Homes with Pools for Sale in Berkshire County, MA

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ABOUT THIS HOME
Home with a Pool for sale in Berkshire County, MA:
A singular opportunity to reimagine one of Lenox's historic Berkshire estates. Set on 11.90± acres just minutes from downtown Lenox and the cultural attractions of the Berkshires, Overlee was built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan/Jacobean Revival style. The original mansion remains at the heart of the property, surrounded by broad lawns and buildings added during its later evolution into an educational campus. Much of the character of the original country house remains, including handsome woodwork, substantial fireplaces, gracious rooms, and a beautiful ballroom. Most recently used for classrooms and administrative functions, the

$2,295,000

31 beds21.5 baths38,415 sq ft

349 Old Stockbridge Rd, Lenox, MA 01240

Original mansion • Handsome woodwork • 11.90 acres

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Berkshire County, MA:
STILL HOUSE brings a new level of contemporary design to the Berkshires—quietly luxurious, exquisitely detailed, and made to be lived in. Minutes from the center of Great Barrington, this newly completed 5,148-square-foot home pairs the distinctive vision of acclaimed Brooklyn studio Me & General Design with exceptional craftsmanship and materials throughout. Four bedrooms, five-and-a-half baths, a heated saltwater pool, bespoke spa and fitness spaces, solar energy and exceptional privacy make this as much a retreat as a home. Preserved stone walls from the original structure bring history, texture and a distinctly Berkshire character to the new architecture. The main living lev

$3,695,000

4 beds5.5 baths5,148 sq ft

114 Christian Hill Rd, Great Barrington, MA 01230

Outdoor fireplace • 4.19 acre lot • 3 parking spots

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Berkshire County, MA:
Gracious, elegant, and designed for living well, this exceptional center hall Colonial offers timeless character, beautiful mountain views, and an abundance of space. The welcoming entrance is accented by exquisite English stained glass, with wood floors flowing throughout the home. Five bedrooms and 3.5 baths provide room for family and guests, while grand living and dining rooms are perfect for entertaining. A spacious family room offers a more relaxed gathering space. The primary suite features cathedral ceilings and beautiful mountain views. Outside, covered patios and decks overlook a spectacular in-ground pool, gazebo, and bathhouse--creating a private setting for summer entertaining

$995,000

5 beds3.5 baths3,528 sq ft

86 Crofut St, Pittsfield, MA 01201

Covered patios • In-ground pool • Wood floors

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

OPEN TODAY, 2:30PM TO 4PM

ABOUT THIS HOME
Home with a Pool for sale in Berkshire County, MA:
Welcome to 1350 Massachusetts Ave -- a distinctive North Adams property offering space, character, and a rare combination of indoor and outdoor amenities. With 4 bedrooms, 1.5 bathrooms, and an expansive lot, this home offers room to live, entertain, relax, and make it your own. A true highlight of the property is the two-level wrap around deck, creating an exceptional outdoor living space that connects the home's porch and garage. Whether you're hosting summer gatherings, enjoying a quiet morning coffee, or spending evenings outdoors, this unique setup provides an abundance of usable space and multiple areas to enjoy. The backyard adds even more opportunity with an inground pool, offering

$525,000

4 beds1.5 baths2,410 sq ft

1350 Massachusetts Ave, North Adams, MA 01247

New gutters • Inground pool • Roof replacement

Property at Undisclosed address, Great Barrington, MA 01230, 6 beds, 6 baths

$3,550,000

6 beds6 baths9,254 sq ft

Undisclosed address, Great Barrington, MA 01230

Property at 22 Post Rd, Lenox, MA 01240, 3 beds, 2.5 baths

$939,000

3 beds2.5 baths2,262 sq ft

22 Post Rd, Lenox, MA 01240

Property at 15 Silver St, Lee, MA 01238, 4 beds, 2 baths

$399,900

4 beds2 baths2,240 sq ft

15 Silver St, Lee, MA 01238

Property at 1303 River Rd, Clarksburg, MA 01247, 3 beds, 1.5 baths

$439,900

3 beds1.5 baths1,650 sq ft

1303 River Rd, Clarksburg, MA 01247

Property at 140 Hancock Rd, Pittsfield, MA 01201, 8 beds, 6.5 baths

$3,900,000

8 beds6.5 baths7,494 sq ft

140 Hancock Rd, Pittsfield, MA 01201

Property at 187 W Park St, Lee, MA 01238, 2 beds, 1 bath

$625,000

2 beds1 bath1,278 sq ft

187 W Park St, Lee, MA 01238

Property at 24 Brunell Ave, Lenox, MA 01240, 3 beds, 1 bath

$575,000

3 beds1 bath1,600 sq ft

24 Brunell Ave, Lenox, MA 01240

Property at 3 Iroquois Dr, North Adams, MA 01247, 2 beds, 1 bath

$94,500

2 beds1 bath1,080 sq ft

3 Iroquois Dr, North Adams, MA 01247

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 497 Holmes Rd, Pittsfield, MA 01201, 8 beds, 5.5 baths

