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

$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

$300,000

3 Beds ⋅ 2 Baths ⋅ 5106738 MLS

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! Showings begin at the Open House on Saturday, August 29, and Sunday, August 30, from 10:00 AM–12:00 PM.

28 S Main St, Pittsfield

$319,900

2 Beds ⋅ 2 Baths ⋅ 5106327 MLS

BRAND NEW AND AFFORDABLE HOME! Keep your costs low and comfort level high! Two bedroom, two bath, single family residence on its own land, just finished. Super efficient Bosch heat pump with LP Gas assist and whole house AC. Fully applianced eat-in kitchen has fridge, electric range, microwave, and dishwasher. Upstairs full bath has stacked LG washer/dryer. Fully foam insulated for heat/cooling savings and noise cancellation. Situated on a small in-town lot within walking distance of all village amenities has municipal water and sewer. Parking for up to 5 cars.

4 Marshall Ct, Pittsfield

$274,900

3 Beds ⋅ 1 Baths ⋅ 5105952 MLS

Discover the perfect blend of country living and commuter convenience! This well-maintained three-bedroom, one-bath home is situated on 2.83 acres. Newer updates/features include new drilled well, flooring, and generator hookup. Offering plenty of space for gardening, farm animals, or a small working farm. While Enjoying the peaceful rural setting this property is a great commuter location approximately 20 minutes from Concord, 45 minutes from Manchester, and 60 minutes from Portsmouth. Whether you’re dreaming of a homestead, hobby farm, or simply more room to enjoy the outdoors, this versatile property offers a wonderful opportunity to make that vision a reality. Offer deadline has been set for Tuesday 8/25/2026 at 12:00pm.

35 Thompson Rd, Pittsfield

$424,900

2 Beds ⋅ 1 Baths ⋅ 5105849 MLS

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

$499,000

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

3 bedroom 1 bath 1991 Redman Mobile home on 1 acre in a private setting. Home has a new 2023 Forced Hot air heating system. Electric hot water heater was replaced in 2021. Interior of home cannot be viewed due to tenant.

251 Webster Mills Rd, Pittsfield

$695,000

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

$450,000

3 Beds ⋅ 2 Baths ⋅ 5101870 MLS

Rare opportunity! This well-maintained ranch has been owned by the same family for over 60 years and is located in Pittsfield's Light Industrial/Commercial District. The property offers exceptional flexibility for entrepreneurs, contractors or buyers seeking a live/work opportunity. Whether you are looking for a primary residence with business potential or a property with future commercial possibilities, this property offers you all of that! 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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