Berkshire County Cottages

Browse listings for cottages in Berkshire County MA.

MA Cottages for Sale

Contact the Alton & Westall Real Estate Agency online or call 413-458-8366 for more information or to set up a showing for any property below. 

Learn more about life in the Berkshires!

Berkshire County Homes By Architectural Style
Farmhouse | Ranch | Antique | Contemporary | Cape | ColonialCraftsman | Victorian

17 Prospect Hill Stockbridge MA 01262

Stockbridge, MA17 Prospect Hill Rd

Price$4,450,000

Est. Mortgage: $/month

MLS Number 236486

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 6,000
  • Year Built 1900

Enjoy all the berkshire seasons. Winter brings sledding, cross country skiing, access to downhill runs or enjoy the fire pit or get cozy by one of thefour fireplaces. Magnificent unspoiled views to the south and west create interest at all hours of the day and at sunset in particular. Thought to be one the first of the large 'cottages' on prospect hill. A wraparound glass porch overlooks the walled sunken garden. Three floors of living spaces with almost every room open to the views. Beautiful detailing with marble fireplaces and antique woodwork. Four bedroom and four and a half baths. A large game room with full bath occupies the third floor. There is a gunite pool. Golf tee/driving area. Minutes from tanglewood . Additional building lot included.

Listed by Martha Piper of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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

17 Prospect Hill Stockbridge MA 01262

Stockbridge, MA17 Prospect Hill Rd

Price$4,150,000

Est. Mortgage: $/month

MLS Number 234293

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 6,000
  • Year Built 1900

Enjoy all the berkshire seasons. Winter brings sledding, cross country skiing, access to downhill runs or enjoy the fire pit or get cozy by one of thefour fireplaces. Magnificent unspoiled views to the south and west create interest at all hours of the day and at sunset in particular. Thought to be one the first of the large 'cottages' on prospect hill. A wraparound glass porch overlooks the walled sunken garden. Three floors of living spaces with almost every room open to the views. Beautiful detailing with marble fireplaces and antique woodwork. Four bedroom and four and a half baths. A large game room with full bath occupies the third floor. There is a gunite pool. Golf tee/driving area. Minutes from tanglewood . Additional building lot available.

Listed by Martha Piper of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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

135 Main Lenox MA 01240

Lenox, MA135 Main St

Price$2,750,000

Est. Mortgage: $/month

MLS Number 237252

  • Residential
  • Bathroom 17
  • Bedrooms 16
  • Square Feet 8,688
  • Year Built 1780

The garden gables, located in the center of lenox on over 4 very private park-like acres with gardens, patios, mature trees and a heated 70' pool, can be the ultimate family compound. Beautifully furnished and tastefully decorated with 16 unique bedrooms all with updated private baths, several with fireplaces and all fully air conditioned.The historic 1780 main building and attached eladesor cottage includes 12 spacious suites. The separate orchard cottage includes 4 ensuite rooms with separate entrances, cathedral ceilings and fireplaces.There are also 2 charming dining areas in the main building in addition to the library/music room and cozy ''sherry room'' both with fireplaces.The kitchen is equipped with updated appliances. An extraordinary opportunity!

Listed by C. Randolph Thunfors and Michael Linden of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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

108 Interlaken Stockbridge MA 01262

Stockbridge, MA108 Interlaken Rd

Price$2,500,000

Est. Mortgage: $/month

MLS Number 236514

  • Residential
  • Square Feet 500
  • Year Built 1882
  • Acreage 1.34

279' of frontage on stockbridge bowl. A long groomed driveway leads to this large, gorgeous parcel of lakefront. Wide, stunning southeasterly views of the lake with mountains beyond. A boathouse at the waters edge, scarce for lakefront. A victorian cottage (no water or utilities) deemed historic. A rustic storage barn provides a footprint with potential. Septic fields in. Drilled well. Utilities easily accessible. Design plans for a 5,000+ square foot home with garage available. A rare opportunity to own a large parcel of land with frontage on deep lakefront on stockbridge bowl.

Listed by Tom Lynch of BERKSHIRE PROPERTY AGENTS,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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

684 Egremont Great Barrington MA 01230

Great Barrington, MA684 Egremont Rd

Price$1,695,000

Est. Mortgage: $/month

MLS Number 236863

  • Residential
  • Bathroom 20
  • Bedrooms 20
  • Square Feet 17,551
  • Year Built 1850

Unique opportunity for the business-minded interested in purchasing a well-established gem of a bed & breakfast in the heart of the berkshires. Located minutes from cultural attractions w/ convenient access to boston/new york. Windflower inn welcomes guests w/ its wraparound porch & manicured grounds. The inn has 13 bedrooms each w/ their own private bath. Blending the charm of the past w/modern-day conveniences. The commercial grade kitchen & laundry meets the demands of a busy bed & breakfast. The kitchen includes double commercial ovens & has the potential for expansion for restaurant purposes. The 3 bedroom 2.5 bath cottage on site adds income potential. Owners also have a 4 bedroom 2 bath home currently used as innkeepers quarters. Potential for events/weddings/family compound.

