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
512 Redbud Lane Middlebury, IN Location! Location! Location! Northridge Schools!! Very well maitained home with three bed...	3 beds \| 3 baths \| 2,498 sq.ft.	$286,900	Airbnb cash on cash: 5.26% Traditional cash on cash: 8.97% Airbnb Rental Income: $2581 Traditional Rental Income: $2963 Airbnb ROI: 5.26% Traditional ROI: 8.97%
203 Krider Drive Middlebury, IN Back on Market at no fault of the seller. * This Middlebury 2-story home is close to ...	4 beds \| 3 baths \| 2,380 sq.ft.	$345,000	Airbnb cash on cash: 9.08% Traditional cash on cash: 4.58% Airbnb Rental Income: $4604 Traditional Rental Income: $2190 Airbnb ROI: 9.08% Traditional ROI: 4.58%
225 Greenfield Drive Middlebury, IN MIDDLEBURY SCHOOLS--This 1880 square foot walk-out Ranch nestled on just over a half acre ...	5 beds \| 3 baths \| 2,960 sq.ft.	$539,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.84% Airbnb Rental Income: $null Traditional Rental Income: $2391 Airbnb ROI: N/A Traditional ROI: 2.84%
312 W Bristol Street Middlebury, IN Nestled on scenic CR 8 near Krider Gardens and the Pumpkinvine Trail, this stunning 4-bedr...	4 beds \| 3 baths \| 3,640 sq.ft.	$460,000	Airbnb cash on cash: 6.48% Traditional cash on cash: 6.25% Airbnb Rental Income: $4604 Traditional Rental Income: $3550 Airbnb ROI: 6.48% Traditional ROI: 6.25%
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.	$749,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.41% Airbnb Rental Income: $null Traditional Rental Income: $4760 Airbnb ROI: N/A Traditional ROI: 4.41%
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.	$579,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.97% Airbnb Rental Income: $null Traditional Rental Income: $6042 Airbnb ROI: N/A Traditional ROI: 8.97%
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.	$609,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.72% Airbnb Rental Income: $null Traditional Rental Income: $3784 Airbnb ROI: N/A Traditional ROI: 4.72%
11608 Maple Ridge Drive Middlebury, IN Livestock friendly! A limitation of 2 animals. Take a look at this fantastic 3-bedroom, 3....	3 beds \| 4 baths \| 3,075 sq.ft.	$560,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 4.55% Airbnb Rental Income: $2581 Traditional Rental Income: $3353 Airbnb ROI: 1.89% Traditional ROI: 4.55%
750 Oakleaf Drive Middlebury, IN New Construction by Fischer Homes in the beautiful Parkrose community with the Jensen plan...	4 beds \| 3 baths \| 2,800 sq.ft.	$409,990	Airbnb cash on cash: 7.27% Traditional cash on cash: 5.45% Airbnb Rental Income: $4604 Traditional Rental Income: $2948 Airbnb ROI: 7.27% Traditional ROI: 5.45%
56142 Bridle Path Drive Middlebury, IN Are you ready to seize the opportunity to turn a house into your dream home? Look no furth...	3 beds \| 3 baths \| 2,040 sq.ft.	$354,900	Airbnb cash on cash: 3.89% Traditional cash on cash: 6.23% Airbnb Rental Income: $2581 Traditional Rental Income: $2743 Airbnb ROI: 3.89% Traditional ROI: 6.23%
981 Spring Crossing Drive Middlebury, IN Duplex - 3 bedroom 1 full bathroom on each side. 2-car garage on each side. Full partial...	6 beds \| 2 baths \| 2,277 sq.ft.	$299,900	Airbnb cash on cash: 4.07% Traditional cash on cash: 6.1% Airbnb Rental Income: $2581 Traditional Rental Income: $2535 Airbnb ROI: 4.07% Traditional ROI: 6.1%
13797 Denali Court Middlebury, IN Nestled on .82 Acres in the highly sought-after community of The Summit. With its spacious...	3 beds \| 2 baths \| 1,808 sq.ft.	$444,900	Airbnb cash on cash: 2.73% Traditional cash on cash: 4.5% Airbnb Rental Income: $2581 Traditional Rental Income: $2698 Airbnb ROI: 2.73% Traditional ROI: 4.5%
10275 Forest Lakes Drive Middlebury, IN Discover this home at 10275 Forest Lakes Drive, a spacious single-family home nestled in M...	3 beds \| 3 baths \| 2,640 sq.ft.	$419,900	Airbnb cash on cash: 2.63% Traditional cash on cash: 5.54% Airbnb Rental Income: $2581 Traditional Rental Income: $3107 Airbnb ROI: 2.63% Traditional ROI: 5.54%
12240 County Road 4 Road Middlebury, IN Phone bid auction! Listing Price reflects current bid. Situated beautifully down a 50...	4 beds \| 2 baths \| 4,608 sq.ft.	$775,000	Airbnb cash on cash: 3.28% Traditional cash on cash: 1.96% Airbnb Rental Income: $4604 Traditional Rental Income: $2692 Airbnb ROI: 3.28% Traditional ROI: 1.96%
988 Spring Crossing Drive Common Middlebury, IN Welcome home to this picture perfect ranch boasting many updates, a partially finished bas...	2 beds \| 2 baths \| 1,326 sq.ft.	$239,000	Airbnb cash on cash: 5.64% Traditional cash on cash: 6.75% Airbnb Rental Income: $2363 Traditional Rental Income: $2032 Airbnb ROI: 5.64% Traditional ROI: 6.75%
52772 Rachael Court Middlebury, IN Back on Market at NO FAULT of seller. Brand New Update, enjoy this 3 bedroom, 2 full ba...	3 beds \| 2 baths \| 1,120 sq.ft.	$216,000	Airbnb cash on cash: 7.69% Traditional cash on cash: 8.06% Airbnb Rental Income: $2581 Traditional Rental Income: $2037 Airbnb ROI: 7.69% Traditional ROI: 8.06%
764 Oakleaf Drive Middlebury, IN New Construction by Fischer Homes in the beautiful Hampton Walk community featuring the Yo...	4 beds \| 3 baths \| 2,256 sq.ft.	$389,990	Airbnb cash on cash: 7.88% Traditional cash on cash: 5.46% Airbnb Rental Income: $4604 Traditional Rental Income: $2765 Airbnb ROI: 7.88% Traditional ROI: 5.46%
136 River Park Drive Middlebury, IN Open House 4/27 1-3 PM... Maintenance-free living in Middlebury! Well maintained one owner...	3 beds \| 3 baths \| 1,998 sq.ft.	$334,900	Airbnb cash on cash: 3.41% Traditional cash on cash: 6.26% Airbnb Rental Income: $2581 Traditional Rental Income: $2860 Airbnb ROI: 3.41% Traditional ROI: 6.26%
13745 Ranier Drive Middlebury, IN Nestled in the highly sought-after "The Summit" neighborhood, this remarkable 4-bedroom, 3...	4 beds \| 3 baths \| 2,788 sq.ft.	$474,900	Airbnb cash on cash: 6.33% Traditional cash on cash: 5.08% Airbnb Rental Income: $4604 Traditional Rental Income: $3093 Airbnb ROI: 6.33% Traditional ROI: 5.08%
122 River Park Drive Common Middlebury, IN Welcome to easy living in this beautifully maintained 3-bedroom, 3-bath villa with a bonus...	3 beds \| 3 baths \| 2,521 sq.ft.	$329,900	Airbnb cash on cash: 3.37% Traditional cash on cash: 7.33% Airbnb Rental Income: $2581 Traditional Rental Income: $3188 Airbnb ROI: 3.37% Traditional ROI: 7.33%
792 Oakleaf Drive Middlebury, IN Trendy new Fairfax American Classic plan by Fischer Homes in beautiful Parkrose featuring ...	4 beds \| 3 baths \| 2,491 sq.ft.	$405,990	Airbnb cash on cash: 7.35% Traditional cash on cash: 5.45% Airbnb Rental Income: $4604 Traditional Rental Income: $2923 Airbnb ROI: 7.35% Traditional ROI: 5.45%
778 Oakleaf Drive Middlebury, IN Gorgeous new DaVinci Modern Farmhouse plan by Fischer Homes in beautiful Parkrose featurin...	3 beds \| 2 baths \| 1,756 sq.ft.	$379,990	Airbnb cash on cash: 3.25% Traditional cash on cash: 4.7% Airbnb Rental Income: $2581 Traditional Rental Income: $2479 Airbnb ROI: 3.25% Traditional ROI: 4.7%

