Berkshire County MA Homes for Sale with In-Law Suite

/57
$3,450,000
- 6 Beds
- 5.5 Baths
- 4,681 Sq Ft
1333 Norfolk Rd, Southfield, MA 01259

Set on 11 enchanting acres in the pastoral town of New Marlborough, Massachusetts, this exceptional Berkshires estate offers a rare convergence of architectural refinement, natural splendor, and modern luxury. Designed by an architect and originally built in 1984, the main house, guest house, and pool house were all fully renovated in early 2025 to create a cohesive, contemporary compound with

Selina Lamb

BIRCH PROPERTIES

(413) 327-9228

1333 Norfolk Rd, Southfield, MA 01259
/77
$5,800,000
- 15 Beds
- 14.5 Baths
- 11,670 Sq Ft
764 E Hill Rd, New Marlborough, MA 01230

High on a hilltop in the Southern Berkshires stands East Hill Farm. 227 cultivated acres encompassing pristine forest, spring-fed pond, striking barn, verdant pastures, formal and vegetable gardens, pool, and tennis court. The centerpiece: a 1798 Georgian home, 5,000sf. & 5 bedrooms.Ready for private living, entertaining, horses, farming, a bespoke destination, or simply: tranquility. Includes a

Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

764 E Hill Rd, New Marlborough, MA 01230
/61
$1,790,000
- 6 Beds
- 6.5 Baths
- 5,115 Sq Ft
76 Lenox Rd, West Stockbridge, MA 01266

New World meets Old in this impeccably designed and elegant French Country inspired estate nestled perfectly on the hillside, affording gorgeous westerly mountain and sunset views. Situated on 3.76 acres, the home offers ample privacy, yet it is just a stone's throw from Tanglewood and downtown Lenox and West Stockbridge. Designed for hosting extended family and friends, it offers generously

Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

76 Lenox Rd, West Stockbridge, MA 01266
/69
$5,900,000
- 11 Beds
- 10 Baths
- 9,748 Sq Ft
25 W Sheffield Rd, Great Barrington, MA 01230

Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of future for generations

Lauren Molk ELYSE HARNEY REAL ESTATE

25 W Sheffield Rd, Great Barrington, MA 01230
/55
$2,500,000
- 5 Beds
- 5.5 Baths
- 5,233 Sq Ft
55 Main St, Stockbridge, MA 01262

Historic Elegance Reimagined!Wellness-forward design. Artisan craftsmanship. In-town privacy.A Kitchen Rebuilt from the Ground Up: At the heart of the home, a brand-new chef's kitchen makes a bold, refined statement with honed dark gray granite countertops, crisp white shaker cabinetry, and minimalist matte black fixtures. Oversized divided-light windows flood the space with natural light, while

Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

55 Main St, Stockbridge, MA 01262
/40
$1,795,000
- 4 Beds
- 4 Baths
- 3,524 Sq Ft
1 Old Tree Farm Rd, Stockbridge, MA 01262

Impeccably Renovated Stockbridge Country Retreat. Minutes from Stockbridge, Lenox and Tanglewood, in the heart of the Berkshires cultural corridor, a rare opportunity in a perfect setting on 4.25 level, landscaped acres. Surrounded by mature trees and curated gardens, this home blends classic design with modern updates, offering refined style throughout. White oak floors, three full baths, a gas

Suzann Ward HOUSATONIC REAL ESTATE

1 Old Tree Farm Rd, Stockbridge, MA 01262
/55
$1,675,000
- 4 Beds
- 2 Baths
- 2,200 Sq Ft
5 Glendale Rd, Stockbridge, MA 01262

Two Dwellings on almost four acres.Just a very special property. Located between the Rockwell Museum and the Botanical Garden. You are moments from Tanglewood. Equidistant from Lenox and Great Barrington providing easy access to the Berkshires wonderful restaurants. The main house has four bedrooms and two baths , while the guest cottage adds another bedroom, bath, and large living room. The

