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254 Route 20, Chester
$229,900
2 Beds ⋅ 2 Baths ⋅ 73594709 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: Coldwell Banker Realty - Western MA.
47 Lyon Hill Rd, Chester
$495,000
3 Beds ⋅ 2 Baths ⋅ 73594566 MLS
Custom-built Contemporary is ready for its second owner. Perfect blend of comfort, privacy and natural beauty on 9.7 acres. Meander on the 9.7 acres with a babbling brook that can be heard from the front porch. There are distant mountain views, not visible from the house. The main floor features a kitchen with cabinets galore and a wine frig, cathedral ceiling in the dining room with a fireplace, generous size living room with views to the outside, two bedrooms and a bathroom. The second floor features a generous size bedroom with a private bathroom and an open sitting area that could function as a study. Partially finished basement with a room that functioned as a prior wine cellar. The kitchen and bathroom were updated 14 years ago, approximately. There is enough frontage for the potential for another lot or lots, buyer to verify, the property is being sold as one lot. The seller is installing a new septic system.

47 Lyon Hill Rd, Chester

Listing courtesy of Listing Agent: Debra A. Petrovsky from Listing Office: Donovan Real Estate.
27 Maple Ave, Chester
$290,000
3 Beds ⋅ 2 Baths ⋅ 73589335 MLS
Very well-maintained home on dead end street within walking distance to store, 2 restaurants and library. Walk out onto the back deck, to a nice size yard, with the West Branch of the Westfield River in your back yard. Come home and stick your toes in the water and relax to the serene sound of the babbling river, after a long day. 2 story conventional style home with 6 rooms, 3 bedrooms, 1.25 baths, 1 car attached garage and a cute front porch. Title V failed, perc test done, design completed and out for bid. and new septic system to be installed. Same owner for 50 years and it is time for new owners to enjoy this ready to move in home. Be in for the holidays. Don't miss this sweet home.

27 Maple Ave, Chester

Listing courtesy of Listing Agent: Kathleen A. Engwer from Listing Office: RE/MAX Compass, Lee MA.
2 Taft Rd, Chester
$39,000
73586614 MLS
Unique Property with Multiple Outbuildings and Versatile Use Potential Discover a rare opportunity in Chester — a property offering multiple outbuildings, upgraded utilities, and flexible space for storage, recreation, or future development.The land includes two well-built sheds:Utility Shed — insulated, equipped with electric heat, and houses the well pump, providing reliable year-round functionality. Cabin-Style Shed — transformed into a comfortable retreat with 200-amp electrical service, electric heat, and full insulation, making it ideal as a workshop or hobby space.A metal shipping container on the property adds substantial secure storage for equipment, tools, or recreational gear. Whether you’re looking for a getaway spot, a base for outdoor activities, or a property with ready-made utility structures, this location offers exceptional versatility.

2 Taft Rd, Chester

Listing courtesy of Listing Agent: Todd Kazunas from Listing Office: Gallagher Real Estate.
Mica Mill Rd, Chester
$129,000
73582709 MLS
Opportunity to own 28.00 acres in Chester's rural hilltown setting. Located at 0 Mica Mill Rd, this vacant parcel is identified in town records as AR Agricultural Residential and offers a canvas for a future homesite or other potential use, subject to all required approvals. Enjoy a quiet western Massachusetts location with access to the Berkshires and Pioneer Valley region. Buyer and buyer's agent to independently verify all information and perform all due diligence, including boundaries, legal access and road status, zoning, permitted uses, wetlands, soils/perc, septic, utilities, and any development or subdivision potential. Parcel map is for location reference only and is not a survey.

Mica Mill Rd, Chester

Listing courtesy of Listing Agent: Jaquaine Coe from Listing Office: The LGCY Group LLC.
93 Crane Rd, Chester
$129,900
1 Baths ⋅ 73579781 MLS
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 the property. Surrounded by wooded acreage, the setting offers privacy, natural beauty, and plenty of room to enjoy the outdoors. In the meantime, the existing cottage makes an excellent weekend getaway, hunting lodge, or recreational retreat. Built in 2011 with a metal roof, wood exterior, the cottage provides a solid starting point. A special opportunity to build a year-round home in a peaceful Western Massachusetts setting while enjoying the property today. Buyer to perform all due diligence regarding zoning, permitting, building requirements, and future use.

93 Crane Rd, Chester

Listing courtesy of Listing Agent: Daniel James Piasecki from Listing Office: Coldwell Banker Community REALTORS®.
23 Maple St, Chester
$215,000
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. Property appraised for 239k.

23 Maple St, Chester

Listing courtesy of Listing Agent: Keira Hildack from Listing Office: Keller Williams Realty.
50 Smith, Chester
$40,000
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.
166 Route 20, Chester
$80,000
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.
lot 3 Holcomb Road, Chester
$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.
lot 2 Holcomb Road, Chester
$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.
lot1 Holcomb Road, Chester
$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.
91 Lynes Rd, Chester
$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.
27 Main St, Chester
$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.
20 Main St, Chester
$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.
95 Lynes Rd, Chester
$40,000
73528786 MLS
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 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 boundaries to their satisfaction. Seller is the conservator and has no information on the property. Buyer to perform all due diligence for use. Broker and Seller make no representations. Requires a license to sell. Property is 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.
1 Crane Rd, Chester
$150,000
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.
56 Middlefield 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

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

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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