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Chester, MA Homes for Sale

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  • 56 Middlefield Rd, Chester, MA 01011
    56 Middlefield Rd, Chester, MA 01011
    56 Middlefield Rd, Chester, MA 01011
    /39

    $394,900

    • 5 Beds
    • 4 Baths
    • 2,832 Sq Ft

    56 Middlefield Rd, Chester, MA 01011

    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,

    Agent Photo

    Cynthia Gonzalez

    Executive Real Estate, Inc.

    (413) 966-0486

    56 Middlefield Rd, Chester, MA 01011
  • 6 Maple St, Chester, MA 01011
    6 Maple St, Chester, MA 01011
    6 Maple St, Chester, MA 01011
    /28

    $235,000

    • 6 Beds
    • 2 Baths
    • 4,132 Sq Ft

    6 Maple St, Chester, MA 01011

    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

    James Adams Hilltown Real Estate by Adams Realty

    6 Maple St, Chester, MA 01011
  • 67 Bromley Rd, Huntington, MA 01050
    67 Bromley Rd, Huntington, MA 01050
    67 Bromley Rd, Huntington, MA 01050
    /34

    $319,000

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft

    67 Bromley Rd, Huntington, MA 01050

    Come see this little slice of heaven. newly updated throughout including LVP flooring, fresh paint, new stainless Appliances. Beautiful Butcher block Countertops and updated Cabinets. Step out onto your deck directly off of the kitchen/dining area and enjoy your morning coffee or tea or sit and enjoy a cup of wine as you take in the scenic views. lots of natural light with generous sized rooms

    Brian Othmer Proactive Realty

    67 Bromley Rd, Huntington, MA 01050
  • 0 E River Rd Lot 13 Map 409 Unit 72690617, Chester, MA 01050
    0 E River Rd Lot 13 Map 409 Unit 72690617, Chester, MA 01050
    0 E River Rd Lot 13 Map 409 Unit 72690617, Chester, MA 01050
    /7

    $75,000

    • Land
    • 18.05 Acres
    • $4,155 per Acre

    0 E River Rd Lot 13 Map 409 Unit 72690617, Chester, MA 01050

    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

    Victoria Minella-Sena Berkshire Hathaway HomeServices Realty Professionals

    0 E River Rd Lot 13 Map 409 Unit 72690617, Chester, MA 01050
  • 147 Chipman Rd, Chester, MA 01011
    147 Chipman Rd, Chester, MA 01011
    147 Chipman Rd, Chester, MA 01011
    /42

    $460,000

    • 3 Beds
    • 2.5 Baths
    • 2,068 Sq Ft

    147 Chipman Rd, Chester, MA 01011

    Welcome home to this peaceful & serene 3 bed, 2.5 bath contemporary offering an open floor plan, main-level primary suite, & a private trail leading to the wild streambed of Glendale Brook! Enter through the welcoming foyer to the main level that features a spacious living room & dining area w/ propane stove & sliders to a sunny deck, a kitchen with pantry closet, half bath w/ laundry, a

    Taylor Hildack Keller Williams Realty

    147 Chipman Rd, Chester, MA 01011
  • 254 Route 20, Chester, MA 01011
    254 Route 20, Chester, MA 01011
    254 Route 20, Chester, MA 01011
    /38

    $279,500 Open Sun 11:30AM - 1PM

    • 3 Beds
    • 1.5 Baths
    • 1,968 Sq Ft

    254 Route 20, Chester, MA 01011

    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

    Dennis LeClair RE/MAX Compass

    254 Route 20, Chester, MA 01011
  • 187 Route 20, Chester, MA 01011
    187 Route 20, Chester, MA 01011
    187 Route 20, Chester, MA 01011
    /23

