Real Estate Investment Properties for Sale in Cheshire, MA

Looking for investment property in Cheshire, MA with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
No properties are listed in Cheshire, Massachusetts at the moment.
Other Investment Properties for Sale in Massachusetts
575 Broad St #315 Weymouth , MA 575 Broad St #315, Weymouth, MA 02189 \| Condo/Coop	2 beds \| 1 baths \| 851 sq.ft.	$329,900	Airbnb cash on cash: -1.22% Traditional cash on cash: 2.36% Airbnb Rental Income: $1508 Traditional Rental Income: $2180 Airbnb ROI: -1.22% Traditional ROI: 2.36%
671-673 Boylston St #2 Boston , MA 671-673 Boylston St #2, Boston, MA 02116 \| Condo/Coop	1 beds \| 2 baths \| 1,867 sq.ft.	$2,250,000	Airbnb cash on cash: -2.19% Traditional cash on cash: -1.59% Airbnb Rental Income: $1893 Traditional Rental Income: $2639 Airbnb ROI: -2.19% Traditional ROI: -1.59%
99 E Brookline St #2 Boston , MA 99 E Brookline St #2, Boston, MA 02118 \| Condo/Coop	2 beds \| 1 baths \| 660 sq.ft.	$649,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 0.57% Airbnb Rental Income: $3176 Traditional Rental Income: $2086 Airbnb ROI: 1.18% Traditional ROI: 0.57%
32 Lime St Boston , MA	4 beds \| 5 baths \| 5,194 sq.ft.	$8,850,000	Airbnb cash on cash: -1.82% Traditional cash on cash: -1.43% Airbnb Rental Income: $4345 Traditional Rental Income: $6608 Airbnb ROI: -1.82% Traditional ROI: -1.43%
198 Byron St Boston , MA 198 Byron St, Boston, MA 02128 \| Single Family Residential	3 beds \| 1 baths \| 2,385 sq.ft.	$1,150,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 0.22% Airbnb Rental Income: $4746 Traditional Rental Income: $2708 Airbnb ROI: 1.21% Traditional ROI: 0.22%
764 Cambridge St #6 Cambridge , MA 764 Cambridge St #6, Cambridge, MA 02141 \| Condo/Coop	1 beds \| 1 baths \| 620 sq.ft.	$490,000	Airbnb cash on cash: 4.19% Traditional cash on cash: 0.94% Airbnb Rental Income: $4375 Traditional Rental Income: $1971 Airbnb ROI: 4.19% Traditional ROI: 0.94%
1 Franklin St #1205 Boston , MA Move in and see why Millennium Tower Boston is the evolution of luxury residential living!...	2 beds \| 2 baths \| 1,161 sq.ft.	$1,700,000	Airbnb cash on cash: -2.14% Traditional cash on cash: 0.15% Airbnb Rental Income: $2541 Traditional Rental Income: $5552 Airbnb ROI: -2.14% Traditional ROI: 0.15%
65 Victoria Heights Rd #65 Boston , MA 65 Victoria Heights Rd #65, Boston, MA 02136 \| Townhouse	3 beds \| 2 baths \| 1,793 sq.ft.	$425,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 4.11% Airbnb Rental Income: $3257 Traditional Rental Income: $3279 Airbnb ROI: 2.21% Traditional ROI: 4.11%
141 South St #2 Boston , MA 141 South St #2, Boston, MA 02130 \| Condo/Coop	2 beds \| 1 baths \| 852 sq.ft.	$599,000	Airbnb cash on cash: 1.09% Traditional cash on cash: 0.61% Airbnb Rental Income: $2892 Traditional Rental Income: $1956 Airbnb ROI: 1.09% Traditional ROI: 0.61%
14 Avondale St Boston , MA 14 Avondale St, Boston, MA 02124 \| Single Family Residential	4 beds \| 2 baths \| 1,768 sq.ft.	$679,900	Airbnb cash on cash: 0.88% Traditional cash on cash: 3.31% Airbnb Rental Income: $2700 Traditional Rental Income: $3600 Airbnb ROI: 0.88% Traditional ROI: 3.31%
496 Shore Road unit: 21 #21 Truro , MA The Captains Quarters, is the most sought after '' YEAR ROUND'', rental and investment pro...	3 beds \| 2 baths \| 2,018 sq.ft.	$1,299,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 0.78% Airbnb Rental Income: $2850 Traditional Rental Income: $3609 Airbnb ROI: -0.4% Traditional ROI: 0.78%
73 Joshua Jethro Road Chatham , MA PERFECT HOUSE FOR A POOL! Located in Chatham's highly sought after Riverbay Estates commun...	3 beds \| 2 baths \| 2,307 sq.ft.	$1,520,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 1.11% Airbnb Rental Income: $2063 Traditional Rental Income: $3418 Airbnb ROI: -0.23% Traditional ROI: 1.11%
7915 Eastern Ave #1011 Washington , DC 7915 Eastern Ave #1011, Washington, DC 20910 \| Condo/Coop	2 beds \| 2 baths \| 1,032 sq.ft.	$365,000	Airbnb cash on cash: -2.22% Traditional cash on cash: 1.3% Airbnb Rental Income: $1003 Traditional Rental Income: $1853 Airbnb ROI: -2.22% Traditional ROI: 1.3%
8005 13th St #411 Washington , DC 8005 13th St #411, Washington, DC 20910 \| Condo/Coop	1 beds \| 1 baths \| 1,039 sq.ft.	$325,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 2.57% Airbnb Rental Income: $1600 Traditional Rental Income: $2036 Airbnb ROI: -0.34% Traditional ROI: 2.57%
77 Court St #107 Newton , MA 77 Court St #107, Newton, MA 02458 \| Condo/Coop	2 beds \| 2 baths \| 1,575 sq.ft.	$1,185,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 0.49% Airbnb Rental Income: $2988 Traditional Rental Income: $3713 Airbnb ROI: -0.79% Traditional ROI: 0.49%