Martha Piper THE KINDERHOOK GROUP - PITTSFIELD

5 Glendale Rd, Stockbridge, MA 01262
/20
$3,995,000
- 15 Beds
- 15 Baths
- 11,945 Sq Ft
615 Laurel St, Lee, MA 01238

The Lakehouse enjoys a spectacular setting on a westerly facing cliff overlooking pristine Laurel Lake in the heart of The Berkshires. The Lakehouse is a classic three-story, shingle style mansion with 530' of lake frontage including its own dock. Built in 1903, the architecture denotes the unpretentious, timeless elegance of a turn-of-the-century lakeside cottage. There are 15 bedrooms and

Pamela J Long EAST COAST INN BROKERS

615 Laurel St, Lee, MA 01238
/51
$1,949,000
- 4 Beds
- 3.5 Baths
- 3,200 Sq Ft
9 Bott Hill Rd, Egremont, MA 01230

Stunning Post and Beam Home with Log Facade. Nestled in a park-like setting with views of Mount Washington. Outdoor Amenities Galore. Extensive patios and wraparound decks provide the perfect venues for outdoor gatherings including a private bocce ball court, outdoor hot tub, and private dog park. The first floor offers generous entertaining spaces, including two to three bedrooms that provide

Suzann Ward HOUSATONIC REAL ESTATE

9 Bott Hill Rd, Egremont, MA 01230
/82
$4,500,000
- 4 Beds
- 3 Baths
- 5,256 Sq Ft
381 Sheffield-Egremont Rd, Sheffield, MA 01257

SPECTACULAR ONE OF A KIND BERKSHIRE PROPERTY! This compound includes an elegant and updated 4 bedroom 1759 Colonial home and fabulous RED BARN with 2 separate guest spaces. Mill pond for fishing, heated pool, patios and screen porch, 66 protected SUBDIVIDABLE ACRES...with views of Mount Washington. The perfect place to entertain friends and family. An incredible opportunity for additional

Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

381 Sheffield-Egremont Rd, Sheffield, MA 01257
/71
$2,200,000
- 5 Beds
- 4.5 Baths
- 3,354 Sq Ft
176 W Center Rd, West Stockbridge, MA 01266

The lovely approach to this gorgeous estate property ensures serenity, privacy, and the beauty of living in the country and includes a 3 bed 2 1/2 bath main house and a gorgeous architect designed guest house. Offering 2 ensuite bedrooms with balconies, dramatic exposed beams, vaulted ceilings, and gas fireplace the guest house is an extraordinary place to host family and friends both

Lori Rose STONE HOUSE PROPERTIES, LLC

176 W Center Rd, West Stockbridge, MA 01266
/52
$1,849,235
- 4 Beds
- 3.5 Baths
- 4,968 Sq Ft
42 Seekonk Rd, Great Barrington, MA 01230

The Piano House was named for the ornamental Dentil wood trim at the top of the facade an 1810 Center Hall Federal Colonial, located on 4.59 acres at Alford Brook, Features a Rumford Fireplace in the Front Lounge and in the Sitting Room. Also, a Large Wood Burning Stove in the Dining Room-Family/Sunroom. In addition, an 1810, two story Barn with 1185 sq. ft. of refurbished space. Includes a

Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

42 Seekonk Rd, Great Barrington, MA 01230
/66
$2,250,000
- 5 Beds
- 6 Baths
- 5,477 Sq Ft
1030 West St, Pittsfield, MA 01201

1030 West is a bespoke family compound on 6 acres between Onota Lake and Pittsfield State Forest, offering refined country living with city convenience. The historic main house, decorated by designer Heidi Caillier and featured in her book Memories of Home, has been thoughtfully renovated with timeless materials - custom cabinetry, marble, limestone, Waterworks fixtures, designer and vintage

