and narrow your search. If you have fewer than 200 results, you can save your search.

Hilltowns Real Estate

The Hilltowns of the Pioneer Valley of Western Massachusetts include the towns of: Ashfield, Becket, Buckland, Charlemont, Chester, Chesterfield, Colrain, Conway, Cummington, Goshen, Hawley, Haydenville, Heath, Huntington and more!  

Browse Real Estate in the Hilltowns of the Pioneer Valley

Scroll down to search all Hilltowns, MA real estate. Register to save your favorite listings, save your searches of 200 or fewer listings, and receive notification when a new property matches your search criteria! Questions about buying a Hilltown home? Contact us today- we're here to help.

Want to start your search from scratch? Use our advanced search tool.

Colrain, MA

Price$2,000,000

Est. Mortgage: $/month

MLS Number 72160429

  • Land Agricultural
  • Acreage 321

Enjoy your Summer, end of the year foliage or winter surrounded by greens and tranquility.This land would be perfect for someone who wants to escape City traffic and enjoy the seasons and it's attractions including Covered Bridges, fishing, and skiing . Many walking trails and the lake filled with fish. 500.65 acres of land in the price included. The whole package consists of 6 separate Deeded lots selling as one package. See remarks for lot's identifications included in the package. SF house on 48 Call Rd. is included in the sale, built in 1980 it was not occupied in last 2 years. It is Sold As Is/ Where Is condition. Berkshire East ski resort and other attractions just 10 minutes away. Currently there is no access to the house. Subject property is under Chapter 61 with

Listed by Andrzej Jamroga of Keller Williams Realty

{$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

80 Bardwells Ferry Road, Shelburne, MA

Price$1,600,000

Est. Mortgage: $/month

MLS Number 72073623

  • Single Family
  • Bathroom 5
  • Full Bath 4
  • Bedrooms 4
  • Year Built 1812

In a most desirable location, this classic gentleman's equestrian farm, beautifully located on a quiet country road offering 61 acres of private space on both sides of the road. This handsome Asher Benjamin designed 1812 Colonial has been impeccably restored with no expense spared. Fireplaces, game room, wine cellar and a complete modernization of mechanical systems makes this a pleasure. The solarium hails from England. The pool house, which can be a separate guest house with kitchen, bath and living space, heat and AC, overlooks the in-ground pool and rolling fields. An 8 stall horse barn with radiant heat and a riding arena with rubber and sand footing is every horse owner's dream.For the buyer looking for boat or car storage, this would be ideal. A grand property for the discriminating buyer who will be impressed.

Listed by Mary Lou Emond of Cohn & Company

{$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

103 Webber Road, Whately, MA

Price$1,195,900

Est. Mortgage: $/month

MLS Number 72146601

  • Single Family
  • Bathroom 4
  • Full Bath 2
  • Bedrooms 4
  • Year Built 2008

Enjoy a private panoramic view of Mt. Sugarloaf, Mt. Toby and the entire valley from this hilltop arts and crafts /prairie style custom built contemporary. Main level features a gourmet kitchen with dining area, formal dining room with built in china cabinet, a living room with fireplace, built in bookcases, media center, piano alcove and private screen porch. There is also half bath in the entry foyer. The master bedroom suite includes two walk in closets and dressing areas, private bath with double vanity, separate jetted tub, tile shower and an attached den/media room. Off the kitchen there is a home office, laundry, mudroom, half bath and covered deck. The lower level is walkout through a covered porch to the front yard that also enjoys the same panoramic view; its features include a family room with fireplace and built in bookcases, library alcove, three bedrooms and the 2nd full bath. The state of the art propane heating system offers multiple zones as does the central air.

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

{$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

298 Barnes Road, Ashfield, MA 01330

MLS Number 72217479

  • Commercial
  • Year Built 1994

This is the prettiest golf course nestled in one of the most beautiful valleys in the Berkshire foothills. At one time a working dairy farm, Edge Hill Golf Course was established in 1994 with 9 holes and expanded to 18 holes in 2014. These newer holes are some of the most innovative and offer the most spectacular views of the course.The old dairy barn has been converted into a golf shop and snack bar with a large covered patio overlooking the large pond. Great site for weddings and events with a remodeled barn featuring a commercial kitchen. Bring your clubs and come up to play a round to see what a special property this is.

