Real Estate Investment Properties for Sale in Chester, CT
Looking for investment property in Chester, CT with high ROI ?
Explore a variety of short-term homes & houses in Chester, CT. Invest wisely with VRBO & Chester, 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 Chester, CT
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
9 Hickory Hill DriveChester, CTWelcome to 9 Hickory Hill Drive! Set high on a hill in the heart of the charming Connectic... |
3 beds | 3 baths | 2,888 sq.ft. |
$799,000 |
Airbnb cash on cash: -0.76%
|
15 Hazen StreetChester, CTBack on market! Inspection will show there is some termite damage in one of beams in basem... |
3 beds | 1 baths | 748 sq.ft. |
$229,000 |
Airbnb cash on cash: 2.11%
|
6 W Main StreetChester, CTEXCELLENT LOCATION, EXCELLENT CONDITION! Lovingly restored 2-family in the heart of Cheste... |
4 beds | 2 baths | 2,160 sq.ft. |
$725,000 |
Airbnb cash on cash: -0.58%
|
8 Butter Jones RoadChester, CTEnchanting Cape with Artisan Post & Beam Charm - Just Down the Road from Chester Village! ... |
3 beds | 3 baths | 2,139 sq.ft. |
$775,000 |
Airbnb cash on cash: -1.87%
|
36 Kings HighwayChester, CTCharming Stone Home on Nearly 4 Acres! Just minutes from Chester Village, this distinctive... |
4 beds | 2 baths | 1,516 sq.ft. |
$469,900 |
Airbnb cash on cash: 0.8%
|
79 Middlesex AvenueChester, CTCharming Cape just steps from Chester Village! This inviting 2-bed, 1-bath home blends tim... |
2 beds | 1 baths | 1,470 sq.ft. |
$449,000 |
Airbnb cash on cash: 0.25%
|
Real Estate investment in Chester, CT
There are 7 properties for sale in the city of Chester . The median list price in Chester is $469,900 and the average price per square foot is $278. In December 2025, the average monthly cash on cash return in Chester is 3.00%. The average monthly rental income in Chester is $3,233.