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$579,900
2 Beds ⋅ 2 Baths ⋅ 5090733 MLS
This property presents a rare opportunity to own a large lot on desirable Chester St. Many options here: Update the house and create a huge farm property, build a new house and use the existing house as an ADU/cottage or other, subdivide into two lots with town approvals ** A beautiful country setting for this 16.4+/- acre farm with wooded areas to explore. ** This classic farmhouse offers 2 bedrooms, 2 baths, large eat-in kitchen, laminate, tile and soft wood floors. NEWER forced hot water boiler. Many farm features: Chicken coop, fenced in areas, 20x24 2-stall horse pole barn, a large barn that was moved to the property from another site in Chester. Peaceful, yet conveniently located, about 8.5 miles to Exit 4 I-93 and about 6.9 miles to Exit 2 Route 101. About Chester ** WASON POND is where residents can go to enjoy a quiet, natural place to walk, hike, cross-country ski, walk dogs, kayak, picnic, and swim. SCHOOLS: Consists of elementary & middle school, Chester Academy and the High School is Pinkerton Academy, in Derry. SCARECROWS: The town has been going scarecrow crazy for many years. Every October there are over 400 scarecrows placed all over town with a map showing the locations. The scarecrows will be on display through Oct. 31. HALLOWEEN NIGHT: Brings many visitors to Chester Street, where over the years Trick or Treat has become a must-see event. AGENTS & BUYERS to do their own Due Diligence to verify all listing information and verify options with town and necessary approvals to do so. Room sizes are for reference only; not guaranteed. *** House being sold in current condition and all items on the property to remain after month-to-month tenant leaves. House is tenant occupied and works from the house.

197 Chester St, Chester
$185,000
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
$1,250,000
3 Beds ⋅ 3 Baths ⋅ 5072786 MLS
HOME TO BE BUILT! THIS IS THE LAST LOT REMAINING!! Welcome to Colby Farm, an exclusive enclave of just 10 beautifully crafted single family homes, tucked away on a quiet cul de sac. Thoughtfully designed with both elegance & functionality in mind, each home offers spacious, customizable floor plans, allowing buyers to select finishes, appliances, and details to reflect their personal style. BRING YOUR OWN PLAN OR BUILD THIS FEATURED HOME. This farmhouse style home is a 3,018 sq. ft. retreat that blends timeless charm with modern living. The plan includes three generously sized bedrooms, two and a half well appointed bathrooms, & a convenient second floor laundry. At the heart of the home, the gourmet kitchen is designed to be tailored to your taste, with allowances for appliances, cabinetry, countertops, and finishes. A large center island & walk in pantry create a space that works beautifully for both everyday living and entertaining. The layout also features a flexible room ideal for a home office or den, an expansive great room for gatherings, & a welcoming mudroom leading to a spacious two car garage, all designed with comfort and livability in mind. Set along a scenic country road, Colby Farm offers the perfect balance of modern luxury and rural charm. A neighboring horse farm and 18 acres of conservation land enhance the peaceful surroundings, while the absence of condo fees adds to the appeal. Choose from the builder’s thoughtfully designed plans or bring your own vision to life. Photos are a facsimile of previous build.

37 Colby Farm Rd, Chester
$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
$1,500,000
4890134 MLS
Builders take notice! This is a rare opportunity you don’t want to miss out on with over 200 acres of undeveloped land in beautiful Chester. Sold together - there are 7 parcels; Tax Map 2 Lots 29, 30, 31, 31-1, 33, 38-1 and lot 39. Road frontage along Pomp Road and all land is in current use. Buyer to pay any fees when taking it out of current use status. Buyer to do their due diligence. Aerial photos coming soon. Also for sale is additional 483 acres in Derry, NH -see MLS 4890183 for more information.

Jack Rd, Chester
$244,900
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

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