Listed by Jessica L. Rizzo of BERKSHIRE DREAM HOME,INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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

75 Chestnut Lee MA 01238

Lee, MA75 Chestnut St

Price$599,000

Est. Mortgage: $/month

MLS Number 236879

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,381
  • Year Built 1886

Chestnut lodge, a charming, rustic historic property, is nestled on over 3 acres with gardens, pasture and abundant stone walls.This post and beam style cape, originally called ''the baker house'' was built circa 1773. Adding to the appeal of this 18th century farmhouse are fieldstone fireplaces, wide plank floors, ,a fascinating tower , a barn with a summer apartment. And a charming cottage the property is located about two miles from main street lee and close to berkshire cultural and recreational activities.

Listed by Anthony Caropreso of MACCARO REAL ESTATE

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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

239 Under Mountain Lenox MA 01240

Lenox, MA239 Under Mountain Rd

Price$595,000

Est. Mortgage: $/month

Pending

MLS Number 236962

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,706
  • Year Built 1880

Location, location, just outside of downtown lenox and a short walk to tanglewood. 1880 cottage on undermountain rd. In lenox, set against a bucolic scene with a natural stream and water feature on two private acres. A lovely area of fine homes and scenic farmlands. A hidden gem in the heart of the berkshires with so much potential, you can feel the warmth the moment you step into this charming lenox cottage. Come and bring your vision to life!

Listed by Susan Calkins of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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 Sheffield Egremont MA 01258

Egremont, MA64 Sheffield Rd

Price$595,000

Est. Mortgage: $/month

MLS Number 237201

  • Residential
  • Village South Egremont
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 3,300

Nature lovers dream! A charming cottage situated on 45+ acres of berkshire woodlands and meadows abutting miles of appalachian trail state land. Hiking trails, water features, and beautiful stands of hardwoods is what this magnificent property has to offer. The cottage offers 3,300 square feet of open living space and a magical fireplace that makes you feel as if you are in a different time. With a little love this property is the perfect berkshire getaway!

Listed by Antonio M Segalla of LANCE VERMEULEN RE,INC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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

91 Henry Hinsdale MA 01235

Hinsdale, MA91 Henry Dr

Price$585,000

Est. Mortgage: $/month

MLS Number 237486

  • Residential
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 1,022
  • Year Built 1946

Enjoy waterfront living year round, as a vacation home, or investment property. 146 feet of pristine lake frontage w/ private dock, kayak/canoe/paddle board storage rack and launch. 2 bedrooms, 1 full bath on first floor and a generous sleeping loft/3rd bedroom w/ skylights and ample storage on second floor. Sweet cottage style kitchen opens to a fabulous great room that combines dining room and family room space and endless lake views. The 3 season porch offers more lake views and leads to the back yard w/ a platform deck for lounging or dining lakeside, plus a fire pit area. This well priced waterfront home in the central berkshires is close to all cultural and recreational activities as well as shopping and dining. Being sold furnished. Won't last long!

Listed by Victoria A Standring of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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

28 Spruce Richmond MA 01254

Richmond, MA28 Spruce Rd

Price$495,500

Est. Mortgage: $/month

MLS Number 236683

  • Residential
  • Bathroom 1
  • Bedrooms 2
  • Square Feet 936
  • Year Built 1970

Relax and and enjoy making lasting memories in this sweet, spacious cottage in a private lake community. A two minute walk to richmond pond beach where you can hang out or launch your kayak on a beautiful clear night and watch the sunset.Nearby places and activities range from a 15-minute drive to live music & performance arts at tanglewood; museums, outdoor activities for all seasons, nearby towns with great restaurants & shopping. See the best of the berkshires: https://travel.Usnews.Com/the_berkshires_ma/things_to_do/the cottage has been renovated and lovingly maintained over the years and sits on a large private lot in a community surrounded by beautiful conversation lands. Some features of the cottage to name just a few: 2019 unico heating and central ac, 2007 metal r

Listed by Susan Calkins of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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

57 Pine Great Barrington MA 01230

Great Barrington, MA57 Pine St

Price$450,000

Est. Mortgage: $/month

MLS Number 237429

  • Residential
  • Bathroom 1
  • Bedrooms 2
  • Square Feet 1,262
  • Year Built 1900

A sweet stroll into the center of great barrington, make this picture perfect renovated cottage on pine street yours! Spacious kitchen with laundry, open dining and living with access to a front sitting porch. Comfy up in the red den room, perfect for reading a book or extra guests. Upstairs has a primary bedroom with cathedral ceiling and office space. Roomy second bedroom and full bath upstairs with shower/tub. House is packed with charm and is move in ready. House can come furnished for extra cost. Check out this little gem and be ready to enjoy the summer in the berkshires!

Listed by Elle Villetto of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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 Beachwood Stockbridge MA 01262

Stockbridge, MA11 Beachwood Dr

Price$389,900

Est. Mortgage: $/month

Pending

MLS Number 237370

  • Residential
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 704
  • Year Built 1920

Welcome to beachwood! This cozy three season cottage is ready for your enjoyment this summer in one of the most sought after communities. Three bedrooms, fireplace, screened porch located on a level corner sun filled lot. Stroll across the street to a path that is seconds away from the spectacular srockbridge bowl private beach with views for days. Short drive to tanglewood and minutes away from downtown stockbridge, lenox and many cultural attractions.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.3% last updated on May 12, 2022
* 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

Based on information submitted to BCMLS  as of May 18, 2022 . All data is obtained from various sources and has not been, and will not be, verified by broker or BCMLS.  All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.