    $208,900

    • 2 Beds
    • 1 Bath
    • 860 Sq Ft

    187 Route 20, Chester, MA 01011

    Charming 2-bedroom, 1-bath home tucked away in the peaceful Hill Towns, offering comfort, character, and a scenic natural setting. A beautiful stream runs along the rear of the property, and the small, manageable lot makes upkeep easy while still providing room to enjoy the outdoors. Inside, the home features bright, welcoming spaces ideal for simple, low-maintenance living. Whether you’re

    Timothy Coughlen Park Square Realty

    187 Route 20, Chester, MA 01011
  • 84 Middlefield Rd, Chester, MA 01011
    84 Middlefield Rd, Chester, MA 01011
    84 Middlefield Rd, Chester, MA 01011
    /36

    $240,000 Open Sun 12:30PM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,945 Sq Ft

    84 Middlefield Rd, Chester, MA 01011

    Discover the perfect blend of historic charm and modern potential at 84 Middlefield Rd- located in the center of a quaint Western Massachusetts Hilltown. This 3-bedroom, 2-bath, single-family, antique farmhouse home offers 1,945 sq ft of living space on a cute postage stamp yard at the corner. The layout is spacious and the architecture is classic New England appeal. Ample space for your family

    Danielle Lafond Berkshire Hathaway HomeServices Realty Professionals

    84 Middlefield Rd, Chester, MA 01011
Massachusetts Hampden County Chester

Real Estate & Homes for Sale in Chester, MA

Why Live in Chester

Chester, Massachusetts, is a secluded hillside community located approximately 30 miles west of Springfield. Known for its privacy and tranquility, Chester appeals to residents seeking a quiet lifestyle, including musicians who appreciate the solitude for creative pursuits. Homes in Chester are surrounded by dense forests that showcase vibrant fall colors, and the area offers four-season recreational activities such as hiking and cross-country skiing. While major grocery shopping requires a drive to Westfield, local entertainment is readily available with the Chester Theatre Company producing acclaimed summer shows. Architectural styles in Chester range from Colonials and Cape Cods to contemporary designs, with many homes featuring decks or porches for enjoying the peaceful surroundings. The community is not particularly walkable or bikeable due to its spread-out nature. Chester boasts a thriving arts scene, with the Chester Theatre Company and the Chester Railway Station & Museum being notable attractions. Outdoor enthusiasts can explore Chester-Blandford State Forest, which offers hiking, snowmobiling, mountain biking, and more. Chester Town Park and Hampden Street Park provide additional recreational options. The Gateway Regional School District serves the area, though the schools have average ratings. Dining and shopping options within Chester are limited, but nearby Westfield offers more variety. Chester is connected to the rest of Hampden County via Route 20, which leads to Springfield and connects to Interstate 90. Bradley International Airport is 40 miles away, and Baystate Noble Hospital is a 30-minute drive from Chester.

Learn more about living in Chester

Frequently Asked Questions

What is the average home price in Chester, MA?
Homes for sale in Chester, MA have an average home price of $362,583.
How many homes have sold over the last 12 months in Chester, MA?
26 homes have sold in Chester, MA over the last 12 months.
What are the most popular zip codes in Chester, MA?
The most popular zip codes in Chester, MA include 01050, 01011, 01243, 01008 and 01223.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $324,900. If you put a 20% down payment of $65,000 and had a 30-year fixed mortgage with an interest rate of 6.3%, your estimated principal and interest payment would be $1,610 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $69K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Chester, MA?
Chester, MA has highly rated public and private schools. Some of the best schools in Chester based on Niche Grades are Wahconah Regional High School, Chester Elementary School and Gateway Regional High School. Browse all the schools in Chester, MA to learn more.

Home Trends in Chester, MA

On average, homes in Chester, MA sell after 46 days on the market compared to the national average of 56 days. The median sale price for homes in Chester, MA over the last 12 months is $340,000, up 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$340,000
Median Single Family Sale Price
$327,500
Average Price Per Sq Ft
$200
Number of Homes for Sale
4
Last 12 months Home Sales
26
Months of Supply
1.80
Median List Price
$324,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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