779 properties for sale in Pittsfield city, Berkshire County Massachusetts

Downtown Creative District Investment Opportunity Positioned in the heart of Pittsfield's vibrant Downtown Creative District, this fully occupied and professionally managed four-family property offers investors a rare blend of stable income and exceptional location. Just steps from the renowned Barrington Stage Company, residents enjoy easy access to some of the city's best entertainment, dining, shopping, and cultural attractions. Each spacious unit features one to two bedrooms, providing comfortable living spaces that appeal to a broad tenant base. The property's prime downtown setting, strong occupancy history, and professional management make it a turnkey investment with immediate cash flow potential. Whether you're looking to expand your portfolio or secure a well-located multifamily asset in one of the Berkshires' most desirable urban neighborhoods, this attractive income-producing property is an opportunity not to be missed

To Be Built Home - Create your custom, energy-efficient, low-maintenance home with flexible floor plans! Photos, prices, and layouts are for display only and subject to change with market and site conditions. Plans may be modified, changed and repriced. You'll select all colors and most finishes for a fully personalized build. Home price includes the 8.94-acre lot (MLS #248342), featuring a private well, installed septic system, underground electric, and a 1,000-gallon underground propane tank. A proposed septic easement accommodates an abutting lot. Lots may be purchased separately. HOA maintains driveway and common land. Covenants require a minimum 2,000 sq. ft. home with two-car garage. Taxes shown are for land only

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!

Adorable and accessible ranch in a secluded West Pittsfield neighborhood offers easy one-level living. Customized for a wheelchair user, this meticulously maintained home features wide doorways, a large bedroom with a reading/office nook and double closets, an open living room and kitchen layout, a bright, spacious bathroom, and a laundry/mudroom area with plenty of storage. Decking connects the inviting front porch to a private bistro-like patio bordered by raised garden beds in the fenced and landscaped backyard. Whether you have mobility issues now or would appreciate a small home with no stairs in which you can age in place, this could be your sweet Berkshire retreat

Condo at Twelve Oaks Village. End of Cul-de-sac with Mountain views. This unit offers lots of Privacy being an end unit. Come enjoy Tennis Swimming pool and Fitness center all on property. 3 Full floors of living space with Primary Suite/Walk in Closet on 1st floor. Spacious open floor plan to enjoy entertaining with plenty of outdoor space with screened in porch and private deck. Enjoy Easterly Views of October Mountain. Plenty of room for family and friends

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

Offering an affordable path to homeownership, this property is ideal for buyers ready to trade renting for a place of their own or investors looking to expand their rental portfolio. The first floor includes an eat-in kitchen, first-floor laundry, and a flexible room for additional living space. Bring your ideas and make it your own over time. A covered back patio extends your living space outdoors, while the fenced backyard offers room for pets. Conveniently located in the heart of Pittsfield with easy access to downtown, shopping, restaurants, schools, public transportation, and major commuter routes

Excellent investment or owner-occupied opportunity! This two-family flat offers two 2-bedroom, 1-bath apartments in a convenient Pittsfield location. Features include hardwood floors, a walk-up attic, public water and sewer, natural gas heat and hot water, two electric meters, one boiler, two hot water heaters, a spacious backyard, and ample off-street parking. The first-floor unit is owner-occupied, while the second-floor unit is vacant and in need of repairs, offering excellent value-add potential. Conveniently located near Berkshire Medical Center, downtown, schools, parks, shopping, restaurants, and cultural attractions. Property is being sold AS IS

Spacious and inviting 4-bedroom, 3-bath home offering comfort, efficiency, and great indoor-outdoor living. Beautiful wood floors run throughout the main living areas, adding warmth and character. The private primary suite features its own bath and sliding doors leading to a deck that overlooks a fully fenced backyard-perfect for relaxing or entertaining. Enjoy the added bonus of a covered patio and a handy storage shed for all your outdoor needs. The partially finished lower level provides flexible space for a home office, gym, or recreation area. Energy-saving solar panels help keep electric costs down,and the convenient close proximity to the lake makes this home as practical as it is appealing

Immaculate and beautifully updated free-standing home offering effortless one-level living. The open-concept floor plan seamlessly connects the living, dining, kitchen, and den areas, all enhanced by abundant windows that fill the space with natural light. The chef's kitchen features quartz countertops, stainless steel appliances, and a generous center island ideal for entertaining. Three spacious bedrooms and two full baths provide comfort and flexibility. Highlights include gleaming wood floors, a gas fireplace, and an oversized two-car garage. Enjoy exceptional amenities including a clubhouse, swimming pool, tennis courts, and a fully equipped fitness center. Ideally located with convenient access to all that the Berkshires have to offer

