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 |
|---|---|---|---|
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: 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. |
$299,990 |
Airbnb cash on cash: 1.74%
|
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. |
$535,000 |
Airbnb cash on cash: 0.04%
|
10070 Butternut DriveMiddlebury, INMultiple Offer Notification!!! Highest and Best due by 8pm 4/27/26. Lake Life is calling w... |
5 beds | 5 baths | 5,997 sq.ft. |
$675,000 |
Airbnb cash on cash: N/A
|
10152 County Road 2Middlebury, INThis 2-bedroom, 1-bath single-story home with a loft sits on 3 beautiful rural acres and o... |
2 beds | 1 baths | 1,424 sq.ft. |
$255,000 |
Airbnb cash on cash: -0.27%
|
56408 White Pine RidgeMiddlebury, INThis remarkable walk-out Ranch showcases 4,962 sq ft of beautifully designed living space.... |
4 beds | 4 baths | 3,722 sq.ft. |
$789,900 |
Airbnb cash on cash: 0.27%
|
53242 County Road 43Middlebury, INSpacious 4-bedroom, 2-bath quad-level home offering over 2,100 square feet of comfortable ... |
4 beds | 2 baths | 2,107 sq.ft. |
$369,900 |
Airbnb cash on cash: 2.93%
|
57051 County Road 33Middlebury, INPHONE BID AUCTION ending Tuesday, June 9th at 3PM. The price listed is the starting bid, n... |
4 beds | 2 baths | 3,052 sq.ft. |
$550,000 |
Airbnb cash on cash: 0.63%
|
210 River Park DriveMiddlebury, INThis beautifully appointed villa in the quaint town of Middlebury is where comfort, qualit... |
3 beds | 3 baths | 2,800 sq.ft. |
$429,900 |
Airbnb cash on cash: 0.14%
|
13745 Ranier DriveMiddlebury, INWelcome to this beautifully maintained 4-bedroom, 3-bathroom home located in the highly so... |
4 beds | 3 baths | 3,176 sq.ft. |
$467,000 |
Airbnb cash on cash: 1.77%
|
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: 0.99%
|
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: 1.93%
|
52478 County Road 39Middlebury, INTucked away on nearly 10 acres in Middlebury, this 2022 custom stick-built home offers a p... |
5 beds | 4 baths | 3,038 sq.ft. |
$1,099,900 |
Airbnb cash on cash: N/A
|
12454 Stoney DriveMiddlebury, INMultiple Offers--please submit by 7pm 4/23/26---Well maintained one-story home in Middlebu... |
4 beds | 3 baths | 2,437 sq.ft. |
$325,000 |
Airbnb cash on cash: 3.33%
|
52736 Rachael CourtMiddlebury, INNew Construction in Middlebury Schools! Tucked in the back of Sandy Hill, you'll find th... |
3 beds | 2 baths | 1,634 sq.ft. |
$339,000 |
Airbnb cash on cash: 2.05%
|
242 River Park DriveMiddlebury, IN**OPEN HOUSE May 17th from 1-3PM.** A rare opportunity to experience the privacy of a free... |
3 beds | 3 baths | 2,197 sq.ft. |
$459,900 |
Airbnb cash on cash: -0.01%
|
Real Estate investment in Middlebury, IN
There are 16 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 $274. In May 2026, the average monthly cash on cash return in Middlebury is 5.00%. The average monthly rental income in Middlebury is $2,789.