Real Estate Investment Properties for Sale in Jaffrey, NH

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
72 North Street Jaffrey, NH Step into this reimagined 1930s Villager Cape, where classic charm meets modern comfort in...	3 beds \| 2 baths \| 1,134 sq.ft.	$349,900	Airbnb cash on cash: 4.45% Traditional cash on cash: 5.87% Airbnb Rental Income: $3081 Traditional Rental Income: $2846 Airbnb ROI: 4.45% Traditional ROI: 5.87%
58 Proctor Road Jaffrey, NH Attention Homesteaders, or those looking for prime open land. Here you'll find a unique op...	4 beds \| 2 baths \| 2,820 sq.ft.	$895,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 1.88% Airbnb Rental Income: $4198 Traditional Rental Income: $3434 Airbnb ROI: 1.73% Traditional ROI: 1.88%
350 Woodbound Road Jaffrey, NH Welcome to this beautifully updated home in one of Jaffrey's most desirable lake communiti...	2 beds \| 1 baths \| 1,550 sq.ft.	$580,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 2.02% Airbnb Rental Income: $1600 Traditional Rental Income: $2228 Airbnb ROI: 0.02% Traditional ROI: 2.02%
11 Saint Jean Street Jaffrey, NH INVESTORS TAKE NOTE!! This edge of town property is on a quiet dead end street. Bring your...	2 beds \| 1 baths \| 1,433 sq.ft.	$190,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 8.97% Airbnb Rental Income: $1600 Traditional Rental Income: $2327 Airbnb ROI: 2.42% Traditional ROI: 8.97%
137 Prescott Road Jaffrey, NH Nestled in the heart of New Hampshire's beloved Monadnock Region, this remarkable circa 18...	5 beds \| 3 baths \| 3,564 sq.ft.	$599,900	Airbnb cash on cash: 2.26% Traditional cash on cash: 4.78% Airbnb Rental Income: $3817 Traditional Rental Income: $4402 Airbnb ROI: 2.26% Traditional ROI: 4.78%
52 Roberts Drive #5 Jaffrey, NH Meet the "Zara". A 3-bedroom 3-bathroom ranch. The combination of farmhouse styl...	3 beds \| 3 baths \| 2,036 sq.ft.	$899,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 2.44% Airbnb Rental Income: $3081 Traditional Rental Income: $3886 Airbnb ROI: 0.64% Traditional ROI: 2.44%
Roberts Drive Jaffrey, NH The Hudson is a 5-bedroom 3-bathroom home with a stunning view of Grand Monadnock! The com...	4 beds \| 3 baths \| 2,059 sq.ft.	$789,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 2.9% Airbnb Rental Income: $4198 Traditional Rental Income: $3982 Airbnb ROI: 1.98% Traditional ROI: 2.9%
65 Roberts Drive #17 Jaffrey, NH The "Paxton" is a 3-bedroom 3-bathroom farmhouse colonial. The combination of ...	3 beds \| 3 baths \| 2,011 sq.ft.	$759,900	Airbnb cash on cash: 1.22% Traditional cash on cash: 3.18% Airbnb Rental Income: $3081 Traditional Rental Income: $3764 Airbnb ROI: 1.22% Traditional ROI: 3.18%
49 Roberts Drive #23 Jaffrey, NH Grab your hiking boots and golf clubs and move right in! And the seller is offering a 3% r...	3 beds \| 2 baths \| 1,774 sq.ft.	$669,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 3.23% Airbnb Rental Income: $3081 Traditional Rental Income: $3447 Airbnb ROI: 1.52% Traditional ROI: 3.23%
13 Harkness Road Jaffrey, NH Welcome to 13 Harkness Road, a rare opportunity to own a piece of New England history. Ori...	5 beds \| 5 baths \| 5,846 sq.ft.	$997,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 4.16% Airbnb Rental Income: $3817 Traditional Rental Income: $6739 Airbnb ROI: 0.12% Traditional ROI: 4.16%
175 Hadley Road Jaffrey, NH Set on 3.8 picturesque acres with beautiful established landscaping, and the Contoocook Ri...	3 beds \| 3 baths \| 2,910 sq.ft.	$695,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 2.94% Airbnb Rental Income: $3081 Traditional Rental Income: $3761 Airbnb ROI: 0.81% Traditional ROI: 2.94%
56 Roberts Drive #7 Jaffrey, NH The "Barkley" is a 2500 sq ft plus 2 story 3-bedroom home with 1st floor primary...	3 beds \| 3 baths \| 2,271 sq.ft.	$899,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 2.16% Airbnb Rental Income: $3081 Traditional Rental Income: $3752 Airbnb ROI: 0.52% Traditional ROI: 2.16%
18 Roberts Drive #1 Jaffrey, NH Introducing the 'Copley Ranch - another Jewel of Stony Brook Village! Set on a premi...	3 beds \| 3 baths \| 1,840 sq.ft.	$829,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 2.57% Airbnb Rental Income: $3081 Traditional Rental Income: $3904 Airbnb ROI: 0.6% Traditional ROI: 2.57%
57 Roberts Drive #19 Jaffrey, NH The "Tatum" a two-story 3 Bedroom 3 Bathroom Colonial. As you enter into Stony B...	3 beds \| 3 baths \| 1,944 sq.ft.	$779,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 2.58% Airbnb Rental Income: $3081 Traditional Rental Income: $3704 Airbnb ROI: 0.75% Traditional ROI: 2.58%
60 Roberts Drive #8 Jaffrey, NH The "Paxton" is a 3-bedroom 3-bathroom farmhouse colonial. The combination of ...	3 beds \| 3 baths \| 2,011 sq.ft.	$799,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 2.55% Airbnb Rental Income: $3081 Traditional Rental Income: $3752 Airbnb ROI: 0.71% Traditional ROI: 2.55%
40 Roberts Drive #3 Jaffrey, NH The Hudson is a 5-bedroom 3-bathroom home with a stunning view of Grand Monadnock! The com...	5 beds \| 3 baths \| 2,059 sq.ft.	$789,000	Airbnb cash on cash: 1.56% Traditional cash on cash: 3.01% Airbnb Rental Income: $3817 Traditional Rental Income: $4053 Airbnb ROI: 1.56% Traditional ROI: 3.01%
23 Windy Fields Lane Jaffrey, NH Welcome home to this lovely 3-bedroom, 3-bath Cape on Windy Fields Lane in Jaffrey, just t...	3 beds \| 3 baths \| 1,575 sq.ft.	$400,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 5.76% Airbnb Rental Income: $3081 Traditional Rental Income: $3301 Airbnb ROI: 3.3% Traditional ROI: 5.76%

