Pittsfield Real Estate

Pittsfield Real Estate

Welcome to Pittsfield, Massachusetts—a charming city nestled in the heart of the Berkshires, where natural beauty meets rich cultural heritage. Known as the "Heart of the Berkshires," Pittsfield is surrounded by rolling hills, lush forests, and pristine lakes, making it an outdoor enthusiast’s paradise. Whether you enjoy hiking, biking, or simply soaking in the stunning vistas, this city offers ample opportunities to connect with nature.

Pittsfield boasts a vibrant downtown area filled with eclectic shops, delightful eateries, and cultural attractions. The historic Colonial Theatre hosts a variety of performances, from Broadway shows to local productions, ensuring that there’s always something exciting happening. Art lovers will appreciate the Berkshire Museum and the numerous galleries showcasing local talent.

The city is also home to several parks and recreational areas, including the beautiful Burbank Park and the serene Onota Lake, perfect for picnics, fishing, and family outings. For those who enjoy winter sports, nearby ski resorts offer thrilling slopes and cozy lodges.

Pittsfield is not just about natural beauty and culture; it’s also a community that values education and growth. The city is served by quality schools and institutions, making it an ideal place for families. With a strong sense of community and a welcoming atmosphere, Pittsfield is a place where neighbors become friends.

Whether you’re looking to buy a home, invest in property, or simply explore, Pittsfield offers an irresistible blend of charm, opportunity, and a lifestyle that many dream of. Discover the heart of the Berkshires and see why Pittsfield is the perfect place to call home!

Newest Listings in Pittsfield

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
60 Trillium Hill Rd, Pittsfield
$110,000
5115734 MLS
Discover the perfect setting for your Vermont getaway at 60 Trillium Hill Road in the picturesque town of Pittsfield. This 1.74-acre wooded parcel offers an excellent opportunity to build your dream home, vacation retreat, or year-round residence in the heart of the Green Mountains. Featuring a gently sloping landscape, a peaceful natural setting, and scenic mountain surroundings, the property provides an inviting canvas to bring your vision to life. With an approved three-bedroom wastewater permit already in place, an important step in the building process has been taken care of, allowing you to move forward with greater confidence. High-speed fiber-optic internet is available at the street, offering the convenience of modern connectivity while enjoying the tranquility of Vermont's countryside. Ideally situated near Killington and Pico Mountain, this location places you within easy reach of some of Vermont's most popular year-round recreational destinations. Golf enthusiasts will appreciate being just 12 minutes from Green Mountain National Golf Course, widely recognized as one of Vermont's top-rated public golf courses. Spend your winters skiing and snowboarding, enjoy a round of golf surrounded by breathtaking mountain scenery, or explore the area's extensive hiking and mountain biking trails during the warmer months. The surrounding region also offers charming local restaurants, shops, and opportunities to experience the quintessential Vermont lifestyle. Whether you envision a cozy mountain cabin, a contemporary retreat, or a comfortable year-round home, this property offers the space, setting, and flexibility to create something truly your own. Enjoy the privacy of a wooded lot without sacrificing access to the outdoor recreation and amenities of the Killington region. A wonderful opportunity to establish your own piece of Vermont in a location where adventure, relaxation, and natural beauty come together.

60 Trillium Hill Rd, 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
17 Manchester St, Pittsfield
$519,000
5112697 MLS
Priced below assessed value! Expand your investment portfolio with this 4-unit multifamily property at 17 Manchester Street in Pittsfield, NH. A great commuter location minutes from Route 28 adds rental appeal, while a varied unit mix - one 3-bedroom, two 2-bedroom, and one 1-bedroom apartment - offers flexibility for a range of rental needs. Three units are currently rented to long-term tenants, providing an established rental base. The fourth is owner occupied, offering a potential opportunity for an additional income-producing unit or a buyer looking to live on-site while collecting rent from the other apartments. Public water and sewer simplify utility management, and separate electric meters allow for individual electric billing. Heat is paid by the landlord. With established tenancy, a versatile unit mix, and a convenient location, this property is an appealing opportunity for investors seeking to grow their rental holdings or owner-occupants interested in building equity through multifamily ownership.

17 Manchester St, Pittsfield
1422 Upper City, Pittsfield
$149,900
5110385 MLS
Beautiful, level, open field land building lot. Presently sitting with two sheds on lot for personal property while building, this level lot is situated on scenic country road. Walking distance to apple orchard and or Over the Moon restaurant, this is a great residential location for new home. Open fields and stonewalls make for great building site.

1422 Upper City, 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
100 Hawk Trl, Pittsfield
$70,000
5108212 MLS
Rare opportunity to build in the desirable Hawk Mountain community on an unusually accessible, gently sloping parcel. Located between Hawk Mountain Road and Hawk Trail, this lot is one of only a handful in the community that avoids the steep, challenging terrain typical of mountain properties. The favorable topography can simplify site work, driveway construction and the eventual building process - an important advantage for anyone planning a Vermont getaway. Even better, a State-issued WW permit is already in place for a three-bedroom residence, providing a valuable head start toward development. Architectural review and protective covenants help preserve the distinctive character and quality of life that make this small mountain community so appealing. Outdoor recreation is right at your doorstep, with the Green Mountain National Forest just one mile away for hiking, mountain biking, snowshoeing and access to the VAST snowmobile trail network. Killington and Pico ski resorts are also just a short drive away, offering some of Vermont's best skiing and riding. With its combination of gentle terrain, permitted three-bedroom wastewater system and exceptional location, this is a rare chance to build your own Vermont mountain retreat on one of the community's most accessible building sites. Bring your plans and make it your own!

100 Hawk Trl, 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
15 Leavitt Rd, Pittsfield
$449,000
5107423 MLS
Great investment opportunity in the heart of Pittsfield! This historic multi-family property, originally built in 1850, offers character, flexibility, and excellent potential for an investor or owner-occupant. Each unit features its own kitchen and living area, along with two bedrooms and a full and a 1/2 bath, plus air conditioning, providing comfortable and functional layouts for tenants or extended family. Recent updates include mini-split systems, offering added peace of mind and energy-efficient heating and cooling. With its historic character, versatile floor plan, and two-bedroom units, this property presents an excellent opportunity to build equity and generate rental income. Zoned Commercial/Light Industrial, you could also use the property for another use with high visibility. Whether you’re expanding your investment portfolio or looking for a property with income potential, this Pittsfield multi-family is worth a look!

15 Leavitt Rd, Pittsfield
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