Downtown Pittsfield, MA homes for sale & real estate

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ABOUT THIS HOME
Downtown Pittsfield, MA Homes for Sale
This unique two-family property offers buyers a variety of possibilities. The first floor features a charming studio-style layout with freshly refinished wood floors, while the second floor offers a two-bedroom apartment with a walk-up attic providing ample storage. Over the past years, this home has been used as a single-family residence and, with some minor adjustments, could easily be transformed into a four-bedroom home. It also presents an excellent opportunity for multigenerational living and would make a great investment option. Additional highlights include a composite front porch, a newer roof (2020), and an updated heating system (2021). Ideally situated close to downtown Pittsfie

$240,000

3 beds2 baths1,872 sq ft

92 W Housatonic St, Pittsfield, MA 01201

Studio-style layout • Newer roof • Two-family property

ABOUT THIS HOME
Downtown Pittsfield, MA Homes for Sale
This is a charming country cottage located right in the city! There are beautiful hardwood floors throughout this historical home and plenty of natural light. The first floor consists of the living room, dining room, kitchen, and a 3rd bedroom or office space with its own half bathroom. The second floor includes 2 good sized bedrooms and the full bathroom. Washer/Dryer located in the basement which is spacious, clean and great for storage! Most of the acreage is in the front of the house with plenty of room for gardens. Roof 2018, Furnace 2016 and chimney work/new liner 2018. Move right into this little charmer! OPEN HOUSE Sat. 9/6 1-2:30pm

$219,900

3 beds1.5 baths913 sq ft

71 Maplewood Ave, Pittsfield, MA 01201

4,356 sq ft lot • Built 1900 • Listed 10 days

ABOUT THIS HOME
Downtown Pittsfield, MA Homes for Sale
Welcome to historic Maplewood—timeless architecture, modern comfort, and a prime location come together in one of Pittsfield's most desirable residential historic buildings. The top-floor, corner unit offers hard wood floors with natural light and a spacious layout, and is a turnkey opportunity for buyers seeking convenience, character, and a maintenance-free lifestyle in the heart of the Berkshires. The kitchen is both functional and stylish—featuring granite countertops, stainless steel appliances, and a thoughtfully efficient footprint.

$184,900

2 beds1.5 baths1,150 sq ft

33 Maplewood Ave #305, Pittsfield, MA 01201

Hard wood floors • Granite countertops • Spacious layout

ABOUT THIS HOME
Downtown Pittsfield, MA Homes for Sale
An outstanding opportunity to acquire a well-maintained multi-unit property in the heart of Pittsfield's vibrant Downtown Cultural District. This property features spacious residential units, ideal for attracting & retaining long-term tenants. Recent upgrades include newer siding and high-efficiency natural gas system. The third unit, formerly a commercial storefront, offers excellent potential to be converted back to commercial use (with special permitting), adding a valuable mixed-use component to your portfolio. Generous on-site parking—a rare and highly desirable amenity in this central location. Just steps from restaurants, shops, public transportation, and major cultural a

$310,000

3 beds3 baths5,392 sq ft

50 W Housatonic St, Pittsfield, MA 01201

Residential units • Central location • On-site parking

ABOUT THIS HOME
Downtown Pittsfield, MA Homes for Sale
Spacious three-family home in the heart of Pittsfield's vibrant Downtown Cultural District! This property features a total of 3 bedrooms, offering strong rental potential and versatility. Recent capital improvements include newer roof and siding, reducing immediate maintenance costs and boosting curb appeal. Situated in a highly desirable, walkable location near restaurants, the Berkshire Carousel, galleries, theaters, shopping and public transit, this property is perfectly positioned for both appreciation and consistent cash flow. Whether you're expanding your portfolio or entering a high-demand market, this is a rare opportunity to secure a multi-family asset in one of the city's most dyn

