Homes with Pools for Sale in Berkshire County, MA

720 homes

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ABOUT THIS HOME
Home with a Pool for sale in Berkshire County, MA:
Imagine waking up in a sun-splashed home just steps from Great Barrington's lively Main Street—where every café, bookstore, and gallery feels like an extension of your neighborhood. This second-floor floor-through condo is more than a home; it's a canvas for your life. Over 1,800 sq. ft. of expansive living space unfolds with towering ceilings, oversized windows, and graceful arched doorways that evoke another era. Every detail—from the textured walls to the light pouring in at all hours—creates a sense of romance and possibility. The home is thoughtfully divided: one wing offers a spacious bedroom and lounge with guest alcove, while the other wing hosts a dining ar

$425,000

2 beds1.5 baths1,860 sq ft

264 Main St Unit B, Great Barrington, MA 01230

Towering ceilings • Spacious bedroom • Arched doorways

ABOUT THIS HOME
Home with a Pool for sale in Berkshire County, MA:
Welcome to this classic 1950s ranch on East New Lenox Road — full of character and comfort. Featuring three bedrooms and one full bath, this home showcases beautiful wood floors, freshly painted interiors, and that timeless New England charm that never goes out of style. Enjoy the added versatility of a three-season porch connecting to the attached two-car garage, perfect for morning coffee or an afternoon read overlooking the fenced-in backyard. Whether you’re seeking your first home, downsizing, or a Berkshire getaway, this property offers both simplicity and convenience. Located close to downtown Lenox, Tanglewood, and all the cultural and outdoor attractions that make Berksh

$370,000

3 beds1 bath1,144 sq ft

16 E New Lenox Rd, Lenox, MA 01240

Fenced in backyard • Three season porch • Close to tanglewood

ABOUT THIS HOME
Home with a Pool for sale in Berkshire County, MA:
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 covered portico into a soaring cathedral-ceiling great room filled with natural light and serene woodland views. A wonderful screened porch expands the living space for peaceful mornings or easy entertaining. The open layout seamlessly connects the living, dining, and chef's kitchen, featuring premium app

$1,475,000

5 beds4 baths4,200 sq ft

6 Thrushwood Ln, Great Barrington, MA 01230

Expansive windows • Screened porch • Exclusive cul-de-sac

ABOUT THIS HOME
Home with a Pool for sale in Berkshire County, MA:
Adams! Good location with a walk to downtown. This 3 bedroom, 1 bath home offers large rooms, plenty of storage space, back porch entry and a front, open sitting porch. Yard with Greylock Mountain Views and a 1-car garage! Close to Ashuwillticook Bike trail & public bus transportation.

$225,000

3 beds1 bath1,400 sq ft

1 Godek St, Adams, MA 01220

Bike trail • Public bus route • Front sitting porch

ABOUT THIS HOME
Home with a Pool for sale in Berkshire County, MA:
The Woodlands — A Private 74-Acre Retreat in Great Barrington! A rare opportunity to own a private and picturesque Berkshire retreat in the heart of Great Barrington. Set on seventy-four acres of meadow, orchard, and forest, The Woodlands offers a refuge of uncommon scale and serenity—just two minutes from Ski Butternut and five minutes to downtown Great Barrington's restaurants, shops, and cultural life. The property abuts the Thomas & Palmer Brook Reserve, a Berkshire Natural Resources Council preserve spanning more than 300 acres of protected woodland and scenic trails, extending your own land into a vast network of wild beauty. A long, tree-lined drive winds through

$1,450,000

5 beds3 baths2,688 sq ft

353 State Rd, Great Barrington, MA 01230

Hand laid stone wall • 74.07 acre lot • 5 garage spots

Property at 12 Barrington Pl, Great Barrington, MA 01230, 4 beds, 2 baths

$799,000

4 beds2 baths2,105 sq ft

12 Barrington Pl, Great Barrington, MA 01230

Property at 25 Ashley St, Pittsfield, MA 01201, 4 beds, 2 baths

$204,900

4 beds2 baths1,496 sq ft

25 Ashley St, Pittsfield, MA 01201

Property at 9102 Mountainside Dr, Hancock, MA 01237, 3 beds, 3 baths

$689,000

3 beds3 baths1,968 sq ft

9102 Mountainside Dr, Hancock, MA 01237

Property at 447 Notch Rd, North Adams, MA 01247, 1 bed, 1 bath

$199,000

1 bed1 bath304 sq ft

447 Notch Rd, North Adams, MA 01247

Property at 1 Bulkley St, Williamstown, MA 01267, 3 beds, 3 baths

$629,000

3 beds3 baths1,779 sq ft

1 Bulkley St, Williamstown, MA 01267

Property at 46 Housatonic St Unit 2B, Lenox, MA 01240, 2 beds, 2 baths

$650,000

2 beds2 baths1,098 sq ft

46 Housatonic St Unit 2B, Lenox, MA 01240

Property at 18 Hill Rd, Stockbridge, MA 01262, 2 beds, 1 bath

$499,000

2 beds1 bath1,015 sq ft

18 Hill Rd, Stockbridge, MA 01262

Property at 166 Berkshire School Rd, Sheffield, MA 01257, 3 beds, 2 baths

$449,000

3 beds2 baths1,670 sq ft

166 Berkshire School Rd, Sheffield, MA 01257

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 2 Devon Rd, Stockbridge, MA 01262, 1 bed, 1 bath

