Berkshire County Homes with Privacy

View all Berkshire County homes for sale with privacy below.

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. 

You might also like to register with our site for free to save your favorite listings and receive emails when a new property matches your specified criteria.  

250 Long Pond Rd Great Barrington MA 01230

Price$8,750,000

Est. Mortgage: $/month

MLS Number 225029

  • Listings Residential
  • Address 250 Long Pond Rd
  • Village Housatonic
  • Bedrooms 9
  • Bathroom 10

Contemporary masterpiece beautifully situated on 120 acres offers privacy and breathtaking views in every season. Main House and Guest House were designed by Steven Haas, recognized by Architectural Digest as one of the world's foremost architects. Sorpetaler sliding glass walls and expansive decks create a harmonious interplay with nature. Beautiful barn adds to allure of this unique property. Outdoor features include 25-meter heated saltwater lap pool, hot tub, outdoor showers, stone fire pit, exquisite rock outcroppings, sweeping lawn, hiking trails and access to Williams River trout stream. Quintessential Berkshires setting off private road just minutes from vibrant town center of Great Barrington, selected in 2012 by Smithsonian Magazine as #1 of The 20 best small towns in America.

Listed by Reciprocal Listing: See Realtor Remarks of NON-MEMBER

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

119 Center Rd West Stockbridge MA 01266

Price$6,950,000

Est. Mortgage: $/month

MLS Number 223235

  • Listings Residential
  • Address 119 Center Rd
  • Bedrooms 6
  • Bathroom 8
  • Square Feet 6700

When New England Hall of Fame Interior Designer Dalia Tamari decided to devote 3 years to designing and building this 6,700+/- sq.ft. European influenced country home, her first step was to select the best of settings in the heart of the Berkshires, MA. The chosen 68+/- acres, accessed by a long and winding drive leads to a hilltop with commanding views and privacy. Exceptionally designed, the home is both grand and family friendly. The kitchen, by the famed designer herself, is a prime gathering area to cook together, set against an elevated field stone fireplace. This magnificent property offers a 1st floor master and 5 add't bedrooms upstairs, all with baths ensuite. The pool is adjacent to a pool house with full scale kitchen and laundry. All set on beautifully landscaped grounds.

Listed by Cindy Welch of LANDVEST, INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

115 Purple Mountain Pass Rd Williamstown MA 01267

MLS Number 224798

  • Listings Residential
  • Bedrooms 5
  • Bathroom 8
  • Square Feet 9582
  • Year Built 2003

''Jackson Hole in the Berkshires'' has a commanding mountain presence on 72+/- lush acres with views to Vermont, Williamstown proper and Mt. Greylock. To add to the ultimate privacy, the property is surrounded by the 2600+/- acre Hopkins Memorial Forest owned by Williams College. While offering the utmost in privacy and tranquility, the house is minutes down the hill to the burgeoning North County cultural and recreational amenities fueled by MassMOCA, Williams College, Williamstown Theatre Festival, the Clark Art Museum and Jinny Peak. Designed by a famed Jackson Hole architect and constructed with beams hand hewn in Montana and shipped to Williamstown, the 10,000+/- ft* residence has two levels, a first floor Master bedroom and 4 other bedrooms, all with baths ensuite.

Listed by Cindy Welch and Keith Ross of LANDVEST, INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

2650 Swamp Rd Richmond MA 01254

Price$2,550,000

Est. Mortgage: $/month

MLS Number 221750

  • Listings Residential
  • Address 2650 Swamp Rd
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 4182

April Hill, a meticulously restored Greek Revival with privacy, guest house, swimming pool and spectacular views. See the supplement for details.

