Chester Real Estate

Welcome to Chester, Massachusetts – a hidden gem nestled in the scenic Berkshires of Hampden County. With its picturesque landscapes and rich history, Chester offers a unique blend of small-town charm and outdoor adventure, making it an ideal place to call home.

As you stroll through the quaint streets of Chester, you'll be captivated by its historic architecture, featuring beautifully preserved 19th-century buildings that tell the story of a bygone era. The town is steeped in history, with roots dating back to the early 1700s. Residents take pride in their community, hosting various local events throughout the year that foster a strong sense of belonging.

Nature lovers will find Chester to be a paradise. The town is surrounded by lush forests, tranquil rivers, and breathtaking mountain views. Whether you enjoy hiking, fishing, or simply taking in the beauty of the outdoors, Chester has something for everyone. The nearby Chester-Blandford State Forest offers miles of trails, perfect for weekend adventures and family outings.

Education is a priority in Chester, with access to quality schools that provide a nurturing environment for children. The town's close-knit community ensures that families feel supported and engaged, making it an excellent place for raising children.

Living in Chester means embracing a slower pace of life, where neighbors greet each other with a smile and the beauty of nature is just outside your door. With its combination of rich history, outdoor recreation, and a welcoming community, Chester, MA, is not just a place to live—it's a place to thrive. Come discover the charm of Chester and find your perfect home in this enchanting town!

Newest Listings in Chester

$69,000

73543999 MLS

Prime 2-acre farmland pasture. This is a premium building lot with stone walls on a quiet gravel road. Property rear is bordered by protected conservation land, One of 4 lots available.

lot 4 Holcomb Road, Chester

Listing courtesy of Listing Agent: James Adams from Listing Office: Hilltown Real Estate by Adams Realty.

$60,000

73543996 MLS

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.

lot 3 Holcomb Road, Chester

Listing courtesy of Listing Agent: James Adams from Listing Office: Hilltown Real Estate by Adams Realty.

$45,000

73543991 MLS

Prime 2 acre building lot with stone walls on a quiet gravel road. Property rear is bordered by protected conservation land , One of 4 lots available.

lot 2 Holcomb Road, Chester

Listing courtesy of Listing Agent: James Adams from Listing Office: Hilltown Real Estate by Adams Realty.

$45,000

73543989 MLS

Prime 2 acre building lot with stone walls on a quiet gravel road. Property rear is bordered by protected conservation land , One of 4 lots available.

lot1 Holcomb Road, Chester

Listing courtesy of Listing Agent: James Adams from Listing Office: Hilltown Real Estate by Adams Realty.

$50,000

73542747 MLS

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 been searching for a wooded retreat or a land opportunity in a scenic hilltown, this parcel is worth a look. Seller says they had a successful perc test in the 80s. Photos provided are shown for reference only. Buyer to perform all due diligence for use, suitability, property lines, and boundaries. Schedule your visit today! Please do not walk the property without an appointment.

91 Lynes Rd, Chester

Listing courtesy of Listing Agent: Cheryl Malandrinos from Listing Office: HB Real Estate, LLC.

$225,000

73529752 MLS

Mixed-Use Building with Commercial Storefront and Residential Unit Mixed-use building with street-level commercial storefront and residential unit above. The 1,290 SF commercial space is available for lease and it includes hardwood flooring, track lighting, and a dedicated rear work area with industrial wash basins.Located on a corner along Main Street in Chester, the property combines commercial and residential use within a single structure. Additional details available upon request. Sale Price: $225,000

27 Main St, Chester

Listing courtesy of Listing Agent: Jeremy Casey from Listing Office: SR Commercial Realty.

$265,000

73529743 MLS

Mixed-Use Building with Occupied Residential Units and Vacant Commercial Space 20 Main St, Chester, MA is a mixed-use property featuring two fully occupied residential apartments generating rental income and a vacant 2,090 SF ground-floor commercial space for lease: $2,300/Month. The commercial unit offers an open layout suitable for retail, office, or service-based use. Located on a prominent corner with strong Main Street visibility, the property provides flexible use potential for investors or owner-users. Residential units deliver existing income, while the commercial space offers leasing or occupancy upside. Income details and additional property information available upon request.

20 Main St, Chester

Listing courtesy of Listing Agent: Jeremy Casey from Listing Office: SR Commercial Realty.

$50,000

73528786 MLS

Is this 3.54 acre lot shouting your name? Down an unpaved, tree-lined road lies this wooded lot awaiting its new owner. Looking for some small town charm? Chester is known as the "Gem of the Valley." It is home to a variety of activities and amenities, such as the Chester on Track festival, the Railway Museum, a longstanding theatre company, and the Keystone Arch Bridges Trail. Public records and the 2017 aerial image show two sheds on the property, but that has not been verified. Boundary lines shown are approximate and for visual reference only. They are not a survey and should not be relied upon for exact property lines or acreage. Buyer to verify all property boundaries to their satisfaction. Seller is conservator and has no information on property. Buyer to perform all due diligence for use. Broker and Seller make no representations. Requires license to sell. Property being sold as-is with buyer's right to inspections. Please do not walk the property without an appointment.

95 Lynes Rd, Chester

Listing courtesy of Listing Agent: Cheryl Malandrinos from Listing Office: HB Real Estate, LLC.

$210,000

4 Beds ⋅ 2 Baths ⋅ 73520586 MLS

Colonial style home featuring 8 rooms, 4 bedrooms and 2 bathrooms located on 6+ acre lot.

1 Crane Rd, Chester

Listing courtesy of Listing Agent: Melissa L. Blondek from Listing Office: Gallagher Real Estate.

$235,000

6 Beds ⋅ 2 Baths ⋅ 73503205 MLS

This is an outstanding opportunity to buy at well below market value. Both units are in move in condition however a septic system will need to be installed at the buyer's expense. Each unit is very expansive with three bedrooms in each unit. Over 4,000 square feet of living area. Many updates including newer furnaces. This is a very smart investment for a cash buyer or a rehab type loan to remedy the septic system. Chester is a desirable town located in the Berkshire foothills.

6 Maple St, Chester

Listing courtesy of Listing Agent: James Adams from Listing Office: Hilltown Real Estate by Adams Realty.

$365,000

5 Beds ⋅ 4 Baths ⋅ 73461501 MLS

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 bonus room that can be used as an office, playroom, or additional storage. The property sits on a generous lot—close to 1 acre—with a large front yard and expansive backyard that accommodates parking for approximately 6 additional vehicles. Ideal for anyone seeking a tranquil setting with strong rental income potential or a reliable investment opportunity. A barn with a 2-car garage and upstairs loft adds even more versatility and is being sold as is. The home also includes a new septic system, offering added peace of mind.

56 Middlefield Rd, Chester

Listing courtesy of Listing Agent: Cynthia Gonzalez from Listing Office: Executive Real Estate, Inc..

$264,900

3 Beds ⋅ 2 Baths ⋅ 73428417 MLS

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 cabinet space, and closets galore for all your storage needs. Additional features include a spacious three-season front porch that’s surrounded by natural light accented by a beautiful wood ceiling, vinyl windows, an attached 1-car garage, and a storage shed — all situated on a 0.36-acre lot. Located along the scenic Westfield River, this property is a haven for outdoor lovers, with nearby hiking and riding trails, and is just a short drive to Jacobs Pillow, Tanglewood, Lee Outlets, and only 30 minutes to Westfield or the Berkshires.

254 Route 20, Chester

Listing courtesy of Listing Agent: Dennis LeClair from Listing Office: RE/MAX Compass.

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