Berkshire County Homes with Privacy

Homes with Privacy BerkshiresDiscover homes with privacy in Western Massachusetts including Williamstown and surrounding areas. You’ll find a variety of real estate options in the Berkshires, including homes with lots of land and beautiful views in peaceful settings. Some properties are closer to the mountains, others are convenient to town, and you may find those that offer the best of both worlds. Learn about life in the Berkshires!

Tour Western MA Homes with Privacy

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. 

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49 Chanterwood Lee MA 01238

Lee, MA49 Chanterwood Rd

Price$6,700,000

Est. Mortgage: $/month

MLS Number 238793

  • Residential
  • Bathroom 7
  • Bedrooms 5
  • Square Feet 6,000
  • Year Built 2015

Eagles roost: 877 feet of lake frontage and 35 acres on goose pond. Complete privacy.This quintessential berkshire lake lodge, nestled among ancient boulders along the shore of the most pristine lake in the massachusetts berkshire mountains provides unparalleled, gated privacy only moments from all activities the berkshires' has to offer.Designed and constructed for the private use of the builder, no expense has been spared. This five bedroom, 6 1/2 bath, energy efficient home features soaring stone fireplaces, two primary suites on the first level, two guest rooms with en suite baths, an in-law suite and a huge screened porch all with tremendous water views and access to stone patios with fire pits overlooking the lake front.

Listed by Patrice C. Melluzzo and Leslie G Chesloff of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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23 Prospect Hill Stockbridge MA 01262

Stockbridge, MA23 Prospect Hill Rd

Price$5,500,000

Est. Mortgage: $/month

MLS Number 238266

  • Residential
  • Bathroom 7
  • Bedrooms 6
  • Square Feet 8,200
  • Year Built 1968

Privacy and elegant simplicity in a home for all seasonsthis exquisitely designed house, set upon 55+ acres, has sweeping linear forms, large expanses of glass & an open yet cozy floor plan. Dozens of sliding glass doors & windows provide great cooling air flow along with multi-zoned central air if preferred. The extensive indoor use of natural materials like wood, brick & stone tile adds a warmth & beauty to the space & allows it to merge with the surrounding landscape of well-established gardens & woodlands. The layout of the common areas permits an easy & organic flow of movement & while well defined, these areas live in an intentional & casual relationship with each other. This offers a flexible use of space, whether for intimate conversations or large gatherings

Listed by Leslie G Chesloff and Patrice C. Melluzzo of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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55 & 0 Maple Hill West Stockbridge MA 01266

MLS Number 238141

  • Residential
  • Bathroom 9
  • Bedrooms 6
  • Square Feet 9,564
  • Year Built 1988

Dragonfly manor....This stunning berkshire estate on 68+ acres in west stockbridge has recently been renovated and refreshed by custom designing and curated for this special home in a french country with bohemian vintage farmhouse flair for today's lifestyle. Inviting center hall entrance, spacious common rooms, both formal and informal dining, six bedrooms, 7 1/2 baths, study, two sun porches, separate guest apartment, ''pub'' room and library all overlooking stone patios, rolling lawns, a two acre spring fed swimming pond with dock, established landscaping, gardens and specimen orchards, barn with stable & paddock surrounded by privacy and abutting hundreds of acres of protected land in a most convenient location minutes to all things wonderful in the berkshires!

Listed by Mary Jane White and Brandon White of COHEN & WHITE ASSOCIATES

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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10 Dublin Richmond MA 01254

Richmond, MA10 Dublin Rd

Price$3,450,000

Est. Mortgage: $/month

MLS Number 233309

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 5,000
  • Year Built 2002

Beautiful house on a hill. An opportunity to own a unique and special property consisting of 93 acres with thousands of acres of conservation abutting. You can hike to vt. A gated mile long paved drive meanders to the site of this beautiful post and beam home. Privacy abounds and nature is at your doorstep. Open plan with window walls and soaring ceilings overlook the stunning view of richmond pond, meadows, and mountains.. It is the perfect mixture of rustic charm and modern amenities inside and out. The beautiful pool area also has a hot tub for year round enjoyment. There is a three car attached garage plus a two story heated barn. The beautiful land offers the opportunity for an additional home or family compound. Seller may build 5th bedroom for the right offer it is an easy task.

Listed by Maureen White Kirkby of BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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60 Old Cheshire Lanesborough MA 01237

Lanesborough, MA60 Old Cheshire Rd

Price$2,450,000

Est. Mortgage: $/month

MLS Number 237626

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 6,100
  • Year Built 1981

Windy ridge checks all the boxes!* 360 degree views with an unobstructed vista of mt greylock* privacy on 140 open acres, but not secluded; 19 miles to williamstown, 13 miles to lenox, 5 min. To local grocery * heated pool with gorgeous gardens * tennis anyone? Your own court is open* follow the path on the property to cheshire lake for a kayak launch or bike on the berkshire bike trail* generously sized 6100' home with 12 rooms, 4 bedrooms and 5 baths - all in pristine condition* oversized kitchen for all the cooks with high end appliances & walls of windows * working from home? There are two offices* wine room off the dining room w/520 bottle capacity and subzero drawers* 3 car garage* 3 season glass and screen gazebo for sunset views and dinners

Listed by Cindy Welch of LANDVEST,INC.

