Berkshire County, MA Real Estate | Berkshire County, MA Single Family Homes for Sale

Charming Colonial on a dead-end street! This well-maintained 4-bedroom home offers plenty of living space and is situated on a spacious 0.80-acre lot. The home features a comfortable layout, full basement, and attached garage, along with plenty of outdoor space to enjoy. Conveniently located in Pittsfield, with easy access to local schools, shopping, dining, and other city amenities.

40 8th St., Pittsfield

$229,900

2 Beds ⋅ 2 Baths ⋅ 73573584 MLS

Escape the hustle and bustle and enjoy the beauty of the Berkshires! Located in the peaceful town of Savoy, this charming ranch offers 2 bedrooms, 1 full bath, and approximately 3 acres of land to enjoy. Features include hardwood floors, a cozy wood stove, full basement with walkout access, and a convenient one-car attached garage. A new septic system is currently being installed, providing added peace of mind for the next owner. Surrounded by nature yet just a short drive to the Berkshires' many attractions, dining, hiking, recreation, and cultural destinations. Whether you're looking for a year-round home, weekend getaway, or peaceful retreat, this property offers a wonderful opportunity to enjoy country living while still being close to all the area has to offer.

304 Chapel Rd, Savoy

$300,000

2 Beds ⋅ 1 Baths ⋅ 73572671 MLS

Welcome to 73 Melrose St in Adams! This charming 2-bedroom, 1-bath home offers 936 square feet of living space and sits on a generous lot with plenty of outdoor space. Built in 1958, the property offers a great opportunity for a buyer looking for a manageable home with room to enjoy the outdoors. Conveniently located close to downtown Adams, local shops, restaurants, and area amenities, while still offering a comfortable residential setting. With its spacious lot and convenient location, this property is a great opportunity for all! Please text listing agent for all showings.

73 Melrose St, Adams

$259,900

4 Beds ⋅ 2 Baths ⋅ 73571195 MLS

Move-in ready 4-bedroom, 1.5-bath home with a spacious barn! Pride of ownership shines throughout this beautifully maintained home. The first floor offers a welcoming living room, dining room, kitchen, one bedroom, and a convenient half bath. Upstairs features three additional bedrooms and a full bath. Enjoy your morning coffee on the front porch or relax in the private backyard accented by white vinyl fencing. The detached barn with electricity offers endless possibilities for garage parking, a workshop, hobby space, storage, or the ultimate man cave or she shed. Conveniently located within walking distance to downtown North Adams and Mass MoCA. This private oasis could be yours!

22 South Street, North Adams

$349,900

3 Beds ⋅ 2 Baths ⋅ 73569984 MLS

Recently renovated colonial home with detached garage, located on a corner lot in a desirable Pittsfield location! This property features a lovely front porch as well as a side porch and great yard! There are 3 bedrooms, however, the home could be used as a 4-bedroom. You will love the two updated full bathrooms, one on each floor! Other improvements include a new roof, newer vinyl replacement windows and interior/exterior paint.

100 Essex St, Pittsfield

$3,695,000

4 Beds ⋅ 6 Baths ⋅ 73568631 MLS

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 & 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, dedicated coffee station and breakfast nook. A separate stone-walled sitting room offers a restored wood-burning fireplace and a more intimate place to gather.The main-level primary suite makes true one-floor living possible, with direct deck access, a walk-in closet and private bath. Upstairs are two additional bedrooms and two full baths, plus a library/sitting area overlooking the great room. The light-filled lower level includes a private fourth bedroom suite, home cinema, office, yoga/Pilates studio, traditional Canadian red cedar sauna, full bath and laundry.High-efficiency multi-zone heat pumps, radiant lower-level heat and solar energy support year-round comfort. Outside, the heated saltwater pool is set against mature trees, with decks, paths, stonework and an outdoor fireplace creating places to gather throughout the seasons. Landscape design by Windy Hill Farm complements the natural setting.Lake Mansfield, Monument Mountain, Ski Butternut, Tanglewood, Jacob's Pillow and the restaurants, shops and cultural life of Great Barrington are all within easy reach.STILL HOUSE is the inaugural residence of NUESTRA Collection, a series of design-led Berkshire homes created around a simple idea: exceptional contemporary design should feel as good to live in as it is to look at.

