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 DriveWinchester, 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 RoadWinchester, INBRAND NEW 3-bedroom, 2.5-bath home in Winchester with top-tier construction throughout. Th... |
3 beds | 3 baths | 1,977 sq.ft. |
$374,900 |
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
|
742 Huntsville RoadWinchester, INWelcome to this beautifully updated 3-bedroom, 2-bath home in Winchester! This move-in rea... |
3 beds | 2 baths | 1,300 sq.ft. |
$219,900 |
Airbnb cash on cash: N/A
|
625 E Beech StreetWinchester, INCharming 2 bedroom, 1 bath home featuring a welcoming covered front deck and a back deck. ... |
2 beds | 1 baths | 1,014 sq.ft. |
$119,900 |
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. |
$220,000 |
Airbnb cash on cash: N/A
|
122 Sunset DriveWinchester, 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
|
424 E South StreetWinchester, INNicely updated 2 bedroom, 1 bathroom home in Winchester. This property offers a comfortabl... |
2 beds | 1 baths | 1,120 sq.ft. |
$139,900 |
Airbnb cash on cash: N/A
|
317 E North StreetWinchester, INCheck out this home in Winchester! This newly remodeled home features 4 bedrooms and 3 bat... |
4 beds | 3 baths | 1,810 sq.ft. |
$199,900 |
Airbnb cash on cash: N/A
|
712 Wedgewood DriveWinchester, INWelcome to this fully remodeled 3 bedroom, 1 bathroom home, updated from top to bottom and... |
3 beds | 1 baths | 1,026 sq.ft. |
$189,900 |
Airbnb cash on cash: N/A
|
Real Estate investment in Winchester, IN
There are 10 properties for sale in the city of Winchester . The median list price in Winchester is $182,400 and the average price per square foot is $128. In December 2025, the average monthly cash on cash return in Winchester is 10.00%. The average monthly rental income in Winchester is $1,916.