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.

Single Family Homes for Sale in Pittsfield, MA

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

Showing 104 Single Family Residential 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
71 Weller Ave Pittsfield, MA Gabriela Dearstyne [email protected] 201-744-0154 BERKSHIRE ACCESS REALTYWelco...	3 beds \| 2 baths \| 2,024 sq.ft.	$299,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 10.02% Airbnb Rental Income: $1531 Traditional Rental Income: $3455 Airbnb ROI: 1.61% Traditional ROI: 10.02%
68 Howe Rd Pittsfield, MA One owner well cared for ranch with large finished Lower level with 1/2 bath and laundry. ...	3 beds \| 1 baths \| 2,184 sq.ft.	$385,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 4.9% Airbnb Rental Income: $1531 Traditional Rental Income: $2527 Airbnb ROI: 0.91% Traditional ROI: 4.9%
74 Norman Ave Pittsfield, MA BOM, Seller financing fell through. Charming Contemporary fabulously updated with large wr...	3 beds \| 2 baths \| 1,538 sq.ft.	$344,900	Airbnb cash on cash: 1.36% Traditional cash on cash: 7.42% Airbnb Rental Income: $1531 Traditional Rental Income: $3049 Airbnb ROI: 1.36% Traditional ROI: 7.42%
25 Calumet St Pittsfield, MA Bright and cheerful interior with family room addition and newer kitchen. Large living roo...	4 beds \| 1 baths \| 1,600 sq.ft.	$365,000	Airbnb cash on cash: 4.58% Traditional cash on cash: 6.3% Airbnb Rental Income: $2938 Traditional Rental Income: $2848 Airbnb ROI: 4.58% Traditional ROI: 6.3%
44 Strong Ave Pittsfield, MA Great Southeast location and opportunity. Wendy Rich Smith [email protected] 413-...	3 beds \| 2 baths \| 1,339 sq.ft.	$349,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 6.81% Airbnb Rental Income: $1531 Traditional Rental Income: $2942 Airbnb ROI: 1.15% Traditional ROI: 6.81%
195 Churchill St Pittsfield, MA Joanne M. Kittler [email protected] 413-344-5158 PAULA MCLEAN REALTORS INC.	3 beds \| 2 baths \| 1,440 sq.ft.	$369,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 7.4% Airbnb Rental Income: $1531 Traditional Rental Income: $3338 Airbnb ROI: 0.9% Traditional ROI: 7.4%
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: 1.07% Traditional cash on cash: 7.9% Airbnb Rental Income: $1531 Traditional Rental Income: $3446 Airbnb ROI: 1.07% 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: -0.95% Traditional cash on cash: 3.46% Airbnb Rental Income: $1531 Traditional Rental Income: $4367 Airbnb ROI: -0.95% Traditional ROI: 3.46%
40 Roland St Pittsfield, MA Cory Evangelisto [email protected] 413-358-3056 TRANSPARENT REALTY & INVESTMENTS LL...	3 beds \| 1 baths \| 1,486 sq.ft.	$289,900	Airbnb cash on cash: 1.57% Traditional cash on cash: 6.65% Airbnb Rental Income: $1531 Traditional Rental Income: $2474 Airbnb ROI: 1.57% Traditional ROI: 6.65%
1842 East St Pittsfield, MA Wendy Rich Smith RE/MAX [email protected] 413-822-1488	3 beds \| 1 baths \| 1,940 sq.ft.	$349,990	Airbnb cash on cash: 1.13% Traditional cash on cash: 5.39% Airbnb Rental Income: $1531 Traditional Rental Income: $2486 Airbnb ROI: 1.13% Traditional ROI: 5.39%
561 Pecks Rd Pittsfield, MA Douglas Collins [email protected] 413-281-6660 BERKSHIRE DREAM HOME, INC.	2 beds \| 2 baths \| 1,136 sq.ft.	$534,900	Airbnb cash on cash: 0.74% Traditional cash on cash: 1.7% Airbnb Rental Income: $1985 Traditional Rental Income: $1945 Airbnb ROI: 0.74% Traditional ROI: 1.7%
40 Baldwin Ave Pittsfield, MA Juli Kowach [email protected] 413-446-3863 BERKSHIRE DREAM HOME, INC.	4 beds \| 3 baths \| 2,870 sq.ft.	$459,900	Airbnb cash on cash: 2.7% Traditional cash on cash: 5.55% Airbnb Rental Income: $2938 Traditional Rental Income: $3488 Airbnb ROI: 2.7% Traditional ROI: 5.55%
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.	$819,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 3.34% Airbnb Rental Income: $1531 Traditional Rental Income: $3472 Airbnb ROI: 0.21% Traditional ROI: 3.34%
