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 |
|---|---|---|---|
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: -0.06%
|
50 W Housatonic StPittsfield, MA
|
3 beds | 3 baths | 5,392 sq.ft. |
$298,000 |
Airbnb cash on cash: 0.41%
|
15 Cherry Hill DrPittsfield, MABerkshire 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: -1.22%
|
33 Eleanor RdPittsfield, MAAndrew Manns [email protected] 413-329-0972 BERKSHIRE DREAM HOME, INC. |
4 beds | 2 baths | 2,197 sq.ft. |
$464,900 |
Airbnb cash on cash: 1.39%
|
34 Hungerford StPittsfield, MAMichael Harrigan [email protected] 413-429-7788 BERKSHIRE HATHAWAY HOMESERVICES ... |
2 beds | 1 baths | 1,032 sq.ft. |
$309,000 |
Airbnb cash on cash: 1.05%
|
28 Hopewell DrPittsfield, MAMeticulously 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: 0.08%
|
561 Pecks RdPittsfield, MADouglas Collins [email protected] 413-281-6660 BERKSHIRE DREAM HOME, INC. |
2 beds | 2 baths | 1,136 sq.ft. |
$530,000 |
Airbnb cash on cash: -0.54%
|
57 Adam StPittsfield, MAConveniently located near downtown Pittsfield, this home offers an affordable opportunity ... |
4 beds | 1 baths | 1,480 sq.ft. |
$195,000 |
Airbnb cash on cash: 6.12%
|
319 Fenn StPittsfield, MA
|
6 beds | 4 baths | 3,087 sq.ft. |
$445,000 |
Airbnb cash on cash: 0.59%
|
77 Imperial AvePittsfield, MABuy through Auction.com. This foreclosure property is a great opportunity to invest in thi... |
3 beds | 1 baths | 1,326 sq.ft. |
$299,900 |
Airbnb cash on cash: -0.2%
|
243 Robbins AvePittsfield, MAGreat opportunity for investors or residential use renovated 2-bedroom home. Currently occ... |
2 beds | 1 baths | 747 sq.ft. |
$169,900 |
Airbnb cash on cash: 2.47%
|
76 Kenilworth StPittsfield, MAEnchanting Brick Charmer! This home feels like a place where fairytales come to life! Ve... |
3 beds | 2 baths | 1,994 sq.ft. |
$445,000 |
Airbnb cash on cash: -1.23%
|
5 Aspen WayPittsfield, MAGreat 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: -0.3%
|
3 Clarendon StPittsfield, MAStart the New Year in style at 3 Clarendon Street! This newly renovated 3-bedroom, 2-bathr... |
3 beds | 2 baths | 1,092 sq.ft. |
$289,900 |
Airbnb cash on cash: 0.57%
|
33 Alpine TrlPittsfield, MABeautiful 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: -0.45%
|
103 Alpine TrlPittsfield, MAThoughtfully updated end unit located at the Pines at Bousquet The first level includes a ... |
3 beds | 2 baths | 2,381 sq.ft. |
$759,000 |
Airbnb cash on cash: -2.6%
|
135 Allengate AvePittsfield, MAThis 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: -0.9%
|
10 Lillybrook RdPittsfield, MA10 Lillybrook Rd, Pittsfield, MA 01201 | Single Family Residential |
4 beds | 3 baths | 2,748 sq.ft. |
$675,000 |
Airbnb cash on cash: 0.25%
|
144 Brombach StPittsfield, MA144 Brombach St, Pittsfield, MA 01201 | Single Family Residential |
6 beds | 3 baths | 4,034 sq.ft. |
$525,900 |
Airbnb cash on cash: 2.43%
|
5 Crofut StPittsfield, MA5 Crofut St, Pittsfield, MA 01201 | Single Family Residential |
5 beds | 3 baths | 3,370 sq.ft. |
$889,900 |
Airbnb cash on cash: 0.54%
|
168-174 Elm StPittsfield, MA168-174 Elm St, Pittsfield, MA 01201 | Multi Family |
3 beds | 4 baths | 5,640 sq.ft. |
$579,900 |
Airbnb cash on cash: 2%
|
61 Tor Court CtPittsfield, MA61 Tor Court Ct, Pittsfield, MA 01201 | Single Family Residential |