Tracy Crawford COMPASS MASSACHUSETTS , LLC GB

1030 West St, Pittsfield, MA 01201
/50
$1,950,000
- 5 Beds
- 4.5 Baths
- 4,301 Sq Ft
20 E Dugway Rd, Lenox, MA 01240

Lenox Estate on 36 Acres - Two HomesJust one mile from the center of Lenox, this unique estate offers exceptional space and versatility with two separate residences. The main home boasts 4,100 square feet with five bedrooms and three and a half bathrooms--perfect for spacious living or entertaining. The second home is a charming 1,200-square-foot residence with two bedrooms and two full baths,

Tanya Shepardson LAMACCHIA REALTY, INC

20 E Dugway Rd, Lenox, MA 01240
/47
$1,795,000
- 4 Beds
- 3 Baths
- 2,686 Sq Ft
24 Baldwin Hill Rd E, Egremont, MA 01230

Located on one of Egremont's most picturesque roads, this beautifully designed contemporary home offers panoramic views from nearly every room. Set in a low-tax town just minutes from Great Barrington, this home is private, comfortable and versatile. The main house has perfect flow, great scale rooms, tons of light, a beautiful stone fireplace, custom Kitchen, and the prettiest of outdoor

Helen Mullany HELEN MULLANY REAL ESTATE, LLC

24 Baldwin Hill Rd E, Egremont, MA 01230
/49
$1,875,000
- 5 Beds
- 5.5 Baths
- 3,225 Sq Ft
5 Easland Rd, West Stockbridge, MA 01266

A Home Designed for Living and RetreatNestled at the base of Tom Ball Mountain on over 10 private acres, 5 Easland Road is a custom-designed contemporary sanctuary where nature, luxury, and thoughtful craftsmanship come together in perfect harmony.This 5-bedroom, 5.5-bath home features soaring vaulted ceilings, dramatic walls of glass, and gleaming hardwood floors throughout. Each of the three

Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

5 Easland Rd, West Stockbridge, MA 01266
/46
$1,500,000
- 7 Beds
- 7.5 Baths
- 6,232 Sq Ft
802 State Rd, Richmond, MA 01254

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare colonial charm. Spanning 11 bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence, three enchanting cottages and a great barn for entertaining. The main residence, a testament to time-honored craftsmanship, features 7 bedrooms and 7.5 baths, each

Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

802 State Rd, Richmond, MA 01254
/40
$1,590,000
- 11 Beds
- 12.5 Baths
- 8,134 Sq Ft
518 Main St, Great Barrington, MA 01230

The iconic Wainwright Inn, built in 1766, is ideally located on Main Street in Great Barrington, the largest town & hub of the famous Berkshires vacation destination in Western Massachusetts. The Inn consists of a main house with 9 guest suites & a spacious owner's suite, & a carriage house with an apartment & two additional guest suites. In pristine condition, the current owners have improved

Tanya LeRose THE KINDERHOOK GROUP - PITTSFIELD

518 Main St, Great Barrington, MA 01230
/43
$1,890,000
- 5 Beds
- 4.5 Baths
- 6,000 Sq Ft
248 East Rd, West Stockbridge, MA 01266

A luxurious home on one of the most scenic roads in The Berkshires, surrounded by 15 pastoral acres, with picturesque mountain views. Enter a sun-drenched living room with a soaring cathedral ceiling and an elegant fireplace centerpiece. Enjoy an expansive 3-season porch, with panoramic windows and classic mahogany floors. A recently updated eat-in kitchen features Sub Zero appliances and a

Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

248 East Rd, West Stockbridge, MA 01266
/47
$1,575,000 New Construction
- 1 Bed
- 2 Baths
- 3,826 Sq Ft
293 East Rd, West Stockbridge, MA 01266

A Hidden Berkshire Gem - With a Cottage, a Dream, and over 30 Acres of PossibilityWelcome to BarKing Cow Farm ! Your future compound that is tucked away on almost 30 private acres of peace and possibility, this rare offering is a true diamond awaiting its final polish. Located in one of the Berkshires' most sought-after townsa"boasting the lowest tax rate in South Countya"this property invites

William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

293 East Rd, West Stockbridge, MA 01266
/60
$5,150,000
- 7 Beds
- 8.5 Baths
- 7,073 Sq Ft
1 Pinecroft Dr, Lenox, MA 01240

