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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

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26 Windy Lane Chesterfield MA 01084

Chesterfield, MA26 Windy Lane

Price$699,900

Est. Mortgage: $/month

Active With Contract

MLS Number 72840143

  • Single Family Detached
  • Bathroom 1
  • Rooms 6
  • Bedrooms 3
  • Acreage 166

This Circa 1768 Colonial Saltbox Home set on 166 Private Acres! The home has charm, character & nice open floor plan.The modern Country Kitchen. has Goshen Stone counters & Stainless Steel appliances.The Kit. fireplace had a wood stove hookup, but never used by current owner. The large Dining Area is open to the Kit. & LR. Spacious LR w/beamed ceiling & a wood burning fireplace is open to an office area and access to a wonderful screened porch. Large Master Bedrm is on the1st flr. Updated Bathrm is close by w/slate flooring, modern fixtures & built-ins. Up are 2 good size bedrms w/closets. The Breezeway betwn the House and Garage is also used as a Greenhouse.It has slate flooring, a gas heater and lots of natural light. The Slate Patio w/beautiful gardens is off the greenhouse.The 2 Car Garage has a huge finished room above it perfect for a studio,office or game rm.There is a 2/3 stall Horse Barn w/Tack Room & Hay Loft.Also a Rustic 1 bedrm. Cabin with 1/2 bath.Whole House Generator!

Listed by Dan Schachter of Canon Real Estate, Inc.

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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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.

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172 South Street Chesterfield MA 01012

Chesterfield, MA172 South Street

Price$595,000

Est. Mortgage: $/month

MLS Number 72868098

  • Single Family Detached
  • Bathroom 3
  • Rooms 7
  • Bedrooms 3
  • Acreage 11.41

Builder's own custom built cape style house on over 11 private, wooded acres is in move in condition. The wide pine floors throughout have just all been refinished. The large eat in kitchen has plenty of cabinets with a nice big pantry. Native stone fireplace in family room is located just off the kitchen. The rear deck goes the entire length of the house. Full basement has 2 finished rooms plus laundry. 3 nice sized bedrooms are upstairs and the master has 2 large walk in closets and en-suite bath with beautiful claw foot tub. Unique antique dressers repurposed as bathroom vanities in both 2nd floor baths. The open front porch spans the width of the house. The post & bean 28 x 42 barn has 3 garage stalls underneath and is perfect for your hobby or business on the main level.

Listed by Kathleen Borawski of Borawski Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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.

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1 River Chesterfield MA 01084

Chesterfield, MA1 River

Price$479,900

Est. Mortgage: $/month

MLS Number 72859275

  • Single Family Detached
  • Bathroom 2
  • Rooms 8
  • Bedrooms 3
  • Acreage 6

Supreme, spacious log home constructed on site & the quality beckons you. Grand rooms, amazing brick fireplace on both levels. Great for entertaining-open concept quartz counter kitchen, dinette & pass thru to the grand cathedral living rm. Picture yourself below the stars in your outdoor private spa, or cozied up in front of the fire, sit back with a good book, or take to the outdoors! This treasure of a home has it all. Location: Wow! Hiking, fishing, biking, snowmobiling, riding trails for all. Short distance to the town beach "town bend' & the gorge. Abuts 4 Seasons club land & MA state land, close to Westfield river. Welcome to the place where convenience and your private paradise meet. (High speed internet, just 23 min.to Northampton, or 40 min to either Westfield or Pittsfield & yet woodland privacy, sounds of nature & the rustic seclusion we all dream of). Its your own private paradise. Out buildings, fenced corral, small private pond & more.

Listed by Nadine Hiser of Key Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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.

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388 Main Road Chesterfield MA 01012

Chesterfield, MA388 Main Road

Price$447,000

Est. Mortgage: $/month

MLS Number 72825836

  • Single Family Detached
  • Bathroom 3
  • Rooms 9
  • Bedrooms 5
  • Acreage 2

This meticulously maintained home on 2 acres of land is not to be missed. The sellers spent years restoring, improving & rebuilding this Farm House w/ attached apartment/in-law suite. The 1st floor enjoys a custom kitchen w/ adjoining dinning area, large living room, 1st floor laundry w/ bath & attached therapeutic spa room just off the back. Second floor master w/ plenty of closets & French doors to 2nd bedroom, bath w/ soaking tub, 3rd bedroom, & a bonus room. The adjoining apartment has a heated 1 car garage & has shown great rental history at $1,400 a month. This would make a wonderful private in-law or extended family suite. Some of the improvements (apo) are roof, well, solar is owned w/credits ($3k+/- a year), wired for a whole house propane generator, 2 furnaces; 1 is a pellet, covered deck (great for barbecuing), wrap around front porch, central AC, wood-sided heated pool, spray foam insulation, updated plumbing, electrical, & 3 bay propane heated garage.

Listed by Maple and Main Realty, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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.

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388 Main Road Chesterfield MA 01012

Chesterfield, MA388 Main Road

Price$447,000

Est. Mortgage: $/month

MLS Number 72825837

  • Multi-Family 2 Family
  • Total Parking Spaces 8
  • Year Built 1900
  • Bathroom 3
  • Full Bath 3

This meticulously maintained home on 2 acres of land is not to be missed. The sellers spent years restoring, improving & rebuilding this Farm House w/ attached apartment/in-law suite. The 1st floor enjoys a custom kitchen w/ adjoining dinning area, large living room, 1st floor laundry w/ bath & attached therapeutic spa room just off the back. Second floor master w/ plenty of closets & French doors to 2nd bedroom, bath w/ soaking tub, 3rd bedroom, & a bonus room. The adjoining apartment has a heated 1 car garage & has shown great rental history at $1,400 a month. This would make a wonderful private in-law or extended family suite. Some of the improvements (apo) are roof, well, solar is owned ($3K credit +/- a year), wired for a whole house propane generator, 2 furnaces; 1 is a pellet, covered deck (great for barbecuing), wrap around front porch, central AC, wood-sided heated pool, spray foam insulation, updated plumbing, electrical, & 3 bay propane heated garage.

Listed by Maple and Main Realty, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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.

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Lot 14 Bissell Road Chesterfield MA 01012

Chesterfield, MALot 14 Bissell Road

Price$274,000

Est. Mortgage: $/month

MLS Number 72757577

  • Land Residential
  • MLS Status Active
  • Acreage 60.21

Large 60+ acre parcel with 610 feet of frontage and two separate perk locations in a quiet, rural setting. Located in Chesterfield, MA in the foothills of the Berkshires, this land enjoys beautiful fall colors, stone walls and abundant wildlife while being only 20 minutes to Northampton shopping. Land is gently sloping and level, containing a flat spot at the high elevation point ideal for privacy and homesteading. Building lot requirements in Chesterfield include 2 acres and 200 feet of frontage. Accessory/in-law apartments are allowed by right or special permit. Broadband internet is currently being installed throughout the town. Additional land available: 21+ acres with 1,683 feet of frontage on two town-maintained roads with 4 separate perk locations. Builder tie-in and design services available.

Listed by Darin Thompson of Stuart St James, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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 TourAsk A QuestionMore Details

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