135 Allengate Ave Pittsfield, MA With spring around the corner, the beautiful big back yard will be your SWEET little get-a...	3 beds \| 2 baths \| 1,916 sq.ft.	$360,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 6.91% Airbnb Rental Income: $1531 Traditional Rental Income: $3340 Airbnb ROI: 0.24% Traditional ROI: 6.91%
43 Chapman Rd Pittsfield, MA 43 Chapman Rd, Pittsfield, MA 01201 \| Single Family Residential	2 beds \| 2 baths \| 1,521 sq.ft.	$409,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 4.93% Airbnb Rental Income: $1985 Traditional Rental Income: $2835 Airbnb ROI: 1.36% Traditional ROI: 4.93%
6 Vine St Pittsfield, MA 6 Vine St, Pittsfield, MA 01201 \| Single Family Residential	2 beds \| 1 baths \| 1,200 sq.ft.	$349,900	Airbnb cash on cash: 1.96% Traditional cash on cash: 4.16% Airbnb Rental Income: $1985 Traditional Rental Income: $2189 Airbnb ROI: 1.96% Traditional ROI: 4.16%
86 Winesap Rd Pittsfield, MA 86 Winesap Rd, Pittsfield, MA 01201 \| Single Family Residential	3 beds \| 2 baths \| 2,299 sq.ft.	$419,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 7.02% Airbnb Rental Income: $1531 Traditional Rental Income: $3718 Airbnb ROI: 0.31% Traditional ROI: 7.02%
127 Oak Hill Rd Pittsfield, MA 127 Oak Hill Rd, Pittsfield, MA 01201 \| Single Family Residential	3 beds \| 2 baths \| 1,824 sq.ft.	$349,900	Airbnb cash on cash: 0.81% Traditional cash on cash: 7.16% Airbnb Rental Income: $1531 Traditional Rental Income: $3176 Airbnb ROI: 0.81% Traditional ROI: 7.16%
10 Marlboro Dr Pittsfield, MA 10 Marlboro Dr, Pittsfield, MA 01201 \| Single Family Residential	3 beds \| 1 baths \| 1,572 sq.ft.	$375,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 5.08% Airbnb Rental Income: $1531 Traditional Rental Income: $2659 Airbnb ROI: 0.61% Traditional ROI: 5.08%
65 Crofut St Pittsfield, MA 65 Crofut St, Pittsfield, MA 01201 \| Single Family Residential	5 beds \| 4 baths \| 4,948 sq.ft.	$1,350,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 2.95% Airbnb Rental Income: $5142 Traditional Rental Income: $6584 Airbnb ROI: 0.97% Traditional ROI: 2.95%
100 Northumberland Rd Pittsfield, MA 100 Northumberland Rd, Pittsfield, MA 01201 \| Single Family Residential	4 beds \| 4 baths \| 3,008 sq.ft.	$549,000	Airbnb cash on cash: 2% Traditional cash on cash: 7.7% Airbnb Rental Income: $2938 Traditional Rental Income: $5180 Airbnb ROI: 2% Traditional ROI: 7.7%
41 Highland Ave Pittsfield, MA 41 Highland Ave, Pittsfield, MA 01201 \| Single Family Residential	2 beds \| 1 baths \| 1,140 sq.ft.	$220,000	Airbnb cash on cash: 4.37% Traditional cash on cash: 7.73% Airbnb Rental Income: $1985 Traditional Rental Income: $2166 Airbnb ROI: 4.37% Traditional ROI: 7.73%
1070 Holmes Rd Pittsfield, MA 1070 Holmes Rd, Pittsfield, MA 01201 \| Single Family Residential	3 beds \| 1 baths \| 1,563 sq.ft.	$329,900	Airbnb cash on cash: 0.99% Traditional cash on cash: 6.1% Airbnb Rental Income: $1531 Traditional Rental Income: $2671 Airbnb ROI: 0.99% Traditional ROI: 6.1%
551 Tamarack Rd Pittsfield, MA 551 Tamarack Rd, Pittsfield, MA 01201 \| Single Family Residential	4 beds \| 2 baths \| 2,662 sq.ft.	$699,900	Airbnb cash on cash: 1.1% Traditional cash on cash: 3.02% Airbnb Rental Income: $2938 Traditional Rental Income: $3513 Airbnb ROI: 1.1% Traditional ROI: 3.02%
215 Partridge Rd Pittsfield, MA 215 Partridge Rd, Pittsfield, MA 01201 \| Single Family Residential	3 beds \| 1 baths \| 1,664 sq.ft.	$349,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 6.95% Airbnb Rental Income: $1531 Traditional Rental Income: $3100 Airbnb ROI: 0.81% Traditional ROI: 6.95%
39 Lowden St Pittsfield, MA 39 Lowden St, Pittsfield, MA 01201 \| Single Family Residential	3 beds \| 2 baths \| 1,346 sq.ft.	$349,900	Airbnb cash on cash: 0.81% Traditional cash on cash: 6.63% Airbnb Rental Income: $1531 Traditional Rental Income: $3000 Airbnb ROI: 0.81% Traditional ROI: 6.63%
