779 properties for sale in Pittsfield city, Berkshire County Massachusetts

Some homes are purchased. Others become part of a family's legacy. Welcome to 109 Under Mountain Road. There is something unmistakably special about a Berkshire summer- evening stroll to Tanglewood, morning coffee overlooking protected meadows, or relaxing on the patio as the music of the Boston Symphony Orchestra drifts softly through the evening air. Bathed in extraordinary natural light, this architect-designed home embraces its breathtaking setting with soaring walls of glass, vaulted ceilings, exposed beams, skylights, and exquisite gardens. Thoughtfully designed for gracious entertaining and comfortable everyday living, the spacious first-floor primary suite allows you to enjoy the home with ease for years to come, while family and friends gather in beautifully appointed guest rooms

Opportunity to complete this renovation. Extensive site work has already been completed. $25,000 of Tree removal in 2022, kerosene tank removal in 2022, New Septic system designed and installed in 2023, Asbestos Remediation in 2025, New roof with new 3/4 plywood board in 2025, Installed 3 new remote controlled skylights in 2025, 3 more trees removed in 2025, U-driveway installed in 2025. Deeded Lake Rights and private beach for Owners Only. House is directly across from the path to the beach. Goose Pond is noted to be one of the cleanest lakes in Massachusetts. Finish this renovation or add a foundation of build your dream home in this highly sought after Lake Community

Exceptional custom-built home on 3.81 private acres in Pittsfield, offering the perfect blend of luxury, comfort, and privacy. Built in 2003, this well maintained 4-bedroom, 4.5-bath residence features a thoughtfully designed floor plan, driveway alarm, gas fireplace, home theatre system, 2-car heated attached garage with central vac. A private in-law suite, ideal for multigenerational living. An IMPRESSIVE 3,500 sq ft outbuilding providing endless possibilities for contractors, hobbyists, car enthusiasts, storage, or home-based business use. Equipped with a backup generator for added peace of mind. Enjoy peaceful outdoor living with a beautiful koi pond, private surroundings and trails for hiking, ATV's and snowmobiles. A rare opportunity to own a truly unique property in the Berkshires

Tucked into a peaceful wooded setting in Lenox, this architecturally distinctive contemporary home offers 2,189 square feet of living space on a private half acre lot. Designed with an asymmetrical exterior and a split level floor plan spanning three levels, this home offers unique character. Large windows fill the interior with natural light, while the open living areas create an inviting space. With its distinctive contemporary design and solid architecture, this property presents an exciting opportunity for thoughtful updates that can enhance both style and value. A rare chance to create something truly special in one of Lenox's most desirable settings. View in person and experience the warmth, character, and connection to nature that make this home so unique

Uniquely and tastefully renovated one-bedroom end unit condo with open living concept, and fully furnished! (some artwork excluded) Great room with fireplace, recessed lighting, ceiling fans, stainless appliances, microwave with expandable exhaust vent, modern bathroom with double shower, swanstone vanity sink, built in cabinet. Simply move in and live! New central air conditioner in 2012 and new hot water heater in 2015. Pretty laminate floating floor throughout, recessed lighting throughout all with dimmer controls, 7-day programmable thermostats in each room, extra quiet Kitchenaid dishwasher, all soft close upper and lower kitchen and bathroom cabinets, kitchen pullouts, detached garage with automatic opener, big entertaining pavilion and heated inground pool, and low, low HOA fees!

Gorgeous,Cute,Adorable, All three describe this 2 bedroom 1 bath southeast cape. Located on a quiet street this home offers a big private yard and a 2 car garage. The sunroom has new windows and the washer dryer are newer and staying with the house. Gleaming hardwood floors, fireplace and too many other amenities to mention. Come see iit!

Why rent when you can own in a delightful neighborhood. Immaculate ground level unit in the private country community of Forest Row located just a few minutes from downtown Great Barrington. Forest Row is a Community Land Trust Neighborhood. Easy care one level living with an open floor plan, private screened porch and a patio bordered by gardens and woods, surrounded by 21 acres of protected land for your enjoyment. Carport and garden shed. Easy access to Rudolf Steiner School, Great Barrington town center, Tanglewood, Skiing and other local attractions. This is a community land trust neighborhood for full-time year round living

Easy living in this move-in ready contemporary in southeast Pittsfield! Stylishly designed with a flexible floor plan. Enter into a light-filled living space with built-in cabinetry in the entry, spacious oversized eat-in kitchen that that opens to a large rear deck. Kitchen with quartz island/ stainless appliances. Oversized first floor bath with laundry. Additionally find a den/sleeping space with French doors for privacy. Primary suite is the entire upper level and features deep soaking tub. Many options for the finished lower-level walk-out recently enhanced with custom built-in storage. Efficient propane heat/hot water, this is a gem not to be overlooked. Convenient to all Berkshire locations, this like-new home is a must-see for full or part-time living!

