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Chester Homes for Sale

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

    $294,500 Open Sun 11AM - 1PM

    • 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
  • 0 N Chester Rd, Chester, MA 01011
    0 N Chester Rd, Chester, MA 01011
    0 N Chester Rd, Chester, MA 01011
    /20

    $19,497

    • Land
    • 5.00 Acres
    • $3,899 per Acre

    0 N Chester Rd, Chester, MA 01011

    Here's your opportunity to own an amazing 5-acre property nestled in the heart of Chester, MA, in Hampden County. Located off Chester Rd, the parcel is considered landlocked, while a paper road provides recorded access, there is currently no vehicle access, and the land is being sold as-is. A plat map is available for review. Set on a gently sloping hillside overlooking a small river, the

    Derek Greene The Greene Realty Group

    0 N Chester Rd, Chester, MA 01011
  • 0 Round Hill Rd Unit 73399828, Chester, MA 01011
    0 Round Hill Rd Unit 73399828, Chester, MA 01011
    0 Round Hill Rd Unit 73399828, Chester, MA 01011
    /6

    $28,000

    • Land
    • 3.24 Acres
    • $8,642 per Acre

    0 Round Hill Rd Unit 73399828, Chester, MA 01011

    Price drop on this great get away with over three acres. There is a recent perk test, if you want to build on the land. This property comes with a newer camper. Walking distance to the hiking trails of the expansive Chester State Forest. The road does not have electric at this time, so off grid living is the way to go. 200 feet north of Smithy Road.

    James Adams Hilltown Real Estate by Adams Realty

    0 Round Hill Rd Unit 73399828, Chester, MA 01011
  • 12 Riverfront St, Chester, MA 01011
    12 Riverfront St, Chester, MA 01011
    12 Riverfront St, Chester, MA 01011
    /36

    $339,900

    • 2 Beds
    • 1 Bath
    • 1,450 Sq Ft

    12 Riverfront St, Chester, MA 01011

    Charming riverfront home in historic Chester, close to all main attractions in Berkshire County and the college towns of Amherst and Northampton. The house has been lovingly maintained as a short-term rental since 2018, with excellent occupancy rates for visitors looking for a quiet getaway with a small town atmosphere while also central to all of Western Massachusetts. Single floor living,

    Stephen Daoust STONE HOUSE PROPERTIES, LLC

    12 Riverfront St, Chester, MA 01011
  • 31 Skyline Trail, Chester, MA 01011
    31 Skyline Trail, Chester, MA 01011
    31 Skyline Trail, Chester, MA 01011
    /24

    $299,800

    • Land
    • 70 Acres
    • $4,283 per Acre

    31 Skyline Trail, Chester, MA 01011

    This 70-acre parcel in Chester & Huntington, MA offers a rare opportunity for privacy and natural beauty. There is a mix of wooded areas and a beautiful stream with a magnificent waterfall. This land is perfect for a private estate, recreational use, or development. Zoned for residential use, it provides flexibility for various projects, including potential subdivision (subject to local

    Brenda Cuoco Cuoco & Co. Real Estate

    31 Skyline Trail, Chester, MA 01011
  • lot 3 Skyline Trail, Chester, MA 01011
    lot 3 Skyline Trail, Chester, MA 01011
    lot 3 Skyline Trail, Chester, MA 01011
    /4

    $50,000

    • Land
    • 3.00 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
  • 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 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
Massachusetts Hampden County Chester Chester

Real Estate & Homes for Sale in Chester, Chester

Frequently Asked Questions Why Live in Chester

Is Chester a good place to live?
Chester is a good place to live. Chester is considered very car-dependent. Chester has 2 parks for recreational activities. It has a median age of 48. The average household income is $87,362 which is below the national average. College graduates make up 20.7% of residents. A majority of residents in Chester are home owners, with 16.1% of residents renting and 83.9% of residents owning their home. A local real estate agent serving Chester can help you decide if this neighborhood is the right one for you. Learn more on our Chester neighborhood guide.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $299,900. If you put a 20% down payment of $60,000 and had a 30-year fixed mortgage with an interest rate of 6.5%, your estimated principal and interest payment would be $1,520 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $65K a year to afford the median home price in Chester. The average household income in Chester is $87K.
What are the best public schools in Chester?
The best public schools that serve Chester are:
What are the most popular zip codes in Chester, Chester, MA?
The most popular zip codes in Chester, Chester, MA include 01011, 01050, 01243, 01223 and 01008.
Learn more about living in Chester

Home Trends in Chester, MA

On average, homes in Chester, MA sell after 42 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 $300,000, up 33% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$300,000
Median Single Family Sale Price
$300,000
Average Price Per Sq Ft
$202
Number of Homes for Sale
5
Last 12 months Home Sales
15
Months of Supply
4.00
Median List Price
$299,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
33%
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