$2,800,000

8 beds5.5 baths6,761 sq ft

497 Holmes Rd, Pittsfield, MA 01201

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 354 Notch Rd, North Adams, MA 01247, 3 beds, 2.5 baths

$629,000

3 beds2.5 baths2,504 sq ft

354 Notch Rd, North Adams, MA 01247

Property at 29 Jay Ln, Great Barrington, MA 01230, 4 beds, 2.5 baths

$895,000

4 beds2.5 baths2,328 sq ft

29 Jay Ln, Great Barrington, MA 01230

Property at 23 Aspen Way, Pittsfield, MA 01201, 4 beds, 3 baths

$659,900

4 beds3 baths3,600 sq ft

23 Aspen Way, Pittsfield, MA 01201

Property at 70 Franklin St, Dalton, MA 01226, 3 beds, 2.5 baths

$399,900

3 beds2.5 baths2,262 sq ft

70 Franklin St, Dalton, MA 01226

Property at 369 Housatonic St, Lenox, MA 01240, 4 beds, 2.5 baths

$799,900

4 beds2.5 baths2,240 sq ft

369 Housatonic St, Lenox, MA 01240

Property at 42 Churchill Crst #42, Pittsfield, MA 01201, 1 bed, 1 bath

$224,500

1 bed1 bath1,056 sq ft

42 Churchill Crst #42, Pittsfield, MA 01201

Property at 200 Old Stockbridge Rd Unit VA-6, Stockbridge, MA 01262, 3 beds, 2.5 baths

$685,000

3 beds2.5 baths1,620 sq ft

200 Old Stockbridge Rd Unit VA-6, Stockbridge, MA 01262

Property at 117 Lucia Dr, Pittsfield, MA 01201, 5 beds, 3 baths

$585,000

5 beds3 baths2,904 sq ft

117 Lucia Dr, Pittsfield, MA 01201

Property at 11 Hawthorne, Stockbridge, MA 01262, 19 beds, 23 baths

$14,500,000

19 beds23 baths19,364 sq ft

11 Hawthorne, Stockbridge, MA 01262

Property at 24 Rockland Dr, Pittsfield, MA 01201, 3 beds, 2 baths

$475,000

3 beds2 baths1,702 sq ft

24 Rockland Dr, Pittsfield, MA 01201

Property at 74 Seekonk Cross Rd, Great Barrington, MA 01230, 4 beds, 3.5 baths

$3,850,000

4 beds3.5 baths4,292 sq ft

74 Seekonk Cross Rd, Great Barrington, MA 01230

Property at 50 Harrington Rd, Otis, MA 01253, 4 beds, 2.5 baths

$888,000

4 beds2.5 baths3,434 sq ft

50 Harrington Rd, Otis, MA 01253

Property at 11 Hawthorne Rd, West Stockbridge, MA 01266, 19 beds, 23 baths

$14,500,000

19 beds23 baths19,364 sq ft

11 Hawthorne Rd, West Stockbridge, MA 01266

Property at 759 North Main Rd Unit V7-12, Otis, MA 01253, 1 bed, 1 bath

$127,900

1 bed1 bath672 sq ft

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

Property at 2650 Swamp Rd, Richmond, MA 01254, 5 beds, 7 baths

$3,495,000

5 beds7 baths6,022 sq ft

2650 Swamp Rd, Richmond, MA 01254

Property at 1289 Canaan Southfield Rd, Southfield, MA 01259, 4 beds, 3 baths

$929,000

4 beds3 baths1,875 sq ft

1289 Canaan Southfield Rd, Southfield, MA 01259

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 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 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 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 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 1015 Sisson Hill Rd, New Marlboro, MA 01230, 4 beds, 3.5 baths

$3,750,000

4 beds3.5 baths2,413 sq ft

1015 Sisson Hill Rd, New Marlboro, 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 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 880 East Unit 10 C, Lee, MA 01238, 3 beds, 2 baths

$369,000

3 beds2 baths1,152 sq ft

880 East Unit 10 C, Lee, MA 01238

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Based on information submitted to the MLS GRID as of Sat Aug 29 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 88 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 54 days. This map is refreshed with the newest listings in Berkshire County every 15 minutes.

In the past month, 170 homes have been sold in Berkshire County. In addition to houses in Berkshire County, there were also 86 condos, 1 townhouse, and 72 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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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 Sat Aug 29 2026 on the search page

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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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