Move right into this beautifully updated Colonial on a quiet, tree-lined street! Thoughtfully renovated and lovingly maintained, this charming home is truly turnkey. Enjoy peace of mind with a new roof and new sewer line, along with a stunning new kitchen featuring stone countertops, upgraded stainless steel appliances, soft-close cabinets and drawers, and abundant workspace. The inviting floor plan is perfect for both everyday living and entertaining. Upstairs, the spacious primary bedroom offers two walk-in closets, providing exceptional storage. Outside, you'll find a fully fenced backyard-ideal for pets, play, or relaxing evenings-as well as a one-car garage. Need extra space' The basement includes a fantastic workshop area, perfect for hobbies, projects, or additional storage. Located in a desirable neighborhood with excellent schools, this lovely Colonial combines timeless character with modern updates, making it a home you'll be proud to own

Beautifully nestled in a gorgeous yard with wrap around deck and patio to enjoy the peace and tranquility of this setting! Pristine in every way with an open kitchen/dining area, which flows into the Living Room with gas fireplace, gorgeous formal dining room with lovely architectural details throughout; fabulous great room with stone, wood burning fireplace and cathedral ceiling plus a private office over the garage; the best mudroom ever with lots of cubbies and closets, updated kitchen and baths, large primary suite plus 2 additional bedrooms and full bath on the 2nd floor. The lower level is an added bonus with three finished rooms and a walk out to the stone patio and fire pit in the side yard. Brand new septic system! Nothing to do but move in and enjoy! Plus Lenox schools!

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 and 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 and 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!

Welcome home to this sweet split-level in desirable Southeast Pittsfield neighborhood. Offering 3 bedrooms and 1.5 baths, this well-maintained home features a spacious, well-appointed kitchen with granite countertops, abundant cabinetry, and great functionality for everyday living. Cozy up by the wood-burning fireplace or unwind in the inviting four-season room overlooking the deck and backyard. A walk out lower level is perfect as a home office, mudroom, or home gym, and there is and abundance of storage in the basement. Generously sized yard offers space to garden, play, or entertain. Just a short distance to nature tralis at both Brattlebrook Park, Kirvin Park and Canoe Meadows, this is a wonderful opportunity to enjoy comfortable living in a location you'll love

'A Perfect Place Farm' - a Berkshires Masterpiece on 17+ Acres The one you've been waiting for. a preeminent build in a premier location. 37 Main Rd checks off the wish list: sweeping views, modern comforts, privacy, location, and colonial era character, but in an immaculately kept turnkey 2002 home. Located in Tyringham valley, one of the Berkshires' most majestic locations, 37 Main Rd is idyllically sited on the northern slope of Tyringham valley, and faces to the southwest. The expansive front porch, sunroom, and living and sleeping quarters all are positioned to track the sun's daily arc across this picturesque east-west valley

Rare, renovated Berkshire investment compound on 0.59 acres in walkable Housatonic. This turnkey property features two separate legal duplexes (4 units total) offering stellar cash flow. The front home (392 Park St) features a 5BR/2BA unit, a sleek 2BR flat, and a prominent street-front walk-out lower level with incredible commercial/addition potential. The rear Swiss-Gothic home (394 Park St) hosts two updated 2BR units. Enjoy a sprawling backyard with mountain views, a community garden, and fruit-bearing trees. Fully insulated and optimized for easy management with 4 separate heating/electric systems, town sewer/water, and off-street parking for 10+ cars. Walk to Berkshire Mountain Bakery; minutes to Great Barrington and Tanglewood. A rare, turnkey find!

