An exceptional side-by-side duplex in Pittsfield's desirable Southeast neighborhood, offering two spacious 3-bedroom, 1-bath residences and an ideal combination of comfortable living and income potential. Both units feature bright, inviting interiors, granite countertops, updated finishes, and well-designed living spaces that feel more like individual homes than traditional apartments. The side-by-side configuration provides privacy and separation, making this an outstanding option for an owner-occupant looking to offset housing expenses or an investor seeking a quality addition to their portfolio. A partially fenced backyard offers flexibility for separate outdoor spaces, while one unit includes access to the garage/outbuilding for additional storage and utility.

Opportunity awaits in this spacious 4-bedroom, 3-bath Colonial located in the highly sought-after Orchard neighborhood. Offering generous room sizes throughout, this home features a welcoming family room with a fireplace and skylights that fill the space with natural light. The convenient first-floor laundry enhances everyday living. The partially finished basement provides additional flexible space for recreation, a home office, or storage. Recent updates include newer carpeting and a newer roof, offering a solid foundation for future improvements. Outside, enjoy a fenced backyard with a deck. While the home could benefit from some TLC and cosmetic updates, it presents an excellent opportunity to build equity and customize to your taste in a prime location.

Historic character meets modern updates in this beautifully renovated 1880s home! Thoughtfully updated while preserving its original charm and integrity, the home underwent an extensive renovation in 2016, including new electrical, plumbing, insulation, and much more. Beautiful wood floors flow throughout, adding warmth and character. The first floor offers flexible living with a bedroom or home office and a full bathroom. Upstairs, you'll find three additional bedrooms, another full bath, and the convenience of second-floor laundry. There is also potential to expand the primary suite with space for an additional bathroom that has already been roughed in.

To Be Built, energy-efficient, low-maintenance 1,375 sq ft gable entry ranch with 3 bedrooms and 2 full baths. This home offers true single-level living with an open-concept layout connecting the kitchen, dining, and living areas, ideal for everyday living and entertaining. The primary suite includes a private full bath, while two additional bedrooms offer flexibility for guests or a home office. A 10' x 10' pressure-treated deck is perfect for relaxing or entertaining. Photos, pricing, and layouts are for display only and may include upgrades. Final specs subject to change. Buyers may select colors and most finishes. Standard finishes included in pricing.

Welcome home to this renovated 1910 Tudor-style Ranch ideally located in a premier neighborhood. This charming home offers the perfect blend of timeless character and easy modern living. Original architectural details, beautiful woodwork, and period charm have been thoughtfully preserved while the home has been updated for today's lifestyle. Featuring 3 bedrooms, 2 baths, and a detached 2-car garage, the inviting floor plan is comfortable, functional, and move-in ready. A truly special home that delivers the character buyers love with the convenience they're looking for.

This 3-bedroom, 1-bath Raised Ranch is sited in a peaceful country setting with convenient nearby access to Pontoosuc Lake. With nearly one full acre of land, the property offers ample space, privacy and potential for expansion. An exceptional heated detached two-car garage/workshop features finished bonus space above, ideal for an artist studio or a dreamy private home office. Inside, the main house you'll find a practical layout, hardwood floors, updated kitchen appliances and a renovated full bathroom. The lower level is ready for your updates, presenting an excellent opportunity to make this space your own. This is the perfect opportunity to enjoy the tranquility of the surrounding setting while remaining conveniently located near outdoor recreation, shopping and dining.

This charming 3-bedroom home is ready to move in! Great west Pittsfield neighborhood. Just 5 minutes from downtown, less than 20 to Tanglewood, a half hour drive to Williams College and the Clark Art Institute. Wood burning fireplace, lots of natural light, heated sun porch, and a beautiful backyard with a large deck, berry bushes, and fruit trees. The first floor features the kitchen with stainless steel appliances, dining area, living room, and sun room. The sun porch off the garage is heated and is not included in the square footage of the house. The second floor features 3 bedrooms, beautiful wood floors, and a full bath with jetted tub. The basement houses the laundry and a half bath, with lots of room for storage. Most windows in the house are just a few years old.

