Berkshire County Homes with Guest Houses

Find all Berkshire County homes for sale with guest houses below.

Western MA Homes with a Guest House 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. 

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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

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Federal 30-year interest rate: 4.06% last updated on May 23, 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.

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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

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$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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.

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12 Red Rock Rd West Stockbridge MA 01266

Price$2,500,000

Est. Mortgage: $/month

MLS Number 225154

  • Listings Residential
  • Address 12 Red Rock Rd
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4258

Apple Tree Farm -A custom designed contemporary home in West Stockbridge, Massachusetts recalls the halcyon days of the mid-1980s. A magical private setting with views, clay bottom swimming pond, over sized hot tub, incredible gardens and grounds....The stone walls , walk ways, expansive decks, pergola, Koi pond, screen porch and Birch tree forest are some of the amenities. Main house includes a spacious floor plan with large living room with stone fireplace, dining room with fireplace, open kitchen, library, two main floor bedrooms and baths. The second floor is comprised of the master suite, with window walls and roof deck to enjoy the mountain views. The free standing 2 bedroom guest house is just steps away. Use as a a studio, his and her offices, gardening room or cozy guest quarter

Listed by Patrice C. Melluzzo and Maggie C Merelle of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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.

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222 Ide Rd Williamstown MA 01267

Price$2,250,000

Est. Mortgage: $/month

MLS Number 227158

  • Listings Residential
  • Address 222 Ide Rd
  • Bedrooms 8
  • Bathroom 8
  • Square Feet 7215

A stunning renovation and restoration has elevated this historic Arts & Crafts home to a new level, where elegance and simplicity reign. Sited on 2.78 acres, this magnificent country compound is an alchemy of superb design and the finest quality materials and workmanship. Ideally suited to large-scale entertaining, it totals 7,215sf of living space in the main house, guest house, and suite over the garage, and offers seven to eight bedrooms, seven and one-half baths, a gourmet kitchen, spacious light-filled rooms for large parties, intimate fireplace rooms for quiet conversation, a colonnaded terrace with a glorious mountain view, and a generous three-season room that overlooks a lovely landscaped patio, and heated in-ground pool. Beyond the pool and patio, bluestone walls and walkways

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

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$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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.

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236 Bulkley St Williamstown MA 01267

Price$1,500,000

Est. Mortgage: $/month

Pending

MLS Number 223648

  • Listings Residential
  • Address 236 Bulkley St
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 4990

Designed by legendary Bauhaus architect Marcel Breuer, this Mid-Century Modern masterpiece is a rare, iconic work of art. Exemplifying the luxury of great modern design are Breuer's bi-nuclear floor plan, sculptural butterfly roof, brilliant use of stone, glass, wood & steel, and superb indoor-outdoor flow. Interacting beautifully with its surroundings, ''The Robinson House'' is privately set as the focal point of a 42.5 acre estate with a swimming pool, 900sf guest house with bedroom, kitchenette & sleeping loft, Hoosac River frontage, and private access to Hopkins Forest conservation land. It is convenient to Williams College, Clark Art, Williamstown Theatre Festival, restaurants & shops, and the many cultural & recreational amenities in the Berkshires & Southern Vermont.

Listed by Gladys Montgomery and Leslie G Chesloff of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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.

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35 & 35A Baldwin Hill East West -- Egremont MA 01230

MLS Number 223725

  • Listings Residential
  • Bedrooms 5
  • Bathroom 9
  • Square Feet 4213
  • Year Built 1890

Extraordinary country compound comprising two homes and barns on 15 acres with gorgeous rural and mountain views. The 5BR main house is a magnificent Queen Anne Victorian, with three floors of living space, an elevator, a renovated kitchen with high-end appliances, beautiful architectural details, sleeping porch, and wonderful views from every window. The 4BR/2128sf guest house is a Federal period post-and-beam. Both homes have been maintained lovingly and well. A fabulous barn (two, actually), a lovely in-ground pool, flagstone terrace, pergola, and sweet children's playhouse complete this truly idyllic place. In a prime location, minutes from Main Street, Great Barrington, convenient to the Taconic Parkway, etc.

Listed by Gladys Montgomery and Leslie G Chesloff of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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.

