Homes for Sale in Berkshire County MA with 5-Bedrooms

/48
$974,999
- 6 Beds
- 9 Baths
- 4,652 Sq Ft
560 Stockbridge Rd, Lee, MA 01238

Set on just over seven acres between Lee and Stockbridge, this c.1850 Greek Revival delivers classic Berkshire character with real scale. Nearly 4,700 square feet with a gracious flow, tall windows, and preserved period details. Every bedroom offers an en suite, creating an easy setup for hosting family and friends. Common spaces include a welcoming foyer, two living rooms, a formal dining room,

Cameron Volastro WILLIAM PITT SOTHEBY'S - LENOX

560 Stockbridge Rd, Lee, MA 01238
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/85
$4,250,000
- 5 Beds
- 8 Baths
- 6,378 Sq Ft
58 Round Hill Rd, Great Barrington, MA 01230

Come relax amid sweeping pastoral and mountain views in this exceptional retreat designed for both entertaining and everyday comfort. The impressive great room, anchored by a massive stone fireplace, offers a welcoming focal point and flows into a spacious well-designed kitchen/dining area. A screened porch with fireplace overlooks the pool and rolling landscape, creating a seamless

Sheila Thunfors STONE HOUSE PROPERTIES, LLC

58 Round Hill Rd, Great Barrington, MA 01230
/49
$844,000
- 6 Beds
- 4 Baths
- 3,818 Sq Ft
108 Berkshire Dr, Williamstown, MA 01267

This exceptional home is ideally located within walking distance of the town center and Williams College. Set alongside protected conservation land, the property offers a rare blend of convenience, privacy, and natural beauty and is also located in a highly desirable Williamstown neighborhood. The property has direct backyard access to Lower Linear Park walking trails, the Mohican Trail bike

Donna DiGrigoli DIGRIGOLI REAL ESTATE

108 Berkshire Dr, Williamstown, MA 01267
/37
$539,900
- 5 Beds
- 3.5 Baths
- 3,307 Sq Ft
867 Notch Rd, Cheshire, MA 01225

Home on a dream lot--over 7 secluded acres framed by mountains and backing to the Chalet Wildlife Management Area (7,000+ acres of protected state land). Enjoy total privacy, wide-open views, and dark-night skies away from city lights. Step inside to a grand entrance with a glistening chandelier. The main level features a flowing layout: a spacious kitchen with sufficient storage and generous

Mariah Worth LAMACCHIA REALTY, INC

867 Notch Rd, Cheshire, MA 01225
/60
$4,950,000
- 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 primary en suite bedrooms with cedar closets. Lower level: gym,

Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

1 Pinecroft Dr, Lenox, MA 01240
/22
$280,000
- 6 Beds
- 2 Baths
- 2,214 Sq Ft
3 Pleasant St, Pittsfield, MA 01201

Two Family Flat fully rented in the Morningside Neighborhood! Each unit has three bedrooms and one bathroom. Updated kitchens and hardwood floors. Heat and hot water included. Washer and dryer hookups in the basement. Fully fenced in yard on a corner lot. Well maintained and ready for its new owner!

Derek Strzepa NOCHER REALTY

3 Pleasant St, Pittsfield, MA 01201
/42
$1,399,900
- 12 Beds
- 7 Baths
- 7,956 Sq Ft
45 Forest St, Lee, MA 01238

This stunning 6-family home sits on 1.5 acres, a large lot that goes from Forest St to Silver St, a convenient location with easy access to the Mass Pike and just a couple minutes away from the Lee Outlets. This multi-family consists of 3 two-bedroom units, 2 one-bedroom units, and a 4 bedroom 2 bath unit. The large unit offers a welcoming front porch, living room, eat-in kitchen, full bath and

Maria Liccardi Kempf-Vanderburgh Realty Consultants, Inc.

