977

Chester, MA Homes

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  • /39

    $404,900

    • 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
  • /26

    $270,000 Sold Nov 07, 2025

    76 Hampden St, Chester, MA 01011

    • 3 Beds
    • 1 Bath
    • 1,048 Sq Ft
    • Built 1880

    Last Sold Summary

    • 4% Above List Price
    • $258/SF
    • 61 Days On Market

    Current Estimated Value $263,538

    Last Listing Agent Stacey Silvia Lock and Key Realty Inc.

    76 Hampden St, Chester, MA 01011
    • /25

      Est $316,742 Not Listed For Sale

      143 Chipman Rd, Chester, MA 01011

      • 2 Beds
      • 2 Baths
      • 1,486 Sq Ft
      • Built 1988
      143 Chipman Rd, Chester, MA 01011

      Last Sold Summary

      • 10% Above List Price
      • $194/SF
      • 113 Days On Market

      Last Sold Price $288,700

      Last Listing Agent Zachary DeCaro Property Works New England

  • /7

    $75,000

    • 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
  • /42

    $340,000 Sold Dec 30, 2025

    689 Skyline Trail, Chester, MA 01011

    • 2 Beds
    • 1 Bath
    • 1,360 Sq Ft
    • Built 1987

    Last Sold Summary

    • 5% Above List Price
    • $250/SF
    • 14 Days On Market

    Current Estimated Value $337,598

    Last Listing Agent Kelley And Katzer Team Kelley & Katzer Real Estate, LLC

    689 Skyline Trail, Chester, MA 01011
    • /42

      Not Listed For Sale

      166 Bromley Rd, Chester, MA 01011

      • 5 Beds
      • 3 Baths
      • 2,094 Sq Ft
      • Built 1996
      166 Bromley Rd, Chester, MA 01011

      Last Sold Summary

      • $213/SF
      • 79 Days On Market

      Last Sold Price $445,000

      Last Listing Agent Taylor Hildack Keller Williams Realty

  • /23

    $225,000 Pending

    • 2 Beds
    • 1 Bath
    • 1,076 Sq Ft

    11 Taft Rd, Chester, MA 01011

    This cedar sided bungalow in a peaceful setting offers an open floor plan, 5.61 acres of land, a private deck overlooking the beautiful yard w/ blueberry bushes, apple & pear trees. Kitchen w/appliances to stay. Cozy DR. Large open LR w/cathedral ceilings. First floor laundry. Full bath w/tub & shower. Potential for a half bath off the empty bedroom (it was a half bath at one time) Abbott Brook

    Victoria Minella-Sena Berkshire Hathaway HomeServices Realty Professionals

    11 Taft Rd, Chester, MA 01011
  • /42

    $440,000 Sold Apr 30, 2025

    424 Route 20, Chester, MA 01011

    • 4 Beds
    • 2.5 Baths
    • 2,165 Sq Ft
    • Built 1986

    Last Sold Summary

    • 4% Above List Price
    • $203/SF
    • 4 Days On Market

    Current Estimated Value $438,009

    Last Listing Agent Angela Accorsi Coldwell Banker Realty - Western MA

    424 Route 20, Chester, MA 01011
    • /21

      Est $48,786 Not Listed For Sale

      67 Crane Rd, Chester, MA 01011

      67 Crane Rd, Chester, MA 01011

      Last Sold Summary

      • 6% Above List Price
      • 8 Days On Market

      Last Sold Price $46,000

      Last Listing Agent Jennifer Wilson Berkshire Hathaway HomeServices Realty Professionals

  • /38

    $279,500 Open Sat 12PM - 1:30PM

    • 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
  • /40

    $250,000 Sold Jul 18, 2025

    300 Middlefield Rd, Chester, MA 01011

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 2004

    Last Sold Summary

    • 9% Below List Price
    • $217/SF
    • 14 Days On Market

    Current Estimated Value $272,316

    Last Listing Agent Nicolle Serafino Keller Williams Realty

    300 Middlefield Rd, Chester, MA 01011
    • /5

      Not Listed For Sale

      0 Abbott Hill Rd, Chester, MA 01011

      0 Abbott Hill Rd, Chester, MA 01011

      Last Sold Summary

      • 305 Days On Market

      Last Sold Price $30,000

      Last Listing Agent Joy Salvini RE/MAX

  • /23

    $219,000

    • 2 Beds
    • 1 Bath
    • 860 Sq Ft

    187 Route 20, Chester, MA 01011

    Charming 2-bedroom, 1-bath home tucked away in the peaceful Hill Towns, offering comfort, character, and a scenic natural setting. A beautiful stream runs along the rear of the property, and the small, manageable lot makes upkeep easy while still providing room to enjoy the outdoors. Inside, the home features bright, welcoming spaces ideal for simple, low-maintenance living. Whether you’re

