Pittsfield Homes under $500,000

Welcome to Pittsfield, Massachusetts – a charming city nestled in the heart of the Berkshires, where vibrant culture meets stunning natural beauty. Known for its rich history, Pittsfield offers residents a unique blend of urban amenities and picturesque landscapes. With its bustling downtown area, you’ll find an array of shops, restaurants, and art galleries, making it a perfect spot for both leisure and entertainment. The city is also home to several parks and outdoor recreational areas, providing ample opportunities for hiking, biking, and enjoying the great outdoors.

For those seeking a home in this delightful city, you’ll be pleased to discover that Pittsfield boasts a variety of real estate options, particularly for buyers looking for homes under $500,000. Whether you're a first-time homebuyer, a growing family, or looking to downsize, Pittsfield offers an impressive selection of properties to suit your needs. From charming single-family homes with character to modern townhouses and cozy condos, there's something for everyone in this affordable market.

The community in Pittsfield is warm and welcoming, with a strong sense of pride and connection among its residents. Local events, farmers' markets, and seasonal festivals create a vibrant atmosphere that makes you feel right at home. With its affordable housing options and an abundance of amenities, Pittsfield is not just a place to live; it's a place to thrive. Come explore the possibilities and discover why so many are choosing to call Pittsfield home!

Newest Pittsfield Homes under $500,000

$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

$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

$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

$249,900

5093110 MLS

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 to bring their vision to life. The former Main Street Variety storefront has been updated and is ready for its next chapter. Currently set it 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 this storefront space ready for immediate use. With its historic character, strong street presence, and flexible layout, Union Block can 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 tremendous potential for redevelopment and value-add improvements. This is an ideal opportunity for someone looking to restore and revitalize a historic Main Street property while building equity and preserving a piece of local history. Whether you're looking to continue its retail legacy or create something entirely new, Union Block provides the foundation to make your vision a reality. Bring your ideas and unlock the potential of this historic Main Street gem.

18-22 Main St, Pittsfield

$250,000

5088311 MLS

DEALS! 3 parcel package for just under 250,000. The 3 parcels includes a massive 8300+ sf building and a separately deeded buildable .28 acre parcel(combined lot 5&6). The building once functioned as a popular pizza restaurant, which still has all the expensive restaurant equipment still in place including multiple fridges, pizza ovens, burners, etc. The first floor includes a residential owners unit in the back, and also a separate commercial unit, perfect for another retail/restaurant or office use. The 2nd & third floor is in need of work but offers ~5000 square feet of space, perfect for ~9+/- apartments, bringing the total potential unit count over 12.Parking is required for the potential unit conversions, where the adjacent lot offers approximately 30 parking spaces. Alternatively, the second lot is buildable and meets the required lot size and setback requirements set by the town. This property requires a lot of work, and buyers are responsible for conducting their own due diligence regarding all building requirements, permitted uses, restaurant equipment and potential expansion opportunities. This property and parcels can be purchased as a package with MLS#5088125. PRIVATE SHOWINGS friday 4-6PM & Saturday 1-3PM.

27 Carroll St, Pittsfield

$479,900

5088125 MLS

Investors, look no further for a deal of a lifetime. This large 5-unit property offers 6,769 SF of finished space with a cap rate exceeding 13.5%, along with potential for additional units through subdivision of the commercial spaces or expansion of the existing layouts. A current storage area also presents the opportunity for conversion into an additional unit. The interior residential units are well maintained with solid long term tenants. In the past 3 years, the largest unit has been updated throughout, featuring a renovated kitchen with beautiful granite countertops, stainless steel appliances, and newer flooring. The bathrooms have also been remodeled with updated tubs and vanities. The smaller one-bedroom unit offers a cozy layout and has seen updates as well, including new carpeting, along with improvements to the kitchen and bathroom. The property’s large footprint offers the potential for 6+ additional residential units through conversion of the commercial spaces, along with the possibility of 5+ more units in the unfinished attic — creating the opportunity for an intriguing combined 15+ unit building. Parking would be needed as required by the town for the increased units but that can be fulfilled with the sale of the property across the street that can be purchased as a package (MLS # 5088311). Other updates include a young roof and a young highly efficient Buderus boiler. Located in the heart of downtown Pittsfield, tenants enjoy walkable access to shops, restaurants, and everyday conveniences in a true small-town setting. Nearby Drake Field offers outdoor recreation along the Suncook River with trails, fields, and courts. Commuting is also convenient, with Concord under 30 minutes away and Boston & Portsmouth less than an hour. PRIVATE SHOWINGS Friday 4-6PM and Saturday 1-3PM.

2 Depot St, Pittsfield

Start Your Search

board logo Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .