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.

Single Family Homes for Sale in Middlebury, IN

Search for Single Family Residential for Sale in Middlebury, Indiana. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 16 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
622 Bristol Avenue Middlebury, IN Open House Scheduled for August 23 1-3pm! A stone bridge and layered landscaping set the ...	5 beds \| 9 baths \| 8,414 sq.ft.	$1,970,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.38% Airbnb Rental Income: $null Traditional Rental Income: $7301 Airbnb ROI: N/A Traditional ROI: 1.38%
608 Fieldstone Lane Middlebury, IN Adorable Ranch located in Northridge School District- situated on a cul-de-sac--This home ...	3 beds \| 2 baths \| 2,252 sq.ft.	$289,900	Airbnb cash on cash: 2.7% Traditional cash on cash: 7.72% Airbnb Rental Income: $1850 Traditional Rental Income: $2724 Airbnb ROI: 2.7% Traditional ROI: 7.72%
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.	$369,990	Airbnb cash on cash: N/A Traditional cash on cash: 6.22% Airbnb Rental Income: $null Traditional Rental Income: $2948 Airbnb ROI: N/A Traditional ROI: 6.22%
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.	$369,990	Airbnb cash on cash: N/A Traditional cash on cash: 6.15% Airbnb Rental Income: $null Traditional Rental Income: $2923 Airbnb ROI: N/A Traditional ROI: 6.15%
13909 Shavano Peak Drive Middlebury, IN Stunning ... New Construction! The property is still in the early stages, giving you the p...	3 beds \| 3 baths \| 2,569 sq.ft.	$689,760	Airbnb cash on cash: 0.86% Traditional cash on cash: 3.85% Airbnb Rental Income: $1850 Traditional Rental Income: $3276 Airbnb ROI: 0.86% Traditional ROI: 3.85%
11306 Fishers Pond Middlebury, IN This stunning home is truly inspired by The Farm as this farm-style gem is straight from a...	5 beds \| 4 baths \| 4,326 sq.ft.	$974,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.62% Airbnb Rental Income: $null Traditional Rental Income: $4007 Airbnb ROI: N/A Traditional ROI: 2.62%
51561 E County Line Road Middlebury, IN Looking for a new construction with an incredible view? Look no further! This 3 bedroom,...	3 beds \| 2 baths \| 1,708 sq.ft.	$329,900	Airbnb cash on cash: 3.02% Traditional cash on cash: 7.1% Airbnb Rental Income: $1850 Traditional Rental Income: $2618 Airbnb ROI: 3.02% Traditional ROI: 7.1%
735 Oakleaf Drive Middlebury, IN New Construction in the beautiful community of Parkrose, featuring the stunning Beacon Mod...	3 beds \| 2 baths \| 1,414 sq.ft.	$324,990	Airbnb cash on cash: 2.1% Traditional cash on cash: 4.79% Airbnb Rental Income: $1850 Traditional Rental Income: $2175 Airbnb ROI: 2.1% Traditional ROI: 4.79%
611 Claudia Lane Middlebury, IN Across from Northridge High School! Enjoy the convenience of being just minutes from North...	4 beds \| 3 baths \| 2,464 sq.ft.	$390,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.63% Airbnb Rental Income: $null Traditional Rental Income: $3208 Airbnb ROI: N/A Traditional ROI: 6.63%
10281 County Road 4 Middlebury, IN Peace is all you will think of at this home. Nestled on nearly 2 acres in the desirable Mi...	3 beds \| 1 baths \| 1,990 sq.ft.	$395,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 3.24% Airbnb Rental Income: $1850 Traditional Rental Income: $1988 Airbnb ROI: 1.52% Traditional ROI: 3.24%
510 Crystal Valley Drive Middlebury, IN Nestled on just under 2 acres, this unique property offers privacy in town â you wonât...	3 beds \| 3 baths \| 2,552 sq.ft.	$415,000	Airbnb cash on cash: 1.37% Traditional cash on cash: 5.72% Airbnb Rental Income: $1850 Traditional Rental Income: $3046 Airbnb ROI: 1.37% Traditional ROI: 5.72%
52690 Rachael Court Middlebury, IN New Construction in Middlebury Schools! Tucked in the back of Sandy Hill at the end of a...	3 beds \| 2 baths \| 1,248 sq.ft.	$324,000	Airbnb cash on cash: 2.83% Traditional cash on cash: 5.96% Airbnb Rental Income: $1850 Traditional Rental Income: $2306 Airbnb ROI: 2.83% Traditional ROI: 5.96%
53048 State Road 13 Middlebury, IN Welcome to your private oasis just minutes from town! This beautifully remodeled home sits...	3 beds \| 2 baths \| 2,862 sq.ft.	$345,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 6.4% Airbnb Rental Income: $1850 Traditional Rental Income: $2714 Airbnb ROI: 2.2% Traditional ROI: 6.4%
13149 State Rd 120 Middlebury, IN Welcome to this private 2-acre retreat in the Middlebury School District! This fully renov...	4 beds \| 2 baths \| 2,336 sq.ft.	$348,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.66% Airbnb Rental Income: $null Traditional Rental Income: $2724 Airbnb ROI: N/A Traditional ROI: 6.66%
52610 County Road 39 Middlebury, IN Welcome to this exceptional 65-acre property, offering the perfect blend of privacy, natur...	4 beds \| 5 baths \| 4,740 sq.ft.	$2,138,400	Airbnb cash on cash: N/A Traditional cash on cash: 0.92% Airbnb Rental Income: $null Traditional Rental Income: $5098 Airbnb ROI: N/A Traditional ROI: 0.92%
607 Claudia Lane Middlebury, IN Welcome to 607 Claudia Lane, perfectly situated on a spacious double lot in a quiet and de...	3 beds \| 2 baths \| 3,223 sq.ft.	$349,900	Airbnb cash on cash: 1.81% Traditional cash on cash: 5.19% Airbnb Rental Income: $1850 Traditional Rental Income: $2461 Airbnb ROI: 1.81% Traditional ROI: 5.19%

