717 houses for sale in Pittsfield city, Berkshire County Massachusetts

This property has an immaculate fenced in back yard for all your summer activities. Inside boasts beautiful hardwood floors, Full bath on the 1st and 2nd Level. Large mudroom from the main entrance for all you winter and mud season needs. A paved driveway with plenty of private parking. A walkout from the lower level to the parking area with a tuck under car port. Recently painted exterior and a screened in porch in the back. 3 large bedrooms and a perfect den for office space or media room. Centrally located in the Berkshires within close proximity to Shopping, Groceries Stores and Tanglewood!

This 3-bedroom, 2-bath ranch sits on a quiet street in one of Pittsfield's most desirable areas. The home has been meticulously maintained with an efficient layout and no wasted space. The kitchen was fully updated with quartz countertops. The basement has also been updated, adding real living space, not just storage. Both bedrooms have California Closet built-ins. Outside, a 32x16 inground pool with a new gas heater anchors the backyard. A newly installed front patio adds another spot to sit outside. There's also a 2-car garage. Meticulously maintained, right down to the details, this is a rare find on Pittsfield's East Side

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

Move right into the vacant unit and start generating income from the other. The property includes a small, easy-to-maintain yard, perfect for enjoying outdoor space without extensive upkeep. While there is no off-street parking, the property's functional layout and income-producing potential make it an excellent value. Whether you're looking to owner-occupy or expand your investment portfolio, this duplex is ready for its next owner

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 garage. a rare amenity in such a convenient in-town location. Whether you're expanding your portfolio or seeking a turnkey multi-family investment, this property offers an excellent combination of location,

Welcome to 34 Daniels Avenue, part of the Westside Legends Attainable Housing Program. This updated Pittsfield home offers a comfortable layout with recent improvements throughout, including new flooring, new appliances, and refreshed bathrooms. The interior feels clean, bright, and move-in ready, while still offering a practical and manageable footprint for everyday living. Conveniently located near downtown Pittsfield, local parks, restaurants, shopping, and cultural attractions, this home provides an excellent opportunity for qualified buyers seeking attainable homeownership in a central Berkshire location

One of the most exceptional homes to come to market, this remarkable property blends timeless elegance with resort-style living. Featuring 5 bedrooms, 3.5 baths, including private guest quarters with bath and secondary staircase, this home offers both sophistication and versatility. The luxurious primary bedroom suite is a true retreat, complete with a spacious en-suite bath designed for comfort and relaxation. A stunning new kitchen serves as the heart of the home, thoughtfully designed for both everyday living and refined entertaining. Impeccably curated interiors extend seamlessly to breathtaking outdoor spaces highlighted by a spectacular heated in-ground pool, extraordinary landscaping, and meticulously maintained grounds. A true masterpiece of design and luxury living. Join the Country Club of Pittsfield for golf, tennis and pickelball just 1.5 miles away. Downtown Pittsfield's restaurants, museum and theaters are a short 15 minute walk. Drive 15 minutes to downtown Lenox and Tan

Discover a fantastic investment opportunity at 96-98 Brown Street, Pittsfield. This two-family home features a cozy 2-bedroom, 1-bath unit on the first floor, perfect for easy living, and a spacious 3-bedroom, 1-bath unit on the second floor, ideal for owner occupied or Investors alike. Recent upgrades include a new roof, some fresh paint, updated 100 amp electrical panels, new windows, and a recently installed boiler, ensuring peace of mind for years to come. Each unit has separate utilities, enhancing convenience and efficiency. Enjoy the added benefit of off-street parking. With the property being vacant at closing, this gem is ready for your personal touches or rental potential!

Exceptional Investment Opportunity: Versatility and Prime Location Discover a property that offers unparalleled flexibility in one of Pittsfield's most active commercial corridors. Situated on a sprawling 0.92-acre lot directly across from Berkshire Crossing, this unique property presents a rare 'blank canvas' for homeowners and investors alike. Currently configured for mixed-use with a professional office space on the main level and a spacious 2-bedroom apartment on the second floor. Easily convertible back into a large Single-Family home for those seeking significant acreage and convenience in the heart of town

Investor Special! This gutted duplex offers a blank canvas with 6 bedrooms, 2 bathrooms, and 2,000 sqft of space, plus the possibility of additional living space in the attic. this property features a large backyard with a serene water stream, A standing garage remains on site for additional storage or future use. Situated on a 13,108 sqft lot, can also be bundled with 40 Pecks Rd and 48 Brown st (Pittsfield) for even greater investment potential. Endless possibilities await, renovate, rebuild, or reimagine this space to maximize returns! Schedule a showing today!

