Real Estate Investment Properties for Sale in Cheshire, CT

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

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2 Currier Court #2 Cheshire, CT Currier Woods is located in a 160-unit community known for its mature trees, private windi...	2 beds \| 2 baths \| 1,362 sq.ft.	$319,900	Airbnb cash on cash: 1.62% Traditional cash on cash: 5.57% Airbnb Rental Income: $1889 Traditional Rental Income: $2572 Airbnb ROI: 1.62% Traditional ROI: 5.57%
1 Mountaincrest Drive Cheshire, CT PREMIUM WOOD FLOORS JUST INSTALLED in this Mountaincrest custom colonial showcasing luxuri...	4 beds \| 5 baths \| 4,791 sq.ft.	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.04% Airbnb Rental Income: $null Traditional Rental Income: $8439 Airbnb ROI: N/A Traditional ROI: 5.04%
87 Curve Hill Road Cheshire, CT Enjoy the ease and comfort of single-level living in this beautifully maintained 3-bedroom...	3 beds \| 2 baths \| 1,282 sq.ft.	$419,900	Airbnb cash on cash: 0.77% Traditional cash on cash: 4.38% Airbnb Rental Income: $1826 Traditional Rental Income: $2753 Airbnb ROI: 0.77% Traditional ROI: 4.38%
159 Birch Drive Cheshire, CT Built in 2004, this wonderful home offers a tranquil retreat with convenient access to I-8...	4 beds \| 3 baths \| 1,848 sq.ft.	$455,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.7% Airbnb Rental Income: $null Traditional Rental Income: $3444 Airbnb ROI: N/A Traditional ROI: 5.7%
258 Argyle Road Cheshire, CT Dream location! Perfectly positioned in a sought-after neighborhood with sidewalks and a w...	3 beds \| 3 baths \| 2,322 sq.ft.	$494,900	Airbnb cash on cash: 0.5% Traditional cash on cash: 5.69% Airbnb Rental Income: $1826 Traditional Rental Income: $3738 Airbnb ROI: 0.5% Traditional ROI: 5.69%
70 Southwick Court #110 Cheshire, CT Located in the Southwick community, this 55+ condo is conveniently located on the first fl...	1 beds \| 1 baths \| 875 sq.ft.	$219,900	Airbnb cash on cash: 0.64% Traditional cash on cash: 3.63% Airbnb Rental Income: $1764 Traditional Rental Income: $1902 Airbnb ROI: 0.64% Traditional ROI: 3.63%
1481 Marion Road Cheshire, CT Inquire about special builder incentives available until June 30th! Welcome to Blackberry ...	4 beds \| 3 baths \| 3,775 sq.ft.	$1,299,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.7% Airbnb Rental Income: $null Traditional Rental Income: $4717 Airbnb ROI: N/A Traditional ROI: 0.7%
264 Timber Lane Cheshire, CT Charming ranch with endless potential! Welcome to this delightful ranch-style home nestled...	3 beds \| 2 baths \| 1,350 sq.ft.	$420,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 3.78% Airbnb Rental Income: $1826 Traditional Rental Income: $2808 Airbnb ROI: 0.03% Traditional ROI: 3.78%
2 Tunxis Place Cheshire, CT NEW PRICE !!! Exceptional, rare, COPPER HILL Stand Alone Ranch..Most desirable, private, c...	3 beds \| 3 baths \| 2,637 sq.ft.	$619,800	Airbnb cash on cash: -1.77% Traditional cash on cash: 2.61% Airbnb Rental Income: $1826 Traditional Rental Income: $3865 Airbnb ROI: -1.77% Traditional ROI: 2.61%
50 Wintergreen Lane Cheshire, CT Location-Peace and Tranquility is offered with this beautiful well maintained home located...	3 beds \| 3 baths \| 1,901 sq.ft.	$564,900	Airbnb cash on cash: -0.77% Traditional cash on cash: 3.45% Airbnb Rental Income: $1826 Traditional Rental Income: $3563 Airbnb ROI: -0.77% Traditional ROI: 3.45%
50 Abrams Road Cheshire, CT Welcome to a spectacular retreat in Southern Cheshire's coveted Mountaincrest neighborhood...	4 beds \| 3 baths \| 4,981 sq.ft.	$1,500,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.22% Airbnb Rental Income: $null Traditional Rental Income: $4764 Airbnb ROI: N/A Traditional ROI: 0.22%
497 Maple Avenue Cheshire, CT Welcome to 497 Maple Ave! This charming colonial features over 2,300 sq. ft. of living spa...	3 beds \| 3 baths \| 2,396 sq.ft.	$475,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 6.14% Airbnb Rental Income: $1826 Traditional Rental Income: $4210 Airbnb ROI: -0.33% Traditional ROI: 6.14%
471 Spring Street Cheshire, CT HIGHEST AND BEST TOMORROW, 9/12 AT 2 PM. School's back in session, and this Cape is handin...	4 beds \| 2 baths \| 1,349 sq.ft.	$420,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.37% Airbnb Rental Income: $null Traditional Rental Income: $3041 Airbnb ROI: N/A Traditional ROI: 4.37%
130 Edwards Road Cheshire, CT Welcome to this spacious ranch, ideally situated in a desirable neighborhood with sidewalk...	3 beds \| 3 baths \| 2,042 sq.ft.	$455,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 5.89% Airbnb Rental Income: $1826 Traditional Rental Income: $3931 Airbnb ROI: -0.21% Traditional ROI: 5.89%
106 Woodland Drive Cheshire, CT Endless potential in this 3-bedroom, 1.5-bath ranch in Cheshire. Set on a quiet lot with a...	3 beds \| 2 baths \| 1,516 sq.ft.	$349,900	Airbnb cash on cash: 0.66% Traditional cash on cash: 5.86% Airbnb Rental Income: $1826 Traditional Rental Income: $3044 Airbnb ROI: 0.66% Traditional ROI: 5.86%