Gated Berkshire Stone Estate in exclusive Pinecroft compound with Canyon Ranch Living and its 125 maintenance-free acres. Optional membership. Turnkey home features elevator, 300-year-old reclaimed timber floors and large gourmet kitchen. Great room boasts floor-to-ceiling stone fireplace, wet bar, Nano doors to screened lanai. Two en suite bedrooms with cedar closets. Lower level: gym, sauna,

Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

1 Pinecroft Dr, Lenox, MA 01240
/39
$315,000
- 3 Beds
- 2 Baths
- 2,010 Sq Ft
74 South St, Cheshire, MA 01225

This spacious home has a nice size kitchen with quartz counters, lots of cabinets, dining room, fireplace living room and 3 large bedrooms. The addition on the first floor is being used as 4th bedroom with an ensuite bathroom, it can also be used for a large family room or in-law suite/guest room since it has private door entrance. Enjoy all the natural bright light coming through the many

Toni Marie Gage SIGNATURE ASSOCIATES

74 South St, Cheshire, MA 01225
/62
$629,000
- 4 Beds
- 2.5 Baths
- 1,716 Sq Ft
90 Via Franco, Lee, MA 01238

OPEN HOUSE SAT 7/26/25 10:30am-12:00pm. Don't miss this exceptional opportunity to own a spacious and beautifully updated home nestled on 1.34 acres in the heart of the Berkshires. Tucked away in a private setting yet just minutes from shopping, cultural attractions, and I-90, this home offers the perfect balance of peace and convenience. Enjoy the ease of one-level living with an updated kitchen

Cindy Carrigan LAMACCHIA REALTY, INC

90 Via Franco, Lee, MA 01238
/63
$1,100,000
- 3 Beds
- 2 Baths
- 2,174 Sq Ft
138 Mystic Isle Way, Becket, MA 01223

Prepare to be wowed by this stunning lakefront home, which was built with meticulous craftsmanship by a Connecticut engineer and recently transformed by the current owners. Notable features include over 2,100 sq ft of flexible living space, 80'+ lake frontage, and every modern amenity. This turnkey home, which includes two separate living quarters, is perfect for multi-generational living or

Stephanie Lachapelle COMPASS MASSACHUSETTS, LLC.

138 Mystic Isle Way, Becket, MA 01223
/58
$4,995,000
- 7 Beds
- 8 Baths
- 13,261 Sq Ft
319 Under Mountain Rd, Lenox, MA 01240

Pine Needles.Built circa 1900 as a Berkshire ''cottage'' in the era of grand summer estates, this historic property blends the dignity of Colonial Revival architecture with the relaxed elegance of an Italian villa and the artisanal detail of the Arts & Crafts movement. Sited on 80 private acres just minutes from the heart of Lenox, the estate offers breathtaking southern views, rolling forest,

Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

319 Under Mountain Rd, Lenox, MA 01240
/51
$825,000
- 3 Beds
- 3.5 Baths
- 4,160 Sq Ft
2232 Jacobs Ladder Rd, Becket, MA 01223

Experience the perfect blend of nature, sophistication, and comfort in this thoughtfully crafted home and carriage house on 4.25 acres. This property is packed with personality.Enjoy the mature gardens, the fabulous deck for entertaining, the inviting swimming pool, and a wooded path leading to a stone fire pit, one mile from Jacob's Pillow.The photographs will offer a clue as to why you need to

Claudia Crane COMPASS MASSACHUSETTS , LLC GB

2232 Jacobs Ladder Rd, Becket, MA 01223
/58
$635,000
- 3 Beds
- 3 Baths
- 2,476 Sq Ft
4 Main St, West Stockbridge, MA 01266

Don't miss this one-of-a-kind opportunity to own a commercially zoned, mixed-use property offering exceptional live/work potential in a prime in-town location along the Williams River. This uniquely designed 3-bedroom, 3-bath home includes a versatile accessory apartment, making it ideal for those seeking a combination of residential comfort and business flexibility. Enjoy water views from two

Conor Meehan STONE HOUSE PROPERTIES, LLC

4 Main St, West Stockbridge, MA 01266
/67
$474,900
- 3 Beds
- 1.5 Baths
- 1,456 Sq Ft
47 Gale Ave, Pittsfield, MA 01201

Exceptional opportunity: Fully renovated three-bedroom main residence with guest cottage...FULL DELEADING COMPLIANCE!!! This special property offers owner-occupied living and additional income. The fully renovated main residence with the separate guest cottage provides ample space for various living arrangements. Both homes are move-in ready!