Real Estate investment in Middlebury, IN

There are 22 properties for sale in the city of Middlebury . The median list price in Middlebury is $407,990 and the average price per square foot is $145. In April 2025, the average monthly cash on cash return in Middlebury is 5.00%. The average monthly rental income in Middlebury is $2,860.

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

There are 22 investment properties available for sale in Middlebury.

In 2025, 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 $2,581.

Your search for investment property begins and ends here

Investment Property for Sale in Middlebury, IN

512 Redbud Lane

Middlebury, IN

3 beds | 3 baths | 2,498 sq.ft.

$286,900

Airbnb cash on cash: 5.26%

Traditional cash on cash: 8.97%

Airbnb Rental Income: $2581

Traditional Rental Income: $2963

Airbnb ROI: 5.26%

Traditional ROI: 8.97%

203 Krider Drive

Middlebury, IN

4 beds | 3 baths | 2,380 sq.ft.

$345,000

Airbnb cash on cash: 9.08%

Traditional cash on cash: 4.58%

Airbnb Rental Income: $4604

Traditional Rental Income: $2190

Airbnb ROI: 9.08%

Traditional ROI: 4.58%

225 Greenfield Drive

Middlebury, IN

5 beds | 3 baths | 2,960 sq.ft.

$539,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.84%

Airbnb Rental Income: $null

Traditional Rental Income: $2391

Airbnb ROI: N/A

Traditional ROI: 2.84%

312 W Bristol Street

Middlebury, IN

4 beds | 3 baths | 3,640 sq.ft.

$460,000

Airbnb cash on cash: 6.48%

Traditional cash on cash: 6.25%

Airbnb Rental Income: $4604

Traditional Rental Income: $3550

Airbnb ROI: 6.48%

Traditional ROI: 6.25%

13460 Cedar Creek Heights

Middlebury, IN

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

$749,999

Airbnb cash on cash: N/A

Traditional cash on cash: 4.41%

Airbnb Rental Income: $null

Traditional Rental Income: $4760

Airbnb ROI: N/A

Traditional ROI: 4.41%

824 Spring Meadow Farm Drive

Middlebury, IN

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

$579,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.97%

Airbnb Rental Income: $null

Traditional Rental Income: $6042

Airbnb ROI: N/A

Traditional ROI: 8.97%

11334 Fishers Pond

Middlebury, IN

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

$609,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.72%

Airbnb Rental Income: $null

Traditional Rental Income: $3784

Airbnb ROI: N/A

Traditional ROI: 4.72%

11608 Maple Ridge Drive

Middlebury, IN

3 beds | 4 baths | 3,075 sq.ft.

$560,000

Airbnb cash on cash: 1.89%

Traditional cash on cash: 4.55%

Airbnb Rental Income: $2581

Traditional Rental Income: $3353

Airbnb ROI: 1.89%