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 50 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
767 Oakleaf Drive Middlebury, IN New construction by Fischer Homes in the beautiful Parkrose community, featuring the stunn...	4 beds \| 3 baths \| 1,842 sq.ft.	$324,990	Airbnb cash on cash: N/A Traditional cash on cash: 6.12% Airbnb Rental Income: $null Traditional Rental Income: $2579 Airbnb ROI: N/A Traditional ROI: 6.12%
101 Hemsberd St Middlebury, IN All new Carpeting and freshly painted. It has a Main Level Master Suite and an additional ...	3 beds \| 3 baths \| 1,788 sq.ft.	$309,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.47% Airbnb Rental Income: $null Traditional Rental Income: $2597 Airbnb ROI: N/A Traditional ROI: 6.47%
205 Greenfield Dr Middlebury, IN Top Quality all brick executive Middlebury home built by Town and Country Builders with ov...	6 beds \| 4 baths \| 6,412 sq.ft.	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.41% Airbnb Rental Income: $null Traditional Rental Income: $3808 Airbnb ROI: N/A Traditional ROI: 1.41%
928 S Main St Middlebury, IN Very well kept 3 BR Ranch Style home on the south side of Middlebury that sits on a genero...	3 beds \| 2 baths \| 2,116 sq.ft.	$289,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.67% Airbnb Rental Income: $null Traditional Rental Income: $2565 Airbnb ROI: N/A Traditional ROI: 7.67%
13889 Adirondack Ct Middlebury, IN Gorgeous home in Middlebury Schools! Custom built home. Extra deep garage, finished baseme...	5 beds \| 3 baths \| 4,473 sq.ft.	$789,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.08% Airbnb Rental Income: $null Traditional Rental Income: $3497 Airbnb ROI: N/A Traditional ROI: 3.08%
12825 Sunfish Dr Middlebury, IN Beautiful ranch home located in Middlebury, Indiana's Winding River subdivision. The neigh...	3 beds \| 2 baths \| 1,450 sq.ft.	$345,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.53% Airbnb Rental Income: $null Traditional Rental Income: $2494 Airbnb ROI: N/A Traditional ROI: 5.53%
115 Greenfield Dr Middlebury, IN Sprawling ranch in the highly sought-after Highland Hills neighborhood in Middlebury Schoo...	3 beds \| 2 baths \| 3,304 sq.ft.	$434,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.29% Airbnb Rental Income: $null Traditional Rental Income: $3016 Airbnb ROI: N/A Traditional ROI: 5.29%
12853 King Fish Ct Middlebury, IN *BACK ON MARKET AT NO FAULT OF SELLER * Step into this beautifully refreshed home! The...	3 beds \| 2 baths \| 1,970 sq.ft.	$349,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.37% Airbnb Rental Income: $null Traditional Rental Income: $3074 Airbnb ROI: N/A Traditional ROI: 7.37%
606 Claudia Ln Middlebury, IN Great move-in ready home in Westlake Estates conveniently located near schools and US20! T...	3 beds \| 2 baths \| 1,176 sq.ft.	$279,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.67% Airbnb Rental Income: $null Traditional Rental Income: $2040 Airbnb ROI: N/A Traditional ROI: 5.67%
53339 State Road 13 Middlebury, IN Take a look at his amazing Barndo located just outside of Middlebury on 6+ rolling/wooded ...	4 beds \| 3 baths \| 3,528 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 2% Airbnb Rental Income: $null Traditional Rental Income: $3312 Airbnb ROI: N/A Traditional ROI: 2%
10281 County Road 4 Middlebury, IN Peace is all you will think of at this home. Nestled on 1 acre in the desirable Middlebury...	3 beds \| 1 baths \| 1,990 sq.ft.	$369,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.52% Airbnb Rental Income: $null Traditional Rental Income: $1988 Airbnb ROI: N/A Traditional ROI: 3.52%
1116 Erin Ct Middlebury, IN Middlebury living at it's finest! This gorgeous brick home features 3 bedrooms and 3.5 bat...	4 beds \| 3 baths \| 3,729 sq.ft.	$474,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.26% Airbnb Rental Income: $null Traditional Rental Income: $3423 Airbnb ROI: N/A Traditional ROI: 5.26%