Listed by Scott W. Sawyer of STONE HOUSE PROPERTIES, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

720 West Rd Richmond MA 01254

Price$2,450,000

Est. Mortgage: $/month

MLS Number 220880

  • Listings Residential
  • Address 720 West Rd
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4228

Absolutely one of a kind, Do you remember when you were 10 and would escape to your tree house to enjoy no sound other than the relaxing rustling of leaves in the breeze? You can have that wondrous feeling again with the absolute quiet and privacy of the 5 bedroom, 4 baths, 3 story Treehouse set on 100+/- acres just 3 miles from Tanglewood. Designed by famed architect David Sellers, who was twice named as one of the top 100 architects of the world, and noted for bringing the "outside in"; the Treehouse is fully constructed with trees. The property offers both open and high ceiling common rooms along with cozy spaces. Heavy use of natural materials with tree beams and stone gathered from the site for the main massive fireplace Multiple balconies on all 3 levels with possible 360 degree views

Listed by Cindy Welch and Keith Ross of LANDVEST, INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

60 Old Cheshire Rd Lanesboro MA 01237

Price$2,435,000

Est. Mortgage: $/month

MLS Number 224135

  • Listings Residential
  • Address 60 Old Cheshire Rd
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 6100

Windy Ridge Farm is an elegant country estate on 140 acres with views to Mt Greylock and the valley to the south. The location off a 1/4 mile long tree lined drive offers privacy in a bucolic setting, yet is only a 15 min drive to Williamstown's Clark Art Institute, MASSMoca, 8 minutes to Jiminy Peak Skiing, and 28 minutes to Tanglewood and Lenox. There is so much to enjoy at home! The fabulous gunite pool with water fountain and surround sound, and the tennis court are favorites for the summer. The wine entertaining area is used for pre-dinner cocktails and dining is either seasonally in the 3-season gazebo with 360-degree views or the formal dining room with a roaring fire. The sunken living room with 20' ceiling, fireplace and balcony is ideal for an oversized Christmas tree. Guests are

Listed by Cindy Welch of LANDVEST, INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

35-A Creamery Rd Egremont MA 01258

Price$1,795,000

Est. Mortgage: $/month

MLS Number 218500

  • Listings Residential
  • Address 35-A Creamery Rd
  • Village South Egremont
  • Bedrooms 4
  • Bathroom 5

Architect designed, Frank Lloyd Wright inspired, mountain lodge-style home with park like grounds is situated to capture the changing seasonal light and foliage. This tasteful and stately home, sports a contemporary interior with attention to detail and lends itself to many styles of furniture and artwork. All who visited love it, as you will. See supplement. The house sits one quarter mile off the road for maximum privacy and only three miles from Great Barrington. The driveway approach is easily navigated in summer or winter, and the driveway alarm will alert homeowners when vehicles enter the property. The 16 acres property features walking paths with foot bridges over the owner's pristine stream which bounds the rear of the property. The house sits on a crushed stone platform terrace ideal for the display of outdoor sculptures. The front entry opens to a twenty foot high barrel-vaulted foyer and lengthy gallery. The spacious great room has a sophisticated, playful design accented with brightly colored columns. Black slate inlays in the cherry floor defines different living spaces. Oversized French doors open to the rear crushed stone patio, the masonry wood burning fireplace is currently fitted with gas logs. Cherry paneled wall with shelving is back lit to display collectible objects. The dining room with custom floor to ceiling windows boasts a built in buffet with matching counters and cabinetry. The kitchen has granite counters and uniquely shaped island that comfortably sits six. Nickel tile back splash and contemporary custom cabinetry, and includes Viking appliances, very large walk-in pantry and ample additional storage areas. The laundry room/office is outfitted with cherry cabinetry and desk, and it provides a utility closet bench and shoe storage. The cherry paneled study gives a nod to the classic men's library. The luxurious master suite located on the first level creates a warm space with cherry paneling and broadloom carpeting by Masland. The master bath gleams with statuary white marble, cherry cabinetry and paneling, extra-large frameless glass shower enclosure. The dual sinks in the custom cabinetry provide towel storage and custom medicine chests outfitted with power outlets. The master dressing room is very generous in size. Your guests will take the gently curved stai...

