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Chester, MA Houses for Sale

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  • 254 Route 20, Chester, MA 01011
    254 Route 20, Chester, MA 01011
    254 Route 20, Chester, MA 01011
    /38

    $285,900

    • 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
  • 7 William St, Chester, MA 01011
    7 William St, Chester, MA 01011
    7 William St, Chester, MA 01011
    /37

    $292,000

    • 3 Beds
    • 2 Baths
    • 1,912 Sq Ft

    7 William St, Chester, MA 01011

    Wow! Affordable three-bedroom, Two full bath Victorian style home set on a quiet street in Beautiful Chester. Pleasant mountain views from your wrap around porch. This home is immaculate with stunning kitchen, and an oversized living room. Hardwood floors on the first floor and a fabulous dining room. Walk up attic and a walk out basement. Great perennial gardens and so much more. Chester has so

    James Adams Hilltown Real Estate by Adams Realty

    7 William St, Chester, MA 01011
  • 11 Taft Rd, Chester, MA 01011
    11 Taft Rd, Chester, MA 01011
    11 Taft Rd, Chester, MA 01011
    /23

    $235,000

    • 2 Beds
    • 1 Bath
    • 1,076 Sq Ft

    11 Taft Rd, Chester, MA 01011

    This cedar sided bungalow in a peaceful setting offers an open floor plan, 5.61 acres of land, a private deck overlooking the beautiful yard w/ blueberry bushes, apple & pear trees. Kitchen w/appliances to stay. Cozy DR. Large open LR w/cathedral ceilings. First floor laundry. Full bath w/tub & shower. Potential for a half bath off the empty bedroom (it was a half bath at one time) Abbott Brook

    Victoria Minella-Sena Berkshire Hathaway HomeServices Realty Professionals

    11 Taft Rd, Chester, MA 01011
  • 76 Hampden St, Chester, MA 01011
    76 Hampden St, Chester, MA 01011
    76 Hampden St, Chester, MA 01011
    /27

    $260,000

    • 3 Beds
    • 1 Bath
    • 1,048 Sq Ft

    76 Hampden St, Chester, MA 01011

    Country Charm Meets Comfort and Nature-Outdoor living at its finest! Nestled on a generous double lot, this delightful country home offers an enchanting retreat just minutes from the heart of Westfield. Surrounded by mature landscaping, fruit trees, and a lush forest brimming with wildlife, it’s a nature lover’s dream come true. Step onto the enclosed side porch, relax as birds sing and deer

    Stacey Silvia Lock and Key Realty Inc.

    76 Hampden St, Chester, MA 01011
  • 73 Ingell Rd, Chester, MA 01011
    73 Ingell Rd, Chester, MA 01011
    73 Ingell Rd, Chester, MA 01011
    /19

    $425,000

    • 2 Beds
    • 1 Bath
    • 1,350 Sq Ft

    73 Ingell Rd, Chester, MA 01011

    A diamond in the rough! Located on a country road with expansive views. Rustic ranch-style farmhouse with a western flair. Notable improvements in the last 10 years roof/windows/skylight/furnace and updates to the electric. Generous open floor plan for the kitchen and living room with peaceful outside views to expansive skies. Second floor heated studio with approximately 385sf, potential to

    Debra Petrovsky Donovan Real Estate

    73 Ingell Rd, Chester, MA 01011
Massachusetts Hampden County Chester

Houses 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

Home Trends in Chester, MA

On average, homes in Chester, MA sell after 62 days on the market compared to the national average of 52 days. The median sale price for homes in Chester, MA over the last 12 months is $325,000, up 43% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$325,000
Median Single Family Sale Price
$300,000
Average Price Per Sq Ft
$196
Number of Homes for Sale
5
Last 12 months Home Sales
18
Months of Supply
3.30
Median List Price
$304,900
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
43%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 5 houses for sale, offering an array of options for potential buyers. With houses priced between $235,000 to $425,000, there's a range to accomodate every budget. As of September, 2025 the median home price in Chester is $304,900, while the average sale price is $343,311, offering insights into the local housing market. On average, houses spend 62 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Chester, MA and find the perfect place to call home.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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