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 |
|---|---|---|---|
309 N Winchester StreetWinchester, INBrand new build nestled in the heart of Geneva. This home features 3 bedrooms and 2 full b... |
3 beds | 2 baths | 1,648 sq.ft. |
$264,927 |
Airbnb cash on cash: N/A
|
326 S Meridian StreetWinchester, INWelcome to this spacious 2-bedroom, 2-bathroom home in the heart of Winchester! Bursting w... |
2 beds | 2 baths | 1,764 sq.ft. |
$149,000 |
Airbnb cash on cash: N/A
|
627 S Main StreetWinchester, INThis beautifully remodeled 2-bedroom, 1-bathroom home offers a perfect blend of classic ch... |
2 beds | 1 baths | 1,636 sq.ft. |
$149,900 |
Airbnb cash on cash: N/A
|
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. |
$184,900 |
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 | 1,568 sq.ft. |
$395,000 |
Airbnb cash on cash: N/A
|
176 Sunset DriveWinchester, INNewly updated 2 bed, 2 bath condo in desirable Summers Pointe! This charming unit offers a... |
2 beds | 2 baths | 1,220 sq.ft. |
$194,900 |
Airbnb cash on cash: N/A
|
1446 Harbours Woodland CourtWinchester, INTake a look at this beautiful home nestled in a serene neighborhood just outside of Winche... |
3 beds | 1 baths | 1,704 sq.ft. |
$158,000 |
Airbnb cash on cash: N/A
|
601 W Franklin StreetWinchester, INWelcome to this inviting 3-bedroom, 2.5-bathroom home that offers comfort, character, and ... |
3 beds | 3 baths | 2,527 sq.ft. |
$259,900 |
Airbnb cash on cash: N/A
|
316 E Franklin StreetWinchester, INWelcome to this charming 3-4 bedroom, 2 full bathroom home in the heart of Winchester! Bur... |
3 beds | 2 baths | 2,291 sq.ft. |
$205,000 |
Airbnb cash on cash: N/A
|
310 N Winchester StreetWinchester, INAuction held onsite Wednesday, September 24th, 2025, 6:00 PM Eastern | Open Houses Monday,... |
2 beds | 2 baths | 1,036 sq.ft. |
$131,900 |
Airbnb cash on cash: N/A
|
1392 E Washington StreetWinchester, INWelcome to this charming and maintained 3 bedroom, 2 bathroom home offering 1,548 square f... |
3 beds | 2 baths | 1,548 sq.ft. |
$178,000 |
Airbnb cash on cash: N/A
|
3224 E Union City PikeWinchester, INSet on 2 peaceful acres in rural Winchester, this 3-bedroom, 1-bath home offers the perfec... |
3 beds | 1 baths | 1,310 sq.ft. |
$184,900 |
Airbnb cash on cash: N/A
|
1492 S Old Hwy 27Winchester, INThis 3-bedroom, 1.5-bath home features custom woodwork throughout and a beautifully crafte... |
3 beds | 2 baths | 1,392 sq.ft. |
$224,900 |
Airbnb cash on cash: N/A
|
1430 E Union City PikeWinchester, INWelcome to this stunning mid-century ranch, offering the perfect blend of charm, space, an... |
3 beds | 2 baths | 2,090 sq.ft. |
$307,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Winchester, IN
There are 14 properties for sale in the city of Winchester . The median list price in Winchester is $181,450 and the average price per square foot is $106. In September 2025, the average monthly cash on cash return in Winchester is 10.00%. The average monthly rental income in Winchester is $1,994.