Berkshire County Homes with Guest Houses

MA Homes For Sale with a Guest HouseFind all Berkshire County homes for sale with guest houses below. Learn about life in the Berkshires!

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 Great Barrington MA 01230

Great Barrington, MA250 Long Pond Rd

Price$6,999,900

Est. Mortgage: $/month

MLS Number 229561

  • Residential
  • Village Housatonic
  • Bathroom 10
  • Bedrooms 9
  • Square Feet 14,700

Contemporary masterpiece beautifully situated on 120 acres offers privacy, tranquility, and breathtaking views in every season. The main house and the 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 3,000 square foot barn with soaring ceilings adds to the 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, running and biking trails, and access to williams river trout stream. Quintessential berkshires setting off a private country road just ten minutes from the vibrant town center

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

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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* 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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359 N Plain Great Barrington MA 01236

Great Barrington, MA359 N Plain Rd

Price$2,395,000

Est. Mortgage: $/month

MLS Number 230396

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 4,560
  • Year Built 2001

Arts and crafts style: take in the unparalleled beauty and majestic views of this 24-acre riverfront property. This 5-bedroom well-appointed home and private guest house create the perfect retreat. With airy open-plan living, main house offers 4,500+ sq. Ft., 3 fireplaces, panoramic views and a private 1st floor master wing. Entertain family and friends throughout the 1st floor or unwind in the spacious informal living room on the 2nd floor. Explore the property on well- maintained walking trails or cool off in the tranquil williams river, the perfect spot to fish, kayak or swim. Outdoor living spaces abound, including a large screened porch with fireplace and adjacent stone patio, ideal for watching a beautiful berkshire sunset. Minutes to great barrington and tanglewood.

Listed by Suzann Laverack Ward and Maureen White Kirkby of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* 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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1488 State Richmond MA 01254

Richmond, MA1488 State Rd

Price$1,500,000

Est. Mortgage: $/month

MLS Number 227718

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 4,098
  • Year Built 1995

A picture perfect home in a stunning location. Minutes from the iconic shaker village museum, tanglewood and multiple cultural activities. This incredible custom built home with quarried front home sits on 15 graceful acres. The main house has a floor plan for easy living and ample space for entertaining family and friends. Steps away from the main house is a studio that could easily be used as a guest house. Your horses will enjoy the land, open and wooded and the 3 stall barn/gardening sheds. Enjoy, gardens, stone walls, views, porch or patio, quality construction and finish.....Imagine the perfect get away either weekend or year round.....A feeling of serenity and peacefulness throughout the house, guest house and grounds. Come and enjoy the community of richmond ma

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

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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* 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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282 County Florida MA 01247

Florida, MA282 County Rd

Price$1,400,000

Est. Mortgage: $/month

MLS Number 227891

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 4,076
  • Year Built 2016

This remarkable euro-industrial retreat offers chic, modern country living, with layered spaces, roof decks, top quality construction, and incredible views. Here is sweet seclusion, on 26 acres with a pond, grassy meadow & woods nestled into mohawk state forest, just 12 minutes to massmoca and 25 minutes to williamstown. The main house features a living room, kitchen, scullery & pantry, a library/office, first-floor guest suite, & second-floor master suite, while the guest house comprises a living room, two bedrooms, kitchen & bath. A work barn could be become an artist's studio. With unsurpassed attention to detail, the design, materials, and construction incorporate european woodstoves, imported windows & fittings. An incredibly stylish property for the aesthetically discerning buyer.

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

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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* 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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198 Blythewood Pittsfield MA 01201

Pittsfield, MA198 Blythewood Dr

Price$899,900

Est. Mortgage: $/month

MLS Number 230255

  • Residential
  • Bathroom 1
  • Bedrooms 2
  • Square Feet 975
  • Year Built 1951

Waterfront living with exceptional potential - private cove past apple tree point on lake onota in the berkshires. Lakefront living build on 2 acres or have it as charming as it is 7+ acre lake retreat. This sweet and inviting ranch style home offers full view of the lake and a simple charming feel for yearround living or it can simply be the lake house or guest house as you build your own dream house. Incredible potential with lake frontage & privacy. Bring the family and share the investment. Three parcels: 4. Acres- 2 buildable to the rear - expandable house on .43 lakefront acres , 3 lakefront acres protected to the south totalling - 7.620. Beautifully set in central berkshire for all cultural attractions, close to dining and theatre and own your own eagle nest preserve.

