Homes with Pools for Sale in Berkshire County, MA

94 homes

Sort:

Recommended

ABOUT THIS HOME
Home with a Pool for sale in Berkshire County, MA:
LISTING PRICE REDUCED TO REFLECT NEEDED TLC. Rarely available ground-floor end unit in desirable Stratton Hills, offering privacy, abundant natural light, and spectacular Berkshire mountain views. The open living/dining area features a dramatic picture window, while the fully applianced galley kitchen includes a convenient serving window to the private covered patio. Enjoy outdoor dining, morning coffee, or evening cocktails overlooking beautifully landscaped grounds. Two spacious bedrooms, full bath, in-unit laundry, two parking spaces, and lockable basement storage add everyday convenience. Residents enjoy a swimming pool and beautifully maintained grounds. Minutes to Williams College, Th

$215,900

2 beds1 bath672 sq ft

189 Stratton Rd Unit C-4, Williamstown, MA 01267

First-floor end unit • Private parking • Additional storage

ABOUT THIS HOME
Home with a Pool for sale in Berkshire County, MA:
Enjoy effortless living in this beautifully renovated, move-in ready condo, perfectly situated between the vibrant energy of Pittsfield and the charm of Lenox center. This one-bedroom condo features brand new carpeting, generous closet space, and a modern kitchen with newer cabinetry and an updated bathroom. Natural light fills the living space, where sliding glass doors lead you to a private deck. Life at Lennox Heights is refreshingly simple. One monthly fee covers it all -- heat, hot water, cable, internet, a private in-ground pool, tennis courts, exterior maintenance, landscaping, snow removal, trash removal, master insurance, road maintenance, town sewer, and public water. Just turn th

$199,000

1 bed1 bath800 sq ft

260 Pittsfield Rd Unit A05, Lenox, MA 01240

Private deck • In-ground pool • Renovated condo

ABOUT THIS HOME
Home with a Pool for sale in Berkshire County, MA:
Situated on just over 1.6 acres in Southfield, this charming property offers access to a private tennis court, and pool through the homeowners'' association. It has been meticulously updated and is ready for immediate occupancy. The beautiful screened porch and newly constructed terraced stonework establish the home as a genuine indoor/outdoor Berkshire retreat. Enjoy views of a striking gully and stream from your farmhouse sink and natural soapstone countertops, complemented by oak flooring throughout. During the cooler months, relax by the fireplace in the living room, which has been modernized to enhance the flow between the kitchen and porch, thereby maximizing the sense of space and e

$915,000

4 beds3 baths1,875 sq ft

1289 Canaan Southfield Rd, Southfield, MA 01259

Private tennis court • Oak flooring • Screened porch

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Berkshire County, MA:
Tucked away at the end of a private cul-de-sac on 1.22 acres, this 4-bedroom, 4-bathroom contemporary home delivers sophisticated Berkshire living just minutes from downtown Great Barrington. Offering the perfect footprint for full-time remote professionals, weekend escapees, or downsizers, this property pairs a spacious layout with the effortless lifestyle of a premier community association. The heart of the home is a dramatic, light-filled great room anchored by soaring cathedral ceilings and a brick fireplace paired with charming built-ins. The main level is designed for entertainment and ease, featuring a lavish first-floor primary suite with walk-in closets and a spacious ensuite bath.

$1,250,000

4 beds3.5 baths3,047 sq ft

3 Cornwall Dr, Great Barrington, MA 01230

Brick fireplace • 1.22 acres • Cathedral ceilings

ABOUT THIS HOME
Home with a Pool for sale in Berkshire County, MA:
Rare summer home opportunity at Klondike Campground Resort in turn-key condition! Nestled away from the road with a circular driveway, this 1996 model has a cheery eat-in kitchen, well appointed bedroom, big sunny Berkshire room & sleeper sofa for guests. The pretty deck leads to a tranquil side yard w/ fire pit and wooded view. It also boasts an open floorplan plus 2 sheds! Klondike Campground Resort is a unique deeded community that features a giant clubhouse w/ lots of amenities, a large solar-heated pool w/ poolside cafe, community fire pit, updated playground, picnic area, exercise room, basketball, tennis & pickleball courts, onsite pond for kayaking or fishing, trails, a