Renovated 4-family home, located on a corner lot in a great location in Pittsfield. There are two units on the first floor and two units on the second floor. The upstairs units also feature additional bonus space in the finished attics. Major updates were done in 2023-2024, with improvements that include new roof, new windows, new exterior doors, new second egresses for both upstairs unit, and new custom made fence. This is a solid building with 3,280 Sq ft and lots of character, and one of the most beautiful ones in the city! *Since the property sits on a corner, it is also known as 4 Courtland Pl. Pittsfield, MA 01201

Welcome to 22 Wealthy Ave located in the desirable Yankee Orchards neighborhood. Fresh, bright, and move in ready, this thoughtfully renovated home features beautifully refinished hardwood floors, a main level bedroom and full bath, plus two additional bedrooms upstairs with cedar lined closets, built in dresser drawers, and a newly renovated full bath. The updated kitchen includes a farmhouse sink, dishwasher, refrigerator, and oven/range. An attached garage with a new epoxy floor offers direct access to both the home and basement, where laundry hookups are conveniently located. Close to shopping, parks, schools, and downtown Pittsfield

Beautifully maintained inside and out, this move-in ready 3-bedroom Ranch offers the perfect blend of comfort, updates, and outdoor living. Gleaming hardwood floors, abundant natural light, and a stunning floor-to-ceiling stone fireplace create a warm, inviting living space. The finished lower level with custom bar adds exceptional bonus space for entertaining, hobbies, or relaxing. Outside, enjoy an expansive composite deck overlooking a beautifully landscaped, fully fenced backyard with fire pit and storage shed. Recent improvements include a new transferable 50-year roof (2025), fence (2025), remodeled bath, finished basement, deck, updated flooring, and more. Every room reflects the pride of ownership this home has received. Simply unpack, settle in, and enjoy

Located on the edge of Pittsfield's Downtown Creative District, this versatile colonial has served as professional office space for 20+ years and offers endless possibilities. Features include 6 private offices, a reception/waiting area, half bath, bonus room, handicap-accessible ramp, off-street parking, and a detached 4-bay garage with income potential. Ideal for medical, professional, nonprofit, wellness, counseling, mental health or substance abuse programs with residential living (subject to approvals), artist studios, or rental income. Restore it to a charming residence or continue its commercial use. Convenient to downtown and major routes in and out of the Berkshires. Bring your vision to where opportunity, location and flexibility come together. Talk to Tony

Welcome to this charming and low-maintenance ranch offering 1,131 square feet of comfortable single-level living. Situated on a quiet street in a desirable Pittsfield neighborhood, this two-bedroom, one-bath home is just minutes from Onota Lake and Pontoosuc Lake, providing easy access to boating, fishing, swimming, and year-round outdoor recreation. Inside, you'll find a functional floor plan designed for easy living, with bright, welcoming spaces that make everyday living and entertaining effortless. Step outside and enjoy your morning coffee on the inviting front deck or relax on the side patio surrounded by beautiful perennial gardens and colorful landscaping. The backyard offers additional outdoor space complete with a storage shed for gardening tools and seasonal equipment

Beautifully maintained 3-bedroom, 2-bath home offering the perfect blend of comfort, character, and country charm. The updated kitchen with quartz countertops flows into the dining area featuring a stunning floor-to-ceiling stone fireplace. Enjoy a spacious living room with wood stove and mini-split, a bright sitting area, and a first-floor office/flex room ideal for work, hobbies, or guests. Relax on the covered front porch or expansive rear deck overlooking the peaceful surroundings. Enjoy the tranquility of Savoy with convenient access to Adams (approx. 10 min), Hoosac Valley High School (approx. 5 min), North Adams (approx. 15 min), Pittsfield and Lenox (approx. 25 min), I-90 (approx. 40 min), and I-91 (approx. 50 min). Savoy's small community elementary school adds to the appeal of this welcoming location

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 brand-new 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!

Welcome to 1228 East St. A longtime family home filled with warmth, character and opportunity. Beautiful hardwood floors throughout much of the home. Updates include electric panel, blown in insulation, a new oil tank 2018 and new oil burner 2022. The spacious second floor kitchen area offers potential to create a two-family flat subject to city approval. A three-car garage offers extra space for storage, family vehicles or earning potential by renting out bays. Close to shopping, parks, recreation and everyday conveniences. This East st gem is full of possibilities. Schedule your showing today

Step into timeless elegance in this exceptional 6-bedroom, 3-bath historic residence, where classic architectural details blend seamlessly with thoughtful modern updates. Meticulously maintained and enhanced over the years, this one-of-a-kind home showcases the craftsmanship and character rarely found today. From the moment you enter, you'll be captivated by the grand, sun-filled rooms, gleaming hardwood floors, original built-ins, statement fireplaces, and exquisite stained glass windows that fill the home with natural light. With updated electrical, plumbing, boiler, sewer line and kitchen, this home is designed for everyday living and entertaining. Ideally located near downtown Pittsfield's cultural attractions this is a rare opportunity to own a piece of architectural history