Real Estate investment in Cheshire, CT

There are 27 properties for sale in the city of Cheshire . The median list price in Cheshire is $475,000 and the average price per square foot is $222. In October 2025, the average monthly cash on cash return in Cheshire is 4.00%. The average monthly rental income in Cheshire is $3,504.

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

There are 27 investment properties available for sale in Cheshire.

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

The ROI for Short-Term is higher than the Long-Term in Cheshire with average rental income of $1,826.

Your search for investment property begins and ends here

Investment Property for Sale in Cheshire, CT

2 Currier Court #2

Cheshire, CT

2 beds | 2 baths | 1,362 sq.ft.

$319,900

Airbnb cash on cash: 1.62%

Traditional cash on cash: 5.57%

Airbnb Rental Income: $1889

Traditional Rental Income: $2572

Airbnb ROI: 1.62%

Traditional ROI: 5.57%

1 Mountaincrest Drive

Cheshire, CT

4 beds | 5 baths | 4,791 sq.ft.

$1,200,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.04%

Airbnb Rental Income: $null

Traditional Rental Income: $8439

Airbnb ROI: N/A

Traditional ROI: 5.04%

87 Curve Hill Road

Cheshire, CT

3 beds | 2 baths | 1,282 sq.ft.

$419,900

Airbnb cash on cash: 0.77%

Traditional cash on cash: 4.38%

Airbnb Rental Income: $1826

Traditional Rental Income: $2753

Airbnb ROI: 0.77%

Traditional ROI: 4.38%

159 Birch Drive

Cheshire, CT

4 beds | 3 baths | 1,848 sq.ft.

$455,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.7%

Airbnb Rental Income: $null

Traditional Rental Income: $3444

Airbnb ROI: N/A

Traditional ROI: 5.7%

258 Argyle Road

Cheshire, CT

3 beds | 3 baths | 2,322 sq.ft.

$494,900

Airbnb cash on cash: 0.5%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $1826

Traditional Rental Income: $3738

Airbnb ROI: 0.5%

Traditional ROI: 5.69%

70 Southwick Court #110

Cheshire, CT

1 beds | 1 baths | 875 sq.ft.

$219,900

Airbnb cash on cash: 0.64%

Traditional cash on cash: 3.63%

Airbnb Rental Income: $1764

Traditional Rental Income: $1902

Airbnb ROI: 0.64%

Traditional ROI: 3.63%

1481 Marion Road

Cheshire, CT

4 beds | 3 baths | 3,775 sq.ft.

$1,299,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.7%

Airbnb Rental Income: $null

Traditional Rental Income: $4717

Airbnb ROI: N/A

Traditional ROI: 0.7%

264 Timber Lane

Cheshire, CT

3 beds | 2 baths | 1,350 sq.ft.

$420,000

Airbnb cash on cash: 0.03%

Traditional cash on cash: 3.78%

Airbnb Rental Income: $1826

Traditional Rental Income: $2808

Airbnb ROI: 0.03%