50 Grand Ave Pittsfield, MA 50 Grand Ave, Pittsfield, MA 01201 \| Single Family Residential	3 beds \| 1 baths \| 1,152 sq.ft.	$249,900	Airbnb cash on cash: 2% Traditional cash on cash: 7.86% Airbnb Rental Income: $1531 Traditional Rental Income: $2471 Airbnb ROI: 2% Traditional ROI: 7.86%
51 Foote Ave Pittsfield, MA	3 beds \| 1 baths \| 1,194 sq.ft.	$244,900	Airbnb cash on cash: 2.08% Traditional cash on cash: 8.01% Airbnb Rental Income: $1531 Traditional Rental Income: $2458 Airbnb ROI: 2.08% Traditional ROI: 8.01%
29 Murphy Pl Pittsfield, MA 29 Murphy Pl, Pittsfield, MA 01201 \| Single Family Residential	3 beds \| 1 baths \| 1,515 sq.ft.	$289,900	Airbnb cash on cash: 1.42% Traditional cash on cash: 9% Airbnb Rental Income: $1531 Traditional Rental Income: $3156 Airbnb ROI: 1.42% Traditional ROI: 9%
11 Mcallister St Pittsfield, MA 11 Mcallister St, Pittsfield, MA 01201 \| Single Family Residential	3 beds \| 2 baths \| 1,026 sq.ft.	$289,900	Airbnb cash on cash: 1.42% Traditional cash on cash: 7.51% Airbnb Rental Income: $1531 Traditional Rental Income: $2748 Airbnb ROI: 1.42% Traditional ROI: 7.51%
127 Gamwell Ave Pittsfield, MA 127 Gamwell Ave, Pittsfield, MA 01201 \| Single Family Residential	5 beds \| 2 baths \| 2,120 sq.ft.	$349,900	Airbnb cash on cash: 9.96% Traditional cash on cash: 8.16% Airbnb Rental Income: $5142 Traditional Rental Income: $3504 Airbnb ROI: 9.96% Traditional ROI: 8.16%
36 Pittsfield Ave Pittsfield, MA 36 Pittsfield Ave, Pittsfield, MA 01201 \| Single Family Residential	3 beds \| 1 baths \| 1,394 sq.ft.	$312,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 6.2% Airbnb Rental Income: $1531 Traditional Rental Income: $2565 Airbnb ROI: 1.17% Traditional ROI: 6.2%
10 Lillybrook Rd Pittsfield, MA 10 Lillybrook Rd, Pittsfield, MA 01201 \| Single Family Residential	4 beds \| 3 baths \| 2,748 sq.ft.	$689,900	Airbnb cash on cash: 1.15% Traditional cash on cash: 6.04% Airbnb Rental Income: $2938 Traditional Rental Income: $5406 Airbnb ROI: 1.15% Traditional ROI: 6.04%
121 Edward Ave Pittsfield, MA 121 Edward Ave, Pittsfield, MA 01201 \| Single Family Residential	3 beds \| 1 baths \| 1,552 sq.ft.	$289,900	Airbnb cash on cash: 1.42% Traditional cash on cash: 7.04% Airbnb Rental Income: $1531 Traditional Rental Income: $2620 Airbnb ROI: 1.42% Traditional ROI: 7.04%
144 Brombach St Pittsfield, MA 144 Brombach St, Pittsfield, MA 01201 \| Single Family Residential	6 beds \| 3 baths \| 4,034 sq.ft.	$525,900	Airbnb cash on cash: 5.92% Traditional cash on cash: 6.72% Airbnb Rental Income: $5142 Traditional Rental Income: $4488 Airbnb ROI: 5.92% Traditional ROI: 6.72%
326 Dalton Ave Pittsfield, MA 326 Dalton Ave, Pittsfield, MA 01201 \| Single Family Residential	3 beds \| 1 baths \| 1,224 sq.ft.	$255,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 7.79% Airbnb Rental Income: $1531 Traditional Rental Income: $2502 Airbnb ROI: 1.91% Traditional ROI: 7.79%
8 Northbrook Ln Pittsfield, MA 8 Northbrook Ln, Pittsfield, MA 01201 \| Single Family Residential	4 beds \| 3 baths \| 3,100 sq.ft.	$999,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 2.53% Airbnb Rental Income: $2938 Traditional Rental Income: $4510 Airbnb ROI: 0.11% Traditional ROI: 2.53%
5 Crofut St Pittsfield, MA 5 Crofut St, Pittsfield, MA 01201 \| Single Family Residential	5 beds \| 3 baths \| 3,370 sq.ft.	$889,900	Airbnb cash on cash: 2.61% Traditional cash on cash: 5.27% Airbnb Rental Income: $5142 Traditional Rental Income: $6305 Airbnb ROI: 2.61% Traditional ROI: 5.27%
5 Eastbrook Ln Pittsfield, MA 5 Eastbrook Ln, Pittsfield, MA 01201 \| Single Family Residential	4 beds \| 3 baths \| 3,196 sq.ft.	$849,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 4.49% Airbnb Rental Income: $2938 Traditional Rental Income: $5397 Airbnb ROI: 0.52% Traditional ROI: 4.49%
4 Filomena Dr Pittsfield, MA 4 Filomena Dr, Pittsfield, MA 01201 \| Single Family Residential	4 beds \| 2 baths \| 2,464 sq.ft.	$599,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 4.92% Airbnb Rental Income: $2938 Traditional Rental Income: $4089 Airbnb ROI: 1.65% Traditional ROI: 4.92%

