Pittsfield, MA homes for sale & real estate

181 homes

Sort:

Recommended

18 Old Farm Ln, Pittsfield, MA 01201
18 Old Farm Ln, Pittsfield, MA 01201
18 Old Farm Ln, Pittsfield, MA 01201
ABOUT THIS HOME
Pittsfield, MA Homes for Sale
Newly Constructed Farmhouse Style Home in coveted Woodmonte Estates central to all Berkshire attractions. Over the bridge into the woods escape to a magical setting amidst a woodland preserve of 2+ acres. Build a family compound of your own with 1 extra homesites to create your dreams with incredible peace and privacy yet all city conveniences. Unique living to mingle in a community with tennis, picleball or hiking and biking out your door. Central to all Berkshire attactions: two nearby lakes, The Clark north and Tanglewood south plus Upstreet Culture art, theatre and dining. The pleasure of new elegance with one level easy living and expansive guest spaces. Surround yourself with four s

$1,195,000

5 beds2.5 baths3,087 sq ft

18 Old Farm Ln, Pittsfield, MA 01201

2.13 acre lot • 3 garage spots • Car-dependent

14-16 Allessio, Pittsfield, MA 01201
14-16 Allessio, Pittsfield, MA 01201
14-16 Allessio, Pittsfield, MA 01201
ABOUT THIS HOME
Pittsfield, MA Homes for Sale
Welcome to 11-14 Allessio in Pittsfield, MA! This two unit property has so much to offer. Each Unit has 2 Bedroom / 1 Full, 1 Half Bath, Separate Driveways and 1 Detached Garage. Both Units offer 3 season front porch just in time ready for Summer! Great INVESTMENT Opportunity for the right Buyer! Both Units are occupied with month to month tenants. Purchase as Investment Income or Owner Occupancy in one Unit while you rent out the second Unit! Location is the Key on this quiet street, making this property the perfect place for a small family. Utilities are separate and responsibility of each side. Right Side (#14) has private drive, off street parking with garage and large yard and shed. L

$327,900

4 beds3 baths1,800 sq ft

14-16 Allessio, Pittsfield, MA 01201

0.26 acre lot • 2 garage spots • Car-dependent

21 Pleasant St, Pittsfield, MA 01201
21 Pleasant St, Pittsfield, MA 01201
21 Pleasant St, Pittsfield, MA 01201
ABOUT THIS HOME
Pittsfield, MA Homes for Sale
Two-family flat with each unit featuring 2 bedrooms/ 1 bath and separate natural gas heat, hot water & electric. There is a nice fenced in yard divided for each apartment, plus good off street parking! This home is close to downtown Pittsfield and would make a great home or addition to your portfolio! * Can be sold as a package with the two-family at 36 Division St in Pittsfield.

$225,000

4 beds2 baths1,734 sq ft

21 Pleasant St, Pittsfield, MA 01201

4,356 sq ft lot • Very walkable

111 Oak Hill Rd, Pittsfield, MA 01201
111 Oak Hill Rd, Pittsfield, MA 01201
111 Oak Hill Rd, Pittsfield, MA 01201
ABOUT THIS HOME
Pittsfield, MA Homes for Sale
This may be the convenient location you are looking for. .. .. .. a quiet neighborhood lane surrounded by a lovely yard just minutes from shopping, markets, restaurants and a golf course. This charming four bedroom, 2 bath Cape has a most desirable layout for both gathering and privacy. Two main level bedrooms or an office and full bath with a living room open to dining/kitchen and direct access to decking to enjoy the spacious yard and an attached garage. Two additional bedrooms with full bath on upper level complete this most special offering!

$354,000

4 beds2 baths1,610 sq ft

111 Oak Hill Rd, Pittsfield, MA 01201

0.34 acre lot • Garage • Car-dependent

10 Elm Rd, Richmond, MA 01254
10 Elm Rd, Richmond, MA 01254
10 Elm Rd, Richmond, MA 01254
ABOUT THIS HOME
Pittsfield, MA Homes for Sale
Discover the charm of this beautifully updated Richmond Shores home, perfect for year-round living or a seasonal retreat. With a spacious deck with views of Richmond Pond, this move-in-ready gem offers modern updates inside and out. A vaulted ceiling with skylights enhances the bright and airy entry and dining area, while the fireplace in living room and wood floors create a warm, inviting atmosphere. Enjoy the convenience of updated baths, a stackable laundry, and a propane-fueled furnace for comfort in every season. Plus, take advantage of exclusive access to the private Richmond Shores homeowners' beach! Buyer agrees to purchase property subject to, and assumes the payment of the better

