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 |
|---|---|---|---|
622 Bristol AvenueMiddlebury, INOpen House Scheduled for August 23 1-3pm! A stone bridge and layered landscaping set the ... |
5 beds | 9 baths | 8,414 sq.ft. |
$1,970,000 |
Airbnb cash on cash: N/A
|
608 Fieldstone LaneMiddlebury, INAdorable Ranch located in Northridge School District- situated on a cul-de-sac--This home ... |
3 beds | 2 baths | 2,252 sq.ft. |
$289,900 |
Airbnb cash on cash: 2.7%
|
750 Oakleaf DriveMiddlebury, INNew Construction by Fischer Homes in the beautiful Parkrose community with the Jensen plan... |
4 beds | 3 baths | 2,800 sq.ft. |
$369,990 |
Airbnb cash on cash: N/A
|
792 Oakleaf DriveMiddlebury, INTrendy new Fairfax American Classic plan by Fischer Homes in beautiful Parkrose featuring ... |
4 beds | 3 baths | 2,491 sq.ft. |
$369,990 |
Airbnb cash on cash: N/A
|
13909 Shavano Peak DriveMiddlebury, INStunning ... New Construction! The property is still in the early stages, giving you the p... |
3 beds | 3 baths | 2,569 sq.ft. |
$689,760 |
Airbnb cash on cash: 0.86%
|
11306 Fishers PondMiddlebury, INThis stunning home is truly inspired by The Farm as this farm-style gem is straight from a... |
5 beds | 4 baths | 4,326 sq.ft. |
$974,900 |
Airbnb cash on cash: N/A
|
51561 E County Line RoadMiddlebury, INLooking for a new construction with an incredible view? Look no further! This 3 bedroom,... |
3 beds | 2 baths | 1,708 sq.ft. |
$329,900 |
Airbnb cash on cash: 3.02%
|
735 Oakleaf DriveMiddlebury, INNew Construction in the beautiful community of Parkrose, featuring the stunning Beacon Mod... |
3 beds | 2 baths | 1,414 sq.ft. |
$324,990 |
Airbnb cash on cash: 2.1%
|
611 Claudia LaneMiddlebury, INAcross from Northridge High School! Enjoy the convenience of being just minutes from North... |
4 beds | 3 baths | 2,464 sq.ft. |
$390,000 |
Airbnb cash on cash: N/A
|
10281 County Road 4Middlebury, INPeace is all you will think of at this home. Nestled on nearly 2 acres in the desirable Mi... |
3 beds | 1 baths | 1,990 sq.ft. |
$395,000 |
Airbnb cash on cash: 1.52%
|
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. |
$415,000 |
Airbnb cash on cash: 1.37%
|
52690 Rachael CourtMiddlebury, INNew Construction in Middlebury Schools! Tucked in the back of Sandy Hill at the end of a... |
3 beds | 2 baths | 1,248 sq.ft. |
$324,000 |
Airbnb cash on cash: 2.83%
|
53048 State Road 13Middlebury, INWelcome to your private oasis just minutes from town! This beautifully remodeled home sits... |
3 beds | 2 baths | 2,862 sq.ft. |
$345,000 |
Airbnb cash on cash: 2.2%
|
13149 State Rd 120Middlebury, INWelcome to this private 2-acre retreat in the Middlebury School District! This fully renov... |
4 beds | 2 baths | 2,336 sq.ft. |
$348,500 |
Airbnb cash on cash: N/A
|
52610 County Road 39Middlebury, INWelcome to this exceptional 65-acre property, offering the perfect blend of privacy, natur... |
4 beds | 5 baths | 4,740 sq.ft. |
$2,138,400 |
Airbnb cash on cash: N/A
|
607 Claudia LaneMiddlebury, INWelcome to 607 Claudia Lane, perfectly situated on a spacious double lot in a quiet and de... |
3 beds | 2 baths | 3,223 sq.ft. |
$349,900 |
Airbnb cash on cash: 1.81%
|
Real Estate investment in Middlebury, IN
There are 16 properties for sale in the city of Middlebury . The median list price in Middlebury is $369,990 and the average price per square foot is $125. In October 2025, the average monthly cash on cash return in Middlebury is 6.00%. The average monthly rental income in Middlebury is $2,724.