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
195 Churchill St Pittsfield, MA Showings start on Friday Feb 27th. Don't overlook this updated move-in ready embankment ra...	3 beds \| 2 baths \| 1,440 sq.ft.	$369,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 7.25% Airbnb Rental Income: $1322 Traditional Rental Income: $3338 Airbnb ROI: 0.24% Traditional ROI: 7.25%
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: 0.56% Traditional cash on cash: 7.9% Airbnb Rental Income: $1322 Traditional Rental Income: $3446 Airbnb ROI: 0.56% Traditional ROI: 7.9%
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%
89 Crofut St Pittsfield, MA A Grand Federal-Style Home in the Heart of Town. Unspoiled architectural features. Set on ...	5 beds \| 5 baths \| 6,128 sq.ft.	$1,100,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 3.59% Airbnb Rental Income: $3867 Traditional Rental Income: $6880 Airbnb ROI: -0.17% Traditional ROI: 3.59%
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%
135 Allengate Ave Pittsfield, MA This classic brick Cape-style home blends comfort, convenience, and charm. Come sit in liv...	3 beds \| 2 baths \| 1,916 sq.ft.	$360,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 6.91% Airbnb Rental Income: $1322 Traditional Rental Income: $3340 Airbnb ROI: -0.27% 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.	$224,900	Airbnb cash on cash: 1% Traditional cash on cash: 11.48% Airbnb Rental Income: $1322 Traditional Rental Income: $3144 Airbnb ROI: 1% Traditional ROI: 11.48%
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.	$330,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 9.11% Airbnb Rental Income: $1906 Traditional Rental Income: $3532 Airbnb ROI: 2.23% Traditional ROI: 9.11%
582 E New Lenox Rd Pittsfield, MA Welcome to 582 E New Lenox Rd in Pittsfield. This spacious home offers 5 bedrooms, 2.5 bat...	5 beds \| 3 baths \| 2,758 sq.ft.	$477,500	Airbnb cash on cash: 4.34% Traditional cash on cash: 5.77% Airbnb Rental Income: $3867 Traditional Rental Income: $3674 Airbnb ROI: 4.34% Traditional ROI: 5.77%
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%
14 Sunrise Cir Pittsfield, MA Immaculate and beautifully updated free-standing home offering effortless one-level living...	3 beds \| 2 baths \| 2,030 sq.ft.	$649,000	Airbnb cash on cash: -1.91% Traditional cash on cash: 1.86% Airbnb Rental Income: $1322 Traditional Rental Income: $3198 Airbnb ROI: -1.91% Traditional ROI: 1.86%
119 Orlando Ave Pittsfield, MA Stunning, completely renovated single-level home--just steps from Pontoosuc Lake--nestled ...	2 beds \| 1 baths \| 1,000 sq.ft.	$289,900	Airbnb cash on cash: 0.64% Traditional cash on cash: 5.35% Airbnb Rental Income: $1220 Traditional Rental Income: $2115 Airbnb ROI: 0.64% Traditional ROI: 5.35%
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%
133 Pomeroy Ave Pittsfield, MA Step into style and comfort in this beautifully maintained move-in ready four bedroom, two...	4 beds \| 2 baths \| 2,606 sq.ft.	$424,900	Airbnb cash on cash: 1.01% Traditional cash on cash: 6.48% Airbnb Rental Income: $1906 Traditional Rental Income: $3577 Airbnb ROI: 1.01% Traditional ROI: 6.48%
50 Root Place Pittsfield, MA Adorable Berkshire Bungalow! Perfect for downsizing or just starting out. A one bedroom, o...	1 beds \| 1 baths \| 608 sq.ft.	$152,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 8.26% Airbnb Rental Income: $898 Traditional Rental Income: $1672 Airbnb ROI: 0.61% Traditional ROI: 8.26%
25 Grand Ave Pittsfield, MA Charming 2-bedroom, 1.5-bath Cape offering a move-in ready interior with an updated kitche...	2 beds \| 2 baths \| 1,337 sq.ft.	$299,900	Airbnb cash on cash: -0.18% Traditional cash on cash: 7.06% Airbnb Rental Income: $1220 Traditional Rental Income: $2872 Airbnb ROI: -0.18% Traditional ROI: 7.06%
96 Boylston St Ext Pittsfield, MA Some homes just feel right the moment you arrive. Sitting at the end of a dead-end street,...	3 beds \| 1 baths \| 1,501 sq.ft.	$299,900	Airbnb cash on cash: 1.8% Traditional cash on cash: 8.82% Airbnb Rental Income: $1322 Traditional Rental Income: $2896 Airbnb ROI: 1.8% Traditional ROI: 8.82%

Real Estate investment in Pittsfield, MA

There are 21 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 $165. In May 2026, the average monthly cash on cash return in Pittsfield is 7.00%. The average monthly rental income in Pittsfield is $3,340.

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

There are 21 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 $3,340.

Your search for investment property begins and ends here

Investment Property for Sale in Pittsfield, MA

195 Churchill St

Pittsfield, MA

3 beds | 2 baths | 1,440 sq.ft.

$369,000

Airbnb cash on cash: 0.24%

Traditional cash on cash: 7.25%

Airbnb Rental Income: $1322

Traditional Rental Income: $3338

Airbnb ROI: 0.24%

Traditional ROI: 7.25%

11 Dodge Ave

Pittsfield, MA

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

$368,000

Airbnb cash on cash: 0.56%

Traditional cash on cash: 7.9%

Airbnb Rental Income: $1322

Traditional Rental Income: $3446

Airbnb ROI: 0.56%

Traditional ROI: 7.9%

15 Cherry Hill Dr

Pittsfield, MA

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

$799,000

Airbnb cash on cash: -0.93%

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%

89 Crofut St

Pittsfield, MA

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

$1,100,000

Airbnb cash on cash: -0.17%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $3867

Traditional Rental Income: $6880

Airbnb ROI: -0.17%

Traditional ROI: 3.59%

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%

135 Allengate Ave

Pittsfield, MA

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

$360,000

Airbnb cash on cash: -0.27%

Traditional cash on cash: 6.91%

Airbnb Rental Income: $1322

Traditional Rental Income: $3340

Airbnb ROI: -0.27%