5-Bedroom Homes for Sale in Berkshire County MA

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  /64

  $1,100,000

  • 5 Beds
  • 4.5 Baths
  • 6,128 Sq Ft

  89 Crofut St, Pittsfield, MA 01201

  A Grand Federal-Style Home in the Heart of Town.
Set on 1.18 acres of lush gardens and lawn, this in-town oasis features an in-ground heated swimming pool, pool house, and three-car garage. East and West porches grace this historic residence, lovingly cared for by generations of prominent Berkshire families. Inside, there are four fireplaces, the light-filled chef's kitchen with large

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  89 Crofut St, Pittsfield, MA 01201
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  /34

  $1,269,000

  • 6 Beds
  • 4 Baths
  • 3,334 Sq Ft

  1574 Pleasant St, Lee, MA 01260

  Welcome to The House of HBB – Built in 1815 Rarely does a property so seamlessly combine historic significance and proven profitability. Situated on Pleasant Street and listed on the Historic Register, this meticulously maintained home offers three fully independent units—each successfully run as a 5-Star Airbnb with consistent repeat bookings, strong occupancy, and very little overhead. With a

  Ashley Rose Compass

  1574 Pleasant St, Lee, MA 01260
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  /40

  $360,000

  • 8 Beds
  • 4 Baths
  • 3,266 Sq Ft

  261 Pomeroy Ave, Pittsfield, MA 01201

  Spacious Fully -Rented Duplex Investment OpportunityDiscover an investment opportunity with strong income potential. This 3,266 sqft duplex, built in 1900, offers timeless character combined with functionally. Situated on .41 acres, with plenty of off-street parking, the property features 15 rooms, 8 bedrooms, and 4 full baths across both units, making it ideal for long-term rental stability.

  Marnie Garzone THE KINDERHOOK GROUP - PITTSFIELD

  261 Pomeroy Ave, Pittsfield, MA 01201
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  /31

  $282,000

  • 6 Beds
  • 2 Baths
  • 2,120 Sq Ft

  15 Atlantic Ave, Pittsfield, MA 01201

  Recently Renovated Two-Family Flat - Lead Compliant & Move-In Ready!Discover this nicely updated two-family flat offering comfort, convenience, & modern features. Lead compliant, this property is perfect for owner-occupants or investors alike.Each 3 BR unit boasts fresh finishes & functional layouts!. The fully fenced yard is ideal for pets, play, & entertaining, & the two-car garage provides

  Mary Jane Dunlop BISHOP WEST REAL ESTATE

  15 Atlantic Ave, Pittsfield, MA 01201
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  /35

  $345,000

  • 6 Beds
  • 3 Baths
  • 2,892 Sq Ft

  22 Copley Terrace, Pittsfield, MA 01201

  This inviting Colonial offers six bedrooms and three full bathrooms in a prime location near downtown Pittsfield, schools, restaurants, and all the cultural and recreational attractions the Berkshires have to offer.The first floor features a spacious kitchen, formal dining room, comfortable living room, laundry area, bonus room, and a full bath. The second floor includes four bedrooms and another

  Jose Larios LAMACCHIA REALTY, INC

  22 Copley Terrace, Pittsfield, MA 01201
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  /44

  $290,000

  • 5 Beds
  • 2 Baths
  • 2,584 Sq Ft

  33-35 Hall St, North Adams, MA 01247

  This income-producing two-family home has been recently renovated, with new kitchens featuring granite countertops and new stainless appliances; new tiled bathrooms, new water heaters, electrical updates, painting, among other improvements! Unit 33 features 2 bedrooms 1 bath, and unit 35 has 3 bedrooms and 1 bath. The property sits on a 0.36 acre lot and features a large private wooded backyard.

  Maria Liccardi LAMACCHIA REALTY, INC

  33-35 Hall St, North Adams, MA 01247
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  /6

  $49,900

  • 6 Beds
  • 3 Baths
  • 2,954 Sq Ft

  30 Dover St, North Adams, MA 01247

  Great project for any investors. Large 3 family home with great potential. Run your numbers and check the ARV. This home will not qualify for financing.

