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Newest Homes for Sale in Chester, MA

Section Image Section Image
  • lot 3 Holcomb Rd, Chester, MA 01011
    lot 3 Holcomb Rd, Chester, MA 01011
    lot 3 Holcomb Rd, Chester, MA 01011
    /5

    $60,000

    • Land
    • 2.12 Acres
    • $28,302 per Acre

    lot 3 Holcomb Rd, Chester, MA 01011

    Open land. Prime 2-acre pasture, building lot with stone walls on a quiet gravel road. Property rear is bordered by protected conservation land, One of 4 lots available.

    James Adams Hilltown Real Estate by Adams Realty

    lot 3 Holcomb Rd, Chester, MA 01011
  • lot 2 Holcomb Rd, Chester, MA 01011
    lot 2 Holcomb Rd, Chester, MA 01011
    lot 2 Holcomb Rd, Chester, MA 01011
    /4

    $45,000

    • Land
    • 2.06 Acres
    • $21,845 per Acre

    lot 2 Holcomb Rd, Chester, MA 01011

    Prime 2 acre building lot with stone walls on a quiet gravel road. Property rear is bordered by protected conservation land , One of 4 lots available.

    James Adams Hilltown Real Estate by Adams Realty

    lot 2 Holcomb Rd, Chester, MA 01011
  • lot1 Holcomb Rd, Chester, MA 01011
    lot1 Holcomb Rd, Chester, MA 01011
    lot1 Holcomb Rd, Chester, MA 01011
    /3

    $45,000

    • Land
    • 2.03 Acres
    • $22,167 per Acre

    lot1 Holcomb Rd, Chester, MA 01011

    Prime 2 acre building lot with stone walls on a quiet gravel road. Property rear is bordered by protected conservation land , One of 4 lots available.

    James Adams Hilltown Real Estate by Adams Realty

    lot1 Holcomb Rd, Chester, MA 01011
  • lot 9-11 Skyline, Chester, MA 01011
    lot 9-11 Skyline, Chester, MA 01011
    lot 9-11 Skyline, Chester, MA 01011
    /3

    $79,000

    • Land
    • 21.24 Acres
    • $3,719 per Acre

    lot 9-11 Skyline, Chester, MA 01011

    21 acres of forest land on the Chester/ Middlefield line. The north boundary is the Middlefield line. There is also frontage on Lynes road, but that road is not maintained. There is a small brook on the property. Go direct

    James Adams Hilltown Real Estate by Adams Realty

    lot 9-11 Skyline, Chester, MA 01011
  • lot 4 Holcomb Rd, Chester, MA 01011
    lot 4 Holcomb Rd, Chester, MA 01011
    lot 4 Holcomb Rd, Chester, MA 01011
    /4

    $69,000

    • Land
    • 2.5 Acres
    • $27,600 per Acre

    lot 4 Holcomb Rd, Chester, MA 01011

    Prime 2-acre farmland pasture. This is a premium building lot with stone walls on a quiet gravel road. Property rear is bordered by protected conservation land, One of 4 lots available.

    James Adams Hilltown Real Estate by Adams Realty

    lot 4 Holcomb Rd, Chester, MA 01011
  • 91 Lynes Rd, Chester, MA 01011
    91 Lynes Rd, Chester, MA 01011
    91 Lynes Rd, Chester, MA 01011
    /3

    $50,000

    • Land
    • 3.47 Acres
    • $14,409 per Acre

    91 Lynes Rd, Chester, MA 01011

    Discover 3.47 acres of wooded land tucked along a tree-lined, unpaved road in Chester, known as the "Gem of the Valley." Chester offers a blend of small-town charm and outdoor recreation, from the Chester on Track festival and the Railway Museum to the Keystone Arch Bridges Trail and a vibrant local theatre community. Public records identify the parcel as residential (use code 130). If you’ve

    Agent Photo

    Cheryl Malandrinos

    HB Real Estate, LLC

    91 Lynes Rd, Chester, MA 01011
  • 95 Lynes Rd, Chester, MA 01011
    95 Lynes Rd, Chester, MA 01011
    95 Lynes Rd, Chester, MA 01011
    /3

