Chesterfield, MA Homes

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  $449,900 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  574 Main Rd, Chesterfield, MA 01012

  EXPERIENCE THE PERFECT BLEND of classic design and modern comfort in this custom Colonial, nestled in a tranquil setting just 15 minutes from Northampton. The semi-open layout features a bright and airy living room with oversized windows and a gas fireplace, and a recently remodeled kitchen with breakfast bar, ample cabinetry, granite countertops and stainless steel appliances. The spacious

  Jill Vincent-Lapan Canon Real Estate, Inc.

  574 Main Rd, Chesterfield, MA 01012
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  /41

  $475,000 Sold Apr 22, 2025

  • 2,593 Sq Ft
  • $183/SF
  • 5 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1870

  419 Main Rd, Chesterfield, MA 01012

  A quintessential 1870 New England farmhouse, and former Parsonage, built with quality and benefitting from many recent updates. The first floor includes two parlors, dining room with bay window and built in china cupboard and big country kitchen with pantry. The two parlors and dining room all have pegged oak floors. There is a full bath on the first floor as well. Enjoy the cozy heat from

  Michael Packard Coldwell Banker Community REALTORS®

  419 Main Rd, Chesterfield, MA 01012
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  /36

  Est $849,887 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 2,568 Sq Ft

  10 Antin Rd, Chesterfield, MA 01012

  10 Antin Rd, Chesterfield, MA 01012
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  /40

  $449,000

  • 2 Beds
  • 1 Bath
  • 1,024 Sq Ft

  31 Farmhouse Rd, Chesterfield, MA 01012

  Escape to serenity with this charming lakefront residence, a perfect blend of comfort and natural beauty. Built in 1989, this delightful single-family home features 2 cozy bedrooms and 1 full bath, all nestled in a tranquil wooded setting. The open-concept layout invites warmth and light, with expansive windows that frame stunning views of the surrounding landscape. The inviting eat-in kitchen is

  Shelly Hardy

  31 Farmhouse Rd, Chesterfield, MA 01012
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  /13

  $70,000 Sold Apr 15, 2025

  • Land
  • 4.93 Acres
  • $14,199 per Acre

  • 6 Days On Market

  lot A Pynchon Rd, Chesterfield, MA 01012

  An outstanding forest sanctuary. Five acres with some scenic, level areas to build your new home. This land is ready to go with a survey and a recent perk test, The setting has mature forest with stone walls and rock outcroppings. A private setting in a quiet area, yet close to Northampton, the colleges and the Berkshires.

  James Adams Hilltown Real Estate by Adams Realty

  lot A Pynchon Rd, Chesterfield, MA 01012
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  /33

  Est $397,547 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft

  87 Cummington Rd, West Chesterfield, MA 01084

  87 Cummington Rd, West Chesterfield, MA 01084
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  /40

  $899,000

  • 3 Beds
  • 2 Baths
  • 2,922 Sq Ft

  330 East St, Williamsburg, MA 01096

  Welcome to your sanctuary of privacy, natural beauty and well-being! This exquisitely designed home, set on 70 acres, is built with the highest standards for a healthy lifestyle. Enjoy the unparalleled comfort of geothermal radiant heating, providing consistent warmth throughout the home. Large south facing windows, designed for passive solar, bathe the home in natural light, creating a bright,

  Linda Webster Coldwell Banker Community REALTORS®

  330 East St, Williamsburg, MA 01096
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  /22

  $205,000 Sold Mar 24, 2025

  • 508 Sq Ft
  • $404/SF
  • 150 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1960

  43 Don Emerson Rd, Chesterfield, MA 01012

  Nice little seasonal cottage with a large porch overlooking the Pond. Rustic interior, comes with some furnishings. Beautiful large lot with newer drilled well and older septic system. Cleared path down to the shore with small dock in need or work. Lovely view of the lake. Truly a great property for future expansion. Only a short distance from the Town maintained and plowed portion of the

  James Molyneux Molyneux Realty

  43 Don Emerson Rd, Chesterfield, MA 01012
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  Not Listed For Sale

  Lot 2 Bissell Rd, Chesterfield, MA 01012

  Lot 2 Bissell Rd, Chesterfield, MA 01012
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  /4

  $89,000

  • Land
  • 2.06 Acres
  • $43,204 per Acre

  63 Sugar Hill Rd, Williamsburg, MA 01096

  A building lot that is ready to go! Level, mostly open, with a well and two bedroom septic system already in place. Located on a charming paved country road, with easy access to Routes 143 and 9. The stone foundation from a former barn, stone walls and a man made pond are some of the interesting features found on this lot. All in all a really nice property in a super location.