114 Christian Hill Rd, Great Barrington

$109,900

3 Beds ⋅ 2 Baths ⋅ 73568450 MLS

167 Daniels, Pittsfield

$2,295,000

31 Beds ⋅ 29 Baths ⋅ 73567764 MLS

A singular opportunity to reimagine one of Lenox's historic Berkshire estates. Set on 11.90± acres just minutes from downtown Lenox and the cultural attractions of the Berkshires, Overlee was built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan/Jacobean Revival style.The original mansion remains at the heart of the property, surrounded by broad lawns and buildings added during its later evolution into an educational campus. Much of the character of the original country house remains, including handsome woodwork, substantial fireplaces, gracious rooms, and a beautiful ballroom. Most recently used for classrooms and administrative functions, the mansion was originally designed as a residence, with bedrooms on its upper floors.Beyond the main house are two dormitory residences with approximately 24 bedrooms and shared common spaces, a separate multi-level building with commercial kitchen and dining facilities, classrooms, offices, library, conference and infirmary spaces, a substantial gymnasium, and additional support buildings. For a residential buyer, this unusual collection offers possibilities for guest and staff accommodations, studios, offices, recreation, wellness, or a multi-generational Berkshire estate, subject to applicable approvals.The gymnasium could accommodate fitness, indoor tennis, pickleball, squash, or other private amenities. Existing infrastructure includes public water, multiple electrical services, mixed heating systems, central air in the dormitories and gymnasium, commercial sprinklering in select buildings, extensive parking, and established internal circulation.Hillcrest currently operates on the campus under a lease through June 2027 and presently anticipates vacating in February/March 2027.This offering is for 349 Old Stockbridge Road only. The property is also marketed as part of a combined offering with 40 Frothingham Crossing; see MLS #73518284.For its next steward, Overlee offers the rare chance to inherit not simply a house, but an entire Berkshire estate—historic architecture, expansive grounds, and a collection of buildings ready to support a new vision.Offered at $2,295,000.

349 Old Stockbridge Rd, Lenox

$180,000

4 Beds ⋅ 2 Baths ⋅ 73567609 MLS

Conveniently located near downtown Pittsfield, this home sits on .14 acres with a backyard for entertaining and garage for storage. The first floor offers a living room, dining room, kitchen, bathroom, and a flexible space with many possibilities. Upstairs are 3 bedrooms, a full bathroom, and a walk-up attic. The walk-out basement provides additional potential. Major updates include cellulose insulation and basement air sealing/weatherstripping (2017), new roof (2019), new furnace (2021), furnace cleaning (2025), and chimney reconstruction with stainless-steel liner (2025). Ideal for those looking to bring their own renovations and bring out this home's great potential. Property is being sold AS IS with all contents remaining.

39 Hull Ave, Pittsfield

$179,000

4 Beds ⋅ 2 Baths ⋅ 73566686 MLS

Opportunity awaits with this home offering approximately 1,493 square feet of living space on a generous 12,807 sq. ft. lot. This property presents a great starter-home opportunity with solid bones and plenty of potential for updates and personalization. The spacious lot provides ample room for outdoor enjoyment and future improvements. With some TLC, this home offers an excellent opportunity to bring your vision to life. Conveniently located near Pittsfield shopping, dining, schools, and local amenities.

23 Walnut St, Pittsfield

$349,900

3 Beds ⋅ 2 Baths ⋅ 73566643 MLS

Raised ranch with two-car garage, located on a double lot with almost half an acre of land. The main level features 3 bedrooms, full bathroom, living room and kitchen with dining area, with slider opening to deck which was recently painted. The finished lower level offers family room with sliders to the backyard. In addition to the hot water baseboard, this family room also features a pellet stove. In the ground level you will also find an additional bathroom with stand-up shower and washer/dryer. The bathroom has brand new flooring and sink! The lower lever also offers garage access plus an unheated bonus room last used as an office. The backyard is private and there is also a large shed! The home was built in 1995, it has natural gas heat and hot water, city water/sewer and a shed is included. There are two extra parking spaces a little up the street on the adjacent lot that is already being included with the house. *Floor plans available

225 Brown St, Pittsfield

$724,900

5 Beds ⋅ 4 Baths ⋅ 73564933 MLS

Tucked away on 3.24 private wooded acres, this one-of-a-kind Contemporary offers 3,744 sq. ft. of living space across three finished levels. Soaring ceilings, exposed timber beams, hardwood floors, and dramatic center chimney create a warm yet impressive setting. The open floor plan is anchored by multiple wood-burning fireplaces, a pellet stove, and abundant natural light. Offering a total of five bedrooms and 3.5 baths, including a private in-law suite above the oversized attached two-car garage, this home provides exceptional flexibility for guests or extended living. Enjoy an owned 9.52 kW solar system, spacious decks, beautifully maintained grounds, and the privacy of a true Berkshire retreat just a short drive from everything the Berkshires and Northampton have to offer.

255 High St Hill Rd, Windsor

$459,900

3 Beds ⋅ 2 Baths ⋅ 73564129 MLS

Enjoy the peace and privacy of approximately 14 acres in beautiful Becket. This 3 bedroom, 2 bath home features a long driveway, plenty of parking, trails throughout the property, a two-car garage, back deck, and storage shed. Recent updates include a newer roof, windows, and water heater. Conveniently located near Center Pond, Becket Town Beach, and Jacob’s Pillow.

177 Fred Snow Road, Becket

$879,000

3 Beds ⋅ 3 Baths ⋅ 73563529 MLS

Welcome home to an extraordinary blend of modern style, flexible living, and resort-quality outdoor amenities, perfectly located moments from the heart of downtown Lenox, top-notch dining, Tanglewood, & the local high school on a quiet cul-de-sac. Step inside to a bright, freshly painted open floor plan framed by updated windows that flood the space with natural light. The inviting living area features a cozy gas fireplace, creating a warm focal point for chilly evenings, while the kitchen comes equipped with sleek, modern appliances. This turnkey residence offers 3 spacious bedrooms plus a versatile 4th full-size room that's ideal for a fourth bedroom, dedicated home office, or quiet retreat—along with 2.5 updated bathrooms. Downstairs, a vast, full open basement provides endless possibilities for exceptional storage, a home gym, or a recreation room. Beyond the interior, your ultimate outdoor sanctuary awaits in a professionally landscaped, fully fenced-in yard lined with a lush hemlock hedge for total privacy. Spend sunny summer days lounging by the sparkling in-ground saltwater pool, while the built-in swing set adds ready-to-use fun for family and guests. Complete with major exterior upgrades including an updated roof, newer siding, a spacious 2-car garage, and a shed, this exceptional property delivers total peace of mind and the best of Berkshire living right at your doorstep.

