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Chester Homes for Sale

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  • 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
  • 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
  • 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
  • 254 Route 20, Chester, MA 01011
    254 Route 20, Chester, MA 01011
    254 Route 20, Chester, MA 01011
    /38

    $259,900

    $26K 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
  • 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
  • 166 Route 20, Chester, MA 01011
    166 Route 20, Chester, MA 01011
    166 Route 20, Chester, MA 01011
    /12

    $100,000

    • 2 Beds
    • 1.5 Baths
    • 1,328 Sq Ft

    166 Route 20, Chester, MA 01011

    Investors take note of the potential offered by this charming colonial home. Property is being sold as-is. The seller prefers a 60-day closing to allow sufficient time for removal of personal items from the house, yard, and barn. Title V has failed and will be the buyer’s responsibility. The home features partially updated plumbing and electrical systems, including an electrical panel and hot

    Thomas Despard Nexthome Elite Realty

    166 Route 20, Chester, MA 01011
  • 28 Hampden St, Chester, MA 01011
    28 Hampden St, Chester, MA 01011
    28 Hampden St, Chester, MA 01011
    /27

    $269,900

    • 2 Beds
    • 1 Bath
    • 734 Sq Ft

    28 Hampden St, Chester, MA 01011

    Absolutely charming and lovingly maintained home across the road from Walker Brook! Enjoy the tranquil sounds of the running water, cool off on a hot summer day or cast out a line and enjoy a vacation right at home. Relaxing wrap around deck to enjoy your peaceful surroundings and seasonal views. An amazing sun room that provides for more space to take in the nature around you, even from inside!

    Victoria Minella-Sena Berkshire Hathaway HomeServices Realty Professionals

    28 Hampden St, Chester, MA 01011
  • 1 Crane Rd, Chester, MA 01011
    1 Crane Rd, Chester, MA 01011
    1 Crane Rd, Chester, MA 01011
    /12

    $185,000

    $35K 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
  • 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
Massachusetts Hampden County Chester

Real Estate & Homes for Sale in Chester, Chester

Chester Home Prices vs. Nearby MA, MA Neighborhoods

Chester Huntington Russell Worthington
Median Home Price
$319,500
$285,000
$412,400
$390,000
Median Sale Price
$340,000
+13% YoY
$265,000
-30% YoY
$352,155
$375,050
-4% YoY
Median Single Family Price
$315,000
$265,000
$427,495
$375,050
Total Active Listings
3 listings
2 listings
4 listings
7 listings
Market Conditions
1 Month of Supply
Seller's Market
1 Month of Supply
Seller's Market
4 Months of Supply
Balanced Market
3 Months of Supply
Seller's Market

Frequently Asked Questions Why Live in Chester

Is Chester a good place to live?
Chester is a good place to live. Chester is considered somewhat bikeable. 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% of residents renting and 84% 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 $319,500. If you put a 20% down payment of $63,900 and had a 30-year fixed mortgage with an interest rate of 6.69%, your estimated principal and interest payment would be $1,650 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $71K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator. 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, 01223, 01008 and 01243.
What are the most popular neighborhoods near Chester, Chester, MA?
The most popular neighborhood near Chester, Chester, MA is Florence.
Learn more about living in Chester
How to Buy a Home How to Finance a Home How to Sell a Home

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