Luxury homes for sale & real estate in Berkshire County, MA

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NEW 8 HRS AGO

ABOUT THIS HOME
Luxury Home for sale in Berkshire County, MA:
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, sauna, 8-seat hi-def theater, wine cellar, massage room, en suite bedroom/office and a soda fountain. Elegant outdoor living includes heated gunite saltwater pool/spa, firepit, pool house with guest suite and fully equipped kitchen. Heated driveway and garage. Near Lenox, Tanglewood and Berkshire art

$4,950,000

7 beds8.5 baths7,073 sq ft

1 Pinecroft Dr, Lenox, MA 01240

Turnkey home • Wet bar • Gated estate

ABOUT THIS HOME
Luxury Home for sale in Berkshire County, MA:
Nestled in the lovely gated community of Woodmont Estates, this magnificent Georgian Schultz-designed home offers five bedrooms and five baths, with effortless access to all the Berkshires have to offer. Step through the elegant front entrance into a grand foyer featuring an open stairway, flanked by a formal dining room and spacious living room. Continue on to the expansive chef's kitchen, complete with a large center island and sun-filled breakfast area. Upstairs, the second floor showcases generously sized bedrooms, including a luxurious primary suite with its own private office area. Outdoors, enjoy a stunning wraparound deck overlooking the in-ground pool—perfect for entertainmen

$1,290,000

5 beds4.5 baths3,979 sq ft

10 Eastbrook Ln, Pittsfield, MA 01201

Gated community • Outdoor fireplace • In-ground pool

ABOUT THIS HOME
Luxury Home for sale in Berkshire County, MA:
Spectacular 1896 Victorian on The Hill, completely and stylishly renovated in 2025! This six-bedroom beauty seamlessly blends original floors and grand woodwork with all-new, high-efficiency systems. Key 2025 updates include full insulation, exterior paint and two new upstairs luxury baths. 2024 brought fully ducted Air Source Heat Pumps (central AC/heating) and new windows. A 2023 heat pump water heater, powder bath, and fence complete the efficiency package. Features include an updated kitchen, oversized fireplace foyer, office with separate entrance and a private garden oasis. Located moments from downtown Great Barrington's dining/theatre and Lake Mansfield. A perfect, in-town gem&mdash

$1,995,000

6 beds2.5 baths4,138 sq ft

32 Benton Ave, Great Barrington, MA 01230

Grand woodwork • Two new luxury baths • Original floors

$1,200,000

5 beds3 baths3,328 sq ft

3 Pleasant View Dr, Great Barrington, MA 01230

6 acre lot • 2 garage spots • Built 1956

ABOUT THIS HOME
Luxury Home for sale in Berkshire County, MA:
Modern country living at its finest—crafted with exceptional quality, refined taste, and a true sense of warmth. A dramatic double-height entry and living room create a seamless dialogue with the surrounding landscape while offering the comfort of home. The main level features an open-concept kitchen, living, and dining area, anchored on one side by the primary suite and on the other by a two-bedroom guest wing. An oversized two-car garage, generous boot room, and laundry complete this level. Upstairs, a spacious flex loft with full bath and custom sauna provides an inviting retreat. Remarkably comfortable for such soaring volumes, the home offers spaces equally suited for reflection

