Homes with Pools for Sale in Pittsfield, MA

15 homes

Sort:

Recommended

ABOUT THIS HOME
Home with a Pool for sale in Pittsfield, MA:
Charming 3-bedroom, 1-bath Cape featuring hardwood floors, a cozy wood-burning fireplace, and a convenient 1st-floor bedroom and full bath with separate tub and shower. Enjoy single-level living options plus a bright 3-season room overlooking a well-landscaped yard with fruit trees and an above-ground pool with a new liner. Additional highlights include an oversized 1-bay garage, replacement windows, a newer roof, and a new sewer line.

$289,000

3 beds1 bath1,566 sq ft

20 Crane Ave, Pittsfield, MA 01201

1st-floor bedroom • Well-landscaped yard • Full bath

ABOUT THIS HOME
Home with a Pool for sale in Pittsfield, MA:
Classic Colonial Charm, Exceptional Space & a Neighborhood You'll Love! This spacious four-bedroom, 2.5-bath center hall Colonial offers nearly 2,000 sq. ft. of comfortable living with a fantastic floor plan! The inviting kitchen features granite countertops and newer Energy Star rated appliances, opening to a welcoming family room with fireplace and custom built-ins. A formal dining room and living room offer wonderful spaces for entertaining. Upstairs, the primary suite boasts a private bath and generous closet space. Enjoy outdoor living on the expansive deck with hot tub and above-ground pool! A brand-new roof, mini-split for additional heating and cooling, & a desirable nei

$445,000

4 beds2.5 baths1,944 sq ft

9 Redmond Ln, Pittsfield, MA 01201

Formal dining room • Private bath • Custom built-ins

ABOUT THIS HOME
Home with a Pool for sale in Pittsfield, MA:
Gracious colonial style home in the heart of the southeast historic neighborhood minutes to upstreet cultural art and theatre district with museums, galleries, theatres, eclectic dining, and more. This home awaits your finishing touches is search of a new homeowner with a sense of style and interior design to make this beauty the show piece it deserves to be. Abundance of living spaces on multi levels, finished attic for six bedrooms boasting three full baths and one half bath. Modern kitchen and primary bath give you the start you need. New hot water baseboard heating system and incredible front yard that is edged in custom cut marble for easy care maintence. Lower level walk out offers mo

$459,900

6 beds3.5 baths3,371 sq ft

203 Bartlett Ave, Pittsfield, MA 01201

Primary bath • Lower level walk out • Colonial style home

OPEN SAT, 10AM TO 12PM

ABOUT THIS HOME
Home with a Pool for sale in Pittsfield, MA:
Welcome home to this desirable Southeast Colonial! Offering classic character and thoughtful updates, this inviting home is move-in ready! From the charming front porch to the warmth and character of the gorgeous hardwood floors, the beautifully updated kitchen features abundant storage, granite countertops, an eye-catching island, dynamic lighting, and newer appliances, creating a wonderful space for everyday living and entertaining. French door leads to the deck overlooking the private yard and above-ground pool; perfect for morning coffee or relaxing outdoors. The first floor also offers a full bath, in-kitchen laundry, and barn doors opening to the living room/1st floor bedroom. Upstair

$309,900

3 beds2 baths1,430 sq ft

15 Congress St, Pittsfield, MA 01201

Eye-catching island • Front porch • Dynamic lighting

OPEN SUN, 12:30PM TO 2PMFLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Pittsfield, MA:
This Allendale Colonial is brimming with timeless charm, stunning original woodwork and spacious, inviting rooms. A well-appointed kitchen provides both function and style, while the generous layout offers comfortable living and entertaining spaces. Outside, enjoy a private deck and above-ground pool, plus a large detached garage offering exceptional storage, parking and workspace. Set on an attractive corner lot with sidewalks for added safety, this special home combines classic character with everyday convenience in a highly desirable location close to shopping, dining, schools and all that the Berkshires have to offer.

$298,000

3 beds1.5 baths1,363 sq ft

232 Dalton Ave, Pittsfield, MA 01201

Private deck • Original woodwork • Above-ground pool

Property at 138 Alpine Trl, Pittsfield, MA 01201, 4 beds, 4.5 baths

$975,000

4 beds4.5 baths3,381 sq ft

138 Alpine Trl, Pittsfield, MA 01201

Property at 40 8th St, Pittsfield, MA 01201, 4 beds, 2.5 baths

$529,000

4 beds2.5 baths2,268 sq ft

40 8th St, Pittsfield, MA 01201

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 26 Harvard St, Pittsfield, MA 01201, 3 beds, 1 bath