$268,500

3 beds3 baths1,603 sq ft

79 Center St, Pittsfield, MA 01201

Newer roof • Near restaurants • Newer siding

Property at 17 - 23 Linden St, Pittsfield, MA 01201, 7 beds, 7 baths

$799,000

7 beds7 baths4,290 sq ft

17 - 23 Linden St, Pittsfield, MA 01201

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

$470,000

8 beds6 baths8,543 sq ft

153 First St, Pittsfield, MA 01201

Property at 51-53 Adam St, Pittsfield, MA 01201, 4 beds, 2 baths

$199,900

4 beds2 baths1,480 sq ft

51-53 Adam St, 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

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ABOUT THIS HOME
Downtown Pittsfield, MA Homes for Sale
A rare opportunity to purchase almost an entire block with 4 seperate RM zoned lots, including a 5 bed / 2 bath single family home. The possibilities for this space are endless, with a total of 38,060 sq ft of land and 265' of frontage on Linden St. Close to downtown, Berkshire Medical Center and all of the local attractions.

$199,000

5 beds2 baths1,703 sq ft

136 Linden St, Pittsfield, MA 01201

0.87 acre lot • Very walkable

ABOUT THIS HOME
Downtown Pittsfield, MA Homes for Sale
This cherished family home is ready for it's next chapter. First floor features a large, open kitchen with dining area, living room, bedroom or office and full bath. Second floor features two bedrooms with lots of closet space. A large family room with vaulted ceilings separates the house and the two-car garage. Nestled at the end of a quiet dead-end street, the home sits on a large 0.30-acre lot with a fenced backyard. Located less than one mile from downtown Pittsfield, this home offers both privacy and convenience. Being sold ''as-is''.

$199,900

3 beds1 bath1,501 sq ft

96 Boylston St Ext, Pittsfield, MA 01201

0.3 acre lot • Garage • Somewhat walkable

ABOUT THIS HOME
Downtown Pittsfield, MA Homes for Sale
Subject is being sold in an upcoming Xome auction. This is to be sold as occupied with all occupants in AS IS/WHERE IS condition. Neither the seller nor the listing broker can verify the existence of any lease agreement, either written or verbal, or any rental amount being paid, due or owing. Please DO NOT disturb the occupants. Access for inspections or other purposes is NOT guaranteed - contact listing broker to confirm if it is accessible. Buyers are assuming ALL responsibility for any necessary eviction action. Spacious four bedroom and two bathroom Colonial style home located on a dead end street. Exterior features a large front porch, vinyl siding, off street parking, and a one car ga

$184,900

4 beds2 baths1,664 sq ft

14 Summit Ave, Pittsfield, MA 01201

7,841 sq ft lot • Garage • Car-dependent

3D WALKTHROUGH

ABOUT THIS HOME
Downtown Pittsfield, MA Homes for Sale
Charming Historic Carriage House Condo Enjoy carefree living in this beautifully converted historic carriage house, now a cozy and tastefully renovated condo. Tucked within a peaceful community, this unique home features a private rear deck and a charming stone patio—perfect for relaxing or entertaining. Inside, modern updates blend seamlessly with original character. Just a short stroll brings you to the heart of downtown, where you'll find vibrant dining, local art, and rich cultural attractions. A rare blend of charm, comfort, and convenience!

$229,000

2 beds1 bath867 sq ft

55 Pomeroy Ave #6, Pittsfield, MA 01201

$300 HOA • Garage • Very walkable

ABOUT THIS HOME
Downtown Pittsfield, MA Homes for Sale
Recently Renovated Two-Family Flat - Lead Compliant & Move-In Ready! Discover this nicely updated two-family flat offering comfort, convenience, & modern features. Lead compliant, this property is perfect for owner-occupants or investors alike. Each 3 BR unit boasts fresh finishes & functional layouts!. The fully fenced yard is ideal for pets, play, & entertaining, & the two-car garage provides secure parking & extra storage. Located within walking distance to schools & in a convenient location with a new (2022) sewer line & ramp for easy accessibility. This property checks all the boxes! Schedule your showing today & see why this op

$282,000

6 beds2 baths2,120 sq ft

15 Atlantic Ave, Pittsfield, MA 01201

5,663 sq ft lot • 2 garage spots • Car-dependent

ABOUT THIS HOME
Downtown Pittsfield, MA Homes for Sale
Don't miss this renovated 875 sq ft ranch, offering one-level living with thoughtful updates throughout. This home features a brand-new roof, windows, kitchen, bathroom, and flooringâ€”everything has been done for you! Enjoy a bright layout with a modern kitchen, updated bath, and cozy living spaces. The breezeway adds bonus space and connects the home to a spacious yard, perfect for relaxing or entertaining. A convenient shed provides extra storage. No basement, no problemâ€”everything you need is right here, all on one floor!