312 Bristol Ave Middlebury, IN 312 Bristol Ave, Middlebury, IN 46540 \| Single Family Residential	4 beds \| 2 baths \| 3,640 sq.ft.	$439,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.34% Airbnb Rental Income: $null Traditional Rental Income: $2230 Airbnb ROI: N/A Traditional ROI: 3.34%
11955 W 710 N Middlebury, IN 11955 W 710 N, Middlebury, IN 46540 \| Single Family Residential	3 beds \| 1 baths \| 1,424 sq.ft.	$280,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.46% Airbnb Rental Income: $null Traditional Rental Income: $1757 Airbnb ROI: N/A Traditional ROI: 4.46%
54420 County Road 33 Rd Middlebury, IN 54420 County Road 33 Rd, Middlebury, IN 46540 \| Single Family Residential	6 beds \| 6 baths \| 12,367 sq.ft.	$4,999,900	Airbnb cash on cash: N/A Traditional cash on cash: -0.4% Airbnb Rental Income: $null Traditional Rental Income: $6808 Airbnb ROI: N/A Traditional ROI: -0.4%
12330 County Road 4 Middlebury, IN 12330 County Road 4, Middlebury, IN 46540 \| Single Family Residential	5 beds \| 3 baths \| 4,832 sq.ft.	$580,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.12% Airbnb Rental Income: $null Traditional Rental Income: $3323 Airbnb ROI: N/A Traditional ROI: 4.12%
57051 County Road 33 Middlebury, IN Here's an opportunity to own a versatile country property featuring two homes, a barn, and...	4 beds \| 2 baths \| 3,052 sq.ft.	$695,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.21% Airbnb Rental Income: $null Traditional Rental Income: $2938 Airbnb ROI: N/A Traditional ROI: 2.21%
13120 Bear Creek Ct Middlebury, IN 13120 Bear Creek Ct, Middlebury, IN 46540 \| Single Family Residential	5 beds \| 3 baths \| 2,584 sq.ft.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.29% Airbnb Rental Income: $null Traditional Rental Income: $3261 Airbnb ROI: N/A Traditional ROI: 4.29%
54725 County Road 33 Middlebury, IN 54725 County Road 33, Middlebury, IN 46540 \| Single Family Residential	5 beds \| 4 baths \| 6,370 sq.ft.	$1,390,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.02% Airbnb Rental Income: $null Traditional Rental Income: $3795 Airbnb ROI: N/A Traditional ROI: 1.02%
411 S Main St Middlebury, IN 411 S Main St, Middlebury, IN 46540 \| Single Family Residential	4 beds \| 1 baths \| 1,656 sq.ft.	$209,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.3% Airbnb Rental Income: $null Traditional Rental Income: $1913 Airbnb ROI: N/A Traditional ROI: 7.3%
313 Bristol Ave Middlebury, IN 313 Bristol Ave, Middlebury, IN 46540 \| Single Family Residential	4 beds \| 1 baths \| 2,256 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.06% Airbnb Rental Income: $null Traditional Rental Income: $1759 Airbnb ROI: N/A Traditional ROI: 4.06%
13283 Cedar Creek Dr Middlebury, IN 13283 Cedar Creek Dr, Middlebury, IN 46540 \| Single Family Residential	5 beds \| 4 baths \| 4,908 sq.ft.	$800,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.07% Airbnb Rental Income: $null Traditional Rental Income: $3754 Airbnb ROI: N/A Traditional ROI: 3.07%
11975 W State Road 120 Rd Middlebury, IN 11975 W W State Road 120 Rd, Middlebury, IN 46540 \| Single Family Residential	3 beds \| 2 baths \| 2,240 sq.ft.	$345,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.71% Airbnb Rental Income: $null Traditional Rental Income: $2541 Airbnb ROI: N/A Traditional ROI: 5.71%
51134 County Road 37 Middlebury, IN 51134 County Road 37, Middlebury, IN 46540 \| Single Family Residential	4 beds \| 2 baths \| 1,566 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.5% Airbnb Rental Income: $null Traditional Rental Income: $2343 Airbnb ROI: N/A Traditional ROI: 3.5%
209 Bristol Ave Middlebury, IN 209 Bristol Ave, Middlebury, IN 46540 \| Single Family Residential	4 beds \| 2 baths \| 2,055 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.54% Airbnb Rental Income: $null Traditional Rental Income: $2459 Airbnb ROI: N/A Traditional ROI: 6.54%
53660 Forest Lakes Dr Middlebury, IN 53660 Forest Lakes Dr, Middlebury, IN 46540 \| Single Family Residential	5 beds \| 3 baths \| 3,333 sq.ft.	$715,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.01% Airbnb Rental Income: $null Traditional Rental Income: $3345 Airbnb ROI: N/A Traditional ROI: 3.01%
