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Chester Homes for Sale

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  • 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

    $35,000

    • Land
    • 3.24 Acres
    • $10,802 per Acre

    0 Round Hill Rd Unit 73399828, Chester, MA 01011

    A 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
  • 274 Goss Hill Rd, Huntington, MA 01050
    274 Goss Hill Rd, Huntington, MA 01050
    274 Goss Hill Rd, Huntington, MA 01050
    /42

    $519,900

    • 3 Beds
    • 3 Baths
    • 2,644 Sq Ft

    274 Goss Hill Rd, Huntington, MA 01050

    Tucked just minutes off Route 112, this well-maintained 2,644 sq ft cedar-sided Colonial is located in Chester, with full services provided by the town of Huntington. Set on 4.25 private acres abutting state land, the property offers scenic views, a peaceful pond, and charming stone walls—creating a picturesque and tranquil setting. Inside, the spacious kitchen is ideal for entertaining, with

    Darcie Gasperini Taylor Agency

    274 Goss Hill Rd, Huntington, MA 01050
  • 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
  • 613 Skyline Trail, Chester, MA 01011
    613 Skyline Trail, Chester, MA 01011
    613 Skyline Trail, Chester, MA 01011
    /42

    $489,500

    • 3 Beds
    • 2 Baths
    • 2,012 Sq Ft

    613 Skyline Trail, Chester, MA 01011

    Complete privacy awaits you in this charming Cape-style home! Perfect for easy entertaining, the home features a spacious three-season lanai with a wet bar, a covered patio, a large level yard, vibrant flowering gardens, and raspberry and blueberry bushes — plus a barn for added versatility. Inside, the cozy living room with a wood stove opens seamlessly to the kitchen, which is outfitted with

    Denise DeSellier Berkshire Hathaway HomeServices Realty Professionals

    613 Skyline Trail, 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 13 Skyline Trail, Chester, MA 01011
    lot 13 Skyline Trail, Chester, MA 01011
    lot 13 Skyline Trail, Chester, MA 01011
    /11

    $47,000

    • Land
    • 7 Acres
    • $6,963 per Acre

    lot 13 Skyline Trail, Chester, MA 01011

    Wonderful level lot with perk test in hand. This flat lot has a survey and has been flagged. A wooded property with a year-round brook. The area has newer homes and is quite convenient to shopping and Berkshire attractions. If you're ready to build, then this lot is ready to go! 200 feet north of 698 Skyline trail

    James Adams Hilltown Real Estate by Adams Realty

    lot 13 Skyline Trail, Chester, MA 01011
  • lot 61 Skyline Trail, Chester, MA 01011
    lot 61 Skyline Trail, Chester, MA 01011
    lot 61 Skyline Trail, Chester, MA 01011
    /5

    $850,000

    • Land
    • 191 Acres
    • $4,450 per Acre

    lot 61 Skyline Trail, Chester, MA 01011

    Subdivision available. A 191-acre property with open land, forest and potential views. We have a plan dividing this property into 14 homesites. These lots would be spectacular with some lots having meadow, some wooded and some with potentially beautiful views. Subdivision needs town approval. The Holcomb Road lots may not be available.

    James Adams Hilltown Real Estate by Adams Realty

    lot 61 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 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 is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. 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.
Is Chester, MA a safe neighborhood?
Chester, MA is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $325,000. If you put a 20% down payment of $65,000 and had a 30-year fixed mortgage with an interest rate of 6.75%, your estimated principal and interest payment would be $1,690 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $72K 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 35 days on the market compared to the national average of 51 days. The median sale price for homes in Chester, MA over the last 12 months is $300,000, up 41% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$300,000
Median Single Family Sale Price
$350,000
Average Price Per Sq Ft
$200
Number of Homes for Sale
3
Last 12 months Home Sales
15
Months of Supply
2.40
Median List Price
$325,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
41%
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