  Tyler Scaglione Cameron Real Estate Group

  30 Dover St, North Adams, MA 01247
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  /42

  $725,000

  • 6 Beds
  • 4.5 Baths
  • 3,144 Sq Ft

  138 Seneca Dr, Becket, MA 01223

  Nestled among rock outcrops and only steps from the shores of Indian Lake, this 6 bedroom, four-and-a-half bath home has been a welcoming place for generations. Designed with a contemporary, multi-level layout, its sun-filled spaces connect effortlessly to the outdoors, offering both gathering areas for friends and family as well as private nooks for quiet moments. Views shift with the

  Nikki Carchedi STONE HOUSE PROPERTIES, LLC

  138 Seneca Dr, Becket, MA 01223
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  /50

  $749,000

  • 5 Beds
  • 3.5 Baths
  • 4,008 Sq Ft

  4 Causeway Rd, Peru, MA 01235

  SPACIOUS CONTEMPORARY WITH 800' OF FRONTAGE ON PRISTINE GARNET LAKE. Private 17+ acre non-motorboat lake with two beaches, perfect for swimming, kayaking, fishing, and ice skating. A Berkshire Hill town, Peru offers great scenic beauty and is a haven for outdoor enthusiasts... minutes from the Frances Rice Wildlife Refuge, the Peru Wildlife Management Area, and the Appalachian Trail. In move-in

  Tom Lynch COMPASS MASSACHUSETTS , LLC GB

  4 Causeway Rd, Peru, MA 01235
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  /7

  $225,000

  • 5 Beds
  • 2 Baths
  • 2,244 Sq Ft

  54 Marietta St, North Adams, MA 01247

  Welcome to this spacious 2 family home. The work has been done for you. Interior has been completely remodeled, floors, walls, bathrooms kitchen and a new roof. Don’t miss your chance to make this your new home!

  Raul Portorreal International Real-Estate Investment Group

  54 Marietta St, North Adams, MA 01247
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  /36

  $284,000

  • 5 Beds
  • 2 Baths
  • 2,378 Sq Ft

  89 Robbins Ave, Pittsfield, MA 01201

  Beautifully renovated 2-family flat, perfect for an investor or owner-occupant. This move-in ready property features a brand-new roof, updated heating systems, modern kitchens, stylishly remodeled bathrooms, and more. Each unit offers fresh finishes and comfortable living spaces. Enjoy a large, fenced-in yard--ideal for pets, entertaining, or gardening. Conveniently located near shops, dining,

  Michele Purcell LAMACCHIA REALTY, INC

  89 Robbins Ave, Pittsfield, MA 01201
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  /14

  $399,900

  • 6 Beds
  • 3 Baths
  • 3,016 Sq Ft

  672 N Hoosac Rd Unit 676, Williamstown, MA 01267

  Fantastic opportunity in desirable Williamstown! This charming three-unit multi-family sits on a spacious lot. Each unit offers comfortable living space with solid rental history. The large lot provides off-street parking, green space, or potential for future expansion (buyer to verify). Enjoy beautiful mountain views that add to the property's charm. A rare find--don't miss out!

  Alyssa Sherman MORESI REAL ESTATE PARTNERS

  672 N Hoosac Rd Unit 676, Williamstown, MA 01267
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  /42

  $369,000

  • 7 Beds
  • 3.5 Baths
  • 3,672 Sq Ft

  98 Lincoln St, Pittsfield, MA 01201

  Fantastic opportunity to own this updated 3-family property, perfect for investors or owner-occupants alike. Featuring many recent updates throughout, each unit offers comfortable living with separate utilities for convenience and cost control. The property boasts off-street parking, a strong rental history, and a central location close to shopping, dining, and public transportation. Whether

  Michele Purcell Lamacchia Realty, Inc.