$119,900

1 bed1 bath672 sq ft

759 North Main Rd Unit V7-12, Otis, MA 01253

Turn-key condition • Fire pit • Circular driveway

Property at 1350 Massachusetts Ave, North Adams, MA 01247, 4 beds, 1.5 baths

$499,000

4 beds1.5 baths2,410 sq ft

1350 Massachusetts Ave, North Adams, MA 01247

Property at 250 Long Pond Rd, MA 01230, 9 beds, 9 baths

$6,475,000

9 beds9 baths12,968 sq ft

250 Long Pond Rd

Elyse Harney Real Estate

Property at 880 East Unit 10 C, Lee, MA 01238, 3 beds, 2 baths

$349,000

3 beds2 baths1,152 sq ft

880 East Unit 10 C, Lee, MA 01238

Property at 6 Manitauk Hts, Stockbridge, MA 01262, 4 beds, 3.5 baths

$950,000

4 beds3.5 baths2,052 sq ft

6 Manitauk Hts, Stockbridge, MA 01262

Property at 729 Hewins St, Sheffield, MA 01257, 5 beds, 5 baths

$4,500,000

5 beds5 baths4,700 sq ft

729 Hewins St, Sheffield, MA 01257

Property at 6 Navajo Dr, North Adams, MA 01247, 2 beds, 1 bath

$79,900

2 beds1 bath780 sq ft

6 Navajo Dr, North Adams, MA 01247

Property at 275 Pine Cone Ln, Hinsdale, MA 01235, 4 beds, 3 baths

$595,275

4 beds3 baths3,600 sq ft

275 Pine Cone Ln, Hinsdale, MA 01235

Property at 80 Taconic Ave #2, Great Barrington, MA 01230, 2 beds, 2 baths

$625,000

2 beds2 baths1,308 sq ft

80 Taconic Ave #2, Great Barrington, MA 01230

Property at 295 Blair Rd, Williamstown, MA 01267, 7 beds, 4.5 baths

$1,090,000

7 beds4.5 baths5,104 sq ft

295 Blair Rd, Williamstown, MA 01267

Property at 58 Round Hill Rd, Great Barrington, MA 01230, 5 beds, 7 baths

$3,950,000

5 beds7 baths6,378 sq ft

58 Round Hill Rd, Great Barrington, MA 01230

Property at 1015 Sisson Hill Rd, New Marlboro, MA 01230, 5 beds, 4.5 baths

$3,750,000

5 beds4.5 baths3,200 sq ft

1015 Sisson Hill Rd, New Marlboro, MA 01230

Property at 293 New Marlborough-sandisfield Rd, New Marlborough, MA 01230, 5 beds, 4.5 baths

