Real Estate Investment Properties for Sale in Chester, NH

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

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
Lot 2 Robin Way #2 Chester, NH Welcome to Chester's newest residential area, Pipit Estates! This new cul-de-sac community...	3 beds \| 2 baths \| 1,550 sq.ft.	$699,900	Airbnb cash on cash: 1.03% Traditional cash on cash: 1.86% Airbnb Rental Income: $3792 Traditional Rental Income: $3511 Airbnb ROI: 1.03% Traditional ROI: 1.86%
Lot 6 Robin Way #6 Chester, NH Jefferson Farmhouse at Pipit Estates Move right into a thoughtfully designed home that bl...	4 beds \| 3 baths \| 2,254 sq.ft.	$765,900	Airbnb cash on cash: 4.34% Traditional cash on cash: 3.19% Airbnb Rental Income: $5935 Traditional Rental Income: $3933 Airbnb ROI: 4.34% Traditional ROI: 3.19%
34 Edwards Mill Road Chester, NH Market Adjustment - Motivated Seller's - If youâre seeking peace and tranquility, this i...	4 beds \| 2 baths \| 2,528 sq.ft.	$795,000	Airbnb cash on cash: 3.98% Traditional cash on cash: 2.51% Airbnb Rental Income: $5935 Traditional Rental Income: $3664 Airbnb ROI: 3.98% Traditional ROI: 2.51%
24 Gypsum Lane #24 Chester, NH WOW More Quality homes by DJ Development. Check out Southwoods Phase 4 in the Quintessenti...	2 beds \| 3 baths \| 1,826 sq.ft.	$559,900	Airbnb cash on cash: -0.06% Traditional cash on cash: 4.7% Airbnb Rental Income: $1624 Traditional Rental Income: $3654 Airbnb ROI: -0.06% Traditional ROI: 4.7%
30 Gypsum Lane #30 Chester, NH WOW more Quality Homes by DJ Development. Check out Southwoods Phase 4 in the Quintessenti...	2 beds \| 3 baths \| 1,826 sq.ft.	$559,900	Airbnb cash on cash: -0.06% Traditional cash on cash: 4.7% Airbnb Rental Income: $1624 Traditional Rental Income: $3654 Airbnb ROI: -0.06% Traditional ROI: 4.7%
23 Holman Way Chester, NH Pride of Ownership with this well maintained colonial which has a list of updates. This is...	3 beds \| 3 baths \| 2,240 sq.ft.	$699,900	Airbnb cash on cash: 2.22% Traditional cash on cash: 3.31% Airbnb Rental Income: $3792 Traditional Rental Income: $3680 Airbnb ROI: 2.22% Traditional ROI: 3.31%
32 Colby Farm Road Chester, NH Experience refined living in this exceptional 5,110 sq. ft. new construction home in the e...	4 beds \| 4 baths \| 5,110 sq.ft.	$2,100,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 1.33% Airbnb Rental Income: $5935 Traditional Rental Income: $5543 Airbnb ROI: 0.93% Traditional ROI: 1.33%
78 Stonebridge Drive Chester, NH Perched atop the coveted cul-de-sac Of Stonebridge Drive, this luxury residence offers a s...	4 beds \| 3 baths \| 3,210 sq.ft.	$1,099,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 1.79% Airbnb Rental Income: $5935 Traditional Rental Income: $4254 Airbnb ROI: 2.28% Traditional ROI: 1.79%
Lot 6 Robin Way Chester, NH Welcome to the Jefferson Farmhouse at Pipit Estates. Why wait this home is complete and re...	4 beds \| 3 baths \| 2,254 sq.ft.	$765,900	Airbnb cash on cash: 3.17% Traditional cash on cash: 2.27% Airbnb Rental Income: $5935 Traditional Rental Income: $4113 Airbnb ROI: 3.17% Traditional ROI: 2.27%
335 Raymond Road Chester, NH Welcome to your brand-new home in the heart of Chester, NH â where quality craftsmanship...	3 beds \| 3 baths \| 1,728 sq.ft.	$729,000	Airbnb cash on cash: 2.93% Traditional cash on cash: 3.4% Airbnb Rental Income: $3792 Traditional Rental Income: $3287 Airbnb ROI: 2.93% Traditional ROI: 3.4%
58 Granite Lane Chester, NH Luxury living at Southwoods Condominiums! This meticulously maintained 2-bedroom, 3-bath h...	2 beds \| 3 baths \| 1,988 sq.ft.	$529,900	Airbnb cash on cash: -1.3% Traditional cash on cash: 3.88% Airbnb Rental Income: $1624 Traditional Rental Income: $3732 Airbnb ROI: -1.3% Traditional ROI: 3.88%

Real Estate investment in Chester, NH

There are 18 properties for sale in the city of Chester . The median list price in Chester is $714,450 and the average price per square foot is $292. In October 2025, the average monthly cash on cash return in Chester is 3.00%. The average monthly rental income in Chester is $3,672.

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

There are 18 investment properties available for sale in Chester.

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

The ROI for Long-Term is higher than the Short-Term in Chester with average rental income of $3,672.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, NH

Lot 2 Robin Way #2

Chester, NH

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

$699,900

Airbnb cash on cash: 1.03%

Traditional cash on cash: 1.86%

Airbnb Rental Income: $3792

Traditional Rental Income: $3511

Airbnb ROI: 1.03%

Traditional ROI: 1.86%

Lot 6 Robin Way #6

Chester, NH

4 beds | 3 baths | 2,254 sq.ft.

$765,900

Airbnb cash on cash: 4.34%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $5935

Traditional Rental Income: $3933

Airbnb ROI: 4.34%

Traditional ROI: 3.19%

34 Edwards Mill Road

Chester, NH

4 beds | 2 baths | 2,528 sq.ft.

$795,000

Airbnb cash on cash: 3.98%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $5935

Traditional Rental Income: $3664

Airbnb ROI: 3.98%

Traditional ROI: 2.51%

24 Gypsum Lane #24

Chester, NH

2 beds | 3 baths | 1,826 sq.ft.

$559,900

Airbnb cash on cash: -0.06%

Traditional cash on cash: 4.7%

Airbnb Rental Income: $1624

Traditional Rental Income: $3654

Airbnb ROI: -0.06%

Traditional ROI: 4.7%

30 Gypsum Lane #30

Chester, NH

2 beds | 3 baths | 1,826 sq.ft.

$559,900

Airbnb cash on cash: -0.06%

Traditional cash on cash: 4.7%

Airbnb Rental Income: $1624

Traditional Rental Income: $3654

Airbnb ROI: -0.06%

Traditional ROI: 4.7%

23 Holman Way

Chester, NH

3 beds | 3 baths | 2,240 sq.ft.

$699,900

Airbnb cash on cash: 2.22%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $3792

Traditional Rental Income: $3680

Airbnb ROI: 2.22%

Traditional ROI: 3.31%

32 Colby Farm Road

Chester, NH

4 beds | 4 baths | 5,110 sq.ft.

$2,100,000

Airbnb cash on cash: 0.93%

Traditional cash on cash: 1.33%

Airbnb Rental Income: $5935

Traditional Rental Income: $5543

Airbnb ROI: 0.93%

Traditional ROI: 1.33%

78 Stonebridge Drive

Chester, NH

4 beds | 3 baths | 3,210 sq.ft.

$1,099,000

Airbnb cash on cash: 2.28%

Traditional cash on cash: 1.79%

Airbnb Rental Income: $5935

Traditional Rental Income: $4254

Airbnb ROI: 2.28%