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
84 Williams St Pittsfield, MA Perenick Team [email protected] 413-443-7274 BERKSHIRE DREAM HOME, INC.	3 beds \| 1 baths \| 1,560 sq.ft.	$314,900	Airbnb cash on cash: -0.1% Traditional cash on cash: 6.83% Airbnb Rental Income: $1139 Traditional Rental Income: $2813 Airbnb ROI: -0.1% Traditional ROI: 6.83%
94 Tor Ct Pittsfield, MA Easy one level living, located in a quiet neighborhood, across from Onota Lake. Nicely upd...	3 beds \| 2 baths \| 1,448 sq.ft.	$539,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 4.32% Airbnb Rental Income: $1139 Traditional Rental Income: $3222 Airbnb ROI: -0.57% Traditional ROI: 4.32%
101 Alpine Trl Pittsfield, MA Beautiful end-unit property featuring soaring ceilings and serene wooded views. The home o...	3 beds \| 2 baths \| 2,381 sq.ft.	$729,000	Airbnb cash on cash: -2.2% Traditional cash on cash: 1.85% Airbnb Rental Income: $1139 Traditional Rental Income: $3517 Airbnb ROI: -2.2% Traditional ROI: 1.85%
89 Robbins Ave Pittsfield, MA	5 beds \| 2 baths \| 2,378 sq.ft.	$320,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 9.5% Airbnb Rental Income: $1139 Traditional Rental Income: $3471 Airbnb ROI: 0.49% Traditional ROI: 9.5%
4 Fawn Ln Pittsfield, MA To be built and ready in 2022!! Great location for this stand-alone condo at the end of t...	4 beds \| 4 baths \| 3,520 sq.ft.	$899,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 4.92% Airbnb Rental Income: $2870 Traditional Rental Income: $6105 Airbnb ROI: 0.26% Traditional ROI: 4.92%
490 Williams St Pittsfield, MA Tiffany Roberts [email protected] 413-822-5369 ROBERTS & ASSOC. REALTY, INC	4 beds \| 2 baths \| 2,706 sq.ft.	$678,500	Airbnb cash on cash: 1.09% Traditional cash on cash: 3.52% Airbnb Rental Income: $2870 Traditional Rental Income: $3740 Airbnb ROI: 1.09% Traditional ROI: 3.52%
36 Alpine Trl Pittsfield, MA Buddy Lewis [email protected] 781-888-0284 BERKSHIRE HATHAWAY HOMESERVICE BARNBROO...	3 beds \| 2 baths \| 2,703 sq.ft.	$648,900	Airbnb cash on cash: -1.06% Traditional cash on cash: 2.97% Airbnb Rental Income: $1139 Traditional Rental Income: $3198 Airbnb ROI: -1.06% Traditional ROI: 2.97%
68 Doreen St Pittsfield, MA Nick Geranios [email protected] 413-822-6598 BERKSHIRE DREAM HOME, INC.	3 beds \| 1 baths \| 875 sq.ft.	$284,900	Airbnb cash on cash: 0.56% Traditional cash on cash: 6.6% Airbnb Rental Income: $1139 Traditional Rental Income: $2381 Airbnb ROI: 0.56% Traditional ROI: 6.6%
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: 0.12% Traditional cash on cash: 7.9% Airbnb Rental Income: $1139 Traditional Rental Income: $3446 Airbnb ROI: 0.12% Traditional ROI: 7.9%
50 W Housatonic St Pittsfield, MA	3 beds \| 3 baths \| 5,392 sq.ft.	$298,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 11.28% Airbnb Rental Income: $1139 Traditional Rental Income: $3750 Airbnb ROI: 0.62% Traditional ROI: 11.28%
28 Calumet St Pittsfield, MA Charming Cape-style home on a quiet Pittsfield street offering 3 bedrooms and 1.5 baths. M...	3 beds \| 2 baths \| 1,582 sq.ft.	$349,900	Airbnb cash on cash: -0.33% Traditional cash on cash: 5.63% Airbnb Rental Income: $1139 Traditional Rental Income: $2718 Airbnb ROI: -0.33% Traditional ROI: 5.63%
50-52 John St Pittsfield, MA	4 beds \| 2 baths \| 2,132 sq.ft.	$264,900	Airbnb cash on cash: N/A Traditional cash on cash: 11.17% Airbnb Rental Income: $null Traditional Rental Income: $3286 Airbnb ROI: N/A Traditional ROI: 11.17%
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.	$789,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 3.77% Airbnb Rental Income: $1139 Traditional Rental Income: $4367 Airbnb ROI: -1.14% Traditional ROI: 3.77%
33 Eleanor Rd Pittsfield, MA Andrew Manns [email protected] 413-329-0972 BERKSHIRE DREAM HOME, INC.	4 beds \| 2 baths \| 2,197 sq.ft.	$464,900	Airbnb cash on cash: 2.66% Traditional cash on cash: 6.98% Airbnb Rental Income: $2870 Traditional Rental Income: $4086 Airbnb ROI: 2.66% Traditional ROI: 6.98%
