Homes for Sale in Berkshire County MA with 5-Bedrooms

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  /32

  $650,000

  • 5 Beds
  • 4 Baths
  • 2,499 Sq Ft

  73 Christian Hill Rd, Great Barrington, MA 01230

  Investors zoom in on this property, we have an income producing property. 3 of the 4 units are rented and all tenants are all current. The 4th unit is open for one more tenant. Property has been remodeled, we have a new roof with warranty, foundation work to reinforce this property, new floors in all the units, bathrooms are renovated, the entire interior has been repainted, Kitchen remodel, New

  

  Cristian Sanchez

  COHEN & WHITE ASSOCIATES

  (413) 779-9020

  73 Christian Hill Rd, Great Barrington, MA 01230
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  /47

  $650,000

  • 5 Beds
  • 3.5 Baths
  • 3,074 Sq Ft

  161 Leona Dr, Pittsfield, MA 01201

  Set in one of Southeast Pittsfield's most desirable neighborhoods, this very sunny and impeccably maintained home offers the perfect balance of gracious living, flexible space, and effortless entertaining. Lovingly cared for by its current owner, the home unfolds with elegant formal rooms, hardwood floors, and a warm wood burning fireplace anchoring the living room. The heart of the home is an

  

  Nick Geranios

  WILLIAM PITT SOTHEBY'S - LENOX

  (413) 570-8931

  161 Leona Dr, Pittsfield, MA 01201
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  /32

  $200,000

  • 8 Beds
  • 4 Baths
  • 5,142 Sq Ft

  32-38 Spring St, North Adams, MA 01247

  This is a four-family property. Property is VACANT. Seller is conveying lot 56-A & Lot 56-B Updated mechanicals ready for the next owner to complete. Each unit has 2 bedrooms, 1 bathroom, and a bigger living room space with windows that allow lots of natural light to shine through. The kitchen is a moderate size giving enough area for people to maneuver. The property is located close to schools,

  

  Michael Hernandez

  360BERKSHIRE REALTY GROUP

  (413) 966-0983

  32-38 Spring St, North Adams, MA 01247
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  /42

  $2,649,000

  • 6 Beds
  • 6.5 Baths
  • 6,225 Sq Ft

  250 West St, Lenox, MA 01240

  Seconds—not minutes—from Tanglewood’s main gate, this reimagined contemporary estate in Lenox is tucked into a sunlit woodland setting offering rare privacy and unrivaled proximity. Originally built in 2017 and completely updated in 2020, the home features soaring ceilings, rich mahogany and cherry finishes, a chef’s kitchen, and multiple entertaining spaces. The ground-floor primary suite is

  

  Selina Lamb

  Birch Properties

  (413) 423-1264

  250 West St, Lenox, MA 01240
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  /8

  $1,719,000

  • 37 Beds
  • 24 Baths
  • 21,162 Sq Ft

  306 South St, Pittsfield, MA 01201

  Offered as a 7-property portfolio, totaling 21 units, this package includes a mix of multifamily properties and a single-family home with value-add potential. Several units are tenant-occupied, providing immediate income with upside potential, while others units require renovation, allowing investors to implement a phased improvement strategy. The portfolio currently generates an in-place NOI of

  

  Corey Bishop

  BISHOP WEST REAL ESTATE

  (413) 798-8328

  306 South St, Pittsfield, MA 01201
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  /39

  $325,000

  • 12 Beds
  • 1 Bath
  • 4,215 Sq Ft

  292 West St, Pittsfield, MA 01201

  This large residential property offers exceptional income potential in a strong Pittsfield rental market. With 12 bedrooms and 3.5 bathrooms, it supports high-capacity occupancy and steady cash flow. The full basement provides extensive storage and includes areas where two former bathrooms once existed, offering a foundation for future updates. A full standing attic adds valuable expansion

  

  Gary Fuls Jr

  RE/MAX Transitions

  (413) 884-5511

  292 West St, Pittsfield, MA 01201
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  /69

  $525,900

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

  144 Brombach St, Pittsfield, MA 01201

  Beautiful, spacious 6 bedroom, 3 updated bath, 4000+sf home, custom built and nestled between two lakes with incredible views in the heart of the picturesque Berkshire Mountains! Walk to Onota Lake in approximately 9 minutes and enjoy a 5 minute drive to Pontoosuc Lake both suitable for kayaking, fishing, swimming, picnicking and more. Enjoy the convenience of 2 laundry rooms and two updated

