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.

San Rafael Hill Investment Property for Sale in Middlebury, IN

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

Showing 15 San Rafael Hill Investment Property 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%
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%
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 Saturday 12/6/2025 12-2PM. Welcome home to this beautifully updated quad-level...	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.	$250,000	Airbnb cash on cash: 2.68% Traditional cash on cash: 9.23% Airbnb Rental Income: $1597 Traditional Rental Income: $2689 Airbnb ROI: 2.68% Traditional ROI: 9.23%
231 River Park Drive Middlebury, IN Welcome to the Villas of River Park in beautiful Middleburyâthe perfect blend of comfort...	2 beds \| 2 baths \| 1,237 sq.ft.	$314,900	Airbnb cash on cash: -0.05% Traditional cash on cash: 4.15% Airbnb Rental Income: $1230 Traditional Rental Income: $2080 Airbnb ROI: -0.05% Traditional ROI: 4.15%
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.	$599,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 3.98% Airbnb Rental Income: $1597 Traditional Rental Income: $3423 Airbnb ROI: -0.1% Traditional ROI: 3.98%

Your search for investment property begins and ends here

San Rafael Hill 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%