22 Post Rd, Lenox

$399,000

2 Beds ⋅ 2 Baths ⋅ 73562899 MLS

Close to Garnet Lake!!! Discover this Gorgeous home, constructed in 2007, presenting modern interior details and a Beautiful log exterior. This attractive property offers a unique opportunity for a primary residence or a getaway retreat.. The kitchen is thoughtfully designed with an abundance of fine cabinetry providing both functionality and a central gathering space for culinary endeavors. Open to the kitchen you will find an inviting Dining area and Family Room with impressive high wood ceilings. A first floor bedroom, full bath and a possible additional bedroom or den complete the first level. As you make your way to the second level you will find a comfortable loft area, an additional bedroom and a full bath. The property's exterior showcases a log architectural style, harmonizing with its natural surroundings. A built-in garage provides convenience and secure parking. For outdoor enjoyment. Rear deck extend the living space, offering venues for relaxation and entertaining. Enjoy rights to Garnet Lake a short stroll down the way!! To truly appreciate the distinctive character and lifestyle offered by this property, a personal viewing is highly recommended.

35 South Rd Ext, Peru

$325,000

3 Beds ⋅ 1 Baths ⋅ 73561617 MLS

Welcome to this bright and inviting 3-bedroom, 1-bath ranch, ideally located just moments from beautiful Pontoosuc Lake on a spacious double lot. This home features a generous living room with oak hardwood floors, a formal dining room, and an updated kitchen with newer countertops. Additional highlights include a spacious basement with abundant storage, an oversized one-car garage, and an enclosed seasonal porch-the perfect place to relax. The fully fenced backyard offers plenty of space for gardening, entertaining, pets, or simply unwinding. Conveniently located near the lake, shopping, dining, and local amenities, this home offers the perfect blend of comfort, convenience, and outdoor living.Enjoy the convenience of living just moments from Pontoosuc Lake Park, where boating, swimming, kayaking, canoeing, picnicking, and breathtaking sunsets can become part of your everyday lifestyle. One of Pittsfield's most popular recreational destinations, the park also features a public boat ramp and picnic areas.Ideally situated in the heart of the Berkshires, this home is just minutes from downtown Pittsfield, Onota Lake, Jiminy Peak Mountain Resort, scenic hiking trails, museums, acclaimed theaters, restaurants, shopping, and the region's year-round cultural and outdoor attractions.Whether you're looking for a year-round residence or a relaxing Berkshire retreat, this light-filled home offers the perfect blend of comfort, convenience, and outdoor recreation in one of Pittsfield's most desirable lake-area neighborhoods. Don't miss this wonderful opportunity to enjoy the best of Berkshire living.

296 Hancock Rd, Pittsfield

$158,900

2 Beds ⋅ 1 Baths ⋅ 73560750 MLS

Welcome to 186 Burbank Street! This charming colonial-style home offers two bedrooms, one full bathroom, and 1,158 square feet of living space. Situated on a level corner lot in an established residential neighborhood, the home features a functional layout with plenty of potential. The main level includes a spacious kitchen with ample cabinet and counter space, a formal dining room, comfortable living room, and full bathroom. Upstairs, you’ll find both bedrooms. A full basement provides plenty of additional storage, while the attached garage and private driveway offer convenient off-street parking. Conveniently located near Silver Lake, Lakewood Park, shopping, dining, and other local amenities. Bring your ideas and make this Pittsfield home your own! This property is eligible under Freddie Mac First Look Initiative through 09/06/2026. Only owner occupant, non-profit and Neighborhood Stabilization Program (NSP) offers will be reviewed and considered.

186 Burbank St, Pittsfield

$279,900

3 Beds ⋅ 2 Baths ⋅ 73559755 MLS

Large well maintained Colonial on a half acre lot. Large open kitchen with lots of cabinet space. Sliders off kitchen leading to back deck. Bright and sunny living space with a bonus den or office. 3 full sized bedrooms. 2 full baths. Laundry hookups on 2nd floor for convenience. Seller willing to buy down the mortgage rate on this home. One year American Home Shield Warranty included. PLEASE BOOK SHOWINGS THROUGH SHOWINGTIME.

528 Walker St, Lenox

$113,900

1 Beds ⋅ 1 Baths ⋅ 73559009 MLS

Have you been searching for an affordable retreat in the Berkshires? Nature lovers, hikers & outdoor enthusiasts, could this be the one you've been waiting for. Last house before entrance to one of Skyview Association's docks & water. Not waterfront but oh so close, check out the map. Nestled among trees this cottage offers a peaceful escape where mornings begin with birdsong & evenings end around the fire under the stars. The living room features large windows that bring the outdoors in, while the oversized bedroom provides plenty of sleeping space for family & guests. Structure supported on piers; some piers are leaning/settling. Two sheds for extra storage. Bring your vision, your tools, & your love of the outdoors to restore this cabin into the getaway it was meant to be. Skyline Association members have access to several boat launches & beach. EASY to show. Agents use ShowingTime.

