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 |
|---|---|---|---|
88 Winthrop RoadChester, CTThe charming 3 bedroom colonial with a large attached garage and 2 outbuildings overlooks ... |
2 beds | 3 baths | 2,240 sq.ft. |
$985,000 |
Airbnb cash on cash: -1.93%
|
6 Spring StreetChester, CTWelcome to 6 Spring Street, a residence that transcends the ordinary. Known affectionately... |
2 beds | 3 baths | 1,598 sq.ft. |
$775,000 |
Airbnb cash on cash: -1.6%
|
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: 0.7%
|
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. |
$795,000 |
Airbnb cash on cash: -0.87%
|
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. |
$525,000 |
Airbnb cash on cash: -0.88%
|
28 Hoop Pole Hill RoadChester, CTDiscover the perfect blend of elegance and convenience in this custom Cape Cod home, nestl... |
4 beds | 4 baths | 3,396 sq.ft. |
$774,000 |
Airbnb cash on cash: 0.46%
|
23 Spring StreetChester, CTThis precious 1920 bungalow has had only 2 owners! It has been updated and extremely well ... |
2 beds | 2 baths | 1,104 sq.ft. |
$469,900 |
Airbnb cash on cash: -0.62%
|
Real Estate investment in Chester, CT
There are 10 properties for sale in the city of Chester . The median list price in Chester is $749,500 and the average price per square foot is $383. In October 2025, the average monthly cash on cash return in Chester is 2.00%. The average monthly rental income in Chester is $3,308.