Brandon White COHEN & WHITE ASSOCIATES

47 Gale Ave, Pittsfield, MA 01201
/65
$899,900 Open Sun 10:30AM - 12:30PM
- 6 Beds
- 4 Baths
- 3,818 Sq Ft
108 Berkshire Dr, Williamstown, MA 01267

A rare chance to own two attached full size charming houses in one of the most coveted neighborhoods! Abuts 30 acres of conservation land and offers direct access to The Spruces Park, Hoosic & Green River walk/ swimming area, public tennis courts, and Mohican multi-use bike/walk path! Original Home: (Built in 1953, updated in 2016) it has total privacy, deck, 2 bedrooms, 1 bath, a large living

Donna DiGrigoli DIGRIGOLI REAL ESTATE

108 Berkshire Dr, Williamstown, MA 01267
/55
$5,499,500
- 8 Beds
- 6.5 Baths
- 6,986 Sq Ft
140 Hancock Rd, Pittsfield, MA 01201

Welcome to an extraordinary opportunity on the shores of Pontoosuc Lake. This remarkable estate sets a new standard for lakefront living in Pittsfield and beyond, offering a rare combination of luxury, scale, and setting.With over 18,700 square feet of total space, including an impressive amount of garage space suitable for car collectors or hobbyists, this home provides room to live, relax, and

Cameron Volastro STONE HOUSE PROPERTIES, LLC

140 Hancock Rd, Pittsfield, MA 01201
/41
$965,000
- 3 Beds
- 3 Baths
- 4,024 Sq Ft
19 Aspen Way, Pittsfield, MA 01201

Live the lifestyle you deserve in this stunning 4-year-young detached single family condominium offering over 4,000 square feet of luxury! This 3-bed, 3-bath home features a gourmet kitchen with quartz counters, custom cooktop and hood and double ovens. Perfect for the Chef of the family. The home gym with sauna, and a spacious walkout lower level with game room and bar is the perfect space for

Victoria Standring LAMACCHIA REALTY, INC

19 Aspen Way, Pittsfield, MA 01201
/29
$649,000
- 4 Beds
- 2 Baths
- 1,850 Sq Ft
170 Stockbridge Rd, Lee, MA 01238

Charming 1930s Retreat with Water Views and Historic Charm - 170 Stockbridge Road, Lee MANestled just five minutes from both Stockbridge and the village of Lee, this beautifully restored 1930s gem offers the best of Berkshire living. Located near world-class cultural destinations--including Tanglewood, The Norman Rockwell Museum, and Jacob's Pillow--this home sits on a desirable lot overlooking

Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

170 Stockbridge Rd, Lee, MA 01238
/48
$3,750,000
- 4 Beds
- 4.5 Baths
- 5,300 Sq Ft
116 Brush Hill Rd, Great Barrington, MA 01230

Custom Built Craftsman Contemporary Home nestled in a beautifully landscaped property with an orchard, gardens and path to a seasonal brook. Inside this well appointed home you will find large rooms Vaulted ceilings, whimsical lighting, Fireplaces, Indoor pool, hot tub and sauna, radiant floor & forced air throughout. Two primary suites on main floor and 2/3 more bedrooms in the lower walkout

Mark Rosengren LANCE VERMEULEN RE, INC

116 Brush Hill Rd, Great Barrington, MA 01230
/44
$519,000
- 5 Beds
- 2.5 Baths
- 2,994 Sq Ft
100 Holmes Rd, Pittsfield, MA 01201