Welcome to this impeccably maintained 4-BR, 2 bath residence offering comfort, style, and exceptional outdoor living. The updated kitchen features all new appliances, while the spacious layout provides plenty of room for family, guests, or a home office. Potential 1st floor BR! Step outside and discover your own private backyard retreat. Relax under the covered porch, entertain on the dining patio, or gather around the fire pit on cool evenings. Beautiful gardens add color and charm throughout the seasons, and the above-ground pool provides the perfect place to cool off and enjoy summer fun. Additional features include a one-car garage, well-maintained mechanicals, and pride of ownership evident throughout. Close to dining, shops, bus route and hospital! MOVE IN REA

Located in Southeast Pittsfield, this well-maintained Colonial offers timeless charm, thoughtful updates, and a floor plan that feels just as functional today as it did when it was built. Hardwood floors run throughout the home, and the inviting living room is anchored by a wood-burning fireplace with a bright sunroom just beyond-perfect for a home office, reading nook, or additional living space. The kitchen features granite countertops, cherry cabinetry, stainless steel appliances, and plenty of workspace, while the formal dining room provides the ideal setting for everyday meals or entertaining. Just off the kitchen, a mudroom and full bath create a convenient everyday entrance with direct access to the backyard. Upstairs, you'll find three bedrooms, including a spacious primary bedroom, along with a full bathroom. Step outside to enjoy a deck and patio overlooking the fully fenced backyard, offering a private space to relax, garden, or entertain. Two storage sheds provide plenty of

Located in a desirable neighborhood in Southeast Pittsfield, this three-bedroom, 1.5-bath home offers comfort, versatility, and exceptional value. The main residence features spacious living areas, large primary bedroom with walk in closet and laundry room, and a functional layout designed for everyday living. A standout feature of the property is the attached first floor apartment with an additional bedroom, and additional bathroom, perfect for extended family, guests, rental income, or a private home office. The property also includes an insulated workshop/barn, providing ample space for hobbies, storage, equipment, or small business needs. Enjoy outdoor living in the fenced backyard, ideal for pets, gardening, entertaining, or simply relaxing in your own private retreat

Welcome to 184 Melbourne Road in Pittsfield. This ranch style home boast two generously sized bedrooms, full bath, an open concept living room, kitchen and dining room. This home has been beautifully renovated and maintained throughout the years and it shows. Some of the recent updates include freshly refinished hardwood floors throughout, fresh interior paint, granite countertops, a large island complete with prep sink amongst many others. As you enter the home you are warmly greeted by an abundance of natural light. An attached one car garage adds to the functionality of this move in ready home. It is perfectly placed on approximately 0.59 acres of flat terrain. Don't miss the opportunity to make this your forever home!

3 bedroom, 1 bath ranch in Pittsfield's desirable Orchards neighborhood! Featuring beautifully refinished hardwood floors, this home offers comfortable one level living with plenty of potential to make it your own. Enjoy morning coffee or unwind in the screened porch overlooking the backyard. Additional features include a one car garage, full basement offering ample storage or workshop space, and a convenient location close to parks, schools, shopping, restaurants, and downtown amenities. A solid home in a great location. Don't miss this wonderful opportunity!

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 and 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal dining room with its magnificent shell-carved cove, to original cabinetry with rare wood inlays, hand-carved bookshelves, a classic butler's pantry, multiple stately fireplaces anchor the formal living spaces. Enjoy panoramic views and privacy from the grand porch overlooking 4 pristine acres. a state-of-the-art kitchen featuring Wolf and Sub-Zero, and no expense spared Geo-Thermal heating/cooling

Enjoy this beautiful property on Williams St. Large yard consisting of 2 lots with pastoral views across the street. This 4 large bedroom, 1 full and 2 half bath home is just waiting for your interior decorating ideas Hardwood floors in most rooms, fireplace living room, large dining room. Central air conditioning, Basement partially finished, including 1/2 bath. New roof in 2020 and solar panels replaced. Updated electrical, furnace serviced 2/25. New sewer line this month Solar Panels are owned and for hot water only

Sweet and Petite Cozy Colonial Centrally located and easily accessible, this charming 2-bedroom, 1-bathroom Colonial is ready to welcome its next owner. Enjoy peace of mind for years to come with recent improvements, including a new roof (2023), new boiler (2024), and an updated electrical panel (2024). Inside, you'll find a freshly painted interior and a refreshed bathroom (2024). Looking for a little extra flexibility' The lower-level bonus room offers great additional space for a home office or hobby room. Set on a manageable, low-maintenance lot, this home allows you to spend your weekends relaxing rather than doing yard work. Come see for yourself!