Listed by Mary R White and Barnbrook Realty of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

79 Hawthorne St Stockbridge MA 01262

Price$1,750,000

Est. Mortgage: $/month

MLS Number 225611

  • Listings Residential
  • Address 79 Hawthorne St
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 5952

An exquisite traditional Georgian-style brick manor house is the centerpiece of this rare 36-acre Stockbridge estate, which offers both privacy and proximity to Lenox village, Wheatleigh, Tanglewood, and myriad Berkshire amenities. In a jewel-like setting with mature landscaping and views of lawns and hills, the residence combines 21st-century conveniences with impeccable architectural details, including elements from historic Georgian and Federal homes. Conveying quality and luxury, these details--a welcoming arms staircase, graceful columns and mantels, Palladian windows--epitomize the finest in traditional American design and create an ideal place for entertaining. The photos, virtual tour and floor plans are helpful, but, for the discerning buyer, this property is a must see.

Listed by Gladys Montgomery and Maggie Barry of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

280 Division St Great Barrington MA 01230

Price$1,550,000

Est. Mortgage: $/month

MLS Number 218213

  • Listings Residential
  • Address 280 Division St
  • Bedrooms 7
  • Bathroom 6
  • Square Feet 6080

Affording the perfect combination of privacy and luxury, this fabulous Contemporary is an outstanding choice for the Berkshires. It's stunning interior with 7 bedrooms, 5 baths and powder room, includes a guest wing with separate entrance, UNIQUELY SUITABLE FOR A PROFESSIONAL OFFICE The luxurious master bedroom features his and her bathrooms en suite. Situated on beautiful, professionally landscaped five plus acres, spacious decking and a dramatic gunite pool, this home is just a few short miles from town and is a convenient location for all the Berkshires offers.

Listed by Steve Erenburg of COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

250 West St Lenox MA 01240

Price$1,550,000

Est. Mortgage: $/month

MLS Number 225054

  • Listings Residential
  • Address 250 West St
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 4307

Gorgeous Newer Contemporary, custom-built with amazing architectural details! This home features a gourmet kitchen equipped with high-end appliances, granite countertops, a spacious two story living room, and an open floor plan. There are Vibrant Cherry floors throughout, an over-sized gas fireplace, exceptional tile and masonry work, and plenty of unique custom features around every corner. The first floor Master Bedroom/Bath allows for easy accessibility, while a Guest-Suite featuring a separate staircase provides your guests with their own private space. Situated on 5.4 acres, you have all the privacy you need, while still being steps from Tanglewood and other downtown Lenox attractions.

Listed by Maxwell Lenihan of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY, LENOX

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

759 Hancock Rd Williamstown MA 01267

Price$1,500,000

Est. Mortgage: $/month

MLS Number 220686

  • Listings Residential
  • Address 759 Hancock Rd
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 6412

An impeccable family compound nestled in the hills of Western Massachusetts. Located in the Berkshires, this Williamstown Country home offers so much for all ages; The massive 100 acres of open meadow and magical wooded forest as your backdrop affords tremendous privacy, yet activities for each wonderful season from fishing or swimming in your fresh water ponds to hiking and biking miles of...

Listed by Jeffrey M. Loholdt of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

5 Stone Hill Rd Stockbridge MA 01262

Price$1,490,000

Est. Mortgage: $/month

MLS Number 224975

  • Listings Residential
  • Address 5 Stone Hill Rd
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4247

Stockbridge contemporary with a BIG western view from every room masterfully combining architecture with nature. The moment you enter this ''comfort house'' you are immediately drawn to the panoramic view of the Berkshire Hills. The main level living with an expansive open floor plan, dramatic cathedral ceiling w/exposed beams & fp in Great Room flow beautifully to the dining/kitchen; all w/direct access to the spacious screened porch & stone patio making this a perfect home for entertaining. Separate wing for the MB en suite offers complete privacy from the guest BR's en suite. Site specific architecture of this home has captured the skyline of the Berkshires & offers the owner the opportunity to live in the moment from every vantage point in this special home minutes from Tanglewood!!

Listed by Mary Jane White and Cortney K Dupont of COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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