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
121 Overview Drive Jaffrey, NH This isn't another house; it's an unscripted life atop a private knoll. You asked for **vi...	3 beds \| 2 baths \| 2,704 sq.ft.	$475,000	Airbnb cash on cash: 0.57% Traditional cash on cash: 4.28% Airbnb Rental Income: $2257 Traditional Rental Income: $3339 Airbnb ROI: 0.57% Traditional ROI: 4.28%
8 Cross Street Jaffrey, NH Neat Villager! This 2-3 bedroom home has plenty to offer. Walk through the screened porch ...	2 beds \| 1 baths \| 1,334 sq.ft.	$369,900	Airbnb cash on cash: -0.61% Traditional cash on cash: 3.75% Airbnb Rental Income: $1251 Traditional Rental Income: $2367 Airbnb ROI: -0.61% Traditional ROI: 3.75%
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.	$195,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 8.72% Airbnb Rental Income: $1251 Traditional Rental Income: $2327 Airbnb ROI: 0.77% Traditional ROI: 8.72%
715 Gilmore Pond Road Jaffrey, NH Country property with strong antique home and barn. 6 +/- acres that has sub-vision poten...	2 beds \| 2 baths \| 1,368 sq.ft.	$449,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 2.58% Airbnb Rental Income: $1251 Traditional Rental Income: $2237 Airbnb ROI: -0.71% Traditional ROI: 2.58%
137 Prescott Road Jaffrey, NH Steeped in history and timeless charm, this distinguished Colonial home, built circa 1830,...	5 beds \| 3 baths \| 3,564 sq.ft.	$599,900	Airbnb cash on cash: 2% Traditional cash on cash: 4.64% Airbnb Rental Income: $3738 Traditional Rental Income: $4402 Airbnb ROI: 2% Traditional ROI: 4.64%
Roberts Drive #16 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.	$699,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 3.7% Airbnb Rental Income: $2257 Traditional Rental Income: $3773 Airbnb ROI: 0.51% Traditional ROI: 3.7%
Roberts Drive #5 Jaffrey, NH The Hudson is a 4-bedroom 3-bathroom home with a stunning view of Grand Monadnock! The com...	4 beds \| 3 baths \| 2,059 sq.ft.	$784,900	Airbnb cash on cash: 0.44% Traditional cash on cash: 3.35% Airbnb Rental Income: $2342 Traditional Rental Income: $3886 Airbnb ROI: 0.44% Traditional ROI: 3.35%
Roberts Drive #20 Jaffrey, NH The "Paxton" is a 3-bedroom 3-bathroom farmhouse colonial. The combination of ...	3 beds \| 3 baths \| 2,011 sq.ft.	$649,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 4.75% Airbnb Rental Income: $2257 Traditional Rental Income: $4191 Airbnb ROI: 0.63% Traditional ROI: 4.75%
Roberts Drive #7 Jaffrey, NH Meet the "Zara". A 3-bedroom 3-bathroom ranch. The combination of farmhouse styl...	3 beds \| 3 baths \| 2,036 sq.ft.	$799,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 2.94% Airbnb Rental Income: $2257 Traditional Rental Income: $3736 Airbnb ROI: 0.19% Traditional ROI: 2.94%
Roberts Drive #11 Jaffrey, NH Meet the "Copley" ranch! The open floor plan connects the Great Room (with gas f...	3 beds \| 3 baths \| 1,840 sq.ft.	$765,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 3.08% Airbnb Rental Income: $2257 Traditional Rental Income: $3714 Airbnb ROI: 0.24% Traditional ROI: 3.08%
Roberts Drive #26 Jaffrey, NH The "Barkley" is a 2500 sq ft plus 2 story 4-bedroom home with 1st floor primary...	3 beds \| 3 baths \| 2,418 sq.ft.	$799,900	Airbnb cash on cash: 0.19% Traditional cash on cash: 3.23% Airbnb Rental Income: $2257 Traditional Rental Income: $3954 Airbnb ROI: 0.19% Traditional ROI: 3.23%
Roberts Drive #18 Jaffrey, NH The "Paxton" is a 3-bedroom 3-bathroom farmhouse colonial. The combination of ...	3 beds \| 3 baths \| 2,011 sq.ft.	$649,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 3.89% Airbnb Rental Income: $2257 Traditional Rental Income: $3764 Airbnb ROI: 0.46% Traditional ROI: 3.89%
Roberts Drive #24 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: 0.25% Traditional cash on cash: 3.18% Airbnb Rental Income: $2257 Traditional Rental Income: $3764 Airbnb ROI: 0.25% Traditional ROI: 3.18%
57 Prescott Road Jaffrey, NH Enjoy Antique home charm with none of the work! Discover the perfect blend of classic New ...	2 beds \| 2 baths \| 1,788 sq.ft.	$544,900	Airbnb cash on cash: -0.9% Traditional cash on cash: 3.34% Airbnb Rental Income: $1251 Traditional Rental Income: $3015 Airbnb ROI: -0.9% Traditional ROI: 3.34%
24 Red Gate Road Jaffrey, NH SUITABLE FOR YOUR LIFESTYLE! Are you looking for a beautiful country home w/mountain view?...	5 beds \| 4 baths \| 3,872 sq.ft.	$699,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 5.23% Airbnb Rental Income: $3738 Traditional Rental Income: $5417 Airbnb ROI: 1.4% Traditional ROI: 5.23%
49 Roberts Drive #23 Jaffrey, NH Welcome to 49 Roberts Drive in Jaffrey's sought-after Stony Brook Village! This brand...	3 beds \| 2 baths \| 1,774 sq.ft.	$699,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 3.05% Airbnb Rental Income: $2257 Traditional Rental Income: $3447 Airbnb ROI: 0.36% Traditional ROI: 3.05%
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: 0.05% Traditional cash on cash: 4.16% Airbnb Rental Income: $3738 Traditional Rental Income: $6739 Airbnb ROI: 0.05% Traditional ROI: 4.16%
29 Dean Farm Road Jaffrey, NH Youâve got to check out this place on Dean Farm Road. Itâs one of those homes that jus...	5 beds \| 3 baths \| 2,906 sq.ft.	$529,900	Airbnb cash on cash: 2.54% Traditional cash on cash: 5.12% Airbnb Rental Income: $3738 Traditional Rental Income: $4207 Airbnb ROI: 2.54% Traditional ROI: 5.12%
219 Gilmore Pond Road Jaffrey, NH This forested 16 acre hilltop property with a 'sugar shack has had over $600K+ improv...	4 beds \| 3 baths \| 2,596 sq.ft.	$890,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 2.68% Airbnb Rental Income: $2342 Traditional Rental Income: $4136 Airbnb ROI: -0.19% Traditional ROI: 2.68%
175 Hadley Road Jaffrey, NH SIMPLY SPECIAL! Please come see this immaculate 2,910 sf Colonial being sold by itâs ori...	3 beds \| 3 baths \| 2,910 sq.ft.	$775,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 2.56% Airbnb Rental Income: $2257 Traditional Rental Income: $3761 Airbnb ROI: -0.3% Traditional ROI: 2.56%
446 Squantum Road Jaffrey, NH A DIAMOND IN THE ROUGH! This expanded colonial with four bedrooms and two baths has lots o...	4 beds \| 2 baths \| 2,330 sq.ft.	$350,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 7.05% Airbnb Rental Income: $2342 Traditional Rental Income: $3562 Airbnb ROI: 1.58% Traditional ROI: 7.05%