Classic elegance meets modern living in this stately Colonial set on a large corner lot in a highly desired neighborhood, with circular driveway for easy in and out access. Gracious entry, hardwood floors, an updated eat in kitchen plus a formal dining room with original leaded glass hutch and a formal living room. The stunning great room addition, with separate entrance and access to deck and

Victoria Standring LAMACCHIA REALTY, INC

100 Holmes Rd, Pittsfield, MA 01201
/39
$649,000
- 3 Beds
- 1.5 Baths
- 2,802 Sq Ft
40 Main St, Egremont, MA 01258

This colonial is the perfect representation of New England charm, offering a unique opportunity to experience the character of yesteryears while enjoying modern living in the heart of historic South Egremont. The inviting layout of the first floor features a spacious, open living area that seamlessly flows into a well-appointed kitchen, perfect for entertaining. A designated office space, half

Molly Thomas COMPASS MASSACHUSETTS , LLC GB

40 Main St, Egremont, MA 01258
/50
$4,985,000
- 13 Beds
- 13.5 Baths
- 9,556 Sq Ft
2 Kemble St, Lenox, MA 01240

The Kemble, a registered ''Great Estate'' built in 1881 is located in the heart of the thriving downtown Lenox business district. This classic Colonial Revival building has recently been refreshed with modern furnishings and decor, repurposed as a luxury rental property, and is being offered as a turn key operation. With grand gathering spaces, a well equipped kitchen, handsome mahogany bar, and

Cameron Volastro STONE HOUSE PROPERTIES, LLC

2 Kemble St, Lenox, MA 01240
/35
$520,000
- 3 Beds
- 2.5 Baths
- 1,922 Sq Ft
220 N Plain Rd, Great Barrington, MA 01230

An 1825 colonial has much of its original charm and features in place - wide plank floors, beamed ceiling, original hardware and fully renovated kitchen. Many new appliances, new windows, and foam insulation in the basement. The well insulated attic and walls along with a high efficiency furnace gives you modern comfort. The house is a legal two family. The Studio apartment is attached and could

Martin Albert COMPASS MASSACHUSETTS , LLC GB

220 N Plain Rd, Great Barrington, MA 01230
/82
$2,300,000
- 5 Beds
- 4.5 Baths
- 4,842 Sq Ft
173 Hillsdale Rd, Egremont, MA 01230

Nestled in a secluded, serene setting and surrounded by lush gardens, fruit trees, wildlife and protected land on three sides, this one-of-a-kind, custom-built home offers extraordinary privacy and tranquility. Crafted using wood milled directly from the property, this rustic yet contemporary home boasts a wealth of unique details that highlight exceptional craftsmanship and timeless beauty.

Robert Cohen eXp REALTY

173 Hillsdale Rd, Egremont, MA 01230
/84
$2,399,990
- 6 Beds
- 5.5 Baths
- 6,000 Sq Ft
141 Stevens Lake Way, Monterey, MA 01245

Discover Stevens Lake! This incredible property offers you a lifestyle that is unmatched in the modern world. The residence is perched overlooking the lake to experience spectacular sunrises. Entering from the garage there is a mud/laundry room which opens to the kitchen fit for any Chef. The kitchen features granite counters, Subzero and Viking appliances, a large pantry with an additional

Derek Strzepa NOCHER REALTY

141 Stevens Lake Way, Monterey, MA 01245
/21
$449,900
- 3 Beds
- 2 Baths
- 2,200 Sq Ft
1828 E Otis Rd, Otis, MA 01253

Turnkey income property, vacation retreat, or multi-generational haven! This beautifully updated 3-bed, 2-bath home with a fully equipped in-law apartment offers flexibility for rental income, extended family, or guest space. Proven short-term rental with projected gross income of $100K annually when both units are rented. Inside, enjoy vaulted ceilings, hardwood floors, new appliances, and a

Meagan Albert Tier 1 Real Estate

1828 E Otis Rd, Otis, MA 01253

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