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: 1.84%
|
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%
|
200 E Berry StMiddlebury, INCharming Downtown Middlebury Living! Nestled on a desirable corner lot in the heart of dow... |
4 beds | 2 baths | 2,337 sq.ft. |
$324,900 |
Airbnb cash on cash: 2.27%
|
1116 Erin CtMiddlebury, INMiddlebury living at it's finest! This gorgeous brick home features 3 bedrooms and 3.5 bat... |
3 beds | 3 baths | 3,729 sq.ft. |
$549,000 |
Airbnb cash on cash: 0.01%
|
53982 Midnight StarMiddlebury, IN53982 Midnight Star, Middlebury, IN 46540 | Other |
N/A beds | N/A baths | N/A |
$90,000 |
Airbnb cash on cash: 4.29%
|
14483 County Road 8Middlebury, IN14483 County Road 8, Middlebury, IN 46540 | Single Family Residential |
3 beds | 2 baths | 1,568 sq.ft. |
$349,900 |
Airbnb cash on cash: 1.4%
|
7505 N 1200 RdMiddlebury, IN
|
3 beds | 2 baths | 1,248 sq.ft. |
$190,000 |
Airbnb cash on cash: 4.06%
|
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: -0.02%
|
12514 Bonnie LnMiddlebury, IN12514 Bonnie Ln, Middlebury, IN 46540 | Manufactured Home |
3 beds | 2 baths | 1,782 sq.ft. |
$169,900 |
Airbnb cash on cash: 4.4%
|
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: 1.04%
|
55902 Little Creek Ln #70Middlebury, IN55902 Little Creek Ln #70, Middlebury, IN 46540 | Other |
N/A beds | N/A baths | N/A |
$89,900 |
Airbnb cash on cash: 4.13%
|
242 River Park DrMiddlebury, INA rare opportunity to experience the privacy of a free-standing home with the ease of vill... |
3 beds | 3 baths | 2,197 sq.ft. |
$459,900 |
Airbnb cash on cash: -0.01%
|
54420 County Road 33 RdMiddlebury, IN54420 County Road 33 Rd, Middlebury, IN 46540 | Single Family Residential |
6 beds | 6 baths | 12,367 sq.ft. |
$4,999,900 |
Airbnb cash on cash: N/A
|
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: 0.94%
|
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: 2.15%
|
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%
|
Real Estate investment in Middlebury, IN
There are 21 properties for sale in the city of Middlebury . The median list price in Middlebury is $599,900 and the average price per square foot is $247. In May 2026, the average monthly cash on cash return in Middlebury is 6.00%. The average monthly rental income in Middlebury is $2,689.