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 under review with the Massachusetts Historical Committee to be designated 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.

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

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!

Welcome to this charming 4-bedroom, 2-bath home offering the perfect blend of comfort, updates, and extra living space. The updated kitchen and renovated first-floor bath provide modern style and convenience, while the finished lower level adds versatile space for a family room, home office, gym, or guest area. A bright and inviting sunroom fills the home with natural light and offers the perfect place to relax year-round. Outside, enjoy a spacious fenced backyard ideal for entertaining, pets, or play, along with an oversized garage providing ample storage and workspace. As an added bonus, the property includes deeded lake rights with private access to Onota Lake, giving you access to enjoy nearby water activities and scenic surroundings.

Immaculate, adorable, expansive, well maintained 2500 sq ft ranch. 4 bedrooms 3 bathrooms, open living room & dining area with fireplace. Bright eat in kitchen, a sunny 3 season porch with a newer deck. This home sits on a 1/2-acre lot in a quiet tucked away neighborhood. There's a full walkout lower level with family room, fireplace, bar, full bathroom & dining area which leads to a back patio nice, open back yard area. Home has lots of storage. New chimney, garage door, side deck are just some of the upgrades. Close to shopping, downtown, theaters, Lake Onota and schools.

Welcome to 30 Lexington Parkway, an exceptionally cherished home in one of Southeast Pittsfield's most coveted neighborhoods. Brimming with timeless character, warmth, and pride of ownership, this impeccably maintained 4-bedroom home blends classic charm with everyday comfort. The inviting living spaces feature a stunning fireplace, hardwood floors, spacious eat-in kitchen, screened-in porch surrounded by the meticulously cared-for private backyard. A finished basement offers room to grow, while flexible spaces adapt effortlessly as a home office, library, studio or gym. Complete with a 2-car garage and conveniently located near parks, recreation, schools, dining, shopping, downtown, and the Berkshires renowned arts and cultural attractions. Come home to a place where memories are made!

Beautifully maintained 4-bedroom, 2.5-bath Colonial set on a quarter acre lot with privacy and curb appeal. Enjoy a spacious floor plan featurning a wood-burning fireplace, natural gas heat & hot water and newer replacement windows throughout, including new living room windows in 6/2026. The primary suite offers his-and-hers closets and a private bath. The finished lower level adds valuable living space with a family room, bar area, surround sound and separate storage room with built-in cabinets. Relax outdoors on the deck with a new awning (2026), framed by an arbor & private setting. Additional highlights include metered water, an attached 2-car garage with auto openers and rear storage room. Move-in ready and ideal for everyday living and entertaining!

Introducing 444 Pomeroy Ave, a true neighborhood icon! This one ticks all the boxes: Curb appeal to the max with mature perennial plantings, gracious front yard, private side yard with hot tub, and the true star of the show--the screened porch, which you won't want to leave in the summer. The home is spacious with a cooks kitchen and dining room, ample fire placed living room w/ built-ins galore. First floor 1/2 bath, & period details & charm that cannot be replicated today. Upstairs, 3 sizable bedrooms, & a fully renovated bathroom w/ Italian marble counters, tiled walk-in shower & radiant heat. The partially finished lower level features another bedroom for extended family and guests. A large two car garage was added, with exceptional loft storage space above. Be ready to fall in love!

Turnkey office and flex building with detached four-bay garage available for sale or lease in Pittsfield, Massachusetts. 326 Springside Avenue offers 2,367 SF of finished first-floor office/flex space plus a full lower level, located on a corner parcel at Springside Avenue and Westminster Street. The property includes a detached ±960 SF four-bay garage, 10 surface parking spaces, a new roof, and a standby generator. B-G zoning provides flexible use potential. Ideal for an owner-user, professional office, contractor, or light flex operation seeking office, storage, and garage space on one site. Available immediately. For full details, floor plans, 42 high-resolution photos, and Matterport 3D tours of both levels, visit: https://326springsideavenue.com

Set within one of Southeast Pittsfield's most desirable neighborhood settings, 53 Greenings offers an exceptional blend of privacy, space, and effortless everyday living. Set on a beautifully landscaped 1.07-acre double lot, this spacious ranch style residence feels wonderfully secluded while remaining connected to the conveniences and amenities of the surrounding community. Mature landscaping, established flower beds, and expansive lawn create a truly park-like setting, an inviting backdrop for morning coffee, summer gatherings, or simply enjoying the quiet of home.

Beautiful combination of modern renovations with historic character! The first floor boasts an easy living circular flow with kitchen, dining and living room with stunning floors and washed with fabulous natural light. Family room tucked away for a more intimate space, large laundry room, mudroom and half bath. The second level includes a primary bedroom with an updated en suite full bath and walk in closet, two guest bedrooms, art deco full bath and additional flex space over the garage. Gracious front porch that overlooks ample level lawn on over a half of an acre, including both an attached and detached garage. Located in a convenient location on the Southeast side of Pittsfield. Major updates include, roof, kitchen, bathrooms, electrical, heating, plumbing, central AC and more

Welcome to easy single floor living in a highly desirable Southeast Pittsfield neighborhood! Built in 2003, this exceptionally well-maintained contemporary home features 3 spacious bedrooms, 2 full baths, soaring vaulted ceilings, and beautiful hardwood floors. The light-filled primary suite includes a private ensuite bath, while the enclosed 3-season room and front porch offer ideal spots to relax overlooking a low-maintenance yard. Complete with a newer roof, central air, a massive unfinished basement with endless potential, and city-maintained street access, this move-in-ready property is a standout Berkshire home!

