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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
767 Oakleaf Drive Middlebury, IN New 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: 4.05% Traditional cash on cash: 6.12% Airbnb Rental Income: $2565 Traditional Rental Income: $2579 Airbnb ROI: 4.05% Traditional ROI: 6.12%
14188 CR 28 Middlebury, IN Great, 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: 0.5% Traditional cash on cash: 2.47% Airbnb Rental Income: $1926 Traditional Rental Income: $2657 Airbnb ROI: 0.5% Traditional ROI: 2.47%
210 River Park Drive Middlebury, IN This beautifully appointed villa in the quaint town of Middlebury is where comfort, qualit...	3 beds \| 3 baths \| 2,800 sq.ft.	$419,900	Airbnb cash on cash: 0.82% Traditional cash on cash: 5.37% Airbnb Rental Income: $1926 Traditional Rental Income: $3206 Airbnb ROI: 0.82% Traditional ROI: 5.37%
518 Sunset Lane Middlebury, IN Welcome to this summer ready home on Sunset Dr. You will love the space, updates and ameni...	3 beds \| 2 baths \| 2,942 sq.ft.	$385,000	Airbnb cash on cash: 1.83% Traditional cash on cash: 5.82% Airbnb Rental Income: $1926 Traditional Rental Income: $2860 Airbnb ROI: 1.83% Traditional ROI: 5.82%
50701 County Road 37 Middlebury, IN Phone 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: 2.29% Traditional cash on cash: 6.68% Airbnb Rental Income: $1926 Traditional Rental Income: $2756 Airbnb ROI: 2.29% Traditional ROI: 6.68%
13452 County Road 12 Lot 3 Middlebury, IN Start Showing Date: 7/6/2026 Spacious secluded home two story home with 5 bedrooms and 3 b...	5 beds \| 3 baths \| 2,100 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.41% Airbnb Rental Income: $null Traditional Rental Income: $3081 Airbnb ROI: N/A Traditional ROI: 6.41%
518 Redbud Lane Middlebury, IN You will appreciate the many updates throughout this beautiful 4-bedroom, 2.5 bath home! E...	4 beds \| 3 baths \| 2,254 sq.ft.	$355,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 7.04% Airbnb Rental Income: $2565 Traditional Rental Income: $3027 Airbnb ROI: 3.8% Traditional ROI: 7.04%
53339 State Road 13 Middlebury, IN Take 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: 0.32% Traditional cash on cash: 1.91% Airbnb Rental Income: $2565 Traditional Rental Income: $3312 Airbnb ROI: 0.32% Traditional ROI: 1.91%
10281 County Road 4 Middlebury, IN Peace 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.	$379,900	Airbnb cash on cash: 1.8% Traditional cash on cash: 3.4% Airbnb Rental Income: $1926 Traditional Rental Income: $1988 Airbnb ROI: 1.8% Traditional ROI: 3.4%
1116 Erin Court Middlebury, IN Middlebury 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: 0.55% Traditional cash on cash: 4.56% Airbnb Rental Income: $1926 Traditional Rental Income: $3423 Airbnb ROI: 0.55% Traditional ROI: 4.56%
57051 County Road 33 Middlebury, IN Here'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: 0.59% Traditional cash on cash: 2.02% Airbnb Rental Income: $2565 Traditional Rental Income: $2938 Airbnb ROI: 0.59% Traditional ROI: 2.02%
609 Westlake Drive Middlebury, IN This 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.	$375,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 7.09% Airbnb Rental Income: $1926 Traditional Rental Income: $3155 Airbnb ROI: 2.15% Traditional ROI: 7.09%
13912 Shavano Peak Drive Middlebury, IN Looking 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: 1.85% Traditional cash on cash: 3.7% Airbnb Rental Income: $2565 Traditional Rental Income: $2880 Airbnb ROI: 1.85% Traditional ROI: 3.7%
54646 State Road 13 Middlebury, IN Charming 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: 2.46% Traditional cash on cash: 6.44% Airbnb Rental Income: $1926 Traditional Rental Income: $2723 Airbnb ROI: 2.46% Traditional ROI: 6.44%
509 Morningstar Court Middlebury, IN Open House Saturday, 6/13 11 AM - 1 PM and Sunday, 6/14 11 AM - 1 PM* Amazing Cape Cod...	4 beds \| 2 baths \| 1,456 sq.ft.	$259,000	Airbnb cash on cash: 5.94% Traditional cash on cash: 5.36% Airbnb Rental Income: $2565 Traditional Rental Income: $1806 Airbnb ROI: 5.94% Traditional ROI: 5.36%
13745 Ranier Drive Middlebury, IN Welcome 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: 2.49% Traditional cash on cash: 5.11% Airbnb Rental Income: $2565 Traditional Rental Income: $3093 Airbnb ROI: 2.49% Traditional ROI: 5.11%
242 River Park Drive Middlebury, 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: 0.59% Traditional cash on cash: 4.57% Airbnb Rental Income: $1926 Traditional Rental Income: $3132 Airbnb ROI: 0.59% Traditional ROI: 4.57%
12340 County Road 4 Middlebury, IN This 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: -0.01% Traditional cash on cash: 1.84% Airbnb Rental Income: $2565 Traditional Rental Income: $4019 Airbnb ROI: -0.01% Traditional ROI: 1.84%
56408 White Pine Ridge Middlebury, IN This 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: 0.73% Traditional cash on cash: 3.48% Airbnb Rental Income: $2565 Traditional Rental Income: $3938 Airbnb ROI: 0.73% Traditional ROI: 3.48%
53242 County Road 43 Middlebury, IN Open House Sunday May 31st from 1-3PM Motivated Seller Spacious 4-bedroom, 2-bath ...	4 beds \| 2 baths \| 2,107 sq.ft.	$359,900	Airbnb cash on cash: 4% Traditional cash on cash: 7.18% Airbnb Rental Income: $2565 Traditional Rental Income: $3023 Airbnb ROI: 4% Traditional ROI: 7.18%
54721 State Road 13 Middlebury, IN AUCTION! 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: 1.42% Traditional cash on cash: 4.8% Airbnb Rental Income: $1090 Traditional Rental Income: $1368 Airbnb ROI: 1.42% Traditional ROI: 4.8%
55822 Alverstone Drive Middlebury, IN Step 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: 2.08% Traditional cash on cash: 5.29% Airbnb Rental Income: $2565 Traditional Rental Income: $3448 Airbnb ROI: 2.08% Traditional ROI: 5.29%
203 Eugene Drive Middlebury, IN Move 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: 1.94% Traditional cash on cash: 10.72% Airbnb Rental Income: $1926 Traditional Rental Income: $4544 Airbnb ROI: 1.94% Traditional ROI: 10.72%
329 Bristol Avenue Middlebury, IN Great 3 Bedroom 2 Bath Home close to downtown Middlebury.	3 beds \| 3 baths \| 2,186 sq.ft.	$304,900	Airbnb cash on cash: 2.9% Traditional cash on cash: 8.41% Airbnb Rental Income: $1926 Traditional Rental Income: $2996 Airbnb ROI: 2.9% Traditional ROI: 8.41%

