Pittsfield Homes for Sale

Welcome to Pittsfield, a charming city nestled in the heart of the Berkshires, Massachusetts. Known for its rich history, vibrant arts scene, and stunning natural landscapes, Pittsfield offers a unique blend of small-town charm and urban amenities. With a population of around 43,000, this city boasts a diverse community that celebrates its cultural heritage through various festivals, art galleries, and theaters. Enjoy the breathtaking views of the surrounding mountains, explore the picturesque parks, or take a leisurely stroll along the scenic waterfront of Onota Lake.

For those considering a move to this delightful city, there’s an array of homes for sale that cater to various lifestyles and budgets. Whether you're searching for a cozy single-family home with a white picket fence, a modern condo with urban conveniences, or a sprawling estate with acres of land, Pittsfield has something for everyone. The real estate market here is thriving, with properties that reflect the area's unique character and charm.

Families will appreciate the excellent schools, while outdoor enthusiasts can take advantage of the nearby hiking trails, ski resorts, and recreational activities. With a strong sense of community and a commitment to preserving its natural beauty, Pittsfield stands out as a wonderful place to call home.

Explore the available homes for sale in Pittsfield today and discover why so many have chosen to make this vibrant city their own. Your dream home awaits in this picturesque corner of Massachusetts!

Newest Pittsfield Homes for Sale

$399,900

2 Beds ⋅ 1 Baths ⋅ 5108433 MLS

Character, privacy, and room to grow, all on 3 acres. This split-entry home offers 1,370 square feet of finished living space above grade, with comfortable single-level living and a full lower level waiting for your vision. It's a blank canvas ready to become whatever you need most: a family room, home office, gym, workshop, or additional living space. Buy the home that fits you now, and let it grow as your plans do. Outside is where the property truly sets itself apart. A custom-built gazebo sits beside the home, its stained-glass windows casting color across a space made for morning coffee, evening gatherings, or a quiet hour with a book. Beyond it, you'll find a collection of additional buildings and structures created by the previous owner as places to relax and enjoy the outdoors. Together they give these grounds a personality you won't find on a typical lot, and leave the next owner plenty of room to reimagine them. With roughly 300 feet of road frontage and three full acres to spread out on, there's space for gardens, pets, projects, or simply quiet. And you're still minutes from downtown Pittsfield with convenient access to Concord, Manchester, and the Lakes Region. An approachable entry point, real land, and a lower level full of possibility; 360 Dowboro Road is a rare chance to own something with genuine character and make it your own. Schedule your showing and come see what this one could become.

360 Dowboro Rd, Pittsfield

$539,900

3 Beds ⋅ 2 Baths ⋅ 5107431 MLS

Welcome to 7 True Road in Pittsfield! This inviting 3-bedroom, 2-bath home offers 1,700+ square feet of living space and a comfortable, versatile layout designed for everyday living. The kitchen has plenty of counter and storage space for cooking and entertaining. There is a dedicated laundry room, as well as a flexible office or mudroom space. The home is filled with windows, allowing natural light and the beautiful setting to shine throughout. The main floor features a spacious bedroom and full bathroom, offering convenient one-level living and the flexibility to make this your forever home. Upstairs, two additional generously sized bedrooms provide plenty of space, plus an additional full bath. There is also ample closet and storage space throughout the home, including the large walk-out basement with a garage, workshop, and bonus room space. Outside, you can enjoy the 3.62 acres from the beautiful wraparound porch. There is also a shed and two carports to store all your outdoor toys and equipment. The home is set toward the back of the property, offering wonderful privacy, with a nice mix of wooded areas and open space. Join us for the open houses: Friday, 9/4 | 6–8 PM Saturday, 9/5 | 10 AM–12 PM

7 True Rd, Pittsfield

$300,000

3 Beds ⋅ 2 Baths ⋅ 5106738 MLS

Under contract but will continue to show. Welcome to 28 South Main Street in Pittsfield, NH! This charming 3 bedroom, 2 bath Cape sits high on .47 acres and offers a wonderful opportunity for those looking to start out, settle down, or downsize. Filled with character and warmth, the home features hardwood floors in the living room and a woodstove to take the chill off on those cold New Hampshire nights. The first floor offers a comfortable bedroom, renovated bath, dining room, kitchen, and a convenient laundry room that doubles as a pantry. Enjoy the sunshine and fresh air from the inviting 3 season porch, with two exterior decks providing plenty of space for relaxing, entertaining, or simply enjoying the outdoors. Upstairs, you'll find two additional bedrooms and a 3/4 bath. The full walk-out basement adds valuable space and flexibility, whether you envision a workshop, home gym, hobby area, or additional storage. Outside, there's a handy shed for your gardening and outdoor tools, along with a patio area just off the deck. Recent updates include a new heating system, replacement windows on the first floor, renovated bathrooms, and a nicely paved driveway. Conveniently located close to the amenities of downtown Pittsfield while offering a comfortable setting to call home, this is one you'll want to see!