Your search for investment property begins and ends here

Single Family Homes for Sale in Middlebury, IN

622 Bristol Avenue

Middlebury, IN

5 beds | 9 baths | 8,414 sq.ft.

$1,970,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.38%

Airbnb Rental Income: $null

Traditional Rental Income: $7301

Airbnb ROI: N/A

Traditional ROI: 1.38%

608 Fieldstone Lane

Middlebury, IN

3 beds | 2 baths | 2,252 sq.ft.

$289,900

Airbnb cash on cash: 2.7%

Traditional cash on cash: 7.72%

Airbnb Rental Income: $1850

Traditional Rental Income: $2724

Airbnb ROI: 2.7%

Traditional ROI: 7.72%

750 Oakleaf Drive

Middlebury, IN

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

$369,990

Airbnb cash on cash: N/A

Traditional cash on cash: 6.22%

Airbnb Rental Income: $null

Traditional Rental Income: $2948

Airbnb ROI: N/A

Traditional ROI: 6.22%

792 Oakleaf Drive

Middlebury, IN

4 beds | 3 baths | 2,491 sq.ft.

$369,990

Airbnb cash on cash: N/A

Traditional cash on cash: 6.15%

Airbnb Rental Income: $null

Traditional Rental Income: $2923

Airbnb ROI: N/A

Traditional ROI: 6.15%

13909 Shavano Peak Drive

Middlebury, IN

3 beds | 3 baths | 2,569 sq.ft.

$689,760

Airbnb cash on cash: 0.86%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $1850

Traditional Rental Income: $3276

Airbnb ROI: 0.86%

Traditional ROI: 3.85%

11306 Fishers Pond

Middlebury, IN

5 beds | 4 baths | 4,326 sq.ft.

$974,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.62%

Airbnb Rental Income: $null

Traditional Rental Income: $4007

Airbnb ROI: N/A

Traditional ROI: 2.62%

51561 E County Line Road

Middlebury, IN

3 beds | 2 baths | 1,708 sq.ft.

$329,900

Airbnb cash on cash: 3.02%

Traditional cash on cash: 7.1%

Airbnb Rental Income: $1850

Traditional Rental Income: $2618

Airbnb ROI: 3.02%

Traditional ROI: 7.1%

735 Oakleaf Drive

Middlebury, IN

3 beds | 2 baths | 1,414 sq.ft.

$324,990

Airbnb cash on cash: 2.1%

Traditional cash on cash: 4.79%

Airbnb Rental Income: $1850

Traditional Rental Income: $2175

Airbnb ROI: 2.1%