1,196

Homes in ZIP Code 01011

Section Image
  • 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
  • 113 Iroquois Ave, Becket, MA 01223
    113 Iroquois Ave, Becket, MA 01223
    113 Iroquois Ave, Becket, MA 01223
    /38

    $589,000 Sold Oct 03, 2025

    113 Iroquois Ave, Becket, MA 01223

    • 5 Beds
    • 3 Baths
    • 2,350 Sq Ft
    • Built 1987

    Last Sold Summary

    • 883% Above List Price
    • $251/SF
    • 40 Days On Market

    Current Estimated Value $592,029

    Last Listing Agent Ginger Conner RED HORSE REAL ESTATE, LLC

    113 Iroquois Ave, Becket, MA 01223
    • 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
  • 110 Middlefield Rd, Chester, MA 01011
    110 Middlefield Rd, Chester, MA 01011
    110 Middlefield Rd, Chester, MA 01011
    /33

    $300,000 Sold Aug 22, 2025

    110 Middlefield Rd, Chester, MA 01011

    • 3 Beds
    • 1 Bath
    • 1,712 Sq Ft
    • Built 1900

    Last Sold Summary

    • $175/SF
    • 4 Days On Market

    Current Estimated Value $297,824

    Last Listing Agent Darcie Gasperini Taylor Agency

    110 Middlefield Rd, 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
  • 124 Skyline Trail, Chester, MA 01011
    124 Skyline Trail, Chester, MA 01011
    124 Skyline Trail, Chester, MA 01011
    /43

    $749,000 Sold Oct 07, 2025

    124 Skyline Trail, Chester, MA 01011

    • 3 Beds
    • 2 Baths
    • 2,871 Sq Ft
    • Built 2004

    Last Sold Summary

    • $261/SF
    • 7 Days On Market

    Current Estimated Value $739,416

    Last Listing Agent Herb Butzke WILLIAM PITT SOTHEBY'S - LENOX

    124 Skyline Trail, Chester, MA 01011
    • 15 Maple St, Chester, MA 01011
      15 Maple St, Chester, MA 01011
      15 Maple St, Chester, MA 01011
      /41

      Est $273,167 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,136 Sq Ft

      15 Maple St, Chester, MA 01011

      15 Maple St, Chester, MA 01011
  • 4 Maple St, Chester, MA 01011
    4 Maple St, Chester, MA 01011
    4 Maple St, Chester, MA 01011
    /30

    $289,000

    • 4 Beds
    • 2 Baths
    • 3,864 Sq Ft

    4 Maple St, Chester, MA 01011

    Spacious two-family property located in desirable Hampden County. This 3,864 sq ft multi-family offers a total of 6 bedrooms and 2 full bathrooms across two units. Features include ample off-street parking and generous living space, making it ideal for owner-occupants or investors alike. Conveniently located near local amenities, schools, and major routes.

    Adam Devine Dorrance Realty LLC

    4 Maple St, Chester, MA 01011
  • 166 Bromley Rd, Chester, MA 01011
    166 Bromley Rd, Chester, MA 01011
    166 Bromley Rd, Chester, MA 01011
    /42

    $445,000 Sold Mar 14, 2025

    166 Bromley Rd, Chester, MA 01011

    • 5 Beds
    • 3 Baths
    • 2,094 Sq Ft
    • Built 1996

    Last Sold Summary

    • 6% Below List Price
    • $213/SF
    • 79 Days On Market

    Last Listing Agent Taylor Hildack Keller Williams Realty

    166 Bromley Rd, Chester, MA 01011
    • 175 Route 20, Chester, MA 01011
      175 Route 20, Chester, MA 01011
      175 Route 20, Chester, MA 01011
      /24

      Est $256,235 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,000 Sq Ft

      175 Route 20, Chester, MA 01011

      175 Route 20, Chester, MA 01011
  • 11 Campbell Rd, Chester, MA 01011
    11 Campbell Rd, Chester, MA 01011
    11 Campbell Rd, Chester, MA 01011
    /41

    $368,900 Pending

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

    11 Campbell Rd, Chester, MA 01011

    This private Colonial home is set on 2.5 wooded acres at the end of a quiet dead-end road in Chester’s “Gem of the Valley.” The property is fully equipped for equestrian and homesteading lifestyles, featuring a four-stall barn with walk-out access to a fenced paddock, along with two additional fenced pastures ideal for horses, goats, or other farm animals. Inside, the home has been freshly

    Jessica Sperry Maverick Realty

    11 Campbell Rd, Chester, MA 01011
  • 21 Sylvester Hamilton Rd, Chester, MA 01011
    21 Sylvester Hamilton Rd, Chester, MA 01011
    21 Sylvester Hamilton Rd, Chester, MA 01011
    /42

