975

Chester, MA Homes

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

    $414,999

    • 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
  • 76 Hampden St, Chester, MA 01011
    76 Hampden St, Chester, MA 01011
    76 Hampden St, 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

    Last Listing Agent Stacey Silvia Lock and Key Realty Inc.

    76 Hampden St, Chester, MA 01011
    • 67 Crane Rd, Chester, MA 01011
      67 Crane Rd, Chester, MA 01011
      67 Crane Rd, Chester, MA 01011
      /21

      Est $47,966 Not Listed For Sale

      67 Crane Rd, Chester, MA 01011

      67 Crane Rd, Chester, MA 01011
  • 0 E River Rd Lot 13 Map 409 Unit 72690617, Chester, MA 01050
    0 E River Rd Lot 13 Map 409 Unit 72690617, Chester, MA 01050
    0 E River Rd Lot 13 Map 409 Unit 72690617, Chester, MA 01050
    /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
  • 689 Skyline Trail, Chester, MA 01011
    689 Skyline Trail, Chester, MA 01011
    689 Skyline Trail, Chester, MA 01011
    /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

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

    689 Skyline Trail, Chester, MA 01011
    • 0 Abbott Hill Rd, Chester, MA 01011
      0 Abbott Hill Rd, Chester, MA 01011
      0 Abbott Hill Rd, Chester, MA 01011
      /5

      Not Listed For Sale

      0 Abbott Hill Rd, Chester, MA 01011

      0 Abbott Hill Rd, Chester, MA 01011
  • 11 Taft Rd, Chester, MA 01011
    11 Taft Rd, Chester, MA 01011
    11 Taft Rd, Chester, MA 01011
    /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
  • 424 Route 20, Chester, MA 01011
    424 Route 20, Chester, MA 01011
    424 Route 20, 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 $433,713

    Last Listing Agent Angela Accorsi Coldwell Banker Realty - Western MA

    424 Route 20, Chester, MA 01011
    • 110 Old State Hwy, Chester, MA 01011
      110 Old State Hwy, Chester, MA 01011
      110 Old State Hwy, Chester, MA 01011
      /18

      Est $276,465 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,509 Sq Ft

      110 Old State Hwy, Chester, MA 01011

      110 Old State Hwy, Chester, MA 01011
  • 147 Chipman Rd, Chester, MA 01011
    147 Chipman Rd, Chester, MA 01011
    147 Chipman Rd, Chester, MA 01011
    /42

    $469,900

    • 3 Beds
    • 2.5 Baths
    • 2,068 Sq Ft

    147 Chipman Rd, Chester, MA 01011

    Welcome home to this 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! Enter through the welcoming foyer to the main level that features a spacious living room & dining area w/ propane stove & sliders to a sunny deck, a kitchen with pantry closet, half bath with laundry, a first-floor office, & a

    Taylor Hildack Keller Williams Realty

    147 Chipman Rd, Chester, MA 01011
  • 300 Middlefield Rd, Chester, MA 01011
    300 Middlefield Rd, Chester, MA 01011
    300 Middlefield Rd, 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 $257,369

    Last Listing Agent Nicolle Serafino Keller Williams Realty

    300 Middlefield Rd, Chester, MA 01011
    • 664 Route 20, Chester, MA 01011
      664 Route 20, Chester, MA 01011
      664 Route 20, Chester, MA 01011
      /10

      Est $156,099 Not Listed For Sale

      • 6 Beds
      • 2 Baths
      • 2,400 Sq Ft

      664 Route 20, Chester, MA 01011

      664 Route 20, Chester, MA 01011
  • 171 Prospect St, Chester, MA 01011
    171 Prospect St, Chester, MA 01011
    171 Prospect St, Chester, MA 01011
    /22

    $49,500 Pending

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

    171 Prospect St, Chester, MA 01011

    Beautiful wood house with tons of space and character, needs some love to bring back to life. Nestled into the hills of Chester, it's just steps away from the Railway Museum and downtown. Foundation partially rebuild with newer windows and doors. Much work already done. Come bring it over the finish line and have yourself a beautiful historic house with amazing mountain and river views.