    Timothy Coughlen Park Square Realty

    187 Route 20, Chester, MA 01011
  • /32

    $380,000 Sold Mar 19, 2026

    654 Skyline Trail, Chester, MA 01011

    • 3 Beds
    • 2.5 Baths
    • 1,768 Sq Ft
    • Built 2022

    Last Sold Summary

    • 1% Above List Price
    • $215/SF
    • 9 Days On Market

    Current Estimated Value $386,803

    Last Listing Agent Paul Tourville Canon Real Estate, Inc.

    654 Skyline Trail, Chester, MA 01011
    • /42

      Est $412,622 Not Listed For Sale

      147 Chipman Rd, Chester, MA 01011

      • 3 Beds
      • 2.5 Baths
      • 2,068 Sq Ft
      • Built 2006
      147 Chipman Rd, Chester, MA 01011

      Last Sold Summary

      • 9% Above List Price
      • $184/SF
      • 167 Days On Market

      Last Sold Price $380,000

      Last Listing Agent Kim Bergland RED HORSE REAL ESTATE, LLC

  • /36

    $339,900 Under Contract

    • 2 Beds
    • 1 Bath
    • 1,450 Sq Ft

    12 Riverfront St, Chester, MA 01011

    Charming riverfront home in historic Chester, close to all main attractions in Berkshire County and the college towns of Amherst and Northampton. The house has been lovingly maintained as a short-term rental since 2018, with excellent occupancy rates for visitors looking for a quiet getaway with a small town atmosphere while also central to all of Western Massachusetts. Single floor living,

    Stephen Daoust STONE HOUSE PROPERTIES, LLC

    12 Riverfront St, Chester, MA 01011
  • /39

    $233,000 Sold Aug 14, 2025

    45 Middlefield Rd, Chester, MA 01011

    • 7 Beds
    • 2 Baths
    • 3,058 Sq Ft
    • Built 1900

    Last Sold Summary

    • 4% Below List Price
    • $76/SF
    • 41 Days On Market

    Current Estimated Value $236,177

    Last Listing Agent Joy Salvini RE/MAX Compass

    45 Middlefield Rd, Chester, MA 01011
    • /18

      Est $269,618 Not Listed For Sale

      110 Old State Hwy, Chester, MA 01011

      • 2 Beds
      • 1 Bath
      • 1,509 Sq Ft
      • Built 1940
      110 Old State Hwy, Chester, MA 01011

      Last Sold Summary

      • 20% Above List Price
      • $149/SF
      • 8 Days On Market

      Last Sold Price $225,000

      Last Listing Agent Aimee Tompkins Park Square Realty

  • /24

    $494,000 Pending

    • 4 Beds
    • 2 Baths
    • 2,160 Sq Ft

    279 Goss Hill Rd, Huntington, MA 01050

    Country Living at its best! Discover the perfect blend of space, comfort and opportunity with this large 4-bedroom, 2-bath home on 10 acres (consisting of two 5-acre lots). The welcoming layout includes a first floor bedroom and a convenient first floor laundry, making daily living easy and accessible. The great room boasts cathedral ceilings, creating an open and airy feel, perfect for

    Linda Webster COLDWELL BANKER COMMUNITY REALTORS

    279 Goss Hill Rd, Huntington, MA 01050
  • /23

    $305,000 Sold Mar 25, 2026

    67 Middlefield Rd, Chester, MA 01011

    • 2 Beds
    • 1.5 Baths
    • 1,896 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Above List Price
    • $161/SF
    • 26 Days On Market

    Current Estimated Value $294,534

    Last Listing Agent Alexander King Lock and Key Realty Inc.