246 Dalton Ave Pittsfield, MA Cory Evangelisto [email protected] 413-358-3056 TRANSPARENT REALTY & INVESTMENTS LL...	3 beds \| 1 baths \| 1,572 sq.ft.	$289,900	Airbnb cash on cash: 0.28% Traditional cash on cash: 7.59% Airbnb Rental Income: $1139 Traditional Rental Income: $2756 Airbnb ROI: 0.28% Traditional ROI: 7.59%
595 Lakeway Dr Pittsfield, MA	2 beds \| 2 baths \| 1,044 sq.ft.	$749,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 1.65% Airbnb Rental Income: $1283 Traditional Rental Income: $2561 Airbnb ROI: -0.76% Traditional ROI: 1.65%
34 Hungerford St Pittsfield, MA Michael Harrigan [email protected] 413-429-7788 BERKSHIRE HATHAWAY HOMESERVICES ...	2 beds \| 1 baths \| 1,032 sq.ft.	$289,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 5.33% Airbnb Rental Income: $1283 Traditional Rental Income: $1950 Airbnb ROI: 1.4% Traditional ROI: 5.33%
28 Hopewell Dr Pittsfield, MA Meticulously maintained 3 bedroom 1 bath ranch situated perfectly on almost a quarter of a...	3 beds \| 1 baths \| 1,180 sq.ft.	$290,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 5.81% Airbnb Rental Income: $1139 Traditional Rental Income: $2265 Airbnb ROI: 0.3% Traditional ROI: 5.81%
561 Pecks Rd Pittsfield, MA Douglas Collins [email protected] 413-281-6660 BERKSHIRE DREAM HOME, INC.	2 beds \| 2 baths \| 1,136 sq.ft.	$530,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 1.73% Airbnb Rental Income: $1283 Traditional Rental Income: $1945 Airbnb ROI: -0.42% Traditional ROI: 1.73%
7 Lincoln St Pittsfield, MA Maria Liccardi [email protected] +1 413-281-2835 BERKSHIRE DREAM HOME, INC.	2 beds \| 1 baths \| 1,506 sq.ft.	$185,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 11.17% Airbnb Rental Income: $1283 Traditional Rental Income: $2466 Airbnb ROI: 2.15% Traditional ROI: 11.17%
57 Adam St Pittsfield, MA Offering an affordable path to homeownership, this property is ideal for buyers ready to t...	4 beds \| 1 baths \| 1,480 sq.ft.	$189,000	Airbnb cash on cash: 9.41% Traditional cash on cash: 10.87% Airbnb Rental Income: $2870 Traditional Rental Income: $2466 Airbnb ROI: 9.41% Traditional ROI: 10.87%
32 Westminister St Pittsfield, MA Calling all investors and creative minds! Don't miss out on this incredible opportunity to...	6 beds \| 3 baths \| 3,510 sq.ft.	$249,900	Airbnb cash on cash: 7.02% Traditional cash on cash: 11.91% Airbnb Rental Income: $2870 Traditional Rental Income: $3358 Airbnb ROI: 7.02% Traditional ROI: 11.91%
319 Fenn St Pittsfield, MA	6 beds \| 4 baths \| 3,087 sq.ft.	$445,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 7.12% Airbnb Rental Income: $2870 Traditional Rental Income: $4373 Airbnb ROI: 1.91% Traditional ROI: 7.12%
130 Oliver Ave Pittsfield, MA Anthony W Riello [email protected] 413-770-6384 BERKSHIRE DREAM HOME, INC.	3 beds \| 2 baths \| 2,399 sq.ft.	$599,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 3.34% Airbnb Rental Income: $1139 Traditional Rental Income: $3087 Airbnb ROI: -0.82% Traditional ROI: 3.34%
77 Imperial Ave Pittsfield, MA Buy through Auction.com. This foreclosure property is a great opportunity to invest in thi...	3 beds \| 1 baths \| 1,326 sq.ft.	$289,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 7.14% Airbnb Rental Income: $1139 Traditional Rental Income: $2690 Airbnb ROI: 0.06% Traditional ROI: 7.14%
80 Preston Ave Pittsfield, MA Kim Gordnier [email protected] 413-329-3547 RE/MAX COMPASS	3 beds \| 1 baths \| 1,267 sq.ft.	$299,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 7.19% Airbnb Rental Income: $1139 Traditional Rental Income: $2732 Airbnb ROI: 0.19% Traditional ROI: 7.19%
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: -0.22% Traditional cash on cash: 3.34% Airbnb Rental Income: $1139 Traditional Rental Income: $3472 Airbnb ROI: -0.22% Traditional ROI: 3.34%
