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.

Condos for Sale in Pittsfield, MA

Search for Condo for Sale in Pittsfield, Massachusetts. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 7 Condo listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
15 Cherry Hill Dr Pittsfield, MA Berkshire Country Meadows single-family condo almost ready for occupancy. Seeking single l...	3 beds \| 2 baths \| 2,000 sq.ft.	$799,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 3.71% Airbnb Rental Income: $1322 Traditional Rental Income: $4367 Airbnb ROI: -0.93% Traditional ROI: 3.71%
5 Aspen Way Pittsfield, MA Great opportunity to design your 2000 sq ft free-standing condo home at Berkshire Country ...	3 beds \| 2 baths \| 2,000 sq.ft.	$819,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 3.34% Airbnb Rental Income: $1322 Traditional Rental Income: $3472 Airbnb ROI: -0.02% Traditional ROI: 3.34%
33 Alpine Trail Pittsfield, MA Beautiful townhouse located in the Pines at Bousquet with picturesque mountain views! The ...	5 beds \| 5 baths \| 3,381 sq.ft.	$699,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 6.91% Airbnb Rental Income: $3867 Traditional Rental Income: $7174 Airbnb ROI: 0.56% Traditional ROI: 6.91%
103 Alpine Trail Pittsfield, MA Thoughtfully updated end unit located at the Pines at Bousquet The first level includes a ...	3 beds \| 3 baths \| 2,381 sq.ft.	$759,000	Airbnb cash on cash: -2.3% Traditional cash on cash: 2.14% Airbnb Rental Income: $1322 Traditional Rental Income: $4052 Airbnb ROI: -2.3% Traditional ROI: 2.14%
33 Maplewood Ave unit: #103 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.	$214,900	Airbnb cash on cash: -2.94% Traditional cash on cash: 3.31% Airbnb Rental Income: $1220 Traditional Rental Income: $2101 Airbnb ROI: -2.94% Traditional ROI: 3.31%
1136 Barker Rd #27 Pittsfield, MA Charming Condominium at South Pond Farm. 2 bedrooms 2-1/2 baths, brand new kitchen. Panora...	2 beds \| 3 baths \| 1,680 sq.ft.	$595,000	Airbnb cash on cash: -2.87% Traditional cash on cash: 1% Airbnb Rental Income: $1220 Traditional Rental Income: $2974 Airbnb ROI: -2.87% Traditional ROI: 1%
33 Walden Ln Pittsfield, MA Situated on an elevated lot in desirable Walden Village, this meticulously maintained home...	3 beds \| 3 baths \| 1,806 sq.ft.	$429,900	Airbnb cash on cash: -0.6% Traditional cash on cash: 5.15% Airbnb Rental Income: $1322 Traditional Rental Income: $3227 Airbnb ROI: -0.6% Traditional ROI: 5.15%

Your search for investment property begins and ends here

Condos for Sale in Pittsfield, MA

15 Cherry Hill Dr

Pittsfield, MA

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

$799,000

Airbnb cash on cash: -0.93%

Traditional cash on cash: 3.71%

Airbnb Rental Income: $1322

Traditional Rental Income: $4367

Airbnb ROI: -0.93%

Traditional ROI: 3.71%

5 Aspen Way

Pittsfield, MA

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

$819,000

Airbnb cash on cash: -0.02%

Traditional cash on cash: 3.34%

Airbnb Rental Income: $1322

Traditional Rental Income: $3472

Airbnb ROI: -0.02%

Traditional ROI: 3.34%

33 Alpine Trail

Pittsfield, MA

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

$699,000

Airbnb cash on cash: 0.56%

Traditional cash on cash: 6.91%

Airbnb Rental Income: $3867

Traditional Rental Income: $7174

Airbnb ROI: 0.56%

Traditional ROI: 6.91%

103 Alpine Trail

Pittsfield, MA

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

$759,000

Airbnb cash on cash: -2.3%

Traditional cash on cash: 2.14%

Airbnb Rental Income: $1322

Traditional Rental Income: $4052

Airbnb ROI: -2.3%

Traditional ROI: 2.14%

33 Maplewood Ave unit: #103

Pittsfield, MA

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

$214,900

Airbnb cash on cash: -2.94%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $1220

Traditional Rental Income: $2101

Airbnb ROI: -2.94%

Traditional ROI: 3.31%

1136 Barker Rd #27

Pittsfield, MA

2 beds | 3 baths | 1,680 sq.ft.

$595,000

Airbnb cash on cash: -2.87%

Traditional cash on cash: 1%

Airbnb Rental Income: $1220

Traditional Rental Income: $2974

Airbnb ROI: -2.87%

Traditional ROI: 1%

33 Walden Ln

Pittsfield, MA

3 beds | 3 baths | 1,806 sq.ft.

$429,900

Airbnb cash on cash: -0.6%

Traditional cash on cash: 5.15%

Airbnb Rental Income: $1322

Traditional Rental Income: $3227

Airbnb ROI: -0.6%

Traditional ROI: 5.15%

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