Most expensive homes for sale in Pittsfield, MA

$5,499,500

8 beds • 6.5 baths • 6,986 sqft

140 Hancock Rd, Pittsfield, MA 01201

#246502, Cameron Volastro, Listing office: STONE HOUSE PROPERTIES, LLC

$10,000 Closing Credit¹

$2,250,000

5 beds • 5 baths • 5,477 sqft

1030 W St, Pittsfield, MA 01201

#246692, Tracy Crawford, Molly Gillon, Listing office: COMPASS MASSACHUSETTS , LLC GB

Save big

You could save thousands when you partner with Rocket Homes℠ and Rocket Mortgage®

Tour

$10,000 Closing Credit¹

$1,800,000

4 beds • 3 baths • 3,043 sqft

593 Lakeway Dr, Pittsfield, MA 01201

#245693, Janet Benoit, Listing office: MOCKINGBIRD REAL ESTATE

$10,000 Closing Credit¹

$1,800,000

5 beds • 3 baths • 3,043 sqft

593 Lakeway Dr, Pittsfield, MA 01201

#73387881, Janet Benoit, Listing office: Janet L. Benoit

$10,000 Closing Credit¹

$1,399,900

4 beds • 3 baths • 3,100 sqft

LOT144 Eastbrook Ln, Pittsfield, MA 01201

#246540, Corey J Bishop, Syrah Bradley, Listing office: BISHOP WEST REAL ESTATE

$10,000 Closing Credit¹

$1,399,900

4 beds • 3 baths • 3,100 sqft

8 Northbrook Ln, Pittsfield, MA 01201

#246503, Corey J Bishop, Syrah Bradley, Listing office: BISHOP WEST REAL ESTATE

$10,000 Closing Credit¹

$1,200,000

4 beds • 3.5 baths • 3,409 sqft

LOT140 Westbrook Ter, Pittsfield, MA 01201

#240874, Corey J Bishop, Syrah Bradley, Listing office: BISHOP WEST REAL ESTATE

Room to negotiate?

Median Sold Price

$295K

Avg. Sale Time

70 Days

Based on our May 2025 Market Report.

$10,000 Closing Credit¹

$1,195,000

5 beds • 2.5 baths • 3,087 sqft

18 Old Farm Ln, Pittsfield, MA 01201

#245808, Tonia L. Scalise, Listing office: WILLIAM PITT SOTHEBYS - LENOX

$10,000 Closing Credit¹

$1,100,000

6 beds • 5 baths • 5,198 sqft

68 Colt Rd, Pittsfield, MA 01201

#246537, Carrie Lobovits Wright, Listing office: WILLIAM PITT SOTHEBYS - LENOX

$10,000 Closing Credit¹

$989,000

3 beds • 3 baths • 4,024 sqft

19 Aspen Way, Pittsfield, MA 01201

#246458, Victoria A Standring, Listing office: LAMACCHIA REALTY, INC

$10,000 Closing Credit¹

$895,000

4 beds • 3.5 baths • 3,800 sqft

1 Pheasant Way, Pittsfield, MA 01201

#245515, Selina Lamb, Listing office: BIRCH PROPERTIES

$10,000 Closing Credit¹

$874,900

4 beds • 3.5 baths • 2,880 sqft

979 W St, Pittsfield, MA 01201

#245998, Tonia L. Scalise, Listing office: WILLIAM PITT SOTHEBYS - LENOX

5 days on Rocket

$10,000 Closing Credit¹

$859,000

4 beds • 3.5 baths • 3,777 sqft

1136 Barker Rd Unit 65, Pittsfield, MA 01201

#246787, Paula J. McLean, Listing office: PAULA MCLEAN REALTORS INC.

