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. |
$318,990 |
Airbnb cash on cash: 1.47%
|
622 Bristol AveMiddlebury, INOpen House Scheduled for August 23 1-3pm! A stone bridge and layered landscaping set the ... |
5 beds | 5 baths | 8,414 sq.ft. |
$1,970,000 |
Airbnb cash on cash: N/A
|
525 S Main StMiddlebury, INON THE PUMPKIN VINE.....This nearly one acre lot in town features a 4 bedroom, 2 bath home... |
4 beds | 2 baths | 1,972 sq.ft. |
$339,000 |
Airbnb cash on cash: 3.76%
|
209 River Park DrMiddlebury, INMaintenance Free Living in Middlebury!!! Well maintained condo in the Villas of River Par... |
2 beds | 2 baths | 1,675 sq.ft. |
$349,900 |
Airbnb cash on cash: -1.19%
|
510 Crystal Valley DrMiddlebury, 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: 0.94%
|
52478 County Road 39Middlebury, INTucked away on nearly 10 acres in Middlebury, this 2022 custom stick-built home offers a p... |
5 beds | 2 baths | 3,038 sq.ft. |
$1,199,900 |
Airbnb cash on cash: N/A
|
510 Caprice DrMiddlebury, INWelcome home to this beautifully updated quad-level home in the sought-after Middlebury Sc... |
3 beds | 2 baths | 1,618 sq.ft. |
$334,900 |
Airbnb cash on cash: 1.57%
|
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. |
$585,000 |
Airbnb cash on cash: -0.08%
|
12225 County Road 4Middlebury, INAUCTION!! This 3 acre property is selling at Phone Bid auction with bidding to end on Feb ... |
4 beds | 2 baths | 4,656 sq.ft. |
$525,000 |
Airbnb cash on cash: 1.54%
|
312 Bristol AveMiddlebury, IN312 Bristol Ave, Middlebury, IN 46540 | Single Family Residential |
4 beds | 2 baths | 3,640 sq.ft. |
$444,900 |
Airbnb cash on cash: 2.39%
|
56085 CR 33Middlebury, IN56085 CR 33, Middlebury, IN 46540 | Single Family Residential |
4 beds | 3 baths | 2,856 sq.ft. |
$739,500 |
Airbnb cash on cash: 0.71%
|
53982 Midnight StarMiddlebury, IN53982 Midnight Star, Middlebury, IN 46540 | Other |
N/A beds | N/A baths | N/A |
$90,000 |
Airbnb cash on cash: 2.39%
|
14483 County Road 8Middlebury, IN14483 County Road 8, Middlebury, IN 46540 | Single Family Residential |
3 beds | 2 baths | 1,568 sq.ft. |
$369,900 |
Airbnb cash on cash: 1.18%
|
7505 N 1200 RdMiddlebury, IN
|
3 beds | 2 baths | 1,248 sq.ft. |
$190,000 |
Airbnb cash on cash: 3.96%
|
824 Spring Meadow Farm DriveMiddlebury, INWelcome to Middlebury featuring this executive home on Meadow Valley Golf Course with the ... |
5 beds | 6 baths | 4,384 sq.ft. |
$549,900 |
Airbnb cash on cash: N/A
|
200 E Berry StreetMiddlebury, INCharming Downtown Middlebury Living! Nestled on a desirable corner lot in the heart of dow... |
3 beds | 2 baths | 2,246 sq.ft. |
$220,000 |
Airbnb cash on cash: 3.17%
|
Real Estate investment in Middlebury, IN
There are 16 properties for sale in the city of Middlebury . The median list price in Middlebury is $659,900 and the average price per square foot is $260. In February 2026, the average monthly cash on cash return in Middlebury is 5.00%. The average monthly rental income in Middlebury is $2,626.