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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327 Chester Becket MA 01223

Becket, MA327 Chester Rd

Price$2,445,000

Est. Mortgage: $/month

MLS Number 238663

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,200
  • Year Built 1983

Ever dreamed of owning your own nature preserve? Dream no further. Welcome to 220 acres of unspoiled land. This berkshire mountain beauty has a your own private lake with dock, 2 boulder clad rivers with bridge, hiking trails adorned with ferns, 1400 ft granite cliffs while surrounded by state forest on all sides. Absolute privacy. This truly one of a kind property has a phenomenal barn set on an 1800's foundation but resurrected with old reclaimed wood to the ultimate gathering space. Majestic light fixtures fall from the tall ceilings giving the space a definition of evening gaiety. The 3 bedroom cottage stands on the foundation of a windmill that powered the farm in an era gone. In the 60's the owner made great effort in shaping the landscape by adding''fingers'' to the lake, giving

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

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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21 Kalliste Great Barrington MA 01230

Great Barrington, MA21 Kalliste Hill

Price$2,400,000

Est. Mortgage: $/month

MLS Number 234767

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,900
  • Year Built 1981

Privacy, expansiveness & spectacular views into ct! This contemporary cedar home is an idyllic, private sanctuary in a dream location featuring a hilltop swimming pool w/ stone patio, horse barn & room for horses, koi pond w/ bridge, mature landscaping, and beautiful stonework throughout. Perfectly sited on 7.123 acres, this property includes an extra building lot which would allow the construction of another residence making this the complete family compound! The spacious interior of this light-filled home with soothing earth tones & warm woods includes 3 brs, 2.5 bathrooms, open concept floor plan, office space, central a/c, jetted tub, screened porch, fireplace, skylights, and incredible views both inside & out. Gather year-round with friends & family at this spectacular retreat!

Listed by Douglas M Goudey of WHEELER & TAYLOR REALTY CO.,INC.

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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21 Kalliste Great Barrington MA 01230

Great Barrington, MA21 Kalliste Hill

Price$1,900,000

Est. Mortgage: $/month

MLS Number 235495

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,900
  • Year Built 1981

Privacy, expansiveness & spectacular views into ct! This contemporary cedar home is an idyllic, private sanctuary in a dream location featuring a hilltop swimming pool w/ stone patio, horse barn & room for horses, koi pond w/ bridge, mature landscaping, and beautiful stonework throughout. The spacious interior of this light-filled home with soothing earth tones & warm woods includes 3 brs, 2.5 bathrooms, open concept floor plan, office space, central a/c, jetted tub, screened porch, fireplace, skylights, and incredible views both inside & out. Gather year-round with friends & family at this spectacular retreat!

Listed by Douglas M Goudey of WHEELER & TAYLOR REALTY CO.,INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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254 West Lenox MA 01240

Lenox, MA254 West St

Price$1,399,999

Est. Mortgage: $/month

Pending

MLS Number 238304

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,969
  • Year Built 2001

An idlyllic location! This home is directly across from tanglewood yet set back among lush, mature gardens for ultimate privacy. Enjoy this pristine contemporary home with three levels of living. Large chefs kitchen with new appliances. Open concept floor plan. Spacious living room with cozy fireplace. Oversized screened in porch with optional seasonal windows, a delight for 3 seasons. First floor primary with updated shower and walk out to gardens with hot tub. Upstairs has 3 additional roomy and light filled bedrooms with shared bath. Newly renovated lower level family room for the ultimate movie watching or space for your favorite hobby. Solar panels cover the electric for the house. The perfect home minutes to downtown lenox & all your favorite berkshire attractions!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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3 Whiteholme Lee MA 01238

Lee, MA3 Whiteholme Rd

Price$1,225,000

Est. Mortgage: $/month

MLS Number 237589

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,700
  • Year Built 1880

Truly a one-of-a-kind opportunity to be within a block of town yet perched on a hill on your own private 2+ acre parcel! A circular drive leads to a large wrap around porch welcomes one and all and is perfect for summer entertaining. Inside many period details from the 1880 build-date remain but modern conveniences make for easy living. The double doors welcome you into a spacious entry with a curved wall of windows with seating. Hardwood floors in most of the house, front and back staircases, four fireplaces, four plus bedrooms and four full baths. Room to mingle or plenty of privacy with three finished floors of living space. Natural gas heat. Also on the property is a converted carriage barn (please see supplement)

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

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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15 Hickory Hill Egremont MA 01230

Egremont, MA15 Hickory Hill Rd

Price$995,000

Est. Mortgage: $/month

MLS Number 237724

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,793
  • Year Built 1984

As immaculate as the day it was built. Although built in the 80's, this home has a much more cool, retro, mid century 70's vibe. Open plan first floor living spaces with stone fireplace to the ceiling, beautiful gleaming hardwood flooring, open stairway to the second floor balcony and a wall of windows to an unobstructed southwesterly view. The second floor primary bedroom is quite large with a walk in closet more spacious than most. This level also holds a large media/office/guest overflow room. Two first floor guest bedrooms share a full bath and there's an extra half bath, too. The full basement offers terrific workshop and storage space. On a quiet cul de sac road, this home offers peace and privacy, with distant views on a parcel just shy of 3 acres. Attached garage. Fiber internet.

Listed by Fintan T Hanley and Timothy Lovett of BERKSHIRE PROPERTY AGENTS,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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101 Silver Lanesborough MA 01237

Lanesborough, MA101 Silver St

Price$895,000

Est. Mortgage: $/month

MLS Number 237657

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,966
  • Year Built 1984

This property is waiting for you!! It could be your primary home or your vacation home.. A skier's delight as near the jiminy peak resort and many other outdoor activities. Not too far from wiliamstown heading north and not too far from pittsfield with all its cultural activities, heading south. Berkshire medical center in pittsfield is about a 15-20 minute drive..There is a lot of privacy here and a wonderful in ground lap pool that's 50 ft long for exercising or just for fun.. As of 6/22/2022, a new 1500 gallon concrete septic tank was installed along with a new d-box..

Listed by Barbara K. Greenfeld,Broker Associate and Marie E. Bourassa of ROBERTS & ASSOC. REALTY,INC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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 September 30, 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.