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$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.
$225,000
2 Beds ⋅ 1 Baths ⋅ 73416131 MLS
This cedar sided bungalow in a peaceful setting offers an open floor plan, 5.61 acres of land, a private deck overlooking the beautiful yard w/ blueberry bushes, apple & pear trees. Kitchen w/appliances to stay. Cozy DR. Large open LR w/cathedral ceilings. First floor laundry. Full bath w/tub & shower. Potential for a half bath off the empty bedroom (it was a half bath at one time) Abbott Brook runs along the back edge of the property. This would make a great vacation retreat or year-round home. Enjoy the recreational areas & activities all close by or take a short drive to the Berkshires or Northampton. This is an ideal location to be away from it all but not too far from major cities. New hot water tank, newer pressure tank for the well. Septic was new in 2009 & the roof was last redone in 2014. Electric baseboard heat & forced air wood furnace in the basement. Also wood stove hook up in the living room. Some cosmetic TLC needed, bring your imagination to make this home your own

11 Taft Road, Chester

Listing courtesy of Listing Agent: Victoria Minella-Sena from Listing Office: Berkshire Hathaway HomeServices Realty Professionals.
$75,000
72690617 MLS
Private 18 acre lot! 200 feet of frontage & 3000 feet back w/winding trails & a brook. From the road there is a little clearing with ATV trails to the right & an old over grown skidder trail to the left as land has not been logged since 2007. The skidder trail rises up to the top of a ridge & there is a brook in the back left corner. The ATV trails wind gently leading up to the flatter portions w/possible views & home site location potential. There is electric on the street. One mile down the road are the Littleville Fairgrounds and Dayville. Trails criss cross over east river road in a few locations offering you the ability to explore beyond your property into many of the hilltowns' recreational destinations. This property would make a great recreational camp for hunting, fishing, hiking & more or it could be the site to build your dream home. Plot plans & old logging plan in photos. Lot 14 to the right is also for sale different owner, similar lot, possibility to purchase both.

East River Rd Lot 13 Map 409, Chester

Listing courtesy of Listing Agent: Victoria Minella-Sena from Listing Office: Berkshire Hathaway HomeServices Realty Professionals.

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