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, Worthington 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.

184 Cudworth Worthington MA 01098

Worthington, MA184 Cudworth

Price$3,500,000

Est. Mortgage: $/month

MLS Number 72751067

  • Single Family Attached
  • Bathroom 8
  • Rooms 13
  • Bedrooms 4
  • Square Feet 14,240

This outstanding private and spacious estate is set on 12.1 beautifully landscaped acres offering just over 14,000 square feet of quality living area. The unique 5 bedroom, 5 full bath/3half bath main house includes an in-law apartment/guest quarters and an Olympic sized indoor/heated pool. Top grade appliances are another important feature. Dark walnut hardwood flooring runs throughout the main house as does a state-of-the-art radiant heating system. Other special features include Vantage lighting, a large game room and home office, a steam shower and overflow tub in the master bath, a humidification system, an indoor/outdoor intercom system, and a full house commercial generator. The horse barn also includes a 3 bedroom guest quarters, and a significant fireproof walk-in vault.

Listed by George Cain of William Pitt Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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

82 Chestnut Hill Loop Montague MA 01351

Montague, MA82 Chestnut Hill Loop

Price$1,950,000

Est. Mortgage: $/month

MLS Number 72749325

  • Single Family Detached
  • Bathroom 2
  • Rooms 9
  • Bedrooms 4
  • Square Feet 2,684

Antique farmhouse on 419 Acres with Trout Pond and Barns Welcome to Redbrook Farm The quintessential New England farmhouse tucked amidst one of the largest private land holdings in the Commonwealth being offered today. Beautiful Chestnut Timber construction with wide plank flooring and open concept kitchen to living area. Unparalleled historic charm with today's conveniences making this a truly special offering. 4 bedrooms, 2 baths and two barns complimented by fenced grazing land for whatever one wishes to home. The backlands are accessed by wonderful trails for your hiking, biking or snowshoeing exploration. Less than two hours to Copley Square and 3 hours to NYC makes this a wonderful reprieve from the city or full time residence for those commuting to the 5 college area in under 25 minutes or Springfield in just 45 minutes.

Listed by Jeffrey Loholdt and Herbert Butzke of William Pitt Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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

52 Upper Bryant Road Cummington MA 01026

Cummington, MA52 Upper Bryant Road

Price$1,625,000

Est. Mortgage: $/month

MLS Number 72771275

  • Single Family Farm
  • Bathroom 1
  • Rooms 12
  • Bedrooms 4
  • Square Feet 5,306

290+ Acre, 4th Generation Farm and former uplands of the William Cullen Bryant HomesteadFourth generation working family farm with Impeccable views of the Westfield River Valley and beyond. Located in rural Western Massachusetts in the town of Cummington, this picturesque setting is equidistant to the Berkshires and Northampton areas for most of what anyone could ever desire. Very rich in history, this one of kind property is part of the original William Cullen Bryant farm and estate dating back to the 1800's. The upper Bryant farm was built in 1871 by William Cullen Bryant for his eldest daughter Frances (1822-1893). In most recent years, the current owners have begun renovating the 5000+ sqft antique home with a new roof, siding and trim, windows, kitchen, bath, and the caretaker's quarters started. New furnace installed January 2021 for main level of home. Welcome home.

Listed by Jeffrey Loholdt of William Pitt Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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

455 Mathews Road Conway MA 01341

Conway, MA455 Mathews Road

Price$1,300,000

Est. Mortgage: $/month

MLS Number 72744452

  • Single Family Detached
  • Bathroom 4
  • Rooms 16
  • Bedrooms 5
  • Square Feet 4,269

This historic Dutch Gambrel on 35 acres of private countryside offers space, privacy and proximity.The elegant foyer welcomes you to this lovingly maintained home.The main level includes library with fireplace, living room with built ins, fireplace & pocket doors to the formal dining room with original wainscoting, crown molding and fireplace. The heart of the home, the open concept kitchen & family room enjoy a cozy wood stove. Pantry, laundry, studio space and "work from home" office complete the first level. The second level consists of the primary bedroom with lots of closets and fireplace, three generous bedrooms, renovated bath with double vanity, tiled shower & claw foot tub, additional bath and a lovely alcove. Apartment with separate entrance for guests, au pair or combine for additional living space.Enjoy the garden areas, porches & patio or walking trails, open fields.This beloved home is a special property, a rare opportunity, minutes to major routes for easy commute.

Listed by Cynthia O' Hare Owens and Aisjah Flynn of 5 College REALTORS®

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

138 D Ridge Road Worthington MA 01098

Worthington, MA138 D Ridge Road

Price$899,500

Est. Mortgage: $/month

MLS Number 72632379

  • Single Family Detached
  • Bathroom 6
  • Rooms 10
  • Bedrooms 4
  • Square Feet 4,370

Owner will consider all "serious" offers for both house and all acreage at a discounted price. Overlooking the 8th Fairway is this Rare Opportunity to own this 5+ acre estate. This home will be completed to builders specs to be a spectacular turn key, move in, Dream Home.Home was built to be a showpiece in the foothills of the Berkshires however it was never completed, This allows you the option to choose Kitchen bath and flooring to be finished to your taste and style. Home is set up as a 10 room home with 4 bedrooms and 3 baths consisting of nearly 6,000 square feet of living space. The third floor has an additional 1,500 sq.ft. with 6 dormers, for 3-4 more bedrooms. There is an attached 3 car garage as well. . Beautiful views of the golf course and the distant hills. Please do not go on property without the seller or Broker James Adams.

