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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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416 Main Road, Chesterfield, MA

Price$699,000

Est. Mortgage: $/month

MLS Number 72080313

  • Single Family
  • Bathroom 4
  • Full Bath 3
  • Bedrooms 5
  • Year Built 1822

This icon of American Federal style architecture offers the discerning buyer a rare opportunity to purchase a historic residence that has remained in a single family since 1822. Built by Dr. Robert Starkweather (1765-1858),who practiced medicine in Chesterfield for over 50 years,this beautiful center hall Colonial features many finely preserved period details,including a hipped roof, symmetrical windows, fluted pilasters, a fan light over the front entrance,2 chimneys,8 fireplaces,high ceilings,beautiful original moldings and wide-plank hardwood flooring. While maintaining its historic integrity and character,this home has been tastefully updated with a modern kitchen containing custom cherry cabinetry and French doors to the spacious dining room and library affording beautiful views of the gardens,orchard and hay field. Situated on 5+ acres,this spacious 14 room house offers convenient access to Northampton,the 5 college area includes many nearby cultural and recreational facilities.

Listed by Stiles & Dunn, Karen Dunn and Luke Dunn of Jones Group REALTORS?

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Maple and Main Realty
28 North Maple Street
Florence MA, 01062
Office: 413.584.2900

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$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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115 Indian Hollow, Chesterfield, MA

Price$475,000

Est. Mortgage: $/month

MLS Number 72244407

  • Single Family
  • Bathroom 2
  • Full Bath 2
  • Bedrooms 3
  • Year Built 1984

Located off Indian Hollow Road at the end of a private drive you will find this country retreat on 29 private acres with a beautiful western view and frontage on the Dead Branch River. The main house first floor features a living room with two story stone fireplace, family room with spectacular views, formal dining room, large kitchen, playroom, bedroom, sun porch and full bath. Upstairs are two more bedrooms and a second full bath. The main house also has two decks and a full basement for utilities and laundry. Outside there is a good sized shed with an annex for firewood storage. The 1800 square foot guest house has an open first floor with large kitchen, living and dining area, full bath, bedroom and utility room. Upstairs is a huge loft bedroom with a deck overlooking the valley. This unique property would make either a wonderful primary residence or fantastic get away home with on site caretaker.

Listed by David A Murphy of The Murphys REALTORS?, Inc.

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Maple and Main Realty
28 North Maple Street
Florence MA, 01062
Office: 413.584.2900

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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206 Bryant Street, Chesterfield, MA

Price$399,000

Est. Mortgage: $/month

MLS Number 72319849

  • Single Family
  • Bathroom 3
  • Full Bath 2
  • Bedrooms 3
  • Year Built 2008

Immaculate contemporary home on 17.22 bucolic acres in the heart of beautiful Chesterfield MA. This 3 bedroom, 2.5 bath has all the bells & whistles! Open concept floor plan on first floor w/large cook's kitchen, wood stove, dining room, family room and TV room, shaded porch and sunny deck, tiled mudroom and office/guest room across from first floor powder room. Second floor is comprised of a gracious master suite, w/a large walk-in closet, 2 additional bedrooms and addt'l full bath/laundry room. Walk out basement is ready to be finished, or can be used as-is. There is also a large walk up attic with ample storage space. In the spacious yard, you will find a large storage shed, fire pit, stone walls and plenty of wildlife. 12 minutes to Wmsburg, 20 to Florence, 26 to Northampton ctr. Camping, hiking, skiing, fishing, horseback riding and all that Chesterfield & the hill towns have to offer - as well as an abundance of cultural events and natural beauty in the nearby Berkshires.

Listed by Julie Starr of Maple and Main Realty

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Maple and Main Realty
28 North Maple Street
Florence MA, 01062
Office: 413.584.2900

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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185 Sugar Hill Road, Chesterfield, MA

Price$279,000

Est. Mortgage: $/month

MLS Number 72306128

  • Single Family
  • Bathroom 2
  • Full Bath 1
  • Bedrooms 2
  • Year Built 2006

Beauty, energy efficiency, and mindfulness begin to describe the care and thoughtful efforts that have gone into this wonderful home. Vaulted ceilings throughout, custom carved cherry cabinet doors, custom concrete counters accented by appliances that are attractive and offer special safety features. The beauty and comfort of the tile flooring is warmed by both the radiant heating system and the circulating passive solar design features keeping your stocking feet warm and comfortable year round. The sun space is spectacular with a vented suspended slab designed to circulate the warm air. There are 2 bed rooms with the master having a walk in/through closet that accesses the the over sized bath offering a large tiled shower stall, separate free standing tub with bright tile surround. Basement includes high ceilings and is ready for further finishing having a half bath that is set for a shower. Other features include a great entry room, screen porch, whole house generator, more.

