775 houses for sale in Housatonic

Bring your vision and creativity to this spacious side-by-side duplex that's been stripped down and prepped for its next chapter. Much of the heavy lifting has already been completed, including extensive demolition work and rough electrical installation. The exterior has also received a 1st of coat of paint. Originally intended to be converted into townhouses and sold separately, the owner's plans have changed, creating an exciting opportunity to customize a property to their needs. One unit offers 4 bedrooms and 1.5 baths, while the second features 3 bedrooms and 1.5 baths. Both units include private enclosed front porches, open rear porches, and spacious layouts ready to be transformed. The walkout basement opens to the backyard and offers additional possibilities. Whether you're looking to create income-producing rentals, pursue a townhouse conversion, or design your dream multi-generational property, this diamond in the rough is packed with potential

Modern elegance meets turnkey peace of mind in this fully reimagined Sheffield retreat. Set on 2.3 level acres, this 3BR, 3.5BA sanctuary spans 2,748 square feet across three finished levels. The sun-drenched main floor features wide-plank white oak floors, a gas fireplace, a large half bath, a chef's kitchen with stainless appliances, white quartz counters, and seamless access to a wrap-around deck. Upstairs, a treehouse-like loft adds charm, while the primary suite delivers a spa-like experience. The three suites were designed for intimacy and privacy. The walk-out lower level houses a guest suite and fantastic game room. Renovated top-to-bottom with no expense spared, central A/C, and new mechanicals-just bring your suitcase. 15 mins to Guido's and 45 mins to the Wassaic NYC train

Great New Price! Discover the timeless charm of this beautiful turn-of-the-century Victorian, showcasing the craftsmanship and character of its era. Inside, you'll find impressive 9-foot ceilings, detailed crown molding, beautiful hardwood floors, and charming built-ins that highlight its classic architectural beauty. Spacious, sun-filled rooms offer plenty of room for entertaining, relaxing, and everyday living. Recent updates, including a newer furnace, windows, and roof, add to the home's appeal while preserving its distinctive character. Tucked away in a peaceful setting yet conveniently located close to downtown, this generously sized home offers the perfect blend of historic charm, everyday comfort, and endless possibilities for its next owner!

Well-located home nestled in a desirable neighborhood with convenient access to local amenities, schools, and outdoor recreation. This inviting property offers a comfortable layout designed for everyday living and entertaining, featuring bright, sun-filled spaces and a warm, welcoming atmosphere throughout. The home provides a functional flow with generously sized living areas, a thoughtfully designed kitchen, and ample room to accommodate a variety of lifestyles. Bedrooms offer comfortable retreats, while additional space allows for a home office, guest area, or flex use to suit your needs. Enjoy the benefits of a private yard and deck, ideal for relaxing, gardening, or hosting gatherings. Whether you are a first-time buyer, downsizing, or looking for a Ber

The building has the potential to be a great income producing property. There are 4 units with plenty of off street parking. It has vinyl siding, replacement windows and is close to the downtown area. 3 Units are lead safe. Check the documents section referencing a letter from the City Commissioner. The owner is in the process of having plans drawn by a local architect firm to address the scope of the work

Two-family flat offering strong potential for investors or owner-occupants seeking rental income. Located close to town, this property features a 3-bedroom, 1 bath first-floor unit with a de-lead certificate that will soon be vacant and a 2-bedroom 1-bath second-floor unit that has been de-leaded but has no certificate and is currently on a month-to-month lease. An enclosed front porch adds charm and additional usable space, while the small yard keeps exterior maintenance manageable. Updates include a new roof in 2022, some vinyl replacement windows, updated plumbing and a new auto-fill system added to the boiler along with additional radiators in 2025. With solid income potential this property offers a practical opportunity for buyers looking for a multi-family investment

A rare opportunity to acquire two neighboring properties, offered together on separate lots, in a desirable Pittsfield neighborhood. The former Pilgrim Holiness Church presents a distinctive space filled with character and exciting possibilities for adaptive reuse, creative pursuits, community-oriented activities, or future redevelopment. Next door, the former rectory is a well-maintained Cape offering comfortable living space and the potential for rental income, an owner's residence or on-site accommodations. Together, these properties create a compelling investment package with flexibility rarely found in a single offering. The separate lots add versatility for future ownership, use, or development strategies, subject to applicable zoning and municipal approvals. Whether envisioned as a live-and-work arrangement, an income-producing investment or a thoughtfully reimagined property, this unique Elm Street offering provides an outstanding foundation in a convenient and established Pitt

