Welcome To The Berkshires

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

Single Family Homes

5 Aspen Way Pittsfield MA 01201

Pittsfield, MA5 Aspen Way

Price$799,000

Est. Mortgage: $/month

MLS Number 245340

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,000

Great opportunity to custom design your 2000 square foot free-standing condo home at berkshire country meadows! This is one of only a few remaining sites in this established community. Close to pontoosuc lake and centrally located for all berkshire attractions. Association has a club house with fitness equipment, pool and tennis. Select from several floor plans which feature a contemporary design, one-level open living plan with primary suite, two additional bedrooms, gas fireplace, attached two-car garage. Natural gas heat, central a/c, screened porch.

Listed by Pamela Roberts of ROBERTS & ASSOC. REALTY,INC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.83% last updated on Apr 17, 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

15 Cherry Hill Drive Pittsfield MA 01201

Pittsfield, MA15 Cherry Hill Drive

Price$799,000

Est. Mortgage: $/month

MLS Number 245353

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,000

Looking to have your new home in the new year? This berkshire country meadows single-level living condo will be ready for summer 2025 occupancy! Construction is well underway for this 2000sf, 3 bedroom, 2 bath stand-alone condo, but there is still time to make your own personalized selections! Central a/c, natural gas heat, gas fireplace, hardwood floors, two car garage. The condo community features pool, tennis, a clubhouse with fitness room. Around the corner from pontoosuc lake, close to skiing, and all berkshire cultural attractions!

Listed by Pamela Roberts of ROBERTS & ASSOC. REALTY,INC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.83% last updated on Apr 17, 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

86 Main Street Sheffield MA 01257

Sheffield, MA86 Main Street

Price$798,000

Est. Mortgage: $/month

MLS Number 245626

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 3,082
  • Acreage 0.5

This gracious vintage home has been thoughtfully renovated and lovingly maintained by the current owners for over 20 years. High ceilings, wonderful light, spacious rooms, a ''walk to everything'' in town location, and residential/commercial zoning provide comfort and unlimited possibilities. A 1,000 sq. Ft. Outbuilding with water & electric service adds more potential. Beautiful period detail combines with with modern updates-crown molding, soapstone counters, farmer's sink, cherry cabinets, a built in hutch, wood & tile flooring, a south facing bay window, french doors, a large 1st floor laundry room, new water heater, and new septic are just the beginning. The large, private room above the garage is an ideal studio or office. There is so much to enjoy here-come see for yourself!

Listed by David W Taylor and Elyse Harney Morris of ELYSE HARNEY REAL ESTATE

$
$
%
$/month over payments
Federal 30-year interest rate: 6.83% last updated on Apr 17, 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

371 Berkshire School Road Sheffield MA 01257
Pending

MLS Number 245824

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,633
  • Acreage 3

Step into a world of elegance and comfort with this gracious home, bathed in natural light and designed for sophisticated living. Set on a sprawling three-acre lot, this property features well-designed rooms that create an inviting atmosphere for both relaxation and entertainment. At the heart of the home, the updated kitchen serves as a culinary haven. The first-floor primary en-suite bedroom offers a private retreat. With three bedrooms and two full and one half baths, there is ample space for family and guests alike. The family room, with its radiant floor heating, ensures cozy comfort, while two wood-burning fireplaces add a touch of traditional charm. Step outside onto the decks and immerse yourself in the tranquility of your surroundings, where the beauty of nature is your backdrop.

Listed by Leslie G Chesloff of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 6.83% last updated on Apr 17, 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

367 North Plain Road Great Barrington MA 01236

MLS Number 243852

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,422
  • Acreage 1.48

1880 4 bedroom colonial in a beautiful pastoral setting. Open living and kitchen plan.Permitted wood burning stove in living room. Second floor has 3 bedrooms, one is a generously sized en-suite. Garage was converted partially for a perfect home office or 4th bedroom. Laundry facilities and half bath located on 1st floor. Outdoor space includes a deck, a partially fenced portion of yard for a dog or children, and lots more level ground for a future pool or recreation. Minutes to town of great barrington and all the berkshires have to offer.

Listed by Mark Rosengren of LANCE VERMEULEN RE,INC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.83% last updated on Apr 17, 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

11 Prospect Street Great Barrington MA 01230

MLS Number 245906

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,114
  • Acreage 0.3

Nestled ''on the hill'' in the heart of great barrington, this inviting 4-bedroom, 2.5-bath colonial offers a perfect blend of comfort, style, and location. Just minutes to the tranquil lake mansfield, this home is ideal for those seeking both convenience and serenity.The generous living room is perfect for both family gatherings and quiet evenings, featuring a cozy pellet stove fireplace that creates a welcoming atmosphere.The eat-in kitchen offers ample space for cooking and entertaining, while the adjacent screened-in deck provides an ideal spot to relax and enjoy the outdoors, whether you're hosting friends or savoring a morning coffee. 4 bedrooms, including a primary suite with an ensuite bath. The additional bedrooms provide flexibility for family, guests, or a home office.

Listed by Jessie Bennett of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 6.83% last updated on Apr 17, 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

37 Egremont Plain Road Great Barrington MA 01230
Pending

MLS Number 244369

  • Residential
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 3,284
  • Acreage 1

This 1700s dutch farmhouse is filled with history and was originally utilized for farming and wagon manufacturing. The residence boasts spacious, well-lit rooms with stunning wide plank wood flooring, offering a grand setting for gatherings and entertainment. The sizable kitchen and dining area, along with four bedrooms and two fully renovated bathrooms, provide ample living space. A highlight of the property is the beautiful sunroom that overlooks the backyard, complete with a heated gunite pool. Additional features include a workshop, seasonal living room, bonus room and studio within the carriage barn, offering potential for further customizable living spaces.

