Berkshire County Homes with Guest Houses

MA Homes For Sale with a Guest HouseFind all Berkshire County homes for sale with guest houses below. Browse a variety of listings that provide the privacy you need for your family while being able to spend quality time with your extended family or close friends visit. 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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24 & 30 Berkshire Heights Great Barrington MA 01230

MLS Number 232672

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 6,240
  • Year Built 1918

A rare estate offering in the berkshires. Breathtaking southern and western views from this historically important great barrington estate. Designed by charles platt for charles freer of the renowned freer gallery in dc, and constructed of stone quarried from the property, this one floor layout was well ahead of its time. The main house has a large, comfortable living room with views from massive windows, a library, a gracious dining room, all with fireplaces. The property encompasses a stable and riding ring, pool, orchard, vineyard and two fully equipped guest houses and a caretaker's home. This is a rare opportunity to own a unique nearly 50 acre estate with magnificent views - all close to great barrington.

Listed by Martha Piper of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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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9 Buttondown Great Barrington MA 01236

Great Barrington, MA9 Buttondown Ln

Price$3,200,000

Est. Mortgage: $/month

MLS Number 233388

  • Residential
  • Village Housatonic
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 4,100

Situated at the end of a country road overlooking the williams river is a remarkable modern home on 9 acres.Amenities include: river frontage, pines, river birches, landscaping, stone patios, clay tennis court, heated inground salt water pool andjacuzzi, 4 garages, studio/guest house, wood floors, cathedral ceilings, window walls. The open floor plan includes a kitchen with island, granite or stainless counters, dining space, living room with fireplace, family room all overlook the pool, yard and river. Primary bedroom with extensive views, fireplace, dressing room, incredible bath with soaking tub, walk in shower with glass wall to natural light. Second floor with three bedrooms and two baths. Lower level with room for hobbies/exercise, full bath. Out building with garage, studio, bath

Listed by Patrice C. Melluzzo of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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 West Stockbridge MA 01266

West Stockbridge, MA12 Red Rock Rd

Price$2,450,000

Est. Mortgage: $/month

MLS Number 229485

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 5,824
  • Year Built 1986

Magical, secluded compound set oh-so-privately amongst birch groves down a winding country lane ... Simply stunning views surround this impressive contemporary home, thoughtfully designed to welcome natural light into every restful room. The main residence is graciously open, with many fireplaces & a view in every direction. Clay-bottomed swimming pond, two-bedroom studio/guest house, all on 22+ acres. Tucked away, yet only minutes to the charming and artistic village of west stockbridge. Just a short drive to tanglewood, lenox, and the best of the berkshires!

Listed by Nancy K. Kalodner and Brandon White of COHEN & WHITE ASSOCIATES

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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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 Williamstown MA 01267

Williamstown, MA222 Ide Rd

Price$2,250,000

Est. Mortgage: $/month

MLS Number 231929

  • Residential
  • Bathroom 8
  • Bedrooms 7
  • Square Feet 7,215
  • Year Built 1911

An iconic country estate nestled in the northern hills of berkshire county. Boasting early 1900's classic craftsman style architecture yet fully renovated and modernized with gourmet kitchen and freshly redone, heated gunite in ground pool. The main residence offers a master suite and 3 en suites on the second level while all entertaining spaces are on the ground level with access to patios and porches. Connected by your 3-season glass and screened nature-gallery, your guest house awaits. Multi level with workout space, office and 2 bedrooms / 2 full baths. Further guest accommodations are found above the detached garage blending a more contemporary 1 bedroom with living space and sizable full bath. Its rare to find almost 3 acres in such close proximity to all of williamstown.

Listed by Jeffrey M. Loholdt of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

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$
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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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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0,183 &185 Pine Otis MA 01253

Otis, MA0,183 &185 Pine Rd

Price$1,750,000

Est. Mortgage: $/month

MLS Number 233964

  • Residential
  • Bathroom 3
  • Bedrooms 6
  • Square Feet 3,416
  • Year Built 1111

Welcome to the berkshires & otis reservoir -the largest recreational lake in ma at 1085 acres.This listing is all about the land,the location & 150 ft of beautiful waterfront.The property consists of 3 parcels making up a unique, conforming 1.39 acre compound,with 4 well maintained docks, lakeside patio,2 homes and additional lot.Right on the lake is a 4 bedroom seasonal cottage with an indoor wrap-around porch & water views galore.Build your dream home or use as is for a summer of family fun.The 2nd waterfront has a small, quaint,4 season home.A large front deck offers quieter,private lake views.Great for guests,winter getaways or summer rentals.The 3rd parcel is a .47acre lot with potential use as a garage or guest house site. Please enjoy the aerial photos to get a sense of the property