  98 Lincoln St, Pittsfield, MA 01201
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  /48

  $970,000

  • 6 Beds
  • 9 Baths
  • 4,652 Sq Ft

  560 Stockbridge Rd, Lee, MA 01238

  Set on just over seven acres between Lee and Stockbridge, this c.1850 Greek Revival delivers classic Berkshire character with real scale. Nearly 4,700 square feet with a gracious flow, tall windows, and preserved period details. Every bedroom offers an en suite, creating an easy setup for hosting family and friends. Common spaces include a welcoming foyer, two living rooms, a formal dining room,

  Cameron Volastro STONE HOUSE PROPERTIES, LLC

  560 Stockbridge Rd, Lee, MA 01238
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  /10

  $365,000

  • 5 Beds
  • 1.5 Baths
  • 2,490 Sq Ft

  15 Golden Hill Rd, Lee, MA 01238

  This incredibly spacious home built in the early 1900s features 5 bedrooms, an eat-in kitchen, a formal dining room, an office, a family room, a library with built-ins, and a backyard of more than a half acre with distant views and space for a good size garden as well as room for a pool. A fabulous 2-story barn offers extended space awaiting your vision. Mature plantings offer a feeling of

  John Segalla HOUSATONIC REAL ESTATE

  15 Golden Hill Rd, Lee, MA 01238
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  /16

  $230,000

  • 5 Beds
  • 2 Baths
  • 1,768 Sq Ft

  24 Southern Ave, Pittsfield, MA 01201

  Excellent investment opportunity! This recently updated multi-family home features a 3-bedroom, 1 bathroom downstairs unit and a 2-bedroom, 1-bathroom upstairs unit. Updates include a new roof, gas furnace, radiators, drywall, electrical, and plumbing. Both kitchens and bathrooms have been fully renovated. The downstairs unit has vinyl flooring and a kitchen with granite countertops, while the

  Derek Greene The Greene Realty Group

  24 Southern Ave, Pittsfield, MA 01201
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  /8

  $535,000

  • 8 Beds
  • 8 Baths
  • 2,657 Sq Ft

  180 Center St, Lee, MA 01238

  Discover an exceptional investment opportunity to own two duplex homes on a single parcel, perfect for investors looking for a practical investment in the town of Lee. Four units total, these properties are ideal for generating consistent rental income. Close to downtown, shopping, major employers as well as banking and all popular Berkshire attractions. Tenants enjoy attached, private garaged

  Tim Gallagher STONE HOUSE PROPERTIES, LLC

  180 Center St, Lee, MA 01238
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  /14

  $1,475,000

  • 16 Beds
  • 16 Baths
  • 8,608 Sq Ft

  14 Highland Ave, Pittsfield, MA 01201

  Excellent 8-Unit Investment Opportunity-5 minute walk to the Lake!Clean, well-maintained multifamily property featuring 8 total units with separate utilities. Each unit includes central A/C. Property offers private, dedicated parking for tenants. Prime location--just minutes from major hospitals, large employers, shopping, and public transit. High-demand rental area with strong occupancy history.

  Tim Gallagher STONE HOUSE PROPERTIES, LLC

  14 Highland Ave, Pittsfield, MA 01201
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  /46

  $390,000

  • 6 Beds
  • 2.5 Baths
  • 3,200 Sq Ft

  36 Chickering St, Pittsfield, MA 01201

  Charming Duplex in Southeast Pittsfield - Great Investment Opportunity!Welcome to this well-maintained duplex nestled in a desirable Southeast Pittsfield neighborhood! The layout on both sides includes a living room, dining room, large kitchen, and three comfortably sized bedrooms. Unit #38 has one bath and laundry hook-ups in the basement, while Unit #36 has 1.5 baths and laundry hook-ups on the

  Chris LaPatin LAMACCHIA REALTY, INC

  36 Chickering St, Pittsfield, MA 01201
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  /36

  $115,000

  • 7 Beds
  • 2.5 Baths
  • 2,228 Sq Ft

  376 Fenn St, Pittsfield, MA 01201

  Great project for investor or handy home owner. Build instant equity in this large 2 family home. 2 car garage. Large open rooms throughout. Great location and lot.