Your search for investment property begins and ends here

Single Family Homes for Sale in Pittsfield, MA

71 Weller Ave

Pittsfield, MA

3 beds | 2 baths | 2,024 sq.ft.

$299,000

Airbnb cash on cash: 1.61%

Traditional cash on cash: 10.02%

Airbnb Rental Income: $1531

Traditional Rental Income: $3455

Airbnb ROI: 1.61%

Traditional ROI: 10.02%

68 Howe Rd

Pittsfield, MA

3 beds | 1 baths | 2,184 sq.ft.

$385,000

Airbnb cash on cash: 0.91%

Traditional cash on cash: 4.9%

Airbnb Rental Income: $1531

Traditional Rental Income: $2527

Airbnb ROI: 0.91%

Traditional ROI: 4.9%

74 Norman Ave

Pittsfield, MA

3 beds | 2 baths | 1,538 sq.ft.

$344,900

Airbnb cash on cash: 1.36%

Traditional cash on cash: 7.42%

Airbnb Rental Income: $1531

Traditional Rental Income: $3049

Airbnb ROI: 1.36%

Traditional ROI: 7.42%

25 Calumet St

Pittsfield, MA

4 beds | 1 baths | 1,600 sq.ft.

$365,000

Airbnb cash on cash: 4.58%

Traditional cash on cash: 6.3%

Airbnb Rental Income: $2938

Traditional Rental Income: $2848

Airbnb ROI: 4.58%

Traditional ROI: 6.3%

44 Strong Ave

Pittsfield, MA

3 beds | 2 baths | 1,339 sq.ft.

$349,000

Airbnb cash on cash: 1.15%

Traditional cash on cash: 6.81%

Airbnb Rental Income: $1531

Traditional Rental Income: $2942

Airbnb ROI: 1.15%

Traditional ROI: 6.81%

195 Churchill St

Pittsfield, MA

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

$369,000

Airbnb cash on cash: 0.9%

Traditional cash on cash: 7.4%

Airbnb Rental Income: $1531

Traditional Rental Income: $3338

Airbnb ROI: 0.9%

Traditional ROI: 7.4%

11 Dodge Ave

Pittsfield, MA

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

$368,000

Airbnb cash on cash: 1.07%

Traditional cash on cash: 7.9%

Airbnb Rental Income: $1531

Traditional Rental Income: $3446

Airbnb ROI: 1.07%

Traditional ROI: 7.9%

15 Cherry Hill Dr

Pittsfield, MA

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

$799,000

Airbnb cash on cash: -0.95%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $1531

Traditional Rental Income: $4367

Airbnb ROI: -0.95%