5-Bedroom Homes for Sale in Berkshire County MA

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  /43

  $799,000

  • 7 Beds
  • 7 Baths
  • 4,290 Sq Ft

  17 - 23 Linden St, Pittsfield, MA

  Incredible Multi-Unit Investment Opportunity in Downtown Pittsfield!Located just steps from the Barrington Stage Company theater in the heart of the cultural district, this dynamic property includes two fully occupied buildings plus a 4-bay garage, making it a true income-generating powerhouse. With a solid 11.2 cap rate, this is a rare opportunity for both the savvy investor and the live-in

  Michael Castellano Gilcrest Properties

  17 - 23 Linden St, Pittsfield, MA
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  /39

  $565,900

  • 8 Beds
  • 3 Baths
  • 4,034 Sq Ft

  144 Bromback St, Pittsfield, MA 01201

  Beautiful, spacious 8 bedroom, 3 updated bath, 4000 sq ft home, custom built and nestled between 2 lakes with incredible views in the heart of the picturesque Berkshire Mountains! Walk to Onota lake in approximately 10 minutes and enjoy a 5 minute drive to Pontoosuc Lake both suitable for kayaking, swimming, picnicking and more. Enjoy the convenience of two laundry rooms and two updated

  Janet Benoit Janet L. Benoit

  144 Bromback St, Pittsfield, MA 01201
• 

  

  

  /19

  $775,000

  • 8 Beds
  • 4 Baths
  • 3,192 Sq Ft

  35 Main St, West Stockbridge, MA 01266

  Introducing a beautiful in-town 4-family investment opportunity on the picturesque Main St, offering separate utilities for each unit. With a new roof, fresh paint, and renovations completed in units, 1,2 &3 all in 2023.

  Matt Carlino MACCARO REAL ESTATE

  35 Main St, West Stockbridge, MA 01266
• 

  

  

  /19

  $949,000

  • 11 Beds
  • 6 Baths
  • 4,863 Sq Ft

  Unlisted Address

  Fully Rented In Town 5-Family Investment Opportunity. Home office available with a bathroom. Short walk to Post Office, Restaurants, Library and the Red Lion Inn. Stockbridge Town Park located across the street and hiking trails at the end of the street. See pictures.

  Matt Carlino MACCARO REAL ESTATE

  Unlisted Address
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  /48

  $5,475,000

  • 5 Beds
  • 8 Baths
  • 9,400 Sq Ft

  Unlisted Address

  Nestled in the heart of Alford, Massachusetts, this extraordinary 35.6-acre Berkshire County estate offers unparalleled privacy with sweeping western Catskill Mountain views and direct access to conservation land. The impressive 9,400 sq ft main residence, built in 2003 and comprehensively updated beginning in 2020, features 4 bedrooms, 5 full baths, and resort-caliber amenities throughout its

  Elyse Morris ELYSE HARNEY REAL ESTATE

  Unlisted Address
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  /36

  $850,000

  • 10 Beds
  • 4 Baths
  • 5,293 Sq Ft

  458 Monterey Rd, Great Barrington, MA 01230

  This rare find, located on the Great Barrington/Monterey line, offers the right buyer a unique opportunity to live, work, and play in the heart of the Berkshires. Situated on 4.32 acres, this 1958 ranch-style home has evolved over the years into a sprawling 5,200 square-foot property boasting endless potential. While it currently serves as an owner-operated wellness facility, an expansive

  Cortney Dupont COHEN & WHITE ASSOCIATES

  458 Monterey Rd, Great Barrington, MA 01230
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  /46

  $649,900

  • 9 Beds
  • 4 Baths
  • 4,152 Sq Ft

  1057 Main St, Great Barrington, MA 01236

  Great investment opportunity! A very rare property offered for the first time outside the family in over 90 years! This is a well maintained and loved four unit income property that can produce over seventy five thousand dollars per year in rents! Lifetime metal roof, freshly painted exterior and updated units are just a few of the benefits of this investment. In the bustling village of