Introducing 39-41 Bartlett Avenue, a classic three-family Victorian in the heart of Pittsfield, offering a fantastic investment opportunity. This fully occupied property provides immediate income potential and features separate natural gas utilities for each unit. The home boasts vinyl siding and replacement windows, combining classic charm with practical updates. Ideally situated just moments from downtown. Whether you're looking to expand your portfolio or owner-occupy this well-located multi-family is one you won't want to miss

Conveniently located near shopping, dining, and the the Ashuwillticook Rail Trail for biking, walking, and outdoor recreation, this 3 bedroom, 2 bath modified Cape with first floor home office/den, offers comfort and opportunity. Featuring hardwood floors, a spacious deck, and a large backyard perfect for outdoor enjoyment. This well built home has great bones and is ready for its next chapter. The flexible floor plan provides ample living space, while the central location makes daily errands and recreation a breeze. A significant improvement is already underway, with the seller installing a brand-new sewer line prior to closing, providing added peace of mind for the next owner. Don't miss this chance to make this well-located home your own

Welcome to easy living at 691 Crane Ave, Pittsfield! This single-level ranch offers the perfect blend of convenience and peace of mind, highlighted by a 2-year-old roof and a two-car garage. Inside, you'll find a highly functional layout featuring fantastic space in the basement-an ideal setup for your favorite crafts, a home workshop, or weekend hobbies. Step out back to find a standout feature: a large, fully fenced-in yard that provides a wonderful private outdoor retreat. Nestled in a highly convenient location close to local shopping, dining, and schools, this move-in-ready home is designed for an effortless lifestyle. Don't miss this Berkshire gem!

Compare for value in the Lenox market! Sweet, petite, move-in ready ranch. Living room and bedrooms with hardwood floors; two nicely updated bathrooms; eat-in kitchen opens to spacious, private rear deck. Bonus features include the oversized two car garage, Buderus boiler for natural gas heat, and over a 1/2 acre of open sunny lawn. Easy access to shopping, dining and all of the Berkshires' cultural attractions

A solid and versatile two-family flat located in Pittsfield's Newell Street neighborhood, 21-23 Newell St offers a great opportunity for owner-occupants, investors, or multi-generational living. This traditional New England multi-family home features two spacious units, each with private entrances. Just minutes to, Elm St Plaza, diners, restaurants, banks, variety store, and Ice Cream shop and more! Easy access to Downtown Pittsfield dining and shopping, Berkshire Medical Center, Local schools and parks, Cultural attractions like the Colonial Theatre and Barrington Stage, Easy access to Route 7 and Route 20

Located on a quiet street in Housatonic, this charming cottage offers easy single-level living in a peaceful neighborhood setting. Set on a sunny double lot, the property provides extra outdoor space and flexibility with room to garden, entertain, play, or simply enjoy the surroundings. Inside, the home features an efficient layout filled with natural light, creating a bright and comfortable feeling. An oversized garage adds valuable storage and space for hobbies, tools, or workshop use. One of the highlights of this location is being within walking distance to Old Maids Park, where you can enjoy fishing, swimming, and a picnic area along the river. This sweet cottage offers a wonderful opportunity for those seeking a manageable home with everyday simplicity and nearby recreation. Minutes to downtown GB, and local amenities!

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

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

Income producing 3-family home with almost 4,000 SF of living space, featuring two 3 bedrooms/1 bath apartments and one 3 bedroom/2 bath apartment, each one with its own laundry hookups. All 3 apartments have lead compliance certificate!There are vinyl replacement windows, newer heating systems, newer roof done in 2022, and separate natural gas heat and hot water and electricity for each unit.Hall Place is a dead end street and the property sits on a large corner lot, offering plenty of parking and good yard space.This is a great income producing property with rents totaling $74,472/year. All apartments are rented through Section 8. *Interior photos shown are from 2025 before tenants moving in

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

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

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