  Darcy Reid MOCKINGBIRD REAL ESTATE

  144 Brombach St, Pittsfield, MA 01201
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  /71

  $5,650,000

  • 11 Beds
  • 10 Baths
  • 9,748 Sq Ft

  25 W Sheffield Rd, Great Barrington, MA 01230

  Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of future for generations

  Lauren Molk ELYSE HARNEY REAL ESTATE

  25 W Sheffield Rd, Great Barrington, MA 01230
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  /38

  $4,995,000

  • 5 Beds
  • 5.5 Baths
  • 5,002 Sq Ft

  764 E Hill Rd, New Marlborough, MA 01230

  WHERE THE WORLD FALLS AWAY 227 acres. 227 years. At East Hill Road's summit, East Hill Farm is a fully realized estate where infrastructure, land, and possibility are complete and in place. The 1798 Thomas Shepard House-museum-quality restoration featuring 5 bedrooms, 5.5 baths, 5 fireplaces, original King's board floors, hand-blown glass windows-awaits your vision for kitchens and baths. Modern

  Karen Climo William Pitt Sotheby's Int'l

  764 E Hill Rd, New Marlborough, MA 01230
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  /86

  $2,000,000

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

  173 Hillsdale Rd, Egremont, MA 01230

  Surrounded on three sides by Nature Conservancy-protected land, 173 Hillsdale Road is one of the most private and extraordinary estates in the Berkshires -- a handcrafted sanctuary where the wilderness is literally your backyard. Moose, deer, bear, fox, and turtles roam master-gardened grounds tended with rare care; fruit trees, a garden pond, mature perennial beds, and lush native plantings make

  Robert Cohen eXp REALTY

  173 Hillsdale Rd, Egremont, MA 01230
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  /24

  $2,750,000

  • 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. Set on Cheshire Reservoir--a serene, largely uninhabited lake--the property offers both privacy and convenient access just off Berkshire County's main north-south route.Once a summer camp, the estate features an existing main house and barns listed on the National Register of Historic Places, dating back to the

  Lisa Hoe THE KINDERHOOK GROUP

  350 Old Cheshire Rd, Lanesborough, MA 01237
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  /49

  $349,900

  • 7 Beds
  • 2.5 Baths
  • 2,870 Sq Ft

  5 Monteleone Place, Pittsfield, MA 01201

  Large side-by-side two family brick home with a total of 6 garage bays: 2-car attached garage plus detached 4-bay garage. Unit 6 is vacant and has been renovated. The first floor offers an enclosed porch, new beautiful kitchen with quartz countertops and stainless appliances, dining room, living room and full bathroom. The layout offers a possibility to turn one of the rooms into a first floor

  Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  5 Monteleone Place, Pittsfield, MA 01201
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  /27

  $385,000

  • 6 Beds
  • 6 Baths
  • 2,260 Sq Ft

  37 Melville St, Pittsfield, MA 01201

  Six unit multi-family investment property located in the heart of downtown Pittsfield. Located footsteps from shopping, restaurants, an more!. Includes six studio apartments, vinyl siding, and separate electricity for each unit.

  Cory Evangelisto NOCHER REALTY

  37 Melville St, Pittsfield, MA 01201
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  /28

  $1,250,000

  • 14 Beds
  • 14 Baths
  • 9,928 Sq Ft

  40 Reed St, Pittsfield, MA 01201

  14 Unit investment opportunity! Located just outside of downtown Pittsfield and within walking distance to shops, restaurants, and the Colonial Theater. Classic brick exterior and excellent off street parking. All units feature one bedroom and separate utilities. Coin-op laundry located on site for additional income.

  Cory Evangelisto NOCHER REALTY

  40 Reed St, Pittsfield, MA 01201
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  /26

  $680,000

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

  301 Fenn St, Pittsfield, MA 01201

  8 Unit investment opportunity! Located just outside of downtown Pittsfield and within walking distance to shops, restaurants, schools, and parks. Low maintenance exterior with loads of off street parking. All units feature one bedroom with separate heat and electricity. Coin-op laundry located on site for additional income.

