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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

    $20K PRICE DROP
    • 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

    Pre-Foreclosure
    • 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
  • 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

    $5K PRICE DROP
    • 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
  • 254 Route 20, Chester, MA 01011
    254 Route 20, Chester, MA 01011
    254 Route 20, Chester, MA 01011
    /38

    $274,900

    $11K PRICE DROP
    • 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
  • 147 Chipman Rd, Chester, MA 01011
    147 Chipman Rd, Chester, MA 01011
    147 Chipman Rd, Chester, MA 01011
    /40

    $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! The main level features a spacious living rm & dining area w/ propane stove & sliders to a sunny deck, a kitchen w/ pantry closet, half bath w/ laundry, a first-floor office, & a primary bedroom w/ ensuite

    Taylor Hildack KELLER WILLIAMS REALTY

    147 Chipman Rd, Chester, MA 01011
  • 302 Middlefield Rd, Chester, MA 01011
    302 Middlefield Rd, Chester, MA 01011
    302 Middlefield Rd, Chester, MA 01011
    /42

    $320,000

    • 3 Beds
    • 1.5 Baths
    • 1,320 Sq Ft

    302 Middlefield Rd, Chester, MA 01011

    Charming and well-maintained 3-bedroom, 1.5-bath Cape set on a private wooded lot offering comfort, space, and a peaceful setting. The light-filled kitchen features stainless steel appliances and an open flow into the dining area, perfect for everyday living and entertaining. Bright and inviting living spaces provide abundant natural light throughout. The flexible layout includes a first-floor

    Alice Kempf Kempf-Vanderburgh Realty Consultants, Inc.

    302 Middlefield Rd, Chester, MA 01011
  • 504 Skyline Trail, Chester, MA 01011
    504 Skyline Trail, Chester, MA 01011
    504 Skyline Trail, Chester, MA 01011
    /19

    $578,900

    • 4 Beds
    • 2 Baths
    • 2,244 Sq Ft

    504 Skyline Trail, Chester, MA 01011

    Set along the scenic Skyline Trail, this fully renovated home offers refined finishes, abundant natural light, and a seamless open layout. A long, estate-style concrete approach creates a striking sense of arrival, leading into a thoughtfully updated interior featuring porcelain tile flooring, modern upgrades, and two fireplaces that add warmth and architectural character. A versatile finished

    Oleg Abramchuk First NationWide Realty Inc.

    504 Skyline Trail, Chester, MA 01011
  • 22 Lyon Hill Rd, Chester, MA 01011
    22 Lyon Hill Rd, Chester, MA 01011
    22 Lyon Hill Rd, Chester, MA 01011
    /38

    $349,900

    Open Sat 1PM - 2:30PM
    • 3 Beds
    • 2 Baths
    • 1,450 Sq Ft

    22 Lyon Hill Rd, Chester, MA 01011

    DISCOVER TRANQUIL COUNTRY LIVING on over 2 acres with this spacious, bright and airy ranch, just 25 minutes to Outlook Farm in Westhampton. A charming covered front porch welcomes you inside to sun-filled living space and an updated kitchen with granite counters, ample cabinetry, and modern finishes. Off the dining area, a giant screened-in porch offers the perfect spot for bug-free outdoor

    Jill Vincent-Lapan Canon Real Estate, Inc.

    22 Lyon Hill Rd, Chester, MA 01011
  • 1 Crane Rd, Chester, MA 01011
    1 Crane Rd, Chester, MA 01011
    1 Crane Rd, Chester, MA 01011
    /12

    $220,000

    • 4 Beds
    • 2 Baths
    • 2,151 Sq Ft

    1 Crane Rd, Chester, MA 01011

    Colonial style home featuring 8 rooms, 4 bedrooms and 2 bathrooms located on 6+ acre lot.

    Melissa Blondek Gallagher Real Estate

    1 Crane 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 $365,454.
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 01011, 01050, 01223, 01008 and 01027.
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 6.51%, your estimated principal and interest payment would be $1,640 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $70K 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 54 days on the market compared to the national average of 58 days. The median sale price for homes in Chester, MA over the last 12 months is $334,500, down 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$334,500
Median Single Family Sale Price
$329,000
Average Price Per Sq Ft
$201
Number of Homes for Sale
5
Last 12 months Home Sales
26
Months of Supply
2.30
Median List Price
$324,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-4%
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