  Ryan Lane GILCREST PROPERTIES

  1057 Main St, Great Barrington, MA 01236
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  /55

  $5,499,500

  • 8 Beds
  • 6.5 Baths
  • 6,986 Sq Ft

  140 Hancock Rd, Pittsfield, MA 01201

  Welcome to an extraordinary opportunity on the shores of Pontoosuc Lake. This remarkable estate sets a new standard for lakefront living in Pittsfield and beyond, offering a rare combination of luxury, scale, and setting.With over 18,700 square feet of total space, including an impressive amount of garage space suitable for car collectors or hobbyists, this home provides room to live, relax, and

  Cameron Volastro STONE HOUSE PROPERTIES, LLC

  140 Hancock Rd, Pittsfield, MA 01201
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  /39

  $525,000

  • 10 Beds
  • 6 Baths
  • 3,644 Sq Ft

  70-72 Chase Ave, North Adams, MA 01247

  Investor Alert! Fully renovated 4-family in downtown North Adams--turnkey and cash-flowing! With 3,644 sq ft, two 1-2BR units, two 3-4BR units, private porches, and shared yard, this property is a rental powerhouse. Walk to Mass MoCA and downtown! PLUS: Condo docs for this property with--future condo conversion potential for massive upside! Prime location, strong rental history, serious cash

  Christine Girard STEEPLEVIEW REALTY - N. ADAMS

  70-72 Chase Ave, North Adams, MA 01247
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  /17

  $289,900

  • 7 Beds
  • 3 Baths
  • 2,302 Sq Ft

  57 Beacon St, North Adams, MA 01247

  Please allow 48 hour notice for showings

  Michele Purcell Lamacchia Realty, Inc.

  57 Beacon St, North Adams, MA 01247
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  /52

  $730,000

  • 5 Beds
  • 4.5 Baths
  • 3,381 Sq Ft

  33 Alpine Trail, Pittsfield, MA 01201

  Beautiful townhouse located in the Pines at Bousquet with picturesque mountain views! The main level boasts vaulted ceilings with open bright common areas, great room with wood flooring and gas fireplace, updated kitchen, dining room with views, primary bedroom with newly renovated en suite bath, oversized garage, half bathroom and private screened porch and deck to take in the fresh air and

  Cortney Dupont COHEN & WHITE ASSOCIATES

  33 Alpine Trail, Pittsfield, MA 01201
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  /53

  $849,000

  • 8 Beds
  • 4 Baths
  • 3,044 Sq Ft

  328 Park St, Great Barrington, MA 01230

  Two beautifully renovated duplexes within walking distance to the charming village of Housatonic. Enjoy scenic views of the Housatonic River from each unit. All utilities are separate, making this an ideal investment. All units are fully rented.

  Michael Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  328 Park St, Great Barrington, MA 01230
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  /40

  $1,140,000

  • 5 Beds
  • 4.5 Baths
  • 3,100 Sq Ft

  60 Parsley Ln, Sheffield, MA 01257

  Nestled at the end of a quiet country cul-de-sac, this newly built 5-bedroom, 4.5-bath home embodies refined country living. A dramatic primary suite offers dual walk-in closets and a spa-inspired bath with soaking tub, while a first-floor ensuite bedroom enhances comfort and flexibility. The gas fireplace living room and chef's kitchen create a seamless flow for entertaining, extending to a

  Vashti Poor LANCE VERMEULEN RE, INC

  60 Parsley Ln, Sheffield, MA 01257
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  /51

  $399,900

  • 5 Beds
  • 3 Baths
  • 3,030 Sq Ft

  203 Main St, Hancock, MA 01237

  Charming and flexible use as a single-family or multi-generational home! It has been used as a single family for many years! This Civil War-era farmhouse with 1973 & 1987 additions offers 11 rooms, including 5 bedrooms and 2 kitchens--ideal for in-law living, rental income, or guest space. Located in low-tax Hancock, just 2.8 miles from Jiminy Peak with reliable year-round access. Set on approx.

