Real Estate Investment Properties for Sale in Winchester, IN
Looking for investment property in Winchester, IN with high ROI ?
Explore a variety of short-term homes & houses in Winchester, IN. Invest wisely with VRBO & Winchester, IN 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, IN
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
170 Sunset DrWinchester, INThis thoughtfully designed 2 bedroom, 2 bathroom condo offers a spacious living room that ... |
2 beds | 2 baths | 1,220 sq.ft. |
$179,900 |
Airbnb cash on cash: N/A
|
1041 S Huntsville RdWinchester, INBRAND NEW 3-bedroom, 2.5-bath home in Winchester with top-tier construction throughout. Th... |
3 beds | 2 baths | 1,977 sq.ft. |
$359,900 |
Airbnb cash on cash: N/A
|
603 Stone StWinchester, INCome see this beautifully renovated 3 bedroom, 2 full bath home in Winchester! This home o... |
3 beds | 2 baths | 1,648 sq.ft. |
$164,900 |
Airbnb cash on cash: N/A
|
625 E Beech StWinchester, INCharming 2 bedroom, 1 bath home featuring a welcoming covered front deck and a back deck. ... |
2 beds | 1 baths | 1,014 sq.ft. |
$118,900 |
Airbnb cash on cash: N/A
|
122 Sunset DrWinchester, INThis thoughtfully designed 2 bedroom, 2 bathroom condo offers a spacious living room that ... |
2 beds | 2 baths | 1,220 sq.ft. |
$184,900 |
Airbnb cash on cash: N/A
|
405 W Washington StreetWinchester, INThis beautifully maintained 2022-built attached home offers an open-concept complete with... |
2 beds | 2 baths | 1,600 sq.ft. |
$264,900 |
Airbnb cash on cash: N/A
|
2588 N Old Hwy 27Winchester, IN3-bedroom, 1-bath home featuring numerous recent updates, including fresh paint, new floor... |
3 beds | 1 baths | 1,257 sq.ft. |
$164,900 |
Airbnb cash on cash: N/A
|
684 E 225 NWinchester, INDiscover this 3 bedroom, 1 bathroom farmhouse offering 1,848 square feet of living space,... |
3 beds | 1 baths | 1,848 sq.ft. |
$212,000 |
Airbnb cash on cash: N/A
|
810 S Elm BoulevardWinchester, INWelcome home to this well-maintained 3-bedroom, 1.5-bath property offering comfort, space,... |
3 beds | 2 baths | 1,360 sq.ft. |
$164,900 |
Airbnb cash on cash: N/A
|
Real Estate investment in Winchester, IN
There are 20 properties for sale in the city of Winchester . The median list price in Winchester is $402,500 and the average price per square foot is $189. In February 2026, the average monthly cash on cash return in Winchester is 11.00%. The average monthly rental income in Winchester is $1,932.