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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
    /4

    $40,000

    $10K PRICE DROP
    • Land
    • 3.54 Acres
    • $11,299 per Acre

    95 Lynes Rd, Chester, MA 01011

    Tucked down an unpaved, tree-lined road, this 3.54+/- acre wooded lot offers a pleasant setting with classic hilltown charm. Chester, known as the “Gem of the Valley,” is home to the Chester on Track festival, the Railway Museum, a longstanding theatre company, and the Keystone Arch Bridges Trail. Public records and a 2017 aerial image indicate two sheds on the property, though this has not been

    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
  • 23 Maple St, Chester, MA 01011
    23 Maple St, Chester, MA 01011
    23 Maple St, Chester, MA 01011
    /24

    $225,000

    • 2 Beds
    • 1 Bath
    • 1,652 Sq Ft

    23 Maple St, Chester, MA 01011

    Welcome home to your little slice of a rural countryside community. This property is situated on the west branch of the Westfield River in a quiet but convenient location. Enjoy your coffee on the porch and get lost in the sounds of nature. Inside you will find an open floor plan, a newer primary first floor bedroom, and three rooms upstairs with closets. This home is a hidden gem with tons of

    Keira Jackson Keller Williams Realty

    23 Maple St, 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
  • 93 Crane Rd, Chester, MA 01011
    93 Crane Rd, Chester, MA 01011
    93 Crane Rd, Chester, MA 01011
    /6

    $129,900

    • 1 Bath
    • 560 Sq Ft

    93 Crane Rd, Chester, MA 01011

    Escape to the scenic hills of Chester with this unique 5.2-acre property offering the opportunity to create your year-round country home. Two major infrastructure investments are already in place with the well and three bedroom septic system. Giving you the head start on your new home. The existing 560-square-foot cottage provides a comfortable retreat while you plan and develop your vision for

    Daniel James Piasecki Coldwell Banker Community REALTORS®

    93 Crane Rd, Chester, MA 01011
  • 254 Route 20, Chester, MA 01011
    254 Route 20, Chester, MA 01011
    254 Route 20, Chester, MA 01011
    /38

    $239,900

    $46K 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
  • 50 Smith, Chester, MA 01011
    50 Smith, Chester, MA 01011
    /2

    $40,000

    $10K PRICE DROP
    • Land
    • 10 Acres
    • $4,000 per Acre

    50 Smith, Chester, MA 01011

    10-Acre Land OpportunityBring your vision to this beautiful 10-acre parcel of land and imagine what could be created here. The sellers once had grand plans for this property, but life has changed, creating an exciting opportunity for someone else to bring those plans to life.The property offers the potential to recreate what was once here, with building limited to the footprint/use of the former

    Nicolle Serafino Keller Williams Realty

    50 Smith, 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

    $240,000

    $30K PRICE DROP
    • 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! Move in ready! This is truly a special home. 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

    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

    $150,000

    $70K 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
  • 0 Mica Mill Rd, Chester, MA 01011
    0 Mica Mill Rd, Chester, MA 01011
    /2

    $129,000

    • Land
    • 28 Acres
    • $4,607 per Acre

    0 Mica Mill Rd, Chester, MA 01011

    Opportunity to own 28.00 acres in Chester's rural hilltown setting. Located at 0 Mica Mill Rd, this vacant parcel is identified in town records as AR Agricultural Residential and offers a canvas for a future homesite or other potential use, subject to all required approvals. Enjoy a quiet western Massachusetts location with access to the Berkshires and Pioneer Valley region. Buyer and buyer's

    Jaquaine Coe The LGCY Group LLC

    0 Mica Mill Rd, Chester, MA 01011
Massachusetts Hampden County Chester

Real Estate & Homes for Sale in Chester, Chester

Chester, MA, MA Home Prices vs. Nearby Neighborhoods

Chester Huntington Russell Middlefield
Median Home Price
$299,499
$289,900
$374,900
$338,450
Median Sale Price
$337,500
+7% YoY
$285,000
-23% YoY
$336,000
-6% YoY
$349,500
-8% YoY
Avg. Price per Square Foot
$189
$209
$229
$304
Median Single Family Price
$298,000
$285,000
$429,950
$337,000
Total Active Listings
14 listings
6 listings
6 listings
6 listings
Market Conditions
2 Months of Supply
Seller's Market
3 Months of Supply
Seller's Market
5 Months of Supply
Balanced Market
8 Months of Supply
Buyer'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 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.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $299,499. If you put a 20% down payment of $59,900 and had a 30-year fixed mortgage with an interest rate of 7.03%, your estimated principal and interest payment would be $1,600 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $69K 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.
Are home prices dropping in Chester?
Yes, home prices in Chester are down 3% in the last 12 months.
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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