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: N/A
|
14188 CR 28Middlebury, INGreat, Updated Property now for sale! Situated on 6 acres, this 3-bedroom, 2-bathroom prop... |
3 beds | 2 baths | 2,300 sq.ft. |
$675,000 |
Airbnb cash on cash: N/A
|
101 Hemsberd StMiddlebury, INAll new Carpeting and freshly painted. It has a Main Level Master Suite and an additional ... |
3 beds | 3 baths | 1,788 sq.ft. |
$309,900 |
Airbnb cash on cash: N/A
|
205 Greenfield DrMiddlebury, INTop Quality all brick executive Middlebury home built by Town and Country Builders with ov... |
6 beds | 4 baths | 6,412 sq.ft. |
$1,200,000 |
Airbnb cash on cash: N/A
|
928 S Main StMiddlebury, INVery well kept 3 BR Ranch Style home on the south side of Middlebury that sits on a genero... |
3 beds | 2 baths | 2,116 sq.ft. |
$289,900 |
Airbnb cash on cash: N/A
|
13889 Adirondack CtMiddlebury, INGorgeous home in Middlebury Schools! Custom built home. Extra deep garage, finished baseme... |
5 beds | 3 baths | 4,473 sq.ft. |
$789,900 |
Airbnb cash on cash: N/A
|
12825 Sunfish DrMiddlebury, INBeautiful ranch home located in Middlebury, Indiana's Winding River subdivision. The neigh... |
3 beds | 2 baths | 1,450 sq.ft. |
$345,000 |
Airbnb cash on cash: N/A
|
115 Greenfield DrMiddlebury, INSprawling ranch in the highly sought-after Highland Hills neighborhood in Middlebury Schoo... |
3 beds | 2 baths | 3,304 sq.ft. |
$434,900 |
Airbnb cash on cash: N/A
|
12853 King Fish CtMiddlebury, IN***BACK ON MARKET AT NO FAULT OF SELLER *** Step into this beautifully refreshed home! The... |
3 beds | 2 baths | 1,970 sq.ft. |
$349,000 |
Airbnb cash on cash: N/A
|
606 Claudia LnMiddlebury, INGreat move-in ready home in Westlake Estates conveniently located near schools and US20! T... |
3 beds | 2 baths | 1,176 sq.ft. |
$279,900 |
Airbnb cash on cash: N/A
|
53339 State Road 13Middlebury, INTake a look at his amazing Barndo located just outside of Middlebury on 6+ rolling/wooded ... |
4 beds | 3 baths | 3,528 sq.ft. |
$899,000 |
Airbnb cash on cash: N/A
|
10281 County Road 4Middlebury, INPeace is all you will think of at this home. Nestled on 1 acre in the desirable Middlebury... |
3 beds | 1 baths | 1,990 sq.ft. |
$369,500 |
Airbnb cash on cash: N/A
|
1116 Erin CtMiddlebury, INMiddlebury living at it's finest! This gorgeous brick home features 3 bedrooms and 3.5 bat... |
4 beds | 3 baths | 3,729 sq.ft. |
$474,900 |
Airbnb cash on cash: N/A
|
312 Bristol AveMiddlebury, IN312 Bristol Ave, Middlebury, IN 46540 | Single Family Residential |
4 beds | 2 baths | 3,640 sq.ft. |
$439,900 |
Airbnb cash on cash: N/A
|
53982 Midnight StarMiddlebury, IN53982 Midnight Star, Middlebury, IN 46540 | Other |
N/A beds | N/A baths | N/A |
$90,000 |
Airbnb cash on cash: N/A
|
11955 W 710 NMiddlebury, IN11955 W 710 N, Middlebury, IN 46540 | Single Family Residential |
3 beds | 1 baths | 1,424 sq.ft. |
$280,000 |
Airbnb cash on cash: N/A
|
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: N/A
|
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
|
12330 County Road 4Middlebury, IN12330 County Road 4, Middlebury, IN 46540 | Single Family Residential |
5 beds | 3 baths | 4,832 sq.ft. |
$580,000 |
Airbnb cash on cash: N/A
|
57051 County Road 33Middlebury, INHere's an opportunity to own a versatile country property featuring two homes, a barn, and... |
4 beds | 2 baths | 3,052 sq.ft. |
$695,000 |
Airbnb cash on cash: N/A
|
13120 Bear Creek CtMiddlebury, IN13120 Bear Creek Ct, Middlebury, IN 46540 | Single Family Residential |
5 beds | 3 baths | 2,584 sq.ft. |
$549,900 |
Airbnb cash on cash: N/A
|