3 Clarendon St Pittsfield, MA Start the New Year in style at 3 Clarendon Street! This newly renovated 3-bedroom, 2-bathr...	3 beds \| 2 baths \| 1,092 sq.ft.	$269,900	Airbnb cash on cash: 0.92% Traditional cash on cash: 9.1% Airbnb Rental Income: $1139 Traditional Rental Income: $2841 Airbnb ROI: 0.92% Traditional ROI: 9.1%
33 Alpine Trl Pittsfield, MA Beautiful townhouse located in the Pines at Bousquet with picturesque mountain views! The ...	5 beds \| 4 baths \| 3,381 sq.ft.	$699,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 6.91% Airbnb Rental Income: $4441 Traditional Rental Income: $7174 Airbnb ROI: 1.29% Traditional ROI: 6.91%
23 Aspen Way Pittsfield, MA Built about 10 years ago, this standalone condominium is conveniently located with easy ac...	4 beds \| 3 baths \| 3,600 sq.ft.	$659,900	Airbnb cash on cash: 0.66% Traditional cash on cash: 5.05% Airbnb Rental Income: $2870 Traditional Rental Income: $4908 Airbnb ROI: 0.66% Traditional ROI: 5.05%
551 Tamarack Rd Pittsfield, MA 551 Tamarack Rd, Pittsfield, MA 01201 \| Single Family Residential	4 beds \| 2 baths \| 2,662 sq.ft.	$549,900	Airbnb cash on cash: 1.88% Traditional cash on cash: 4.43% Airbnb Rental Income: $2870 Traditional Rental Income: $3513 Airbnb ROI: 1.88% Traditional ROI: 4.43%
10 Lillybrook Rd Pittsfield, MA 10 Lillybrook Rd, Pittsfield, MA 01201 \| Single Family Residential	4 beds \| 3 baths \| 2,748 sq.ft.	$649,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 6.55% Airbnb Rental Income: $2870 Traditional Rental Income: $5406 Airbnb ROI: 1.26% Traditional ROI: 6.55%
17 Wallace Pl Pittsfield, MA 17 Wallace Pl, Pittsfield, MA 01201 \| Multi Family	6 beds \| 2 baths \| 1,928 sq.ft.	$249,900	Airbnb cash on cash: 6.72% Traditional cash on cash: 11.88% Airbnb Rental Income: $2870 Traditional Rental Income: $3419 Airbnb ROI: 6.72% Traditional ROI: 11.88%
5 Crofut St Pittsfield, MA 5 Crofut St, Pittsfield, MA 01201 \| Single Family Residential	5 beds \| 2 baths \| 3,370 sq.ft.	$799,900	Airbnb cash on cash: 2.37% Traditional cash on cash: 6.11% Airbnb Rental Income: $4441 Traditional Rental Income: $6305 Airbnb ROI: 2.37% Traditional ROI: 6.11%
168-174 Elm St Pittsfield, MA 168-174 Elm St, Pittsfield, MA 01201 \| Multi Family	3 beds \| 4 baths \| 5,640 sq.ft.	$529,900	Airbnb cash on cash: 4.68% Traditional cash on cash: 9.3% Airbnb Rental Income: $4441 Traditional Rental Income: $5801 Airbnb ROI: 4.68% Traditional ROI: 9.3%
61 Tor Court Ct Pittsfield, MA 61 Tor Court Ct, Pittsfield, MA 01201 \| Single Family Residential	3 beds \| 2 baths \| 1,728 sq.ft.	$1,349,000	Airbnb cash on cash: -1.69% Traditional cash on cash: 0.23% Airbnb Rental Income: $1139 Traditional Rental Income: $3164 Airbnb ROI: -1.69% Traditional ROI: 0.23%
411 Churchill St Pittsfield, MA 411 Churchill St, Pittsfield, MA 01201 \| Single Family Residential	4 beds \| 3 baths \| 2,634 sq.ft.	$1,101,800	Airbnb cash on cash: -0.16% Traditional cash on cash: 2% Airbnb Rental Income: $2870 Traditional Rental Income: $4423 Airbnb ROI: -0.16% Traditional ROI: 2%
3-5 Pleasant St Pittsfield, MA 3-5 Pleasant St, Pittsfield, MA 01201 \| Multi Family	6 beds \| 2 baths \| 2,214 sq.ft.	$285,000	Airbnb cash on cash: 5.64% Traditional cash on cash: 10.08% Airbnb Rental Income: $2870 Traditional Rental Income: $3395 Airbnb ROI: 5.64% Traditional ROI: 10.08%
407 Churchill St Pittsfield, MA 407 Churchill St, Pittsfield, MA 01201 \| Single Family Residential	3 beds \| 2 baths \| 2,000 sq.ft.	$814,900	Airbnb cash on cash: -1.34% Traditional cash on cash: 2.2% Airbnb Rental Income: $1139 Traditional Rental Income: $3450 Airbnb ROI: -1.34% Traditional ROI: 2.2%
403 Churchill St Pittsfield, MA 403 Churchill St, Pittsfield, MA 01201 \| Single Family Residential	3 beds \| 2 baths \| 2,000 sq.ft.	$789,900	Airbnb cash on cash: -1.32% Traditional cash on cash: 2.34% Airbnb Rental Income: $1139 Traditional Rental Income: $3450 Airbnb ROI: -1.32% Traditional ROI: 2.34%

