Pittsfield Homes under $1 million

Welcome to Pittsfield, a charming city nestled in the heart of the Berkshires, Massachusetts. Known for its rich history, vibrant arts scene, and breathtaking natural landscapes, Pittsfield offers a unique blend of small-town charm and urban convenience. With the stunning backdrop of the Berkshire Mountains, residents enjoy an array of outdoor activities, from hiking and skiing to fishing and boating on the nearby lakes.

Pittsfield is not only a cultural hub, boasting theaters, galleries, and annual festivals, but it also prides itself on its welcoming community spirit. The city's downtown area features an eclectic mix of shops, restaurants, and cafes, making it a perfect spot for leisurely strolls and social gatherings. Families will appreciate the excellent educational institutions, parks, and recreational facilities that cater to all ages.

For those looking to invest in the Pittsfield real estate market, you'll be pleased to discover a variety of homes available for under $1 million. Whether you're seeking a cozy bungalow, a spacious family home, or a charming historic property, Pittsfield has something to suit every taste and budget. Many of these homes are set in picturesque neighborhoods, offering peace and tranquility while still being within reach of the city's vibrant amenities.

With its affordable housing options, stunning surroundings, and a community that feels like family, Pittsfield is an ideal place to call home. Explore the possibilities today and discover why so many are choosing to make this beautiful city their own!

Newest Pittsfield Homes under $1 million

$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

$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

$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

$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

$745,000

3 Beds ⋅ 2 Baths ⋅ 5097001 MLS

Tucked away at the end of Upper Michigan Road on 54.4 private acres bordering the Green Mountain National Forest, this remarkable 1825 Vermont farmhouse offers breathtaking long-range mountain views in an unforgettable setting. Rich in authentic character, the home showcases rustic knotty pine walls, exposed hand-hewn beams, wide plank floors, and a fieldstone fireplace hearth. The home's low ceilings and gently uneven floors are not imperfections — they are reminders of a time when homes were built by hand and meant to last. A thoughtfully designed addition in 1996 blends seamlessly with the original home, providing modern comfort with a spacious primary bedroom featuring 10-foot ceilings and custom built-ins, a guest bedroom, and a beautifully updated full bath. The expansive living area offers inviting spaces to gather around the woodstove, enjoy movie nights, or relax with family and friends. The vintage-inspired kitchen and dining area, with vaulted ceilings, warm pine finishes, and a picnic-style dining table, is ideal for casual entertaining. Upstairs, two additional guest bedrooms and a powder room provide comfortable accommodations. Outside, more than 30 acres of managed woodland extend along both sides of the town road, complemented by open lawns, mature perennial gardens, and endless opportunities to enjoy the spectacular southern views. A detached two-car garage with overhead storage provides ample space for vehicles and outdoor gear. Snowmobiling, ATV riding, hiking, mountain biking, and snowshoeing are all accessible directly from the property. A state wastewater permit for an additional three-bedroom home offers exceptional flexibility for future expansion or a family compound. This is a rare opportunity to own a legacy Vermont property where history, privacy, recreation, and extraordinary natural beauty come together.

2238 Upper Michigan, Pittsfield

$599,900

3 Beds ⋅ 1 Baths ⋅ 5094594 MLS

A distinctive Vermont log home with space, privacy, and year-round versatility just 15 minutes from Killington. Set on 1.3 wooded acres in Pittsfield, this 3 bedroom, 1-bath home centers around a dramatic great room with cathedral ceilings, exposed beams, warm wood interiors, and a wood stove. A natural gathering space after a day on the mountain or simply at the end of the day. Thoughtfully expanded with a 1998 addition and well maintained over the years, the home offers an oversized heated two-car garage, standing-seam roof, EC Fiber high-speed internet, generator hookup, central vacuum, and Efficiency Vermont insulation improvements. These are the practical features that make Vermont living easier in every season. Step outside to a covered porch or the expansive rear deck with retractable awning, with room for summer dinners, a quiet morning outdoors, or an evening surrounded by mature trees and seasonal mountain views. Established landscaping and lawn complement the privacy of the wooded 1.3 acre setting. The full walkout basement spans both sections of the home, adding substantial workshop, storage, and laundry space, rough plumbing for a future bath, and two walkout entrances. Skis, bikes, outdoor gear, projects and hobbies all have a place here. Four-season recreation is close at hand: approximately 15 minutes to Killington, 20 minutes to Pico, 10 minutes to Pittsfield Village, 30 minutes to Woodstock, and 35 minutes to Rutland. Whether home is where you spend every day or where you come to get away, this is a place with room to gather, work, unwind, and enjoy Vermont in every season.

221 Fiddlehead Ln, Pittsfield

$249,900

5093110 MLS

**BACK ON MARKET – Due to no fault of the seller.** Union Block – Historic Commercial Opportunity! Step into history with the iconic Union Block, a landmark commercial building built in 1895 and filled with potential. Situated in a prominent Main Street location, this versatile property presents an exceptional opportunity for investors, entrepreneurs, and business owners. The former Main Street Variety storefront has been updated and is ready for its next chapter. Currently set up for another convenience store, the space also offers excellent potential for a coffee shop, bakery, café, boutique retail shop, or other commercial venture. Recent improvements include updated finishes and efficient mini-split heating and cooling systems, making the storefront ready for immediate use. With its historic character, strong street presence, and flexible layout, Union Block could accommodate a variety of commercial, retail, office, mixed-use, or redevelopment concepts, subject to town approvals. While portions of the building will require rehabilitation and updating, the property offers a unique opportunity for value-add improvements while preserving a piece of local history. Whether you're looking to continue its retail legacy, pursue a redevelopment project, or create something entirely new, Union Block provides the foundation to bring your vision to life. Bring your ideas and unlock the potential of this historic Main Street property.

18-22 Main St, Pittsfield

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