Listed by Kim Bergland of RED HORSE REAL ESTATE

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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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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117 Cliffwood Lenox MA 01240

Lenox, MA117 Cliffwood St

Price$1,585,000

Est. Mortgage: $/month

Pending

MLS Number 233544

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,992
  • Year Built 1900

Cliffwood street is a favored street offering historic houses & a sidewalk lined walk to town location. The other direction takes you to kennedy park for hiking, biking, and on to the main gates of tanglewood. With the two bedroom guest house the bedroom count of this beautifully renovated property totals six. Also a four car carriage barn/garage. Main house has good flow & the expansive cook's kitchen with an abundance of storage is the focal point. Living area opens to the kitchen, also a den, both w/ fireplaces. The bedrooms are spacious. Third floor suite. 1000 sqft guest house has a full kitchen, central a/c & private entrance. This estate parcel is quietly sited and offers a sweeping front lawn, specimen trees & lush landscaping. Perfect to use year round or summer home property.

Listed by Lori J Rose of STONE HOUSE PROPERTIES, LLC

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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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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45 Walker Lenox MA 01240

Lenox, MA45 Walker St

Price$1,350,000

Est. Mortgage: $/month

MLS Number 234073

  • Residential
  • Bathroom 3
  • Bedrooms 7
  • Square Feet 5,600
  • Year Built 1897

Downtown lenox gilded age former home, currently used as multiple office suites. The 3000sf carriage house behind holds an office suite on the first floor, a three bedroom apartment on the second, and a one-car garage workshop. This beautiful example of colonial revival architecture is one of two ''cottages'' built by the bishop family as guest houses to their mansions, the other is next door. The david wolf bishop house has a wide entry porch flanking the facade and a front circular drive large enough for parking. There is a second and larger private parking lot behind the main house accessed from church street. The main building may easily be transformed back into a single family residence. Due to covid, offices and the apartment will may not be shown on first showings.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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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1411 Main Williamstown MA 01267

Williamstown, MA1411 Main St

Price$1,250,000

Est. Mortgage: $/month

Pending

MLS Number 234717

  • Residential
  • Bathroom 6
  • Bedrooms 6
  • Square Feet 4,051
  • Year Built 1880

Unbelievable amenities on this quiet williamstown estate tucked back in the center of town. This magical estate is close enough for the ability of getting anywhere in town with the privacy of a tranquil setting. Once part of the cole porter estate on almost 3 acres with stunning mature landscaping will delight you with beauty through all four seasons. A special family compound in the heart of northern berkshire county. Williamstown's finest, close to downtown, williams college and the francine & clark art museum. This spectacular property consists of 4 buildings, a newly renovated heated oversized in ground pool, a newly renovated pool house, with fireplace, kitchen and 3/4 bathroom, a guest house, tennis court, a 6 bay garage and a 3 bedroom apartment. The 3 acres are landscaped and

Listed by Kim Murphy Burnham of BURNHAM GOLD REAL ESTATE, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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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310 Monument Valley Great Barrington MA 01230

MLS Number 234825

  • Residential
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 3,233
  • Year Built 1983

Bright & spacious 2,433 sf contemporary & 800 sf cottage set amongst beautiful flowering trees, exquisite perennial gardens & manicured yard overlooking heated in-ground pool and distant southern views. The yard is completely fenced in, perfect for your furry friend. Open floor plan with high ceilings makes for a perfect place to entertain friends and family. In the large kitchen, enjoy the ample space for cooking at the oversized island & light a fire in the large fireplace during those long berkshire winter evenings. The wood floors lead you to a wing of bedrooms featuring a spacious first-floor primary with doors leading to the backyard oasis with nice views. The guest house is the perfect place for extra guests, with a working fireplace, wood floors & kitchenette.

Listed by Antonio M Segalla and Lance Vermeulen of LANCE VERMEULEN RE, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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 Old Stockbridge Lenox MA 01240

Lenox, MA55 Old Stockbridge Rd

Price$925,000

Est. Mortgage: $/month

MLS Number 234026

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,235
  • Year Built 1985

Just a short stroll from the center of lenox you will come to this private, quiet, enchanting retreat on over an acre of bucolic, landscaped land. An existing sweet ranch home can be expanded or used as a guest house for a family/friend compound. The southeast boundary is a brook and most of the surrounding property is protected land. The oversized garage/outbuilding can be utilized as a home office or studio. Let your imagination be your guide for this unique setting.

Listed by Allen Bassen of BERKSHIRE HOMES AND CONDOS

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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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Based on information submitted to BCMLS  as of July 23, 2021 . 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.