54725 County Road 33Middlebury, IN54725 County Road 33, Middlebury, IN 46540 | Single Family Residential |
5 beds | 4 baths | 6,370 sq.ft. |
$1,390,000 |
Airbnb cash on cash: N/A
|
411 S Main StMiddlebury, IN411 S Main St, Middlebury, IN 46540 | Single Family Residential |
4 beds | 1 baths | 1,656 sq.ft. |
$209,900 |
Airbnb cash on cash: N/A
|
313 Bristol AveMiddlebury, IN313 Bristol Ave, Middlebury, IN 46540 | Single Family Residential |
4 beds | 1 baths | 2,256 sq.ft. |
$299,900 |
Airbnb cash on cash: N/A
|
13283 Cedar Creek DrMiddlebury, IN13283 Cedar Creek Dr, Middlebury, IN 46540 | Single Family Residential |
5 beds | 4 baths | 4,908 sq.ft. |
$800,000 |
Airbnb cash on cash: N/A
|
111 River Park DrMiddlebury, IN111 River Park Dr, Middlebury, IN 46540 | Condo/Coop |
2 beds | 3 baths | 2,485 sq.ft. |
$354,900 |
Airbnb cash on cash: N/A
|
11975 W State Road 120 RdMiddlebury, IN11975 W W State Road 120 Rd, Middlebury, IN 46540 | Single Family Residential |
3 beds | 2 baths | 2,240 sq.ft. |
$345,000 |
Airbnb cash on cash: N/A
|
51134 County Road 37Middlebury, IN51134 County Road 37, Middlebury, IN 46540 | Single Family Residential |
4 beds | 2 baths | 1,566 sq.ft. |
$450,000 |
Airbnb cash on cash: N/A
|
209 Bristol AveMiddlebury, IN209 Bristol Ave, Middlebury, IN 46540 | Single Family Residential |
4 beds | 2 baths | 2,055 sq.ft. |
$299,900 |
Airbnb cash on cash: N/A
|
53660 Forest Lakes DrMiddlebury, IN53660 Forest Lakes Dr, Middlebury, IN 46540 | Single Family Residential |
5 beds | 3 baths | 3,333 sq.ft. |
$715,000 |
Airbnb cash on cash: N/A
|
54895 Moonfish CtMiddlebury, IN54895 Moonfish Ct, Middlebury, IN 46540 | Single Family Residential |
4 beds | 2 baths | 1,908 sq.ft. |
$349,000 |
Airbnb cash on cash: N/A
|
110 N Scott StMiddlebury, IN110 N Scott St, Middlebury, IN 46540 | Single Family Residential |
2 beds | 2 baths | 3,848 sq.ft. |
$515,000 |
Airbnb cash on cash: N/A
|
12330 County Road 4 StMiddlebury, IN12330 County Road 4 St, Middlebury, IN 46540 | Single Family Residential |
5 beds | 4 baths | 4,216 sq.ft. |
$575,000 |
Airbnb cash on cash: N/A
|
211 Greenfield DrMiddlebury, IN211 Greenfield Dr, Middlebury, IN 46540 | Single Family Residential |
4 beds | 3 baths | 3,841 sq.ft. |
$649,900 |
Airbnb cash on cash: N/A
|
217 Greenfield DrMiddlebury, IN217 Greenfield Dr, Middlebury, IN 46540 | Single Family Residential |
5 beds | 3 baths | 3,582 sq.ft. |
$699,000 |
Airbnb cash on cash: N/A
|
14340 County Road 12Middlebury, IN14340 County Road 12, Middlebury, IN 46540 | Single Family Residential |
3 beds | 1 baths | 1,791 sq.ft. |
$325,000 |
Airbnb cash on cash: N/A
|
1006 Hidden Meadow LnMiddlebury, IN1006 Hidden Meadow Ln, Middlebury, IN 46540 | Single Family Residential |
3 beds | 3 baths | 2,864 sq.ft. |
$420,000 |
Airbnb cash on cash: N/A
|
55750 County Road 33Middlebury, IN55750 County Road 33, Middlebury, IN 46540 | Single Family Residential |
4 beds | 4 baths | 3,696 sq.ft. |
$700,000 |
Airbnb cash on cash: N/A
|
12028 CR 18Middlebury, IN12028 CR 18, Middlebury, IN 46540 | Single Family Residential |
3 beds | 2 baths | 1,594 sq.ft. |
$400,000 |
Airbnb cash on cash: N/A
|
55755 Little Creek LnMiddlebury, IN55755 Little Creek Ln, Middlebury, IN 46540 | Single Family Residential |
4 beds | 3 baths | 3,575 sq.ft. |
$649,900 |
Airbnb cash on cash: N/A
|
Real Estate investment in Middlebury, IN
There are 65 properties for sale in the city of Middlebury . The median list price in Middlebury is $327,254 and the average price per square foot is $129. In October 2026, the average monthly cash on cash return in Middlebury is 5.00%. The average monthly rental income in Middlebury is $2,756.