  Martha Pope BISHOP WEST REAL ESTATE

  203 Main St, Hancock, MA 01237
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  /51

  $399,900

  • 5 Beds
  • 3 Baths
  • 3,030 Sq Ft

  203-205 Main St, Hancock, MA 01237

  Charming and flexible use as a single-family or multi-generational home! This Civil War-era farmhouse with 1973 & 1987 additions offers 11 rooms, including 5 bedrooms and 2 kitchens--ideal for in-law living, rental income, or guest space. Located in low-tax Hancock, just 2.8 miles from Jiminy Peak with reliable year-round access. Set on approx. 0.4 acres with a deck and wooded hillside behind.

  Martha Pope BISHOP WEST REAL ESTATE

  203-205 Main St, Hancock, MA 01237
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  /70

  $895,000

  • 9 Beds
  • 7 Baths
  • 5,267 Sq Ft

  567 S Main St, Sheffield, MA 01257

  Investment opportunity in Sheffield. Versatile investment opportunity set on 11 private acres. This multi-building property, held by the same family for four decades, offers strong income potential with flexible configurations across three separate structures. Main House with (4) 1BR and (1) 2BR apartment, a second 3 BR home, and a three-bay garage. Just 15 minutes from GB and 10 minutes to

  Claire Pollart LANCE VERMEULEN RE, INC

  567 S Main St, Sheffield, MA 01257
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  /19

  $165,000

  • 6 Beds
  • 2.5 Baths
  • 2,550 Sq Ft

  166 Houghton St, North Adams, MA 01247

  Long time family owned two family close to Mass Moca and downtown North Adams - Long term tenants - Unit 166 has a kitchen .living and dining room down with three bedrooms and a full bath up - Unit 164 is the same but has a half bath down - Unit 166 needs to be completely redone - Unit 164 needs updating - - home features a slate roof and replacement windows - Natural gas into home for cooking

  Dennis D'Arcangelo MONARCH REALTY, INC.

  166 Houghton St, North Adams, MA 01247
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  /5

  $179,900

  • 6 Beds
  • 2 Baths
  • 2,376 Sq Ft

  24 Glenwood Ave, Pittsfield, MA 01201

  For sale an approximately 2,376 SF two-family home with a 2-car garage on approximately 0.227 acres of land. The Property is located in close proximity to the center of Pittsfield with easy access to Rts. 7, 8, 8A, 9 & 20.

  John Dill Colebrook Realty Services, Inc.

  24 Glenwood Ave, Pittsfield, MA 01201
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  /30

  $655,000

  • 5 Beds
  • 3 Baths
  • 3,035 Sq Ft

  133 Front St, Great Barrington, MA 01236

  Unique Mixed-Use Property in Downtown HousatonicPrime opportunity for investors or owner-occupants! This charming property features a successful ground-floor retail space and two spacious, income-producing 2-bedroom apartments above. Each unit includes a large kitchen, full bath, washer/dryer hookups, and an enclosed porch with town views.The commercial space has its own kitchen and bath ideal

  Judi Panzano HOUSATONIC REAL ESTATE

  133 Front St, Great Barrington, MA 01236
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  /30

  $380,000

  • 5 Beds
  • 2.5 Baths
  • 3,030 Sq Ft

  145 Bartlett Ave, Pittsfield, MA 01201

  Welcome to this stunning Colonial home, perfectly situated near the vibrant heart of downtown Pittsfield. With 5 spacious bedrooms and 3 bathrooms, this 3030 square foot detached home offers ample space for both relaxation and entertaining. The hardwood flooring throughout the house adds a touch of elegance and warmth. Enjoy hosting gatherings on the large deck, or take a short stroll to the

  Jarrett Hernandez 360BERKSHIRE REALTY GROUP

  145 Bartlett Ave, Pittsfield, MA 01201
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  /50

  $4,985,000

  • 13 Beds
  • 13.5 Baths
  • 9,556 Sq Ft

  2 Kemble St, Lenox, MA 01240

  The Kemble, a registered ''Great Estate'' built in 1881 is located in the heart of the thriving downtown Lenox business district. This classic Colonial Revival building has recently been refreshed with modern furnishings and decor, repurposed as a luxury rental property, and is being offered as a turn key operation. With grand gathering spaces, a well equipped kitchen, handsome mahogany bar, and