Built by Thomas Colt in 1865, 42 Wendell Avenue is a striking Italian Villa style property with a rich place in Pittsfield's history. Once owned by Simon England Sr., who deeded it in memory of his wife, the building later became the Women's Club of Pittsfield and most recently served as the Whitney Center for the Arts. The arched entrance opens to more than 7,700 square feet across 15 rooms. Soaring ceilings, inlaid hardwood floors, ornate fireplaces, carved wood mantels, and substantial original woodwork lend character throughout. Tall windows bring natural light into the rooms, and a sunroom offers a bright space overlooking the grounds. The property's scale and layout invite a range of possibilities. Rooms on both floors could accommodate professional offices or studios, while the

Built by Thomas Colt in 1865, 42 Wendell Avenue is a striking Italian Villa style property with a rich place in Pittsfield's history. Once owned by Simon England Sr., who deeded it in memory of his wife, the building later became the Women's Club of Pittsfield and most recently served as the Whitney Center for the Arts. The arched entrance opens to more than 7,700 square feet across 15 rooms. Soaring ceilings, inlaid hardwood floors, ornate fireplaces, carved wood mantels, and substantial original woodwork lend character throughout. Tall windows bring natural light into the rooms, and a sunroom offers a bright space overlooking the grounds. The property's scale and layout invite a range of possibilities. Rooms on both floors could accommodate professional offices or studios, while the

To Be Built, energy-efficient, low-maintenance 1,340 sq ft gable entry ranch with 3 bedrooms and 2 full baths. This home features an open-concept layout connecting the kitchen, dining, and living areas, ideal for everyday living and entertaining. A split-entry design leads to a one-car garage underneath, offering convenience and additional storage. The primary suite includes a private full bath, while two additional bedrooms provide flexibility for guests or a home office. Enjoy a 10' x 10' pressure-treated deck, perfect for relaxing or entertaining. Photos, pricing, and layouts are for display only and may include upgrades. Final specs subject to change. Buyers may select colors and most finishes. Standard finishes included in pricing.

To Be Built, energy-efficient, low-maintenance 1,340 sq ft gable entry ranch with 3 bedrooms and 2 full baths. This home features an open-concept layout connecting the kitchen, dining, and living areas, ideal for everyday living and entertaining. A split-entry design leads to a one-car garage underneath, offering convenience and additional storage. The primary suite includes a private full bath, while two additional bedrooms provide flexibility for guests or a home office. Enjoy a 10' x 10' pressure-treated deck, perfect for relaxing or entertaining. Photos, pricing, and layouts are for display only and may include upgrades. Final specs subject to change. Buyers may select colors and most finishes. Standard finishes included in pricing.

To Be Built, energy-efficient, low-maintenance 1,340 sq ft gable entry ranch with 3 bedrooms and 2 full baths. This home features an open-concept layout connecting the kitchen, dining, and living areas, ideal for everyday living and entertaining. A split-entry design leads to a one-car garage underneath, offering convenience and additional storage. The primary suite includes a private full bath, while two additional bedrooms provide flexibility for guests or a home office. Enjoy a 10' x 10' pressure-treated deck, perfect for relaxing or entertaining. Photos, pricing, and layouts are for display only and may include upgrades. Final specs subject to change. Buyers may select colors and most finishes. Standard finishes included in pricing.

Seller is motivated for a new owner to fall in love with this beautifully maintained two-story brick colonial home. Nestled in one of the area's most sought after neighborhoods, this well-loved residence is filled with charm and character. The classic red brick exterior is settled on its lot with timeless curb appeal providing an irresistible first impression. Built in 1920, this home is listed with the Massachusetts Historical Comm. as a historic property. It showcases the craftsmanship of an early era preserved with its timeless classic architecture together with the upgrades needed to keep trending with modern conveniences. Enter into the front-door foyer and find the original charm of original oak floors throughout.

