7

Newest Homes for Sale in Chester, MA

Section Image Section Image
  • 22 Lyon Hill Rd, Chester, MA 01011
    22 Lyon Hill Rd, Chester, MA 01011
    22 Lyon Hill Rd, Chester, MA 01011
    /38

    $349,900

    Open Sat 1PM - 2:30PM
    • 3 Beds
    • 2 Baths
    • 1,450 Sq Ft

    22 Lyon Hill Rd, Chester, MA 01011

    DISCOVER TRANQUIL COUNTRY LIVING on nearly 4 acres with this spacious, bright and airy ranch, just 25 minutes to Outlook Farm in Westhampton. A charming covered front porch welcomes you inside to sun-filled living space and an updated kitchen with granite counters, ample cabinetry, and modern finishes. Off the dining area, a giant screened-in porch offers the perfect spot for bug-free outdoor

    Jill Vincent-Lapan Canon Real Estate, Inc.

    22 Lyon Hill Rd, Chester, MA 01011
  • 1 Crane Rd, Chester, MA 01011
    1 Crane Rd, Chester, MA 01011
    1 Crane Rd, Chester, MA 01011
    /12

    $220,000

    • 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
  • 504 Skyline Trail, Chester, MA 01011
    504 Skyline Trail, Chester, MA 01011
    504 Skyline Trail, Chester, MA 01011
    /19

    $578,900

    Open Sun 1PM - 2PM
    • 4 Beds
    • 2 Baths
    • 2,244 Sq Ft

    504 Skyline Trail, Chester, MA 01011

    Set along the scenic Skyline Trail, this fully renovated home offers refined finishes, abundant natural light, and a seamless open layout. A long, estate-style concrete approach creates a striking sense of arrival, leading into a thoughtfully updated interior featuring porcelain tile flooring, modern upgrades, and two fireplaces that add warmth and architectural character. A versatile finished

    Oleg Abramchuk First NationWide Realty Inc.

    504 Skyline Trail, 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
  • 56 Middlefield Rd, Chester, MA 01011
    56 Middlefield Rd, Chester, MA 01011
    56 Middlefield Rd, Chester, MA 01011
    /39

    $394,900

    $20K PRICE DROP
    • 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
  • 254 Route 20, Chester, MA 01011
    254 Route 20, Chester, MA 01011
    254 Route 20, Chester, MA 01011
    /38

    $269,900

    Open Sat 11AM - 12:30PM $16K 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
  • 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 $363,299.
How many homes have sold over the last 12 months in Chester, MA?
26 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 01027.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $332,400. If you put a 20% down payment of $66,500 and had a 30-year fixed mortgage with an interest rate of 6.53%, 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. 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 Trends in Chester, MA

On average, homes in Chester, MA sell after 54 days on the market compared to the national average of 58 days. The median sale price for homes in Chester, MA over the last 12 months is $334,500, down 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$334,500
Median Single Family Sale Price
$334,500
Average Price Per Sq Ft
$200
Number of Homes for Sale
4
Last 12 months Home Sales
26
Months of Supply
1.80
Median List Price
$332,400
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-4%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group