Listed by James Adams of Hilltown Real Estate by Adams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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

133 Old Post Road Worthington MA 01098

Worthington, MA133 Old Post Road

Price$855,000

Est. Mortgage: $/month

MLS Number 72629610

  • Single Family Detached
  • Bathroom 4
  • Rooms 12
  • Bedrooms 4
  • Square Feet 4,922

On a beautiful 9 acre stretch of land in picturesque Worthington, your dream home is waiting for you! Custom built 4 bed, 3.5 bath outfitted with state of the art Viking SS appliances and a Viessmann boiler system. Idealistic views from the wrap-around porch include bountiful fruit trees, a pond, and expansive forests. Once inside you will be welcomed by comfort and elegance of the formal dining room, a cozy living room with a fireplace, chef's dream kitchen, first-floor master and relaxing sunroom that you will never want to leave. Not to be outdone, the second floor boasts another master suite, family room, and 2nd fireplace, 2 more spacious bedrooms, 2 full baths, and great room for endless entertainment. There are all the luxuries of a wet bar, wine fridge, and movie theater size projector, and screen inside, which sits over the 4 car garage. The many decks help you take in the breathtaking landscape which includes a 2-story 40x70 barn with endless possibilities. Welcome home!

Listed by Meghan McCormick of Goggins Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

1-5 State Street Buckland MA 01338

MLS Number 72528540

  • Commercial
  • Total Parking Spaces 10
  • MLS Status Active
  • Year Built 1877

The Crown Jewel of Shelburne Falls, the iconic Oddfellows Hall, is available for the first time in over 40 years. Lovingly restored and maintained, this building has had numerous significant upgrades and has no deferred maintenance. Recently painted, re-wired, re-plumbed, membrane roof, 2 newer boilers and newer HVAC on first floor. Three full floors of retail and office space. First and second floor are handicap accessible. First floor lease has 6 years remaining. There are 7 professional offices on the second floor. Third floor is the Bridge of Flowers Business Center, a shared co-working space with various working options available. Excellent rental history, minimal vacancies. Located directly across from the Green Iron Bridge; a National Historic landmark Building overlooking the Deerfield River and the internationally acclaimed Bridge of Flowers in the Village of Shelburne Falls, Massachusetts.

Listed by Mark Abramson and Phil Pless of Coldwell Banker Community REALTORS®

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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

14 Watson Road Ashfield MA 01330

Ashfield, MA14 Watson Road, Watson

Price$799,000

Est. Mortgage: $/month

MLS Number 72759723

  • Single Family Detached
  • Bathroom 1
  • Rooms 9
  • Bedrooms 4
  • Square Feet 2,291

This wonderful 4 bedroom, one bath home in the Watson area of Ashfield is where you need to be. This rare,one of a kind home built circa 1803 is a remarkable gem, full of history and built with care and pride. The doors, down to the hinges were custom made by a blacksmith. The wood all custom notched. Meticulously built and lovingly cared for by the same family for generations.This gorgeous estate offers over 20 acres of plus land with 1674 feet of frontage. This post and beam home features wide planked spruce flooring, cabinets, walls, and vanities made from reclaimed wood. Additional features include a large barn with rooms and lofts ideal for that artist in the family. The water for the home is provided from a deeded natural spring. The home offers 5 fireplaces, including one with a baking oven. This home is ideal for the equestrian lover with nearby parks with miles of trails for riding. THIS ESTATE OFFERS THE VERY FEW REMAINING BUILDABLE LOTS IN TOWN. Contact broker for plot plan

Listed by Robert Pelfrey of Easton Real Estate, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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

292 Main Street Ashfield MA 01330

Ashfield, MA292 Main Street

Price$795,000

Est. Mortgage: $/month

MLS Number 72698065

  • Single Family Detached
  • Bathroom 6
  • Rooms 16
  • Bedrooms 6
  • Square Feet 4,500

This amazing Queen Anne house is filled with creativity and joy. Each room is unique, with large parlors suitable for house concerts, workshops and more. This home has been host to hundreds of phenomenal events. There are four full floors of usable space for almost anything you can imagine. The large finished basement housed a successful business with many employees, having both office and warehouse space. This is an excellent property for families, groups or a small business and it is a pleasure for entertaining. The mechanical systems have been upgraded to current standards. The open 3+ acre parcel in town abuts the Ashfield Community Golf Course and the property features beautiful gardens, a fantastic studio space and a sauna. Formerly the summer residence of the town benefactor Milo Belding and later The Adelphi Inn. The Ashfield Lake is nearby with it's relaxing beach, tennis courts and playground/picnic area. Come see this remarkable home, you're in for a treat.

Listed by Phil Pless of Coldwell Banker Community REALTORS®

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

719 Barnes Road Ashfield MA 01330

Ashfield, MA719 Barnes Road

Price$750,000

Est. Mortgage: $/month

MLS Number 72771279

  • Single Family Detached
  • Bathroom 4
  • Rooms 10
  • Bedrooms 4
  • Square Feet 4,059

LEED Platinum Certified Home on 10 acres with Pond!LEED Platinum Certified home with a wonderful eco-friendly 10+ acre backdrop with large pond! Guilt free living knowing the environment was the main focus when constructing the very first LEED Platinum Certified home in Western Mass. Designed for maximum energy savings, indoor air quality, water conservation and personal comfort, this 4 bed, 3.5 bath home boasts an incredible backdrop with frontage on a picturesque pond and extensive organic gardens to further assist in the efforts of sustainability in a country setting. Located approximately 500 feet from your neighboring golf course or a short drive to the Berkshires and Northampton, there are local amenities or nearby sought after major attractions. A truly unique and one of kind property for your new reprieve from the city life.

Listed by Jeffrey Loholdt of William Pitt Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.79% last updated on Jan 14, 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

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.