  Michael Packard Coldwell Banker Community REALTORS®

  63 Sugar Hill Rd, Williamsburg, MA 01096
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  /27

  $300,000 Sold Mar 14, 2025

  • 1,094 Sq Ft
  • $274/SF
  • 20 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1996

  11 Damon Pond Rd, Chesterfield, MA 01012

  In the rolling hills of Western New England is a peaceful setting, nestled in nature, offering a sense of privacy. Although you know you have neighbors, you really don’t see them unless you want to see them! In the summer and winter, what you do see is nature’s beauty. Whether you’re sitting alongside your own tiny, private pond, in your garden or out by the woods, you can truly soak in

  James Kwiecinski The Murphys REALTORS®, Inc.

  11 Damon Pond Rd, Chesterfield, MA 01012
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  /17

  Not Listed For Sale

  0 East St, Chesterfield, MA 01012

  0 East St, Chesterfield, MA 01012
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  /41

  $338,700 Pending

  • 2 Beds
  • 1 Bath
  • 1,300 Sq Ft

  325 East St, Williamsburg, MA 01096

  Your Countryside Retreat Awaits! Nestled in the serene woods of Chesterfield, this charming two-bedroom home offers the perfect blend of privacy and convenience. Enjoy the tranquility of nature while remaining just minutes from Northampton, Easthampton, and Florence. Step inside to find a cozy, well-appointed kitchen with a gas stove and a bright four-season room that invites you to relax while

  Cyd Scott Cohn & Company

  325 East St, Williamsburg, MA 01096
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  /10

  $132,000 Sold Feb 07, 2025

  • Land
  • 3.81 Acres
  • $34,646 per Acre

  • 89 Days On Market

  Lot 6 Bissell Rd, Chesterfield, MA 01096

  Beautiful 3.808 acre country lot in rural setting in Chesterfield. 200.44 ft frontage on Bissell Rd. Wooded, perked lot to build your very own house! Land is very slightly sloping front to back; west to east. Situated in the foothills of the Berkshires - easy drive to Northampton (~15 minutes). Access to electrical service at street. High-speed broadband internet service available. Beautiful fall

  Darin Thompson Stuart St James, Inc.

  Lot 6 Bissell Rd, Chesterfield, MA 01096
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  /22

  Est $449,630 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,647 Sq Ft

  84 South St, Chesterfield, MA 01012

  84 South St, Chesterfield, MA 01012
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  /42

  $399,900 Pending

  • 3 Beds
  • 2 Baths
  • 2,043 Sq Ft

  11 Bryant St, Chesterfield, MA 01012

  Amazing split level home with privacy, land and small town vibes! Chesterfield is a picturesque town on the western border of Hampshire County, close to the Berkshires and all that the area has to offer, yet also close to points east such as Northampton and Springfield. Here you will find 3 bedrooms and 1 bath on the upper level, a large living room with fireplace, dining area and new kitchen on

  Kempf-Vanderburgh Realty Consultants Kempf-Vanderburgh Realty Consultants, Inc.

  11 Bryant St, Chesterfield, MA 01012
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  /9

  $75,000 Sold Jan 31, 2025

  • Land
  • 1.08 Acres
  • $69,444 per Acre

  • 138 Days On Market

  0 Antin Rd, Chesterfield, MA 01012

  SELLER REDUCES PRICE FOR THIS rare waterfront lot on Damon Pond offering canoe, kayak, fishing, beach access, and more. This lot is surveyed with a driveway and cleared area to get started on your building site. There is an Electric Service pole on site with an old Meter and breaker box so power is available on site. 99.5 feet along the water with a older dock/deck at the shore edge. Pleasant

  James Molyneux Molyneux Realty

  0 Antin Rd, Chesterfield, MA 01012
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  /28

  Est $317,297 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,308 Sq Ft

  21 South St, Chesterfield, MA 01012

  21 South St, Chesterfield, MA 01012
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  /9

  $60,000 Pending

  • Land
  • 4.47 Acres
  • $13,423 per Acre

  40 East St, Chesterfield, MA 01012

  Lovely building lot on East St in Chesterfield. Partially cleared, with stream access. As a bonus there is a drilled well on-site, and septic plans in hand. The well has both a hand pump and mechanical pump (mechanical pump just needs electric run from the road). Bring your builder and your imagination to create a home in the charming hilltown of Chesterfield. Enjoy the Chesterfield General

