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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
53564 State Road 13 Middlebury, IN This beautiful walk-out ranch is located in Anchor Ridge a secluded neighborhood on the no...	5 beds \| 5 baths \| 4,212 sq.ft.	$697,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.44% Airbnb Rental Income: $null Traditional Rental Income: $4748 Airbnb ROI: N/A Traditional ROI: 5.44%
13460 Cedar Creek Heights Middlebury, IN Immaculately maintained and unmatched quality home that is second to none. Custom built on...	5 beds \| 5 baths \| 6,087 sq.ft.	$899,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.51% Airbnb Rental Income: $null Traditional Rental Income: $4760 Airbnb ROI: N/A Traditional ROI: 3.51%
103 Powell Drive Middlebury, IN Middlebury Schools! This 3 bedroom home is located on a quiet private drive near town. La...	3 beds \| 2 baths \| 1,320 sq.ft.	$219,700	Airbnb cash on cash: 8.77% Traditional cash on cash: 8.27% Airbnb Rental Income: $2969 Traditional Rental Income: $2181 Airbnb ROI: 8.77% Traditional ROI: 8.27%
1113 Bonnie Court Middlebury, IN Introducing a brand new "Under construction" home featuring 4 bedrooms, 3 baths, and 2,946...	4 beds \| 3 baths \| 2,946 sq.ft.	$449,900	Airbnb cash on cash: 7.18% Traditional cash on cash: 6.63% Airbnb Rental Income: $4478 Traditional Rental Income: $3314 Airbnb ROI: 7.18% Traditional ROI: 6.63%
824 Spring Meadow Farm Drive Middlebury, IN Discover luxury living in this meticulously maintained, nearly 5,000 sq ft executive home,...	5 beds \| 6 baths \| 4,894 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.64% Airbnb Rental Income: $null Traditional Rental Income: $6042 Airbnb ROI: N/A Traditional ROI: 8.64%
11334 Fishers Pond Middlebury, IN Check out this amazing 5 bedroom 3.5 bath home located in the highly desirable The Farm su...	5 beds \| 4 baths \| 3,923 sq.ft.	$634,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.5% Airbnb Rental Income: $null Traditional Rental Income: $3784 Airbnb ROI: N/A Traditional ROI: 4.5%
11305 Echo Valley Middlebury, IN Why BUILD when your dream home is officially on the market? Check out this custom one stor...	5 beds \| 3 baths \| 3,977 sq.ft.	$660,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.84% Airbnb Rental Income: $null Traditional Rental Income: $3571 Airbnb ROI: N/A Traditional ROI: 3.84%
56406 Ponderosa Path Middlebury, IN Nearly new 4 bedroom, 3 full bath home built in 2022 by Team Construction. Located in Ever...	4 beds \| 3 baths \| 2,459 sq.ft.	$519,000	Airbnb cash on cash: 5.33% Traditional cash on cash: 4.3% Airbnb Rental Income: $4478 Traditional Rental Income: $3043 Airbnb ROI: 5.33% Traditional ROI: 4.3%
60359 State Road 13 Middlebury, IN Get ready to fall in love with this adorable 2-bedroom home situated on over a half acre! ...	2 beds \| 1 baths \| 757 sq.ft.	$189,900	Airbnb cash on cash: 5.31% Traditional cash on cash: 6.03% Airbnb Rental Income: $1766 Traditional Rental Income: $1412 Airbnb ROI: 5.31% Traditional ROI: 6.03%
53422 County Road 43 Road Middlebury, IN This ranch style 3 (possible 4) bdrm 3 bath home with full basement, is awaiting its new o...	3 beds \| 3 baths \| 2,934 sq.ft.	$334,900	Airbnb cash on cash: 5.27% Traditional cash on cash: 8.59% Airbnb Rental Income: $2969 Traditional Rental Income: $3330 Airbnb ROI: 5.27% Traditional ROI: 8.59%
11500 County Road 10 Middlebury, IN Waterfront Middlebury Schools! This large modern walk out Ranch Home has over 2,700 finish...	5 beds \| 4 baths \| 2,756 sq.ft.	$339,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.27% Airbnb Rental Income: $null Traditional Rental Income: $3564 Airbnb ROI: N/A Traditional ROI: 9.27%
11608 Maple Ridge Drive Middlebury, IN Take a look at this fantastic 3-bedroom, 3.5-bath home sitting on 3 acres! Located in Midd...	3 beds \| 4 baths \| 3,075 sq.ft.	$574,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 4.41% Airbnb Rental Income: $2969 Traditional Rental Income: $3353 Airbnb ROI: 2.42% Traditional ROI: 4.41%
131 River Park Drive Middlebury, IN Open House Sunday December 8th 1-3, Christmas Treats will be Available! Discover this invi...	2 beds \| 2 baths \| 1,457 sq.ft.	$319,900	Airbnb cash on cash: 1.34% Traditional cash on cash: 4.95% Airbnb Rental Income: $1766 Traditional Rental Income: $2370 Airbnb ROI: 1.34% Traditional ROI: 4.95%
118 Krider Drive Middlebury, IN Discover the perfect home for your familyâs growth in this impressive 5-bedroom residenc...	5 beds \| 4 baths \| 2,556 sq.ft.	$344,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.21% Airbnb Rental Income: $null Traditional Rental Income: $3340 Airbnb ROI: N/A Traditional ROI: 8.21%
505 Skyview Drive Middlebury, IN 3900 square foot welcomes you to this 2 Story Home Featuring 4 large bedrooms, 2 1/2 baths...	4 beds \| 3 baths \| 3,600 sq.ft.	$414,900	Airbnb cash on cash: 7.13% Traditional cash on cash: 6.46% Airbnb Rental Income: $4478 Traditional Rental Income: $3283 Airbnb ROI: 7.13% Traditional ROI: 6.46%
607 Fieldstone Lane Middlebury, IN Multiple Offers, Highest and Best offers due by 7pm October 29th. MIDDLEBURY SCHOOLS!! T...	3 beds \| 2 baths \| 1,350 sq.ft.	$230,000	Airbnb cash on cash: 8.35% Traditional cash on cash: 8.58% Airbnb Rental Income: $2969 Traditional Rental Income: $2335 Airbnb ROI: 8.35% Traditional ROI: 8.58%
53640 Forest Lakes Drive Middlebury, IN Step into this impressive custom-built home on a quiet cul-de-sac in the Forest Lakes neig...	3 beds \| 4 baths \| 4,634 sq.ft.	$729,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 3.39% Airbnb Rental Income: $2969 Traditional Rental Income: $3597 Airbnb ROI: 1.46% Traditional ROI: 3.39%
10095 County Road 16 Middlebury, IN Welcome to peaceful country living in this impressive two-story home in Middlebury schools...	5 beds \| 4 baths \| 4,172 sq.ft.	$580,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.04% Airbnb Rental Income: $null Traditional Rental Income: $3841 Airbnb ROI: N/A Traditional ROI: 5.04%
406 Crystal Valley Drive #10 Middlebury, IN This cozy 2 bedroom 1 bath condo/villa is ready for you!!! Maintenance free living is wha...	2 beds \| 1 baths \| 1,582 sq.ft.	$139,900	Airbnb cash on cash: 5.87% Traditional cash on cash: 9.15% Airbnb Rental Income: $1766 Traditional Rental Income: $1723 Airbnb ROI: 5.87% Traditional ROI: 9.15%
11707 County Road 24 Middlebury, IN Country Home for Sale. Discover your peaceful retreat in this delightful country home, pe...	3 beds \| 2 baths \| 1,572 sq.ft.	$269,900	Airbnb cash on cash: 7.03% Traditional cash on cash: 7.22% Airbnb Rental Income: $2969 Traditional Rental Income: $2333 Airbnb ROI: 7.03% Traditional ROI: 7.22%
13107 Cedar Creek Drive Middlebury, IN Welcome to Cedar Creek in Middlebury; meticulously updated and completely move-in ready! S...	4 beds \| 3 baths \| 3,094 sq.ft.	$475,000	Airbnb cash on cash: 6.09% Traditional cash on cash: 5.52% Airbnb Rental Income: $4478 Traditional Rental Income: $3291 Airbnb ROI: 6.09% Traditional ROI: 5.52%