Well-maintained seven-unit investment property in a convenient Southeast Pittsfield location. This handsome brick building features spacious apartments, classic architectural character and practical layouts. Six units offer two bedrooms and one bathroom, while the additional basement-level apartment includes one bedroom and one bathroom that needs remodeling. Each unit features a fireplace mantel, rear porch with both interior and exterior access, along with a flexible front room that can be opened to the dining room. Additional improvements and amenities include replacement windows, on-site laundry, private off-street parking, individual basement storage areas for each apartment and a rear interior egress staircase serving all units. Heat and hot water are included in the rents. Conveniently located near shopping, dining, downtown Pittsfield and area amenities, this substantial multifamily property offers seven residential units under one roof and the timeless appeal of brick construc

Looking for one level living' Must see ranch in the southeast. This Polo Acres updated home is just over the Lenox line and close to all the Berkshires have to offer. Enter from the covered porch into a spacious welcoming entry. The light-filled living room with fireplace and gleaming wood floors flows into the dining area and three-season sunroom with awning. The large kitchen opens to a flagstone patio for outdoor dining and BBQs. First-floor laundry adds convenience. Primary suite with full bath/walk-in shower plus two additional bedrooms and a second full bath. Enjoy the partially fenced yard, oversized two-car garage, and full basement with a 2nd fireplace and large windows offering the potential for future living or recreation space

Mixed use property located just 7 miles south of Gt Barrington on Route 7. Two commercial units and two residential units. Solar on roof and in back of property bring in additional lease revenue. Long term tenants in each apartment. Anchor commercial tenant, Berkshire Fence and Accessories, to sign long term lease with new owner. Second commercial unit vacant, perfect for owner occupied buyer

Just 3 miles from Tanglewood and moments from the heart of Lenox, this 36+ acre estate offers rare scale, privacy, and flexibility in one of the Berkshires' most sought-after settings. A long, tree-lined driveway creates a strong sense of arrival, unfolding into two separate residences surrounded by woods, open land, and long-range possibility. The acreage offers both seclusion and the ability to selectively open views toward October Mountain State Forest. The main residence is thoughtfully configured for multi-generational living. The first floor centers around a large living and dining room anchored by an oversized stone fireplace, an eat-in kitchen with oak cabinetry and granite counters, and multiple access points to the outdoors. A heated sunroom and screened porch extend the living experience across seasons. The primary suite includes an en-suite bath, and this level is further enhanced by a second kitchen and laundry hookups, creating true independence within the home. The secon

Enjoy the perfect blend of space, privacy, and convenience in this 5-bedroom, 2-full-bath home offering 2,252 square feet of living space on 5.9 acres in Pittsfield. The first floor kitchen features granite countertops, fireplace in the living room, three bedrooms and full bath. The additional lower-level living space fireplace in 2nd living room, kitchen, mudroom, 2 bedrooms, and full bath offers excellent flexibility for extended family, guests, or a private retreat, complete with a separate entrance if needed. Conveniently located in Pittsfield, the property offers a wonderful sense of seclusion and privacy, surrounded by nature. With generous living space and plenty of room to enjoy the outdoors, this property offers a unique opportunity to create your ideal home!

Dreamy river Colonial: tucked away on 4 beautiful acres, 1361 feet of river frontage, offering privacy and a quiet sanctuary for wildlife viewing. Main floor features an updated classic chef's kitchen that flows into a spacious Great Room w/ wood-burning fireplace, dining area, 1/2 bath, and direct access to the sun deck with sparkling river and dramatic sunset views. A breezeway connecting the 2-car garage is a sunny space for all of your seasonal gear. Upstairs, the large primary bedroom includes a 2nd wood-burning fireplace and en suite bath, while two additional bedrooms share a full bath. Main floor office and a finished lower level currently serves as guest accommodations, media room, fitness, laundry, and a variety of additional uses. New landscaping! 4 bed Title V, completed 4/26

