5

Chester, MA Homes for Sale with Garage

Section Image Section Image
  • 56 Middlefield Rd, Chester, MA 01011
    56 Middlefield Rd, Chester, MA 01011
    56 Middlefield Rd, Chester, MA 01011
    /39

    $389,900

    $25K 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

    $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
  • 147 Chipman Rd, Chester, MA 01011
    147 Chipman Rd, Chester, MA 01011
    147 Chipman Rd, Chester, MA 01011
    /40

    $460,000

    Open Sat 11AM - 12:30PM
    • 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! The main level features a spacious living rm & dining area w/ propane stove & sliders to a sunny deck, a kitchen w/ pantry closet, half bath w/ laundry, a first-floor office, & a primary bedroom w/ ensuite

    Taylor Hildack KELLER WILLIAMS REALTY

    147 Chipman 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

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

    $349,900

    • 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
Massachusetts Hampden County Chester

Homes for Sale with Garage in Chester, MA

Home Prices in Chester, MA

The median home sale price in Chester, MA is $334,500, down 4% year-over-year. Homes in Chester sell in 55 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$334,500
Median Single Family Sale Price
$340,000
Median 2 Bedroom Sale Price
$340,000
Average Price Per Sq Ft
$202
Number of Homes for Sale
5
Last 12 months Home Sales
26
Months of Supply
2.30
Median List Price
$344,900
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

In Chester, there are currently 5 homes for sale with a garage. Meeting the needs of buyers seeking secure parking and extra storage, these homes offer various garage options. Whether it's a property featuring a practical two-car garage or a larger residence with a sought-after three-car garage, these homes provide the convenience and flexibility desired by many homeowners. Additionally, some properties come with detached garages, offering ample space while ensuring privacy. Explore the selection of homes for sale with a garage in Chester, MA and find the perfect place to call 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