Real Estate Investment Properties for Sale in Windham, CT
Looking for investment property in Windham, CT with high ROI ?
Explore a variety of short-term homes & houses in Windham, CT. Invest wisely with VRBO & Windham, 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 Windham, CT
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
4 Jerusalem RoadWindham, CTWelcome to this Classic Cape styled home in Windham, CT-where timeless charm meets everyda... |
3 beds | 2 baths | 1,938 sq.ft. |
$399,900 |
Airbnb cash on cash: N/A
|
359 Plains RoadWindham, CTWelcome to this charming and spacious 3-bedroom, 2-bath Colonial nestled in a peaceful Win... |
3 beds | 2 baths | 1,900 sq.ft. |
$289,000 |
Airbnb cash on cash: N/A
|
337 South Windham RoadWindham, CTThis charming four-bedroom, two-and-a-half-bathroom home offers 2,905 square feet of comfo... |
4 beds | 3 baths | 2,905 sq.ft. |
$469,000 |
Airbnb cash on cash: N/A
|
59 Lynwood DriveWindham, CTWelcome to 59 Linwood Drive, nestled in a charming Windham neighborhood and offering both ... |
3 beds | 1 baths | 1,274 sq.ft. |
$262,000 |
Airbnb cash on cash: N/A
|
84 Machine Shop Hill RoadWindham, CTTake a look at this large ranch loaded with all the right features for a great price. Ther... |
2 beds | 2 baths | 2,396 sq.ft. |
$229,900 |
Airbnb cash on cash: N/A
|
29 Kathleen Drive #APT 5EWindham, CTStep inside this immaculate townhouse-style condo and immediately feel the care and attent... |
2 beds | 2 baths | 998 sq.ft. |
$199,500 |
Airbnb cash on cash: N/A
|
231 Back RoadWindham, CTThe fraise, "They don't make'em like this anymore" comes to mind as you walk into this cla... |
3 beds | 2 baths | 2,144 sq.ft. |
$329,999 |
Airbnb cash on cash: N/A
|
295 Jackson StreetWindham, CTSay Happy Centennial to 295 Jackson St! Being lovingly cared for by current owners for 22 ... |
6 beds | 2 baths | 2,576 sq.ft. |
$329,900 |
Airbnb cash on cash: N/A
|
205 Ballamahack RoadWindham, CTOne of A kind 2 family set out in the Country on 1.05 acre! Each side has hardwood floors ... |
4 beds | 3 baths | 1,960 sq.ft. |
$299,900 |
Airbnb cash on cash: N/A
|
162 Scotland RoadWindham, CTOH Sunday 12/06. Highest & Best by 12/13! 2.5 Acres with a beautiful updated... |
3 beds | 2 baths | 1,401 sq.ft. |
$299,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Windham, CT
There are 12 properties for sale in the city of Windham . The median list price in Windham is $329,900 and the average price per square foot is $155. In December 2025, the average monthly cash on cash return in Windham is 7.00%. The average monthly rental income in Windham is $3,191.