  Cory Evangelisto NOCHER REALTY

  301 Fenn St, Pittsfield, MA 01201
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  /41

  $4,850,000

  • 13 Beds
  • 13.5 Baths
  • 9,510 Sq Ft

  2 Kemble St, Lenox, MA 01240

  The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental.The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a

  Cameron Volastro WILLIAM PITT SOTHEBY'S - LENOX

  2 Kemble St, Lenox, MA 01240
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  /18

  $1,500,000

  • 20 Beds
  • 18 Baths
  • 8,653 Sq Ft

  162 Woodlawn Ave, Pittsfield, MA 01201

  162 Woodlawn Ave is comprised of two (2) 2-Bedroom/1-Bathroom units, eleven (11) 1-Bedroom/1-Bathroom units, and five (5) Studio units with 8,653 square feet of gross living area in 11,653 square feet of gross area. The Property is situated upon a 0.47-acre parcel and offers twenty (20) off-street parking spaces. The Property is well-positioned within Pittsfield’s established Morningside

  Michael Bradley Horvath & Tremblay

  162 Woodlawn Ave, Pittsfield, MA 01201
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  /36

  $265,000

  • 5 Beds
  • 2 Baths
  • 1,452 Sq Ft

  20 Marietta St, North Adams, MA 01247

  20 Marietta St, North Adams is fully renovated, move-in ready, and packed with value.This spacious 5 bedroom, 2 full bath home has been completely redone from top to bottom. Featuring a brand new roof, all new appliances, updated kitchen and bathrooms, and new flooring throughout, every detail has been taken care of. Clean, modern finishes give the home a fresh feel while maintaining a practical,

  Christian Garner NOCHER REALTY

  20 Marietta St, North Adams, MA 01247
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  /38

  $259,900

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

  165 Appleton Ave, Pittsfield, MA 01201

  Classic two family brick colonial with many possibilities! Including a front/rear porch, two separate yards on each side, and off street parking. Enter each side into a wide, open hallway with the original hardwood floors throughout. The left side has four bedrooms and one bathroom with potential for a second bathroom off the kitchen. The right side has been split into two smaller units with

  Cory Evangelisto NOCHER REALTY

  165 Appleton Ave, Pittsfield, MA 01201
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  /30

  $179,900

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

  24 Southern Ave, Pittsfield, MA 01201

  Two-family flat offering strong potential for investors or owner-occupants seeking rental income. Located close to town, this property features a 3-bedroom, 1 bath first-floor unit with a de-lead certificate that will soon be vacant and a 2-bedroom 1-bath second-floor unit that has been de-leaded but has no certificate and is currently on a month-to-month lease. An enclosed front porch adds charm

  Cindy Carrigan LAMACCHIA REALTY, INC

  24 Southern Ave, Pittsfield, MA 01201
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  /75

  $3,250,000

  • 6 Beds
  • 5.5 Baths
  • 3,416 Sq Ft

  651 Hayes Hill Rd, New Marlborough, MA 01230

  Built in 1964, this Berkshires compound comprised of three homes set on over fifty acres with panoramic southerly views to the northern Connecticut hills. The main home, a modernist design collaboration between Bauhaus designer George Giusti and architect Crane De Camp, is a two-bedroom, three-and-a-half-bath masterpiece that features a gym, sauna, and gardens designed by a local landscape

  Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

  651 Hayes Hill Rd, New Marlborough, MA 01230
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  /5

  $399,000

  • 8 Beds
  • 4 Baths
  • 3,536 Sq Ft

  144 Madison Ave Unit 4, Pittsfield, MA 01201

  Centrally located four-unit investment property on large corner lot with plenty of off-street private parking. New natural gas hot water boiler. Property is welll maintained with long term tenants and recent renovations. Large basement with separate electric. Conveniently located near restaurants, retail, medical facilities and key city amenities, a good location that supports strong tenant

  Lisa Kelley MACCARO REAL ESTATE

  144 Madison Ave Unit 4, Pittsfield, MA 01201
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  /38

  $305,000

  • 7 Beds
  • 3 Baths
  • 3,264 Sq Ft

  139 Robbins Ave, Pittsfield, MA 01201

  Expansive duplex offering a three bedroom unit and a four bedroom unit. Recently remodeled with updated kitchens, bathrooms, flooring, and paint throughout. One unit enters into a open and bright living room off the kitchen with a first floor bedroom and full bathroom with laundry. Second floor includes another full bathroom and three large bedrooms. The second unit which has also been updated