  Cameron Volastro STONE HOUSE PROPERTIES, LLC

  2 Kemble St, Lenox, MA 01240
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  /16

  $200,000

  • 6 Beds
  • 2 Baths
  • 1,680 Sq Ft

  138 Robbins Ave, Pittsfield, MA 01201

  One unit is vacant & the other unit rented for $1,800/month, presenting a great opportunity for investors and owner-occupants! This income producing multifamily home is set back from the street and offers two apartments, each one with 3 bedrooms /1 Bath, laundry hookups and its own Lead Paint Compliance Certificate. The first floor unit has a beautifully renovated bathroom. The apartment was

  Maria Liccardi Lamacchia Realty, Inc.

  138 Robbins Ave, Pittsfield, MA 01201
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  /24

  $489,000

  • 5 Beds
  • 3 Baths
  • 3,696 Sq Ft

  321 High St, Dalton, MA 01226

  Welcome to 321 High Street, Dalton! This spacious home offers the perfect balance of New England charm and modern comfort. Located across from Pine Grove Park, it features inviting curb appeal with well-maintained landscaping and a generous backyard. You'll find light-filled rooms with newly refinished hardwood floors, a spacious living room and an updated kitchen with a stunning cathedral

  Cheryl Ryan BISHOP WEST REAL ESTATE

  321 High St, Dalton, MA 01226
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  /42

  $499,000

  • 5 Beds
  • 2 Baths
  • 1,745 Sq Ft

  9 & 14 Bear Hill Rd, Hinsdale, MA 01235

  This offshore Ashmere Lake family compound is a rare find offering lake access just a few steps from your properties. The rustic chic Cottage boasts a lushly landscaped corner lot with overflow parking, 3 bedrooms, yoga room, 1 bath, large living room with pellet stove, a dining room, spacious kitchen, inviting front porch, a wrap-around deck, and a one-car garage. Across the street, you'll find

  Victoria Standring LAMACCHIA REALTY, INC

  9 & 14 Bear Hill Rd, Hinsdale, MA 01235
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  /37

  $729,000

  • 5 Beds
  • 5 Baths
  • 2,698 Sq Ft

  395 Laurel St, Lee, MA 01238

  Incredible location, close to everything Berkshires. One of the most iconic properties in South County located just north of the new housing development in downtown Lee. This property has a total of 3 residential units and 2 commercial units. Unit A ($1,600/mo.) is a two bedroom townhouse style apartment. Unit B ($1,300/mo.) is a two bedroom apartment. Unit C ($950/mo) is a one bedroom apartment.

  Tim Gallagher STONE HOUSE PROPERTIES, LLC

  395 Laurel St, Lee, MA 01238
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  /40

  $1,995,000

  • 6 Beds
  • 8 Baths
  • 10,507 Sq Ft

  14 Pine St, Stockbridge, MA 01262

  Prime Owner-User/Investment Property in the heart of historic Stockbridge. Currently an Educational Facility with Retail, Office and Residential Units. Can be combined for Offices, Medical, Educational, Gallery, Apartments/Condos, or any use that demands a location in one of the most well known and loved towns in America. Fully upgraded mechanicals, large Parking facilities and Handicapped

  Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  14 Pine St, Stockbridge, MA 01262
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  /82

  $2,300,000

  • 5 Beds
  • 4.5 Baths
  • 4,842 Sq Ft

  173 Hillsdale Rd, Egremont, MA 01230

  Nestled in a secluded, serene setting and surrounded by lush gardens, fruit trees, wildlife and protected land on three sides, this one-of-a-kind, custom-built home offers extraordinary privacy and tranquility. Crafted using wood milled directly from the property, this rustic yet contemporary home boasts a wealth of unique details that highlight exceptional craftsmanship and timeless beauty.