45 Forest St, Lee, MA 01238
/32
$1,395,000
- 5 Beds
- 4 Baths
- 4,200 Sq Ft
6 Thrushwood Ln, Great Barrington, MA 01230

MOTIVATED SELLER; WILLING TO NEGOTIATE ON UPGRADES AND IMPROVEMENTS. Indulge in refined Berkshire living on an exclusive cul-de-sac, where effortless HOA services complement this exquisite new construction. Offering 4,200 sq ft of thoughtfully designed, environmentally conscious living less than a mile from downtown Great Barrington, this home is the perfect modern retreat. Enter through a

Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

6 Thrushwood Ln, Great Barrington, MA 01230
/35
$275,000
- 7 Beds
- 3 Baths
- 2,664 Sq Ft
86 W Main St, North Adams, MA 01247

Turnkey 3-family in the heart of North Adams! Features two 3-bedroom, 1-bath units and a renovated basement studio. 2nd floor unit is vacant with potential rent $1,400–$1,600/month. 3rd floor unit tenant moving out; after updates can rent $1,600/month. Basement studio rented $1,000/month. All units separately metered; tenants pay all utilities except water. Large unfinished attic (~1,200 sq ft)

Monette Valliere Keller Williams Elite

86 W Main St, North Adams, MA 01247
/50
$7,975,000
- 8 Beds
- 6.5 Baths
- 9,364 Sq Ft
399 Under Mountain Rd, Lenox, MA 01240

Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, walnut paneling and pocket

Molly Thomas COMPASS MASSACHUSETTS , LLC GB

399 Under Mountain Rd, Lenox, MA 01240
/55
$4,300,000
- 7 Beds
- 8 Baths
- 5,885 Sq Ft
8 Webster Rd, Tyringham, MA 01264

Brooke Astor's COBBLE HOUSEWhere Land, Light, and Legacy ConvergeTYRINGHAM VALLEY BERKSHIRE COUNTY MASSACHUSETTS$4,300,0005,885 square feet7 bedrooms8.5 bathrooms27.9 private acres1909 Harrie T. Lindeberg design2,321 +/- feet road frontageThe Valley That Time ForgotThe drive through Tyringham Valley never fails to quiet the soul. Past stone walls that have marked these fields for centuries,

John Burns WILLIAM PITT SOTHEBY'S - GT BARRINGTON

8 Webster Rd, Tyringham, MA 01264
/68
$1,350,000
- 5 Beds
- 4.5 Baths
- 4,948 Sq Ft
65 Crofut St, Pittsfield, MA 01201

Designed in 1929 by noted architect Henry Seaver (Berkshire Museum, Lenox Town Hall), this distinguished Georgian Colonial was once the centerpiece of Pittsfield's social scene. The home preserves exquisite 18th-century details - mantels, wainscoting, and finely crafted woodwork salvaged from two of the city's earliest residences, making it a living piece of Berkshire history. Set back on 2.5

Conor Meehan STONE HOUSE PROPERTIES, LLC

65 Crofut St, Pittsfield, MA 01201
/73
$889,900
- 5 Beds
- 3.5 Baths
- 3,370 Sq Ft
5 Crofut St, Pittsfield, MA 01201

Pride of ownership reasonates through this disctinctive Georgian-style brick home proudly set atop a hill in this coveted enclave of stately residences. Live on this historic Crofut St. near the esteemed Pittsfield Country Club, BUpstreet Cultural District and is ideally just minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional

Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

5 Crofut St, Pittsfield, MA 01201
/64
$1,199,800
- 9 Beds
- 4.5 Baths
- 5,319 Sq Ft
5 Crofut St, Pittsfield, MA 01201

Pride of ownership reasonates through this disctinctive Georgian-style brick home proudly set atop a hill in this coveted enclave of stately residences. Live on this historic Crofut St. near the esteemed Pittsfield Country Club, Upstreet Cultural District and is ideally just minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional

Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

5 Crofut St, Pittsfield, MA 01201
/43
$1,290,000
- 5 Beds
- 4.5 Baths
- 2,900 Sq Ft
228 East St, Great Barrington, MA 01230

Great Barrington A masterful rebuild with reverence for Great Barrington's past and a bold reimagining for modern living. This 5-bedroom, 4-1/2 bath colonial sits in-town and blends historic charm with contemporary luxury for effortless, years-long comfort.Property Highlights5 Bedrooms | 4 Full Baths + 1 Half Bath**Complex rebuild from the ground up** - preserved nod to the town's heritage with a

Eric Steuernagle FAIRGROUND REAL ESTATE, INC

228 East St, Great Barrington, MA 01230
/55
$3,500,000
- 5 Beds
- 6.5 Baths
- 6,088 Sq Ft
110 Alford Rd, Great Barrington, MA 01230

Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure.Inside,

Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

110 Alford Rd, Great Barrington, MA 01230
/80
$995,000
- 5 Beds
- 4.5 Baths
- 4,102 Sq Ft
1030 Simonds Rd, Williamstown, MA 01267

Escape to your own private retreat in Williamstown, 'The Village Beautiful.' This spacious 5-bedroom, 4.5-bath home sits on 7.5 private acres and offers over 4,000 sq. ft. of living space throughout three levels, plus a finished basement with full bath and sauna. This home blends classic and modern features: exposed wood beam ceilings and a new, private primary suite with soaking tub. The home

Carrie Swift Heck COMPASS MASSACHUSETTS , LLC GB

1030 Simonds Rd, Williamstown, MA 01267
/33
$464,000
- 5 Beds
- 2 Baths
- 3,062 Sq Ft
103 Holmes Rd, Hinsdale, MA 01235

The Woolen House stands as a rare piece of prestigious Hinsdale history. Once the home of the Woolen Mill superintendent, it has been fully reimagined for modern living. The craftsmanship is unmistakable: original woodwork, 16 inch brick construction, and a sense of permanence rarely found today. Inside, five bedrooms, two full bathrooms, a spacious laundry, and a versatile first floor room offer

Harmony Edwards KELLER WILLIAMS REALTY

103 Holmes Rd, Hinsdale, MA 01235
/43
$199,900
- 6 Beds
- 2 Baths
- 2,749 Sq Ft
24 Franklin St, North Adams, MA 01247

Come see this 6 bed 3 bath restoration. Built in 1900 it has undergone extensive repairs and updates for modern living. New 200amp electricNew high efficiency on demand heat and hot water boilerNewer flooring in bedrooms and kitchenGas range Farmhouse sink Ample storage in full size basement and atticUnique setup great for large family, guests, or AirbnbAll of the heavy lifting has been done.

Donna Thomas DONNA THOMAS REALTY

24 Franklin St, North Adams, MA 01247
/45
$3,900,000
- 10 Beds
- 5.5 Baths
- 7,864 Sq Ft
535 Main Rd, Monterey, MA 01245

Welcome home to NEWGRANGE. 1920's era Manor House with lake frontage on Lake Garfield. Over 10,000 square feet of living on 7.7 Acres. Complete the restoration and enjoy original Stone Fireplaces, comfortable Living spaces, formal Dining and 10 Bedrooms. Write that novel in the paneled Office, Library or Sunroom, create delicacies in the Country Kitchen, or shoot a round of pool in the Billiard

Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

535 Main Rd, Monterey, MA 01245
/77
$4,500,000
- 5 Beds
- 5.5 Baths
- 4,027 Sq Ft
19 Roberts Rd, Sandisfield, MA 01255

Introducing  FREE QUARTER FARMNearly 1,500 Acres | Sandisfield, the Southern Berkshires | $4,500,000Miles of private trails for hiking, hunting, fishing, horseback riding - your own wilderness preserve134+ acres not in conservation with 1,489 feet of road frontage - craft your legacy5BR/5BA timeless home built for this wildly beautiful placeStand between your home, overlooking your private

Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

19 Roberts Rd, Sandisfield, MA 01255
/8
$449,000
- 8 Beds
- 4 Baths
- 2,657 Sq Ft
180 Center St, Lee, MA 01238

Huge price adjustment! Discover an exceptional investment opportunity to own two duplex homes on a single parcel, perfect for investors looking for a practical investment in the town of Lee. Four units total, these properties are ideal for generating consistent rental income. Close to downtown, shopping, major employers as well as banking and all popular Berkshire attractions. Tenants enjoy

Tim Gallagher STONE HOUSE PROPERTIES, LLC

180 Center St, Lee, MA 01238
/20
$3,599,000
- 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
/55
$649,000
- 5 Beds
- 2.5 Baths
- 2,750 Sq Ft
168 Main St, Sheffield, MA 01257

Historic village living at its finest. This expansive Turn-of-the-Century Sheffield home is rich with original detail, from its warm wood floors to a magnificent fieldstone fireplace. The property boasts a large, private yard, offering ample space for gardening, recreation, or outdoor entertainment. A substantial barn on the property provides excellent potential for a workshop, studio, or extra