Real Estate investment in Jaffrey, NH

There are 22 properties for sale in the city of Jaffrey . The median list price in Jaffrey is $674,000 and the average price per square foot is $282. In October 2025, the average monthly cash on cash return in Jaffrey is 4.00%. The average monthly rental income in Jaffrey is $3,763.

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

There are 22 investment properties available for sale in Jaffrey.

In 2025, the best neighborhood to buy investment property is Jaffrey.

The ROI for Short-Term is higher than the Long-Term in Jaffrey with average rental income of $2,257.

Your search for investment property begins and ends here

Investment Property for Sale in Jaffrey, NH

121 Overview Drive

Jaffrey, NH

3 beds | 2 baths | 2,704 sq.ft.

$475,000

Airbnb cash on cash: 0.57%

Traditional cash on cash: 4.28%

Airbnb Rental Income: $2257

Traditional Rental Income: $3339

Airbnb ROI: 0.57%

Traditional ROI: 4.28%

8 Cross Street

Jaffrey, NH

2 beds | 1 baths | 1,334 sq.ft.

$369,900

Airbnb cash on cash: -0.61%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $1251

Traditional Rental Income: $2367

Airbnb ROI: -0.61%

Traditional ROI: 3.75%

11 Saint Jean Street

Jaffrey, NH

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

$195,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 8.72%

Airbnb Rental Income: $1251

Traditional Rental Income: $2327

Airbnb ROI: 0.77%

Traditional ROI: 8.72%

715 Gilmore Pond Road

Jaffrey, NH

2 beds | 2 baths | 1,368 sq.ft.

$449,000

Airbnb cash on cash: -0.71%

Traditional cash on cash: 2.58%

Airbnb Rental Income: $1251

Traditional Rental Income: $2237

Airbnb ROI: -0.71%

Traditional ROI: 2.58%

137 Prescott Road

Jaffrey, NH

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

$599,900

Airbnb cash on cash: 2%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $3738

Traditional Rental Income: $4402

Airbnb ROI: 2%

Traditional ROI: 4.64%

Roberts Drive #16

Jaffrey, NH

3 beds | 3 baths | 1,944 sq.ft.

$699,000

Airbnb cash on cash: 0.51%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $2257

Traditional Rental Income: $3773

Airbnb ROI: 0.51%

Traditional ROI: 3.7%

Roberts Drive #5

Jaffrey, NH

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

$784,900

Airbnb cash on cash: 0.44%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $2342

Traditional Rental Income: $3886

Airbnb ROI: 0.44%

Traditional ROI: 3.35%

Roberts Drive #20

Jaffrey, NH

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

$649,000

Airbnb cash on cash: 0.63%

Traditional cash on cash: 4.75%

Airbnb Rental Income: $2257

Traditional Rental Income: $4191

Airbnb ROI: 0.63%