Beautiful and energy efficient, these are two great features of this home. In 2023 the owners had the property insulated through the MassSave program, and also had solar panels installed. The home offers a great floor plan! First, you will be welcomed by a mudroom that has tile floors, leading to an open floor plan consisting of living room, dining and kitchen with island. This area has glass doors to the side yard. The first floor also offers a renovated bathroom and large primary bedroom. Upstairs you will find to additional spacious bedrooms. The basement is partially finished with bonus rooms. On the back of the home there is a recently replaced deck off the kitchen, bringing you to the partially fenced-in backyard. A shed is also being included! All in a great southeast location, within walking distance to restaurants, pharmacies, businesses, the Elm Street Shops plaza and more!

Prime Downtown Great Barrington Gem - Endless Possibilities! Welcome to 406 Main Street, a rare opportunity in the heart of downtown Great Barrington, MA. Just steps from bustling Main Street shops and restaurants, this versatile 5,180 sq ft building offers exceptional potential for residential, commercial, or creative mixed-use transformation. Zoned B2, the property allows for single-family, multi-unit, or live/work conversion-with no sprinkler system required for up to 3 residential units. Already equipped with 1 full bath and 4 powder rooms, and featuring two finished floors, the layout adapts effortlessly to your vision-be it modern apartments, stylish offices, retail space, or a dynamic studio. - Spacious and bright with 5,180 sq ft across two levels - Excellent bone

Welcome to 12 Mountain St, a quintessential colonial masterpiece that blends classic elegance with modern functionality. Spanning over three expansive, light-filled floors, this stunning home offers five spacious bedrooms and 3.5 bathrooms, providing the ideal layout for those who love to entertain. The chef's kitchen is designed to inspire with high-end finishes, including a vast center island, a professional-grade Six-burner gas stove w/pot filler, chic quartz countertops. With an abundance of cabinetry and a dedicated, organized pantry featuring custom built-ins, this kitchen is as practical as it is beautiful. Gleaming hardwood floors flow throughout the main level, creating a seamless, inviting atmosphere. Ascend to the second floor, where you will find a tranquil primary en suite wit spa shower alongside two additional bedrooms connected by a well-appointed Jack-and-Jill bath. The third floor offers incredible flexibility with two more large, sun-drenched bedrooms and a dedicated

STILL HOUSE brings a new level of contemporary design to the Berkshires-quietly luxurious, exquisitely detailed, and made to be lived in. Minutes from the center of Great Barrington, this newly completed 5,148-square-foot home pairs the distinctive vision of acclaimed Brooklyn studio Me and General Design with exceptional craftsmanship and materials throughout. Four bedrooms, five-and-a-half baths, a heated saltwater pool, bespoke spa and fitness spaces, solar energy and exceptional privacy make this as much a retreat as a home.Preserved stone walls from the original structure bring history, texture and a distinctly Berkshire character to the new architecture. The main living level opens into a dramatic kitchen, dining and living space with cathedral ceilings, two stories of glass and views into the surrounding landscape. The custom Porcelanosa kitchen features richly veined stone, a substantial island, induction cooking, double ovens, integrated refrigeration, microwave drawer, dedica

Rare opportunity to own a beautifully restored Berkshire cottage at 17 Main Street, perfectly situated in the vibrant heart of downtown Lenox. This remarkable property, originally built in 1883 and once the residence of Gilded Age shipping magnate John Schermerhorn, combines historic elegance with modern comfort. The home underwent a comprehensive renovation between 2021 and 2025, including a new 30-year roof, upgraded electrical and plumbing, 8.5 renovated bathrooms, custom millwork, and restored original hardwood floors. The gourmet kitchen features a Viking 8-burner oven, KitchenAid designer dishwasher, and commercial-grade refrigeration-ideal for private entertaining or everyday living. All systems are new, including a four-zone HVAC and seven mini-splits for year-round comfort. With eight bedrooms (plus potential for a ninth), five fireplaces with new gas log sets, and inviting communal spaces, this home offers in-town living at its best. Enjoy the ultimate walk-to-everything life