Embrace the beauty of the Berkshires from this thoughtfully updated home, ideally situated on a sought-after street across from Onota Lake. Large windows fill the home with an abundance of natural light, highlighting the warmth and classic character found throughout. The many improvements include an updated kitchen, gorgeous wood flooring that creates an inviting connection to the spacious living room. A fireplace surrounded by contemporary built-in shelving brings a welcoming space boasting seasonal views of the backyard. The dining room with its original built-in cabinetry adds a cozy space for gathering. The newly finished basement offers nearly 1,000 square feet of bonus space with another fireplace, perfect for entertaining, work and/or play space or whatever your heart desires.

Meticulously maintained and lovingly cared for, this spacious four-bedroom, two-and-a-half-bath home offers the perfect combination of comfort, quality, and location. Featuring generously sized rooms throughout, this home provides ample space for both everyday living and entertaining. Pristine wood floors lie beneath the carpeting, offering the opportunity to uncover their timeless beauty. Recent improvements, including a new roof, providing peace of mind, while gas heat and central air conditioning ensure year-round comfort. Set in one of the area's most desirable neighborhoods and within a highly sought after school district, this property offers a truly special connection to its surroundings.

Discover a prime investment opportunity at 110-118 Lincoln Street in Pittsfield! This well-maintained property features four spacious units, each offering three bedrooms and one bath--perfect for attracting reliable tenants. With separate utilities for each unit, managing expenses is seamless. Ample off-street parking ensures convenience for all residents, enhancing the living experience. Ideal for investors or those looking to enter the rental market, this property will be delivered vacant at closing, allowing for immediate occupancy or renovations. Don't miss out on this fantastic chance to secure this valuable asset.

Stunning and beautifully designed three-level end unit condominium with luxury finishes throughout. Enter into an open-concept main level, highlighted by gleaming hardwood floors, recessed lighting, and expansive windows that flood the space with natural light. The kitchen offers stainless steel appliances, granite countertops, and custom cabinetry. The spacious living and dining areas are perfect for entertaining, with easy access to a private screened in porch. Primary bedroom with en suite offers one level living if desired along with a walk-in closet with ample storage. Upper level includes oversized entry room that allows for a wide-range of functionality. Two additional bedrooms with large closets and a full bathroom. Finishing off in the lower level is a tremendous family room with

Stunning and beautifully designed three-level end unit condominium with luxury finishes throughout. Enter into an open-concept main level, highlighted by gleaming hardwood floors, recessed lighting, and expansive windows that flood the space with natural light. The kitchen offers stainless steel appliances, granite countertops, and custom cabinetry. The spacious living and dining areas are perfect for entertaining, with easy access to a private screened in porch. Primary bedroom with en suite offers one level living if desired along with a walk-in closet with ample storage. Upper level includes oversized entry room that allows for a wide-range of functionality. Two additional bedrooms with large closets and a full bathroom. Finishing off in the lower level is a tremendous family room with

Welcome to 551 Tamarack Road! A beautifully updated and maintained Cape-style home, nestled on 1.28 acres in picturesque Pittsfield, MA!This charming 4-bedroom,2-bath residence boasts a perfect blend of modern amenities and classic charm. Step inside to discover a spacious, light-filled living area, ideal for gatherings and relaxation.The eat in kitchen features contemporary finishes and ample storage, seamlessly connecting to the dining area. Enjoy the convenience of 2 well-appointed bathrooms and generously sized bedrooms, perfect for family and guests.Outside, the expansive yard offers endless possibilities for outdoor activities, gardening, or simply enjoying nature.Meticulously maintained and set in a peaceful setting, this home is a true gem just waiting for you to make it your own!

Welcome to this stately raised ranch nestled in one of Pittsfield's most sought-after neighborhoods--Barkerville. Offering 1,896 square feet of thoughtfully designed living space, this home blends comfort, efficiency, and natural beauty in a truly special setting. Set on a cozy, private lot, the property is framed by mature evergreen trees, classic stone walls, and a peaceful brook flowing through the backyard. A grand entrance and custom walkway create a striking first impression, while the home abuts conservation land, providing direct access to scenic hiking trails and a serene, nature-filled backdrop year-round. Ideally located in the heart of the Berkshires, you're just minutes from world-renowned destinations including Tanglewood, the summer home of the Boston Symphony

OPEN HOUSE CANCELLED! Experience the perfect blend of professional utility and luxurious comfort at 1 Almon Ave., a beautifully constructed and impeccably maintained retreat located in a BG-zoned area. This home offers an exceptional opportunity for those looking to operate a business or maintain a home-office setup without sacrificing lifestyle quality. The main residence provides four spacious bedrooms, including a convenient first-floor bedroom w/ a walk-in closet, complemented by four full bathrooms. At the heart of the home, the gourmet kitchen showcases custom hickory cabinetry paired with solid granite countertops. The second floor--which, along with the stairs, will feature new carpet--includes three additional bedrooms, a family room, a full bath with laundry, and a