Real Estate Investment Properties for Sale in Pittsfield, NH

Looking for investment property in Pittsfield, NH with high ROI ?

Explore a variety of short-term homes & houses in Pittsfield, NH. Invest wisely with VRBO & Pittsfield, NH 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, NH

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1457 Upper City Road Pittsfield, NH This one is ready to rise above the rest. Just like the famous Pittsfield hot air balloon ...	3 beds \| 2 baths \| 1,569 sq.ft.	$300,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 8.17% Airbnb Rental Income: $1600 Traditional Rental Income: $3148 Airbnb ROI: 1.08% Traditional ROI: 8.17%
4 Depot Street Pittsfield, NH Strong income property available directly in downtown Pittsfield made up of 4 residential ...	N/A beds \| N/A baths \| 6,726 sq.ft.	$700,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.16% Airbnb Rental Income: $null Traditional Rental Income: $1508 Airbnb ROI: N/A Traditional ROI: -0.16%
14 Chestnut Street Pittsfield, NH Donât miss this excellent opportunity to own a well-maintained and affordable multi-fami...	4 beds \| 2 baths \| 2,162 sq.ft.	$445,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 5.56% Airbnb Rental Income: $2685 Traditional Rental Income: $3462 Airbnb ROI: 2.16% Traditional ROI: 5.56%
2 Depot Street Pittsfield, NH Investors, look no further for a deal of a lifetime. This large 5-unit property offers 6,7...	6 beds \| 5 baths \| 6,769 sq.ft.	$479,900	Airbnb cash on cash: 4.3% Traditional cash on cash: 1.17% Airbnb Rental Income: $3767 Traditional Rental Income: $1545 Airbnb ROI: 4.3% Traditional ROI: 1.17%
268 Mountain Road Pittsfield, NH Welcome to Sunset Hill Farm on the former Knowltons Corner of Pittsfield, NH. Step into a ...	5 beds \| 3 baths \| 5,409 sq.ft.	$999,900	Airbnb cash on cash: 0.75% Traditional cash on cash: 2.44% Airbnb Rental Income: $3767 Traditional Rental Income: $4521 Airbnb ROI: 0.75% Traditional ROI: 2.44%
1310 & 1311 Upper City Road Pittsfield, NH Oh the Views! Perfectly sited, this Quintessential 1780 Colonial Farmhouse is framed by lo...	4 beds \| 4 baths \| 4,156 sq.ft.	$849,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 2.86% Airbnb Rental Income: $2685 Traditional Rental Income: $4466 Airbnb ROI: -0.2% Traditional ROI: 2.86%
79 High Street Pittsfield, NH Incredible opportunity to own this 4 acre parcel at the intersection of Route 28 and River...	6 beds \| 4 baths \| 3,800 sq.ft.	$999,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 3.51% Airbnb Rental Income: $3767 Traditional Rental Income: $5500 Airbnb ROI: 0.77% Traditional ROI: 3.51%
7 Lilac Lane Pittsfield, NH Like new and meticulously maintained, this affordable one-level home offers the perfect bl...	2 beds \| 1 baths \| 977 sq.ft.	$179,900	Airbnb cash on cash: -3.03% Traditional cash on cash: 6.58% Airbnb Rental Income: $986 Traditional Rental Income: $2277 Airbnb ROI: -3.03% Traditional ROI: 6.58%
73 Bailey Drive Pittsfield, NH This terrific home is in one of those neighborhoods that makes you instantly feel at home!...	3 beds \| 3 baths \| 1,872 sq.ft.	$589,900	Airbnb cash on cash: -0.58% Traditional cash on cash: 4% Airbnb Rental Income: $1600 Traditional Rental Income: $3667 Airbnb ROI: -0.58% Traditional ROI: 4%
2 Depot & 27 Carroll Street Pittsfield, NH 4 separate lots packaged, and approximately 20,000 SF between two large buildings with pot...	7 beds \| 10 baths \| 16,057 sq.ft.	$729,900	Airbnb cash on cash: 1.03% Traditional cash on cash: 8.52% Airbnb Rental Income: $3767 Traditional Rental Income: $8044 Airbnb ROI: 1.03% Traditional ROI: 8.52%
28 Catamount Road Pittsfield, NH Move-in ready home with an attached carport and public water and sewer on an easily mainta...	2 beds \| 2 baths \| 1,313 sq.ft.	$279,900	Airbnb cash on cash: -0.55% Traditional cash on cash: 7.23% Airbnb Rental Income: $986 Traditional Rental Income: $2685 Airbnb ROI: -0.55% Traditional ROI: 7.23%
215 Leavitt Road Pittsfield, NH 3-bedroom, 2-bath home on 2+ acres in Pittsfield! This move-in-ready home offers a peacef...	3 beds \| 2 baths \| 1,140 sq.ft.	$274,900	Airbnb cash on cash: 1.38% Traditional cash on cash: 7.78% Airbnb Rental Income: $1600 Traditional Rental Income: $2805 Airbnb ROI: 1.38% Traditional ROI: 7.78%