Ghent Center is a well-positioned and handsome commercial investment property located along State Route 66 in the heart of the hamlet of Ghent, just minutes from Chatham and approximately 15 minutes from the City of Hudson. The brick building is perfect as a live / work artist space. With more than 460 feet of road frontage, excellent visibility, and an 8 Cap Rate, the property offers immediate cash flow with substantial long-term upside

Recently renovated colonial home with detached garage, located on a corner lot in a desirable Pittsfield location! This property features 3 enclosed porches, one on the front and the two others on left and right side of the home. There is great yard space! In the first floor you will be welcomes by a foyer leading to the living room. The dining room opens to one of the porches! The renovated kitchen features new cabinets, appliances and quartz countertops. There is also a convening first floor bathroom with shower. Upstairs you will find 3 bedrooms and another tastefully renovated bathroom with tub. There are laundry hookups in the first and second floor, your choice! Other improvements include a new roof, newer vinyl replacement windows and interior/exterior paint. The basement offers great storage space. Come see your new Berkshires home!

Opportunity to complete this renovation. Extensive site work has already been completed. $25,000 of Tree removal in 2022, kerosene tank removal in 2022, New Septic system designed and installed in 2023, Asbestos Remediation in 2025, New roof with new 3/4 plywood board in 2025, Installed 3 new remote controlled skylights in 2025, 3 more trees removed in 2025, U-driveway installed in 2025. Deeded Lake Rights and private beach for Owners Only. House is directly across from the path to the beach. Goose Pond is noted to be one of the cleanest lakes in Massachusetts. Finish this renovation or add a foundation of build your dream home in this highly sought after Lake Community

Move-in ready and filled with upgrades, this southeast Pittsfield colonial home offers five bedrooms and flexible living space. The first floor includes a bedroom and full bath, while the second floor features a primary ensuite plus three additional spacious bedrooms. Enjoy a beautifully landscaped, very private backyard with an above-ground pool and convenient access from the kitchen deck-perfect for summer entertaining. The finished basement recreation room w/660 sq.ft. is included in total sq.ft. Centrally located, the home is approximately 10 minutes from major shopping centers and less than 10 minutes to Lenox center and Tanglewood

Your private Berkshire retreat! Sweeping views of Squaw Peak, surrounding mountains, 42 beautiful sub-dividable acres with trails, seasonal brook, room for pool, tennis court, family compound. Warm, welcoming 4BR, 4.5 bath, home with room for family, friends, gathering or quiet escapes. Sun-filled fireplaced LR with picture window, cozy window seat framing the view; elegant formal DR with window wall and fireplace. Spacious chef's kitchen with island, dining area, TV area, comfy wood stove, leading to the large screened porch and expansive deck-perfect for morning coffee, summer dinners or simply relaxing. 3 main-level BRs include ensuite primary. Above-grade LL offers office, 4th BR, bath, inviting fireplaced family room. 2-car garage. 1 mile to downtown Great Barrington

Stunning and beautifully designed three-level end unit condominium with luxury finishes throughout. Enter into an open-concept main level, highlighted by gleaming hardwood floors, recessed lighting, and expansive windows that flood the space with natural light. The kitchen offers stainless steel appliances, granite countertops, and custom cabinetry. The spacious living and dining areas are perfect for entertaining, with easy access to a private screened in porch. Primary bedroom with en suite offers one level living if desired along with a walk-in closet with ample storage. Upper level includes oversized entry room that allows for a wide-range of functionality. Two additional bedrooms with large closets and a full bathroom. Finishing off in the lower level is a tremendous family room with a kitchenette and walkout to the back yard. An additional bedroom, full bathroom, and room for storage. Don't miss the opportunity to own this exceptional, move-in-ready condo. Schedule your private t

Meticulously maintained and lovingly cared for, this spacious four-bedroom, two-and-a-half-bath home offers the perfect combination of comfort, quality, and location. Featuring generously sized rooms throughout, this home provides ample space for both everyday living and entertaining. Pristine wood floors lie beneath the carpeting, offering the opportunity to uncover their timeless beauty. Recent improvements, including a new roof, providing peace of mind, while gas heat and central air conditioning ensure year-round comfort. Set in one of the area's most desirable neighborhoods and within a highly sought after school district, this property offers a truly special connection to its surroundings. The beautiful brook that flows through the backyard is the very feature for which Brookside Drive was named, creating a picturesque and tranquil setting that enhances the home's appeal. Enjoy the soothing sounds and natural beauty of the brook from your own backyard while appreciating the conve

