Real Estate Investment Properties for Sale in Middlebury, IN
Looking for investment property in Middlebury, IN with high ROI ?
Explore a variety of short-term homes & houses in Middlebury, IN. Invest wisely with VRBO & Middlebury, 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 Middlebury, IN
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
735 Oakleaf DriveMiddlebury, INNew Construction in the beautiful community of Parkrose, featuring the stunning Beacon Mod... |
3 beds | 2 baths | 1,414 sq.ft. |
$307,990 |
Airbnb cash on cash: 0.39%
|
767 Oakleaf DriveMiddlebury, INNew construction by Fischer Homes in the beautiful Parkrose community, featuring the stunn... |
4 beds | 3 baths | 1,842 sq.ft. |
$324,990 |
Airbnb cash on cash: 1.92%
|
622 Bristol AvenueMiddlebury, INA stone bridge and layered landscaping set the tone for this private 5.8-acre estate near ... |
5 beds | 9 baths | 8,414 sq.ft. |
$1,970,000 |
Airbnb cash on cash: N/A
|
510 Crystal Valley DriveMiddlebury, INNestled on just under 2 acres, this unique property offers privacy in town â you wonât... |
3 beds | 3 baths | 2,552 sq.ft. |
$390,000 |
Airbnb cash on cash: -0.01%
|
52478 County Road 39Middlebury, IN*** OPEN HOUSE SATURDAY MARCH 28TH 1-3PM *** Tucked away on nearly 10 acres in Middlebury,... |
5 beds | 4 baths | 3,038 sq.ft. |
$1,199,900 |
Airbnb cash on cash: N/A
|
1116 Erin CourtMiddlebury, INMiddlebury living at it's finest! This gorgeous brick home features 3 bedrooms and 3.5 bat... |
3 beds | 4 baths | 3,729 sq.ft. |
$575,000 |
Airbnb cash on cash: -0.71%
|
12225 County Road 4Middlebury, INThe large 4 bedroom 2 bath home nicely situated on 3 partially wooded acres was built in 2... |
4 beds | 2 baths | 4,656 sq.ft. |
$590,000 |
Airbnb cash on cash: 0.24%
|
10070 Butternut DriveMiddlebury, INLake Life is calling with this custom built 5 bed 4.5 bath home on over an acre of serene ... |
5 beds | 5 baths | 5,997 sq.ft. |
$675,000 |
Airbnb cash on cash: N/A
|
54953 Moonfish CourtMiddlebury, INSpacious two-story home in Winding River Estates. Main level den off the kitchen. The kitc... |
4 beds | 3 baths | 1,645 sq.ft. |
$364,900 |
Airbnb cash on cash: 1.62%
|
10152 County Road 2Middlebury, INPHONE BID AUCTION! Open Houses 3/12, 3/19, 3/26 & 4/2 from 3-5 PM | Phone Bid Auction Ends... |
2 beds | 1 baths | 1,424 sq.ft. |
$225,000 |
Airbnb cash on cash: 0.28%
|
13698 County Road 8 Lot 2 #2Middlebury, INAuction! The price listed is the starting bid, not the buy it now price. Welcome to quiet ... |
1 beds | 2 baths | 1,602 sq.ft. |
$400,000 |
Airbnb cash on cash: -1.19%
|
54230 County Rd 8Middlebury, INOpen House: Saturday, April 4th from 2:00â4:00 PM. Situated on 1.21 acres along the Litt... |
3 beds | 4 baths | 2,875 sq.ft. |
$425,000 |
Airbnb cash on cash: 0.13%
|
209 River Park DriveMiddlebury, INOpen House Sunday March 15th 12-2PM...Maintenance Free Living in Middlebury!!! Well maint... |
2 beds | 2 baths | 1,675 sq.ft. |
$339,900 |
Airbnb cash on cash: -2.12%
|
610 Claudia LaneMiddlebury, INThis well-maintained bi-level home offers the perfect blend of comfort, style, and functio... |
3 beds | 2 baths | 2,064 sq.ft. |
$319,500 |
Airbnb cash on cash: 0.72%
|
Real Estate investment in Middlebury, IN
There are 14 properties for sale in the city of Middlebury . The median list price in Middlebury is $649,900 and the average price per square foot is $271. In April 2026, the average monthly cash on cash return in Middlebury is 6.00%. The average monthly rental income in Middlebury is $2,690.