Pittsfield Real Estate

Welcome to Pittsfield, Massachusetts, a charming city nestled in the heart of the Berkshires. Known for its rich history, vibrant arts scene, and stunning natural landscapes, Pittsfield is a hidden gem that offers a unique blend of small-town charm and urban amenities.

Founded in 1761, Pittsfield boasts a rich cultural heritage that is reflected in its historic architecture and community events. The city is home to a variety of museums, including the Berkshire Museum, which showcases art, history, and natural science exhibits. For those who appreciate the performing arts, the renowned Barrington Stage Company and the Colonial Theatre offer an array of performances throughout the year, drawing visitors from near and far.

Nature enthusiasts will find plenty to love in Pittsfield, with easy access to the stunning outdoors. The nearby Berkshire Mountains provide a picturesque backdrop for hiking, skiing, and exploring. Parks such as Burbank Park and Springside Park offer serene spots for picnics, walking trails, and recreational activities, making it easy to embrace the beauty of the four seasons.

Pittsfield’s diverse dining scene caters to all tastes, from cozy cafes to gourmet restaurants, ensuring you’ll never run out of options to satisfy your culinary cravings. The city also hosts various farmers' markets and festivals, fostering a strong sense of community and local pride.

Whether you’re looking to relocate, invest, or simply explore, Pittsfield invites you to experience its welcoming spirit and vibrant lifestyle. Discover the perfect blend of history, culture, and natural beauty in this delightful city!

Newest Listings in 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

$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

$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

$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

$524,900

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.

7 True 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

$1,125,000

5106833 MLS

Excellent opportunity to add a 9-unit residential property to your investment portfolio! Tucked away on a quiet side street just minutes from downtown Pittsfield, this property offers a desirable combination of location, unit mix and off-street parking. The building consists of 5 studio apartments, 3 one-bedroom units and 1 two-bedroom unit, providing a diversified rental mix with broad tenant appeal. A major benefit for investors is that tenants pay their own heat, helping to reduce owner-paid operating expenses. Additional highlights include town water and sewer, newer heating systems and a newer roof, offering added value and peace of mind for the next owner. The property also offers plenty of off-street parking, a valuable amenity, as well as a large private backyard for tenants to enjoy. Conveniently located near downtown amenities and shopping while still enjoying the quieter setting of a side street. Whether you're looking to expand an existing portfolio or add a substantial multifamily asset, this property offers an attractive opportunity with 9 income-producing units under one roof. ***Also available as part of a larger off-market investment portfolio. Additional properties and portfolio information available upon request.***

7 Crescent St, 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

$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

$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

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