Discover the potential of 23 Marcella Ave in Pittsfield, MA. This vacant property offers an opportunity to create a home, investment property, or future development project in the heart of the Berkshires. Conveniently located in Pittsfield, the property provides access to local shopping, dining, recreation, schools, and area attractions. Whether you're looking to build, invest, or secure land in Western Massachusetts, this property is ready for your vision. Buyers are encouraged to conduct their own due diligence regarding zoning, permitted uses, utilities, access, and all applicable town requirements

Attention Investors and Portfolio Builders! Exceptional turn-key opportunity to acquire a high-yield, fully leased 2-family home in Pittsfield. Built in 1880, this solid Colonial-style income-producer delivers an ideal layout optimized for low landlord overhead and immediate, stable cash flow from day one. A standout feature of this asset is the entirely separate utility infrastructure, substantially lowering your operational expenses. The downstairs unit (Unit 1) features a comfortable 5-room, 2-bedroom, 1-bathroom unit. The sprawling upstairs unit (Unit 2) offers a spacious 6-room configuration, including 2 traditional bedrooms plus a flexible bonus room-perfect as a 3rd bedroom or home office-complete with its own dedicated in-unit laundry room. With separate meters in place, the tenants handle their own primary utility bills, keeping your net operating income predictable and protected. Both units are used as 3 Bedroom units. The property sits on a low-maintenance 2,613 sq. ft. lot

Ideally located in the Downtown Arts District just off South Street, this two-family property offers an excellent investment opportunity. Fully renovated in 2007, the property features a total of 6 bedrooms and 2 1/2 bathrooms, with separate utilities for each apartment, paid by the respective tenants.The first-floor apartment offers 3 bedrooms, 1 1/2 bathrooms, and numerous updates throughout. The second-floor apartment features 3 bedrooms and 1 full bathroom, providing comfortable and functional living space.The property is serviced by public water and sewer and is equipped with two electric meters, two boilers, and two hot water heaters. Both apartments are heated with natural gas, with natural gas hot water as well. Conveniently located near Berkshire Medical Center, Berkshire Museum, The Colonial Theatre, Barrington Stage, schools, restaurants, shopping, and downtown attractions. Zoned business and residential, this property offers excellent investment potential in a convenient do

Located in one of Southeast Pittsfield's most sought-after neighborhoods, this well maintained home offers a versatile layout, great natural light, and comfortable living spaces designed to fit a variety of needs. The open living, dining, and kitchen area creates an easy flow for everyday living and entertaining, while two first-floor bedrooms and a full bath provide the convenience of single-level living. A recently added sunroom brings in even more natural light and offers the perfect spot to relax and enjoy the changing seasons. A mudroom, laundry room and half bath just off the garage add everyday functionality. Upstairs, two additional bedrooms and a full bath provide plenty of room for family or guests, while the finished basement offers valuable bonus space for a playroom, home office, gym, or second living area. Set on a flat corner lot, this home combines a desirable location with a flexible floor plan and room to make it your own

Situated on highly desirable Mountain Drive, this expanded 3-bedroom, 2-bath Cape delivers classic Berkshire charm, thoughtful updates, and flexible living spaces. Step inside from the welcoming front porch into an inviting layout featuring hardwood floors and abundant natural light. The spacious living room is anchored by a wood-burning fireplace flanked by custom built-ins, flowing into the formal dining room and a tastefully remodeled kitchen. Enjoy year-round tranquility in the heated four-season sunroom or relax in the separate main-floor den featuring a cozy gas fireplace and sliders leading out to the rear deck. A generous first-floor bedroom, full bath, and dedicated laundry room offer effortless single-level living convenience. Upstairs, find a sprawling primary suite with a walk-in closet, a second sizable bedroom, and a fully renovated full bath. The lower level expands your entertaining footprint with a heated family/recreation room and workout space, alongside a large unfi