13

Newest Homes for Sale in Chester, MA

Section Image Section Image
  • 50 Smith, Chester, MA 01011
    50 Smith, Chester, MA 01011
    /2

    $45,000

    $5K PRICE DROP
    • Land
    • 10 Acres
    • $4,500 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
  • 28 Hampden St, Chester, MA 01011
    28 Hampden St, Chester, MA 01011
    28 Hampden St, Chester, MA 01011
    /27

    $250,000

    $20K 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! 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
  • 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
  • Lot 35 Deer Run, Becket, MA 01223
    Lot 35 Deer Run, Becket, MA 01223
    Lot 35 Deer Run, Becket, MA 01223
    /11

    $15,000

    • Land
    • 3.56 Acres
    • $4,213 per Acre

    Lot 35 Deer Run, Becket, MA 01223

    Very private wooded lot at the end of the cul de sac in the Deer Haven community (HOA). Bargain priced estate sale, being sold as is. Buyers to do their own due diligence. No camping or RV use per town bylaws.

    Kim Bergland RED HORSE REAL ESTATE, LLC

    Lot 35 Deer Run, Becket, MA 01223
  • 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 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

    $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
  • 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

    $249,900

    $36K 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
Massachusetts Hampden County

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 $327,888.
How many homes have sold over the last 12 months in Chester, MA?
30 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 01243.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $296,750. If you put a 20% down payment of $59,400 and had a 30-year fixed mortgage with an interest rate of 6.66%, your estimated principal and interest payment would be $1,530 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $66K 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 $332,000, up 11% year-over-year. Homes in Chester sell in 72 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$332,000
Median Single Family Sale Price
$305,000
Median 2 Bedroom Sale Price
$305,000
Median 1 Bedroom Sale Price
$41,500
Average Price Per Sq Ft
$191
Number of Homes for Sale
5
Last 12 months Home Sales
30
Months of Supply
2.00
Median List Price
$296,750
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
11%
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