Real Estate Investment Properties for Sale in Pittsfield, MA

Looking for investment property in Pittsfield, MA with high ROI ?

Explore a variety of short-term homes & houses in Pittsfield, MA. Invest wisely with VRBO & Pittsfield, MA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Pittsfield, MA

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
11 Dodge Ave Pittsfield, MA Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 2 baths \| 1,846 sq.ft.	$368,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 7.9% Airbnb Rental Income: $1531 Traditional Rental Income: $3446 Airbnb ROI: 1.07% Traditional ROI: 7.9%
33 Alpine Trail Pittsfield, MA Cortney K Dupont [email protected] COHEN & WHITE ASSOCIATES	5 beds \| 5 baths \| 3,381 sq.ft.	$730,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 6.5% Airbnb Rental Income: $5142 Traditional Rental Income: $7174 Airbnb ROI: 1.97% Traditional ROI: 6.5%
89 Crofut St Pittsfield, MA Maureen White-Kirkby [email protected] 413-446-5634 BERKSHIRE HATHAWAY HOMESERVI...	5 beds \| 5 baths \| 6,128 sq.ft.	$1,100,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 3.59% Airbnb Rental Income: $5142 Traditional Rental Income: $6880 Airbnb ROI: 0.87% Traditional ROI: 3.59%
156 Draper Ave Pittsfield, MA The Mazzeo Duo [email protected] 413-822-0061 BERKSHIRE HATHAWAY HOMESERVICES BARNBR...	4 beds \| 1 baths \| 1,285 sq.ft.	$299,000	Airbnb cash on cash: 5.32% Traditional cash on cash: 8.5% Airbnb Rental Income: $2938 Traditional Rental Income: $3154 Airbnb ROI: 5.32% Traditional ROI: 8.5%
103 Alpine Trail Pittsfield, MA Cortney K Dupont [email protected] COHEN & WHITE ASSOCIATES	3 beds \| 3 baths \| 2,381 sq.ft.	$759,000	Airbnb cash on cash: -1.99% Traditional cash on cash: 2.2% Airbnb Rental Income: $1531 Traditional Rental Income: $4052 Airbnb ROI: -1.99% Traditional ROI: 2.2%
57 Palomino Dr Pittsfield, MA Light, bright, and beautifully updated home in one of southeast Pittsfield''s most sought-...	5 beds \| 3 baths \| 2,907 sq.ft.	$569,000	Airbnb cash on cash: 5.02% Traditional cash on cash: 5.57% Airbnb Rental Income: $5142 Traditional Rental Income: $4389 Airbnb ROI: 5.02% Traditional ROI: 5.57%
135 Allengate Ave Pittsfield, MA With spring around the corner, the beautiful big back yard will be your SWEET little get-a...	3 beds \| 2 baths \| 1,916 sq.ft.	$360,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 6.91% Airbnb Rental Income: $1531 Traditional Rental Income: $3340 Airbnb ROI: 0.24% Traditional ROI: 6.91%
15 Orlando Ave Pittsfield, MA Investor Opportunity with Strong Upside! This 1.5-story New England-style bungalow offers ...	3 beds \| 2 baths \| 1,551 sq.ft.	$229,500	Airbnb cash on cash: 1.77% Traditional cash on cash: 11.24% Airbnb Rental Income: $1531 Traditional Rental Income: $3144 Airbnb ROI: 1.77% Traditional ROI: 11.24%
5 Marco Dr Pittsfield, MA Move-in ready and freshly reimagined, this spacious home offers 4 bedrooms and 2 full bath...	4 beds \| 2 baths \| 1,741 sq.ft.	$349,000	Airbnb cash on cash: 4.68% Traditional cash on cash: 8.56% Airbnb Rental Income: $2938 Traditional Rental Income: $3532 Airbnb ROI: 4.68% Traditional ROI: 8.56%
96 Broadview Ter Pittsfield, MA 96 Broadview Ter, Pittsfield, MA 01201 \| Single Family Residential	2 beds \| 1 baths \| 876 sq.ft.	$269,900	Airbnb cash on cash: 3.17% Traditional cash on cash: 5.38% Airbnb Rental Income: $1985 Traditional Rental Income: $2026 Airbnb ROI: 3.17% Traditional ROI: 5.38%
118 Lincoln Street Pittsfield, MA Up to 3% cashback for closing costs when you buy this 4-family house with an extra lot for...	12 beds \| 4 baths \| 4,000 sq.ft.	$495,000	Airbnb cash on cash: 6.54% Traditional cash on cash: 8.71% Airbnb Rental Income: $5142 Traditional Rental Income: $5101 Airbnb ROI: 6.54% Traditional ROI: 8.71%

