Real Estate Investment Properties for Sale in Winchester, CT
Looking for investment property in Winchester, CT with high ROI ?
Explore a variety of short-term homes & houses in Winchester, CT. Invest wisely with VRBO & Winchester, 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 Winchester, CT
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
100 Norfolk RoadWinchester, CT3.7-acre property offering a 4-bedroom, 2-bath Cape with plenty of room and flexibility. F... |
4 beds | 2 baths | 2,914 sq.ft. |
$350,000 |
Airbnb cash on cash: 4.07%
|
19 Walnut StreetWinchester, CTOffering over 2,800 square feet of living space and 11 rooms, this spacious home in Winste... |
4 beds | 3 baths | 2,868 sq.ft. |
$285,000 |
Airbnb cash on cash: 5.53%
|
132 E Lake StreetWinchester, CTWelcome to East Lake Street at Highland Lake, where privacy, comfort, and lake living come... |
3 beds | 2 baths | 1,820 sq.ft. |
$365,000 |
Airbnb cash on cash: 2.34%
|
48 Center StreetWinchester, CTInvestment Opportunity! Well-maintained two-family house offering the ideal combination of... |
4 beds | 3 baths | 2,257 sq.ft. |
$325,000 |
Airbnb cash on cash: 5.21%
|
120 Moore AvenueWinchester, CTSituated on a side street just outside the town, this contemporary 3-bedroom residence exu... |
3 beds | 2 baths | 1,952 sq.ft. |
$399,000 |
Airbnb cash on cash: 1.65%
|
150 E Lake StreetWinchester, CTEnjoy lake living with this inviting 3 bedroom, two and a half bath home located directly ... |
3 beds | 3 baths | 1,659 sq.ft. |
$449,000 |
Airbnb cash on cash: 1.36%
|
18 Pratt StreetWinchester, CTGreat Investment Opportunity! Well-maintained two-family home with both units currently re... |
5 beds | 2 baths | 2,016 sq.ft. |
$299,900 |
Airbnb cash on cash: N/A
|
77 Hubbard StreetWinchester, CTDiscover this versatile two-family residence offering a blend of modern updates and timele... |
4 beds | 2 baths | 2,699 sq.ft. |
$359,900 |
Airbnb cash on cash: 4.31%
|
237 Wallens Hill RoadWinchester, CTWelcome to 237 Wallens Hill Road, where comfort, quality, and exceptional entertaining spa... |
4 beds | 3 baths | 2,628 sq.ft. |
$579,900 |
Airbnb cash on cash: 1.64%
|
70 Walnut StreetWinchester, CTStep back in time and experience the timeless elegance of this spacious 2,722 sq. ft. Vict... |
4 beds | 2 baths | 2,722 sq.ft. |
$305,000 |
Airbnb cash on cash: 4.71%
|
122 Standard AvenueWinchester, CTWelcome home to this well-maintained 4-bedroom Colonial tucked away on a quiet dead-end st... |
4 beds | 2 baths | 1,944 sq.ft. |
$379,900 |
Airbnb cash on cash: 3.72%
|
50 Overlook RoadWinchester, CTLovingly maintained by the same family since it was built in 1949, this 3-bedroom Colonial... |
3 beds | 1 baths | 1,488 sq.ft. |
$339,900 |
Airbnb cash on cash: 2.58%
|
99 High StreetWinchester, CT99 High St, Winsted, CT 06098 is a multi family residential property. The Building was bui... |
14 beds | 12 baths | 3,012 sq.ft. |
$575,000 |
Airbnb cash on cash: N/A
|
218 Oak StreetWinchester, CTBring your design ideas to this classic shingle-sided home. With a fully functional interi... |
3 beds | 1 baths | 1,155 sq.ft. |
$225,000 |
Airbnb cash on cash: 5.12%
|
240 Florence StreetWinchester, CTMake yourself at home while exploring the possibilities this property has to offer. Fresh ... |
2 beds | 1 baths | 936 sq.ft. |
$264,900 |
Airbnb cash on cash: 1.58%
|
Real Estate investment in Winchester, CT
There are 25 properties for sale in the city of Winchester . The median list price in Winchester is $414,900 and the average price per square foot is $190. In November 2026, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $2,234.