Tony Segalla WILLIAM RAVEIS - BERKSHIRE

168 Main St, Sheffield, MA 01257
/60
$1,330,000
- 16 Beds
- 10 Baths
- 8,870 Sq Ft
6 Manville St, Great Barrington, MA 01230

A prime investment opportunity in the heart of downtown Great Barrington. This 10-unit residential property features a desirable mix of six spacious two-bedroom apartments and four one-bedroom units. The two-bedroom apartments are particularly appealing, all offering private balconies and fireplaces, with three of these premium units also including formal dining rooms and Jack-and-Jill style

Tony Segalla WILLIAM RAVEIS - BERKSHIRE

6 Manville St, Great Barrington, MA 01230
/69
$699,000
- 5 Beds
- 4.5 Baths
- 3,381 Sq Ft
33 Alpine Trail, Pittsfield, MA 01201

Beautiful townhouse located in the Pines at Bousquet with picturesque mountain views! The main level boasts vaulted ceilings with open bright common areas, great room with wood flooring and gas fireplace, updated kitchen, dining room with views, primary bedroom with newly renovated en suite bath, oversized garage, half bathroom and private screened porch and deck to take in the fresh air and

Cortney Dupont COHEN & WHITE ASSOCIATES

33 Alpine Trail, Pittsfield, MA 01201
/33
$1,500,000
- 7 Beds
- 7.5 Baths
- 4,000 Sq Ft
802 State Rd, Richmond, MA 01254

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare blend of colonial charm and modern equestrian excellence. Spanning 11+ bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence, three enchanting cottages, and the potential to include the region's premier full-service equestrian facility (see

Diana Bisselle William Pitt Sotheby's Int'l

802 State Rd, Richmond, MA 01254
/30
$400,000
- 5 Beds
- 2 Baths
- 2,858 Sq Ft
6 Crandall St, Adams, MA 01220

Step into this timeless elegance with this spacious 5-bedroom, 2-bath Colonial built in 1900 in a historic district. Full of classic charm inside and out, including original architectural details, hardwood floors, wide trim, and tall ceilings. Two full staircases, a formal front staircase, and a more private back staircase that adds historic charm and functionality. The main floor boasts of

Barbara DeMers NOCHER REALTY

6 Crandall St, Adams, MA 01220
/40
$970,000
- 5 Beds
- 4.5 Baths
- 3,024 Sq Ft
60 Parsley Ln, Sheffield, MA 01257

Nestled at the end of a quiet country cul-de-sac, this newly built 5-bedroom, 4.5-bath home embodies refined country living. A dramatic primary suite offers dual walk-in closets and a spa-inspired bath with soaking tub, while a first-floor ensuite bedroom enhances comfort and flexibility. The gas fireplace living room and chef's kitchen create a seamless flow for entertaining, extending to a

Vashti Poor WILLIAM RAVEIS - BERKSHIRE

60 Parsley Ln, Sheffield, MA 01257
/52
$1,675,000
- 12 Beds
- 7 Baths
- 8,881 Sq Ft
29 Main St, West Stockbridge, MA 01266

Step into a piece of history with the once Iconic Card Lake Inn Tavern, now transformed into a stunning residential haven in the heart of downtown West Stockbridge. This property offers not only a prime location but also an exceptional living experience, combining modern amenities with charming historic character. The building houses six completely renovated high-end apartments, each thoughtfully

Suzann Ward HOUSATONIC REAL ESTATE

29 Main St, West Stockbridge, MA 01266
/41
$1,750,000
- 22 Beds
- 21 Baths
- 9,018 Sq Ft
885 Washington Mountain Rd, Washington, MA 01223

The Possibilities are endless! Family Compound & Retreat ! Hotel, Wedding Venue, Campgrounds, Cross Country Skiing Trails or Family Compound, bring your imagination and bring Buck Steep Manor back to Life! Five Buildings and many Cabins amid this 350-acre Estate. The Manor House 25 rooms the Lodge 19 rooms the Dutch Colonial Barn 5 rooms the Cottage 10 rooms The Antique Carriage Barn Hall 99pl

Joy Salvini RE/MAX Compass

885 Washington Mountain Rd, Washington, MA 01223
/66
$6,850,000
- 5 Beds
- 3.5 Baths
- 3,474 Sq Ft
77 Seekonk Cross Rd, Great Barrington, MA 01230

