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Chester, MA Homes for Sale

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  • /39

    $414,999

    • 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
  • /32

    $374,900 Open Sat 11AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 1,768 Sq Ft

    654 Skyline Trail, Chester, MA 01011

    NESTLED ON ALMOST 4 ACRES, this newly minted reproduction colonial presents an attractive example of fine country living. The kitchen is professionally designed to be a central gathering place, featuring a large 4 stool island offering ample space for good conversation and meal preparation. The exquisite quartz countertops provide a touch of elegance and durability, complemented by shaker

    Paul Tourville Canon Real Estate, Inc.

    654 Skyline Trail, Chester, MA 01011
  • /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
  • /42

    $469,900

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

    147 Chipman Rd, Chester, MA 01011

    Welcome home to this 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 with laundry, a first-floor office, & a

    Taylor Hildack Keller Williams Realty

    147 Chipman Rd, Chester, MA 01011
  • /24

    $299,000

    • 2 Beds
    • 1.5 Baths
    • 1,896 Sq Ft

    67 Middlefield Rd, Chester, MA 01011

    Charming R-Zoned Property on 3 Cleared Acres with Barn - Chester, MA Set on 3 cleared acres in the peaceful town of Chester, this Single-Family Residential property offers space, privacy, and flexibility with R zoning. The home features 1,896 square feet of living space, including 2 bedrooms and 2 full baths, making it ideal for year-round living or a country retreat. Key systems are in good

    Alex King Lock and Key Realty, Inc

    67 Middlefield Rd, Chester, MA 01011
  • /38

    $279,500

    • 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
  • /23

    $234,900

    • 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
  • /4

    $50,000

    • Land
    • 3 Acres
    • $16,667 per Acre

    lot 3 Skyline Trail, Chester, MA 01011

    A great 3-acre parcel on a paved road with stone walls. Lightly forested and flat. This is a relatively easy building site for your new home. Land is just north of 590 Skyline trail.

    James Adams Hilltown Real Estate by Adams Realty

    lot 3 Skyline Trail, Chester, MA 01011
  • /18

    $578,900

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

    506 Skyline Trail, Chester, MA 01011

    Set along the scenic Skyline Trail, this fully renovated home offers refined finishes, abundant natural light, and an elegant open layout. A long, estate-style concrete approach creates a grand sense of arrival, leading to a beautifully updated interior with porcelain tile floors, modern updates, and two fireplaces that add warmth and character. The finished bonus space just off the main living

    Oleg Abramchuk First NationWide Realty Inc.

    506 Skyline Trail, Chester, MA 01011
  • /30

    $269,000

    • 4 Beds
    • 2 Baths
    • 3,864 Sq Ft

    4 Maple St, Chester, MA 01011

    Spacious two-family property located in desirable Hampden County. This 3,864 sq ft multi-family offers a total of 6 bedrooms and 2 full bathrooms across two units. Features include ample off-street parking and generous living space, making it ideal for owner-occupants or investors alike. Conveniently located near local amenities, schools, and major routes.

    Adam Devine Dorrance Realty LLC

    4 Maple St, Chester, MA 01011

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.

Frequently Asked Questions

What is the average home price in Chester, MA?
Homes for sale in Chester, MA have an average home price of $372,769.
How many homes have sold over the last 12 months in Chester, MA?
19 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, 01243, 01223 and 01098.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $299,949. If you put a 20% down payment of $60,000 and had a 30-year fixed mortgage with an interest rate of 6.06%, your estimated principal and interest payment would be $1,450 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $62K 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 Chester Elementary School, Wahconah Regional High School and Gateway Regional High School. Browse all the schools in Chester, MA to learn more.

Home Trends in Chester, MA

Housing Trends

Median Sale Price
$300,000
Median Single Family Sale Price
$299,900
Average Price Per Sq Ft
$212
Number of Homes for Sale
6
Last 12 months Home Sales
19
Months of Supply
3.80
Median List Price
$299,949
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
0%
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