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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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345 Ireland Street Chesterfield MA 01084

Chesterfield, MA345 Ireland Street, West Chesterfield

Price$810,000

Est. Mortgage: $/month

Price Changed

MLS Number 73377957

  • Residential
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,907

This is the place where dreams come true! A large 3 bed/2.5 bath modern home, classic 2 stall barn with hayloft and insulated, heated 30x50 garage/barn w/ 16' ceilings on nearly 70 acres. Just 30 mins from Northampton this idyllic setting features bucolic views, open green fields and woods with stone walls and winding trails that lead to Jackson's Brook. A contemporary home with warm traditional accents offers easy living w/ 2-car attached garage,1st fl suite & laundry, ample storage & mini-splits. Open concept main level has wood floors, gas fireplace and a custom kitchen. Upstairs includes a generous flex room with large west-facing windows perfect for enjoying sunsets. A year round sun porch, indoor hot tub, cabana, clubhouse and spacious yard elevate your private oasis. Imagine the possibilities…farm, homestead, animal sanctuary, workshop, home business, your own retreat…or explore passive rental income potential for the out-buildings & pasture. An incredible opportunity and value.

Listed by Lisa Carroll of Delap Real Estate LLC

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$/month over payments
Federal 30-year interest rate: 6.67% last updated on Jul 3, 2025
* 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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330 East Street Chesterfield MA 01096

Chesterfield, MA330 East Street

Price$799,900

Est. Mortgage: $/month

MLS Number 73400387

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,922
  • High School Hampshire Reg.

Nestled on over 70 acres of natural beauty just over the Westhampton border, this nearly 3,000 sq ft custom-built home offers privacy, peace, and thoughtful design throughout. Large southern-facing windows capture mountain views, while the open floor plan flows seamlessly from the kitchen to living and dining areas. Radiant floor heat, tile floors, and a sunroom enhance comfort year-round. Whether you're drawn to the serenity, oversized garage with incredible storage and ADU potential, or just stargazing from the hilltop, this home lives like your own private retreat. Designed with non-toxic materials, commercial-grade HVAC w/ fresh air intake, and multi-stage water filtration, it also offers exceptional air & water quality. Other features include heated walk, generator, durable metal roof & Hardie-board siding, offering practical convenience. Hike out your back door or simply enjoy the quiet-this property is ideal for anyone seeking a healthy lifestyle or a secluded escape in nature!

Listed by Jill Vincent Lapan of Canon Real Estate,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Jul 3, 2025
* 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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510 Main Road Chesterfield MA 01012

Chesterfield, MA510 Main Road

Price$669,000

Est. Mortgage: $/month

MLS Number 73390361

  • Residential
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 1,908

Incredible opportunity to personalize a nearly new construction! This home is undergoing a complete transformation-only the original first-floor framing remains. A full second-floor addition and full interior rebuild are in progress. Now framed with rough plumbing and electrical underway, this is the ideal time for a buyer to select finishes and add personal style. The second floor will feature a spacious primary suite with a large walk-in closet and full bath, plus two additional generously sized bedrooms, another full bathroom, and laundry. The first floor boasts an open-concept design blending the brand-new kitchen with the living room, perfect for entertaining. Just off the kitchen, enjoy a walk-in pantry, laundry room, and a convenient half bath. A large first-floor bedroom with a walk-in closet and its own full bath offers flexible living options. With 4 bedrooms and 3.5 baths, this home offers modern design and room to grow-your vision, your future home.

Listed by Daniel James Piasecki of Coldwell Banker Community REALTORS®

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Jul 3, 2025
* 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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31 Farm House Road Chesterfield MA 01012

Chesterfield, MA31 Farm House Road, West Chesterfield

Price$439,000

Est. Mortgage: $/month

MLS Number 73360141

  • Residential
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,024
  • High School Hamp Regional

It's HOT -buy a lake house! Escape to serenity with this charming lakefront cottage, 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 ideal for casual meals and entertaining family and friends. Step outside to your private dock, a fantastic spot to unwind by the water, cast a line for fishing, or launch your canoe/kayak for peaceful paddles around the lake. Whether you're looking to relax by the water or explore the great outdoors, this home offers the perfect haven. Don't miss this exceptional opportunity to own your piece of lakefront paradise. Schedule your showing today and experience the magic of this year-round retreat! …and no flood insurance needed (APO).

Listed by Shelly Hardy of Brick & Mortar Northampton

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Jul 3, 2025
* 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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141 Ireland Street Chesterfield MA 01096

Chesterfield, MA141 Ireland Street, West Chesterfield

Price$199,000

Est. Mortgage: $/month

MLS Number 73378205

  • Land
  • Acreage 20
  • Zoning RA
  • Neighborhood West Chesterfield

Beautiful mostly wooded 20 acres of land with views near the Chesterfield Gorge. Easy access to rt 143 to rt 9. There 3,536 sq foot house and three car garage that needs extensive renovations. Buyer and Buyers Agent to do their due diligence.

Listed by Michelle Bond of Coldwell Banker Community REALTORS®

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Jul 3, 2025
* 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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0 Pynchon Road Chesterfield MA 01012

Chesterfield, MA0 Pynchon Road

Price$179,000

Est. Mortgage: $/month

MLS Number 73402258

  • Land
  • Acreage 4
  • Zoning all pa

Rare water front lot on Damon Pond. Clearing needed to obtain a year round view of the pond. Lot is perc tested, surveyed with electric service contracted to be delivered this summer. Join the association and have access to the recreation and beach area. NO power boating but kayaking, canoeing, fishing. 25 minutes to Northampton. Year round recreational living in a quiet private setting.

Listed by James A. Molyneux of Molyneux Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Jul 3, 2025
* 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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