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 58 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
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.	$392,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 4.8% Airbnb Rental Income: $1531 Traditional Rental Income: $2527 Airbnb ROI: 0.88% Traditional ROI: 4.8%
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%
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%
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%
89 Crofut St Pittsfield, MA Maureen White-Kirkby [email protected] 413-446-5634 BERKSHIRE HATHAWAY HOMESERVI...	5 beds \| 5 baths \| 6,128 sq.ft.	$1,100,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 3.59% Airbnb Rental Income: $5142 Traditional Rental Income: $6880 Airbnb ROI: 0.87% Traditional ROI: 3.59%
156 Draper Ave Pittsfield, MA The Mazzeo Duo [email protected] 413-822-0061 BERKSHIRE HATHAWAY HOMESERVICES BARNBR...	4 beds \| 1 baths \| 1,285 sq.ft.	$299,000	Airbnb cash on cash: 5.32% Traditional cash on cash: 8.5% Airbnb Rental Income: $2938 Traditional Rental Income: $3154 Airbnb ROI: 5.32% Traditional ROI: 8.5%
932 Williams St Pittsfield, MA Welcome to 932 Williams Street in southeast Pittsfield! Just a short walk from Kirvin Park...	3 beds \| 2 baths \| 1,392 sq.ft.	$339,900	Airbnb cash on cash: 0.47% Traditional cash on cash: 6.83% Airbnb Rental Income: $1531 Traditional Rental Income: $3115 Airbnb ROI: 0.47% Traditional ROI: 6.83%
57 Palomino Dr Pittsfield, MA Light, bright, and beautifully updated home in one of southeast Pittsfield''s most sought-...	5 beds \| 3 baths \| 2,907 sq.ft.	$569,000	Airbnb cash on cash: 5.02% Traditional cash on cash: 5.57% Airbnb Rental Income: $5142 Traditional Rental Income: $4389 Airbnb ROI: 5.02% Traditional ROI: 5.57%
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%
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.	$229,500	Airbnb cash on cash: 1.77% Traditional cash on cash: 11.24% Airbnb Rental Income: $1531 Traditional Rental Income: $3144 Airbnb ROI: 1.77% Traditional ROI: 11.24%
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%
145 Bartlett Ave Pittsfield, MA 145 Bartlett Ave, Pittsfield, MA 01201 \| Single Family Residential	5 beds \| 2 baths \| 3,030 sq.ft.	$349,900	Airbnb cash on cash: 9.96% Traditional cash on cash: 10.69% Airbnb Rental Income: $5142 Traditional Rental Income: $4335 Airbnb ROI: 9.96% Traditional ROI: 10.69%
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%
21 Ensign Ave Pittsfield, MA 21 Ensign Ave, Pittsfield, MA 01201 \| Single Family Residential	3 beds \| 1 baths \| 1,443 sq.ft.	$199,900	Airbnb cash on cash: 3.03% Traditional cash on cash: 11.06% Airbnb Rental Income: $1531 Traditional Rental Income: $2612 Airbnb ROI: 3.03% Traditional ROI: 11.06%
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%
36 Beacon Ave Pittsfield, MA 36 Beacon Ave, Pittsfield, MA 01201 \| Single Family Residential	1 beds \| 1 baths \| 680 sq.ft.	$115,000	Airbnb cash on cash: 5.67% Traditional cash on cash: 11.77% Airbnb Rental Income: $1389 Traditional Rental Income: $1646 Airbnb ROI: 5.67% Traditional ROI: 11.77%
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.	$354,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 6.83% Airbnb Rental Income: $1531 Traditional Rental Income: $3100 Airbnb ROI: 0.77% Traditional ROI: 6.83%
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.	$699,900	Airbnb cash on cash: 1.1% Traditional cash on cash: 5.92% Airbnb Rental Income: $2938 Traditional Rental Income: $5406 Airbnb ROI: 1.1% Traditional ROI: 5.92%
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%
46 Lucille St Pittsfield, MA 46 Lucille St, Pittsfield, MA 01201 \| Single Family Residential	3 beds \| 2 baths \| 1,544 sq.ft.	$374,900	Airbnb cash on cash: 0.61% Traditional cash on cash: 6.49% Airbnb Rental Income: $1531 Traditional Rental Income: $3156 Airbnb ROI: 0.61% Traditional ROI: 6.49%

Your search for investment property begins and ends here

Single Family Homes for Sale in Pittsfield, MA

68 Howe Rd

Pittsfield, MA

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

$392,000

Airbnb cash on cash: 0.88%

Traditional cash on cash: 4.8%

Airbnb Rental Income: $1531

Traditional Rental Income: $2527

Airbnb ROI: 0.88%

Traditional ROI: 4.8%

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%

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%

1842 East St

Pittsfield, MA

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%

89 Crofut St

Pittsfield, MA

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

$1,100,000

Airbnb cash on cash: 0.87%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $5142

Traditional Rental Income: $6880

Airbnb ROI: 0.87%

Traditional ROI: 3.59%

156 Draper Ave

Pittsfield, MA

4 beds | 1 baths | 1,285 sq.ft.

$299,000

Airbnb cash on cash: 5.32%

Traditional cash on cash: 8.5%

Airbnb Rental Income: $2938

Traditional Rental Income: $3154

Airbnb ROI: 5.32%

Traditional ROI: 8.5%

932 Williams St

Pittsfield, MA

3 beds | 2 baths | 1,392 sq.ft.

$339,900

Airbnb cash on cash: 0.47%

Traditional cash on cash: 6.83%

Airbnb Rental Income: $1531

Traditional Rental Income: $3115

Airbnb ROI: 0.47%

Traditional ROI: 6.83%

57 Palomino Dr

Pittsfield, MA

5 beds | 3 baths | 2,907 sq.ft.

$569,000

Airbnb cash on cash: 5.02%

Traditional cash on cash: 5.57%

Airbnb Rental Income: $5142

Traditional Rental Income: $4389

Airbnb ROI: 5.02%