Chester Real Estate

Welcome to Chester, Massachusetts – a hidden gem nestled in the heart of Hampden County. This quaint town, rich in history and natural beauty, offers an idyllic escape from the hustle and bustle of city life. With a population of just over 1,000 residents, Chester boasts a close-knit community that prides itself on its warm hospitality and picturesque surroundings.

Surrounded by lush forests and rolling hills, Chester is an outdoor enthusiast's paradise. The town is home to the stunning Chester-Blandford State Forest, where hiking, biking, and nature walks abound. In the winter months, residents and visitors can enjoy nearby ski resorts, making Chester a year-round destination for adventure seekers.

History buffs will appreciate Chester’s charming downtown area, where you can find beautifully preserved historic buildings that tell the story of the town's rich past. The local library and community center often host events, fostering a sense of community and connection among residents.

Chester is also conveniently located, making it easy to access larger cities like Springfield and Pittsfield for shopping, dining, and entertainment. Yet, you’ll find that the town itself offers delightful local eateries and shops, where you can savor the flavors of New England.

Whether you’re looking to settle down in a peaceful environment or seeking a weekend getaway filled with outdoor activities, Chester, MA, is the perfect place to call home. Experience the charm of this picturesque town and discover all that it has to offer!

Newest Listings in Chester

$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.

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