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2 Fox Hollow Rd Lenox MA 01240

Price$1,400,000

Est. Mortgage: $/month

MLS Number 224833

  • Listings Residential
  • Address 2 Fox Hollow Rd
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 5500

Grand home and attached guest house with separate entrance, set on a private 2.49 acres, in the Fox Hollow community, with access to Laurel Lake, tennis courts, and indoor and outdoor pools. The gracious main house features three fireplaces, a first-floor master suite, custom gourmet kitchen, year-round sunroom, and formal living and dining rooms; on the second floor are two additional bedrooms, each with its own bath. A short distance away across the deck, the spacious one-level guest house offers a wonderful great room with fireplace, two bedrooms and 1.5 baths. Enjoy ample space for entertaining or live in one and rent the other!

Listed by Leslie G Chesloff and Maggie Barry of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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.

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20 Glendale Rd West Stockbridge MA 01266

Price$995,000

Est. Mortgage: $/month

MLS Number 222773

  • Listings Residential
  • Address 20 Glendale Rd
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 3028

If a PANORAMIC VIEW with privacy is what you are looking for this sophisticated Adirondack Lodge, on a back country road, minutes from everywhere you want to be in the Berkshires is the house for you. Rustic, contemporary open plan living with two-story stone fireplace, screened porch, extensive decking, lots of glass for natural light & views, two-car garage, permitted for a guest house (total of 5 bedrooms for main residence & guest house), 12 + acres of privacy and a MOST spectacular sweeping view.......paradise in the Berkshires!

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

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$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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.

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950 East St Lenox MA 01240

Price$769,000

Est. Mortgage: $/month

MLS Number 220669

  • Listings Residential
  • Address 950 East St
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4066

Priced to sell WAY below assessment, this property offers SO much: beautifully renovated 5BR Farmhouse on almost 20A, fabulous newer building with indoor/outdoor heated pool with sauna, mini kitchen, full bath, dressing room (the roof retracts!!), 2 beautiful and fully renovated guest houses and a huge horse barn....add to that October Mt. Views! This would be a great family compound or convert back to a B&B or Inn for horse lovers! Whatever your use, this is an incredible price for all that it offers!

Listed by Mary Jo Piretti Miller of PIRETTI REAL ESTATE

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$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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.

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250 Maple Ave Great Barrington MA 01230

Price$750,000

Est. Mortgage: $/month

MLS Number 224617

  • Listings Residential
  • Address 250 Maple Ave
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 3648

Please note: This handsome home suffered extensive water damage from burst pipes during winter 2018-19. MOST PHOTOS ARE FROM BEFORE DAMAGE. This unique compound consists of an historic main house dating from 1742, beautiful gunite pool, 2-BR / 1-BA guest house, large carriage house plus additional semi-finished garage. Porches and patios overlook 3 acres of picturesque grounds with expansive lawns, mature trees and pretty plantings. Damaged areas have been professionally gutted. Some beautiful fir floors and antique details remain. Kitchen w/ butler's pantry, grand formal dining room with impressive antique fireplace, window seats, sitting area & door to stone terrace, and den with period fireplace all need to be restored. Living room with period fireplace remains intact.

Listed by Lance Vermeulen and Barney Stein of LANCE VERMEULEN RE, INC

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$
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$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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.

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204+188 Lavino Rd Pownal VT 05261

Price$350,000

Est. Mortgage: $/month

MLS Number 218917

  • Listings Residential
  • Address 204+188 Lavino Rd
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3148

Own your own 100 acre wood-- in Vermont--with beautiful western views, meadows, woods and stream. Privacy and Serenity abound on this magical property located close to both Bennington and Williamstown. Awaiting renovation the spacious 1910 farmhouse offers 5 bedrooms and 3.5 baths, living room, family room, kitchen, porch and patio. A loving hand will return this farmhouse to a remarkable country home and private getaway with its own little guest house. Follow your dream, plant an orchard, grow your own vegetables, ride your horse, take a walk, smell the flowers, sit on a hammock and read-the possibilities are endless! 95.6 acres with frontage on both Ladd and Brookman roads.

Listed by Ann Greenwood of ALTON & WESTALL REAL ESTATE AGENCY, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.06% last updated on May 23, 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.

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