    67 Middlefield Rd, Chester, MA 01011
    • /10

      Est $150,546 Not Listed For Sale

      664 Route 20, Chester, MA 01011

      • 6 Beds
      • 2 Baths
      • 2,400 Sq Ft
      • Built 1930
      664 Route 20, Chester, MA 01011

      Last Sold Summary

      • 120% Above List Price
      • $29/SF
      • 90 Days On Market

      Last Sold Price $68,500

      Last Listing Agent Xian Dole Premier Realty Group-Hadley

  • /2

    $365,000 Sold Feb 16, 2026

    11 Campbell Rd, Chester, MA 01011

    • 3 Beds
    • 1.5 Baths
    • 1,792 Sq Ft
    • Built 1990

    Last Sold Summary

    • $204/SF
    • 86 Days On Market

    Current Estimated Value $366,204

    Last Listing Agent Comparable Listing COMPARABLE LISTING ONLY

    11 Campbell Rd, Chester, MA 01011
    • /26

      Est $255,211 Not Listed For Sale

      396 Route 20, Chester, MA 01011

      • 2 Beds
      • 1 Bath
      • 1,156 Sq Ft
      • Built 1957
      396 Route 20, Chester, MA 01011

      Last Sold Summary

      • 6% Above List Price
      • $208/SF
      • 47 Days On Market

      Last Sold Price $240,000

      Last Listing Agent Maureen Borg Delap Real Estate LLC

  • /11

    $40,000 Sold Sep 11, 2025

    lot 13 Skyline Trail, Chester, MA 01011

    • Land
    • 6.75 Acres
    • $5,926 per Acre

    Last Sold Summary

    • 18% Below List Price
    • 166 Days On Market

    Last Listing Agent James Adams Hilltown Real Estate by Adams Realty

    lot 13 Skyline Trail, Chester, MA 01011
    • /29

      Est $247,870 Not Listed For Sale

      54 Route 20, Chester, MA 01011

      • 3 Beds
      • 2 Baths
      • 1,411 Sq Ft
      • Built 1875
      54 Route 20, Chester, MA 01011

      Last Sold Summary

      • 2% Above List Price
      • $172/SF
      • 116 Days On Market

      Last Sold Price $242,000

      Last Listing Agent Susan Deacon RE/MAX

  • /40

    $380,000 Sold Nov 26, 2025

    120 Fisk Rd, Worthington, MA 01098

    • 3 Beds
    • 1.5 Baths
    • 1,872 Sq Ft
    • Built 1952

    Last Sold Summary

    • $203/SF
    • 4 Days On Market

    Current Estimated Value $376,965

    Last Listing Agent Kylene Canon Canon Real Estate, Inc.

    120 Fisk Rd, Worthington, MA 01098
    • /34

      Est $386,704 Not Listed For Sale

      85 Lyman Rd, Chester, MA 01011

      • 3 Beds
      • 1 Bath
      • 1,440 Sq Ft
      • Built 1978
      85 Lyman Rd, Chester, MA 01011

      Last Sold Summary

      • 7% Below List Price
      • $288/SF
      • 3 Days On Market

      Last Sold Price $415,000

      Last Listing Agent Heather Witalisz Siegel Witalisz & Associates, Inc.

  • /42

    $489,500 Sold Sep 05, 2025

    613 Skyline Trail, Chester, MA 01011

    • 3 Beds
    • 2 Baths
    • 2,012 Sq Ft
    • Built 1989

    Last Sold Summary

    • 7% Below List Price
    • $243/SF
    • 98 Days On Market

    Current Estimated Value $472,982

    Last Listing Agent Denise DeSellier Berkshire Hathaway HomeServices Realty Professionals

    613 Skyline Trail, Chester, MA 01011
    • /34

      Est $304,949 Not Listed For Sale

      40 Holcomb Rd, Chester, MA 01011

      • 3 Beds
      • 2 Baths
      • 2,236 Sq Ft
      • Built 1769
      40 Holcomb Rd, Chester, MA 01011

      Last Sold Summary

      • 2% Above List Price
      • $134/SF
      • 32 Days On Market

      Last Sold Price $300,000

      Last Listing Agent Kelsey Thompson Team Lock and Key Realty Inc.

  • /42

    $315,000 Sold Sep 15, 2025

    9 William St, Chester, MA 01011

    • 3 Beds
    • 1 Bath
    • 1,458 Sq Ft
    • Built 1947

    Last Sold Summary

    • 9% Above List Price
    • $216/SF
    • 4 Days On Market

    Current Estimated Value $310,513

    Last Listing Agent Adam Lajeunesse Real Broker MA, LLC

    9 William St, Chester, MA 01011
    • /54

      Est $485,343 Not Listed For Sale

      78 Lyon Hill Rd, Chester, MA 01011

      • 3 Beds
      • 2.5 Baths
      • 2,130 Sq Ft
      • Built 1982
      78 Lyon Hill Rd, Chester, MA 01011

      Last Sold Summary

      • 7% Below List Price
      • $244/SF
      • 7 Days On Market

      Last Sold Price $520,000

      Last Listing Agent Tanya LeRose THE KINDERHOOK GROUP

  • /22

    $27,500 Sold Feb 12, 2026

    171 Prospect St, Chester, MA 01011

    • 5 Beds
    • 1.5 Baths
    • 2,322 Sq Ft
    • Built 1900

    Last Sold Summary

    • 44% Below List Price
    • $12/SF
    • 12 Days On Market

    Current Estimated Value $227,667

    Last Listing Agent Vadim Tulchinsky Witman Properties, Inc.

