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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
71 Weller AvePittsfield, MAGabriela 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%
|
68 Howe RdPittsfield, MAOne 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%
|
74 Norman AvePittsfield, MABOM, 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%
|
25 Calumet StPittsfield, MABright 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%
|
44 Strong AvePittsfield, MAGreat 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%
|
195 Churchill StPittsfield, MAJoanne 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%
|
11 Dodge AvePittsfield, MAInvest 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%
|
50-52 John StPittsfield, MA
|
4 beds | 2 baths | 2,132 sq.ft. |
$269,900 |
Airbnb cash on cash: N/A
|
15 Cherry Hill DrPittsfield, MALooking 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%
|
40 Roland StPittsfield, MACory 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%
|
1842 East StPittsfield, MAWendy 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%
|
561 Pecks RdPittsfield, MADouglas 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%
|
40 Baldwin AvePittsfield, MAJuli 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%
|
5 Aspen WayPittsfield, MAGreat 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%
|
33 Alpine TrlPittsfield, MACortney K Dupont [email protected] COHEN & WHITE ASSOCIATES |
5 beds | 4 baths | 3,381 sq.ft. |
$730,000 |
Airbnb cash on cash: 1.97%
|
89 Crofut StPittsfield, MAMaureen 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%
|
156 Draper AvePittsfield, MAThe 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%
|
103 Alpine TrlPittsfield, MACortney K Dupont [email protected] COHEN & WHITE ASSOCIATES |
3 beds | 2 baths | 2,381 sq.ft. |
$759,000 |
Airbnb cash on cash: -1.99%
|
135 Allengate AvePittsfield, MAWith 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%
|
43 Chapman RdPittsfield, MA43 Chapman Rd, Pittsfield, MA 01201 | Single Family Residential |
2 beds | 2 baths | 1,521 sq.ft. |
$409,000 |
Airbnb cash on cash: 1.36%
|
6 Vine StPittsfield, MA6 Vine St, Pittsfield, MA 01201 | Single Family Residential |
2 beds | 1 baths | 1,200 sq.ft. |
$349,900 |
Airbnb cash on cash: 1.96%
|
86 Winesap RdPittsfield, MA86 Winesap Rd, Pittsfield, MA 01201 | Single Family Residential |
3 beds | 2 baths | 2,299 sq.ft. |
$419,000 |
Airbnb cash on cash: 0.31%
|
127 Oak Hill RdPittsfield, MA127 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%
|
10 Marlboro DrPittsfield, MA10 Marlboro Dr, Pittsfield, MA 01201 | Single Family Residential |
3 beds | 1 baths | 1,572 sq.ft. |
$375,000 |
Airbnb cash on cash: 0.61%
|
65 Crofut StPittsfield, MA65 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%
|
100 Northumberland RdPittsfield, MA100 Northumberland Rd, Pittsfield, MA 01201 | Single Family Residential |
4 beds | 4 baths | 3,008 sq.ft. |
$549,000 |
Airbnb cash on cash: 2%
|
41 Highland AvePittsfield, MA41 Highland Ave, Pittsfield, MA 01201 | Single Family Residential |
2 beds | 1 baths | 1,140 sq.ft. |
$220,000 |
Airbnb cash on cash: 4.37%
|
1070 Holmes RdPittsfield, MA1070 Holmes Rd, Pittsfield, MA 01201 | Single Family Residential |
3 beds | 1 baths | 1,563 sq.ft. |
$329,900 |
Airbnb cash on cash: 0.99%
|
551 Tamarack RdPittsfield, MA551 Tamarack Rd, Pittsfield, MA 01201 | Single Family Residential |
4 beds | 2 baths | 2,662 sq.ft. |
$699,900 |
Airbnb cash on cash: 1.1%
|
215 Partridge RdPittsfield, MA215 Partridge Rd, Pittsfield, MA 01201 | Single Family Residential |
3 beds | 1 baths | 1,664 sq.ft. |
$349,000 |
Airbnb cash on cash: 0.81%
|
39 Lowden StPittsfield, MA39 Lowden St, Pittsfield, MA 01201 | Single Family Residential |
3 beds | 2 baths | 1,346 sq.ft. |
$349,900 |
Airbnb cash on cash: 0.81%
|
50 Grand AvePittsfield, MA50 Grand Ave, Pittsfield, MA 01201 | Single Family Residential |
3 beds | 1 baths | 1,152 sq.ft. |
$249,900 |
Airbnb cash on cash: 2%
|
156 Elizabeth StPittsfield, MA156 Elizabeth St, Pittsfield, MA 01201 | Multi Family |
3 beds | 2 baths | 1,454 sq.ft. |
$229,900 |
Airbnb cash on cash: 2.35%
|
51 Foote AvePittsfield, MA
|
3 beds | 1 baths | 1,194 sq.ft. |
$244,900 |
Airbnb cash on cash: 2.08%
|
29 Murphy PlPittsfield, MA29 Murphy Pl, Pittsfield, MA 01201 | Single Family Residential |
3 beds | 1 baths | 1,515 sq.ft. |
$289,900 |
Airbnb cash on cash: 1.42%
|
11 Mcallister StPittsfield, MA11 Mcallister St, Pittsfield, MA 01201 | Single Family Residential |
3 beds | 2 baths | 1,026 sq.ft. |
$289,900 |
Airbnb cash on cash: 1.42%
|
127 Gamwell AvePittsfield, MA127 Gamwell Ave, Pittsfield, MA 01201 | Single Family Residential |
5 beds | 2 baths | 2,120 sq.ft. |
$349,900 |
Airbnb cash on cash: 9.96%
|
36 Pittsfield AvePittsfield, MA36 Pittsfield Ave, Pittsfield, MA 01201 | Single Family Residential |
3 beds | 1 baths | 1,394 sq.ft. |
$312,000 |
Airbnb cash on cash: 1.17%
|
10 Lillybrook RdPittsfield, MA10 Lillybrook Rd, Pittsfield, MA 01201 | Single Family Residential |
4 beds | 3 baths | 2,748 sq.ft. |
$689,900 |
Airbnb cash on cash: 1.15%
|
Real Estate investment in Pittsfield, MA
There are 141 properties for sale in the city of Pittsfield . The median list price in Pittsfield is $299,900 and the average price per square foot is $141. In March 2026, the average monthly cash on cash return in Pittsfield is 7.00%. The average monthly rental income in Pittsfield is $3,023.