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$235,000
3 Beds ⋅ 1 Baths ⋅ 73568776 MLS
OPEN HOUSE SCEDULED FOR 8/29 HAS BEEN CANCELLED

11 Maple St, Chester

Listing courtesy of Listing Agent: Kolleen E. Schmitt from Listing Office: Keller Williams Realty.
$225,000
2 Beds ⋅ 1 Baths ⋅ 73563768 MLS
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 potential. Book your showing and bring your vision. Water heater purchased in 2021. Roof on addition was put on this year APO. Roof on main part of house is about 12 years old. 500 gal propane tank is owned. Buyer to do due diligence.

23 Maple St, Chester

Listing courtesy of Listing Agent: Keira Hildack from Listing Office: Keller Williams Realty.
$45,000
73563694 MLS
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 structure. A well and septic system will be required. Buyers are encouraged to conduct their own due diligence with the town regarding building, septic, well, permits, and allowable uses.Bring your design. Bring your vision. Bring your dreams. This could be the opportunity to create something truly your own on 10 acres of land.

50 Smith, Chester

Listing courtesy of Listing Agent: Nicolle Serafino from Listing Office: Keller Williams Realty.
$250,000
2 Beds ⋅ 1 Baths ⋅ 73562806 MLS
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! The living room with hardwood floors and a gas stove for cozy winter nights offers a large bow window to let in the natural light. The kitchen is bright and spacious with cathedral ceilings and a dining area. Convenient first floor laundry off the kitchen too. Good size bedrooms! The main bedroom has 2 closets, sliders to the wrap around deck and sunroom. This truly special home is move in ready. Garage area, two storage sheds, garden beds and nicely landscaped. This one has it all, for year round or vacation living! Great location! An easy drive to the Berkshires and Northampton. Close to all the great local amenities, historic town center, Chester Theater and never ending popular recreational spots all through-out the hilltowns! Call today.

28 Hampden St, Chester

Listing courtesy of Listing Agent: Victoria Minella-Sena from Listing Office: Berkshire Hathaway HomeServices Realty Professionals.
$100,000
2 Beds ⋅ 2 Baths ⋅ 73561688 MLS
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 water tank installed approximately three years ago.

166 Route 20, Chester

Listing courtesy of Listing Agent: Thomas Despard from Listing Office: Nexthome Elite Realty.
$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.
$2,000,000
4 Beds ⋅ 4 Baths ⋅ 73531137 MLS
Discover exceptional luxury living at 32 Colby Farm Road, a custom-designed 5,110-square-foot farmhouse set on a picturesque one-acre homesite in Chester, New Hampshire. Thoughtfully crafted with high-end finishes and timeless design, this stunning home features dual primary suites, including a first-floor retreat with heated bathroom floors, two walk-in closets, and private deck access. The chef’s kitchen is equipped with premium Thermador appliances, an oversized island, quartz surfaces, and a fully appointed butler’s pantry. Additional highlights include two laundry rooms, a private office, media room, expansive great room, walkout lower level with future expansion potential, and a three-car garage with 12-foot ceilings. This home offers the perfect balance of privacy and convenience. Located minutes from Route 93, Manchester-Boston Regional Airport, and major commuter routes, Boston is approximately 50 minutes away and Manchester-Boston Regional Airport, and major commuter routes.

32 Colby Farm Rd, Chester

Listing courtesy of Listing Agent: Jo-Ellen Redmond from Listing Office: eXp Realty LLC - Corporate Office.
$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. It also includes a newly updated oil furnace. 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.
$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

Listing courtesy of Listing Agent: Melissa L. Blondek from Listing Office: Gallagher Real Estate.
$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..
$249,900
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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