Spacious Southeast Pittsfield Ranch with great bones and endless potential! Generous room sizes and a thoughtful layout provide a wonderful foundation for additional updates that will make this home your own. A brand-new furnace offers added peace of mind, while the unfinished basement is ready for your vision, whether additional living space, a workshop, or recreation area. Outside, you'll find a dreamy backyard with exceptional privacy, perfect for relaxing, entertaining, or gardening. The property's strong fundamentals, desirable location, and setting make it an outstanding opportunity! Dog lovers will delight in nearby Kirvin Park with it's babbling brook and hiking trails just a half mile away

This custom-built home seamlessly blends country tranquility with modern convenience. Inside, a gracious foyer leads to formal and informal first floor living spaces designed for comfortable living and gracious entertaining. 4 bedrooms, 3 full and 2 half baths, including a large spacious primary suite, guest room with en suite bath, private home office, well appointed eat- in kitchen with sliders to deck and yard, a screened porch and 2 fireplaces that add warmth and character. The partially finished lower level offers a spacious family room and home gym while the unfinished space provides ample storage. 3 -car garage and spacious mudroom and first floor laundry. A rare opportunity to enjoy privacy, space, and the very best of Berkshire living. Moments from Pittsfield State Forest, Onota Lake, vibrant downtown dining, cultural attractions, and a short drive to Tanglewood, the location is truly exceptional

Welcome to this impeccably maintained 4-BR, 2 bath residence offering comfort, style, and exceptional outdoor living. The updated kitchen features all new appliances, while the spacious layout provides plenty of room for family, guests, or a home office. Potential 1st floor BR! Step outside and discover your own private backyard retreat. Relax under the covered porch, entertain on the dining patio, or gather around the fire pit on cool evenings. Beautiful gardens add color and charm throughout the seasons, and the above-ground pool provides the perfect place to cool off and enjoy summer fun. Additional features include a one-car garage, well-maintained mechanicals, and pride of ownership evident throughout. Close to dining, shops, bus route and hospital! MOVE IN REA

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

Presenting a distinguished multi-family property located at 53 Orchard St, Pittsfield, MA. This expansive 4 unit spans 2688 square feet of living area, offering a rare opportunity for sophisticated urban living or a strategic investment. This property includes six generously proportioned bedrooms, providing ample private accommodations across its two stories. The property's substantial lot size of 4160 square feet provides a significant footprint within the urban landscape. We invite you to discover the potential and unique character of this Pittsfield address. Three Units are vacant and recently remodeled with market rents averaging about 1395.00 in the area. One Unit is rented month to month at 950.00

Welcome to this spacious 3-bedroom, 2-bath home offering 1,920 square feet of living space in Pittsfield's desirable Morningside neighborhood. This home blends classic character with several major updates already completed, including a newer roof (2025), replacement windows, oil tank (2024), boiler (2019), and sewer line (2019). The flexible floor plan provides plenty of room for everyday living, entertaining, or multi-generational needs. Enjoy an eat-in kitchen, full basement with interior and exterior access, a detached one-car garage, and a generous lot with mature landscaping. Conveniently located near parks, schools, restaurants, shopping, and downtown Pittsfield. Located in an RM-zoned district, this property may offer future multi-family or investment potential, subject to buyer due diligence. Property is being sold AS IS. A great opportunity for investors, cash buyers, or conventional financing buyers looking to add value while building equity through cosmetic improvements

Own Pittsfield History in this distinctive solidly built Georgian-style brick estate set proudly atop a hill in this coveted enclave of stately residences. Live on historic Crofut St. near the esteemed Pittsfield Country Club, Up Street Cultural Art District and ideally minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional detail and character boasting five bedrooms, two and half baths thoughtfully improved by this long term owners' commitment to preservation and restoration. This prominent manor style home MAY BE coupled with the neighboring Little Red Guest House with 3 bedrooms, 2 bath, first floor in-law suite and 2 car garage to host family, friends. Enjoy carefree ownership central to all that is Berkshire!

Welcome to this beautifully built new construction home offering the perfect blend of style, efficiency, and comfort. Featuring 2 spacious bedrooms and 1.5 bathrooms, this thoughtfully designed home boasts an open-concept layout with bright natural light, modern finishes, and quality craftsmanship throughout. The main living area flows seamlessly into the kitchen and dining space, creating an inviting atmosphere ideal for everyday living and entertaining. The kitchen offers sleek cabinetry, contemporary fixtures, and ample counter space. Upstairs, you'll find two generously sized bedrooms and a full bathroom designed with clean, modern touches. Enjoy the convenience of a first-floor half bath, energy-efficient systems, low-maintenance construction, and a first-time live-in experience

Welcome to this charming four-bedroom, three-bath home nestled in a desirable Southeast Pittsfield neighborhood. Lovingly maintained and well insulated through the years, this home offers a warm and inviting atmosphere with a wonderful blend of original character and everyday comfort. Inside, you'll find hardwood flooring, spacious bedrooms, two first-floor bedrooms and 2 full bathroom, and an expansive addition at the rear of the home that provides flexible living space to suit your needs. The generous mudroom offers excellent functionality and storage, while updated windows help enhance efficiency and natural light throughout. The partially finished basement provides additional living or hobby space, along with ample storage opportunities. Outside, enjoy beautiful flowering gardens and mature landscaping that create a welcoming setting throughout the seasons. Filled with charm and ready for your own personal updates and touches, this well-cared-for home offers a wonderful opportunity