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%
12804 Spoonbill Court Middlebury, IN OPEN HOUSE SUNDAY August 3rd 12-2pm EST. Agents welcome! This move in ready two story hous...	4 beds \| 3 baths \| 2,303 sq.ft.	$339,000	Airbnb cash on cash: 2.54% Traditional cash on cash: 7.94% Airbnb Rental Income: $1946 Traditional Rental Income: $3155 Airbnb ROI: 2.54% Traditional ROI: 7.94%
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.	$305,000	Airbnb cash on cash: 4.87% Traditional cash on cash: 7.3% Airbnb Rental Income: $2658 Traditional Rental Income: $2724 Airbnb ROI: 4.87% Traditional ROI: 7.3%
312 W Bristol Street Middlebury, IN Nestled on scenic CR 8 near Krider Gardens and the Pumpkinvine Trail, this stunning 4-bedr...	4 beds \| 3 baths \| 3,640 sq.ft.	$455,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 6.33% Airbnb Rental Income: $1946 Traditional Rental Income: $3550 Airbnb ROI: 1.36% Traditional ROI: 6.33%
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.	$374,990	Airbnb cash on cash: 1.81% Traditional cash on cash: 6.12% Airbnb Rental Income: $1946 Traditional Rental Income: $2948 Airbnb ROI: 1.81% Traditional ROI: 6.12%
764 Oakleaf Drive Middlebury, IN New Construction by Fischer Homes in the beautiful Hampton Walk community featuring the Yo...	4 beds \| 3 baths \| 2,256 sq.ft.	$349,990	Airbnb cash on cash: 2.23% Traditional cash on cash: 6.29% Airbnb Rental Income: $1946 Traditional Rental Income: $2765 Airbnb ROI: 2.23% Traditional ROI: 6.29%
13745 Ranier Drive Middlebury, IN Nestled in the highly sought-after "The Summit" neighborhood, this remarkable 4-bedroom, 3...	4 beds \| 3 baths \| 2,788 sq.ft.	$469,900	Airbnb cash on cash: 1.37% Traditional cash on cash: 5.14% Airbnb Rental Income: $1946 Traditional Rental Income: $3093 Airbnb ROI: 1.37% Traditional ROI: 5.14%
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.	$379,990	Airbnb cash on cash: 1.76% Traditional cash on cash: 5.94% Airbnb Rental Income: $1946 Traditional Rental Income: $2923 Airbnb ROI: 1.76% Traditional ROI: 5.94%
778 Oakleaf Drive Middlebury, IN Gorgeous new DaVinci Modern Farmhouse plan by Fischer Homes in beautiful Parkrose featurin...	3 beds \| 2 baths \| 1,756 sq.ft.	$359,990	Airbnb cash on cash: 3.72% Traditional cash on cash: 5.06% Airbnb Rental Income: $2658 Traditional Rental Income: $2479 Airbnb ROI: 3.72% Traditional ROI: 5.06%
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: 1.9% Traditional cash on cash: 3.85% Airbnb Rental Income: $2658 Traditional Rental Income: $3276 Airbnb ROI: 1.9% Traditional ROI: 3.85%
608 Claudia Lane Middlebury, IN Welcome to this beautiful 3 bedroom, 2 bathroom home located in Middlebury schools right o...	3 beds \| 2 baths \| 1,536 sq.ft.	$269,900	Airbnb cash on cash: 4.72% Traditional cash on cash: 6.16% Airbnb Rental Income: $2658 Traditional Rental Income: $2394 Airbnb ROI: 4.72% Traditional ROI: 6.16%
741 Oakleaf Drive Middlebury, IN New construction by Fischer Homes in beautiful Parkrose featuring the Breckenridge floorpl...	4 beds \| 3 baths \| 3,135 sq.ft.	$399,990	Airbnb cash on cash: 1.59% Traditional cash on cash: 6.18% Airbnb Rental Income: $1946 Traditional Rental Income: $3157 Airbnb ROI: 1.59% Traditional ROI: 6.18%
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%
53415 County Road 35 Middlebury, IN EQUISITE!! This sprawling Ranch is pure perfection--custom-built by Barry Yoder So many f...	3 beds \| 3 baths \| 4,060 sq.ft.	$974,900	Airbnb cash on cash: 0.19% Traditional cash on cash: 1.53% Airbnb Rental Income: $2658 Traditional Rental Income: $3237 Airbnb ROI: 0.19% Traditional ROI: 1.53%
54879 Moonfish Court Middlebury, IN Ranch home on a full basement! Located in the Winding River Estates community, this home o...	3 beds \| 2 baths \| 1,336 sq.ft.	$339,900	Airbnb cash on cash: 4.17% Traditional cash on cash: 5.25% Airbnb Rental Income: $2658 Traditional Rental Income: $2371 Airbnb ROI: 4.17% Traditional ROI: 5.25%
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.	$337,000	Airbnb cash on cash: 5.06% Traditional cash on cash: 6.93% Airbnb Rental Income: $2658 Traditional Rental Income: $2618 Airbnb ROI: 5.06% Traditional ROI: 6.93%
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: 4.31% Traditional cash on cash: 4.79% Airbnb Rental Income: $2658 Traditional Rental Income: $2175 Airbnb ROI: 4.31% Traditional ROI: 4.79%
209 River Park Drive Middlebury, IN Maintenance free living in Middlebury! Well maintained one owner condo in the Villas of R...	2 beds \| 2 baths \| 1,675 sq.ft.	$349,900	Airbnb cash on cash: 0.17% Traditional cash on cash: 3.42% Airbnb Rental Income: $1756 Traditional Rental Income: $2342 Airbnb ROI: 0.17% Traditional ROI: 3.42%
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: 1.78% Traditional cash on cash: 6.63% Airbnb Rental Income: $1946 Traditional Rental Income: $3208 Airbnb ROI: 1.78% Traditional ROI: 6.63%
510 Redbud Lane Middlebury, IN This 3-bedroom, 2-bath home offers exceptional potential on nearly half an acre in Middleb...	3 beds \| 2 baths \| 2,557 sq.ft.	$274,900	Airbnb cash on cash: 5.51% Traditional cash on cash: 8.11% Airbnb Rental Income: $2658 Traditional Rental Income: $2700 Airbnb ROI: 5.51% Traditional ROI: 8.11%
12843 Sunfish Drive Middlebury, IN This beautifully maintained 4-bedroom, 3-bath home offers a seamless open-concept layout, ...	4 beds \| 3 baths \| 2,154 sq.ft.	$345,000	Airbnb cash on cash: 2.35% Traditional cash on cash: 7.64% Airbnb Rental Income: $1946 Traditional Rental Income: $3148 Airbnb ROI: 2.35% Traditional ROI: 7.64%
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: 3.34% Traditional cash on cash: 3.24% Airbnb Rental Income: $2658 Traditional Rental Income: $1988 Airbnb ROI: 3.34% Traditional ROI: 3.24%
12885 Winding River Drive Middlebury, IN Nestled on a generous 3/4 acre in the highly sought-after Middlebury School System, this c...	3 beds \| 4 baths \| 2,241 sq.ft.	$374,900	Airbnb cash on cash: 3.73% Traditional cash on cash: 6.83% Airbnb Rental Income: $2658 Traditional Rental Income: $3116 Airbnb ROI: 3.73% Traditional ROI: 6.83%
104 W Spring Street Middlebury, IN Welcome to your dream home in the heart of downtown Middlebury! This super adorable three-...	3 beds \| 1 baths \| 1,579 sq.ft.	$239,900	Airbnb cash on cash: 6.67% Traditional cash on cash: 6.37% Airbnb Rental Income: $2658 Traditional Rental Income: $1957 Airbnb ROI: 6.67% Traditional ROI: 6.37%
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.	$425,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 5.38% Airbnb Rental Income: $2658 Traditional Rental Income: $3046 Airbnb ROI: 2.82% Traditional ROI: 5.38%