    171 Prospect St, Chester, MA 01011
    • /38

      Est $436,494 Not Listed For Sale

      36 Lyon Hill Rd, Chester, MA 01011

      • 3 Beds
      • 1.5 Baths
      • 2,144 Sq Ft
      • Built 2007
      36 Lyon Hill Rd, Chester, MA 01011

      Last Sold Summary

      • 2% Above List Price
      • $201/SF
      • 6 Days On Market

      Last Sold Price $430,000

      Last Listing Agent Jill Vincent-Lapan Canon Real Estate, Inc.

  • /5

    $558,350 Sold Oct 16, 2025

    lot 61 Skyline Trail, Chester, MA 01011

    • Land
    • 191 Acres
    • $2,923 per Acre

    Last Sold Summary

    • 34% Below List Price
    • 252 Days On Market

    Last Listing Agent James Adams Hilltown Real Estate by Adams Realty

    lot 61 Skyline Trail, Chester, MA 01011
    • /31

      Not Listed For Sale

      499 Skyline Trail, Chester, MA 01011

      • 3 Beds
      • 2 Baths
      • 3,844 Sq Ft
      • Built 1980
      499 Skyline Trail, Chester, MA 01011

      Last Sold Summary

      • $127/SF
      • 26 Days On Market

      Last Sold Price $487,000

      Last Listing Agent Claire Kenna Coldwell Banker Realty - Western MA

  • /41

    $299,900 Sold Aug 21, 2025

    20 William St, Chester, MA 01011

    • 3 Beds
    • 1.5 Baths
    • 2,570 Sq Ft
    • Built 1880

    Last Sold Summary

    • $117/SF
    • 5 Days On Market

    Current Estimated Value $307,342

    Last Listing Agent Tammy Weidhaas Today Real Estate, Inc.

    20 William St, Chester, MA 01011
    • /20

      Est $249,425 Not Listed For Sale

      115 Lyon Hill Rd, Chester, MA 01011

      • 4 Beds
      • Built 1960
      115 Lyon Hill Rd, Chester, MA 01011

      Last Sold Summary

      • 251% Above List Price
      • $26/SF
      • 3 Days On Market

      Last Sold Price $71,000

      Last Listing Agent Derek Greene The Greene Realty Group

  • /19

    $340,000 Sold Jan 23, 2026

    73 Ingell Rd, Chester, MA 01011

    • 2 Beds
    • 1 Bath
    • 1,350 Sq Ft
    • Built 1973

    Last Sold Summary

    • 20% Below List Price
    • $252/SF
    • 123 Days On Market

    Current Estimated Value $357,728

    Last Listing Agent Debra Petrovsky Donovan Real Estate

    73 Ingell Rd, Chester, MA 01011
    • /36

      Est $517,605 Not Listed For Sale

      674 Skyline Trail, Chester, MA 01011

      • 4 Beds
      • 2.5 Baths
      • 2,352 Sq Ft
      • Built 2007
      674 Skyline Trail, Chester, MA 01011

      Last Sold Summary

      • 2% Above List Price
      • $215/SF
      • 4 Days On Market

      Last Sold Price $505,000

      Last Listing Agent Ed Scagel Happy Valley Realty Group, LLC

  • /49

    $450,000 Sold Feb 17, 2026

    500 E River Rd, Chester, MA 01011

    • 4 Beds
    • 2 Baths
    • 2,171 Sq Ft
    • Built 1820

    Last Sold Summary

    • 6% Below List Price
    • $207/SF
    • 104 Days On Market

    Last Listing Agent Alexis Noyes BRICK & MORTAR REALTY

    500 E River Rd, Chester, MA 01011

Showing Results 1 - 40, Page 1 of 18

Home Trends in Chester, MA

Housing Trends

Median Sale Price
$340,000
Median Single Family Sale Price
$340,000
Average Price Per Sq Ft
$206
Number of Homes for Sale
2
Last 12 months Home Sales
26
Months of Supply
0.90
Median List Price
$341,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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