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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
611 Ives RowCheshire, CTAct Fast... This Rare Gem Won't Last! Tucked away in the peaceful and highly sought-after ... |
3 beds | 2 baths | 1,788 sq.ft. |
$435,000 |
Airbnb cash on cash: -0.91%
|
1481 Marion RoadCheshire, CTWelcome to Blackberry Woods, Cheshire's newest neighborhood! This private, secluded lot pr... |
4 beds | 3 baths | 3,775 sq.ft. |
$1,299,000 |
Airbnb cash on cash: N/A
|
365 Maple AvenueCheshire, CTWelcome to 365 Maple Ave, a quintessential Cheshire Colonial where timeless New England ch... |
4 beds | 3 baths | 3,167 sq.ft. |
$619,900 |
Airbnb cash on cash: N/A
|
80 Orleton CourtCheshire, CTBeautifully maintained and truly move-in ready, this 4-bedroom Colonial is tucked away on ... |
4 beds | 3 baths | 2,351 sq.ft. |
$639,900 |
Airbnb cash on cash: N/A
|
840 Westside RoadCheshire, CTInquire immediately-ask your agent to secure this one before it's gone. Welcome to 840 Wes... |
3 beds | 1 baths | 1,491 sq.ft. |
$395,000 |
Airbnb cash on cash: -0.59%
|
73 Southwick Court #73Cheshire, CTBeautiful Manor home at Southwick, a 55+ community offering maintenance-free living and pr... |
2 beds | 3 baths | 1,450 sq.ft. |
$369,900 |
Airbnb cash on cash: -0.83%
|
131 Merwin CircleCheshire, CTCompletely updated Cape Cod-style ranch, custom built with quality craftsmanship throughou... |
3 beds | 3 baths | 2,280 sq.ft. |
$635,000 |
Airbnb cash on cash: -1.07%
|
825 Farmington DriveCheshire, CTBeautifully updated ranch on quiet cul-de-sac in desirable South Cheshire, offering easy o... |
3 beds | 2 baths | 1,688 sq.ft. |
$449,000 |
Airbnb cash on cash: -0.58%
|
200 Chipman DriveCheshire, CT200 Chipman Drive is the home that Cheshire buyers wait for! A move-in ready gem, it offer... |
3 beds | 2 baths | 1,933 sq.ft. |
$550,000 |
Airbnb cash on cash: -0.93%
|
55 Bellamy RoadCheshire, CTWelcome to 55 Bellamy Road in the highly desirable neighborhood of Cheshire. This charming... |
4 beds | 3 baths | 2,344 sq.ft. |
$629,900 |
Airbnb cash on cash: N/A
|
699 Andrea CourtCheshire, CTPerfectly maintained and beautifully appointed Colonial set at the end of a cul-de-sac in ... |
4 beds | 4 baths | 4,154 sq.ft. |
$949,900 |
Airbnb cash on cash: N/A
|
27 S Pond CircleCheshire, CTWelcome to this classic Colonial located in the highly desirable South Pond subdivision, o... |
4 beds | 3 baths | 2,880 sq.ft. |
$675,000 |
Airbnb cash on cash: N/A
|
1274 Cheshire StreetCheshire, CTWelcome to this stunning and immaculately maintained 4-bedroom, 2.5-bathroom colonial, per... |
4 beds | 3 baths | 3,068 sq.ft. |
$699,900 |
Airbnb cash on cash: N/A
|
Real Estate investment in Cheshire, CT
There are 21 properties for sale in the city of Cheshire . The median list price in Cheshire is $629,900 and the average price per square foot is $264. In May 2026, the average monthly cash on cash return in Cheshire is 4.00%. The average monthly rental income in Cheshire is $3,984.