    $50,000

    • Land
    • 3.54 Acres
    • $14,124 per Acre

    95 Lynes Rd, Chester, MA 01011

    Is this 3.54 acre lot shouting your name? Down an unpaved, tree-lined road lies this wooded lot awaiting its new owner. Looking for some small town charm? Chester is known as the "Gem of the Valley." It is home to a variety of activities and amenities, such as the Chester on Track festival, the Railway Museum, a longstanding theatre company, and the Keystone Arch Bridges Trail. Public records and

    Agent Photo

    Cheryl Malandrinos

    HB Real Estate, LLC

    95 Lynes Rd, Chester, MA 01011
  • 1 Crane Rd, Chester, MA 01011
    1 Crane Rd, Chester, MA 01011
    1 Crane Rd, Chester, MA 01011
    /12

    $210,000

    $10K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,151 Sq Ft

    1 Crane Rd, Chester, MA 01011

    Colonial style home featuring 8 rooms, 4 bedrooms and 2 bathrooms located on 6+ acre lot.

    Melissa Blondek Gallagher Real Estate

    1 Crane Rd, Chester, MA 01011
  • 6 Maple St, Chester, MA 01011
    6 Maple St, Chester, MA 01011
    6 Maple St, Chester, MA 01011
    /28

    $235,000

    Pre-Foreclosure
    • 6 Beds
    • 2 Baths
    • 4,132 Sq Ft

    6 Maple St, Chester, MA 01011

    This is an outstanding opportunity to buy at well below market value. Both units are in move in condition however a septic system will need to be installed at the buyer's expense. Each unit is very expansive with three bedrooms in each unit. Over 4,000 square feet of living area. Many updates including newer furnaces. This is a very smart investment for a cash buyer or a rehab type loan to remedy

    James Adams Hilltown Real Estate by Adams Realty

    6 Maple St, Chester, MA 01011
  • 147 Chipman Rd, Chester, MA 01011
    147 Chipman Rd, Chester, MA 01011
    147 Chipman Rd, Chester, MA 01011
    /42

    $450,000

    Open Sat 11AM - 12:30PM $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,068 Sq Ft

    147 Chipman Rd, Chester, MA 01011

    Welcome home to this peaceful & serene 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 w/ laundry, a

    Taylor Hildack Keller Williams Realty

    147 Chipman Rd, Chester, MA 01011
  • 56 Middlefield Rd, Chester, MA 01011
    56 Middlefield Rd, Chester, MA 01011
    56 Middlefield Rd, Chester, MA 01011
    /39

    $365,000

    $50K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 2,832 Sq Ft

    56 Middlefield Rd, Chester, MA 01011

    The price has improved! Don't miss out. 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

    Agent Photo

    Cynthia Gonzalez

    Executive Real Estate, Inc.

    56 Middlefield Rd, Chester, MA 01011
  • 254 Route 20, Chester, MA 01011
    254 Route 20, Chester, MA 01011
    254 Route 20, Chester, MA 01011
    /38

    $264,900

    $21K PRICE DROP
    • 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
  • 11 Taft Rd, Chester, MA 01011
    11 Taft Rd, Chester, MA 01011
    11 Taft Rd, Chester, MA 01011
    /23

    $225,000

    $25K PRICE DROP
    • 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
  • 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

    $5K PRICE DROP
    • 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
Massachusetts Hampden County Chester

Newest Listings for Sale in Chester, MA

Frequently Asked Questions

What is the average home price in Chester, MA?
Homes for sale in Chester, MA have an average home price of $350,297.
How many homes have sold over the last 12 months in Chester, MA?
29 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, 01223, 01008 and 01098.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $309,999. If you put a 20% down payment of $62,000 and had a 30-year fixed mortgage with an interest rate of 6.49%, your estimated principal and interest payment would be $1,570 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $67K 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 Wahconah Regional High School, Chester Elementary School and Gateway Regional High School. Browse all the schools in Chester, MA to learn more.

Home Prices in Chester, MA

The median home sale price in Chester, MA is $329,000, down 6% year-over-year. Homes in Chester sell in 52 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price
$329,000
Median Single Family Sale Price
$315,000
Median 2 Bedroom Sale Price
$329,000
Average Price Per Sq Ft
$194
Number of Homes for Sale
4
Last 12 months Home Sales
29
Months of Supply
1.70
Median List Price
$309,999
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-6%
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