28 S Main St, Pittsfield

$424,900

2 Beds ⋅ 1 Baths ⋅ 5105849 MLS

Back On Market, Enjoy this almost brand new 1979 ranch home, completely rebuilt from the studs out, including new roof, windows, siding, electrical, and plumbing. Set on 2 private acres just 4 minutes off Route 28 and close to the Chichester line, this 2 bedroom ranch offers a flowing floorplan and a sunroom addition facing the rear of the property. The kitchen has been fully rebuilt with soft close shaker cabinetry, quartz style countertops, and stainless steel appliances including a smooth top range, overhead microwave, and dishwasher. Rich hardwood flooring runs throughout the main living areas, tying the open kitchen, living room, and sunroom into one bright, cohesive space. The sunroom brings in abundant natural light through oversized sliders and windows, framing peaceful, private wooded views and offering direct access to the rear deck, perfect for morning coffee or evening relaxation. A full basement adds valuable storage or future finished living space. The oversized attached garage is insulated and wired, ideal for a workshop, extra vehicles, or seasonal equipment storage, with direct entry into this beautifully updated home. Located at 172 Webster Mills Rd in Pittsfield, this move in ready ranch offers the rare combination of privacy, updated systems, and quality craftsmanship.

172 Webster Mills Rd, Pittsfield

$479,000

3 Beds ⋅ 3 Baths ⋅ 5105259 MLS

Nestled among the woods of Pittsfield's coveted Townsend Brook area, this beautifully maintained and thoughtfully updated chalet captures the essence of the quintessential Vermont mountain getaway. Designed in the tradition of a European alpine chalet, the main living level occupies the second floor, maximizing natural light and creating a warm, inviting space for après-ski gatherings or quiet evenings by the fire. Recent improvements include an upper-level bump-out with a charming reading nook and convenient powder room, beautiful maple hardwood floors, modern lighting and ceiling fans, and beautifully remodeled bathrooms. An enclosed former storage shed has been transformed into a generous mudroom and first-floor laundry, complete with a wall of built-in cabinetry for skis, bikes, boots, and outdoor gear. A spacious wraparound deck extends the living space outdoors, offering both sunny and shaded spots for morning coffee, al fresco dining, or gathering with friends. Surrounded by the Green Mountains, miles of mountain biking and snowmobile trails are practically at your doorstep, while world-class skiing at Killington and Pico is just minutes away. With easy access from Montreal, Boston, and New York City, this turnkey retreat offers an appealing combination of comfort, recreation, and value - equally suited to weekend escapes, investment income, or year-round living.

253 Lookout Rd, Pittsfield

$485,000

4 Beds ⋅ 2 Baths ⋅ 5104770 MLS

Welcome to 23 Targhee Drive. Tucked away on 3.12 private, quiet acres this home offers the privacy you want and the convenience and access you need with three floors of efficient, usable living space. Just five minutes from downtown Pittsfield with stores, restaurants, parks, and a theatre. This house is also close to Concord which offers the amenities of a bigger city and is just 15 minutes away. Manchester is also convenient and is only 30 minutes away. This home offers 4 spacious bedrooms. There are 2 full baths, including a bedroom upstairs with its own bathroom. There is a spacious living room and dining area on the first floor which is right off the large kitchen, making entertaining convenient. The yard offers mature landscaping and a picturesque setting to enjoy all 4 seasons. There are plenty of large trees offering shade on those hot summer days. The yard is large enough to enjoy playing games outside with guests and outside entertaining and cookouts. There is a work bench in the basement to work on any projects you may have. The basement has a wood stove which will also help heat the house to keep those winter heat bills low. The heating system is forced hot water fueled by propane as well as on-demand hot water, which is also propane powered. Book your showing today.

23 Targhee Dr, Pittsfield

$150,000

3 Beds ⋅ 1 Baths ⋅ 5103783 MLS

One acre private lot. Listed as a builing lot with an artesian well, power and roughed in driveway. Condition of the mobile home is unknown. Owner has not entered the home in years. Remove the mobile home and build your home.

