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
33 Maplewood Ave Pittsfield, MA If you are looking for easy one-level living - don't miss this opportunity! The Maplewood ...	2 beds \| 1 baths \| 1,028 sq.ft.	$196,500	Airbnb cash on cash: 4.11% Traditional cash on cash: 8.63% Airbnb Rental Income: $1985 Traditional Rental Income: $2307 Airbnb ROI: 4.11% Traditional ROI: 8.63%
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%
15 Cherry Hill Dr Pittsfield, MA Looking to have your new home in the new year? This Berkshire Country Meadows single-leve...	3 beds \| 2 baths \| 2,000 sq.ft.	$799,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 3.46% Airbnb Rental Income: $1531 Traditional Rental Income: $4367 Airbnb ROI: -0.95% Traditional ROI: 3.46%
5 Aspen Way Pittsfield, MA Great opportunity to custom design your 2000 square foot free-standing condo home at Berks...	3 beds \| 2 baths \| 2,000 sq.ft.	$799,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 3.44% Airbnb Rental Income: $1531 Traditional Rental Income: $3472 Airbnb ROI: 0.24% Traditional ROI: 3.44%
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: 3.23% Traditional cash on cash: 7.75% Airbnb Rental Income: $5142 Traditional Rental Income: $7174 Airbnb ROI: 3.23% Traditional ROI: 7.75%
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: -0.92% Traditional cash on cash: 3.27% Airbnb Rental Income: $1531 Traditional Rental Income: $4052 Airbnb ROI: -0.92% Traditional ROI: 3.27%
932 Williams St Pittsfield, MA Welcome to 932 Williams Street in southeast Pittsfield! Just a short walk from Kirvin Park...	3 beds \| 2 baths \| 1,392 sq.ft.	$339,900	Airbnb cash on cash: 0.47% Traditional cash on cash: 6.83% Airbnb Rental Income: $1531 Traditional Rental Income: $3115 Airbnb ROI: 0.47% Traditional ROI: 6.83%
26 Walden Ln Pittsfield, MA Welcome to Walden Village. This is an inviting home that combines easy one‑level li...	3 beds \| 3 baths \| 1,305 sq.ft.	$389,900	Airbnb cash on cash: -0.14% Traditional cash on cash: 6.48% Airbnb Rental Income: $1531 Traditional Rental Income: $3509 Airbnb ROI: -0.14% Traditional ROI: 6.48%
559 Onota St Pittsfield, MA Don't wait to make your appointment to see this move-in ready home! Features that make th...	3 beds \| 1 baths \| 1,248 sq.ft.	$253,900	Airbnb cash on cash: 1.44% Traditional cash on cash: 7.08% Airbnb Rental Income: $1531 Traditional Rental Income: $2440 Airbnb ROI: 1.44% Traditional ROI: 7.08%
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%
16 Garland Ave Pittsfield, MA Sally Carr [email protected] 413-441-8030 KEY REALTY	4 beds \| 2 baths \| 1,934 sq.ft.	$375,000	Airbnb cash on cash: 3.58% Traditional cash on cash: 7.63% Airbnb Rental Income: $2938 Traditional Rental Income: $3685 Airbnb ROI: 3.58% Traditional ROI: 7.63%
135 Allengate Ave Pittsfield, MA Ring in the New Year in this charming Cape with unexpected character!	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%
10 Eastbrook Ln Pittsfield, MA Timothy J Harrigan [email protected] 413-429-7042 BERKSHIRE HATHAWAY HOMESERVICES BA...	5 beds \| 5 baths \| 3,979 sq.ft.	$1,290,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 3.72% Airbnb Rental Income: $5142 Traditional Rental Income: $7502 Airbnb ROI: 0.88% Traditional ROI: 3.72%

Real Estate investment in Pittsfield, MA

There are 15 properties for sale in the city of Pittsfield . The median list price in Pittsfield is $375,000 and the average price per square foot is $163. In December 2025, the average monthly cash on cash return in Pittsfield is 7.00%. The average monthly rental income in Pittsfield is $3,509.

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

There are 15 investment properties available for sale in Pittsfield.

In 2025, 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 $3,509.

Your search for investment property begins and ends here

Investment Property for Sale in Pittsfield, MA

33 Maplewood Ave

Pittsfield, MA

2 beds | 1 baths | 1,028 sq.ft.

$196,500

Airbnb cash on cash: 4.11%

Traditional cash on cash: 8.63%

Airbnb Rental Income: $1985

Traditional Rental Income: $2307

Airbnb ROI: 4.11%

Traditional ROI: 8.63%

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%

15 Cherry Hill Dr

Pittsfield, MA

3 beds | 2 baths | 2,000 sq.ft.

$799,000

Airbnb cash on cash: -0.95%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $1531

Traditional Rental Income: $4367

Airbnb ROI: -0.95%

Traditional ROI: 3.46%

5 Aspen Way

Pittsfield, MA

3 beds | 2 baths | 2,000 sq.ft.

$799,000

Airbnb cash on cash: 0.24%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $1531

Traditional Rental Income: $3472

Airbnb ROI: 0.24%

Traditional ROI: 3.44%

33 Alpine Trail

Pittsfield, MA

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

$730,000

Airbnb cash on cash: 3.23%

Traditional cash on cash: 7.75%

Airbnb Rental Income: $5142

Traditional Rental Income: $7174

Airbnb ROI: 3.23%

Traditional ROI: 7.75%

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: -0.92%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $1531

Traditional Rental Income: $4052

Airbnb ROI: -0.92%