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. |
$299,990 |
Airbnb cash on cash: 2.45%
|
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: 2.63%
|
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: 0.64%
|
518 Sunset LaneMiddlebury, INOPEN HOUSE SUNDAY 2-4PM!! Welcome to this summer ready home on Sunset Dr. You will love ... |
3 beds | 2 baths | 2,942 sq.ft. |
$385,000 |
Airbnb cash on cash: 1.67%
|
50701 County Road 37Middlebury, INPhone bid auction ending Thursday, July 9th, at 4:00 PM! The price listed is the starting ... |
3 beds | 2 baths | 2,545 sq.ft. |
$325,000 |
Airbnb cash on cash: 2.11%
|
13184 State Road 120Middlebury, INPhone bid auction ending Wednesday, June 24th at 3pm. Price listed is the starting bid, no... |
3 beds | 2 baths | 2,120 sq.ft. |
$475,000 |
Airbnb cash on cash: 1.09%
|
115 Greenfield DriveMiddlebury, INSprawling ranch in the highly sought-after Highland Hills neighborhood in Middlebury Schoo... |
3 beds | 3 baths | 3,304 sq.ft. |
$434,900 |
Airbnb cash on cash: 1.23%
|
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. |
$349,900 |
Airbnb cash on cash: 2.13%
|
53339 State Road 13Middlebury, INTake a look at his amazing Barndo located just outside of Middlebury on 6+ rolling/wooded ... |
4 beds | 4 baths | 3,528 sq.ft. |
$920,000 |
Airbnb cash on cash: -0.02%
|
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. |
$384,500 |
Airbnb cash on cash: 1.61%
|
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: 0.44%
|
53982 Midnight StarMiddlebury, IN53982 Midnight Star, Middlebury, IN 46540 | Other |
N/A beds | N/A baths | N/A |
$90,000 |
Airbnb cash on cash: 9.75%
|
14483 County Road 8Middlebury, IN14483 County Road 8, Middlebury, IN 46540 | Single Family Residential |
3 beds | 2 baths | 1,568 sq.ft. |
$329,900 |
Airbnb cash on cash: 2.24%
|
11955 W 710 NMiddlebury, IN11955 W 710 N, Middlebury, IN 46540 | Single Family Residential |
3 beds | 1 baths | 1,424 sq.ft. |
$420,000 |
Airbnb cash on cash: 1.38%
|
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: 9.6%
|
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. |
$740,000 |
Airbnb cash on cash: -0.04%
|
13120 Bear Creek CtMiddlebury, IN13120 Bear Creek Ct, Middlebury, IN 46540 | Single Family Residential |
5 beds | 3 baths | 2,584 sq.ft. |
$599,900 |
Airbnb cash on cash: N/A
|
609 Westlake DriveMiddlebury, INThis classic 3 Bed 3 Full Baths has everything you need, and more! Every room has been fre... |
3 beds | 3 baths | 2,200 sq.ft. |
$395,000 |
Airbnb cash on cash: 1.84%
|
13912 Shavano Peak DriveMiddlebury, INLooking for something "like new" without the new construction price tag? Here it is! This ... |
4 beds | 2 baths | 2,078 sq.ft. |
$539,000 |
Airbnb cash on cash: 0.99%
|
54725 County Road 33Middlebury, IN54725 County Road 33, Middlebury, IN 46540 | Single Family Residential |
5 beds | 4 baths | 6,370 sq.ft. |
$1,540,000 |
Airbnb cash on cash: N/A
|
54646 State Road 13Middlebury, INCharming 3-bedroom, single-story home in Middlebury offering comfortable living in a conve... |
3 beds | 2 baths | 1,728 sq.ft. |
$349,900 |
Airbnb cash on cash: 2.29%
|
518 Redbud LaneMiddlebury, INYou will appreciate the many updates throughout this beautiful 4-bedroom, 2.5 bath home! E... |
4 beds | 3 baths | 2,254 sq.ft. |
$366,000 |
Airbnb cash on cash: 2.4%
|
509 Morningstar CourtMiddlebury, IN**Open House Saturday, 6/13 11 AM - 1 PM and Sunday, 6/14 11 AM - 1 PM*** Amazing Cape C... |
4 beds | 2 baths | 1,456 sq.ft. |
$259,000 |
Airbnb cash on cash: 4.17%
|
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: 1.5%
|
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: 0.46%
|
12340 County Road 4Middlebury, INThis genuinely remarkable property has a lot to offer. Selling via phone bid auction. List... |
4 beds | 4 baths | 4,138 sq.ft. |
$1,200,000 |
Airbnb cash on cash: -0.4%
|
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. |
$774,900 |
Airbnb cash on cash: 0.13%
|
53242 County Road 43Middlebury, IN**Open House Sunday May 31st from 1-3PM** **Motivated Seller** Spacious 4-bedroom, 2-bat... |
4 beds | 2 baths | 2,107 sq.ft. |
$359,900 |
Airbnb cash on cash: 2.72%
|
54721 State Road 13Middlebury, INAUCTION! This Middlebury property to sell at Live Auction on June 20th at 12:00. The aucti... |
2 beds | 1 baths | 1,001 sq.ft. |
$202,500 |
Airbnb cash on cash: 1.04%
|
55822 Alverstone DriveMiddlebury, INStep into a home where comfort comes naturally. Tucked into the peaceful embrace of The S... |
4 beds | 4 baths | 3,093 sq.ft. |
$499,000 |
Airbnb cash on cash: 1.15%
|
203 Eugene DriveMiddlebury, INMove right into this beautifully updated ranch home that combines modern comfort with a pe... |
3 beds | 3 baths | 3,096 sq.ft. |
$379,900 |
Airbnb cash on cash: 1.79%
|
329 Bristol AvenueMiddlebury, INGreat 3 Bedroom 2 Bath Home close to downtown Middlebury. |
3 beds | 3 baths | 2,186 sq.ft. |
$304,900 |
Airbnb cash on cash: 2.67%
|
Real Estate investment in Middlebury, IN
There are 34 properties for sale in the city of Middlebury . The median list price in Middlebury is $329,830 and the average price per square foot is $133. In June 2026, the average monthly cash on cash return in Middlebury is 5.00%. The average monthly rental income in Middlebury is $3,020.