$249,000

3 beds1 bath1,322 sq ft

26 Harvard St, Pittsfield, MA 01201

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 86 Crofut St, Pittsfield, MA 01201, 5 beds, 3.5 baths

$995,000

5 beds3.5 baths3,528 sq ft

86 Crofut St, Pittsfield, MA 01201

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

$549,900

5 beds3 baths2,904 sq ft

117 Lucia Dr, Pittsfield, MA 01201

Property at 31 Brunswick St, Pittsfield, MA 01201, 4 beds, 2.5 baths

$699,000

4 beds2.5 baths2,298 sq ft

31 Brunswick St, Pittsfield, MA 01201

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

$999,900

5 beds5.5 baths5,064 sq ft

63 Blythewood Dr, Pittsfield, MA 01201

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

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

NEW 9 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Pittsfield, MA:
One story townhouse in Hancock MA, on Jiminy Peak resort property. This two bedroom, two bath is located in the back of the property on a very safe and quiet road. The property is move in ready, and has been well maintained. Property amenities include two pools, two hot tubs, an exercise room and access to the ski resort. This property makes a great home or investment opportunity. This is the perfect mountain escape.

$268,900

2 beds2 baths890 sq ft

37 Corey Rd #92, Hancock, MA 01237

Two hot tubs • Exercise room • Access to ski resort

NEW 34 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Pittsfield, MA:
Enjoy mountain living in this spacious 1,590 sq. ft. multi-level Country Village condo! Featuring 3 bedrooms, 2 full baths, and a versatile loft area, this inviting retreat offers plenty of room to relax and entertain. Recently painted with new flooring, the condo boasts a wood-burning fireplace, skylights that bring in natural light, and beautiful views to enjoy from your private deck. Additional highlights include a convenient mudroom area, a large walk-in owner's closet, and an outdoor storage closet perfect for your gear. Whether you're looking for a mountain getaway, an investment property, or a place to call home, this charming condo offers the space and comfort to enjoy the best of t

$359,900

3 beds2 baths1,589 sq ft

62 Corey Rd, Hancock, MA 01237

Private deck • Mudroom area • Skylights

ABOUT THIS HOME
Home with a Pool for sale in Pittsfield, NY:
Enjoy space, scenery, and a peaceful setting! Set on 1.78 acres with an expansive lawn and wooded surroundings, this inviting Colonial offers 4 bedrooms, 2 full bathrooms, and 1 half bathroom. Built in 2004, the home features 2,464 square feet above grade, plus an additional 500 square feet of finished space below. Large windows fill the living areas with natural light, while the kitchen offers rich wood cabinetry, stainless steel appliances, and a breakfast bar that opens to the dining area. Sliding doors lead to a spacious deck overlooking the grounds—an ideal spot for morning coffee or outdoor gatherings. An above-ground pool adds to the outdoor enjoyment, offering a refreshing ret

$499,000

4 beds2.5 baths2,464 sq ft

19 Terrace Dr, New Lebanon, NY 12125

Large windows • Wooded surroundings • Expansive lawn

Listing by The Greene Realty Group

ABOUT THIS HOME
Home with a Pool for sale in Pittsfield, MA:
One of 59 detached homes homes at Silver Maple Farm in Dalton. Just 18 minutes to Tanglewood, close to shopping, The Berkshire Medical Center and all of the cultural and outdoor activities The Berkshires have to offer. SMF is arguably the best and most sought after condo community in the area. The amenities at SMF feature a clubhouse/library/kitchen and a sports complex that include a basketball court, pickleball/tennis, heated swimming pools and two walking/snowshoeing trails. #80 is located at the end of a cul de sac, has westerly views with a Bousquet Mountain backdrop. Off the great room on the first floor there is 11x14 office/music room. The garden level is designed for a family or gu

$750,000

6 beds3 baths3,521 sq ft

80 River Birch Ln #20, Dalton, MA 01226

Sports complex • Basketball court • Pickleball tennis

ABOUT THIS HOME
Home with a Pool for sale in Pittsfield, MA:
Step into an inviting, beautifully updated 3 bedroom, 3 full bath home in one of Jiminy Peak's most desirable neighborhoods. Offering an exceptional combination of comfort, style, and location, this Mountainside property places you just moments from the slopes, Marketplace, restaurants, pool, and tennis courts; an ideal setting for year-round enjoyment and an especially terrific ski opportunity. The main level features two bedrooms and two full baths, along with a light filled open-concept living space framed by floor-to-ceiling windows. Beautiful ¾'' wood flooring, crafted by the Amish from Homer wood in Pennsylvania, adds warmth and character throughout, while a wood burning firepl