  Cory Evangelisto NOCHER REALTY

  139 Robbins Ave, Pittsfield, MA 01201
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  /15

  $80,000

  • 8 Beds
  • 8 Baths
  • 1,584 Sq Ft

  71 Center St, Pittsfield, MA 01201

  This property is a blank canvas ready for your vision. Previously operated as an 8-unit building consisting of studio and one-bedroom apartments, it is currently registered with the city as a two-family property. Any future changes or redevelopment will require approval through the local building department.With the right improvements, this property offers excellent potential for a strong

  Michele Purcell LAMACCHIA REALTY, INC

  71 Center St, Pittsfield, MA 01201
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  /65

  $2,495,000

  • 5 Beds
  • 4.5 Baths
  • 3,615 Sq Ft

  17 Cronk Rd, Great Barrington, MA 01230

  Originally built in the 1700s, this historic post-and-beam barn has been thoughtfully renovated over time while maintaining its unique character and charm. A recently installed solar energy system allows for highly efficient living with the potential for an off-grid lifestyle.The home features an open floor plan filled with natural light from numerous oversized windows. A chef's kitchen adjoins

  Suzann Ward HOUSATONIC REAL ESTATE

  17 Cronk Rd, Great Barrington, MA 01230
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  /57

  $1,895,000

  • 6 Beds
  • 4.5 Baths
  • 4,139 Sq Ft

  176 W Center Rd, West Stockbridge, MA 01266

  A lovely, winding approach to this gorgeous 21-acre estate ensuring serenity, privacy, and the beauty of living in the country. The main house includes 3-4 bed, 2 1/2 bath. An impressive architect-designed guest house has 2 ensuite bedrooms with balconies, dramatic exposed beams and vaulted ceilings. The guest house is an extraordinary place to host family and friends both winter and summer. With

  Randy Thunfors STONE HOUSE PROPERTIES, LLC

  176 W Center Rd, West Stockbridge, MA 01266
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  /23

  $3,400,000

  • 14 Beds
  • 16.5 Baths
  • 11,945 Sq Ft

  615 Laurel St, Lee, MA 01238

  An exceptional opportunity awaits at 615 Laurel Street, Lee, MA, presenting a property of enduring character with 530 feet of lakefront. The expansive interior environment encompasses fourteen dedicated bedrooms, each offering an individual sanctuary for rest and rejuvenation. Complementing these private quarters are sixteen full bathrooms, providing unparalleled comfort and convenience

  Mitchell B Muroff Mitchell B. Muroff

  615 Laurel St, Lee, MA 01238
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  /22

  $350,000

  • 5 Beds
  • 5 Baths
  • 3,216 Sq Ft

  138 Church St, North Adams, MA 01247

  Investors take notice! Rare opportunity to own a fully occupied 5-unit multifamily offering immediate cash flow, just minutes from downtown North Adams and Mass MoCA, plus local shops, dining, and attractions. Property features five spacious units, including a recently renovated 1-bedroom unit above the detached garage providing additional rental income. Off-street parking and a recently replaced

  Dante Cellana BURNHAM GOLD REAL ESTATE, LLC

  138 Church St, North Adams, MA 01247
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  /32

  $249,900

  • 6 Beds
  • 2 Baths
  • 2,700 Sq Ft

  73-75 Hall St, North Adams, MA 01247

  Two-family flat with one unit renovated and the other unit ready to be completed. Each apartment consists of living room, dining room, kitchen 3 bedrooms and 1 bathroom. There is a lovely front porch offering gorgeous mountain views!The third floor is the attic, separate from the apartments, offering ample storage space. This is where the furnace for 2nd floor unit is located.The home has city

  Maria Liccardi KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  73-75 Hall St, North Adams, MA 01247
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  /6

  $70,000

  • 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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  /94

  $2,390,000

  • 6 Beds
  • 4.5 Baths
  • 7,894 Sq Ft

  500 Williams St, Pittsfield, MA 01201

  Own a Living Masterpiece. Meticulously curated by the current stewards since 2006. This Colonial Revival offers rare fusion of 18th-century authenticity and cutting-edge modern comfort. Designed for both grand-scale entertaining and intimate family life, this c1930, 7,894 sq. ft., Colonial Revival offers 6-bdrms & 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  500 Williams St, Pittsfield, MA 01201
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  /22