  Alexis Noyes

  40 East St, Chesterfield, MA 01012
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  /7

  $75,000 Sold Dec 18, 2024

  • Land
  • 33 Acres
  • $2,260 per Acre

  • 3 Days On Market

  0-B Damon Pond Rd, Chesterfield, MA 01012

  Large wood lot currently under management as forest land. Long frontage. Much wetland with a little elevated area near the road and much of the back acres. Being sold with Ch. 61 in place. This is a portion of an overall larger parcel across the road. Additional 37 acres across the road in MLS# 73293779

  James Molyneux Molyneux Realty

  0-B Damon Pond Rd, Chesterfield, MA 01012
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  /30

  Est $238,285 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 744 Sq Ft

  388 Ireland St, West Chesterfield, MA 01084

  388 Ireland St, West Chesterfield, MA 01084
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  /40

  $350,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,068 Sq Ft

  8 Antin Rd, Chesterfield, MA 01012

  Situated on a quiet back road in Chesterfield, this waterfront property offers a beautiful yard with ample space for relaxation. Located on Damon Pond, this ranch style home has been meticulously maintained and updated with Central A/C. The open concept layout flows nicely, featuring a large, bright kitchen and dining area with beautiful views of the pond. The spacious living room adds to the

  Robert Canon Canon Real Estate, Inc.

  8 Antin Rd, Chesterfield, MA 01012
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  /6

  $175,000 Sold Dec 18, 2024

  • Land
  • 37 Acres
  • $4,688 per Acre

  • 4 Days On Market

  0-A Damon Pond Rd, Chesterfield, MA 01012

  Traditional use for this land has been forest management and part of an additional 33 acres across the road. also for sale. This parcel offers just over 1,000 feet of road frontage by survey and 1,300 ' +- of waterfront on Damon Pond offering future possibilities for this unique parcel. Currently under Chapter 61.

  James Molyneux Molyneux Realty

  0-A Damon Pond Rd, Chesterfield, MA 01012
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  /35

  Est $492,151 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,404 Sq Ft

  309 Ireland St, West Chesterfield, MA 01084

  309 Ireland St, West Chesterfield, MA 01084
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  /40

  $220,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,116 Sq Ft

  134 Indian Hollow Rd, Chesterfield, MA 01012

  Escape to tranquility at this charming 2 BR, 1-bath cottage nestled in nature. Spanning 6.17 acres of lush woodlands, this retreat is perfect for outdoor enthusiasts who enjoy hiking, gardening, or peaceful surroundings. The rustic wood-paneled exterior and sloping landscapes create a cozy lifestyle immersed in nature. Inside, the open floor plan connects the cozy kitchen, living, and dining

  Maria Christina Wichert RE/MAX Connections - Belchertown

  134 Indian Hollow Rd, Chesterfield, MA 01012
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  /7

  $85,000 Sold Dec 18, 2024

  • Land
  • 6 Acres
  • $15,455 per Acre

  • 36 Days On Market

  0 Damon Pond Rd, Chesterfield, MA 01012

  Unique lot with long road frontage on 2 roads creating a triangle. Entirely wooded with a former home site with an old stone lined cellar hole. This location is set nicely between Rt 9 in Goshen, the shared elementary school, center of Chesterfield along with and easy trip to Rt. 143 into Williamsburg. Great site offering a nice residential use with ample frontage and acreage for possible

  James Molyneux Molyneux Realty

  0 Damon Pond Rd, Chesterfield, MA 01012
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  /42

  Est $448,859 Not Listed For Sale

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

  185 East St, Williamsburg, MA 01096

  185 East St, Williamsburg, MA 01096
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  /24

  $67,000 Sold Nov 15, 2024

  • 965 Sq Ft
  • $69/SF
  • 154 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1930

  33 South St, Chesterfield, MA 01012

  Grab your tools & unlock the potential of this 2 bedroom, 1 bathroom fixer-upper! Set on 2 acres, the home is conveniently located near the center of town, the Chesterfield Gorge, and 20 minutes from downtown Northampton. Although the home needs some finishing touches including a new septic system (buyer responsibility), it could be a great investment & opportunity to build some equity! Make your

  Donald Mailloux Coldwell Banker Community REALTORS®

  33 South St, Chesterfield, MA 01012
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  /38

  Est $474,996 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,841 Sq Ft

  213 Ireland St, West Chesterfield, MA 01084

  213 Ireland St, West Chesterfield, MA 01084
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  /39

  $505,000 Sold Oct 31, 2024

  • 2,449 Sq Ft
  • $206/SF
  • 82 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1986