26 Bear Hill Rd, Hinsdale

$2,149,000

4 Beds ⋅ 5 Baths ⋅ 73558556 MLS

Luxurious, fully-modernized 1850s Victorian in the heart of Great Barrington. Elegant, four-story 3600 sq. ft. newly renovated clapboard and shingle house with covered porch. Meticulous renovation features chef's kitchen, 4+ bedrooms, 4.5 bath, second floor and basement laundry, walk-out finished basement with private entrance and bathroom, perfect for guest suite or professional office. High-end appliances, including 6-burner Wolf stove and Bosch French door refrigerator with two freezer drawers, Bosch dishwasher, wine cooler and microwave in the island. Full-size prep sink in the kitchen island, 36'' farmhouse sink in the main counter. Cabinets are all-wood with soft-close drawers and doors; vented whole-house A/C and heat pump with propane back-up; primary bath with heated floor gas grill. EV charging station in driveway. Walking distance to Lake Mansfield and Main Street shops, restaurants and theaters. House can be sold furnished.

10 Berkshire Heights, Great Barrington

$329,999

3 Beds ⋅ 2 Baths ⋅ 73558221 MLS

NEWLY REDUCED — OPEN HOUSE SUNDAY, SEPTEMBER 6TH ??92 East Avenue • North Adams, MAOPEN HOUSE, SEPTEMBER 6TH, 11AM – 1PMA great opportunity to own a beautifully maintained colonial in one of North Adams’ most established and best-kept neighborhoods.This move-in-ready 3-bedroom, 1.5-bath home offers 1,632 square feet of comfortable living space, beautiful hardwood floors throughout, and the character and warmth of a classic New England home, including an amazing view of the mountains.Outside, you’ll find a level, freshly landscaped yard with mature shrubs and easy upkeep — all set in a quiet, well-cared-for neighborhood where the location is hard to beat.Now newly reduced, this home is a wonderful opportunity for buyers looking for a combination of character, location, and value in the Berkshires.

92 East Ave, North Adams

$269,900

5 Beds ⋅ 2 Baths ⋅ 73558023 MLS

Lovely five bedroom two bath Colonial on 5500+ sq.ft. of land.Lots of space, front porch for relaxing on beautiful summer evenings. Two bedrooms on the first floor and three bedrooms on the second floor with a deck off the bedroom and off the kitchen on the first floor. Two driveways for plenty of parking!!!Three sheds on property for storage will stay. Or not.

12 Lincoln Street, Pittsfield

$589,000

3 Beds ⋅ 1 Baths ⋅ 73556884 MLS

Escape to your own island retreat where each day is a peaceful, waterfront sojourn. Nestled on an island in Big Pond, this tranquil waterfront property offers extraordinary privacy, natural beauty and modern comfort. Thoughtfully updated, the home features a masterfully renovated kitchen and bath, a first-floor bedroom and distinctive architectural details including cedar shakes, that create warmth and character throughout. All furnishings to stay. Mornings of seasonal birdsong and the delicate beauty of the new day invite ease and comfort both on the screened, full-windowed porch or on the two outdoor decks. Breathtaking views of the lake encourage leisurely relaxation while winding garden paths and natural stone walls enhance the property’s timeless appeal. A large boathouse provides exceptional storage for all your recreational equipment and includes a clothes dryer and refrigerator for added convenience. If you enjoy sailing, paddling or simply exploring the water, the property’s sailboat, canoe, kayaks and motorboat allow you to embrace an active and energetic lifestyle on this 330-acre lake. Tension and stress melt away as you cross the water to your own secluded oasis. Here you’ll discover enduring serenity, stunning scenery and stimulating outdoor activities where privacy and nature surround you. Tanglewood, world-class art museums and theatre, shopping, dining and everyday conveniences remain within easy reach in Otis and the nearby Berkshire hills.

18 Big Pond, Otis

$1,275,000

4 Beds ⋅ 6 Baths ⋅ 24193129 MLS

MAGNIFICENT circa 1913 ESTATE Rare opportunity to own a distinguished country estate. The stately main home showcases exceptional craftsmanship, a grand foyer with sweeping staircase, expansive kitchen with butler's pantry, formal living spaces, sun porch, and multiple covered porches. The luxurious primary suite offers a sitting room, balcony, sun porch, and spa-like bath. Three additional bedrooms, two baths and two offices complete the second floor. A finished third floor provides flexible additional space. Attached spacious garage that can park 4 cars in double tandem. Surrounded by mature grounds on 5.7 acres and within walking distance of village of Dalton.

1 Park Ave, Dalton

$1,275,000

4 Beds ⋅ 8 Baths ⋅ 73552517 MLS

MAGNIFICENT circa 1913 ESTATE. Rare opportunity to own a distinguished Berkshire. The stately main home showcases exceptional craftsmanship, a grand foyer with sweeping staircase, expansive kitchen with butler's pantry, formal living spaces, sun porch, and multiple covered porches. The luxurious primary suite offers a sitting room, balcony, sun porch, and spa-like bath. Three additional bedrooms, two baths and two offices complete the second floor. A finished third floor provides flexible additional space. Attached spacious garage that can park 4 cars in double tandem. Surrounded by mature grounds on 5.7 acres and within walking distance of village of Dalton.See the Stone House Properties web site for further details.