Real Estate investment in Jaffrey, NH

There are 22 properties for sale in the city of Jaffrey . The median list price in Jaffrey is $359,551 and the average price per square foot is $172. In July 2026, the average monthly cash on cash return in Jaffrey is 3.00%. The average monthly rental income in Jaffrey is $3,597.

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

There are 22 investment properties available for sale in Jaffrey.

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

The ROI for Long-Term is higher than the Short-Term in Jaffrey with average rental income of $3,597.

Your search for investment property begins and ends here

Investment Property for Sale in Jaffrey, NH

72 North Street

Jaffrey, NH

3 beds | 2 baths | 1,134 sq.ft.

$349,900

Airbnb cash on cash: 4.45%

Traditional cash on cash: 5.87%

Airbnb Rental Income: $3081

Traditional Rental Income: $2846

Airbnb ROI: 4.45%

Traditional ROI: 5.87%

58 Proctor Road

Jaffrey, NH

4 beds | 2 baths | 2,820 sq.ft.

$895,000

Airbnb cash on cash: 1.73%

Traditional cash on cash: 1.88%

Airbnb Rental Income: $4198

Traditional Rental Income: $3434

Airbnb ROI: 1.73%

Traditional ROI: 1.88%

350 Woodbound Road

Jaffrey, NH

2 beds | 1 baths | 1,550 sq.ft.

$580,000

Airbnb cash on cash: 0.02%

Traditional cash on cash: 2.02%

Airbnb Rental Income: $1600

Traditional Rental Income: $2228

Airbnb ROI: 0.02%

Traditional ROI: 2.02%

11 Saint Jean Street

Jaffrey, NH

2 beds | 1 baths | 1,433 sq.ft.

$190,000

Airbnb cash on cash: 2.42%

Traditional cash on cash: 8.97%

Airbnb Rental Income: $1600

Traditional Rental Income: $2327

Airbnb ROI: 2.42%

Traditional ROI: 8.97%

137 Prescott Road

Jaffrey, NH

5 beds | 3 baths | 3,564 sq.ft.

$599,900

Airbnb cash on cash: 2.26%

Traditional cash on cash: 4.78%

Airbnb Rental Income: $3817

Traditional Rental Income: $4402

Airbnb ROI: 2.26%

Traditional ROI: 4.78%

52 Roberts Drive #5

Jaffrey, NH

3 beds | 3 baths | 2,036 sq.ft.

$899,000

Airbnb cash on cash: 0.64%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $3081

Traditional Rental Income: $3886

Airbnb ROI: 0.64%

Traditional ROI: 2.44%

Roberts Drive

Jaffrey, NH

4 beds | 3 baths | 2,059 sq.ft.

$789,000

Airbnb cash on cash: 1.98%

Traditional cash on cash: 2.9%

Airbnb Rental Income: $4198

Traditional Rental Income: $3982

Airbnb ROI: 1.98%

Traditional ROI: 2.9%

65 Roberts Drive #17

Jaffrey, NH

3 beds | 3 baths | 2,011 sq.ft.

$759,900

Airbnb cash on cash: 1.22%

Traditional cash on cash: 3.18%

Airbnb Rental Income: $3081

Traditional Rental Income: $3764

Airbnb ROI: 1.22%