Pittsfield Homes under $750,000

Welcome to Pittsfield, Massachusetts—a charming city nestled in the heart of the Berkshires, where stunning natural beauty meets vibrant community life. Known for its rich history, Pittsfield offers a unique blend of cultural attractions, outdoor adventures, and a welcoming atmosphere. With its picturesque landscapes, residents can enjoy hiking, biking, and skiing, all within a stone's throw from home. The city boasts a thriving arts scene, highlighted by the renowned Barrington Stage Company and the Berkshire Museum, making it a cultural hub for both locals and visitors.

For those considering a move to this delightful city, Pittsfield presents an array of homes priced under $750,000, making it an attractive option for families, first-time buyers, and anyone looking to invest in a charming community. From cozy single-family homes to modern townhouses, the real estate market here offers something for everyone. Many properties feature spacious yards, perfect for outdoor gatherings, and are conveniently located near schools, parks, and shopping areas.

Living in Pittsfield means embracing a lifestyle rich in community spirit and natural beauty. The city's friendly neighborhoods foster a sense of belonging, where neighbors become friends and local events bring everyone together. Whether you're drawn to the tranquility of the Berkshires or the vibrant cultural scene, Pittsfield is a place where you can truly feel at home. Explore our listings today and discover the perfect property that fits your lifestyle and budget in this enchanting city!

Newest Pittsfield Homes under $750,000

$340,000

2 Beds ⋅ 1 Baths ⋅ 5108433 MLS

Price Drop $50,000 Motivated seller wishes for a fast close. Character, privacy, and room to grow, all on 3 acres. This split-entry home offers 1,370 square feet of finished living space above grade, with comfortable single-level living and a full lower level waiting for your vision. It's a blank canvas ready to become whatever you need most: a family room, home office, gym, workshop, or additional living space. Buy the home that fits you now, and let it grow as your plans do. Outside is where the property truly sets itself apart. A custom-built gazebo sits beside the home, its stained-glass windows casting color across a space made for morning coffee, evening gatherings, or a quiet hour with a book. Beyond it, you'll find a collection of additional buildings and structures created by the previous owner as places to relax and enjoy the outdoors. Together they give these grounds a personality you won't find on a typical lot, and leave the next owner plenty of room to reimagine them. With roughly 300 feet of road frontage and three full acres to spread out on, there's space for gardens, pets, projects, or simply quiet. And you're still minutes from downtown Pittsfield with convenient access to Concord, Manchester, and the Lakes Region. An approachable entry point, real land, and a lower level full of possibility; 360 Dowboro Road is a rare chance to own something with genuine character and make it your own. Schedule your showing and come see what this one could become.

360 Dowboro Rd, 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. Join us for the open houses: Friday, 9/4 | 6–8 PM Saturday, 9/5 | 10 AM–12 PM

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

$300,000

3 Beds ⋅ 2 Baths ⋅ 5106738 MLS

Under contract but will continue to show. 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!

28 S Main 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

$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

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