the rest of Hampden County. Route 20 is the main road through the community, taking drivers into Springfield. Route 20 connects to Interstate 90, a toll road also known as the Massachusetts Turnpike. Chester is 40 miles from Bradley International Airport, and Baystate Noble Hospital is about a 30-minute drive away.
Written By
Laura Copan
Photography Contributed By
Matt Barrett
Video By
Jason Jacot
Interested in learning more about homes in this area?
Reach out to
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GreatSchools:
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On average, homes in Chester, MA sell after 72 days on the market compared to the national average of 55 days. The median sale price for homes in Chester, MA over the last 12 months is $329,000, up 4% from the median home sale price over the previous 12 months.
Welcome to this historic Colonial home nestled in the center of Chester, offering charm and modern potential. Featuring 6 spacious rooms, including 3 generous bedrooms and 1.5 bathrooms, this home is ideal for Living, investors, or those seeking an Airbnb rental opportunity. Inside, enjoy the warmth of beautiful wood floors throughout most of the home, a large kitchen with ample counter and
Tucked down an unpaved, tree-lined road, this 3.54+/- acre wooded lot offers a pleasant setting with classic hilltown charm. Chester, known as the “Gem of the Valley,” is home to the Chester on Track festival, the Railway Museum, a longstanding theatre company, and the Keystone Arch Bridges Trail. Public records and a 2017 aerial image indicate two sheds on the property, though this has not been
The price has improved! Don't miss out. Discover this charming and spacious two-family home nestled in the heart of Chester. Recently refreshed with new flooring throughout and thoughtful cosmetic updates, this well-maintained property is ready for its next owner. Each unit offers 3 comfortably sized bedrooms, 1.5 bathrooms, a large living room, dining area, kitchen, first-floor laundry, and a
Discover 3.47 acres of wooded land tucked along a tree-lined, unpaved road in Chester, known as the "Gem of the Valley." Chester offers a blend of small-town charm and outdoor recreation, from the Chester on Track festival and the Railway Museum to the Keystone Arch Bridges Trail and a vibrant local theatre community. Public records identify the parcel as residential (use code 130). If you’ve
Open land. Prime 2-acre pasture, building lot with stone walls on a quiet gravel road. Property rear is bordered by protected conservation land, One of 4 lots available.
Welcome home to your little slice of a rural countryside community. This property is situated on the west branch of the Westfield River in a quiet but convenient location. Enjoy your coffee on the porch and get lost in the sounds of nature. Inside you will find an open floor plan, a newer primary first floor bedroom, and three rooms upstairs with closets. This home is a hidden gem with tons of
Escape to the scenic hills of Chester with this unique 5.2-acre property offering the opportunity to create your year-round country home. Two major infrastructure investments are already in place with the well and three bedroom septic system. Giving you the head start on your new home. The existing 560-square-foot cottage provides a comfortable retreat while you plan and develop your vision for
Daniel James PiaseckiColdwell Banker Community REALTORS®
Welcome to this historic Colonial home nestled in the center of Chester, offering charm and modern potential. Featuring 6 spacious rooms, including 3 generous bedrooms and 1.5 bathrooms, this home is ideal for Living, investors, or those seeking an Airbnb rental opportunity. Inside, enjoy the warmth of beautiful wood floors throughout most of the home, a large kitchen with ample counter and
10-Acre Land OpportunityBring your vision to this beautiful 10-acre parcel of land and imagine what could be created here. The sellers once had grand plans for this property, but life has changed, creating an exciting opportunity for someone else to bring those plans to life.The property offers the potential to recreate what was once here, with building limited to the footprint/use of the former
Investors take note of the potential offered by this charming colonial home. Property is being sold as-is. The seller prefers a 60-day closing to allow sufficient time for removal of personal items from the house, yard, and barn. Title V has failed and will be the buyer’s responsibility. The home features partially updated plumbing and electrical systems, including an electrical panel and hot
Absolutely charming and lovingly maintained home across the road from Walker Brook! Enjoy the tranquil sounds of the running water, cool off on a hot summer day or cast out a line and enjoy a vacation right at home. Relaxing wrap around deck to enjoy your peaceful surroundings and seasonal views. An amazing sun room that provides for more space to take in the nature around you, even from inside!
Victoria Minella-SenaBerkshire Hathaway HomeServices Realty Professionals
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Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
