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$7,000,000

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: 3.55% last updated on Aug 22, 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: 3.55% last updated on Aug 22, 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: 3.55% last updated on Aug 22, 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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243 & 246 Brookman Dr Otis MA 01253

Price$2,450,000

Est. Mortgage: $/month

MLS Number 227633

  • Listings Residential
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 3688
  • Year Built 2011

Lakefront compound: 243 & 246 Brookman Drive, Otis Reservoir. Stunning, 2011 custom built lakefront home complete with guest house. Multilevel, western facing decks and porches face the lake. Stainless and marble kitchen built for the family chef. Wood burning fieldstone fireplace, screened porch, Trex decking, central AC, whole house standby generator. Three bedrooms w lake views, family room, game room, office, 4 full baths, 2 half baths, kayak & fishing gear room. Two oversized 2 car garages. A dock with 2 boat lifts. Over 3680 square feet in the main house. Directly across the street and included in the sale is 246 Brookman, a 4 bedroom, 2 bath guest house featuring an open floor plan, deck, and attached garage - see MLS 226541 for details.

Listed by Kim Bergland and Ginger Conner of RED HORSE REAL ESTATE

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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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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359 N Plain Rd Great Barrington MA 01230

Price$2,395,000

Est. Mortgage: $/month

MLS Number 228189

  • Listings Residential
  • Address 359 N Plain Rd
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4560

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 luxury retreat. With airy open-plan living, the Craftsman-style 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: 3.55% last updated on Aug 22, 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 of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY, LENOX

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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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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1488 State Rd Richmond MA 01254

Price$1,850,000

Est. Mortgage: $/month

MLS Number 227718

  • Listings Residential
  • Address 1488 State Rd
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4098

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 and Nick Geranios of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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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282 South County Rd Florida MA 01247

Price$1,400,000

Est. Mortgage: $/month

MLS Number 227891

  • Listings Residential
  • Address 282 South County Rd
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 4076

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: 3.55% last updated on Aug 22, 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 Rd Egremont MA 01230

Price$1,400,000

Est. Mortgage: $/month

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 of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$
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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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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198 Blythewood Dr Pittsfield MA 01201

Price$1,250,000

Est. Mortgage: $/month

MLS Number 227348

  • Listings Residential
  • Address 198 Blythewood Dr
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 975

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: 3.55% last updated on Aug 22, 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: 3.55% last updated on Aug 22, 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$650,000

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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$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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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