  Tyler Scaglione Cameron Real Estate Group

  376 Fenn St, Pittsfield, MA 01201
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  /54

  $979,000

  • 5 Beds
  • 4.5 Baths
  • 2,800 Sq Ft

  850 Summer St, Lee, MA 01238

  Welcome to the Katydid Cottage, a thoughtfully updated Berkshire home full of modern amenities and historic charm. This five bedroom, four and a half bath freestanding condominium features a bright kitchen, large dining room, living room with gas fireplace insert, powder room, and a primary suite all on the first floor. Upstairs you will find four more bedrooms, two with ensuite bathrooms, and

  Katie Williams STONE HOUSE PROPERTIES, LLC

  850 Summer St, Lee, MA 01238
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  /56

  $979,000

  • 5 Beds
  • 4.5 Baths
  • 2,800 Sq Ft

  850 Summer St Unit M14, Lee, MA 01238

  Welcome to the Katydid Cottage, a thoughtfully updated Berkshire home full of modern amenities and historic charm. This five bedroom, four and a half bath freestanding condominium features a bright kitchen, large dining room, living room with gas fireplace insert, powder room, and a primary suite all on the first floor. Upstairs you will find four more bedrooms, two with ensuite bathrooms, and

  Katie Williams STONE HOUSE PROPERTIES, LLC

  850 Summer St Unit M14, Lee, MA 01238
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  /7

  $595,000

  • 17 Beds
  • 4 Baths
  • 13,608 Sq Ft

  20 Wesleyan St, North Adams, MA 01247

  Fully operating, long term tenants, lot for parking, each apartment has its own forced hot air furnace and gas hot water tank. Many updates including new roof in 2015, basement engineered fortified, new furnaces over the years. 3 stalls of storage space. Tenants pay their own utilities. The building was repainted last summer,2024.

  David White OwnerEntry.com

  20 Wesleyan St, North Adams, MA 01247
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  /58

  $4,995,000

  • 7 Beds
  • 8 Baths
  • 13,261 Sq Ft

  319 Under Mountain Rd, Lenox, MA 01240

  Pine Needles.Built circa 1900 as a Berkshire ''cottage'' in the era of grand summer estates, this historic property blends the dignity of Colonial Revival architecture with the relaxed elegance of an Italian villa and the artisanal detail of the Arts & Crafts movement. Sited on 80 private acres just minutes from the heart of Lenox, the estate offers breathtaking southern views, rolling forest,

  Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  319 Under Mountain Rd, Lenox, MA 01240
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  /6

  $75,000

  • 12 Beds
  • 5 Baths
  • 4,032 Sq Ft

  48 Brown St, Pittsfield, MA 01201

  Opportunity knocks! This 4-family property has suffered significant fire damage and is being sold as-is for land value. Ideal tear down project with endless redevelopment potential. The lot includes a detached garage and offers ample space for new construction. Bring your vision and rebuild in a growing area with strong rental demand. Cash or construction financing only. All offers considered.

  Xavier Cruz Fathom Realty

  48 Brown St, Pittsfield, MA 01201
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  /12

  $175,000

  • 6 Beds
  • 2 Baths
  • 2,128 Sq Ft

  242 Wahconah St, Pittsfield, MA 01201

  Investor Special! This gutted duplex offers a blank canvas with 6 bedrooms, 2 bathrooms, and 2,000 sqft of space, plus the possibility of additional living space in the attic. this property features a large backyard with a serene water stream, A standing garage remains on site for additional storage or future use. Situated on a 13,108 sqft lot, can also be bundled with 40 Pecks Rd & 48 Brown st

  Xavier Cruz Fathom Realty

  242 Wahconah St, Pittsfield, MA 01201
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  /24

  $569,000

  • 5 Beds
  • 3.5 Baths
  • 3,307 Sq Ft

  867 Notch Rd, Cheshire, MA 01225

  A charming, spacious Colonial with privacy, and lovely grounds. Breathtaking mountain views. Built in 2005 and set on 7.25 acres, this 5-bedroom, 4.5-bathroom residence offers 3,307 square feet of living space. Two primary suites, one up and one down. The open-concept kitchen flows seamlessly into a great room, perfect for entertaining. This home does need work but is priced accordingly. Make

  Marnie Garzone THE KINDERHOOK GROUP - PITTSFIELD

  867 Notch Rd, Cheshire, MA 01225
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  /16

  $939,000

  • 11 Beds
  • 10.5 Baths
  • 2,016 Sq Ft

  3949 Jacobs Ladder Rd, Becket, MA 01223

  A unique lakefront cedar home with 8 room motel. many possibilities.Approximately 2.7 acres with over 500 ' lake frontage on Beautiful Greenwater Pond . Close to Appalachian trail and many Berkshire cultural and recreational venues.