$595,000

3 beds3 baths1,968 sq ft

9102 Mountainside Dr #9102, Hancock, MA 01237

Quartz countertops • $906 HOA • 2 parking spots

ABOUT THIS HOME
Home with a Pool for sale in Pittsfield, MA:
This 2 Bedroom 3 full Bath townhouse has been tastefully renovated with granite counters, Stainless appliances and thought given to the smallest of details throughout. The multi levels give you a large open floor plan leading out to your deck where in the mornings you can enjoy the sunrise and relax in the evenings. On the lower level you have a family room, Studio or whatever fits your lifestyle, with unique closets and plenty of storage, Laundry and utility room with more storage space. This community has so much to offer, you'll have access to the Clubhouse, sauna, outdoor pool, tennis, walking trails, Community garden, storage for your Kayak and fenced dog park. Just in time to enjoy th

$350,000

2 beds3 baths1,552 sq ft

7 Rolling Hills Condominium Unit 7-1, Lenox, MA 01240

Plenty of storage • Unique closets • Stainless appliances

Property at 9123 Mountainside Dr, Hancock, MA 01237, 2 beds, 2 baths

$399,000

2 beds2 baths1,346 sq ft

9123 Mountainside Dr, Hancock, MA 01237

Property at 37 Corey Rd #12, Hancock, MA 01237, 2 beds, 1.5 baths

$268,000

2 beds1.5 baths806 sq ft

37 Corey Rd #12, Hancock, MA 01237

Property at 19 Lynne Ct, Lanesborough, MA 01237, 4 beds, 3.5 baths

$990,000

4 beds3.5 baths4,320 sq ft

19 Lynne Ct, Lanesborough, MA 01237

Property at 83 Presbyterian Hill Rd, Stephentown, NY 12168, 3 beds, 2.5 baths

$869,000

3 beds2.5 baths2,200 sq ft

83 Presbyterian Hill Rd, Stephentown, NY 12168

Listing by Howard Hanna Capital Inc

Property at 9124 Mountainside Dr, Hancock, MA 01237, 2 beds, 2 baths

$389,000

2 beds2 baths1,346 sq ft

9124 Mountainside Dr, Hancock, MA 01237

Property at 260 Pittsfield Rd Unit E6, Lenox, MA 01240, 2 beds, 1.5 baths

$315,000

2 beds1.5 baths950 sq ft

260 Pittsfield Rd Unit E6, Lenox, MA 01240

Property at 8 Rolling Hls Unit 8-12, Lenox, MA 01240, 2 beds, 3 baths

$359,900

2 beds3 baths1,552 sq ft

8 Rolling Hls Unit 8-12, Lenox, MA 01240

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 241 Cunningham Hill Rd, Canaan, NY 12029, 4 beds, 4.5 baths

$9,950,000

4 beds4.5 baths6,240 sq ft

241 Cunningham Hill Rd, Canaan, NY 12029

Listing by Corcoran Country Living

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

$724,900

4 beds2.5 baths2,240 sq ft

369 Housatonic St, Lenox, MA 01240

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 37 Corey Rd #218, Hancock, MA 01237, 1 bed, 1 bath

$159,900

1 bed1 bath500 sq ft

37 Corey Rd #218, Hancock, MA 01237

Property at 7 Rolling Hls Unit 7-8, Lenox, MA 01240, 2 beds, 3 baths

$379,000

2 beds3 baths1,730 sq ft

7 Rolling Hls Unit 7-8, Lenox, MA 01240

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

Homes with Pools for Sale in Pittsfield

There are currently 15 homes with pools for sale in Pittsfield at a median listing price of $302K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Pittsfield stay on the market for 45 days. Popular neighborhoods include West Side, Morningside, and Downtown Pittsfield. This map is refreshed with the newest listings in Pittsfield every 15 minutes.

In the past month, 39 homes have been sold in Pittsfield. In addition to houses in Pittsfield, there were also 12 condos, 2 townhouses, and 34 multi-family units for sale in Pittsfield last month. Pittsfield is a minimally walkable city in Massachusetts with a Walk Score of 40. Pittsfield is home to approximately 44,710 people. Find your dream home in Pittsfield 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 Pittsfield are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Pittsfield. Our Pittsfield real estate stats and trends will give you more information about home buying and selling trends in Pittsfield. If you're looking to sell your home in the Pittsfield area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Pittsfield 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 Pittsfield, MA

More to explore in Pittsfield, MA

How to buy a house in Pittsfield, 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

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 Pittsfield, MA

Homes with Pools for Sale in Pittsfield

More real estate resources for Pittsfield, MA

Neighborhoods

Zip Codes

Nearby Cities

Nearby Cities with Homes with Pools

More to explore in Pittsfield, MA

How to buy a house in Pittsfield, MA

Popular Markets in Massachusetts