Real Estate investment in Middlebury, IN

There are 21 properties for sale in the city of Middlebury . The median list price in Middlebury is $449,900 and the average price per square foot is $149. In December 2024, the average monthly cash on cash return in Middlebury is 6.00%. The average monthly rental income in Middlebury is $3,322.

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

There are 21 investment properties available for sale in Middlebury.

In 2024, the best neighborhood to buy investment property is Middlebury.

The ROI for Short-Term is higher than the Long-Term in Middlebury with average rental income of $2,969.

Your search for investment property begins and ends here

Investment Property for Sale in Middlebury, IN

53564 State Road 13

Middlebury, IN

5 beds | 5 baths | 4,212 sq.ft.

$697,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.44%

Airbnb Rental Income: $null

Traditional Rental Income: $4748

Airbnb ROI: N/A

Traditional ROI: 5.44%

13460 Cedar Creek Heights

Middlebury, IN

5 beds | 5 baths | 6,087 sq.ft.

$899,999

Airbnb cash on cash: N/A

Traditional cash on cash: 3.51%

Airbnb Rental Income: $null

Traditional Rental Income: $4760

Airbnb ROI: N/A

Traditional ROI: 3.51%

103 Powell Drive

Middlebury, IN

3 beds | 2 baths | 1,320 sq.ft.

$219,700

Airbnb cash on cash: 8.77%

Traditional cash on cash: 8.27%

Airbnb Rental Income: $2969

Traditional Rental Income: $2181

Airbnb ROI: 8.77%

Traditional ROI: 8.27%

1113 Bonnie Court

Middlebury, IN

4 beds | 3 baths | 2,946 sq.ft.

$449,900

Airbnb cash on cash: 7.18%

Traditional cash on cash: 6.63%

Airbnb Rental Income: $4478

Traditional Rental Income: $3314

Airbnb ROI: 7.18%

Traditional ROI: 6.63%

824 Spring Meadow Farm Drive

Middlebury, IN

5 beds | 6 baths | 4,894 sq.ft.

$599,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.64%

Airbnb Rental Income: $null

Traditional Rental Income: $6042

Airbnb ROI: N/A

Traditional ROI: 8.64%

11334 Fishers Pond

Middlebury, IN

5 beds | 4 baths | 3,923 sq.ft.

$634,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.5%

Airbnb Rental Income: $null

Traditional Rental Income: $3784

Airbnb ROI: N/A

Traditional ROI: 4.5%

11305 Echo Valley

Middlebury, IN

5 beds | 3 baths | 3,977 sq.ft.

$660,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.84%

Airbnb Rental Income: $null

Traditional Rental Income: $3571

Airbnb ROI: N/A

Traditional ROI: 3.84%

56406 Ponderosa Path

Middlebury, IN

4 beds | 3 baths | 2,459 sq.ft.

$519,000

Airbnb cash on cash: 5.33%

Traditional cash on cash: 4.3%

Airbnb Rental Income: $4478

Traditional Rental Income: $3043

Airbnb ROI: 5.33%