3 beds | 2 baths | 1,728 sq.ft. |
$1,349,000 |
Airbnb cash on cash: -1.74%
|
411 Churchill StPittsfield, MA411 Churchill St, Pittsfield, MA 01201 | Single Family Residential |
4 beds | 3 baths | 2,634 sq.ft. |
$1,101,800 |
Airbnb cash on cash: -0.7%
|
407 Churchill StPittsfield, MA407 Churchill St, Pittsfield, MA 01201 | Single Family Residential |
3 beds | 2 baths | 2,000 sq.ft. |
$814,900 |
Airbnb cash on cash: -1.42%
|
403 Churchill StPittsfield, MA403 Churchill St, Pittsfield, MA 01201 | Single Family Residential |
3 beds | 2 baths | 2,000 sq.ft. |
$789,900 |
Airbnb cash on cash: -1.4%
|
Churchill StPittsfield, MAChurchill St, Pittsfield, MA 01201 | Other |
N/A beds | N/A baths | 2,000 sq.ft. |
$380,000 |
Airbnb cash on cash: N/A
|
365 Churchill StPittsfield, MA365 Churchill St, Pittsfield, MA 01201 | Other |
N/A beds | N/A baths | N/A |
$155,000 |
Airbnb cash on cash: N/A
|
17 S Church StPittsfield, MA17 S Church St, Pittsfield, MA 01201 | Single Family Residential |
4 beds | 2 baths | 1,408 sq.ft. |
$265,000 |
Airbnb cash on cash: 4.02%
|
14 Highland AvePittsfield, MA14 Highland Ave, Pittsfield, MA 01201 | Multi Family |
16 beds | 8 baths | 8,608 sq.ft. |
$1,347,500 |
Airbnb cash on cash: -0.98%
|
140 Hancock RdPittsfield, MA140 Hancock Rd, Pittsfield, MA 01201 | Single Family Residential |
8 beds | 6 baths | 7,494 sq.ft. |
$3,800,000 |
Airbnb cash on cash: -1.58%
|
312 South StPittsfield, MA312 South St, Pittsfield, MA 01201 | Multi Family |
7 beds | 4 baths | 4,682 sq.ft. |
$419,000 |
Airbnb cash on cash: N/A
|
33 Maplewood Ave #103Pittsfield, MAIf 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: -2.97%
|
58 Churchill CrstPittsfield, MA58 Churchill Crst, Pittsfield, MA 01201 | Condo/Coop |
2 beds | 1 baths | 1,227 sq.ft. |
$255,000 |
Airbnb cash on cash: 0.81%
|
2 Amy CtPittsfield, MA2 Amy Ct, Pittsfield, MA 01201 | Single Family Residential |
4 beds | 3 baths | 3,561 sq.ft. |
$569,900 |
Airbnb cash on cash: 0.71%
|
2 Amy Ct #2Pittsfield, MA2 Amy Ct #2, Pittsfield, MA 01201 | Condo/Coop |
4 beds | 3 baths | 3,561 sq.ft. |
$569,900 |
Airbnb cash on cash: 0.08%
|
500 Williams StPittsfield, MA500 Williams St, Pittsfield, MA 01201 | Single Family Residential |
6 beds | 4 baths | 7,894 sq.ft. |
$2,100,000 |
Airbnb cash on cash: -1.05%
|
306 South StPittsfield, MA306 South St, Pittsfield, MA 01201 | Multi Family |
37 beds | 22 baths | 21,162 sq.ft. |
$1,719,000 |
Airbnb cash on cash: -1.84%
|
1450 North St #107Pittsfield, MA1450 North St #107, Pittsfield, MA 01201 | Condo/Coop |
3 beds | 2 baths | 1,500 sq.ft. |
$339,900 |
Airbnb cash on cash: -1.7%
|
969 Dalton AvePittsfield, MA969 Dalton Ave, Pittsfield, MA 01201 | Single Family Residential |
2 beds | 1 baths | 2,234 sq.ft. |
$199,000 |
Airbnb cash on cash: 1.64%
|
122 Blythewood DrPittsfield, MA122 Blythewood Dr, Pittsfield, MA 01201 | Single Family Residential |
3 beds | 3 baths | 3,091 sq.ft. |
$1,999,000 |
Airbnb cash on cash: -1.9%
|
Real Estate investment in Pittsfield, MA
There are 118 properties for sale in the city of Pittsfield . The median list price in Pittsfield is $317,331 and the average price per square foot is $127. In June 2026, the average monthly cash on cash return in Pittsfield is 7.00%. The average monthly rental income in Pittsfield is $3,169.