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 15 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: -1.22% Traditional cash on cash: 3.71% Airbnb Rental Income: $1066 Traditional Rental Income: $4367 Airbnb ROI: -1.22% 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: -0.3% Traditional cash on cash: 3.34% Airbnb Rental Income: $1066 Traditional Rental Income: $3472 Airbnb ROI: -0.3% 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: -0.45% Traditional cash on cash: 6.91% Airbnb Rental Income: $3080 Traditional Rental Income: $7174 Airbnb ROI: -0.45% 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: -2.6% Traditional cash on cash: 2.14% Airbnb Rental Income: $1066 Traditional Rental Income: $4052 Airbnb ROI: -2.6% Traditional ROI: 2.14%
33 Maplewood Ave #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: -2.97% Traditional cash on cash: 3.31% Airbnb Rental Income: $1212 Traditional Rental Income: $2101 Airbnb ROI: -2.97% Traditional ROI: 3.31%
58 Churchill Crst Pittsfield, MA 58 Churchill Crst, Pittsfield, MA 01201 \| Condo/Coop	2 beds \| 1 baths \| 1,227 sq.ft.	$255,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 6.78% Airbnb Rental Income: $1212 Traditional Rental Income: $2259 Airbnb ROI: 0.81% Traditional ROI: 6.78%
2 Amy Ct #2 Pittsfield, MA 2 Amy Ct #2, Pittsfield, MA 01201 \| Condo/Coop	4 beds \| 3 baths \| 3,561 sq.ft.	$569,900	Airbnb cash on cash: 0.08% Traditional cash on cash: 5.34% Airbnb Rental Income: $2209 Traditional Rental Income: $4453 Airbnb ROI: 0.08% Traditional ROI: 5.34%
1450 North St #107 Pittsfield, MA 1450 North St #107, Pittsfield, MA 01201 \| Condo/Coop	3 beds \| 2 baths \| 1,500 sq.ft.	$339,900	Airbnb cash on cash: -1.7% Traditional cash on cash: 6.15% Airbnb Rental Income: $1066 Traditional Rental Income: $3205 Airbnb ROI: -1.7% Traditional ROI: 6.15%
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: -2.88% Traditional cash on cash: 1% Airbnb Rental Income: $1212 Traditional Rental Income: $2974 Airbnb ROI: -2.88% Traditional ROI: 1%
51 Churchill Crst #51 Pittsfield, MA 51 Churchill Crst #51, Pittsfield, MA 01201 \| Condo/Coop	3 beds \| 2 baths \| 1,863 sq.ft.	$299,000	Airbnb cash on cash: -3.27% Traditional cash on cash: 5.79% Airbnb Rental Income: $1066 Traditional Rental Income: $3251 Airbnb ROI: -3.27% Traditional ROI: 5.79%
1 Colt Rd #1 Pittsfield, MA 1 Colt Rd #1, Pittsfield, MA 01201 \| Condo/Coop	2 beds \| 1 baths \| 902 sq.ft.	$214,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 6.69% Airbnb Rental Income: $1212 Traditional Rental Income: $2159 Airbnb ROI: 0.1% Traditional ROI: 6.69%
108 E Housatonic St #7 Pittsfield, MA 108 E Housatonic St #7, Pittsfield, MA 01201 \| Condo/Coop	1 beds \| 1 baths \| 617 sq.ft.	$149,000	Airbnb cash on cash: -1.71% Traditional cash on cash: 7.77% Airbnb Rental Income: $775 Traditional Rental Income: $1809 Airbnb ROI: -1.71% Traditional ROI: 7.77%
32 Aspen Way Pittsfield, MA 32 Aspen Way, Pittsfield, MA 01201 \| Condo/Coop	3 beds \| 2 baths \| 2,030 sq.ft.	$600,000	Airbnb cash on cash: -2.17% Traditional cash on cash: 2.79% Airbnb Rental Income: $1066 Traditional Rental Income: $3477 Airbnb ROI: -2.17% Traditional ROI: 2.79%
64 Churchill Crst Pittsfield, MA 64 Churchill Crst, Pittsfield, MA 01201 \| Condo/Coop	1 beds \| 1 baths \| 1,060 sq.ft.	$260,000	Airbnb cash on cash: -3.09% Traditional cash on cash: 3.43% Airbnb Rental Income: $775 Traditional Rental Income: $2056 Airbnb ROI: -3.09% Traditional ROI: 3.43%
106 E Housatonic St #3 Pittsfield, MA Lovely and affordable Condominium in Southeast Pittsfield. @nd floor End unit with two ver...	2 beds \| 1 baths \| 833 sq.ft.	$199,900	Airbnb cash on cash: -0.05% Traditional cash on cash: 6.93% Airbnb Rental Income: $1212 Traditional Rental Income: $2146 Airbnb ROI: -0.05% Traditional ROI: 6.93%

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: -1.22%

Traditional cash on cash: 3.71%

Airbnb Rental Income: $1066

Traditional Rental Income: $4367

Airbnb ROI: -1.22%

Traditional ROI: 3.71%

5 Aspen Way

Pittsfield, MA

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

$819,000

Airbnb cash on cash: -0.3%

Traditional cash on cash: 3.34%

Airbnb Rental Income: $1066

Traditional Rental Income: $3472

Airbnb ROI: -0.3%

Traditional ROI: 3.34%

33 Alpine Trail

Pittsfield, MA

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

$699,000

Airbnb cash on cash: -0.45%

Traditional cash on cash: 6.91%

Airbnb Rental Income: $3080

Traditional Rental Income: $7174

Airbnb ROI: -0.45%

Traditional ROI: 6.91%

103 Alpine Trail

Pittsfield, MA

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

$759,000

Airbnb cash on cash: -2.6%

Traditional cash on cash: 2.14%

Airbnb Rental Income: $1066

Traditional Rental Income: $4052

Airbnb ROI: -2.6%

Traditional ROI: 2.14%

33 Maplewood Ave #103

Pittsfield, MA

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

$214,900

Airbnb cash on cash: -2.97%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $1212

Traditional Rental Income: $2101

Airbnb ROI: -2.97%

Traditional ROI: 3.31%

58 Churchill Crst

Pittsfield, MA

2 beds | 1 baths | 1,227 sq.ft.

$255,000

Airbnb cash on cash: 0.81%

Traditional cash on cash: 6.78%

Airbnb Rental Income: $1212

Traditional Rental Income: $2259

Airbnb ROI: 0.81%

Traditional ROI: 6.78%

2 Amy Ct #2

Pittsfield, MA

4 beds | 3 baths | 3,561 sq.ft.

$569,900

Airbnb cash on cash: 0.08%

Traditional cash on cash: 5.34%

Airbnb Rental Income: $2209

Traditional Rental Income: $4453

Airbnb ROI: 0.08%

Traditional ROI: 5.34%

1450 North St #107

Pittsfield, MA

3 beds | 2 baths | 1,500 sq.ft.

$339,900

Airbnb cash on cash: -1.7%

Traditional cash on cash: 6.15%

Airbnb Rental Income: $1066

Traditional Rental Income: $3205

Airbnb ROI: -1.7%