$3,850,000

4 beds3.5 baths4,000 sq ft

21A Interlaken Rd, Stockbridge, MA 01262

Custom sauna • Open-concept kitchen • Double-height entry

Property at 1130 East Rd, Richmond, MA 01254, 4 beds, 1.5 baths

$1,850,000

4 beds1.5 baths3,084 sq ft

1130 East Rd, Richmond, MA 01254

Property at 4 Stoneledge Rd, Lenox, MA 01240, 4 beds, 4.5 baths

$1,100,000

4 beds4.5 baths2,995 sq ft

4 Stoneledge Rd, Lenox, MA 01240

Property at 45 Forest St, Lee, MA 01238, 12 beds, 7 baths

$1,399,900

12 beds7 baths7,956 sq ft

45 Forest St, Lee, MA 01238

Property at 764 East Hill Rd, New Marlboro, MA 01230, 5 beds, 5.5 baths

$4,995,000

5 beds5.5 baths5,002 sq ft

764 East Hill Rd, New Marlboro, MA 01230

Property at 69 Gravesleigh Ter, Pittsfield, MA 01201, 4 beds, 2.5 baths

$888,800

4 beds2.5 baths3,005 sq ft

69 Gravesleigh Ter, Pittsfield, MA 01201

Property at 302A Egremont Plain Rd, Egremont, MA 01230, 4 beds, 5 baths

$2,250,000

4 beds5 baths4,846 sq ft

302A Egremont Plain Rd, Egremont, MA 01230

Property at 55 Crystal St, Lenox, MA 01240, 10 beds, 10.5 baths

$1,995,000

10 beds10.5 baths11,608 sq ft

55 Crystal St, Lenox, MA 01240

Property at 40 E Alford Rd, West Stockbridge, MA 01266, 4 beds, 3.5 baths

$3,750,000

4 beds3.5 baths3,225 sq ft

40 E Alford Rd, West Stockbridge, MA 01266

Property at 65 Adsit Crosby Rd, New Marlborough, MA 01230, 3 beds, 4 baths

$1,895,000

3 beds4 baths3,600 sq ft

65 Adsit Crosby Rd, New Marlborough, MA 01230

Property at 9 October Hill Dr, Lenox, MA 01240, 4 beds, 4.5 baths

$1,695,000

4 beds4.5 baths3,991 sq ft

9 October Hill Dr, Lenox, MA 01240

Property at 30 East Rd, West Stockbridge, MA 01266, 7 beds, 7.5 baths

$13,500,000

7 beds7.5 baths10,429 sq ft

30 East Rd, West Stockbridge, MA 01266

Property at 520 State Rd #402, North Adams, MA 01247, 2 beds, 2 baths

$1,340,000

2 beds2 baths2,110 sq ft

520 State Rd #402, North Adams, MA 01247

Property at 276 Great Barrington Rd, West Stockbridge, MA 01266, 3 beds, 3 baths

$1,100,000

3 beds3 baths2,002 sq ft

276 Great Barrington Rd, West Stockbridge, MA 01266

Property at 2650 Swamp Rd, Richmond, MA 01254, 5 beds, 7.5 baths

$3,750,000

5 beds7.5 baths6,022 sq ft

2650 Swamp Rd, Richmond, MA 01254

Property at 6 Thrushwood Ln, Great Barrington, MA 01230, 5 beds, 4 baths

$1,475,000

5 beds4 baths4,200 sq ft

6 Thrushwood Ln, Great Barrington, MA 01230

Property at 353 State Rd, Great Barrington, MA 01230, 5 beds, 3 baths

$1,450,000

5 beds3 baths2,688 sq ft

353 State Rd, Great Barrington, MA 01230

Property at 60 Old Cheshire Rd, Lanesborough, MA 01237, 4 beds, 4 baths

$2,500,000

4 beds4 baths6,100 sq ft

60 Old Cheshire Rd, Lanesborough, MA 01237

Property at 141 Stevens Lake Way, Great Barrington, MA 01230, 6 beds, 5.5 baths

$2,275,000

6 beds5.5 baths6,000 sq ft

141 Stevens Lake Way, Great Barrington, MA 01230

Property at 1030 Simonds Rd, Williamstown, MA 01267, 5 beds, 4.5 baths

$995,000

5 beds4.5 baths4,102 sq ft

1030 Simonds Rd, Williamstown, MA 01267

Property at 905 West Rd, Great Barrington, MA 01230, 3 beds, 2.5 baths

$1,250,000

3 beds2.5 baths2,204 sq ft

905 West Rd, Great Barrington, MA 01230

Property at 560 Stockbridge Rd, Lee, MA 01238, 6 beds, 9 baths

$899,000

6 beds9 baths4,652 sq ft

560 Stockbridge Rd, Lee, MA 01238

