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.

Condos for Sale in Middlebury, IN

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

Showing 1 Condo 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
209 River Park Drive Middlebury, IN Maintenance Free Living in Middlebury!!! Well maintained condo in the Villas of River Par...	2 beds \| 2 baths \| 1,675 sq.ft.	$349,900	Airbnb cash on cash: -1.19% Traditional cash on cash: 3.39% Airbnb Rental Income: $1230 Traditional Rental Income: $2342 Airbnb ROI: -1.19% Traditional ROI: 3.39%
Other Investment Properties for Sale in Middlebury
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%
525 S Main St Middlebury , IN ON THE PUMPKIN VINE.....This nearly one acre lot in town features a 4 bedroom, 2 bath home...	4 beds \| 2 baths \| 1,972 sq.ft.	$339,000	Airbnb cash on cash: 3.76% Traditional cash on cash: 5.73% Airbnb Rental Income: $2453 Traditional Rental Income: $2483 Airbnb ROI: 3.76% Traditional ROI: 5.73%
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%
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.	$318,990	Airbnb cash on cash: 1.47% Traditional cash on cash: 4.92% Airbnb Rental Income: $1597 Traditional Rental Income: $2175 Airbnb ROI: 1.47% Traditional ROI: 4.92%
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.	$390,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 6.15% Airbnb Rental Income: $1597 Traditional Rental Income: $3046 Airbnb ROI: 0.94% Traditional ROI: 6.15%
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.	$1,199,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.73% Airbnb Rental Income: $null Traditional Rental Income: $3669 Airbnb ROI: N/A Traditional ROI: 1.73%
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.	$334,900	Airbnb cash on cash: 1.57% Traditional cash on cash: 6.09% Airbnb Rental Income: $1597 Traditional Rental Income: $2563 Airbnb ROI: 1.57% Traditional ROI: 6.09%
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.	$220,000	Airbnb cash on cash: 3.17% Traditional cash on cash: 10.6% Airbnb Rental Income: $1597 Traditional Rental Income: $2689 Airbnb ROI: 3.17% Traditional ROI: 10.6%
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.	$585,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 4.09% Airbnb Rental Income: $1597 Traditional Rental Income: $3423 Airbnb ROI: -0.08% Traditional ROI: 4.09%
12225 County Road 4 Middlebury , IN AUCTION!! This 3 acre property is selling at Phone Bid auction with bidding to end on Feb ...	4 beds \| 2 baths \| 4,656 sq.ft.	$525,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 3.24% Airbnb Rental Income: $2453 Traditional Rental Income: $2690 Airbnb ROI: 1.54% Traditional ROI: 3.24%
312 Bristol Ave Middlebury , IN 312 Bristol Ave, Middlebury, IN 46540 \| Single Family Residential	4 beds \| 2 baths \| 3,640 sq.ft.	$444,900	Airbnb cash on cash: 2.39% Traditional cash on cash: 3.29% Airbnb Rental Income: $2453 Traditional Rental Income: $2230 Airbnb ROI: 2.39% Traditional ROI: 3.29%
56085 CR 33 Middlebury , IN 56085 CR 33, Middlebury, IN 46540 \| Single Family Residential	4 beds \| 3 baths \| 2,856 sq.ft.	$739,500	Airbnb cash on cash: 0.71% Traditional cash on cash: 2.34% Airbnb Rental Income: $2453 Traditional Rental Income: $2981 Airbnb ROI: 0.71% Traditional ROI: 2.34%
53982 Midnight Star Middlebury , IN 53982 Midnight Star, Middlebury, IN 46540 \| Other	N/A beds \| N/A baths \| N/A	$90,000	Airbnb cash on cash: 2.39% Traditional cash on cash: 5.97% Airbnb Rental Income: $785 Traditional Rental Income: $780 Airbnb ROI: 2.39% Traditional ROI: 5.97%
14483 County Road 8 Middlebury , IN 14483 County Road 8, Middlebury, IN 46540 \| Single Family Residential	3 beds \| 2 baths \| 1,568 sq.ft.	$369,900	Airbnb cash on cash: 1.18% Traditional cash on cash: 3.95% Airbnb Rental Income: $1597 Traditional Rental Income: $2105 Airbnb ROI: 1.18% Traditional ROI: 3.95%

Your search for investment property begins and ends here

Condos for Sale in Middlebury, IN

209 River Park Drive

Middlebury, IN

2 beds | 2 baths | 1,675 sq.ft.

$349,900

Airbnb cash on cash: -1.19%

Traditional cash on cash: 3.39%

Airbnb Rental Income: $1230

Traditional Rental Income: $2342

Airbnb ROI: -1.19%

Traditional ROI: 3.39%

Other Investment Properties for Sale in Middlebury

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%

Middlebury , IN

4 beds | 2 baths | 1,972 sq.ft.

$339,000

Airbnb cash on cash: 3.76%

Traditional cash on cash: 5.73%

Airbnb Rental Income: $2453

Traditional Rental Income: $2483

Airbnb ROI: 3.76%

Traditional ROI: 5.73%

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%

Middlebury , IN

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

$318,990

Airbnb cash on cash: 1.47%

Traditional cash on cash: 4.92%

Airbnb Rental Income: $1597

Traditional Rental Income: $2175

Airbnb ROI: 1.47%

Traditional ROI: 4.92%

Middlebury , IN

3 beds | 3 baths | 2,552 sq.ft.

$390,000

Airbnb cash on cash: 0.94%

Traditional cash on cash: 6.15%

Airbnb Rental Income: $1597

Traditional Rental Income: $3046

Airbnb ROI: 0.94%

Traditional ROI: 6.15%

Middlebury , IN

5 beds | 4 baths | 3,038 sq.ft.

$1,199,900

Airbnb cash on cash: N/A

Traditional cash on cash: 1.73%

Airbnb Rental Income: $null

Traditional Rental Income: $3669

Airbnb ROI: N/A

Traditional ROI: 1.73%

Middlebury , IN

3 beds | 3 baths | 1,618 sq.ft.

$334,900

Airbnb cash on cash: 1.57%

Traditional cash on cash: 6.09%

Airbnb Rental Income: $1597

Traditional Rental Income: $2563

Airbnb ROI: 1.57%

Traditional ROI: 6.09%

Middlebury , IN

3 beds | 2 baths | 2,246 sq.ft.

$220,000

Airbnb cash on cash: 3.17%

Traditional cash on cash: 10.6%