Pittsfield Homes for Sale

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

76 Mullen Dr, Pittsfield
$599,900
3 Beds ⋅ 2 Baths ⋅ 5115778 MLS
Be in your new home before the Holidays! Brand New 3 Bedroom, 2 Bath Home designed for modern one level living. Open Concept Kitchen, Dining Area and Living Room - great for entertaining! Features include Master Suite with Double Vanity Sinks and Walk-in Closet, Laminate Flooring throughout, lst Floor Laundry, Central A/C and 2 Car Attached Garage. Set beautifully on a 4.5+ acre lot. Still time to choose some colors.

76 Mullen Dr, Pittsfield
20 Depot St, Pittsfield
$185,000
3 Beds ⋅ 1 Baths ⋅ 5114779 MLS
One of the older homes in town ready for it's new life. Bring your tool belt and ideas. Home is sold as is. Will not go FHA

20 Depot St, Pittsfield
22 Mullen Dr, Pittsfield
$589,000
3 Beds ⋅ 2 Baths ⋅ 5114541 MLS
Imagine celebrating your first Christmas in this beautiful new home, creating holiday memories. Discover the quality, craftsmanship, and throughout this three-bedroom home situated along a picturesque dead-end road. From the moment you arrive and step inside, the attention to detail is evident. The thoughtfully designed open-concept kitchen, dining, and living area creates a warm, inviting atmosphere. The rear-facing primary bedroom with private bath offers a peaceful retreat, while convenient first-floor laundry adds to the home's practical design. Step outside onto the beautiful rear deck, an inviting place to enjoy your morning coffee, or to simply appreciate the natural surroundings. The finished bonus room in the walkout lower level provides additional living space, perfect for a game room, exercise area, or another comfortable place to unwind and relax. Quality features include Matthew Brothers Walcott windows, a 10-foot foundation, central A/C, LP SmartSide exterior siding with a 50-year warranty, a hybrid water heater, a drilled well producing 15 gallons per minute with a constant-pressure pump, a high-efficiency LP gas forced-air furnace, and a heated garage, to name just a few. Enjoy the benefits of brand-new construction, modern systems, and quality without the time and stress of building yourself. Set in an elevated country location, the property offers the exciting potential for beautiful views of Berry Pond and the surrounding mountains with selective tree clearing. Looking for even more acreage and privacy? The adjoining 2.95-acre parcel, Lot 1 (MLS #5088211), is also available for purchase, offering the opportunity to expand your property to a combined 5.19 acres! Imagine the added privacy, outdoor recreation, and possibilities that additional land could provide. Enjoy country living while remaining convenient to local amenities, and the many attractions that make Pittsfield so special. Come envision the possibilities at 22 Mullen Drive!

22 Mullen Dr, Pittsfield
115 Park Pl, Pittsfield
$579,000
5 Beds ⋅ 3 Baths ⋅ 5114515 MLS
Tucked away at the end of a gravel road, this private 5-bedroom, 3-bath home sits on 1.8 acres with a small river running below the house. In the warmer months you can hear the water from the deck and yard. A finished basement with extra room for guests, a game room, or a gear and media space is a fantastic addition on the lower level. There is a fireplace for cool Vermont evenings, a deck for taking in the private setting. The drive is easy to Killington and Pico for winter skiing, and Sugarbush is within reach too. In summer and fall you’re close to hiking, golf, and mountain biking. A great fit for a primary home, second home, or four-season getaway. Come check out this home for yourself today!

115 Park Pl, Pittsfield
75 Concord Hill Rd, Pittsfield
$267,000
2 Beds ⋅ 1 Baths ⋅ 5114032 MLS
A single family home on almost one and a half acres under $275,000...say what?! This 2 bedroom manufactured home is situated on a fantastic piece of land that with a little bit of landscaping, will be absolutely beautiful. The paved driveway offers a ton of parking, the sprawling yard boasts an expansive place to play, entertain, garden or just grill and chill after a long day of work. The open concept living room and kitchen flow nicely into each other and there is an abundance of counterspace to host your kitchen gadgets. Travel down the hallway where you will find the first of 2 bedrooms, a large full bathroom, laundry area and the primary bedroom. Located only 20 minutes to Concord, 35 minutes to Manchester, 30 minutes to the Lakes Region and 55 minutes to Portsmouth, it doesn't get much more of a central location than this for work and fun. Welcome Home! *Offer deadline set for Saturday (10/17) at noon*

75 Concord Hill Rd, Pittsfield
324 Fellows Rd, Pittsfield
$2,450,000
4 Beds ⋅ 4 Baths ⋅ 5110057 MLS
Set within 210 acres of unspoiled forestland spanning Killington and Pittsfield, Vermont, The Tweed River Estate is a truly one-of-a-kind property, a private sanctuary where nature and craftsmanship meet. Designed by a renowned architect, the bespoke home is a masterwork in its own right, with exposed beams, high-end custom woodwork, and windows throughout that fill every room with light. Every detail, from the stonework to the finest materials, reflects the artistry of master stonemasons and skilled craftsmen. The house is perched above the Jimmy Dean Brook and the Tweed River, where the sound of running water settles peacefully over the property. Enveloped by forest on all sides, the stone, concrete, and timber structure sits on its mountain top setting so naturally that it feels less built than grown from the land itself, as if it had always been there. Large windows, stone patios and a second-floor porch frame views down the valley to the northeast and out across the surrounding woodland. On mornings when fog fills the valley below, the houses, elevated location gives the sensation of floating above the world on a cloud, a true private retreat. The property spans 210 acres across two contiguous parcels, the majority of which is untouched private forest in Pittsfield, with development potential on the 89-acre Killington parcel. Combining privacy, character, and genuine architectural originality, the estate remains just minutes from an impressive range of amenities, ski resorts, shops, and dining, making this a rare chance to own a home and landscape unlike any other in Vermont.

324 Fellows Rd, Pittsfield
7 True Rd, Pittsfield
$502,900
3 Beds ⋅ 2 Baths ⋅ 5107431 MLS
Nestled on 3.62 private acres, this inviting 3-bedroom, 2-bath home offers over 1,700 square feet of comfortable living space, thoughtful functionality, and features you'll appreciate in every New England season! The spacious kitchen offers plenty of counter and cabinet space, while abundant windows fill the home with natural light. A dedicated laundry room, flexible office or mudroom, and convenient first-floor bedroom and full bath provide everyday practicality and the option for one-level living. Upstairs, you'll find two generously sized bedrooms and an additional full bath. Cozy up beside the pellet stove for supplemental warmth and ambiance during chilly New Hampshire evenings! The large walkout basement offers a garage, workshop, bonus space, and plenty of room to store pellets, snowmobiles, and seasonal equipment. Two covered carports help keep vehicles protected from winter weather, while an additional shed provides even more storage. Generator wiring offers added peace of mind. Outside, enjoy the beautiful wraparound porch overlooking a wonderful mix of open lawn and wooded acreage. Set back from the road for added privacy, this property offers room to relax, explore, entertain, and enjoy the outdoors year-round.

7 True Rd, Pittsfield
253 Lookout 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
23 Targhee Dr, 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
340 Upper Michigan, 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
90 Deer Meadow Rd, 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
89 Townsend Brook 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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