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36 Photos
413 REAL ESTATE
$229,900
3 BD | 2 BA
Multi-Family

Charming 2-Family Flat - Great Investment or Owner-Occupied Opportunity!Don't miss this 2-family flat offering classic charm and modern convenience. Each spacious unit features hardwood floors The second-floor unit boasts an enclosed porch--perfect for relaxing or additional living space. Separate utilities, off street parking and shed add to the property. This property has potential to be used as single family. This property offers flexibility, functionality, and value. Schedule your showing today!


29 Photos
WILLIAM PITT SOTHEBY'S - LENOX

Dottie's Coffee Lounge, a beloved staple in the heart of Berkshire County, is now presenting a rare opportunity for new ownership. Renowned for its commitment to sustainability and locally sourced offerings, this legendary establishment has served as a community hub for food enthusiasts, coffee connoisseurs, and art and music lovers alike. This ethos has cultivated a loyal customer base and contributed to a sustainable community that values the connection between local produce, culinary excellence, and culture. This is more than a business transaction; it's a chance to carry on a legacy integral to Berkshire County's fabric. *Sale is for the business & fixtures only-does not include real estate.


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WILLIAM PITT SOTHEBY'S - LENOX

Dottie's Coffee Lounge, a beloved staple in the heart of Berkshire County, is now presenting a rare opportunity for new ownership. Renowned for its commitment to sustainability and locally sourced offerings, this legendary establishment has served as a community hub for food enthusiasts, coffee connoisseurs, and art and music lovers alike. This ethos has cultivated a loyal customer base and contributed to a sustainable community that values the connection between local produce, culinary excellence, and culture. This is more than a business transaction; it's a chance to carry on a legacy integral to Berkshire County's fabric. *Sale is for the business & fixtures only-does not include real estate.


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WILLIAM PITT SOTHEBY'S - LENOX

Welcome to 306 Wahconah Street -- a high-visibility, high-traffic location ideal for your next business venture. Previously operating as a successful fast-food establishment and bank, this freestanding commercial building offers versatile potential for restaurant, retail, or service-based use. Located just minutes from downtown Pittsfield and close to major routes, the property benefits from strong local traffic and excellent street frontage.Featuring a grandfathered drive-thru infrastructure, ample parking, and a flexible interior layout, this is a rare opportunity to establish your business in a well-known and accessible location.Don't miss your chance to reimagine this Pittsfield property.


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BISHOP WEST REAL ESTATE
$235,000
3 BD | 2 BA
Multi-Family

Welcome to 15 High Street in Pittsfield -- a well-located two-family flat offering versatility, investment potential, & everyday convenience. Situated within walking distance to local schools, banking, restaurants, & shops, this property makes it easy to enjoy all that city living has to offer.Each unit provides comfortable living space with functional layouts, making it ideal for owner-occupants looking to offset their mortgage or investors seeking solid rental income. The property offers separate living areas, ample natural light, & the charm of a classic multi-family home.Whether you're expanding your portfolio or searching for a smart owner-occupied opportunity, this centrally located two-family is a fantastic option close to downtown amenities, public & transportation.


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RE/MAX TRANSITIONS
$235,000
6 BD | 4 BA
Multi-Family

Unique duplex with a 2 stall garage, 3 bedrooms and 2 full baths in both units. All separate utilities with one unit equipped with solar panels for greatly reduced electric costs. New boilers and water heater. Owner occupied one side and multi year tenant on the other.


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OCTOBER MOUNTAIN REAL ESTATE
$235,900
2 BD | 2 BA
Residential - Condo/Townhouse

Coveted end unit with vaulted ceiling, deck and western views to private pool and hills beyond. Two full baths, garage, high quality window treatments, light fixtures and ceiling fan. Dramatic stone fireplace with Pellet stove. Flower garden. Very desirable unit in a safe, quiet, beautifully maintained association!


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NOCHER REALTY
$245,000
4 BD | 2 BA
Multi-Family

Two family duplex just outside of downtown. Featuring two bedrooms and one bathroom in each unit with hardwood floors. Off Street parking and separate utilities.


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KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$249,900
3 BD | 1 BA
Residential - Single Family

Location and privacy! Amazing opportunity to own a home on 0.46 acres plus two additional lots with 0.46 and 0.17 acres each, totaling about 1.1 acres, in a private area, on a dead end street! The house is a fixer upper, the exterior is freshly painted, the interior needs renovation but all utilities and mechanicals are on. The first floor features a lovely enclosed front porch, dining room, living room and kitchen; and the 2nd floor offers 3 bedrooms and full bath. There are hardwood floors throughout! There is also a walk-up attic for great storage space. The basement has concrete floor, 100 amp electrical service, and a new boiler was installed in 2024. City water and sewer. Two attached garages complete this great property!


47 Photos
LAMACCHIA REALTY, INC
$249,900
3 BD | 1 BA
Residential - Single Family

Welcome to 18 Meadow Lane, a charming colonial-style home nestled in the heart of Pittsfield, MA. This delightful residence features three spacious bedrooms and a well-appointed bathroom, perfect for families or those seeking extra space. The home showcases beautiful natural woodwork throughout, adding character and warmth to each room. The detached one-car garage offers convenience and additional storage. Enjoy the benefits of a centrally located property, with easy access to local amenities, schools, and parks. Whether you're entertaining guests or enjoying quiet evenings, this home provides the ideal setting for comfortable living. Don't miss the opportunity to make this lovely house your new home!