Property at 61 Tor Court Ct, Pittsfield, MA 01201, 3 beds, 2 baths

$1,395,000

3 beds2 baths1,728 sq ft

61 Tor Court Ct, Pittsfield, MA 01201

Property at 65 Crofut St, Pittsfield, MA 01201, 5 beds, 4.5 baths

$1,350,000

5 beds4.5 baths4,948 sq ft

65 Crofut St, Pittsfield, MA 01201

Property at 257 W Mountain Rd, Lenox, MA 01240, 3 beds, 2.5 baths

$995,000

3 beds2.5 baths2,844 sq ft

257 W Mountain Rd, Lenox, MA 01240

Property at 14 Copper Beech Ln, Great Barrington, MA 01230, 3 beds, 2.5 baths

$925,000

3 beds2.5 baths2,062 sq ft

14 Copper Beech Ln, Great Barrington, MA 01230

Property at 211 Cottage St, Housatonic, MA 01236, 3 beds, 3 baths

$875,000

3 beds3 baths3,204 sq ft

211 Cottage St, Housatonic, MA 01236

Property at 1020 Cascade St, Pittsfield, MA 01201, 3 beds, 3 baths

$1,170,000

3 beds3 baths2,662 sq ft

1020 Cascade St, Pittsfield, MA 01201

Property at 94 West Ave, Great Barrington, MA 01230, 4 beds, 3.5 baths

$1,295,000

4 beds3.5 baths3,194 sq ft

94 West Ave, Great Barrington, MA 01230

Property at 9 Bott Hill Rd, Egremont, MA 01258, 4 beds, 3.5 baths

$1,685,000

4 beds3.5 baths3,200 sq ft

9 Bott Hill Rd, Egremont, MA 01258

Property at 8 Webster Rd, Tyringham, MA 01264, 7 beds, 6.5 baths

$4,600,000

7 beds6.5 baths5,885 sq ft

8 Webster Rd, Tyringham, MA 01264

Property at 327 Chester Rd, Becket, MA 01223, 2 beds, 2.5 baths

$2,650,000

2 beds2.5 baths1,183 sq ft

327 Chester Rd, Becket, MA 01223

Property at 228 East St, Great Barrington, MA 01230, 5 beds, 4.5 baths

$1,390,000

5 beds4.5 baths2,900 sq ft

228 East St, Great Barrington, MA 01230

Property at 5 Crofut St, Pittsfield, MA 01201, 5 beds, 3.5 baths

$889,900

5 beds3.5 baths3,370 sq ft

5 Crofut St, Pittsfield, MA 01201

Property at 11 Prospect St, Great Barrington, MA 01230, 4 beds, 2.5 baths

$889,000

4 beds2.5 baths2,114 sq ft

11 Prospect St, Great Barrington, MA 01230

Property at 615 Laurel St, Lee, MA 01238, 15 beds, 15 baths

$3,599,000

15 beds15 baths11,945 sq ft

615 Laurel St, Lee, MA 01238

Property at 319 Under Mountain Rd, Lenox, MA 01240, 7 beds, 7 baths

$4,995,000

7 beds7 baths13,261 sq ft

319 Under Mountain Rd, Lenox, MA 01240

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Luxury Homes for Sale in Berkshire County

There are currently 140 luxury homes for sale in Berkshire County at a median listing price of $470K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Berkshire County stay on the market for 77 days. This map is refreshed with the newest listings in Berkshire County every 15 minutes.

In the past month, 182 homes have been sold in Berkshire County. In addition to houses in Berkshire County, there were also 87 condos, 5 townhouses, and 83 multi-family units for sale in Berkshire County last month. Find your dream home in Berkshire County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Berkshire County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Berkshire County. If you're looking to sell your home in the Berkshire County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Berkshire County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Luxury homes for sale & real estate in Berkshire County, MA

Luxury Homes for Sale in Berkshire County

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