    $380,000 Sold Dec 03, 2025

    21 Sylvester Hamilton Rd, Chester, MA 01011

    • 2 Beds
    • 1 Bath
    • 1,113 Sq Ft
    • Built 1984

    Last Sold Summary

    • 6% Above List Price
    • $341/SF
    • 19 Days On Market

    Last Listing Agent Linda Webster Coldwell Banker Community REALTORS®

    21 Sylvester Hamilton Rd, Chester, MA 01011
    • 217 Route 20, Chester, MA 01011
      217 Route 20, Chester, MA 01011
      217 Route 20, Chester, MA 01011
      /21

      Est $184,778 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,367 Sq Ft

      217 Route 20, Chester, MA 01011

      217 Route 20, Chester, MA 01011
  • Lot 155 Chippewa Dr, Becket, MA 01223
    Lot 155 Chippewa Dr, Becket, MA 01223
    Lot 155 Chippewa Dr, Becket, MA 01223
    /7

    $25,000

    • Land
    • 2.26 Acres
    • $11,062 per Acre

    Lot 155 Chippewa Dr, Becket, MA 01223

    Come and build your Berkshire dream home in Indian Lake Association. The lot provides for a private country setting with all the amenities of the lake and tennis courts. The private roads throughout the community make for a quiet stroll at any point in time.

    David St. Laurent BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS OTIS

    Lot 155 Chippewa Dr, Becket, MA 01223
  • 7 William St, Chester, MA 01011
    7 William St, Chester, MA 01011
    7 William St, Chester, MA 01011
    /37

    $291,000 Sold Dec 01, 2025

    7 William St, Chester, MA 01011

    • 3 Beds
    • 2 Baths
    • 1,912 Sq Ft
    • Built 1875

    Last Sold Summary

    • 1% Below List Price
    • $152/SF
    • 28 Days On Market

    Last Listing Agent James Adams Hilltown Real Estate by Adams Realty

    7 William St, Chester, MA 01011
    • 278 Route 20, Chester, MA 01011
      278 Route 20, Chester, MA 01011
      278 Route 20, Chester, MA 01011
      /24

      Est $255,335 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,399 Sq Ft

      278 Route 20, Chester, MA 01011

      278 Route 20, Chester, MA 01011
  • 279 Goss Hill Rd, Huntington, MA 01050
    279 Goss Hill Rd, Huntington, MA 01050
    279 Goss Hill Rd, Huntington, MA 01050
    /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
  • Lot16 Chester Rd, Middlefield, MA 01011
    Lot16 Chester Rd, Middlefield, MA 01011
    Lot16 Chester Rd, Middlefield, MA 01011
    /9

    $29,900 Sold Jun 06, 2025

    Lot16 Chester Rd, Middlefield, MA 01011

    • Land
    • 5.33 Acres
    • $5,610 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 24 Days On Market

    Last Listing Agent Kim Bergland RED HORSE REAL ESTATE, LLC

    Lot16 Chester Rd, Middlefield, MA 01011
    • 16 Maple St, Chester, MA 01011
      16 Maple St, Chester, MA 01011
      16 Maple St, Chester, MA 01011
      /18

      Est $221,830 Not Listed For Sale

      • 6 Beds
      • 2 Baths
      • 1,971 Sq Ft

      16 Maple St, Chester, MA 01011

      16 Maple St, Chester, MA 01011
  • Lot19 Skyline Ridge Rd, Becket, MA 01223
    Lot19 Skyline Ridge Rd, Becket, MA 01223
    Lot19 Skyline Ridge Rd, Becket, MA 01223
    /10

    $39,900

    • Land
    • 4.48 Acres
    • $8,906 per Acre

    Lot19 Skyline Ridge Rd, Becket, MA 01223

    4.48 acre lot in the Skyline Ridge HOA. Potential views to the north. Several existing homes are located nearby with distant mountain and ridge views. Bordering State Forest, lakes, trails and the cultural attractions of the Berkshires nearby. Successful perc test 2003: 2.3 MPI.

    Kim Bergland RED HORSE REAL ESTATE, LLC

    Lot19 Skyline Ridge Rd, Becket, MA 01223
  • 54 Route 20, Chester, MA 01011
    54 Route 20, Chester, MA 01011
    54 Route 20, Chester, MA 01011
    /29

    $242,000 Sold Mar 21, 2025

    54 Route 20, Chester, MA 01011

    • 3 Beds
    • 2 Baths
    • 1,411 Sq Ft
    • Built 1875

    Last Sold Summary

    • $172/SF
    • 116 Days On Market

    Current Estimated Value $246,392

    Last Listing Agent Susan Deacon RE/MAX COMPASS

    54 Route 20, Chester, MA 01011
    • 9 Prospect St, Chester, MA 01011
      9 Prospect St, Chester, MA 01011
      9 Prospect St, Chester, MA 01011
      /35

      Est $230,306 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,540 Sq Ft

      9 Prospect St, Chester, MA 01011

      9 Prospect St, Chester, MA 01011
  • 10 William St, Chester, MA 01011
    10 William St, Chester, MA 01011
    10 William St, Chester, MA 01011
    /19