UNIQUE OPPORTUNITY TO HAVE A SPACIOUS FAMILY HOME WITH HIGH VISIBILITY FOR A HOME OFFICE OR BUSINESS. THOUSANDS OF VEHICLES WILL SEE YOUR BUSINESS SIGN AND YOUR OFFICE WILL HAVE A PRIVATE ENTRANCE. PERFECT FOR SOMEONE IN THE TRADES, IE; CONTRACTOR, PLUMBER, ELECTRICIAN AND ALSO PROVIDING A LARGE FAMILY LIVING SPACE WITH A PRIVATE BACK YARD. COME SEE FOR YOURSELF.

Charm meets city convenience in this one-of-a-kind duplex exuding character at every turn. This classic side-by-side boasts fronts on two different streets, with original 1910 details that create a timeless living space. Investors: this moneymaker won't last long. Prospective homeowners: live on one side, rent the other - steady income and easy management! You'll find hardwood floors, oversized bedrooms, and spacious living areas, with quirky nooks and crannies and beautiful craftsmanship. Large windows bathe the interior in light. Its outdoor spaces are perfect for relaxation or entertaining. Features an oversized two-car garage/storage. Take advantage of the opportunity to own this feature-filled home just half a mile from Downtown! Property sold as is.

Welcome to this beautiful and inviting home in Pittsfield's most sought-after Southeast neighborhood. This is a unique opportunity to live at Wellesley Park, a small city-owned and beautifully maintained park, where homes rarely come on the market because once you live in this community, you will never move again! This well maintained, light-filled 2,100 square foot home boasts a large formal living room with over-sized picture windows at each end and fireplace; a very large kitchen with five-burner cooktop and double wall ovens; an office, half bath; dining room; and den making up the downstairs.

Space, comfort, and flexibility awaits in this beautifully renovated home, built in 1988 and designed with room for everyone. The main level features a tastefully renovated kitchen, a large living room with French doors opening to a wonderful deck overlooking the mountains, plus a convenient half bath and laundry. Upstairs, you'll find 4 spacious bedrooms with generous closets, including a primary suite with its own private bath. The lower level offers even more living space, including a bonus room ideal for an office or additional bedroom, a full bath, and a second deck--perfect for creating your own hot tub retreat. A small backyard means less maintenance, while the two-car garage adds convenience. The 2022 mini-split and solar panels installed in September 2024 enhance efficiency.

Prime investment opportunity in a highly desirable location just steps from the post office and within walking distance to downtown amenities, shopping, dining, and services. This well-maintained four-family property offers strong income potential with all separate utilities, allowing tenants to pay their own expenses and helping to maximize owner returns. Recent capital improvements include a new roof installed in 2022 and two high-efficiency gas furnaces added in 2023, providing peace of mind for years to come. Each unit features washer and dryer hookups, while newer hot water boilers, vinyl replacement windows, and low-maintenance vinyl siding contribute to reduced operating costs and enhanced efficiency. Tenants will appreciate the private paved parking area and detached two-car

Welcome to this immaculately maintained two-family home --a turnkey property that meets today's timeless standards! This choice 2-family home beautifully balances sophisticated living with incredible versatility, making it an ideal match for owner-occupants, multigenerational families, or savvy investors alike. Including features you are sure to love: Modern Living: Bright, open-floor-plan living areas featuring fresh paint and updated appliances. Comfort & Convenience: Both units boast primary bedrooms with en suite baths, large dedicated laundry areas, updated windows, and pristine ceramic-tile bathrooms. Flex Space: A partially finished basement offers the perfect canvas for storage, workshop, craft area, home gym, etc.

Yes, the Jim's House of Shoes building is for sale! Great location in the heart of North St, downtown Pittsfield. 4 large front display windows, 3 entrances and exits, full, usable 5,500 sq. ft. basement with inside access. Start a business here; move a business here; be part of Pittsfield's rejuvenation!