    Vadim Tulchinsky Witman Properties, Inc.

    171 Prospect St, Chester, MA 01011
  • 45 Middlefield Rd, Chester, MA 01011
    45 Middlefield Rd, Chester, MA 01011
    45 Middlefield Rd, 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 $234,645

    Last Listing Agent Joy Salvini RE/MAX Compass

    45 Middlefield Rd, Chester, MA 01011
    • 85 Lyman Rd, Chester, MA 01011
      85 Lyman Rd, Chester, MA 01011
      85 Lyman Rd, Chester, MA 01011
      /34

      Est $429,019 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,440 Sq Ft

      85 Lyman Rd, Chester, MA 01011

      85 Lyman Rd, Chester, MA 01011
  • 67 Middlefield Rd, Chester, MA 01011
    67 Middlefield Rd, Chester, MA 01011
    67 Middlefield Rd, Chester, MA 01011
    /24

    $299,000

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

    67 Middlefield Rd, Chester, MA 01011

    Charming R-Zoned Property on 3 Cleared Acres with Barn - Chester, MA Set on 3 cleared acres in the peaceful town of Chester, this Single-Family Residential property offers space, privacy, and flexibility with R zoning. The home features 1,896 square feet of living space, including 2 bedrooms and 2 full baths, making it ideal for year-round living or a country retreat. Key systems are in good

    Alex King Lock and Key Realty, Inc

    67 Middlefield Rd, Chester, MA 01011
  • 143 Chipman Rd, Chester, MA 01011
    143 Chipman Rd, Chester, MA 01011
    143 Chipman Rd, Chester, MA 01011
    /25

    $288,700 Sold Mar 31, 2025

    143 Chipman Rd, Chester, MA 01011

    • 2 Beds
    • 2 Baths
    • 1,486 Sq Ft
    • Built 1988

    Last Sold Summary

    • 7% Below List Price
    • $194/SF
    • 113 Days On Market

    Current Estimated Value $313,082

    Last Listing Agent Zachary DeCaro Property Works New England

    143 Chipman Rd, Chester, MA 01011
    • 40 Holcomb Rd, Chester, MA 01011
      40 Holcomb Rd, Chester, MA 01011
      40 Holcomb Rd, Chester, MA 01011
      /34

      Est $314,313 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,236 Sq Ft

      40 Holcomb Rd, Chester, MA 01011

      40 Holcomb Rd, Chester, MA 01011
  • 12 Riverfront St, Chester, MA 01011
    12 Riverfront St, Chester, MA 01011
    12 Riverfront St, Chester, MA 01011
    /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
  • lot 13 Skyline Trail, Chester, MA 01011
    lot 13 Skyline Trail, Chester, MA 01011
    lot 13 Skyline Trail, Chester, MA 01011
    /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
    • 627 Skyline Trail, Chester, MA 01011
      627 Skyline Trail, Chester, MA 01011
      627 Skyline Trail, Chester, MA 01011
      /17

      Est $201,181 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 708 Sq Ft

      627 Skyline Trail, Chester, MA 01011

      627 Skyline Trail, Chester, MA 01011
  • 254 Route 20, Chester, MA 01011
    254 Route 20, Chester, MA 01011
    254 Route 20, Chester, MA 01011
    /38

    $279,500 Pending

    • 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
  • 120 Fisk Rd, Worthington, MA 01098
    120 Fisk Rd, Worthington, MA 01098
    120 Fisk Rd, Worthington, MA 01098
    /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

    Last Listing Agent Kylene Canon Canon Real Estate, Inc.