  Robert Cohen eXp REALTY

  173 Hillsdale Rd, Egremont, MA 01230
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  /80

  $1,189,900

  • 5 Beds
  • 2.5 Baths
  • 3,087 Sq Ft

  18 Old Farm Ln, Pittsfield, MA 01201

  New Incredible Offer: Seller to pay HOA Fees for 3 Years at closing! Seller offers extra lot for a total of 3 Lots (buyers choice) & Paint Concession $50,000 for Finishing touches! See this Like New -New England Farmhouse ready for you! Over the bridge into the woods escape to a magical setting amidst a woodland preserve of 3+ acres. Build a family compound of your own with 2 extra

  Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

  18 Old Farm Ln, Pittsfield, MA 01201
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  /67

  $2,200,000

  • 5 Beds
  • 3.5 Baths
  • 4,840 Sq Ft

  111 Park St, Williamstown, MA 01267

  Nestled in the center of Williamstown, just steps from Williams College, this stunning two-story Colonial stucco home offers timeless charm and modern comfort. Built in 1907, this 4,100 sq. ft. residence features five spacious bedrooms, three full baths, and one half bath.Set on 1.35 picturesque acres, the property boasts a large post-and-beam barn, a beautifully covered stone patio, and

  Seth Alden ALTON & WESTALL REAL ESTATE AGENCY, LLC

  111 Park St, Williamstown, MA 01267
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  /31

  $4,900,000

  • 5 Beds
  • 6.5 Baths
  • 5,890 Sq Ft

  390 Tamaridge Rd, Great Barrington, MA 01230

  STUNNING LONG VIEWS, RARE 330+ ACRE PARCEL, ABUTS CONSERVATION LAND! Total seclusion and privacy, bucolic countryside with some open meadows and wooded hillside. Once a grand Berkshire estate, the property is comprised of the main Tudor style residence with indoor pool, shingled barn, Dutch colonial multi family dwelling, a guest house & several smaller sheds and workshop. The buildings are all

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  390 Tamaridge Rd, Great Barrington, MA 01230
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  /53

  $3,150,000

  • 5 Beds
  • 4.5 Baths
  • 5,238 Sq Ft

  56 Crooked Hill Rd, Great Barrington, MA 01230

  Alford Stunner! Exceptionally Designed Turnkey Home with Mountain Views!Completed in 2006, this 5200+ sq ft architect-designed home comes to the market for the first time. Meticulously curated materials, interior designer finishes, and a high-end build culminate in this showpiece home on 19.3 acres, with gunite pool and pool house.Upon entry, this home exudes warmth, style, and comfort - the

  Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  56 Crooked Hill Rd, Great Barrington, MA 01230
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  /41

  $1,499,900

  • 12 Beds
  • 7 Baths
  • 7,956 Sq Ft

  45 Forest St, Lee, MA 01238

  This stunning 6-family home sits on 1.5 acres, just a couple minutes away from the Lee Outlets, a convenient location with easy access to the Mass Pike. This multi-family consists of 3 two-bedroom units, 2 one-bedroom units, and a 4 bedroom 2 bath unit. The large unit offers a welcoming front porch, living room, eat-in kitchen, full bath and primary bedroom on the the 1st floor, and 3 bedrooms

  Maria Liccardi Lamacchia Realty, Inc.

  45 Forest St, Lee, MA 01238
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  /4

  $279,900

  • 6 Beds
  • 2 Baths
  • 2,736 Sq Ft

  29 Glenwood Ave, Pittsfield, MA 01201

  Spacious duplex with 3bed 1 bath on each side. Each side has a walk up attic and laundry hook ups.Plenty of off street parking.