Real Estate investment in Middlebury, IN

There are 25 properties for sale in the city of Middlebury . The median list price in Middlebury is $374,900 and the average price per square foot is $142. In September 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 25 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%

12804 Spoonbill Court

Middlebury, IN

4 beds | 3 baths | 2,303 sq.ft.

$339,000

Airbnb cash on cash: 2.54%

Traditional cash on cash: 7.94%

Airbnb Rental Income: $1946

Traditional Rental Income: $3155

Airbnb ROI: 2.54%

Traditional ROI: 7.94%

608 Fieldstone Lane

Middlebury, IN

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

$305,000

Airbnb cash on cash: 4.87%

Traditional cash on cash: 7.3%

Airbnb Rental Income: $2658

Traditional Rental Income: $2724

Airbnb ROI: 4.87%

Traditional ROI: 7.3%

312 W Bristol Street

Middlebury, IN

4 beds | 3 baths | 3,640 sq.ft.

$455,000

Airbnb cash on cash: 1.36%

Traditional cash on cash: 6.33%

Airbnb Rental Income: $1946

Traditional Rental Income: $3550

Airbnb ROI: 1.36%

Traditional ROI: 6.33%

750 Oakleaf Drive

Middlebury, IN

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

$374,990

Airbnb cash on cash: 1.81%

Traditional cash on cash: 6.12%

Airbnb Rental Income: $1946

Traditional Rental Income: $2948

Airbnb ROI: 1.81%

Traditional ROI: 6.12%

764 Oakleaf Drive

Middlebury, IN

4 beds | 3 baths | 2,256 sq.ft.

$349,990

Airbnb cash on cash: 2.23%

Traditional cash on cash: 6.29%

Airbnb Rental Income: $1946

Traditional Rental Income: $2765

Airbnb ROI: 2.23%

Traditional ROI: 6.29%

13745 Ranier Drive

Middlebury, IN

4 beds | 3 baths | 2,788 sq.ft.

$469,900

Airbnb cash on cash: 1.37%

Traditional cash on cash: 5.14%

Airbnb Rental Income: $1946

Traditional Rental Income: $3093

Airbnb ROI: 1.37%

Traditional ROI: 5.14%

792 Oakleaf Drive

Middlebury, IN

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

$379,990

Airbnb cash on cash: 1.76%

Traditional cash on cash: 5.94%

Airbnb Rental Income: $1946

Traditional Rental Income: $2923

Airbnb ROI: 1.76%