    $110,000 Pending

    • 4 Beds
    • 2 Baths
    • 2,394 Sq Ft

    10 William St, Chester, MA 01011

    Come see this charming colonial-style home featuring four bedrooms and two full bathrooms, encompassing nearly 2,400 square feet of living space! Nestled on an expansive 24.8-acre lot, the property does provide some nice privacy potential. A spacious barn is also included, presenting numerous opportunities for use as a workshop or additional storage. Additionally, the property features an

    Nicholas Decaro Property Works New England

    10 William St, Chester, MA 01011
    • 21 Middlefield Rd, Chester, MA 01011
      21 Middlefield Rd, Chester, MA 01011
      21 Middlefield Rd, Chester, MA 01011
      /23

      Est $354,755 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,100 Sq Ft

      21 Middlefield Rd, Chester, MA 01011

      21 Middlefield Rd, Chester, MA 01011
    • 59 Middlefield Rd, Chester, MA 01011
      59 Middlefield Rd, Chester, MA 01011
      59 Middlefield Rd, Chester, MA 01011
      /40

      Est $221,168 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,320 Sq Ft

      59 Middlefield Rd, Chester, MA 01011

      59 Middlefield Rd, Chester, MA 01011
    • 52 Middlefield Rd, Chester, MA 01011
      52 Middlefield Rd, Chester, MA 01011
      52 Middlefield Rd, Chester, MA 01011
      /42

      Est $197,419 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,280 Sq Ft

      52 Middlefield Rd, Chester, MA 01011

      52 Middlefield Rd, Chester, MA 01011
    • 29 William St, Chester, MA 01011
      29 William St, Chester, MA 01011
      29 William St, Chester, MA 01011
      /39

      Est $245,589 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,056 Sq Ft

      29 William St, Chester, MA 01011

      29 William St, Chester, MA 01011
    • 850 Chester Rd, Becket, MA 01223
      850 Chester Rd, Becket, MA 01223
      850 Chester Rd, Becket, MA 01223
      /13

      Est $205,977 Not Listed For Sale

      • 6 Beds
      • 2.5 Baths
      • 1,884 Sq Ft

      850 Chester Rd, Becket, MA 01223

      850 Chester Rd, Becket, MA 01223
    • 1088 Chester Rd, Becket, MA 01223
      1088 Chester Rd, Becket, MA 01223
      1088 Chester Rd, Becket, MA 01223
      /22

      Est $116,830 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 990 Sq Ft

      1088 Chester Rd, Becket, MA 01223

      1088 Chester Rd, Becket, MA 01223
    • 0065 Round Hill Rd, Chester, MA 01011
      0065 Round Hill Rd, Chester, MA 01011
      0065 Round Hill Rd, Chester, MA 01011
      /7

      Not Listed For Sale

      0065 Round Hill Rd, Chester, MA 01011

      0065 Round Hill Rd, Chester, MA 01011
    • 006 Round Hill Rd, Chester, MA 01011
      006 Round Hill Rd, Chester, MA 01011
      006 Round Hill Rd, Chester, MA 01011
      /5

      Not Listed For Sale

      006 Round Hill Rd, Chester, MA 01011

      006 Round Hill Rd, Chester, MA 01011
    • 000 Lynes Rd, Chester, MA 01011
      000 Lynes Rd, Chester, MA 01011
      000 Lynes Rd, Chester, MA 01011
      /4

      Not Listed For Sale

      000 Lynes Rd, Chester, MA 01011

      000 Lynes Rd, Chester, MA 01011
    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /11

      Not Listed For Sale

      Unlisted Address

      Unlisted Address
    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /7

      Not Listed For Sale

      Unlisted Address

      Unlisted Address
    • 0 Goss Hill Unit 73207388, Chester, MA 01011
      0 Goss Hill Unit 73207388, Chester, MA 01011
      0 Goss Hill Unit 73207388, Chester, MA 01011
      /6

      Not Listed For Sale

      0 Goss Hill Unit 73207388, Chester, MA 01011

      0 Goss Hill Unit 73207388, Chester, MA 01011
    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /7

      Not Listed For Sale

      Unlisted Address

      Unlisted Address
    • 67 Cherokee Rd, Becket, MA 01223
      67 Cherokee Rd, Becket, MA 01223
      67 Cherokee Rd, Becket, MA 01223
      /37

      Est $732,322 Not Listed For Sale

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

      67 Cherokee Rd, Becket, MA 01223

      67 Cherokee Rd, Becket, MA 01223
    • 0 Round Hill Rd Unit 73136186, Chester, MA 01011
      0 Round Hill Rd Unit 73136186, Chester, MA 01011
      0 Round Hill Rd Unit 73136186, Chester, MA 01011
      /4

      Not Listed For Sale

      0 Round Hill Rd Unit 73136186, Chester, MA 01011

      0 Round Hill Rd Unit 73136186, Chester, MA 01011

Showing Results 41 - 80, Page 2 of 18

Massachusetts Hampden County Chester 01011

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

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