Real Estate investment in Middlebury, IN

There are 24 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 $138. In July 2026, the average monthly cash on cash return in Middlebury is 5.00%. The average monthly rental income in Middlebury is $3,025.

Middlebury, IN Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 24 investment properties available for sale in Middlebury.

In 2026, the best neighborhood to buy investment property is Middlebury.

The ROI for Long-Term is higher than the Short-Term in Middlebury with average rental income of $3,025.

Your search for investment property begins and ends here

Investment Property for Sale in Middlebury, IN

767 Oakleaf Drive

Middlebury, IN

4 beds | 3 baths | 1,842 sq.ft.

$324,990

Airbnb cash on cash: 4.05%

Traditional cash on cash: 6.12%

Airbnb Rental Income: $2565

Traditional Rental Income: $2579

Airbnb ROI: 4.05%

Traditional ROI: 6.12%

14188 CR 28

Middlebury, IN

3 beds | 2 baths | 2,300 sq.ft.

$675,000

Airbnb cash on cash: 0.5%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $1926

Traditional Rental Income: $2657

Airbnb ROI: 0.5%

Traditional ROI: 2.47%

210 River Park Drive

Middlebury, IN

3 beds | 3 baths | 2,800 sq.ft.

$419,900

Airbnb cash on cash: 0.82%

Traditional cash on cash: 5.37%

Airbnb Rental Income: $1926

Traditional Rental Income: $3206

Airbnb ROI: 0.82%

Traditional ROI: 5.37%

518 Sunset Lane

Middlebury, IN

3 beds | 2 baths | 2,942 sq.ft.

$385,000

Airbnb cash on cash: 1.83%

Traditional cash on cash: 5.82%

Airbnb Rental Income: $1926

Traditional Rental Income: $2860

Airbnb ROI: 1.83%

Traditional ROI: 5.82%

50701 County Road 37

Middlebury, IN

3 beds | 2 baths | 2,545 sq.ft.

$325,000

Airbnb cash on cash: 2.29%

Traditional cash on cash: 6.68%

Airbnb Rental Income: $1926

Traditional Rental Income: $2756

Airbnb ROI: 2.29%

Traditional ROI: 6.68%

13452 County Road 12 Lot 3

Middlebury, IN

5 beds | 3 baths | 2,100 sq.ft.

$399,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.41%

Airbnb Rental Income: $null

Traditional Rental Income: $3081

Airbnb ROI: N/A

Traditional ROI: 6.41%

518 Redbud Lane

Middlebury, IN

4 beds | 3 baths | 2,254 sq.ft.

$355,000

Airbnb cash on cash: 3.8%

Traditional cash on cash: 7.04%

Airbnb Rental Income: $2565

Traditional Rental Income: $3027

Airbnb ROI: 3.8%

Traditional ROI: 7.04%

53339 State Road 13

Middlebury, IN

4 beds | 4 baths | 3,528 sq.ft.

$920,000

Airbnb cash on cash: 0.32%

Traditional cash on cash: 1.91%

Airbnb Rental Income: $2565

Traditional Rental Income: $3312

Airbnb ROI: 0.32%