Real Estate investment in Pittsfield, MA

There are 11 properties for sale in the city of Pittsfield . The median list price in Pittsfield is $364,000 and the average price per square foot is $148. In January 2026, the average monthly cash on cash return in Pittsfield is 8.00%. The average monthly rental income in Pittsfield is $3,532.

Pittsfield, MA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 11 investment properties available for sale in Pittsfield.

In 2026, the best neighborhood to buy investment property is Pittsfield.

The ROI for Long-Term is higher than the Short-Term in Pittsfield with average rental income of $3,532.

Your search for investment property begins and ends here

Investment Property for Sale in Pittsfield, MA

11 Dodge Ave

Pittsfield, MA

3 beds | 2 baths | 1,846 sq.ft.

$368,000

Airbnb cash on cash: 1.07%

Traditional cash on cash: 7.9%

Airbnb Rental Income: $1531

Traditional Rental Income: $3446

Airbnb ROI: 1.07%

Traditional ROI: 7.9%

33 Alpine Trail

Pittsfield, MA

5 beds | 5 baths | 3,381 sq.ft.

$730,000

Airbnb cash on cash: 1.97%

Traditional cash on cash: 6.5%

Airbnb Rental Income: $5142

Traditional Rental Income: $7174

Airbnb ROI: 1.97%

Traditional ROI: 6.5%

89 Crofut St

Pittsfield, MA

5 beds | 5 baths | 6,128 sq.ft.

$1,100,000

Airbnb cash on cash: 0.87%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $5142

Traditional Rental Income: $6880

Airbnb ROI: 0.87%

Traditional ROI: 3.59%

156 Draper Ave

Pittsfield, MA

4 beds | 1 baths | 1,285 sq.ft.

$299,000

Airbnb cash on cash: 5.32%

Traditional cash on cash: 8.5%

Airbnb Rental Income: $2938

Traditional Rental Income: $3154

Airbnb ROI: 5.32%

Traditional ROI: 8.5%

103 Alpine Trail

Pittsfield, MA

3 beds | 3 baths | 2,381 sq.ft.

$759,000

Airbnb cash on cash: -1.99%

Traditional cash on cash: 2.2%

Airbnb Rental Income: $1531

Traditional Rental Income: $4052

Airbnb ROI: -1.99%

Traditional ROI: 2.2%

57 Palomino Dr

Pittsfield, MA

5 beds | 3 baths | 2,907 sq.ft.

$569,000

Airbnb cash on cash: 5.02%

Traditional cash on cash: 5.57%

Airbnb Rental Income: $5142

Traditional Rental Income: $4389

Airbnb ROI: 5.02%

Traditional ROI: 5.57%

135 Allengate Ave

Pittsfield, MA

3 beds | 2 baths | 1,916 sq.ft.

$360,000

Airbnb cash on cash: 0.24%

Traditional cash on cash: 6.91%

Airbnb Rental Income: $1531

Traditional Rental Income: $3340

Airbnb ROI: 0.24%

Traditional ROI: 6.91%

15 Orlando Ave

Pittsfield, MA

3 beds | 2 baths | 1,551 sq.ft.

$229,500

Airbnb cash on cash: 1.77%

Traditional cash on cash: 11.24%

Airbnb Rental Income: $1531

Traditional Rental Income: $3144

Airbnb ROI: 1.77%