Real Estate investment in Pittsfield, MA

There are 255 properties for sale in the city of Pittsfield . The median list price in Pittsfield is $319,809 and the average price per square foot is $145. In September 2026, the average monthly cash on cash return in Pittsfield is 7.00%. The average monthly rental income in Pittsfield is $3,089.

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

There are 255 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 $3,089.

Your search for investment property begins and ends here

Investment Property for Sale in Pittsfield, MA

84 Williams St

Pittsfield, MA

3 beds | 1 baths | 1,560 sq.ft.

$314,900

Airbnb cash on cash: -0.1%

Traditional cash on cash: 6.83%

Airbnb Rental Income: $1139

Traditional Rental Income: $2813

Airbnb ROI: -0.1%

Traditional ROI: 6.83%

94 Tor Ct

Pittsfield, MA

3 beds | 2 baths | 1,448 sq.ft.

$539,000

Airbnb cash on cash: -0.57%

Traditional cash on cash: 4.32%

Airbnb Rental Income: $1139

Traditional Rental Income: $3222

Airbnb ROI: -0.57%

Traditional ROI: 4.32%

101 Alpine Trl

Pittsfield, MA

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

$729,000

Airbnb cash on cash: -2.2%

Traditional cash on cash: 1.85%

Airbnb Rental Income: $1139

Traditional Rental Income: $3517

Airbnb ROI: -2.2%

Traditional ROI: 1.85%

89 Robbins Ave

Pittsfield, MA

5 beds | 2 baths | 2,378 sq.ft.

$320,000

Airbnb cash on cash: 0.49%

Traditional cash on cash: 9.5%

Airbnb Rental Income: $1139

Traditional Rental Income: $3471

Airbnb ROI: 0.49%

Traditional ROI: 9.5%

4 Fawn Ln

Pittsfield, MA

4 beds | 4 baths | 3,520 sq.ft.

$899,000

Airbnb cash on cash: 0.26%

Traditional cash on cash: 4.92%

Airbnb Rental Income: $2870

Traditional Rental Income: $6105

Airbnb ROI: 0.26%

Traditional ROI: 4.92%

490 Williams St

Pittsfield, MA

4 beds | 2 baths | 2,706 sq.ft.

$678,500

Airbnb cash on cash: 1.09%

Traditional cash on cash: 3.52%

Airbnb Rental Income: $2870

Traditional Rental Income: $3740

Airbnb ROI: 1.09%

Traditional ROI: 3.52%

36 Alpine Trl

Pittsfield, MA

3 beds | 2 baths | 2,703 sq.ft.

$648,900

Airbnb cash on cash: -1.06%

Traditional cash on cash: 2.97%

Airbnb Rental Income: $1139

Traditional Rental Income: $3198

Airbnb ROI: -1.06%

Traditional ROI: 2.97%

68 Doreen St

Pittsfield, MA

3 beds | 1 baths | 875 sq.ft.

$284,900

Airbnb cash on cash: 0.56%

Traditional cash on cash: 6.6%

Airbnb Rental Income: $1139

Traditional Rental Income: $2381

Airbnb ROI: 0.56%