Real Estate investment in Pittsfield, NH

There are 17 properties for sale in the city of Pittsfield . The median list price in Pittsfield is $321,834 and the average price per square foot is $136. In June 2026, the average monthly cash on cash return in Pittsfield is 6.00%. The average monthly rental income in Pittsfield is $3,305.

Pittsfield, NH Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 17 investment properties available for sale in Pittsfield.

In 2026, the best neighborhood to buy investment property is Pittsfield.

The ROI for Long-Term is higher than the Short-Term in Pittsfield with average rental income of $3,305.

Your search for investment property begins and ends here

Investment Property for Sale in Pittsfield, NH

1457 Upper City Road

Pittsfield, NH

3 beds | 2 baths | 1,569 sq.ft.

$300,000

Airbnb cash on cash: 1.08%

Traditional cash on cash: 8.17%

Airbnb Rental Income: $1600

Traditional Rental Income: $3148

Airbnb ROI: 1.08%

Traditional ROI: 8.17%

4 Depot Street

Pittsfield, NH

N/A beds | N/A baths | 6,726 sq.ft.

$700,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.16%

Airbnb Rental Income: $null

Traditional Rental Income: $1508

Airbnb ROI: N/A

Traditional ROI: -0.16%

14 Chestnut Street

Pittsfield, NH

4 beds | 2 baths | 2,162 sq.ft.

$445,000

Airbnb cash on cash: 2.16%

Traditional cash on cash: 5.56%

Airbnb Rental Income: $2685

Traditional Rental Income: $3462

Airbnb ROI: 2.16%

Traditional ROI: 5.56%

2 Depot Street

Pittsfield, NH

6 beds | 5 baths | 6,769 sq.ft.

$479,900

Airbnb cash on cash: 4.3%

Traditional cash on cash: 1.17%

Airbnb Rental Income: $3767

Traditional Rental Income: $1545

Airbnb ROI: 4.3%

Traditional ROI: 1.17%

268 Mountain Road

Pittsfield, NH

5 beds | 3 baths | 5,409 sq.ft.

$999,900

Airbnb cash on cash: 0.75%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $3767

Traditional Rental Income: $4521

Airbnb ROI: 0.75%

Traditional ROI: 2.44%

1310 & 1311 Upper City Road

Pittsfield, NH

4 beds | 4 baths | 4,156 sq.ft.

$849,000

Airbnb cash on cash: -0.2%

Traditional cash on cash: 2.86%

Airbnb Rental Income: $2685

Traditional Rental Income: $4466

Airbnb ROI: -0.2%

Traditional ROI: 2.86%

79 High Street

Pittsfield, NH

6 beds | 4 baths | 3,800 sq.ft.

$999,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 3.51%

Airbnb Rental Income: $3767

Traditional Rental Income: $5500

Airbnb ROI: 0.77%

Traditional ROI: 3.51%

7 Lilac Lane

Pittsfield, NH

2 beds | 1 baths | 977 sq.ft.

$179,900

Airbnb cash on cash: -3.03%

Traditional cash on cash: 6.58%

Airbnb Rental Income: $986

Traditional Rental Income: $2277

Airbnb ROI: -3.03%