1 Park Ave, Dalton

$474,999

4 Beds ⋅ 3 Baths ⋅ 73550281 MLS

Privacy, space, and the beauty of the Berkshires come together at 125 Town Hill Road. Set on nearly 3 wooded acres in the peaceful town of Sandisfield, this 4-bedroom, 3-bath contemporary offers a private retreat surrounded by nature. The home features comfortable living spaces, a screened porch, spacious deck, finished walk-out lower level, and a private tennis court. Enjoy the serenity of country living while being conveniently located near lakes, hiking, skiing, restaurants, galleries, and the charming towns of the southern Berkshires. A special setting for a year-round home or Berkshire getaway.

125 Town Hill Rd, Sandisfield

$1,750,000

6 Beds ⋅ 5 Baths ⋅ 73550137 MLS

Own a Living Masterpiece. Meticulously curated by the current stewards since 2006. This Colonial Revival offers rare fusion of 18th-century authenticity and cutting-edge modern comfort. Designed for both grand-scale entertaining and intimate family life, this c1930, 7,894 sq. ft., Colonial Revival offers 6-bdrms & 4.5-baths. The interior is a treasure of artisan craftsmanship from the formal dining room with its magnificent shell-carved cove, to original cabinetry with rare wood inlays, hand-carved bookshelves, a classic butler's pantry, multiple stately fireplaces anchor the formal living spaces. Enjoy panoramic views and privacy from the grand porch overlooking 4 pristine acres. a state-of-the-art kitchen featuring Wolf and Sub-Zero, and no expense spared Geo-Thermal heating/cooling.

500 Williams, Pittsfield

$599,000

3 Beds ⋅ 1 Baths ⋅ 73549125 MLS

Vacation all year round! This turnkey lakefront house offers modern comfort and a stunning view of Ashmere Lake. Tucked on the eastern cove side of the lake, it provides a more sheltered stretch of waterfront. The main level features two bedrooms with oak hardwood floors and individual heat pumps for customizable comfort. The kitchen is finished with granite countertops, soft close cabinetry, and a practical open concept layout. The 2nd floor offers additional living space for a bedroom or quiet lounging, with a lovely front facing view of the lake. Mechanical updates include a new hot water heater, electric service panel, heating panels located in both the full bathroom and the basement, as well as heat pumps in the main living area, the 2nd floor and in the bedrooms. A deck off the main level overlooks a sweet "daisy flower yard" which supports pollinators. Dip your feet into the lake off of your own private dock!

36 Tamarack Rd, Hinsdale

$599,900

3 Beds ⋅ 2 Baths ⋅ 73548488 MLS

Escape to the beauty of the Berkshires with this charming 3-bedroom, 2-bath retreat near Otis Reservoir! This inviting home features soaring vaulted ceilings, abundant natural light, a stunning stone fireplace, spacious bedrooms, a versatile loft, and a bright kitchen perfect for gathering. Relax on the front porch, enjoy evenings around the fire pit, and take advantage of the storage shed for all your outdoor gear. With deeded rights to Otis Reservoir, you'll enjoy easy access to boating, fishing, swimming, and year-round recreation. Currently operating as a successful Airbnb offering excellent income potential. Whether you're looking for a vacation getaway, investment property, or full-time residence, this home is a must-see. Please note: As an active short-term rental, all showings require confirmation. A group showing will be scheduled, with the date to be announced.

400 Pine Road, Otis

$395,000

3 Beds ⋅ 3 Baths ⋅ 73545078 MLS

Modern ranch home perched high above North Street offering views to the east and bordering the approximate 370,000 acre Appalachian trail on two sides! Enjoy direct access for hiking right off your property! Offering 3 bedrooms, 3 full baths and extremely nice mechanicals updated in recent years. The lower level consists of a one bay garage/storage area and a beautiful in-law accommodations. The location is ideal and convenient to all things Berkshire County from cultural, restaurants and attractions with Williamstown / North Adams only 10-16 miles to the north and Tanglewood in Lenox roughly 19 miles to the south. Fishing and boating in Cheshire Lake or Pontoosuc Lake and Jiminy Peak Ski resort within a short drive.

335 North St, Cheshire

$395,000

3 Beds ⋅ 2 Baths ⋅ 73548213 MLS

Modern Ranch Home with additional wooded lot and breathtaking views bordering vast State Lands!Impeccably kept Ranch home including additional wooded lot on a quiet paved road less traveled bordering state lands. Nicely finished, open and light filled kitchen, dining and living room boasting long range views of our states highest peak, Mount Greylock. No better way to watch the color pallets of the Berkshires than from the expansive deck overlooking the sprawling yard and distant views. Primary bedroom suite to the northeast and two guest bedrooms with separate full bath to the southwest affording privacy with functionality in its flow. Beautiful grounds for outdoor entertaining, or stargazing by the fire. Spectacular shed / workshop with overhead garage door. Don't forget the additional lot for expanded compound or ADU if desired. Close to all Berkshire County attractions!