    120 Fisk Rd, Worthington, MA 01098
    • 78 Lyon Hill Rd, Chester, MA 01011
      78 Lyon Hill Rd, Chester, MA 01011
      78 Lyon Hill Rd, Chester, MA 01011
      /54

      Est $510,654 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,130 Sq Ft

      78 Lyon Hill Rd, Chester, MA 01011

      78 Lyon Hill Rd, Chester, MA 01011
  • 73 Ingell Rd, Chester, MA 01011
    73 Ingell Rd, Chester, MA 01011
    73 Ingell Rd, Chester, MA 01011
    /19

    $425,000 Pending

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

    73 Ingell Rd, Chester, MA 01011

    Located on a country road with expansive views. Rustic ranch-style farmhouse with a western flair. Notable improvements in the last 10 years roof/windows/skylight/furnace and updates to the electric. Generous open floor plan for the kitchen and living room with peaceful outside views to expansive skies. Second floor heated studio with approximately 385sf, potential to connect to the main house.

    Debra Petrovsky Donovan Real Estate

    73 Ingell Rd, Chester, MA 01011
  • 613 Skyline Trail, Chester, MA 01011
    613 Skyline Trail, Chester, MA 01011
    613 Skyline Trail, Chester, MA 01011
    /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 $481,108

    Last Listing Agent Denise DeSellier Berkshire Hathaway HomeServices Realty Professionals

    613 Skyline Trail, Chester, MA 01011
    • 36 Lyon Hill Rd, Chester, MA 01011
      36 Lyon Hill Rd, Chester, MA 01011
      36 Lyon Hill Rd, Chester, MA 01011
      /38

      Est $452,843 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,144 Sq Ft

      36 Lyon Hill Rd, Chester, MA 01011

      36 Lyon Hill Rd, Chester, MA 01011
  • 187 Route 20, Chester, MA 01011
    187 Route 20, Chester, MA 01011
    187 Route 20, Chester, MA 01011
    /23

    $234,900

    • 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
  • 9 William St, Chester, MA 01011
    9 William St, Chester, MA 01011
    9 William St, Chester, MA 01011
    /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 $305,416

    Last Listing Agent Adam Lajeunesse Real Broker MA, LLC

    9 William St, Chester, MA 01011
    • 499 Skyline Trail, Chester, MA 01011
      499 Skyline Trail, Chester, MA 01011
      499 Skyline Trail, Chester, MA 01011
      /31

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 3,844 Sq Ft

      499 Skyline Trail, Chester, MA 01011

      499 Skyline Trail, Chester, MA 01011
  • 500 E River Rd, Chester, MA 01011
    500 E River Rd, Chester, MA 01011
    500 E River Rd, Chester, MA 01011
    /42

    $460,000 Pending

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

    500 E River Rd, Chester, MA 01011

    This 1800's farmhouse was once home to The Ideal Shoe Company (Danvers, MA). It's a property rich with history, charm, and situated in the middle of 13+ gorgeous acres fit to explore, or simply revel in their beauty. Surrounded by hundreds of acres of conservation land, your adventures could be endless. Take in the tranquil sounds of the Westfield River while roaming the tree-lined paths or

    Alexis Noyes Brick & Mortar Northhampton

    500 E River Rd, Chester, MA 01011
  • lot 61 Skyline Trail, Chester, MA 01011
    lot 61 Skyline Trail, Chester, MA 01011
    lot 61 Skyline Trail, Chester, MA 01011
    /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
    • 115 Lyon Hill Rd, Chester, MA 01011
      115 Lyon Hill Rd, Chester, MA 01011
      115 Lyon Hill Rd, Chester, MA 01011
      /20

      Est $183,376 Not Listed For Sale

      • 4 Beds

      115 Lyon Hill Rd, Chester, MA 01011

      115 Lyon Hill Rd, Chester, MA 01011
  • 0 Round Hill Rd Unit 73399828, Chester, MA 01011
    0 Round Hill Rd Unit 73399828, Chester, MA 01011
    0 Round Hill Rd Unit 73399828, Chester, MA 01011
    /6

    $25,000 Pending

    • Land
    • 3.24 Acres
    • $7,716 per Acre

    0 Round Hill Rd Unit 73399828, Chester, MA 01011

    Price drop on this great get away with over three acres. There is a recent perk test, if you want to build on the land. This property comes with a newer camper. Walking distance to the hiking trails of the expansive Chester State Forest. The road does not have electric at this time, so off grid living is the way to go. 200 feet north of Smithy Road.