Listed by Paige Lang Paluch of LANCE VERMEULEN RE,INC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.83% last updated on Apr 17, 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

10 Lillybrook Road Pittsfield MA 01201

Pittsfield, MA10 Lillybrook Road

Price$759,000

Est. Mortgage: $/month

MLS Number 244543

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 2,748
  • Acreage 1.27

Beautiful 4 bedroom contemporary on lilybrook road. Vaulted entry way leads to living (sitting) room flanked by formal dining room. Also on the first floor is oversized great (family) room with fireplace, large eat-in kitchen and private master (in-law) suite with full bath and jet tub. The second floor has another master suite with full private bath, two additional bedrooms, and a second full bath. This is perfect for a multi generational family. The basement has plenty of storage and a dry, carpeted rec room with a wet bar and a half bath. The grounds feature mature landscaping and privacy. The roof, skylights, and gas fireplace are newer (installed in 2016). Home is on a private street with a cul-de-sac and is within walking distance to bcc and the state forest. Bosquet and jiminy peak

Listed by Paul R Clark of CLARK REALTY GROUP LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.83% last updated on Apr 17, 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

251 Norfolk Road New Marlborough MA 01259

New Marlborough, MA251 Norfolk Road

Price$728,000

Est. Mortgage: $/month

MLS Number 244871

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 1,927
  • Acreage 3.56

Moments to morning coffee at the iconic southfield store, you'll find your private, yet accessible contemporary home completed in 2005.Set back from the road, the home offers a fantastic and sensible layout including a primary suite on the first floor as well as two bedrooms and shared bath. The spacious living, dining, kitchen (with fireplace and gathering space) all open to the west-facing mahogany deck. Enjoy stunning westerly views abound and lead your eye all the way to new york state and past the lower taconic range. Sunsets!The lower / basement level including french doors and windows opening onto the garden, awaits your finishing touches. Plumbed for a bathroom, there are a number of possibilities and an additional 1927sf not represented in the finished square ftge.

Listed by Freddy Friedman and Selina Lamb of BIRCH PROPERTIES

$
$
%
$/month over payments
Federal 30-year interest rate: 6.83% last updated on Apr 17, 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

3 Lake Buel Road Great Barrington MA 01230

MLS Number 243061

  • Residential
  • Bathroom 7
  • Bedrooms 7
  • Square Feet 3,684
  • Acreage 1

Discover the timeless allure of 'the turning point,' a quintessential berkshire retreat nestled in the hills of great barrington. Originally a 1800's stagecoach stop, this enchanting 3600-square-foot property boasts a rich history as a thriving inn, short-term rental and home, offering 7 bedrooms and 6.5 bathrooms. Immerse yourself in its new england charm, complete with a wood stove, propane fireplace, wide plank floors, large kitchen, first floor bedroom, office and a welcoming floorplan emanating warmth and comfort. Perfectly situated mere moments from butternut basin (one of the berkshires top ski destinations) and a short drive from vibrant downtown great barrington, this charming sanctuary invites you to experience the best of berkshire living.

Listed by Antonio M Segalla of LANCE VERMEULEN RE,INC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.83% last updated on Apr 17, 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

64 Hewins Street Sheffield MA 01257

Sheffield, MA64 Hewins Street

Price$725,000

Est. Mortgage: $/month

MLS Number 244746

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,455
  • Acreage 1.56

A rare & authentic 1842 post & beam farmhouse w/ many original details. This one-of-a-kind antique home awaits the reinvention & stewardship of it's next owners. In the same family for the last 125 years, and with just two prior owners since being built, the structure features post & beam construction, two original fireplaces, antique hardware, woodwork and doors that exemplify early american craftsmanship. The home offers a spacious first floor with two kitchens (once used as a two-family), dining room & parlor, and 2nd floor offers 4 bedrooms and two baths. The 1.5 acre parcel offers extraordinary western sunset views towards mt. Everett overlooking the housatonic river valley. A once-in-a-lifetime opportunity to own and restore an iconic home.

Listed by Dan Alden of ALDEN COUNTRY REAL ESTATE SERVICES

$
$
%
$/month over payments
Federal 30-year interest rate: 6.83% last updated on Apr 17, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

41 Meadow Ridge Drive Pittsfield MA 01201

Pittsfield, MA41 Meadow Ridge Drive

Price$725,000

Est. Mortgage: $/month

MLS Number 245273

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,451
  • Acreage 0.53

Gorgeous. Stately home features 4 bedrooms, 2.5 baths, cathedral center foyer entry. Open floor plan kitchen with granite counter tops, tons of cabinets, adjoining breakfast nook and fireplaced living room. French doors open to large all season sunroom. Natural light filled office/den, wainscoted dining room and tiled laundry room complete the first floor. Lustrous wood floors throughout main floor. Primary bedroom ensuite includes tiled bath, jetted tub, walk in closet. 3 more bedrooms, and 2nd full bath complete the freshly carpeted second floor. Finished basement includes a projector/screen movie area along with plenty of room for a gym, pool and/or ping pong table. French door walkout opens to a paved patio for grilling or access to your private yard.

Listed by Margaret Apkin of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 6.83% last updated on Apr 17, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Recommended Searches