Chesterfield Real Estate

Perhaps best known for the beautiful Chesterfield Gorge, Chesterfield is a small town located northwest of Northampton. Take in the view of the gorge's steep metamorphic rock cliffs from the trail along its edges, go fishing in Scout Pond, or enjoy the many other perks of Berkshire living. Scroll down to view all Chesterfield, MA real estate for sale, including single-family homes, commercial properties, land and more.

Browse Chesterfield MA Real Estate

Contact us today to find out more about real estate in Chesterfield, MA. Found a property you love? Register to save your search, save your favorite listings, and receive notification when a new property enters your search criteria.

416 Main Road, Chesterfield, MA

Price$599,000

Est. Mortgage: $/month

MLS Number 72356681

  • Single Family
  • Parking Spaces 4
  • Year Built 1822
  • Full Bath 3
  • Bathroom 4

Glory! This remarkably preserved 5 bedroom, 3 and half bath, 1822 center hall colonial is distinctive. Offering period details including Rumford fireplaces, high ceilings, original moldings and wide-plank Chestnut floors, this is a true Federal style home the kind you will rarely find anywhere else. While maintaining its historic integrity, the house has been tastefully updated with a modern kitchen containing custom cherry cabinetry, a master bedroom with en suite bath and two home offices, laundry and wine cellar. Enjoy the views of the gardens and orchard on 5+ bucolic acres while sitting in the library or formal dinning room. Currently decorated with antiques and a collection of European and American furnishings, bring your own treasures to fill this historic vessel. Chesterfield has convenient access to downtown Northampton, the Five colleges and the Berkshires, home to Tanglewood, The Clark, MASS MoCA . Take a journey to the Chesterfield Gorge and follow The Westfield River

Listed by Miriam Sirota of Jones Group REALTORS®

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

115 Indian Hollow Road, Chesterfield, MA

MLS Number 72377095

  • Single Family
  • Parking Spaces 6
  • Year Built 1984
  • Full Bath 2
  • Bathroom 2

Magnificent home located on the Dead Branch River astounds with a gorgeous stone fireplace that extends up the cathedral ceilings along with hardwood floors in both the living room and formal dining room. Large kitchen with island and a galore of storage space, playroom is the perfect get away, one bedroom with hardwood floors and a full bath complete the main floor. The second level remarks with two more bedrooms and a full bath. In the need for in law space or a guest house, here you have that unbelievable space with an additional 1800 sq.ft. home complete with kitchen, living and dining room, full bath, bedroom and a fabulous loft bedroom with deck overlooking scenic views. Large storage shed located outside. This home offers so much privacy with over 29 acres. Perfect retreat space!!!

Listed by The Denise DeSellier Team and Denise DeSellier of Real Living Realty Professionals, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

92 South Street, Chesterfield, MA

Price$340,000

Est. Mortgage: $/month

MLS Number 72420656

  • Single Family
  • Parking Spaces 6
  • Year Built 1972
  • Full Bath 2
  • Bathroom 2

This light filled home is very private with a lovely view over a gently sloping south lawn. Lovely Goshen stone patio overlooking the property leads to sliders into the living room or family room. Spacious kitchen that opens to dining/living area. 1st floor bedroom. 1st floor bath is nicely tiled. This spacious bathroom also has the laundry machines in it. Upstairs are two more spacious bedrooms, one has two walk in closets with organizers. Lovely bathroom with whirlpool bath and a separate shower stall. Hardwood floors throughout most of the house. Mudroom off of kitchen has plenty of room for your coats and boots. Beautiful grounds with a 3 stall barn/shed. This house started its life as a ranch back in 1972 but was completely remodeled and a floor added in 2003. Newer propane furnace and hot water heater. Easy and economical to heat. 20 minutes to Northampton makes for an easy commute.

Listed by Carla Ness of Delap Real Estate LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

114 Sugar Hill Road, Chesterfield, MA

Price$144,900

Est. Mortgage: $/month

MLS Number 72351270

  • Single Family
  • Parking Spaces 10
  • Year Built 1785
  • Full Bath 1
  • Bathroom 1

Beautifully settled on 46 acres of land this colonial house offers so much: privacy, space, character, history and more. The house will need major upgrades, but will shine with the right vision and planning. Build in the late 18th century, the house has still lots of original woodwork, wooden fireplace mantel and oversized granite fireplace with the crane. All this could be tastefully incorporated into new design. All rooms have separate fireplaces. Property is sold in “AS-IS, WHERE -IS” condition and only Cash or Rehab loans offers will be considered. Property has not been occupied for several years.

Listed by Andrzej Jamroga of Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

4 Willicutt Road, Chesterfield, MA

Price$112,000

Est. Mortgage: $/month

Price Changed

MLS Number 72431475

  • Single Family
  • Parking Spaces 1
  • Year Built 1910
  • Full Bath 1
  • Bathroom 1

Listing price is $ 166,100 . Here is your chance to own this cute single family home located in Worcester County. This home offers 2 bedrooms, and 1 full bathroom and was built in 1910. Home also features a living, dining, kitchen, fireplace and hardwood floors.

Listed by Nicole Gale of RealHome Services and Solutions, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Chesterfield, MA

Price$90,000

Est. Mortgage: $/month

MLS Number 72394025

  • Land Residential
  • Acreage 2

Move on up to the country! Two acre lot to be divided out of a larger parcel. Beautiful, level lot in Chesterfield center that is ready for your house plans! Just around the corner from the library, post office, skate park, playground and town hall. Just a couple miles from Chesterfield Gorge and only 25 minutes to Northampton Center! If you have been dreaming of country living, away from the hustle and bustle, then come on up and see what a lovely spot is awaiting you.

Listed by Linda Webster of Coldwell Banker Upton-Massamont REALTORS®

$
$
%
$/month over payments
Federal 30-year interest rate: 4.75% last updated on Dec 6, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.