$9,488 Closing Credit¹

$799,000

3 beds • 2 baths • 2,000 sqft

15 Cherry Hill Dr, Pittsfield, MA 01201

#245353, Pamela Roberts, Listing office: ROBERTS & ASSOC. REALTY, INC

$9,488 Closing Credit¹

$799,000

3 beds • 2 baths • 2,000 sqft

5 Aspen Way Lot 17, Pittsfield, MA 01201

#245339, Pamela Roberts, Listing office: ROBERTS & ASSOC. REALTY, INC

$9,441 Closing Credit¹

$795,000

5 beds • 2.5 baths • 4,078 sqft

40 Commonwealth Ave, Pittsfield, MA 01201

#246168, Maureen White-Kirkby, Listing office: BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

$9,084 Closing Credit¹

$765,000

5 beds • 4.5 baths • 3,381 sqft

33 Alpine Trl, Pittsfield, MA 01201

#246465, Cortney K Dupont, Brandon White, Listing office: COHEN & WHITE ASSOCIATES

$9,013 Closing Credit¹

$759,000

4 beds • 4 baths • 2,748 sqft

10 Lillybrook Rd, Pittsfield, MA 01201

#244543, Paul R Clark, Listing office: CLARK REALTY GROUP LLC

$8,894 Closing Credit¹

$749,000

4 beds • 3.5 baths • 3,491 sqft

26 Filomena Dr, Pittsfield, MA 01201

#246727, Barbara K. Greenfeld, Broker, Marie E. Bourassa, Listing office: SIGNATURE ASSOCIATES

$8,218 Closing Credit¹

$692,000

4 beds • 3.5 baths • 3,296 sqft

14 Alpine Trl # 14, Pittsfield, MA 01201

#246233, Elle Villetto, Listing office: WILLIAM PITT SOTHEBYS - LENOX, WILLIAM PITT SOTHEBYS - GT BARRINGTON

$8,016 Closing Credit¹

$675,000

4 beds • 4.5 baths • 3,081 sqft

24 Alpine Trl Unit 24, Pittsfield, MA 01201

#246678, Tanya Shepardson, Listing office: LAMACCHIA REALTY, INC

$7,539 Closing Credit¹

$634,900

4 beds • 2.5 baths • 2,464 sqft

4 Filomena Dr, Pittsfield, MA 01201

#245727, Joseph Jennings, Listing office: SIGNATURE ASSOCIATES

$7,480 Closing Credit¹

$629,900

4 beds • 3.5 baths • 3,561 sqft

2 Amy Ct Unit 2, Pittsfield, MA 01201

#245837, Cory Evangelisto, Listing office: NOCHER REALTY

$7,244 Closing Credit¹

$610,000

4 beds • 2.5 baths • 2,464 sqft

304 Dalton Division Rd, Pittsfield, MA 01201

#73341518, Patrick Cathro, Listing office: Coldwell Banker Community REALTORS®

Tour

$7,244 Closing Credit¹

$610,000

4 beds • 2.5 baths • 2,464 sqft

304 Dalton Division Rd, Pittsfield, MA 01201

#245689, Patrick Cathro, Listing office: NON-MEMBER / RECIPROCAL

$7,243 Closing Credit¹

$609,900

5 beds • 4.5 baths • 2,994 sqft

25 Alpine Trl, Pittsfield, MA 01201

#246557, Jesse Dimitropolis, Listing office: BISHOP WEST REAL ESTATE

$7,066 Closing Credit¹

$595,000

2 beds • 3 baths • 1,814 sqft

35 Chapman Rd, Pittsfield, MA 01201

#245858, Wayne Ditore, Listing office: BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

