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
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%
214 Krider Drive Middlebury, IN Location, lifestyle, and comfort await you in this classic 4-bedroom, 2.5-bath home, just ...	4 beds \| 3 baths \| 2,628 sq.ft.	$349,900	Airbnb cash on cash: 3.5% Traditional cash on cash: 8.56% Airbnb Rental Income: $2453 Traditional Rental Income: $3519 Airbnb ROI: 3.5% Traditional ROI: 8.56%
824 Spring Meadow Farm Drive Middlebury, IN Welcome to Middlebury featuring this executive home on Meadow Valley Golf Course with the ...	5 beds \| 6 baths \| 4,384 sq.ft.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.43% Airbnb Rental Income: $null Traditional Rental Income: $6042 Airbnb ROI: N/A Traditional ROI: 9.43%
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: 3.08% Traditional cash on cash: 6.22% Airbnb Rental Income: $2453 Traditional Rental Income: $2948 Airbnb ROI: 3.08% 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.	$344,990	Airbnb cash on cash: 3.43% Traditional cash on cash: 6.72% Airbnb Rental Income: $2453 Traditional Rental Income: $2923 Airbnb ROI: 3.43% Traditional ROI: 6.72%
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.	$950,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.71% Airbnb Rental Income: $null Traditional Rental Income: $4007 Airbnb ROI: N/A Traditional ROI: 2.71%
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.	$319,990	Airbnb cash on cash: 1.46% Traditional cash on cash: 4.89% Airbnb Rental Income: $1597 Traditional Rental Income: $2175 Airbnb ROI: 1.46% Traditional ROI: 4.89%
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: 0.95% Traditional cash on cash: 3.24% Airbnb Rental Income: $1597 Traditional Rental Income: $1988 Airbnb ROI: 0.95% 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: 0.82% Traditional cash on cash: 5.72% Airbnb Rental Income: $1597 Traditional Rental Income: $3046 Airbnb ROI: 0.82% Traditional ROI: 5.72%
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.	$1,950,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 1.11% Airbnb Rental Income: $2453 Traditional Rental Income: $5098 Airbnb ROI: -0.68% Traditional ROI: 1.11%
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: 1.17% Traditional cash on cash: 5.19% Airbnb Rental Income: $1597 Traditional Rental Income: $2461 Airbnb ROI: 1.17% Traditional ROI: 5.19%
1011 Spring Arbor Drive Middlebury, IN Beautifully renovated 5-bedroom, 1.5-bath home located in the highly desired Middlebury Sc...	5 beds \| 2 baths \| 2,016 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.79% Airbnb Rental Income: $null Traditional Rental Income: $2839 Airbnb ROI: N/A Traditional ROI: 8.79%
52478 County Road 39 Middlebury, IN Tucked away on nearly 10 acres in Middlebury, this 2022 custom stick-built home offers a p...	5 beds \| 4 baths \| 3,038 sq.ft.	$1,299,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.52% Airbnb Rental Income: $null Traditional Rental Income: $3669 Airbnb ROI: N/A Traditional ROI: 1.52%
510 Caprice Drive Middlebury, IN Open House Sunday 11/23 2-4PM. Welcome home to this beautifully updated quad-level home i...	3 beds \| 3 baths \| 1,618 sq.ft.	$344,900	Airbnb cash on cash: 1.5% Traditional cash on cash: 5.89% Airbnb Rental Income: $1597 Traditional Rental Income: $2563 Airbnb ROI: 1.5% Traditional ROI: 5.89%
200 E Berry Street Middlebury, IN Charming Downtown Middlebury Living! Nestled on a desirable corner lot in the heart of dow...	3 beds \| 2 baths \| 2,246 sq.ft.	$265,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 8.66% Airbnb Rental Income: $1597 Traditional Rental Income: $2689 Airbnb ROI: 2.48% Traditional ROI: 8.66%

Real Estate investment in Middlebury, IN

There are 15 properties for sale in the city of Middlebury . The median list price in Middlebury is $369,990 and the average price per square foot is $116. In December 2025, the average monthly cash on cash return in Middlebury is 6.00%. The average monthly rental income in Middlebury is $2,936.

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

There are 15 investment properties available for sale in Middlebury.

In 2025, 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 $2,936.

Your search for investment property begins and ends here

Investment Property 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%

214 Krider Drive

Middlebury, IN

4 beds | 3 baths | 2,628 sq.ft.

$349,900

Airbnb cash on cash: 3.5%

Traditional cash on cash: 8.56%

Airbnb Rental Income: $2453

Traditional Rental Income: $3519

Airbnb ROI: 3.5%

Traditional ROI: 8.56%

824 Spring Meadow Farm Drive

Middlebury, IN

5 beds | 6 baths | 4,384 sq.ft.

$549,900

Airbnb cash on cash: N/A

Traditional cash on cash: 9.43%

Airbnb Rental Income: $null

Traditional Rental Income: $6042

Airbnb ROI: N/A

Traditional ROI: 9.43%

750 Oakleaf Drive

Middlebury, IN

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

$369,990

Airbnb cash on cash: 3.08%

Traditional cash on cash: 6.22%

Airbnb Rental Income: $2453

Traditional Rental Income: $2948

Airbnb ROI: 3.08%

Traditional ROI: 6.22%

792 Oakleaf Drive

Middlebury, IN

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

$344,990

Airbnb cash on cash: 3.43%

Traditional cash on cash: 6.72%

Airbnb Rental Income: $2453

Traditional Rental Income: $2923

Airbnb ROI: 3.43%

Traditional ROI: 6.72%

11306 Fishers Pond

Middlebury, IN

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

$950,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.71%

Airbnb Rental Income: $null

Traditional Rental Income: $4007

Airbnb ROI: N/A

Traditional ROI: 2.71%

735 Oakleaf Drive

Middlebury, IN

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

$319,990

Airbnb cash on cash: 1.46%

Traditional cash on cash: 4.89%

Airbnb Rental Income: $1597

Traditional Rental Income: $2175

Airbnb ROI: 1.46%

Traditional ROI: 4.89%

10281 County Road 4

Middlebury, IN

3 beds | 1 baths | 1,990 sq.ft.

$395,000

Airbnb cash on cash: 0.95%

Traditional cash on cash: 3.24%

Airbnb Rental Income: $1597

Traditional Rental Income: $1988

Airbnb ROI: 0.95%