    James Adams Hilltown Real Estate by Adams Realty

    0 Round Hill Rd Unit 73399828, Chester, MA 01011
  • 20 William St, Chester, MA 01011
    20 William St, Chester, MA 01011
    20 William St, Chester, MA 01011
    /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 $299,290

    Last Listing Agent Tammy Weidhaas Today Real Estate, Inc.

    20 William St, Chester, MA 01011
    • 72 Maynard Hill Rd, Chester, MA 01011
      72 Maynard Hill Rd, Chester, MA 01011
      72 Maynard Hill Rd, Chester, MA 01011
      /3

      Est $176,846 Not Listed For Sale

      • 2 Beds

      72 Maynard Hill Rd, Chester, MA 01011

      72 Maynard Hill Rd, Chester, MA 01011
  • lot 3 Skyline Trail, Chester, MA 01011
    lot 3 Skyline Trail, Chester, MA 01011
    lot 3 Skyline Trail, Chester, MA 01011
    /4

    $50,000

    • Land
    • 3 Acres
    • $16,667 per Acre

    lot 3 Skyline Trail, Chester, MA 01011

    A great 3-acre parcel on a paved road with stone walls. Lightly forested and flat. This is a relatively easy building site for your new home. Land is just north of 590 Skyline trail.

    James Adams Hilltown Real Estate by Adams Realty

    lot 3 Skyline Trail, Chester, MA 01011
  • 396 Route 20, Chester, MA 01011
    396 Route 20, Chester, MA 01011
    396 Route 20, Chester, MA 01011
    /26

    $240,000 Sold Jan 31, 2025

    396 Route 20, Chester, MA 01011

    • 2 Beds
    • 1 Bath
    • 1,156 Sq Ft
    • Built 1957

    Last Sold Summary

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

    Current Estimated Value $255,431

    Last Listing Agent Maureen Borg Delap Real Estate LLC

    396 Route 20, Chester, MA 01011
    • 674 Skyline Trail, Chester, MA 01011
      674 Skyline Trail, Chester, MA 01011
      674 Skyline Trail, Chester, MA 01011
      /36

      Est $551,174 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,352 Sq Ft

      674 Skyline Trail, Chester, MA 01011

      674 Skyline Trail, Chester, MA 01011
  • 506 Skyline Trail, Chester, MA 01011
    506 Skyline Trail, Chester, MA 01011
    506 Skyline Trail, Chester, MA 01011
    /18

    $578,900

    • 4 Beds
    • 2 Baths
    • 2,244 Sq Ft

    506 Skyline Trail, Chester, MA 01011

    Set along the scenic Skyline Trail, this fully renovated home offers refined finishes, abundant natural light, and an elegant open layout. A long, estate-style concrete approach creates a grand sense of arrival, leading to a beautifully updated interior with porcelain tile floors, modern updates, and two fireplaces that add warmth and character. The finished bonus space just off the main living

    Oleg Abramchuk First NationWide Realty Inc.

    506 Skyline Trail, Chester, MA 01011

Showing Results 1 - 40, Page 1 of 18

Massachusetts Hampden County Chester

Real Estate & Homes

Home Trends in Chester, MA

On average, homes in Chester, MA sell after 39 days on the market compared to the national average of 53 days. The median sale price for homes in Chester, MA over the last 12 months is $300,000, consistent with the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$300,000
Median Single Family Sale Price
$299,950
Average Price Per Sq Ft
$215
Number of Homes for Sale
4
Last 12 months Home Sales
19
Months of Supply
2.50
Median List Price
$299,949
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
0%
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