251 Webster Mills Rd, Pittsfield

$635,000

4 Beds ⋅ 1 Baths ⋅ 5103418 MLS

Location and quality of land is the attraction of this original farmhouse in Pittsfield just 13 miles from Killington Mt. 61 acres of prime land ready for development or conservation. 1825 farmhouse is in need of complete rehab or build new uphill to gain mountain views and privacy. Property is situated on both sides of Upper Michigan Rd just above the village and just below the Hawk Mt community. Opportunities galore with this parcel.

340 Upper Michigan, Pittsfield

$525,000

3 Beds ⋅ 3 Baths ⋅ 5103414 MLS

Welcome to the home you've been waiting for! This beautifully maintained Colonial offers the perfect blend of space, comfort, and convenience, nestled on a picturesque 1.51-acre lot with a peaceful country feel. Inside, you'll find open concept living with ample space in the the gourmet kitchen/dining area, office space, and living room with fireplace. Additionally there are three spacious bedrooms, two full bathrooms, and a convenient half bath. The bright and inviting floor plan is ideal for both everyday living and entertaining. A standout feature is the enormous bonus room above the attached garage offers endless possibilities as a fourth bedroom, family room, game room, home office, or fitness space. Enjoy the privacy and tranquility of the expansive yard while remaining just a short commute to Concord, Manchester, and the Lakes Region. Whether you're looking for room to grow, space to entertain, or simply a place to relax and enjoy country living, this exceptional home has it all. Don't miss your opportunity to make this stunning Colonial your next home!

90 Deer Meadow Rd, Pittsfield

$348,500

2 Beds ⋅ 2 Baths ⋅ 5103104 MLS

Tucked back from the road on just over three private acres, this well-maintained one-story home offers easy, single-level living in a quiet rural setting, with room to roam, tinker, and settle in. Step inside to a light-filled, open layout where the kitchen, dining area, and family room flow together, making everyday living a breeze. The adjoining living room adds a second gathering space, while a dedicated laundry room and pantry keep things functional. A screened porch off the kitchen invites you to enjoy three-season mornings and evenings overlooking the wooded lot. The primary suite features a spacious bedroom, a walk-in closet, and a private en-suite bath. A second generously sized bedroom with its own nearby full bath offers flexibility for family, guests, or a home office. Downstairs, an attached one-car garage and a large unfinished basement provide abundant storage. Outside, the property really shines: 3.01 acres of space with several outbuildings, including multiple wood-frame sheds, great for extra storage, a workshop, or hobby farm use. The home features low-maintenance vinyl siding and a durable standing-seam metal roof (updated with new skylights). Looking for an affordable home on a private lot? Look no further!

380 Dowboro Rd, Pittsfield

$420,000

3 Beds ⋅ 2 Baths ⋅ 5101870 MLS

This well-maintained ranch has been owned by the same family for over 60 years! Great location in a neighborhood close to town and major routes. The first floor features beautiful hardwood floors, large front living room, dining room, 3 season room with root cellar, 3+ bedrooms, 2 baths and an egress to the oversized one stall garage. Great flex space in the lower level with playroom, laundry room, utility room, 3/4 bath and 3 guest rooms or offices. The most AMAZING yard with vegetable and perennial gardens, fruit trees, out building and is partially fenced in. Proudly owned and meticulously cared for, this home is ready for its next chapter. Quick close is possible!

12 Norris Rd, Pittsfield

$559,000

5 Beds ⋅ 3 Baths ⋅ 5099518 MLS

Located in the heart of central Vermont, this fully furnished and equipped five-bedroom home provides convenient access to Killington Resort and nearby snowmobile trails, making it an ideal choice for skiers, mountain bikers, hikers, golfers, and outdoor enthusiasts alike. With an established rental history, it also presents an excellent opportunity as a vacation home with income potential. Inside, the home has a warm and welcoming atmosphere, with a cozy propane fireplace serving as the centerpiece for relaxing after a day outdoors. The comfortable kitchen and living area create an inviting space to gather with family and friends, while the five-bedroom layout offers plenty of room for guests, multiple families, or a dedicated home office. After a day on the slopes or the trails, unwind in the hot tub or head into the charming town of Woodstock to enjoy local restaurants, shopping, and classic Vermont character. Whether you're looking for outdoor adventure, a peaceful weekend getaway, or an investment property, this home provides easy access to many of the region's most popular attractions. With its flexible layout, proven rental appeal, and prime location in the Green Mountains, 89 Townsend Brook Road is ready for its next chapter. Call today for more details or to schedule a private showing.

89 Townsend Brook Rd, Pittsfield

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