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LAMACCHIA REALTY, INC
$250,000
4 BD | 1 BA
Residential - Single Family

Welcome to 9 Lincoln Street, featuring white interior, hardwood floors throughout, large sun-filled rooms, and an open, flowing layout. The main level features a spacious living room, a bonus room that could serve as a first-floor bedroom, a dining room, and kitchen with direct access to a fully fenced backyard. Double doors open to an outdoor space ideal for relaxing or entertaining. Upstairs are three well-proportioned bedrooms, including a primary bedroom with a private sun porch. Another bedroom has a private sun-filled office attached. A full bathroom with a bathtub serves the second floor. The home also includes a basement and attic for ample storage, along with a brand-new roof. Conveniently located downtown Pittsfield, near shopping, dining, and Berkshire Medical Center.


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BISHOP WEST REAL ESTATE

Experience refined country living on this immaculate 8.93-acre estate parcel, fully cleared and impeccably prepared with a private well, installed 4 bedroom septic system, underground electric tied in, and a 1,000-gallon underground propane tank. A proposed septic easement accommodates an abutting lot. The HOA provides driveway and common-land maintenance, with restrictions and covenants ensuring lasting elegance: minimum 2,000 sq ft residences, two-car garages, and timeless neutral exteriors. An exclusive, estate-like setting for an exceptional custom home awaits. Additional Lots Available!!!


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KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$259,000
3 BD | 1 BA
Residential - Single Family

Move-in ready cape-style home located in southeast Pittsfield. Offering 3 bedrooms and 1 full bath, this is the perfect starter home or ideal for those looking to downsize without sacrificing comfort or quality.Updates include a newer roof and electrical panel (2014) and a high-efficiency combo boiler installed in 2025. Conveniently located close to local amenities, schools, and parks, this home combines classic cape charm with modern improvements.


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NOCHER REALTY
$259,900
6 BD | 3 BA
Multi-Family

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 separate kitchens and bathrooms but originally was a three bedroom apartment. Each unit has its own heating, hot water, and electrical systems.


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KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$264,900
4 BD | 2 BA
Multi-Family

This fully rented two-family home was renovated in the last two years! Improvements include roof, windows, flooring, painting, and more! The home offers an enclosed front porch to access both units, and a side porch for each apartment independently. Each unit features living room, dining room, kitchen, 2 bedrooms and 1 bath. There is separate heat, hot water and electric: Unit 52 has natural gas heat while unit 50 has electric heat and hot water. There is a large backyard abutting the river!This is a convenient location, just a couple houses down from Durant Park, which has picnic tables, gazebo and playground; and a few minutes from downtown!


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BIRCH PROPERTIES
$265,000
4 BD | 2 BA
Residential - Single Family

Spacious and freshly updated West Side single-family offering 4 bedrooms and 2 full baths across 1,408 sq ft. Bright, functional layout with generous room sizes, fresh interior paint, and new laminate flooring throughout. Modern kitchen features brand-new appliances and clean, updated finishes. Enjoy a charming wraparound porch with dual entry, ideal for relaxing or entertaining, plus a level backyard on a 6,969 sq ft lot. Efficient gas steam heat. Move-in ready and thoughtfully improved for comfortable everyday living.


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LAMACCHIA REALTY, INC
$269,900
3 BD | 1 BA
Residential - Single Family

Welcome to 41 Jayne Ave, a charming 3-bedroom, 1-bath ranch nestled in the desirable southwest area of Pittsfield, MA. This inviting home features a spacious living room that flows into a bright kitchen, ideal for family gatherings and entertaining. Enjoy the convenience of single-level living with three comfortable bedrooms, perfect for restful nights. The private backyard offers ample space for outdoor activities and gardening, making it a serene retreat. Located in a quiet neighborhood, this property is close to parks, schools, and local amenities, providing both tranquility and accessibility. Don't miss the opportunity to make this lovely ranch your new home!


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WILLIAM PITT SOTHEBY'S - LENOX
$277,500
2 BD | 2 BA
Residential - Condo/Townhouse

Enjoy the ease of single level living in this beautifully updated end unit, ranch style condominium, ideally situated in one of the most desirable locations within the complex. This light filled corner home offers an open concept living room, dining area, and kitchen featuring stainless appliances and thoughtful updates designed for effortless everyday living and entertaining. The inviting living room is anchored by a fireplace and opens to a private deck through sliding glass doors, creating warmth and seamless indoor outdoor flow with sweet exterior natural views.


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BISHOP WEST REAL ESTATE
$279,900
4 BD | 2 BA
Residential - Single Family

Conveniently located home offering more space than expected, with 4 bedrooms and 1.5 bathrooms. The main level features a bright living room, dining area, and kitchen, along with a full bath and bedroom or office option. Upstairs includes 3 additional bedrooms with great natural light. Mini split systems provide efficient heating and cooling, and solar helps offset electric costs. The lower level offers usable storage and additional finished space potential. Outside, enjoy a partially fenced yard, storage shed, and covered parking. Convenient Pittsfield location close to downtown, shopping, and local amenities. Easy opportunity to move in and make it your own!


32 Photos
KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.
$279,900
4 BD | 2 BA
Multi-Family

Renovated two-family home! The first floor unit is vacant and ready for immediate occupancy while the second floor unit is rented on a year lease at $1,550/month with the tenant paying for his own natural gas heat, hot water, and electric since these utilities are separate for each unit.The apartments have been tastefully renovated, they're freshly painted, each offering 2 bedrooms, full bath, living room, laundry hookups, and kitchen with new cabinets, quartz countertops and stainless steel appliances.The home has new gutters installed in 2025, new electrical panels and a newer roof. Lead compliance certificates will be provided! This is a great opportunity for owner occupants as well as investors. A great multifamily with proximity to the downtown Pittsfield attractions!

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