472 & 0 East Hoosac St, Adams

$150,000

5 Beds ⋅ 2 Baths ⋅ 73547265 MLS

Bring this charming 1800s farmhouse back to life! Offering nearly 3,000 square feet of living space, this property is packed with potential for investors, contractors, or buyers looking for their next renovation project. Previously configured with an in-law apartment, it may offer the opportunity to convert to a two-family home with the proper permits and approvals. With its generous footprint and endless possibilities, this property is ready for a complete transformation. Investors take note—once renovated, this could become a truly exceptional property with significant upside.

842 Church St, North Adams

$14,500,000

19 Beds ⋅ 25 Baths ⋅ 73544510 MLS

The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody & Stearns, this 16th-century Florentine palazzo features stunning grounds by Frederick Law Olmsted. Former home to the Boston Symphony Orchestra and moments from Tanglewood, this 25,000+SF architectural sanctuary seamlessly marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, a formal dining room, a refined wine cellar (6,500-bottle capacity), and 19 uniquely curated bedroom suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the pool and tennis court. This iconic estate offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance.

11 Hawthorne, Stockbridge

$325,000

5 Beds ⋅ 3 Baths ⋅ 73542282 MLS

Discover the perfect blend of space, versatility, and charm in this distinctive five bedroom, three bathroom home on a quiet one-way street just minutes from downtown. Rich in unique character and history, this property showcases timeless architectural details and a flexible layout to accomodate a variety of needs. A separate apartment offers excellent potential for extended family, guests, or rental income. A three-bay attached garage provides ample storage space, room for hobbies, or the opportunity to create a workshop to suit your needs. With generous living space, endless potential, and a prime location, this one-of-a-kind property is ready for it's next chapter.

58 Quincy Street, North Adams

$235,000

3 Beds ⋅ 2 Baths ⋅ 73540567 MLS

Welcome to this spacious 3-bedroom, 2-bath home offering 1,920 square feet of living space in Pittsfield's desirable Morningside neighborhood. This home blends classic character with several major updates already completed, including a newer roof (2025), replacement windows, oil tank (2024), boiler (2019), and sewer line (2019). The flexible floor plan provides plenty of room for everyday living, entertaining, or multi-generational needs. Enjoy an eat-in kitchen, full basement with interior and exterior access, a detached one-car garage, and a generous lot with mature landscaping. Conveniently located near parks, schools, restaurants, shopping, and downtown Pittsfield. Located in an RM-zoned district, this property may offer future multi-family or investment potential, subject to buyer due diligence. Property is being sold AS IS. A great opportunity for investors, cash buyers, or conventional financing buyers looking to add value while building equity through cosmetic improvements.

20 Curtis Ter, Pittsfield

$799,000

2 Beds ⋅ 1 Baths ⋅ 73534578 MLS

Rare opportunity to acquire a unique five-parcel package totaling approximately 33.37 acres in scenic Williamstown. Offered as one sale, the package includes 95 & 97 Luce Road, each with an existing residence situated on 5.50 and 5.90 acres respectively, plus three additional raw land parcels totaling approximately 21.97 acres. The existing homes are in significant disrepair and are best suited for redevelopment, renovation, or replacement. This offering presents a variety of possibilities including an estate property, recreational retreat, investment opportunity, or potential future development. Set amidst the natural beauty of the Berkshires, the property enjoys a peaceful setting with potential mountain and countryside views, while remaining convenient to Williams College, downtown Williamstown, and Mount Greylock. Existing road frontage, access, and utility infrastructure add value beyond raw land alone. Buyer to independently verify all information, including zoning and land use.

97 Luce Rd, Williamstown

$375,000

6 Beds ⋅ 2 Baths ⋅ 73531392 MLS

Escape to the Berkshires in this stunning Victorian gem — designed for those who appreciate space, style, and character. Whether you're planting roots in North Adams or seeking a weekend retreat. Fully renovated 5-bed, 2-bath home with 2,551 sq ft in the heart of North Adams. Slate roof, repainted front porch, chimney repairs, and updated plumbing and electrical throughout. Inside features refinished black India ink hardwood floors, new lighting fixtures, popcorn ceiling removal, washer/dryer hookups, and designer finishes including Revere Pewter and Gentlemen's Grey. Both bathrooms fully refreshed with new tile, fixtures, and flooring. Furniture included.Minutes from Mass MoCA and the Mohawk Trail. Proven short-term rental with 4 years of documented Airbnb performance, consistent 5-star guest reviews. Professional management on 24/7 - completely turnkey. Active Airbnb listing available upon request to verify income history. Showings available between guest stays.

71 North Holden St, North Adams

$1,100,000

4 Beds ⋅ 3 Baths ⋅ 73531374 MLS

EXCEPTIONAL WATERFRONT RETREAT ON TRANQUIL HAYES POND!Nestled on over 3 private acres w/an extraordinary 650 feet of frontage on Hayes Pond,this exceptional waterfront retreat offers sweeping elevated views,a private dock, sandy beach, & direct access to swimming, kayaking, & fishing.Designed to embrace its stunning natural setting,the home features expansive windows & multiple outdoor living spaces, including a wraparound deck, waterside gazebo, & screened porch w/hot tub connection--perfect for entertaining or relaxing in every season.The bright open-concept interior includes 4 bedrooms & 3 full baths,highlighted by a dramatic great room w/ knotty pine ceilings,a wood-burning stove w/stone hearth, & direct deck access overlooking the water.The spacious primary suite also opens to the deck & features its own and features its own wood-burning stove & en suite bath.The walkout lower level offers additional living space w/ a family room,full bath,& two and two bedrooms ideal for guests.