$419,000

3 beds2 baths1,147 sq ft

10 Elm Rd, Richmond, MA 01254

0.28 acre lot • Car-dependent

Property at 4 Filomena Dr, Pittsfield, MA 01201, 4 beds, 2.5 baths

$634,900

4 beds2.5 baths2,464 sq ft

4 Filomena Dr, Pittsfield, MA 01201

Property at 304 Dalton Division Rd, Pittsfield, MA 01201, 4 beds, 2.5 baths

$610,000

4 beds2.5 baths2,464 sq ft

304 Dalton Division Rd, Pittsfield, MA 01201

Property at 50 Bellmore Dr, Pittsfield, MA 01201, 4 beds, 2.5 baths

$525,000

4 beds2.5 baths2,477 sq ft

50 Bellmore Dr, Pittsfield, MA 01201

Property at 66 Orlando Ave, Pittsfield, MA 01201, 2 beds, 1 bath

$220,000

2 beds1 bath883 sq ft

66 Orlando Ave, Pittsfield, MA 01201

Property at 12 Alpine Trl #12, Pittsfield, MA 01201, 3 beds, 2.5 baths

$499,000

3 beds2.5 baths2,381 sq ft

12 Alpine Trl #12, Pittsfield, MA 01201

Property at 1219 North St, Pittsfield, MA 01201, 3 beds, 3 baths

$295,000

3 beds3 baths3,250 sq ft

1219 North St, Pittsfield, MA 01201

Property at 153 First St, Pittsfield, MA 01201, 8 beds, 6 baths

$485,000

8 beds6 baths8,543 sq ft

153 First St, Pittsfield, MA 01201

Property at 326 Dalton Ave, Pittsfield, MA 01201, 3 beds, 1 bath

$274,900

3 beds1 bath1,224 sq ft

326 Dalton Ave, Pittsfield, MA 01201

Property at 21 Goodrich St, Pittsfield, MA 01201, 4 beds, 4 baths

$329,900

4 beds4 baths3,139 sq ft

21 Goodrich St, Pittsfield, MA 01201

Property at 43 Chapman Rd, Pittsfield, MA 01201, 2 beds, 2 baths

$429,000

2 beds2 baths1,521 sq ft

43 Chapman Rd, Pittsfield, MA 01201

Property at 469 Pecks Rd, Pittsfield, MA 01201, 4 beds, 1.5 baths

$449,000

4 beds1.5 baths1,610 sq ft

469 Pecks Rd, Pittsfield, MA 01201

Property at 1 Pheasant Way, Pittsfield, MA 01201, 4 beds, 3.5 baths

$859,000

4 beds3.5 baths3,800 sq ft

1 Pheasant Way, Pittsfield, MA 01201

Property at 26 Crosier Ave, Pittsfield, MA 01201, 3 beds, 2 baths

$245,000

3 beds2 baths1,504 sq ft

26 Crosier Ave, Pittsfield, MA 01201

Property at 762 East St, Pittsfield, MA 01201, 3 beds, 2 baths

$239,900

3 beds2 baths1,579 sq ft

762 East St, Pittsfield, MA 01201

Property at 15 Cherry Hill Dr, Pittsfield, MA 01201, 3 beds, 2 baths

$799,000

3 beds2 baths2,000 sq ft

15 Cherry Hill Dr, Pittsfield, MA 01201

Property at 15 Cherry Hill Dr Lot 12, Pittsfield, MA 01201, 3 beds, 2 baths

$799,000

3 beds2 baths2,000 sq ft

15 Cherry Hill Dr Lot 12, Pittsfield, MA 01201

Property at 5 Aspen Way, Pittsfield, MA 01201, 3 beds, 2 baths

$799,000

3 beds2 baths2,000 sq ft

5 Aspen Way, Pittsfield, MA 01201

Property at 5 Aspen Way Lot 17, Pittsfield, MA 01201, 3 beds, 2 baths

$799,000

3 beds2 baths2,000 sq ft

5 Aspen Way Lot 17, Pittsfield, MA 01201

Property at 33 Maplewood Ave #103, Pittsfield, MA 01201, 2 beds, 1 bath

$199,900

2 beds1 bath1,028 sq ft

33 Maplewood Ave #103, Pittsfield, MA 01201

Property at 62-64 Dalton Ave, Pittsfield, MA 01201, 6 beds, 6 baths

$299,000

6 beds6 baths3,627 sq ft

62-64 Dalton Ave, Pittsfield, MA 01201

Property at 10 Lillybrook Rd, Pittsfield, MA 01201, 4 beds, 4 baths

$744,000

4 beds4 baths2,748 sq ft

10 Lillybrook Rd, Pittsfield, MA 01201

Property at Lot #140 Westbrook Ter, Pittsfield, MA 01201, 4 beds, 3.5 baths

$1,200,000

4 beds3.5 baths3,409 sq ft

Lot #140 Westbrook Ter, Pittsfield, MA 01201

Property at 16 Harold St, Pittsfield, MA 01201

$58,000

— beds— baths— sq ft

16 Harold St, Pittsfield, MA 01201

Property at 407 Churchill St, Pittsfield, MA 01201

$499,000