  Scott Higuera 413 REAL ESTATE

  29 Glenwood Ave, Pittsfield, MA 01201
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  /51

  $2,975,000

  • 5 Beds
  • 5.5 Baths
  • 3,940 Sq Ft

  19 Mill Rd, Egremont, MA 01230

  Escape to Your Own Lakefront Sanctuary in the Berkshires Nestled in the heart of the picturesque Berkshires, this enchanting lakefront property offers a rare opportunity to create your dream retreat. With over 500 feet of private waterfront, this expansive estate is a haven for those seeking tranquility and natural beauty. Situated on a sprawling parcel of land, this property is perfectly

  Suzann Ward HOUSATONIC REAL ESTATE

  19 Mill Rd, Egremont, MA 01230
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  /24

  $3,490,000

  • 5 Beds
  • 2 Baths
  • 12,225 Sq Ft

  350 Old Cheshire Rd, Lanesborough, MA 01237

  Welcome to Camp Mohawk, a pristine lakefront property in the heart of the Berkshires. Located on Cheshire Reservoir, a virtually uninhabited lake, located just off the main north-south artery of Berkshire County. Once a summer camp, the existing main house and barns are listed on the National Register of Historic Places, and date to the late 1700's. Would make a lovely family compound, or could

  Lisa Hoe THE KINDERHOOK GROUP - PITTSFIELD

  350 Old Cheshire Rd, Lanesborough, MA 01237
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  /52

  $1,675,000

  • 12 Beds
  • 7 Baths
  • 8,881 Sq Ft

  29 Main St, West Stockbridge, MA 01266

  Step into a piece of history with the once Iconic Card Lake Inn Tavern, now transformed into a stunning residential haven in the heart of downtown West Stockbridge. This property offers not only a prime location but also an exceptional living experience, combining modern amenities with charming historic character. The building houses six completely renovated high-end apartments, each thoughtfully

  Suzann Ward HOUSATONIC REAL ESTATE

  29 Main St, West Stockbridge, MA 01266
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  /66

  $6,850,000

  • 5 Beds
  • 3.5 Baths
  • 3,474 Sq Ft

  77 Seekonk Cross Rd, Great Barrington, MA 01230

  Welcome to Meadow Wood This elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lily pond, terraces, pastoral views, and privacy. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/

  Elvia Gignoux WILLIAM PITT SOTHEBY'S - SALISBURY

  77 Seekonk Cross Rd, Great Barrington, MA 01230
• 

  

  /43

  $725,000

  • 7 Beds
  • 6.5 Baths
  • 3,684 Sq Ft

  3 Lake Buel Rd, Great Barrington, MA 01230

  Discover the timeless allure of 'The Turning Point,' a quintessential Berkshire retreat nestled in the hills of Great Barrington. Originally a 1800's stagecoach stop, this enchanting 3600-square-foot property boasts a rich history as a thriving inn, short-term rental and home, offering 7 bedrooms and 6.5 bathrooms. Immerse yourself in its New England charm, complete with a wood stove, propane

  Tony Segalla LANCE VERMEULEN RE, INC

  3 Lake Buel Rd, Great Barrington, MA 01230
• 

  

  /37

  $795,000

  • 6 Beds
  • 3.5 Baths
  • 3,348 Sq Ft

  1151 Hancock Rd, Williamstown, MA 01267

  Nestled in the Berkshires, this historic, colonial home sits on 55 gorgeous pasture/meadow and woodland acres with beautiful mountain views, trails, private pond, babbling brooks, & a three story barn. With 1042.9 ft of frontage, the property holds endless possibilities for subdividing, or to be repurposed for your needs. The house, dating back to 1796, features many outstanding architectural

  Deb Trzcinski STEEPLEVIEW REALTY - ADAMS BRANCH

  1151 Hancock Rd, Williamstown, MA 01267
• 

  

  /4

  $549,000

  • 5 Beds
  • 3 Baths
  • 2,899 Sq Ft

  5, 15, 17 Fuller St, Lee, MA 01238

  Prime Commercial / Residential / Mixed-Use Development Parcel on Route 20. Corner Parcel. Almost a full Acre. Comprised of 2 Lots. High traffic count,. Zoning allows for several uses. **Includes 2 Residential Buildings that can be delivered tenanted, vacant or can be raised by Seller for an additional fee.(note: Property delineation lines on photographs are approximations only.)

  Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  5, 15, 17 Fuller St, Lee, MA 01238

Showing Results 81 - 120, Page 3 of 4