  43 Munson Rd, Chesterfield, MA 01012

  Looking for a mini-farm with some acreage? This Cape on over 13 acres may be just what you're looking for. With 3 bedrooms, 1.5 baths, a partially finished basement, fireplace, hardwood floors, this comfortable home features an open kitchen/diningroom with vaulted ceiling and a skylight; spacious living room featuring a soapstone stove that keeps the house toasty in winter. First floor bedroom is

  Kimberly Goggins 5 College REALTORS® Northampton

  43 Munson Rd, Chesterfield, MA 01012
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  /27

  Est $374,765 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,528 Sq Ft

  1 Curtis Rd, Williamsburg, MA 01096

  1 Curtis Rd, Williamsburg, MA 01096
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  /42

  $440,000 Sold Sep 25, 2024

  • 1,531 Sq Ft
  • $287/SF
  • 56 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1978

  73 North Rd, Chesterfield, MA 01012

  Pastoral setting on 5 acres wrapped in solitude and peace at this unique retreat less than 30 minutes from Northampton. A newly-built driveway leads to a magical log cabin w/ hand-hewn logs, pretty stone fireplace, great wood flrs, and a deep front porch for quiet evenings. Sweet kitchen has meal prep space for the serious home cook. Authentic post-and-beam custom-built wood-fired Finnish sauna

  Amy Heflin Keller Williams Realty

  73 North Rd, Chesterfield, MA 01012
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  /42

  Est $353,388 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,110 Sq Ft

  163 Sugar Hill Rd, Williamsburg, MA 01096

  163 Sugar Hill Rd, Williamsburg, MA 01096
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  /6

  $65,000 Sold Aug 19, 2024

  • Land
  • 2.26 Acres
  • $28,761 per Acre

  • 3 Days On Market

  108-2 South St, Chesterfield, MA 01012

  Enjoy an abundance of wildlife right in your own yard with this newly divided 2.26 acre lot. Lot is roughly 75% cleared, perk has been completed, well is in place and ready for your plans. Bring your imagination and build your dream home.

  Malissa Jean-Charles Keller Williams Boston MetroWest

  108-2 South St, Chesterfield, MA 01012
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  /25

  Est $257,802 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 621 Sq Ft

  563 Main Rd, Chesterfield, MA 01012

  563 Main Rd, Chesterfield, MA 01012
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  /42

  $621,875 Sold Aug 19, 2024

  • 1,988 Sq Ft
  • $313/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  108 South St, Chesterfield, MA 01012

  Escape to your secluded sanctuary on over 20 acres of pristine countryside, just a short drive from Northampton. This contemporary home blends modern comfort with natural beauty, featuring vaulted ceilings and a striking brick fireplace in the spacious living room. Three bedrooms and two baths provide ample space, while a serene three-season porch invites you to enjoy the surrounding wildlife and

  Malissa Jean-Charles Keller Williams Boston MetroWest

  108 South St, Chesterfield, MA 01012
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  /41

  Est $601,067 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,604 Sq Ft

  63 North Rd, Chesterfield, MA 01012

  63 North Rd, Chesterfield, MA 01012
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  /8

  $75,000 Sold Aug 06, 2024

  • Land
  • 0.28 Acre
  • $267,857 per Acre

  • 4 Days On Market

  0 Bray Rd, Chesterfield, MA 01012

  Stunning waterfront lot on Damon Pond. A dock and direct lake access for kayaking or canoeing from this idyllic lot and rare opportunity to own a piece of solitude and quiet. 130 feet of frontage. Tent platform in great shape on site and full canvas tent available for use for new owner. Shade and sunlight mix for a pretty incredible spot for swimming or reading or a cookout with friends.

  Amy Heflin Keller Williams Realty

  0 Bray Rd, Chesterfield, MA 01012
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  /42

  Est $426,464 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft

  24 Farmhouse Rd, Chesterfield, MA 01012

  24 Farmhouse Rd, Chesterfield, MA 01012
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  $310,000 Sold Aug 02, 2024

  • 1,260 Sq Ft
  • $246/SF
  • 10 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  386 Main Rd, Chesterfield, MA 01012

  Charming antique farmhouse on 11 acres exudes rustic allure. This 3-bedroom, 1-bath abode boasts original wood floors that tell tales of generations past. The character-rich ambiance is a testament to its history. The bedrooms are all on one floor with some separation for privacy. The oversized kitchen can handle a large table for your gatherings. A rustic barn is a great spot for your hobbies or

  The Jackson & Nale Team RE/MAX Connections - Belchertown

  386 Main Rd, Chesterfield, MA 01012

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