54895 Moonfish Ct Middlebury, IN 54895 Moonfish Ct, Middlebury, IN 46540 \| Single Family Residential	4 beds \| 2 baths \| 1,908 sq.ft.	$349,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.37% Airbnb Rental Income: $null Traditional Rental Income: $2803 Airbnb ROI: N/A Traditional ROI: 6.37%
110 N Scott St Middlebury, IN 110 N Scott St, Middlebury, IN 46540 \| Single Family Residential	2 beds \| 2 baths \| 3,848 sq.ft.	$515,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.29% Airbnb Rental Income: $null Traditional Rental Income: $2082 Airbnb ROI: N/A Traditional ROI: 2.29%
12330 County Road 4 St Middlebury, IN 12330 County Road 4 St, Middlebury, IN 46540 \| Single Family Residential	5 beds \| 4 baths \| 4,216 sq.ft.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.02% Airbnb Rental Income: $null Traditional Rental Income: $3778 Airbnb ROI: N/A Traditional ROI: 5.02%
211 Greenfield Dr Middlebury, IN 211 Greenfield Dr, Middlebury, IN 46540 \| Single Family Residential	4 beds \| 3 baths \| 3,841 sq.ft.	$649,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.06% Airbnb Rental Income: $null Traditional Rental Income: $3065 Airbnb ROI: N/A Traditional ROI: 3.06%
217 Greenfield Dr Middlebury, IN 217 Greenfield Dr, Middlebury, IN 46540 \| Single Family Residential	5 beds \| 3 baths \| 3,582 sq.ft.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.05% Airbnb Rental Income: $null Traditional Rental Income: $3284 Airbnb ROI: N/A Traditional ROI: 3.05%
14340 County Road 12 Middlebury, IN 14340 County Road 12, Middlebury, IN 46540 \| Single Family Residential	3 beds \| 1 baths \| 1,791 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.73% Airbnb Rental Income: $null Traditional Rental Income: $1796 Airbnb ROI: N/A Traditional ROI: 3.73%
1006 Hidden Meadow Ln Middlebury, IN 1006 Hidden Meadow Ln, Middlebury, IN 46540 \| Single Family Residential	3 beds \| 3 baths \| 2,864 sq.ft.	$420,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.54% Airbnb Rental Income: $null Traditional Rental Income: $2998 Airbnb ROI: N/A Traditional ROI: 5.54%
55750 County Road 33 Middlebury, IN 55750 County Road 33, Middlebury, IN 46540 \| Single Family Residential	4 beds \| 4 baths \| 3,696 sq.ft.	$700,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $3622 Airbnb ROI: N/A Traditional ROI: 3.56%
12028 CR 18 Middlebury, IN 12028 CR 18, Middlebury, IN 46540 \| Single Family Residential	3 beds \| 2 baths \| 1,594 sq.ft.	$400,000	Airbnb cash on cash: N/A Traditional cash on cash: 4% Airbnb Rental Income: $null Traditional Rental Income: $2284 Airbnb ROI: N/A Traditional ROI: 4%
55755 Little Creek Ln Middlebury, IN 55755 Little Creek Ln, Middlebury, IN 46540 \| Single Family Residential	4 beds \| 3 baths \| 3,575 sq.ft.	$649,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.96% Airbnb Rental Income: $null Traditional Rental Income: $3003 Airbnb ROI: N/A Traditional ROI: 2.96%
14212 County Road 8 Middlebury, IN 14212 County Road 8, Middlebury, IN 46540 \| Single Family Residential	5 beds \| 3 baths \| 4,283 sq.ft.	$925,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.03% Airbnb Rental Income: $null Traditional Rental Income: $3428 Airbnb ROI: N/A Traditional ROI: 2.03%
56360 County Road 33 Middlebury, IN 56360 County Road 33, Middlebury, IN 46540 \| Single Family Residential	3 beds \| 2 baths \| 2,248 sq.ft.	$300,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.48% Airbnb Rental Income: $null Traditional Rental Income: $2444 Airbnb ROI: N/A Traditional ROI: 6.48%
53805 County Road 43 Middlebury, IN 53805 County Road 43, Middlebury, IN 46540 \| Single Family Residential	5 beds \| 2 baths \| 2,736 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.37% Airbnb Rental Income: $null Traditional Rental Income: $2604 Airbnb ROI: N/A Traditional ROI: 6.37%
112 S Main St Middlebury, IN 112 S Main St, Middlebury, IN 46540 \| Single Family Residential	3 beds \| 1 baths \| 2,848 sq.ft.	$274,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.18% Airbnb Rental Income: $null Traditional Rental Income: $1655 Airbnb ROI: N/A Traditional ROI: 4.18%