$239,900

3 beds1 bath875 sq ft

29 Crystal St, Pittsfield, MA 01201

8,712 sq ft lot • Car-dependent

Property at 34 Lenox Ave, Pittsfield, MA 01201, 3 beds, 1.5 baths

$195,000

3 beds1.5 baths1,678 sq ft

34 Lenox Ave, Pittsfield, MA 01201

Property at 22 Copley Ter, Pittsfield, MA 01201, 6 beds, 3 baths

$345,000

6 beds3 baths2,892 sq ft

22 Copley Ter, Pittsfield, MA 01201

Property at 376 Fenn St, Pittsfield, MA 01201, 7 beds, 2.5 baths

$115,000

7 beds2.5 baths2,228 sq ft

376 Fenn St, Pittsfield, MA 01201

Property at 48 Copley Ter, Pittsfield, MA 01201, 3 beds, 2 baths

$239,000

3 beds2 baths1,370 sq ft

48 Copley Ter, Pittsfield, MA 01201

Property at 245 Onota St, Pittsfield, MA 01201, 2 beds, 1 bath

$189,900

2 beds1 bath1,050 sq ft

245 Onota St, Pittsfield, MA 01201

Property at 98 Lincoln St, Pittsfield, MA 01201, 7 beds, 3.5 baths

$369,000

7 beds3.5 baths3,672 sq ft

98 Lincoln St, Pittsfield, MA 01201

Property at 89 Robbins Ave, Pittsfield, MA 01201, 4 beds, 2 baths

$289,000

4 beds2 baths2,378 sq ft

89 Robbins Ave, Pittsfield, MA 01201

Property at 334 Columbus Ave, Pittsfield, MA 01201, 3 beds, 1.5 baths

$159,000

3 beds1.5 baths3,450 sq ft

334 Columbus Ave, Pittsfield, MA 01201

Property at 24 Southern Ave, Pittsfield, MA 01201, 5 beds, 2 baths

$230,000

5 beds2 baths1,768 sq ft

24 Southern Ave, Pittsfield, MA 01201

Property at 36-38 Chickering St, Pittsfield, MA 01201, 6 beds, 2.5 baths

$390,000

6 beds2.5 baths3,200 sq ft

36-38 Chickering St, Pittsfield, MA 01201

Property at 133 Pomeroy Ave, Pittsfield, MA 01201, 4 beds, 2 baths

$464,900

4 beds2 baths2,606 sq ft

133 Pomeroy Ave, Pittsfield, MA 01201

Property at 242 Wahconah St, Pittsfield, MA 01201, 6 beds, 2 baths

$175,000

6 beds2 baths2,128 sq ft

242 Wahconah St, Pittsfield, MA 01201

Property at 151 Onota St, Pittsfield, MA 01201, 6 beds, 3 baths

$344,900

6 beds3 baths3,366 sq ft

151 Onota St, Pittsfield, MA 01201

Property at 33 Circular Ave, Pittsfield, MA 01201

$39,000

— beds— baths— sq ft

33 Circular Ave, Pittsfield, MA 01201

Average home prices near Downtown Pittsfield, MA

Cities

Adams homes for sale
$245,900
Cheshire homes for sale
$149,900
Great Barrington homes for sale
$695,000
Lee homes for sale
$499,000
Lenox homes for sale
$1,085,000
Pittsfield homes for sale
$345,000
Williamstown homes for sale
$650,000
Huntington homes for sale
$282,450
North Adams homes for sale
$275,000

Neighborhoods

West Side homes for sale
$256,000
Morningside homes for sale
$179,900

Downtown Pittsfield, MA real estate trends

All Home Types trends in Downtown Pittsfield, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$204,950

-8.9% YoY | Jul 2025

1 year
3 year
5 year

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

Location

Data

Jul 2025

Growth

% YoY

Downtown Pittsfield, MA

$204,950

-8.9%

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