13 Hayes Pond Rd, Otis

$239,900

2 Beds ⋅ 1 Baths ⋅ 73530997 MLS

Charming bungalow in the heart of North Adams w/ beautiful mountain views! Conveniently located near downtown, offering easy access to restaurants, shopping, MASS MoCA, Hospital, and a vibrant art & cultural scene. Designed for comfortable one-level living, the home features beautiful hardwood floors throughout, vinyl windows, 2 bedrooms, and a spacious living/dining combination w/ a pellet stove. The kitchen features tile countertops, S/S appliances, and ample cabinetry. The front porch includes 1st floor laundry & built-in shelving. There is a full basement & a Walk-up attic. Outside, you'll appreciate the low-maintenance stone exterior, mature landscaping, a large paved driveway, and a 2 car garage. The property is just 30 minutes from Jiminy Peak Mountain Resort & Mount Greylock, & only 10 minutes from Williamstown & Vermont. Whether looking for a primary residence or a Berkshire getaway, this home offers comfort, convenience, & easy access to the region's most popular attractions.

21 River St, North Adams

$219,900

3 Beds ⋅ 1 Baths ⋅ 73527614 MLS

ecently renovated home with convenient first floor bedroom and full bathroom, and two additional bedrooms on the second floor. The front yard is fenced in. The backyard is a great space to gather. The basement has concrete floor and there is natural gas heat and hot water, and metered water. The home has a certificate of insulation and it shows how helpful it is as the utility bills are very low. This is a great opportunity to own a home that is cozy and affordable, located close to the hospital and downtown.

68 Orchard St, Pittsfield

$1,450,000

3 Beds ⋅ 3 Baths ⋅ 73527324 MLS

Discover an extraordinary lakefront opportunity on Otis Reservoir featuring a combination of amenities rarely found in a single package. Combined with the lower lot, enjoy 62 feet of direct waterfront, a super rare grandfathered boathouse dock with electricity and electric lift, a waterfront bathhouse with living room, heated garage, dedicated hot tub room with fireplace, and a floor plan designed to capture stunning lake views from nearly every room. Perfect for entertaining, the home offers a spacious updated kitchen, multiple living areas, separate driveways with ample off-street parking, and two storage sheds for all your lake and seasonal gear. Extensively remodeled in 2021 with new heating and cooling systems, on-demand hot water, and a beautiful kitchen featuring stacked cabinetry, full-slab quartz countertop island, stainless steel appliances, and a gas range. The walk out basement provides easy access to the outside as well. Sold fully furnished and ready to enjoy from day one

347 Pine Rd, Otis

$660,000

5 Beds ⋅ 3 Baths ⋅ 73522628 MLS

Tucked away on a serene & private lot just minutes from the sparkling waters of Otis Reservoir, this stunningly renovated 5-bedroom, 3-bath Colonial offers the perfect blend of luxury, comfort, and natural beauty. Designed for both elegant entertaining and everyday living, the heart of the home is the spectacular chef’s kitchen featuring quartz countertops, abundant cabinetry, and refined finishes throughout. The thoughtfully designed 1st flr offers a formal living room, sophisticated dining area, two spacious bedrooms, and a beautifully updated full bath — ideal for guests or flexible living arrangements. Upstairs, retreat to the luxurious primary suite complete with a private ensuite bath, along with two additional generously sized bedrooms and a third full bath. Surrounded by peaceful nature views, trails and exceptional privacy, this remarkable property is a rare opportunity to enjoy upscale living in a tranquil setting to enjoy all the beauty the Berkshires have to offer.

23 Old Blandford Road, Otis

$439,900

3 Beds ⋅ 2 Baths ⋅ 73522105 MLS

Be the first to live in this newly built split-entry home in Becket. Located in the Sherwood Forest community, it is just a few minute walk away from the private beach and lake. A private, fenced-in yard with gated access welcomes you on arrival. Exterior highlights include a deck overlooking serene wooded views and a covered patio below—perfect for outdoor entertaining. The main level offers an open-concept layout with a light-filled living room flowing into the dining area and kitchen. The kitchen features an island, new stainless steel appliances, shaker cabinets, and quartz countertops. This level also includes two bedrooms and a full bath. The partially finished lower level provides additional living space with a bonus room, a full bath with laundry, and interior access to the attached one-car garage. Additional features include vinyl-plank flooring throughout, tile-finished bathrooms, a subway-tiled bathtub on the main level, and a high-efficiency hybrid heat-pump water heater.

102 Wells Road, Becket

$335,000

3 Beds ⋅ 1 Baths ⋅ 73521998 MLS

Enjoy this charming, move-in ready property set in a peaceful and quiet setting in Williamstown. Featuring a spacious backyard with a large deck, this home is perfect for relaxing or entertaining outdoors all summer long. Inside, you'll find a warm and inviting atmosphere with a blend of original hardwood floors and updated newer flooring throughout. The kitchen offers an island, updated appliances, and an abundance of natural light, creating a bright and functional space for everyday living. A high-efficiency gas heating system provides modern comfort, along with on-demand hot water for added convenience. The recently updated roof adds peace of mind, while the basement offers excellent storage options. Ideally located just minutes from downtown Williamstown and nearby North Adams, this home provides easy access to a variety of local attractions, restaurants, and cultural destinations, including The Clark Art Institute and Massachusetts Museum of Contemporary Art.