Welcome to Meadow Wood This elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lily pond, terraces, pastoral views, and privacy. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/

Elvia Gignoux WILLIAM PITT SOTHEBY'S - SALISBURY

77 Seekonk Cross Rd, Great Barrington, MA 01230
/58
$675,000
- 7 Beds
- 6.5 Baths
- 3,684 Sq Ft
3 Lake Buel Rd, Great Barrington, MA 01230

Tucked into the rolling hills of Great Barrington, The Turning Point has been welcoming travelers for more than two centuries. In the 1800s, stagecoaches once paused here--horses rested, stories were traded, and journeys quietly shifted direction. That spirit of arrival still lingers.Now spanning 3,600 square feet, this historic Berkshire retreat has lived many lives: a bustling inn, a beloved

Lance Vermeulen LANCE VERMEULEN RE, INC

3 Lake Buel Rd, Great Barrington, MA 01230
/63
$2,495,000
- 5 Beds
- 3.5 Baths
- 6,254 Sq Ft
84 Undermountain Rd, Egremont, MA 01230

Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it

Lance Vermeulen LANCE VERMEULEN RE, INC

84 Undermountain Rd, Egremont, MA 01230
/11
$799,000
- 6 Beds
- 5 Baths
- 4,016 Sq Ft
129 W Shore Rd, Otis, MA 01253

Otis Reservoir Deeded Access is steps away from this versatile property. Four units primarily used, on a casual basis, as vacation rentals with nightly rates ranging from $140 to $171. Current retiring owner has set the stage for the next owner to grow a highly profitable venture. Most furniture, fixtures and supplies convey so the new owner can hit the ground running. Portions of the

Karen Chenausky Cetto Real Estate

129 W Shore Rd, Otis, MA 01253
/47
$7,250,000 New Construction
- 6 Beds
- 7 Baths
- 13,175 Sq Ft
209 Blue Hill Rd, Great Barrington, MA 01230

A rare French Manor estate gracing one of South Berkshire's most scenic and sought-after country roads, this extraordinary 45+/- acre sanctuary offers unmatched privacy, panoramic mountain views, and a setting of timeless beauty. Bordering protected state forest, the property unfolds across rolling meadows, tranquil ponds, and a gently flowing brook—creating a secluded retreat that feels worlds

Mauren White-Kirkby Berkshire Hathaway Homeservice

209 Blue Hill Rd, Great Barrington, MA 01230
/13
$89,000 New Construction
- 6 Beds
- 1,530 Sq Ft
336 Walnut St, North Adams, MA 01247

Unique investment opportunity in The Berkshires with this completely gutted home, ready to be restored. With its walls stripped down to the studs, this property offers a blank canvas, inviting you to design a stunning three floor single-family residence or transform it back into a charming three-family investment property. Outside you will find a one-car garage and a spacious lot, bordered by

Mariah Worth LAMACCHIA REALTY, INC

336 Walnut St, North Adams, MA 01247
/35
$284,900
- 6 Beds
- 2 Baths
- 2,840 Sq Ft
10-12 Richmond St, Adams, MA 01220

Come put the finishing touches on this beautiful renovation project today! Most of the work has already been completed, this is your chance for a quick project. Kitchens and bathrooms have been renovated with extensive tile work. Fresh flooring and paint. Stainless steel appliances. Come see this spacious 2-unit today!

Benjamin Hause Keller Williams Realty North Central

10-12 Richmond St, Adams, MA 01220
/28
$149,900
- 6 Beds
- 2 Baths
- 2,132 Sq Ft
516-518 Union St, North Adams, MA 01247

Come put your finishing touches on this large 6 bed, 2 bath multifamily! Significant work has already been completed. This is your chance to bring a great project over the finish line!

Benjamin Hause Keller Williams Realty North Central

516-518 Union St, North Adams, MA 01247
/31
$199,900
- 7 Beds
- 4.5 Baths
- 3,672 Sq Ft
15 Buel St, Pittsfield, MA 01201

Come finish the renovation of this expansive 7 bedroom home! This project is ready for your vision and creativity to bring it to fruition! Don't miss this opportunity!

Benjamin Hause Keller Williams Realty North Central

15 Buel St, Pittsfield, MA 01201

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