  $850,000

  • 25 Beds
  • 12 Baths
  • 18,402 Sq Ft

  40 Pecks Rd, Pittsfield, MA 01201

  Don’t be late for this redevelopment opportunity! 18,000 Sqft on 1.1 Acres. Structurally sound property offers a rare opportunity to transform a historic space into a vibrant new community. Preliminary estimates suggest the potential for 12 residential units, with ample room for parking and green space. Featuring solid brick construction. Expansive windows, high ceilings, and open floor plans,

  Xavier Cruz Fathom Realty

  40 Pecks Rd, Pittsfield, MA 01201
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  /65

  $895,000

  • 5 Beds
  • 3 Baths
  • 4,802 Sq Ft

  581 Red Barn Rd, Dalton, MA 01226

  Immaculate 4800 square foot, 5BR, 4 full bath jewel located at arguably the finest condominium community in The Berkshires. Enjoy looking at spectacular foliage with private panoramic wooded views and open space from the magnificent all seasons room, great room and primary suite. The garden level features a full kitchen as well as a screened in porch. The Buterus furnace system powers baseboard

  Buddy Lewis BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  581 Red Barn Rd, Dalton, MA 01226
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  /92

  $1,050,000

  • 6 Beds
  • 4.5 Baths
  • 5,219 Sq Ft

  127 Pinecrest Dr, Dalton, MA 01226

  A Stunning Three-Story Residence with Breathtaking Views for an Easy Care Lifestyle in the Berkshires.Majestic and magical perfectly describe this exquisite three-story mountain top home, designed to capture the stunning and distant views of the Berkshire skyline. With over 5,000 square feet of expansive living space, this centrally located residence offers the perfect opportunity to either

  Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

  127 Pinecrest Dr, Dalton, MA 01226
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  /3

  $419,000

  • 7 Beds
  • 4.5 Baths
  • 4,682 Sq Ft

  312 South St, Pittsfield, MA 01201

  Four-family investment opportunity that checks all the boxes! Great location. Fully rented. Turnkey. Robust net operating income. This well-maintained home, comprising three 2-bedroom units and one 1-bedroom unit all with separate utilities, is an instant profit generator and offers real value in today's market.

  Derek Greene The Greene Realty Group

  312 South St, Pittsfield, MA 01201
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  /85

  $1,399,000

  • 7 Beds
  • 4.5 Baths
  • 5,104 Sq Ft

  295 Blair Rd, Williamstown, MA 01267

  Own a piece of Williamstown history with this beautifully preserved Greek Revival modern farmhouse, set along the Green River on just under 20 picturesque acres. This exceptional property offers a rare combination of historic charm and modern comfort, with ample acreage for farming or livestock, ponds, barns, an in-ground pool, and more. The main residence features 5 bedrooms and 4 bathrooms,

  Erin Scott BURNHAM GOLD REAL ESTATE, LLC

  295 Blair Rd, Williamstown, MA 01267
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  /40

  $4,900,000

  • 8 Beds
  • 6.5 Baths
  • 7,494 Sq Ft

  140 Hancock Rd, Pittsfield, MA 01201

  Welcome to an extraordinary lakefront estate on the shores of Pontoosuc Lake, an offering that sets a new benchmark for luxury living in the Berkshires. With over 7,494 square feet of total space, including exceptional garage capacity ideal for car collectors or hobbyists, this remarkable property offers unparalleled scale, versatility, and setting.The main living area showcases a thoughtfully

  Elisha Poirier STONE HOUSE PROPERTIES, LLC

  140 Hancock Rd, Pittsfield, MA 01201
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  /58

  $2,595,000

  • 5 Beds
  • 4.5 Baths
  • 4,305 Sq Ft

  95 Lewis Ave, Great Barrington, MA 01230

  This exquisite single-family home spans an impressive 4,300 square feet, offering an unmatched blend of elegance and modern comfort. With 5 spacious bedrooms and 4.5 beautifully renovated bathrooms, every detail has been meticulously crafted to perfection. Walking distance to downtown Great Barrington's shops and restaurants, the house is in one of the quietest areas of ''The Hill''.12 rooms

  Martin Albert COMPASS MASSACHUSETTS , LLC GB

  95 Lewis Ave, Great Barrington, MA 01230
• 

  

  /48

  $974,999

  • 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 WILLIAM PITT SOTHEBY'S - LENOX

  560 Stockbridge Rd, Lee, MA 01238

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