— beds— baths— sq ft

407 Churchill St, Pittsfield, MA 01201

Property at Iroquois St, Lanesborough, MA 01237

$69,900

— beds— baths— sq ft

Iroquois St, Lanesborough, MA 01237

Property at 33 Circular Ave, Pittsfield, MA 01201

$39,000

— beds— baths— sq ft

33 Circular Ave, Pittsfield, MA 01201

Property at Lot 140 Westbrook Ter, Pittsfield, MA 01201

$79,900

— beds— baths— sq ft

Lot 140 Westbrook Ter, Pittsfield, MA 01201

Property at 0 Hungerford St, Pittsfield, MA 01201

$50,000

— beds— baths— sq ft

0 Hungerford St, Pittsfield, MA 01201

Property at 0 Longview Ter, Pittsfield, MA 01201

$12,900

— beds— baths— sq ft

0 Longview Ter, Pittsfield, MA 01201

Property at Lot 1-4 Partridge Rd, Lanesborough, MA 01237

$134,900

— beds— baths— sq ft

Lot 1-4 Partridge Rd, Lanesborough, MA 01237

Property at 0 Old Ore Bed Rd, Lanesborough, MA 01237

$89,900

— beds— baths— sq ft

0 Old Ore Bed Rd, Lanesborough, MA 01237

Property at 205 Pecks Rd, Pittsfield, MA 01201

$49,000

— beds— baths— sq ft

205 Pecks Rd, Pittsfield, MA 01201

Property at 36 Old Farm Ln, Pittsfield, MA 01201

$30,000

— beds— baths— sq ft

36 Old Farm Ln, Pittsfield, MA 01201

Property at 0 Onota St, Pittsfield, MA 01201

$49,900

— beds— baths— sq ft

0 Onota St, Pittsfield, MA 01201

Property at 0 Faucett Ln, Pittsfield, MA 01201

$71,500

— beds— baths— sq ft

0 Faucett Ln, Pittsfield, MA 01201

Property at 0 Eastbrook Ln, Pittsfield, MA 01201

$59,900

— beds— baths— sq ft

0 Eastbrook Ln, Pittsfield, MA 01201

Viewing page 4 of 5

Average home prices near Pittsfield, MA

Cities

Adams homes for sale
$279,900
Cheshire homes for sale
$159,000
Housatonic homes for sale
$649,900
Great Barrington homes for sale
$695,000
Lee homes for sale
$524,000
Lenox homes for sale
$675,000
Williamstown homes for sale
$785,000
Chester homes for sale
$700,000
North Adams homes for sale
$258,900

Neighborhoods
Zip Codes

West Side homes for sale
$192,450
Morningside homes for sale
$204,950
Downtown Pittsfield homes for sale
$214,900

Pittsfield, MA real estate trends

All Home Types trends in Pittsfield, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$284,500

-7.6% YoY | Jun 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Jun 2025

Growth

% YoY

Pittsfield, MA

$284,500

-7.6%

See more Pittsfield, MA market insights

More to explore in Pittsfield, MA

Featured
Price
Bedroom

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

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Countries

United States

Canada

Updated January 2023: 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, TITLE FORWARD, 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

Rocket Mortgage is an affiliated business of Redfin. 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. For additional information on Rocket Mortgage or to receive lending services in the State of New York, please visit RocketMortgage.com.

Rocket Mortgage, LLC, Rocket Homes Real Estate LLC, Rocket Card, LLC, RockLoans Marketplace LLC (doing business as Rocket Loans), and Rocket Money, Inc., are separate operating subsidiaries of Rocket Limited Partnership. Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company is a separate legal entity operated and managed through its own management and governance structure. Rocket Limited Partnership is an indirect, wholly owned subsidiary of Rocket Companies, Inc. (NYSE: RKT).

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.