Your search for investment property begins and ends here

Single Family Homes for Sale in Middlebury, IN

767 Oakleaf Drive

Middlebury, IN

4 beds | 3 baths | 1,842 sq.ft.

$324,990

Airbnb cash on cash: N/A

Traditional cash on cash: 6.12%

Airbnb Rental Income: $null

Traditional Rental Income: $2579

Airbnb ROI: N/A

Traditional ROI: 6.12%

101 Hemsberd St

Middlebury, IN

3 beds | 3 baths | 1,788 sq.ft.

$309,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.47%

Airbnb Rental Income: $null

Traditional Rental Income: $2597

Airbnb ROI: N/A

Traditional ROI: 6.47%

205 Greenfield Dr

Middlebury, IN

6 beds | 4 baths | 6,412 sq.ft.

$1,200,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.41%

Airbnb Rental Income: $null

Traditional Rental Income: $3808

Airbnb ROI: N/A

Traditional ROI: 1.41%

928 S Main St

Middlebury, IN

3 beds | 2 baths | 2,116 sq.ft.

$289,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7.67%

Airbnb Rental Income: $null

Traditional Rental Income: $2565

Airbnb ROI: N/A

Traditional ROI: 7.67%

13889 Adirondack Ct

Middlebury, IN

5 beds | 3 baths | 4,473 sq.ft.

$789,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.08%

Airbnb Rental Income: $null

Traditional Rental Income: $3497

Airbnb ROI: N/A

Traditional ROI: 3.08%

12825 Sunfish Dr

Middlebury, IN

3 beds | 2 baths | 1,450 sq.ft.

$345,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.53%

Airbnb Rental Income: $null

Traditional Rental Income: $2494

Airbnb ROI: N/A

Traditional ROI: 5.53%

115 Greenfield Dr

Middlebury, IN

3 beds | 2 baths | 3,304 sq.ft.

$434,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.29%

Airbnb Rental Income: $null

Traditional Rental Income: $3016

Airbnb ROI: N/A

Traditional ROI: 5.29%

12853 King Fish Ct

Middlebury, IN

3 beds | 2 baths | 1,970 sq.ft.

$349,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.37%

Airbnb Rental Income: $null

Traditional Rental Income: $3074

Airbnb ROI: N/A