  Anthony Caropreso MACCARO REAL ESTATE

  3949 Jacobs Ladder Rd, Becket, MA 01223
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  /54

  $649,000

  • 5 Beds
  • 2.5 Baths
  • 2,750 Sq Ft

  168 Main St, Sheffield, MA 01257

  Historic village living at its finest. This expansive Turn-of-the-Century Sheffield home is rich with original detail, from its warm wood floors to a magnificent fieldstone fireplace. The property boasts a large, private yard, offering ample space for gardening, recreation, or outdoor entertainment. A substantial barn on the property provides excellent potential for a workshop, studio, or extra

  Tony Segalla LANCE VERMEULEN RE, INC

  168 Main St, Sheffield, MA 01257
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  /44

  $1,200,000

  • 9 Beds
  • 4.5 Baths
  • 8,406 Sq Ft

  2049 S Undermountain Rd, Sheffield, MA 01257

  An exceptional opportunity awaits on 11 private acres in Sheffield. This unique property, currently utilized as a functional therapy facility, offers a massive footprint and a flexible canvas for your next venture. The centerpiece is an 8,000+ sq. ft. building comprised of over 10 offices, multiple conference rooms, common areas, and three residential apartments, creating an ideal setup for a

  Tony Segalla LANCE VERMEULEN RE, INC

  2049 S Undermountain Rd, Sheffield, MA 01257
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  /37

  $600,000

  • 6 Beds
  • 5 Baths
  • 3,502 Sq Ft

  53 Mahaiwe St, Great Barrington, MA 01230

  A prime investment opportunity in the heart of downtown Great Barrington. This 5-unit residential property features a desirable mix of four one-bedroom apartments and one two-bedroom unit. A significant advantage for this building is that all units are serviced by their own separate heating and electrical systems. Its convenient downtown location ensures high demand due to walking proximity to

  Tony Segalla LANCE VERMEULEN RE, INC

  53 Mahaiwe St, Great Barrington, MA 01230
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  /62

  $1,330,000

  • 16 Beds
  • 10 Baths
  • 8,870 Sq Ft

  6 Manville St, Great Barrington, MA 01230

  A prime investment opportunity in the heart of downtown Great Barrington. This 10-unit residential property features a desirable mix of six spacious two-bedroom apartments and four one-bedroom units. The two-bedroom apartments are particularly appealing, all offering private balconies and fireplaces, with three of these premium units also including formal dining rooms and Jack-and-Jill style

  Tony Segalla LANCE VERMEULEN RE, INC

  6 Manville St, Great Barrington, MA 01230
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  /57

  $279,000

  • 7 Beds
  • 2 Baths
  • 2,723 Sq Ft

  34-36 Crandall St, Adams, MA 01220

  Welcome to your next investment or forever home! Nestled on a serene, tree-lined street, with views of Mt. Greylock, is known for its charm and community feel, this classic home offers a rare opportunity to create value and build equity in a highly desirable location.Each unit features 3 bedrooms and 1 1/2 bath with spacious layouts and original character --hardwood floors, large windows, and

  Lisa Mendel BURNHAM GOLD REAL ESTATE, LLC

  34-36 Crandall St, Adams, MA 01220
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  /45

  $379,900

  • 5 Beds
  • 2 Baths
  • 2,120 Sq Ft

  127 Gamwell Ave, Pittsfield, MA 01201

  Owned Solar Panels! Tucked away at the end of a quiet cul-de-sac, this spacious five bedroom, two bathroom home offers 2,020 square feet of living space along with additional space in the basement. As you enter the home, you will notice hardwood floors throughout the main level that features three of the bedrooms, laundry, and one full bathroom. The bright living area flows easily into the dining

