Is Pittsfield good for short-term rental investments?

Yes, with tourism-driven demand and 7% cap rates, but the 150-day cap balances investor income against housing needs. Focus on properties near cultural sites for best occupancy. Licensing ensures orderly operations.

How does Pittsfield enforce STR regulations?

Multiple departments monitor complaints, using evidence like guest logs and neighbor reports. Violations lead to licensing board review for suspension. The ordinance defines STRs clearly to avoid prior enforcement gaps.

Can STRs operate in affordable housing units?

No, dwellings designated as affordable or income-restricted are prohibited from STR use. This protects long-term housing amid Pittsfield's shortage. Check zoning before investing.

Short Term Rental Investment Properties for Sale in Pittsfield, MA

Property at 20 Westchester Ave, Pittsfield, MA

3 Bed
1 Bath
960 sft

20 Westchester Ave, Pittsfield, MA, 01201

Property at 36 Beacon Ave, Pittsfield, MA

1 Bed
1 Bath
680 sft

36 Beacon Ave, Pittsfield, MA, 01201

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28 Gould St, Ware, MA, 01082

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Property at 140 Chestnut St APT 204, Springfield, MA

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140 Chestnut St APT 204, Springfield, MA, 01103

Property at 83 Clark Rd UNIT 41, Shirley, MA

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83 Clark Rd UNIT 41, Shirley, MA, 01464

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18 Maple St, Pepperell, MA, 01463

Property at 80 Alpine Dr, Southbridge, MA

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80 Alpine Dr, Southbridge, MA, 01550

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80 Alpine, Dudley, MA, 01571

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Property at 46 Atwater Ave, West Brookfield, MA

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46 Atwater Ave, West Brookfield, MA, 01585

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Property at 0 Overlook Rd, Westminster, MA

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Property at LOT 3 W State Rd #3, Ashby, MA

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Property at 519 E River St LOT 127, Orange, MA

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519 E River St LOT 127, Orange, MA, 01364

Property at LOT 3-3.2 East Rd, Charlemont, MA

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Property at 285 Lynn Shore Dr APT 108, Lynn, MA

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285 Lynn Shore Dr APT 108, Lynn, MA, 01902

Property at 19 Lakewood Dr, Pittsfield, MA

2 Bed
1 Bath
1000 sft

19 Lakewood Dr, Pittsfield, MA, 01201

Property at 270 Littleton Rd TRAILER 143, Chelmsford, MA

2 Bed
1 Bath
- sft

270 Littleton Rd TRAILER 143, Chelmsford, MA, 01824

1 Bed
1 Bath
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350 West St #3, Ludlow, MA, 01056

Property at 3132 Cranberry Hwy #59, Buzzards Bay, MA

2 Bed
2 Bath
780 sft

3132 Cranberry Hwy #59, Buzzards Bay, MA, 02532

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77 Newton St, Holyoke, MA, 01040

Property at 310 Old Chatham #D-30, South Dennis, MA

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310 Old Chatham #D-30, South Dennis, MA, 02660

Property at 846 Broadway #1-2, Saugus, MA

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Why Invest in Pittsfield, Massachusetts?

Short-term rentals in Pittsfield, MA offer investors a regulated path to supplemental income, capped at 150 days per year to balance housing needs. The city's new ordinance defines STRs as rentals under 30 days, with licensing and enforcement by multiple departments. Expect solid **rental yields** around 6-8% in the Berkshire region, driven by tourism demand. **Cap rates** hover at 7%, with average rents at $2,200 monthly for suitable properties. Annual appreciation of 4% supports long-term holds amid controlled supply.

8.5%

Avg. ROI

7.2%

Rental Yield

7.1%

Cap Rate

$1850/mo

Avg. Cash Flow

$2200/mo

Avg. Rent

4.2%

1Y Appreciation

Frequently Asked Questions

STRs are rentals under 30 days, limited to 150 days/year per property. Operators must register, get licensed, and designate a local contact in Berkshire County. Enforcement involves zoning, police, fire, and health departments.

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Can STRs operate in affordable housing units?

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