Real Estate investment in Cheshire, MA

There are 0 properties for sale in the city of Cheshire . The median list price in Cheshire is $670,000 and the average price per square foot is $300. In March 2026, the average monthly cash on cash return in Cheshire is 5.00%. The average monthly rental income in Cheshire is $3,448.

Cheshire, MA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 0 investment properties available for sale in Cheshire.

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

The ROI for Long-Term is higher than the Short-Term in Cheshire with average rental income of $3,448.

Your search for investment property begins and ends here

Investment Property for Sale in Cheshire, MA

Other Investment Properties for Sale in Massachusetts

Weymouth , MA

2 beds | 1 baths | 851 sq.ft.

$329,900

Airbnb cash on cash: -1.22%

Traditional cash on cash: 2.36%

Airbnb Rental Income: $1508

Traditional Rental Income: $2180

Airbnb ROI: -1.22%

Traditional ROI: 2.36%

Boston , MA

1 beds | 2 baths | 1,867 sq.ft.

$2,250,000

Airbnb cash on cash: -2.19%

Traditional cash on cash: -1.59%

Airbnb Rental Income: $1893

Traditional Rental Income: $2639

Airbnb ROI: -2.19%

Traditional ROI: -1.59%

Boston , MA

2 beds | 1 baths | 660 sq.ft.

$649,000

Airbnb cash on cash: 1.18%

Traditional cash on cash: 0.57%

Airbnb Rental Income: $3176

Traditional Rental Income: $2086

Airbnb ROI: 1.18%

Traditional ROI: 0.57%

Boston , MA

4 beds | 5 baths | 5,194 sq.ft.

$8,850,000

Airbnb cash on cash: -1.82%

Traditional cash on cash: -1.43%

Airbnb Rental Income: $4345

Traditional Rental Income: $6608

Airbnb ROI: -1.82%

Traditional ROI: -1.43%

Boston , MA

3 beds | 1 baths | 2,385 sq.ft.

$1,150,000

Airbnb cash on cash: 1.21%

Traditional cash on cash: 0.22%

Airbnb Rental Income: $4746

Traditional Rental Income: $2708

Airbnb ROI: 1.21%

Traditional ROI: 0.22%

Cambridge , MA

1 beds | 1 baths | 620 sq.ft.

$490,000

Airbnb cash on cash: 4.19%

Traditional cash on cash: 0.94%

Airbnb Rental Income: $4375

Traditional Rental Income: $1971

Airbnb ROI: 4.19%

Traditional ROI: 0.94%

Boston , MA

2 beds | 2 baths | 1,161 sq.ft.

$1,700,000

Airbnb cash on cash: -2.14%

Traditional cash on cash: 0.15%

Airbnb Rental Income: $2541

Traditional Rental Income: $5552

Airbnb ROI: -2.14%

Traditional ROI: 0.15%

Boston , MA

3 beds | 2 baths | 1,793 sq.ft.

$425,000

Airbnb cash on cash: 2.21%

Traditional cash on cash: 4.11%

Airbnb Rental Income: $3257

Traditional Rental Income: $3279

Airbnb ROI: 2.21%

Traditional ROI: 4.11%

Boston , MA

2 beds | 1 baths | 852 sq.ft.

$599,000

Airbnb cash on cash: 1.09%

Traditional cash on cash: 0.61%

Airbnb Rental Income: $2892