  Cory Evangelisto NOCHER REALTY

  127 Gamwell Ave, Pittsfield, MA 01201
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  /68

  $2,200,000

  • 5 Beds
  • 4.5 Baths
  • 3,354 Sq Ft

  176 W Center Rd, West Stockbridge, MA 01266

  The lovely approach to this gorgeous estate property ensures serenity, privacy, and the beauty of living in the country and includes a 3 bed 2 1/2 bath main house and a gorgeous architect designed guest house. Offering 2 ensuite bedrooms with balconies, dramatic exposed beams, vaulted ceilings, and gas fireplace the guest house is an extraordinary place to host family and friends both

  Lori Rose STONE HOUSE PROPERTIES, LLC

  176 W Center Rd, West Stockbridge, MA 01266
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  /22

  $279,900

  • 8 Beds
  • 3 Baths
  • 3,000 Sq Ft

  23-27 Gallup St, North Adams, MA 01247

  Three family investment opportunity in the heart of North Adams that is perfectly situated near downtown, Mass MoCA, MCLA, shopping, and local schools. Offering two units with three bedrooms and one bathroom and the final unit featuring two bedrooms and one bathroom. Each of the three units has been updated over recent years, along with a newer heating system and updated electrical for the

  Cory Evangelisto NOCHER REALTY

  23-27 Gallup St, North Adams, MA 01247
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  /32

  $1,250,000

  • 5 Beds
  • 5.5 Baths
  • 4,645 Sq Ft

  7 Perry Rd, Sandisfield, MA 01255

  WHERE EVERY SEASON FEELS LIKE HOME16 acres at the end of a quiet country road where your shoulders drop the moment you arrive. This five bedroom retreat with over 4,600 square feet gets Berkshire living right: soaring great room with fireplace, granite kitchen, four-season sunroom, and that incredible finished lower level with radiant floors, full bar, and walkout to covered patio. Mudroom with

  Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  7 Perry Rd, Sandisfield, MA 01255
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  /65

  $899,900

  • 6 Beds
  • 4 Baths
  • 3,818 Sq Ft

  108 Berkshire Dr, Williamstown, MA 01267

  A rare chance to own two attached full size charming houses in one of the most coveted neighborhoods! Abuts 30 acres of conservation land and offers direct access to The Spruces Park, Hoosic & Green River walk/ swimming area, public tennis courts, and Mohican multi-use bike/walk path! Original Home: (Built in 1953, updated in 2016) it has total privacy, deck, 2 bedrooms, 1 bath, a large living

  Donna DiGrigoli DIGRIGOLI REAL ESTATE

  108 Berkshire Dr, Williamstown, MA 01267
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  /41

  $344,900

  • 6 Beds
  • 3 Baths
  • 3,366 Sq Ft

  151 Onota St, Pittsfield, MA 01201

  First Bulk showings/open house 6/13/25 11-12:30! Welcome to this fully rented professionally managed 3-family investment opportunity at 151 Onota St in Pittsfield! Each spacious unit features 2 bedrooms and 1 bathroom, offering excellent rental income potential. The second and third floors are occupied by long-term tenants, while the first floor welcomed new tenants as of June 1st. Don’t miss

  Michael Johnson Lock and Key Realty Inc.

  151 Onota St, Pittsfield, MA 01201
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  /66

  $2,250,000

  • 5 Beds
  • 6 Baths
  • 5,477 Sq Ft

  1030 West St, Pittsfield, MA 01201

  1030 West is a bespoke family compound on 6 acres between Onota Lake and Pittsfield State Forest, offering refined country living with city convenience. The historic main house, decorated by designer Heidi Caillier and featured in her book Memories of Home, has been thoughtfully renovated with timeless materials - custom cabinetry, marble, limestone, Waterworks fixtures, designer and vintage

  Tracy Crawford COMPASS MASSACHUSETTS , LLC GB

  1030 West St, Pittsfield, MA 01201

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