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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1481 Marion Road Waterbury, 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%
16 Deepwood Drive Cheshire, CT This three-bedroom home presents a wonderful opportunity for its next owner to unlock its ...	3 beds \| 1 baths \| 1,486 sq.ft.	$274,900	Airbnb cash on cash: -0.48% Traditional cash on cash: 5.59% Airbnb Rental Income: $1137 Traditional Rental Income: $2331 Airbnb ROI: -0.48% Traditional ROI: 5.59%
975 Wolf Hill Road Cheshire, CT Welcome to this beautifully maintained home. The house features hardwood floors throughout...	3 beds \| 3 baths \| 1,882 sq.ft.	$575,000	Airbnb cash on cash: -1.12% Traditional cash on cash: 4.43% Airbnb Rental Income: $1137 Traditional Rental Income: $3737 Airbnb ROI: -1.12% Traditional ROI: 4.43%
621 Wiese Road Cheshire, CT Welcome home to this sweet Cheshire ranch that has been lovingly cared for and is ready fo...	3 beds \| 2 baths \| 1,704 sq.ft.	$499,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 3.87% Airbnb Rental Income: $1137 Traditional Rental Income: $3106 Airbnb ROI: -1.16% Traditional ROI: 3.87%
721 Ives Row Cheshire, CT Spacious Four Bedroom Colonial! Nestled on a large level lot, this home delivers a great o...	4 beds \| 3 baths \| 3,205 sq.ft.	$649,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.34% Airbnb Rental Income: $null Traditional Rental Income: $4419 Airbnb ROI: N/A Traditional ROI: 4.34%
22 Soderman Way PLANTSVILLE, CT Come enjoy nearly new construction at The Reserve at Stonebridge. Built in 2024, this home...	3 beds \| 3 baths \| 2,450 sq.ft.	$699,900	Airbnb cash on cash: -1.44% Traditional cash on cash: 3.92% Airbnb Rental Income: $1137 Traditional Rental Income: $4254 Airbnb ROI: -1.44% Traditional ROI: 3.92%
49 Quarry Village Road unit: 49 #49 Cheshire, CT Welcome to 49 Quarry Village - a beautifully maintained, end-unit condo tucked inside one ...	2 beds \| 3 baths \| 1,700 sq.ft.	$369,900	Airbnb cash on cash: -0.8% Traditional cash on cash: 4.39% Airbnb Rental Income: $1609 Traditional Rental Income: $2955 Airbnb ROI: -0.8% Traditional ROI: 4.39%
35 Stonehenge Place Cheshire, CT Discover the perfect blend of architectural style and natural beauty in this welcoming mid...	4 beds \| 3 baths \| 3,377 sq.ft.	$725,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.72% Airbnb Rental Income: $null Traditional Rental Income: $5016 Airbnb ROI: N/A Traditional ROI: 4.72%
393 E Mitchell Avenue unit: 393 #393 Cheshire, CT 62+ Community. Welcome to Cheshire Hillside Village, a well maintained complex. Heat and h...	1 beds \| 1 baths \| 597 sq.ft.	$149,900	Airbnb cash on cash: 2.13% Traditional cash on cash: 4.42% Airbnb Rental Income: $1677 Traditional Rental Income: $1537 Airbnb ROI: 2.13% Traditional ROI: 4.42%

Real Estate investment in Cheshire, CT

There are 9 properties for sale in the city of Cheshire . The median list price in Cheshire is $612,450 and the average price per square foot is $265. In February 2026, the average monthly cash on cash return in Cheshire is 4.00%. The average monthly rental income in Cheshire is $3,422.

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

There are 9 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 $3,422.

Your search for investment property begins and ends here

Investment Property for Sale in Cheshire, CT

1481 Marion Road

Waterbury, 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%

16 Deepwood Drive

Cheshire, CT

3 beds | 1 baths | 1,486 sq.ft.

$274,900

Airbnb cash on cash: -0.48%

Traditional cash on cash: 5.59%

Airbnb Rental Income: $1137

Traditional Rental Income: $2331

Airbnb ROI: -0.48%

Traditional ROI: 5.59%

975 Wolf Hill Road

Cheshire, CT

3 beds | 3 baths | 1,882 sq.ft.

$575,000

Airbnb cash on cash: -1.12%

Traditional cash on cash: 4.43%

Airbnb Rental Income: $1137

Traditional Rental Income: $3737

Airbnb ROI: -1.12%

Traditional ROI: 4.43%

621 Wiese Road

Cheshire, CT

3 beds | 2 baths | 1,704 sq.ft.

$499,000

Airbnb cash on cash: -1.16%

Traditional cash on cash: 3.87%

Airbnb Rental Income: $1137

Traditional Rental Income: $3106

Airbnb ROI: -1.16%

Traditional ROI: 3.87%

721 Ives Row

Cheshire, CT

4 beds | 3 baths | 3,205 sq.ft.

$649,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.34%

Airbnb Rental Income: $null

Traditional Rental Income: $4419

Airbnb ROI: N/A

Traditional ROI: 4.34%

22 Soderman Way

PLANTSVILLE, CT

3 beds | 3 baths | 2,450 sq.ft.

$699,900

Airbnb cash on cash: -1.44%

Traditional cash on cash: 3.92%

Airbnb Rental Income: $1137

Traditional Rental Income: $4254

Airbnb ROI: -1.44%

Traditional ROI: 3.92%

49 Quarry Village Road unit: 49 #49

Cheshire, CT

2 beds | 3 baths | 1,700 sq.ft.

$369,900

Airbnb cash on cash: -0.8%

Traditional cash on cash: 4.39%

Airbnb Rental Income: $1609

Traditional Rental Income: $2955

Airbnb ROI: -0.8%

Traditional ROI: 4.39%

35 Stonehenge Place

Cheshire, CT

4 beds | 3 baths | 3,377 sq.ft.

$725,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.72%

Airbnb Rental Income: $null

Traditional Rental Income: $5016

Airbnb ROI: N/A