$485,000

1 bed1 bath1,344 sq ft

2 Devon Rd, Stockbridge, MA 01262

Property at 66 Holmes Rd, Pittsfield, MA 01201, 3 beds, 1 bath

$239,900

3 beds1 bath1,257 sq ft

66 Holmes Rd, Pittsfield, MA 01201

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 80 Mcintosh Dr, Pittsfield, MA 01201, 3 beds, 1 bath

$345,000

3 beds1 bath1,440 sq ft

80 Mcintosh Dr, Pittsfield, MA 01201

Property at 61 Seymour St, Pittsfield, MA 01201, 6 beds, 2 baths

$229,000

6 beds2 baths2,736 sq ft

61 Seymour St, Pittsfield, MA 01201

Property at 108 Church St, Cheshire, MA 01225, 4 beds, 2 baths

$159,000

4 beds2 baths1,850 sq ft

108 Church St, Cheshire, MA 01225

Property at 1 Pondview Dr Unit C3, Pittsfield, MA 01201, 2 beds, 1 bath

$219,900

2 beds1 bath1,430 sq ft

1 Pondview Dr Unit C3, Pittsfield, MA 01201

Property at 46 Lucille St, Pittsfield, MA 01201, 3 beds, 2 baths

$374,900

3 beds2 baths1,544 sq ft

46 Lucille St, Pittsfield, MA 01201

Property at 399 State Rd, Richmond, MA 01254, 3 beds, 1.5 baths

$495,000

3 beds1.5 baths1,732 sq ft

399 State Rd, Richmond, MA 01254

Property at 41 Pearl St Unit 1-2, Great Barrington, MA 01230, 4 beds, 2 baths

$525,000

4 beds2 baths1,964 sq ft

41 Pearl St Unit 1-2, 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 33-35 Hall St, North Adams, MA 01247, 5 beds, 2 baths

$279,900

5 beds2 baths2,584 sq ft

33-35 Hall St, North Adams, MA 01247

Property at 455 King Richard Dr, Becket, MA 01223, 3 beds, 1 bath

$199,000

3 beds1 bath1,404 sq ft

455 King Richard Dr, Becket, MA 01223

Property at 1070 Holmes Rd, Pittsfield, MA 01201, 3 beds, 1.5 baths

$329,900

3 beds1.5 baths1,563 sq ft

1070 Holmes Rd, Pittsfield, MA 01201

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 7 Park St, Stockbridge, MA 01262, 2 beds, 1 bath

$549,000

2 beds1 bath1,300 sq ft

7 Park St, Stockbridge, MA 01262

Property at 19 Hawthorne Rd Unit 3B Stables, Stockbridge, MA 01262, 2 beds, 3 baths

$600,000

2 beds3 baths1,870 sq ft

19 Hawthorne Rd Unit 3B Stables, Stockbridge, MA 01262

Property at 2801 State Rd, Richmond, MA 01254, 3 beds, 1 bath

$389,000

3 beds1 bath1,413 sq ft

2801 State Rd, Richmond, MA 01254

Property at 40 Roland St, Pittsfield, MA 01201, 3 beds, 1 bath

$209,900

3 beds1 bath1,486 sq ft

40 Roland St, Pittsfield, MA 01201

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 36 Glendale Rd, Stockbridge, MA 01262, 3 beds, 3 baths

$699,000

3 beds3 baths1,829 sq ft

36 Glendale Rd, Stockbridge, MA 01262

Property at 2 W Rose Ct, Great Barrington, MA 01230, 3 beds, 2.5 baths

$449,000

3 beds2.5 baths1,368 sq ft

2 W Rose Ct, Great Barrington, MA 01230

Property at 1136 Barker Rd #18, Pittsfield, MA 01201, 3 beds, 1.5 baths

$599,900

3 beds1.5 baths2,044 sq ft

1136 Barker Rd #18, Pittsfield, MA 01201

Property at 612 East New Lenox Rd, Pittsfield, MA 01201, 3 beds, 2 baths

$360,000

3 beds2 baths1,120 sq ft

612 East New Lenox Rd, Pittsfield, MA 01201

Property at 490 Kirchner Rd, Dalton, MA 01226, 4 beds, 2 baths

$560,000

4 beds2 baths3,087 sq ft

490 Kirchner Rd, Dalton, MA 01226

Property at 20 Greenway St, Pittsfield, MA 01201, 3 beds, 1.5 baths

$289,900

3 beds1.5 baths1,320 sq ft

20 Greenway St, Pittsfield, MA 01201

Property at 220 N Plain Rd, Great Barrington, MA 01230, 3 beds, 2.5 baths

$499,000

3 beds2.5 baths1,922 sq ft

220 N Plain Rd, Great Barrington, MA 01230

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Homes with Pools for Sale in Berkshire County

There are currently 720 homes with pools 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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Homes with Pools for Sale in Berkshire County, MA

Homes with Pools for Sale in Berkshire County

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