54 Charles St, Williamstown

$886,000

3 Beds ⋅ 3 Baths ⋅ 73521856 MLS

The spacious front porch featuring stone accents & classic white columns sets the tone for the elegance found throughout. Beautiful mahogany French entry doors create a warm & timeless first impression & you'll immediately appreciate a captivating features: an uninterrupted view extending through the dramatic open living space & to a 2nd set of French doors to the covered rear deck ~ a perfect place for morning coffee, quiet conversations & relaxing evenings! The foyer showcases illuminated niches offering a sophisticated first impression & space to display artwork, collections, or decorative touches. The Living room is highlighted by a gas fireplace & soaring ceiling providing a remarkable sense of volume & light. The gourmet kitchen features a generous center island w/ seating, quality cabinetry, stainless appliances & a charming arched-entry pantry. The adjoining dining area is surrounded by windows. 1st floor laundry, spacious primary en suite. (all room sizes are approximate).

69 Elmore, Dalton

$519,900

3 Beds ⋅ 2 Baths ⋅ 73521350 MLS

Beautifully refurbished home in the Berkshires with deeded rights to the White Lily Pond Association, offering access to aprivate beach, tennis and pickleball courts. White Lily Pond is a quiet lake ideal for canoeing, kayaking, paddleboarding, andtrolling motors only. Renovated with quality craftsmanship throughout, the home features upgraded insulation, efficientpropane heat, and inviting living spaces. The custom kitchen includes granite countertops, a large island, gas range, andcustom cabinetry. The living area is highlighted by a fireplace with handcrafted custom sconces. Currently getting $5500 per month for Air BNB

1791 Algerie Rd, Otis

$229,900

2 Beds ⋅ 2 Baths ⋅ 73521129 MLS

Charming and full of potential, this inviting two-bedroom Cape is tucked away on a quiet dead-end street and ready for its next owner! A fieldstone walkway welcomes you and adds timeless curb appeal from the moment you arrive. Inside, you’ll find an enclosed front porch perfect for enjoying your morning coffee, an updated kitchen including refrigerator and stove, a convenient first-floor bedroom, and a practical mudroom offering comfort and flexibility. The second floor features a primary bedroom with a half bath, while built-in drawers and additional closet space complete the hallway. Classic warmth and character can be found throughout the home. Outside, the spacious partially fenced backyard provides a private retreat perfect for relaxing or entertaining. Gather around the outdoor stone fireplace and enjoy cozy evenings with family and friends. A detached garage adds extra storage and convenience. Great opportunity to build equity!

48 Crystal Street, Pittsfield

$1,650,000

4 Beds ⋅ 4 Baths ⋅ 73520634 MLS

Pre-Construction: Step into a brand-new construction home designed to bring together modern comfort, generous space, and the natural beauty of the Berkshires. The heart of the home is an expansive open kitchen, dining, and family room area made for entertaining, slow mornings, and everyday living, complete with a walk-in pantry and seamless access to the rear deck. A separate study and additional living room offer flexibility for working from home, guests, or quiet retreat space. Upstairs, the vaulted primary suite features oversized walk-in closets and a spacious bath, joined by 3 additional bedrooms, multiple full baths, and second-floor laundry. A full unfinished basement offers future expansion potential, solar-ready design, and an attached 2-car garage add modern convenience. Ideally situated in Becket, moments from hiking, lakes, skiing, local trails, and the renowned Jacob’s Pillow arts destination, with year-round access to everything the Berkshires is known for.

79-B Woodmere, Becket

$1,650,000

4 Beds ⋅ 4 Baths ⋅ 73520630 MLS

Pre-Construction: Step into a brand-new construction home designed to bring together modern comfort, generous space, and the natural beauty of the Berkshires. The heart of the home is an expansive open kitchen, dining, and family room area made for entertaining, slow mornings, and everyday living, complete with a walk-in pantry and seamless access to the rear deck. A separate study and additional living room offer flexibility for working from home, guests, or quiet retreat space. Upstairs, the vaulted primary suite features oversized walk-in closets and a spacious bath, joined by 3 additional bedrooms, multiple full baths, and second-floor laundry. A full unfinished basement offers future expansion potential, solar-ready design, and an attached 2-car garage add modern convenience. Ideally situated in Becket, moments from hiking, lakes, skiing, local trails, and the renowned Jacob’s Pillow arts destination, with year-round access to everything the Berkshires is known for.

79-A Woodmere, Becket

$269,000

4 Beds ⋅ 2 Baths ⋅ 73519024 MLS

Enjoy this charming 4-bedroom, 2-bathroom home offering a spacious and functional layout, tasteful updates, and excellent convenience. The property features an updated heating system, efficient natural gas utilities, a large open kitchen with new appliances, and updated flooring. Both bathrooms have been recently renovated with stylish new finishes and tilework. Enjoy the flexibility of a first-floor bedroom and full bathroom, along with a partially finished basement offering additional living space, separate laundry area, and excellent storage potential. Outside, the spacious yard and detached two-car garage provide plenty of room for outdoor enjoyment, entertaining, and everyday convenience.

162 West Housatonic, Pittsfield

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