$1,725,000

5 beds4.5 baths5,127 sq ft

293 New Marlborough-sandisfield Rd, New Marlborough, MA 01230

Property at 50 East Rd, Alford, MA 01266, 5 beds, 6.5 baths

$4,975,000

5 beds6.5 baths9,400 sq ft

50 East Rd, Alford, MA 01266

Property at 77 Seekonk Cross Rd, Great Barrington, MA 01230, 5 beds, 3.5 baths

$6,850,000

5 beds3.5 baths3,474 sq ft

77 Seekonk Cross Rd, Great Barrington, MA 01230

Property at 63 Blythewood Dr, Pittsfield, MA 01201, 5 beds, 5.5 baths

$1,099,900

5 beds5.5 baths6,121 sq ft

63 Blythewood Dr, Pittsfield, MA 01201

Property at 80 Taconic Ave #12, Great Barrington, MA 01230, 3 beds, 2 baths

$795,000

3 beds2 baths1,898 sq ft

80 Taconic Ave #12, Great Barrington, MA 01230

Property at 25 Baldwin Hill Rd, Egremont, MA 01230, 3 beds, 2 baths

$2,450,000

3 beds2 baths2,716 sq ft

25 Baldwin Hill Rd, Egremont, MA 01230

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

$3,998,000

5 beds5.5 baths5,002 sq ft

764 East Hill Rd, New Marlboro, MA 01230

Property at 89 Undermountain Rd, Egremont, MA 01258, 5 beds, 5 baths

$2,400,000

5 beds5 baths6,092 sq ft

89 Undermountain Rd, Egremont, MA 01258

Property at 209 Blue Hill Rd, Great Barrington, MA 01230, 6 beds, 6 baths

$7,250,000

6 beds6 baths13,175 sq ft

209 Blue Hill Rd, Great Barrington, MA 01230

Property at 37 Corey Rd #516, Hancock, MA 01237, 1 bed, 1 bath

$135,000

1 bed1 bath500 sq ft

37 Corey Rd #516, Hancock, MA 01237

Property at 399 Under Mountain Rd, Lenox, MA 01240, 8 beds, 6.5 baths

$7,975,000

8 beds6.5 baths9,364 sq ft

399 Under Mountain Rd, Lenox, MA 01240

Property at 1 Cornwall Dr, Great Barrington, MA 01230, 3 beds, 3 baths

$749,000

3 beds3 baths2,008 sq ft

1 Cornwall Dr, Great Barrington, MA 01230

Property at 4 Fawn Ln, Pittsfield, MA 01201, 4 beds, 4 baths

$879,000

4 beds4 baths3,520 sq ft

4 Fawn Ln, Pittsfield, MA 01201

Property at 651 Hayes Hill Rd, New Marlboro, MA 01244, 6 beds, 5.5 baths

$2,875,000

6 beds5.5 baths3,416 sq ft

651 Hayes Hill Rd, New Marlboro, MA 01244

Property at 37 Corey Rd #521, Hancock, MA 01237, 1 bed, 1 bath

$139,900

1 bed1 bath500 sq ft

37 Corey Rd #521, Hancock, MA 01237

Property at 140 Beartown Mountain Rd, Monterey, MA 01245, 4 beds, 3.5 baths

$1,350,000

4 beds3.5 baths4,343 sq ft

140 Beartown Mountain Rd, Monterey, MA 01245

Property at 475 Rossiter Rd, Richmond, MA 01254, 5 beds, 4 baths

$2,995,000

5 beds4 baths2,894 sq ft

475 Rossiter Rd, Richmond, MA 01254

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

$9,500,000

7 beds7.5 baths10,429 sq ft

30 East Rd, West Stockbridge, MA 01266

Property at 148 Maple Ave #12, Great Barrington, MA 01230, 1 bed, 1 bath

$447,300

1 bed1 bath568 sq ft

148 Maple Ave #12, Great Barrington, MA 01230

Property at 84 B Undermountain Rd, Egremont, MA 01230, 5 beds, 3.5 baths

$2,495,000

5 beds3.5 baths6,254 sq ft

84 B Undermountain Rd, Egremont, MA 01230

Property at 69 Bliven Rd, Otis, MA 01253, 6 beds, 3.5 baths

$995,000

6 beds3.5 baths2,934 sq ft

69 Bliven Rd, Otis, MA 01253

Property at 37 Corey Rd #721, Hancock, MA 01237, 1 bed, 1 bath

$130,000

1 bed1 bath500 sq ft

37 Corey Rd #721, Hancock, MA 01237

Property at 415 Brewer Branch Rd, New Marlborough, MA 01244, 5 beds, 4 baths

$1,595,000

5 beds4 baths3,404 sq ft

415 Brewer Branch Rd, New Marlborough, MA 01244

Property at 18 Highcrest Rd, Lenox, MA 01240, 4 beds, 4.5 baths

$1,039,000

4 beds4.5 baths3,691 sq ft

18 Highcrest Rd, Lenox, MA 01240

Property at 303 Lakeshore, Sandisfield, MA 01255, 4 beds, 2 baths

$575,000

4 beds2 baths3,218 sq ft

303 Lakeshore, Sandisfield, MA 01255

Viewing page 2 of 3

Based on information submitted to the MLS GRID as of Wed Sep 30 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Homes with Pools for Sale in Berkshire County

There are currently 94 homes with pools for sale in Berkshire County at a median listing price of $475K. 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 62 days. This map is refreshed with the newest listings in Berkshire County every 15 minutes.

In the past month, 159 homes have been sold in Berkshire County. In addition to houses in Berkshire County, there were also 75 condos, 1 townhouse, and 79 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.

More real estate resources for Berkshire County, MA

More to explore in Berkshire County, MA

How to buy a house in Berkshire County, MA

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Massachusetts

Copyright 2026 PrimeMLS All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this website comes in part from the VOW Program of PrimeMLS. Data last updated Wed Sep 30 2026 on the search page

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

Homes with Pools for Sale in Berkshire County, MA

Homes with Pools for Sale in Berkshire County

More real estate resources for Berkshire County, MA

Nearby Counties

Cities

Nearby Counties with Homes with Pools

Nearby Cities with Homes with Pools

More to explore in Berkshire County, MA

How to buy a house in Berkshire County, MA

Popular Markets in Massachusetts