$6,876 Closing Credit¹

$579,000

5 beds • 2.5 baths • 2,994 sqft

100 Holmes Rd, Pittsfield, MA 01201

#246239, Victoria A Standring, Listing office: LAMACCHIA REALTY, INC

$6,828 Closing Credit¹

$575,000

3 beds • 2.5 baths • 2,381 sqft

12 Alpine Trl Unit 12, Pittsfield, MA 01201

#245565, Marc Bellora, Listing office: LAMACCHIA REALTY, INC

Tour

$6,720 Closing Credit¹

$565,900

8 beds • 3 baths • 4,034 sqft

144 Brombach St, Pittsfield, MA 01201

#246477, Darcy Reid, Listing office: MOCKINGBIRD REAL ESTATE

$6,720 Closing Credit¹

$565,900

8 beds • 3 baths • 4,034 sqft

144 Bromback, Pittsfield, MA 01201

#73388591, Janet Benoit, Listing office: Janet L. Benoit

6 minutes on Rocket

$6,411 Closing Credit¹

$539,900

3 beds • 2.5 baths • 2,093 sqft

144 Kittredge Rd, Pittsfield, MA 01201

#73395831, Douglas Collins, Listing office: Lamacchia Realty, Inc.

$6,401 Closing Credit¹

$539,000

3 beds • 2.5 baths • 2,145 sqft

121 Wendell Ave, Pittsfield, MA 01201

#246294, Victoria A Standring, Listing office: LAMACCHIA REALTY, INC

$6,234 Closing Credit¹

$525,000

3 beds • 3 baths • 3,151 sqft

499 Tamarack Rd, Pittsfield, MA 01201

#20251868, Allen Halstead, GRI, Listing office: Berkshire Hathaway HomeService

$6,234 Closing Credit¹

$525,000

4 beds • 2.5 baths • 2,477 sqft

50 Bellmore Dr, Pittsfield, MA 01201

#245703, Maureen White-Kirkby, Listing office: BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

$6,234 Closing Credit¹

$525,000

4 beds • 2.5 baths • 2,102 sqft

92 Leroi Dr, Pittsfield, MA 01201

#246435, Andrew Manns, Listing office: LAMACCHIA REALTY, INC

$5,699 Closing Credit¹

$479,900

5 beds • 3 baths • 1,824 sqft

178 Harryel St, Pittsfield, MA 01201

#246047, Anthony W Riello, Listing office: LAMACCHIA REALTY, INC

$5,647 Closing Credit¹

$475,500

4 beds • 2.5 baths • 2,560 sqft

149 Kittredge Rd, Pittsfield, MA 01201

#246185, Tanya Shepardson, Listing office: LAMACCHIA REALTY, INC

$5,639 Closing Credit¹

$474,900

3 beds • 2.5 baths • 1,868 sqft

2 Faucett Ln, Pittsfield, MA 01201

#246074, Brenda Anne Durant, Listing office: KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

5 days on Rocket

$5,486 Closing Credit¹

$462,000

3 beds • 3.5 baths • 1,943 sqft

50 Walden Ln, Pittsfield, MA 01201

#246797, Anne B. Meczywor, Listing office: ROBERTS & ASSOC. REALTY, INC

Pittsfield, MA Real Estate Market Overview

There are 110 most expensive homes for sale in Pittsfield, MA. The following market insights reflect all property types in the Pittsfield, MA real estate market. In May 2025 in Pittsfield, MA there were 14.2% more homes for sale than in April 2025. In May 2025, listings were on the market for 70 days. During the same period, the median list price in this real estate market was $295,021. Pittsfield, MA housing market in May 2025 saw over 18 listings sold above listed price, more than 10 sold at listed price and over 23 sold below.

From Rocket Homes Real Estate and based on county public records data

Schools near Pittsfield, MA

Elementary Schools

Robert T. Capeless Elementary School
86 Brooks Ave
Public District PK-5
Egremont
84 Egremont Ave
Public District KG-5
Stearns
75 Lebanon Ave
Public District KG-5

Middle Schools

Theodore Herberg Middle School
501 Pomeroy Ave
Public District 6-8
John T Reid Middle School
950 North St
Public District 6-8

High Schools

Taconic High School
96 Valentine Rd
Public District 9-12
Pittsfield High School
300 East St
Public District 9-12

Data provided by Great Schools

Most expensive homes for sale in Pittsfield, MA

Pittsfield, MA Real Estate Market Overview

Schools near Pittsfield, MA

Housing market reports in Berkshire County

Top real estate cities in Massachusetts