5-Bedroom Homes for Sale in Berkshire County MA

/45
$395,000
- 5 Beds
- 2 Baths
- 2,120 Sq Ft
127 Gamwell Ave, Pittsfield, MA 01201

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 room that connects

Cory Evangelisto NOCHER REALTY

127 Gamwell Ave, Pittsfield, MA 01201
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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
/38
$1,100,000
- 5 Beds
- 3.5 Baths
- 3,194 Sq Ft
33 Interlaken Rd, Stockbridge, MA 01262

Enjoy convenient one level living in this expanded contemporary ranch. Super location - Located less than 5 minutest to the main gates of Tanglewood, the Stockbridge Bowl for swimming, and Gould Meadows for a nature lovers hike. Sited at the end of a long winding driveway this 2+ acre parcel is level and sunny (ideal for a pool). 5+ bedrooms and 3 1/2 bathrooms including a suite with a

Lori Rose STONE HOUSE PROPERTIES, LLC

33 Interlaken Rd, Stockbridge, MA 01262
/65
$970,000 Open House 8/10
- 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
/50
$195,000
- 6 Beds
- 2.5 Baths
- 3,216 Sq Ft
27 Daniels Ave, Pittsfield, MA 01201

Spacious side-by-side duplex offering three bedrooms in each unit. Hardwood floors throughout each unit along with a front/rear porch, first floor laundry, and separate utilities. Loads of additional space in attic and basement for storage or potential future expansion of living space. HUD Home. LBP. Sold ''AS IS'' by elec. bid only. Prop avail 06-12-25. Bids due by 06-22-25 by 11:59 PM Central

Cory Evangelisto NOCHER REALTY

27 Daniels Ave, Pittsfield, MA 01201
/41
$350,000
- 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
/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
/27
$275,000
- 6 Beds
- 2 Baths
- 2,764 Sq Ft
132-134 Crest St, North Adams, MA 01247

Extremely well-maintained 2-family home in desirable North Adams location. Both units are bright, clean, and spacious with open floor plans and excellent natural light. Ideal for owner-occupant or investor. Property features generous room sizes, a nicely kept yard, and strong rental potential. Move-in ready with pride of ownership throughout. Don't miss this turnkey opportunity!

Hannah Klammer MORESI REAL ESTATE PARTNERS

132-134 Crest St, North Adams, MA 01247
/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
/3
$229,000
- 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
/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
/50
$1,950,000
- 5 Beds
- 4.5 Baths
- 4,301 Sq Ft
20 E Dugway Rd, Lenox, MA 01240

Lenox Estate on 36 Acres - Two HomesJust one mile from the center of Lenox, this unique estate offers exceptional space and versatility with two separate residences. The main home boasts 4,100 square feet with five bedrooms and three and a half bathrooms--perfect for spacious living or entertaining. The second home is a charming 1,200-square-foot residence with two bedrooms and two full baths,

Tanya Shepardson LAMACCHIA REALTY, INC

20 E Dugway Rd, Lenox, MA 01240
/48
$5,775,000
- 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
/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
/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
/53
$995,000
- 6 Beds
- 6 Baths
- 5,198 Sq Ft
68 Colt Rd, Pittsfield, MA 01201

Nestled in a charming historic southeast Pittsfield neighborhood, this 4+ bedroom, 5+ bath gem was brought to life in 1914 by the talented architects Harding and Seaver. Their impressive portfolio features notable landmarks like the Berkshire Museum and Lenox Town Hall, showcasing their remarkable contribution to the area's rich history.This grand, yet comfortable home spans four inviting levels!

Carrie Wright WILLIAM PITT SOTHEBY'S - LENOX

68 Colt Rd, Pittsfield, MA 01201
/49
$1,875,000
- 5 Beds
- 5.5 Baths
- 3,225 Sq Ft
5 Easland Rd, West Stockbridge, MA 01266

A Home Designed for Living and RetreatNestled at the base of Tom Ball Mountain on over 10 private acres, 5 Easland Road is a custom-designed contemporary sanctuary where nature, luxury, and thoughtful craftsmanship come together in perfect harmony.This 5-bedroom, 5.5-bath home features soaring vaulted ceilings, dramatic walls of glass, and gleaming hardwood floors throughout. Each of the three

Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

5 Easland Rd, West Stockbridge, MA 01266
/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
/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
/52
$765,000
- 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
/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
/28
$289,900
- 7 Beds
- 3 Baths
- 2,302 Sq Ft
57 Beacon St, North Adams, MA 01247

Beautifully Maintained 3-Family Flat - Ideal for Owner-Occupant or Savvy Investor. This stunning, well-maintained 3-family flat offers a perfect blend of charm, modern updates, and investment potential. Each unit has been thoughtfully renovated. Spacious and sunlit interiors feature updated kitchens, refreshed bathrooms, and updated flooring.Whether you're looking to live in one unit and rent the

Michele Purcell LAMACCHIA REALTY, INC

57 Beacon St, North Adams, MA 01247
/61
$2,995,000
- 5 Beds
- 8 Baths
- 5,508 Sq Ft
258 Sandisfield Rd, New Marlborough, MA 01230

Magnficent Modern Farmhouse designed by CRISP ARCHITECTS and custom built for the owner. Estate grounds, quiet elegance and privacy. Main House, Guest House and Pool House on 10 Acres. The Main House was designed to offer soaring ceilings and plenty of natural light. The Den w/ Fireplace will be your ideal retreat, and the dine-In Kitchen will please any gourmet. First floor Primary Bedroom w/

Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

258 Sandisfield Rd, New Marlborough, MA 01230
/38
$1,900,000
- 6 Beds
- 3 Baths
- 3,000 Sq Ft
123 Bock Way, New Marlborough, MA 01230

BERKSHIRE LAKE FRONT WITH BEAUTIFUL WESTERN VIEWS ACROSS THE LENGTH OF LAKE BUEL. Premiere motor boat lake. With 6 bedrooms and 3 full baths there is room for your extended family or friends. Walls of windows allow lake views from most rooms. Open plan for relaxing after a long day swimming, boating, fishing or relaxing on the water. Lovely out door areas include a deck, patio and steps to your

Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

123 Bock Way, New Marlborough, MA 01230
/51
$419,900
- 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
/51
$419,900
- 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
/75
$895,000
- 9 Beds
- 7 Baths
- 5,267 Sq Ft
567 S Main St, Sheffield, MA 01257

Charming Multi-Home Property in Sheffield. Welcome to a rare homestead tucked away on 11 acres of peace and privacy in Sheffield. This inviting property offers an ideal setup for multi-generational living or families seeking extra space and privacy. Main House with (4) 1BR and (1) 2BR apartments, a second 3 BR home, and a three-bay garage. A short drive to Great Barrington (15 mins) and North

Claire Pollart LANCE VERMEULEN RE, INC

567 S Main St, Sheffield, MA 01257
/19
$175,000
- 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
/15
$388,000
- 6 Beds
- 3.5 Baths
- 2,972 Sq Ft
79 Chestnut St, North Adams, MA 01247

Step into history with this stunning Victorian-era gem. A three Unit apartment Bldg. The First Floor unit has 3 bedrooms 1.5 Baths, Featuring classic hardwood flooring, soaring high ceilings and natural woodwork, Enjoy seamless transitions between the dining and living rooms through elegant pocket French doors on the first floor, which also includes a big kitchen offering a grand foyer with a

Michael Hernandez 360BERKSHIRE REALTY GROUP

79 Chestnut St, North Adams, MA 01247
/44
$539,000
- 5 Beds
- 2.5 Baths
- 2,994 Sq Ft
100 Holmes Rd, Pittsfield, MA 01201

Classic elegance meets modern living in this stately Colonial set on a large corner lot in a highly desired neighborhood, with circular driveway for easy in and out access. Gracious entry, hardwood floors, an updated eat in kitchen plus a formal dining room with original leaded glass hutch and a formal living room. The stunning great room addition, with separate entrance and access to deck and

Victoria Standring LAMACCHIA REALTY, INC

100 Holmes Rd, Pittsfield, MA 01201
/13
$269,000
- 6 Beds
- 2 Baths
- 3,081 Sq Ft
61 Pomeroy Ave, Pittsfield, MA 01201

Investment Opportunity on Pomeroy Ave! 2 Family flat with each unit boasting a spacious layout with 3 bedrooms and 1 full bath. Both units are currently rented, offering immediate income. Convenient location close to the heart of downtown and the cultural district of Pittsfield.

Jessie Carlino MACCARO REAL ESTATE

61 Pomeroy Ave, Pittsfield, MA 01201
/31
$380,000
- 7 Beds
- 3 Baths
- 2,890 Sq Ft
132 E Quincy St, North Adams, MA 01247

Well maintained 3 family home at a great price. Large open units with full sized bedrooms. Off street parking. Large lot. Do the numbers on this property it's a great investment or owner occupied home. Effective the end of June, all units will be occupied.

Tyler Scaglione Cameron Real Estate Group

132 E Quincy St, North Adams, MA 01247
/48
$995,000
- 7 Beds
- 4 Baths
- 2,998 Sq Ft
49 South St, Great Barrington, MA 01230

Immaculate home on ''The Hill'' with stunning hardwood floors and abundant natural light from its many large windows. This versatile three-level property is currently enjoyed as a stately single-family residence, but can seamlessly be divided into two separate apartments, offering a range of layout options and rental income potential. The ground floor features a bright, modern kitchen, a spacious

Kate Lascar COMPASS MASSACHUSETTS , LLC GB

49 South St, Great Barrington, MA 01230
/49
$795,000
- 5 Beds
- 2.5 Baths
- 4,078 Sq Ft
40 Commonwealth Ave, Pittsfield, MA 01201

Immaculately restored antique Colonial dripping with charm offering modern conveniences. Chef's kitchen with Quartz counters, glass back splash, beautiful cabinets, and double sized Wolf Range. Entertaining is made easy with a large dining area, grand fire-placed living room with floor to ceiling windows overlooking the private and lush green lawn. Glorious master suite with new spa like bath.

Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

40 Commonwealth Ave, Pittsfield, MA 01201
/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
/30
$719,000 Open Fri 1PM - 2:30PM
- 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
/26
$390,000
- 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
/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
/36
$430,000
- 5 Beds
- 2 Baths
- 2,858 Sq Ft
6 Crandall St, Adams, MA 01220

Step into this timeless elegance with this spacious 5-bedroom, 2-bath Colonial built in 1900 in a historic district. Full of classic charm inside and out, including original architectural details, hardwood floors, wide trim, and tall ceilings. Two full staircases, a formal front staircase, and a more private back staircase that adds historic charm and functionality. The main floor boasts of

Barbara DeMers NOCHER REALTY

6 Crandall St, Adams, MA 01220

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