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Chester, MA Homes for Sale

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  • 45 Middlefield Rd, Chester, MA 01011
    45 Middlefield Rd, Chester, MA 01011
    45 Middlefield Rd, Chester, MA 01011
    /39

    $241,500

    • 7 Beds
    • 2 Baths
    • 3,058 Sq Ft

    45 Middlefield Rd, Chester, MA 01011

    Large Side-by-Side Duplex – Great Investment Opportunity! This spacious duplex offers a fantastic investment or owner occupied opportunity, each unit featuring generous layouts and separate utilities and propane heat. Situated on a nice lot with a large backyard, dog kennel, and space for a garden, this property provides both comfort and versatility. Left Unit: 3 bedrooms upstairs, plus an

    Joy Salvini RE/MAX Compass

    45 Middlefield Rd, 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
  • 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

Real Estate & Homes for Sale in Chester, MA

Why Live in Chester

Chester, a hillside community in Massachusetts, offers a secluded and tranquil living environment about 30 miles west of Springfield. This sparsely populated area is ideal for those seeking privacy, with homes surrounded by thick forests that showcase vivid fall colors. The neighborhood features a mix of architectural styles, including Colonials, Cape Cods, and contemporary homes, many with decks or porches to enjoy the peaceful surroundings. Chester is known for its thriving theater scene, with the Chester Theatre Company producing highly regarded summer shows. The community also hosts cultural events like the Littleville Fair, featuring truck pulls, raffles, and square dancing. Outdoor recreation is abundant, with Chester-Blandford State Forest offering hiking, snowmobiling, mountain biking, and more. The John J. Kelly Wildlife Management Area is perfect for birdwatching, while Chester Town Park and Hampden Street Park provide spaces for sports and walking. Although Chester has a modest selection of local shops and dining options, residents often drive 20 miles to Westfield for major grocery hauls and additional amenities. Route 20 is the main road through Chester, connecting to Interstate 90 and leading to Springfield. Bradley International Airport is 40 miles away, and Baystate Noble Hospital is a 30-minute drive.
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 $380,300.
How many homes have sold over the last 12 months in Chester, MA?
6 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 01201, 01085, 01040, 01223 and 01089.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $362,450. If you put a 20% down payment of $72,500 and had a 30-year fixed mortgage with an interest rate of 6.77%, your estimated principal and interest payment would be $1,880 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $81K a year to afford the median home price in Chester.
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 68 days on the market compared to the national average of 50 days. The median sale price for homes in Chester, MA over the last 12 months is $297,500, up 32% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$297,500
Median Single Family Sale Price
$357,500
Average Price Per Sq Ft
$204
Number of Homes for Sale
1
Last 12 months Home Sales
6
Months of Supply
2.00
Median List Price
$362,450
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
32%
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