Listed by James A. Molyneux of Molyneux Realty

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Maple and Main Realty
28 North Maple Street
Florence MA, 01062
Office: 413.584.2900

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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62 Willicutt Road, Chesterfield, MA

Price$259,000

Est. Mortgage: $/month

MLS Number 72092609

  • Single Family
  • Bathroom 1
  • Full Bath 1
  • Bedrooms 1
  • Year Built 1900

PRICE REDUCTION!! Cash or 203 REHAB loan is the way to purchase this lovely property. LOTS OF LAND!! Wonderful opportunity to own property that insures privacy as it encompasses both sides of Willicutt Road. Roughly 2000 feet of running road frontage. 85 acres +/- are on the barn side of road with a newer perc test. Gorgeous open meadow with barn (perfect for home in your future to be built). Current home (which is in need of finishing renovations) is on 5+ acres and has passed Title V testing. Beautiful long range views from the ledges above the house with easy drive access already in place. Perfect spot for a future home. On the barn side property (85+/- acres) there are many many open field acres, recently done perc test and then gorgeous woods. This is a fabulous price for this property. Come see if this property will work for you.

Listed by Nancy Merritt of Delap Real Estate LLC

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Maple and Main Realty
28 North Maple Street
Florence MA, 01062
Office: 413.584.2900

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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21 Farmhouse Road, Chesterfield, MA

Price$189,000

Est. Mortgage: $/month

Open House

MLS Number 72329011

  • Single Family
  • Next Open House: Sun 27th 10:00 am - 12:00 pm
  • Bathroom 1
  • Full Bath 1
  • Bedrooms 2

In the foothills of the Berkshires, on beautiful Lake Damon, sits this sweet seasonal cottage awaiting a new family to begin a new chapter. Sitting in one of the more private spots on the Lake, this property may be the perfect location to build a new cottage from scratch. Or, take this existing cottage and customize it to your liking. Lake Damon is a private lake with no public access and no gas motors allowed, making for peaceful days and tranquil nights. Enjoy being one with nature as you admire the many species of birds and aquatic life that make Lake Damon home. At night, enjoy star filled skies, as you sit around your campfire, toasting marshmallows and making lifelong memories with family and friends. Fish from the dock, kayak the lake or walk over to the association beach and playground so that kids can meet up with friends. Sold As is. All offers considered!

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

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Maple and Main Realty
28 North Maple Street
Florence MA, 01062
Office: 413.584.2900

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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Chesterfield, MA

Price$98,500

Est. Mortgage: $/month

MLS Number 72263129

  • Land Residential
  • Acreage 25.72

Your own beautiful paradise awaits! Just around the bend from the Westfield River sits this gorgeous piece of land on a quiet but publicly maintained dirt road, right across the street from state forest land. Walk up the south-facing gentle sloping hill of this 25 acre plot to see a potential for gorgeous views, old stone walls, and tranquility. With enough road frontage, there is also the potential for two separate building lots with plenty of space for privacy. Come take a look, you won't be disappointed!

Listed by Sarah Shipman of Jones Group REALTORS?

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Maple and Main Realty
28 North Maple Street
Florence MA, 01062
Office: 413.584.2900

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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 2 B Munson Road, Chesterfield, MA

Price$42,000

Est. Mortgage: $/month

MLS Number 72292438

  • Land Residential
  • Acreage 5.56

5.56 acre lot - perc test done--several spots which to build--- Gorgeous elevated sunset views potential toward back of lot with some clearing... 180 degree views. Secluded quiet setting with stone wall. An additional lot( 3.65 acre) is also available on this quiet road. Partially paved, part dirt road. Chesterfield is a lovely hill town with all of the the charms of the country, yet just a 20- 25 minute drive to Northampton. Priced well below assessed value to sell !

Listed by Amy E. Coyne of Adams Realty

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Maple and Main Realty
28 North Maple Street
Florence MA, 01062
Office: 413.584.2900

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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 1 Indian Hollow Road, Chesterfield, MA

Price$39,900

Est. Mortgage: $/month

MLS Number 70967254

  • Land Residential
  • Acreage 2

To be surveyed from larger parcel and perc tested by seller. 2.0 Wooded acre "Get away" location. Convenient to Williamsburg Center, and Northampton.

Listed by Wentworth Miller Team of Jones Group REALTORS?

{$agent->Name}

Maple and Main Realty
28 North Maple Street
Florence MA, 01062
Office: 413.584.2900

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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135 East Street, Chesterfield, MA

Price$32,500

Est. Mortgage: $/month

MLS Number 72298970

  • Land Residential
  • Acreage 2.64

The interesting terrain and rock outcroppings will add a challenge to the site design, but the convenient location, nice neighborhood and natural beauty of the lot will more than compensate. An affordable lot offering the opportunity to build the home of your dreams.

Listed by Michael Packard of Coldwell Banker Upton-Massamont REALTORS?

{$agent->Name}

Maple and Main Realty
28 North Maple Street
Florence MA, 01062
Office: 413.584.2900

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

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