Listed by Tonia L. Scalise of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY, LENOX

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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* 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 Church Great Barrington MA 01230

Great Barrington, MA23 Church St

Price$799,000

Est. Mortgage: $/month

MLS Number 230380

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,767
  • Year Built 1900

Colonial stunner located in the heart of great barrington. Steps from main street shops and restaurants. Complete renovation from top to bottom while keeping original details. Spacious open floor plan from kitchen to living. Refurbished antique floors throughout. Classic sitting room with fireplace. 4 bedrooms with 2.5 bathrooms in this well laid out, sunny & bright home. Expansive screened in porch off the kitchen for outdoor dining. Bonus large barn with electric and bathroom. Convert to a guest house, rental unit or use to park your car. Lots of extra space.

Listed by Elle Villetto of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* 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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42 Golden Hill Lenox MA 01240

Lenox, MA42 Golden Hill Rd

Price$550,000

Est. Mortgage: $/month

Pending

MLS Number 229322

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,778
  • Year Built 1790

Idlyn acres is a charming compound with a stunning 1790 farmhouse, pristine granary building, sweet cottage with foot bridge over steam, oversized 2 car garage with apartment, in-ground swimming pool all on a beautiful cleared 2.25 acres. The 1790 farmhouse has 4 bedrooms & 2 baths, lovely exposed beams & sought after wide plank floors. The 2778 square foot home has been meticulously maintained with beautiful wood shingled roof, new windows & many other upgrades. Earn extra income from the 2 bedroom garage apartment. Restored granary building c. 1736 is in pristine condition and is currently used as a wood shop but could easily be converted into a wonderful extra guest house. Enjoy summers with your family by the in-ground pool or lounging on your front porch.

Listed by Katie Williams and Elle Villetto of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* 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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299-301 State Great Barrington MA 01230

MLS Number 230819

  • Residential
  • Bathroom 3
  • Bedrooms 5
  • Square Feet 3,133
  • Year Built 1900

Opportunity to have your family compound with a pool! This most-convenient location in south berkshire is accessible to all local amenities, skiing, hiking and this property abuts conservancy land. Main house consists of 5 bedrooms, 3 baths along with ample room for family gatherings. The guest house has 2 bedrooms and 1 full bath plus separate lower level for a second living room or media room. Seasonal views to the hillsides of east, beartown, butternut and monument mountains. If no family compound desired, this has supplemental income for the discerning investor. Either way, a value opportunity is here; you decide!

Listed by Thomas K. Doyle, Sr. of LANCE VERMEULEN RE, INC

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$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* 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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115 Maple Great Barrington MA 01230

Great Barrington, MA115 Maple Ave

Price$289,999

Est. Mortgage: $/month

MLS Number 227748

  • Residential
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 1,296
  • Year Built 1949

1950s ranch with many original features in great condition. Features a super geneva kitchen, original electric stove, and white metal cabinets. Dining room and living room have original knotty pine paneling with scalloped trimmed windows. Beautiful fieldstone fireplace in living room, 3 freshly painted bedrooms, and a fully renovated bathroom with floor to ceiling tile. Attached open breezeway and 1-car garage, plus 1,400 square feet in basement for workshop or office. Large back yard with the potential to build a guest house/condo, according to town bylaws and building codes. Newly installed premium timberline shingled roof, and freshly painted exterior over redwood siding. Great value, walk to town!

Listed by Rosemary Ann Baumann of WHEELER & TAYLOR REALTY CO., INC.

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$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* 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 June 7, 2020 . 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.