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

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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.	$199,900	Airbnb cash on cash: 5.58% Traditional cash on cash: 8.47% Airbnb Rental Income: $2337 Traditional Rental Income: $2307 Airbnb ROI: 5.58% Traditional ROI: 8.47%
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: 2.87% Traditional cash on cash: 7.9% Airbnb Rental Income: $2279 Traditional Rental Income: $3446 Airbnb ROI: 2.87% 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: -0.11% Traditional cash on cash: 3.46% Airbnb Rental Income: $2279 Traditional Rental Income: $4367 Airbnb ROI: -0.11% 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: 1.08% Traditional cash on cash: 3.44% Airbnb Rental Income: $2279 Traditional Rental Income: $3472 Airbnb ROI: 1.08% Traditional ROI: 3.44%
111 Oak Hill Rd Pittsfield, MA Mary Jane White [email protected] 413-429-7611 COHEN & WHITE ASSOCIATES	4 beds \| 2 baths \| 1,610 sq.ft.	$354,000	Airbnb cash on cash: 4.67% Traditional cash on cash: 7.5% Airbnb Rental Income: $3252 Traditional Rental Income: $3462 Airbnb ROI: 4.67% Traditional ROI: 7.5%
127 Alpine Trail Pittsfield, MA Cortney K Dupont [email protected] COHEN & WHITE ASSOCIATES	5 beds \| 5 baths \| 3,700 sq.ft.	$939,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 6.15% Airbnb Rental Income: $4216 Traditional Rental Income: $7510 Airbnb ROI: 1.36% Traditional ROI: 6.15%
40 Commonwealth Ave Pittsfield, MA Immaculate restored antique Colonial dripping with charm offering modern conveniences. Che...	5 beds \| 3 baths \| 4,078 sq.ft.	$749,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 3.52% Airbnb Rental Income: $4216 Traditional Rental Income: $4471 Airbnb ROI: 1.88% Traditional ROI: 3.52%
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: 2.1% Traditional cash on cash: 7.75% Airbnb Rental Income: $4216 Traditional Rental Income: $7174 Airbnb ROI: 2.1% Traditional ROI: 7.75%
499 Tamarack Road Pittsfield, MA CHECK OUT THE NEW PHOTOS!!!! Located next to Bousquet, just up the road from the Pittsfiel...	3 beds \| 3 baths \| 2,351 sq.ft.	$494,700	Airbnb cash on cash: 0.84% Traditional cash on cash: 4.88% Airbnb Rental Income: $2279 Traditional Rental Income: $3578 Airbnb ROI: 0.84% Traditional ROI: 4.88%
7 Cynthia Ln Pittsfield, MA A great opportunity to own in Southview. With only 24 units, turnover is unusual in this ...	3 beds \| 3 baths \| 1,951 sq.ft.	$396,500	Airbnb cash on cash: 1.64% Traditional cash on cash: 7.16% Airbnb Rental Income: $2279 Traditional Rental Income: $3765 Airbnb ROI: 1.64% Traditional ROI: 7.16%
200 West Housatonic St Pittsfield, MA The Mazzeo Duo [email protected] 413-822-0061 BERKSHIRE HATHAWAY HOMESERVICES BARNBR...	1 beds \| 1 baths \| 940 sq.ft.	$160,000	Airbnb cash on cash: 5.08% Traditional cash on cash: 10.38% Airbnb Rental Income: $1734 Traditional Rental Income: $2067 Airbnb ROI: 5.08% Traditional ROI: 10.38%
7 Walden Ln Pittsfield, MA Don''t miss your chance to own a fully renovated home in the highly sought-after Walden Vi...	2 beds \| 3 baths \| 1,238 sq.ft.	$459,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 4.85% Airbnb Rental Income: $2337 Traditional Rental Income: $3165 Airbnb ROI: 1.58% Traditional ROI: 4.85%
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: 0.11% Traditional cash on cash: 3.59% Airbnb Rental Income: $4216 Traditional Rental Income: $6880 Airbnb ROI: 0.11% Traditional ROI: 3.59%
69 Daytona Ave Pittsfield, MA Donna Digrigoli [email protected] 413-841-5245 DIGRIGOLI REAL ESTATE	3 beds \| 2 baths \| 1,443 sq.ft.	$319,000	Airbnb cash on cash: 3.04% Traditional cash on cash: 8.9% Airbnb Rental Income: $2279 Traditional Rental Income: $3467 Airbnb ROI: 3.04% Traditional ROI: 8.9%

Real Estate investment in Pittsfield, MA

There are 14 properties for sale in the city of Pittsfield . The median list price in Pittsfield is $427,750 and the average price per square foot is $186. In September 2025, the average monthly cash on cash return in Pittsfield is 7.00%. The average monthly rental income in Pittsfield is $3,506.

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

There are 14 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 $3,506.

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.

$199,900

Airbnb cash on cash: 5.58%

Traditional cash on cash: 8.47%

Airbnb Rental Income: $2337

Traditional Rental Income: $2307

Airbnb ROI: 5.58%

Traditional ROI: 8.47%

11 Dodge Ave

Pittsfield, MA

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

$368,000

Airbnb cash on cash: 2.87%

Traditional cash on cash: 7.9%

Airbnb Rental Income: $2279

Traditional Rental Income: $3446

Airbnb ROI: 2.87%

Traditional ROI: 7.9%

15 Cherry Hill Dr

Pittsfield, MA

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

$799,000

Airbnb cash on cash: -0.11%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $2279

Traditional Rental Income: $4367

Airbnb ROI: -0.11%

Traditional ROI: 3.46%

5 Aspen Way

Pittsfield, MA

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

$799,000

Airbnb cash on cash: 1.08%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $2279

Traditional Rental Income: $3472

Airbnb ROI: 1.08%

Traditional ROI: 3.44%

111 Oak Hill Rd

Pittsfield, MA

4 beds | 2 baths | 1,610 sq.ft.

$354,000

Airbnb cash on cash: 4.67%

Traditional cash on cash: 7.5%

Airbnb Rental Income: $3252

Traditional Rental Income: $3462

Airbnb ROI: 4.67%

Traditional ROI: 7.5%

127 Alpine Trail

Pittsfield, MA

5 beds | 5 baths | 3,700 sq.ft.

$939,000

Airbnb cash on cash: 1.36%

Traditional cash on cash: 6.15%

Airbnb Rental Income: $4216

Traditional Rental Income: $7510

Airbnb ROI: 1.36%

Traditional ROI: 6.15%

40 Commonwealth Ave

Pittsfield, MA

5 beds | 3 baths | 4,078 sq.ft.

$749,000

Airbnb cash on cash: 1.88%

Traditional cash on cash: 3.52%

Airbnb Rental Income: $4216

Traditional Rental Income: $4471

Airbnb ROI: 1.88%

Traditional ROI: 3.52%

33 Alpine Trail

Pittsfield, MA

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

$730,000

Airbnb cash on cash: 2.1%

Traditional cash on cash: 7.75%

Airbnb Rental Income: $4216

Traditional Rental Income: $7174

Airbnb ROI: 2.1%