Listed by Phil Pless 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

124 Skyline TRAILL, Chester, MA

Price$875,000

Est. Mortgage: $/month

MLS Number 72210790

  • Single Family
  • Bathroom 2
  • Full Bath 2
  • Bedrooms 3
  • Year Built 2004

Spectacular custom post and beam home! Wonderful joinery and unique design. Bright, light and open floor plan, cathedral ceilings, first floor bedrooms, exquisite master suite, radiant heat throughout, stone fireplace, lovingly landscaped and cared for, 16 acres of forest, walking trails, and privacy.

Listed by Maureen White Kirkby of Barnbrook Realty Corp.

{$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

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 Karen Dunn and Luke Dunn 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

200 Avenue A, Montague, MA 01376

MLS Number 71762709

  • Commercial
  • Year Built 1959

This commercial building currently has two retail long term lease tenants, Aubuchon Hardware and Family Dollar; Located in the downtown Turners Falls shopping center offering great exposure, ample parking and separate road access to rear loading docks. New roof in 2010 and otherwise well maintained.

Listed by Michael Pratt 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

67 Roberts Road, Shelburne, MA

Price$599,000

Est. Mortgage: $/month

MLS Number 72248526

  • Single Family
  • Bathroom 3
  • Full Bath 3
  • Bedrooms 6
  • Year Built 1780

Just imagine overlooking these magnificent million dollar views of the horizon’s sunrise and sunsets that include Mt. Monadnock and an impressive display of mountain ranges. The renovated 1780 antique Colonial on 5 acres was once known as the Roberts School is 5400sqft and is currently a two family home. It features 13 rooms, 6 bedrooms, 3 baths, 2 kitchens, 20x40 great room and a billiard room. The grounds are spectacular with an in-ground pool, vineyard, sleeping cabin, stone patios, basketball court all surrounded by majestic maple trees and gorgeous open meadows. It is conveniently located only 5 minutes to I-91 and Shelburne Falls, 30 minutes to Northampton and surrounded by plenty of recreational activities. Call today for details and set up a showing appointment!

Listed by Wanda Mooney 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

67 Roberts Road, Shelburne, MA 01370

Price$599,000

Est. Mortgage: $/month

MLS Number 72248527

  • Multi-Family 2 Family
  • Bedrooms 6
  • Year Built 1780

Just imagine overlooking these magnificent million dollar views of the horizon’s sunrise and sunsets that include Mt. Monadnock and an impressive display of mountain ranges. The renovated 1780 antique Colonial on 5 acres was once known as the Roberts School is 5400sqft and is currently a two family home. It features 13 rooms, 6 bedrooms, 3 baths, 2 kitchens, 20x40 great room and a billiard room. The grounds are spectacular with an in-ground pool, vineyard, sleeping cabin, stone patios, basketball court all surrounded by majestic maple trees and gorgeous open meadows. It is conveniently located only 5 minutes to I-91 and Shelburne Falls, 30 minutes to Northampton and surrounded by plenty of recreational activities. Call today for details and set up a showing appointment!

Listed by Wanda Mooney 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

21 Laurel Mountain Road, Whately, MA

Price$554,000

Est. Mortgage: $/month

MLS Number 72211393

  • Single Family
  • Bathroom 6
  • Full Bath 5
  • Bedrooms 6
  • Year Built 1986

Inviting 6 BR, 5.5 bath Contemporary with flexible living areas - great for an extended family or potential B&B. Many extras include the fully enclosed gazebo with a hot tub and wood stove for relaxing year round; a 30 X40 two story barn/workshop for potential home business or farm animals; oversized attached 2 car garage; 400 amp electric service (with underground service to barn and gazebo); new 6 zone Buderus heating system. House is located on 22 private acres, adjacent to state owned property, but only 15 minutes to Northampton. A must see!

Listed by Janice Kynard 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.

Virtual TourSave 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.