Real Estate Investment Properties for Sale in Highland, IN

Looking for investment property in Highland, IN with high ROI ?

Explore a variety of short-term homes & houses in Highland, IN. Invest wisely with VRBO & Highland, 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 Highland, IN

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
8816 Woodward Avenue Highland, IN Welcome to this stunning 4 bedroom, 3 bath all-brick ranch in the desirable Brantwood neig...	4 beds \| 3 baths \| 3,130 sq.ft.	$475,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 5.15% Airbnb Rental Income: $1508 Traditional Rental Income: $3145 Airbnb ROI: 0.47% Traditional ROI: 5.15%
10236 Prairie Avenue Highland, IN This move-in-ready ranch offers the ultimate in maintenance-free living. Step inside to fi...	2 beds \| 2 baths \| 1,549 sq.ft.	$290,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 4.94% Airbnb Rental Income: $1720 Traditional Rental Income: $1981 Airbnb ROI: 2.25% Traditional ROI: 4.94%
2418 Ridge Road Highland, IN Perched atop of a hill, this charming 2-bedroom, 1-bath home offers Privacy, comfort and c...	2 beds \| 1 baths \| 1,872 sq.ft.	$249,900	Airbnb cash on cash: 2.87% Traditional cash on cash: 3.32% Airbnb Rental Income: $1720 Traditional Rental Income: $1351 Airbnb ROI: 2.87% Traditional ROI: 3.32%
9328 Cline Avenue Highland, IN Highland - INVESTOR SPECIAL 2.5 ACRES OF 2 CONTIGUOUS PROPERTIES** INCLUDES the Stone ...	3 beds \| 1 baths \| 1,722 sq.ft.	$100,000	Airbnb cash on cash: 3.69% Traditional cash on cash: 11.41% Airbnb Rental Income: $1289 Traditional Rental Income: $1636 Airbnb ROI: 3.69% Traditional ROI: 11.41%
2440 Martha Street Highland, IN Impeccably Renovated Ranch - Move-In Ready!Step into this beautifully updated 3-bedroom ra...	3 beds \| 2 baths \| 2,572 sq.ft.	$328,900	Airbnb cash on cash: 0.68% Traditional cash on cash: 5.39% Airbnb Rental Income: $1289 Traditional Rental Income: $2343 Airbnb ROI: 0.68% Traditional ROI: 5.39%
9210 Woodward Avenue Highland, IN Located in the heart of Highland, this well-kept ranch offers over 2,000 sq ft of finished...	3 beds \| 1 baths \| 2,052 sq.ft.	$324,850	Airbnb cash on cash: 0.78% Traditional cash on cash: 3.25% Airbnb Rental Income: $1289 Traditional Rental Income: $1640 Airbnb ROI: 0.78% Traditional ROI: 3.25%
2305 Martha Street #D2 Highland, IN Welcome home to 2305 Martha St. Unit 2D, a beautifully updated 2-bedroom, 1.5-bath second-...	2 beds \| 2 baths \| 1,270 sq.ft.	$192,500	Airbnb cash on cash: 3.78% Traditional cash on cash: 6.24% Airbnb Rental Income: $1720 Traditional Rental Income: $1695 Airbnb ROI: 3.78% Traditional ROI: 6.24%
3348 Eder Street Highland, IN Your chance to live in Highland at a great price! Check out this well-maintained ranch tha...	3 beds \| 1 baths \| 1,008 sq.ft.	$260,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 3.46% Airbnb Rental Income: $1289 Traditional Rental Income: $1396 Airbnb ROI: 1.38% Traditional ROI: 3.46%
2935 Strong Street Highland, IN Close to expressways, with walking distance to downtown Highland, look no further than thi...	4 beds \| 2 baths \| 1,730 sq.ft.	$279,900	Airbnb cash on cash: 1.78% Traditional cash on cash: 6.08% Airbnb Rental Income: $1508 Traditional Rental Income: $2203 Airbnb ROI: 1.78% Traditional ROI: 6.08%
2303 99th Street Highland, IN This charming single-level townhouse offers an excellent opportunity for homeowners lookin...	2 beds \| 2 baths \| 1,438 sq.ft.	$234,900	Airbnb cash on cash: 3.27% Traditional cash on cash: 5.97% Airbnb Rental Income: $1720 Traditional Rental Income: $1844 Airbnb ROI: 3.27% Traditional ROI: 5.97%
9626 Delaware Place Highland, IN Lovely 3 bedroom 1.5 all brick ranch with a nice heated sunroom addition for year round en...	3 beds \| 2 baths \| 2,782 sq.ft.	$309,900	Airbnb cash on cash: 0.64% Traditional cash on cash: 5.74% Airbnb Rental Income: $1289 Traditional Rental Income: $2372 Airbnb ROI: 0.64% Traditional ROI: 5.74%
3430 43rd Street Highland, IN Charming tri-level in Highland set on an oversized lot! This 4-bedroom, 1.75-bath home has...	4 beds \| 2 baths \| 1,436 sq.ft.	$329,900	Airbnb cash on cash: 1.4% Traditional cash on cash: 4.64% Airbnb Rental Income: $1508 Traditional Rental Income: $2072 Airbnb ROI: 1.4% Traditional ROI: 4.64%
10010 Kennedy Avenue Highland, IN This solid 1940s house has great potential as a single family home. The home features 2 b...	4 beds \| 2 baths \| 1,344 sq.ft.	$255,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 6.04% Airbnb Rental Income: $1508 Traditional Rental Income: $1967 Airbnb ROI: 2.31% Traditional ROI: 6.04%
9027 Hess Drive Highland, IN Welcome to this beautifully updated and freshly painted 3 bedroom (possible 4th) 2 bathroo...	3 beds \| 2 baths \| 2,016 sq.ft.	$314,900	Airbnb cash on cash: 0.36% Traditional cash on cash: 5.13% Airbnb Rental Income: $1289 Traditional Rental Income: $2297 Airbnb ROI: 0.36% Traditional ROI: 5.13%
3620 42nd Place Highland, IN Welcome to this centrally located tri-level home in the heart of Highland, just minutes fr...	3 beds \| 2 baths \| 1,664 sq.ft.	$214,900	Airbnb cash on cash: 1.75% Traditional cash on cash: 7.42% Airbnb Rental Income: $1289 Traditional Rental Income: $2038 Airbnb ROI: 1.75% Traditional ROI: 7.42%
2841 43rd Street Highland, IN This delightful RANCH ON A CRAWL SPACE conveniently located CLOSE TO SCHOOLS,SHOPPING AND ...	3 beds \| 1 baths \| 988 sq.ft.	$229,899	Airbnb cash on cash: 2.09% Traditional cash on cash: 4.29% Airbnb Rental Income: $1289 Traditional Rental Income: $1365 Airbnb ROI: 2.09% Traditional ROI: 4.29%
2262 Ramblewood Drive Highland, IN Gorgeous, MAINTENANCE-FREE townhome in Whispering Oaks! The HOA takes care of all lawn mai...	3 beds \| 2 baths \| 1,400 sq.ft.	$299,999	Airbnb cash on cash: 0.94% Traditional cash on cash: 4.35% Airbnb Rental Income: $1289 Traditional Rental Income: $1847 Airbnb ROI: 0.94% Traditional ROI: 4.35%
3106 Duluth Street Highland, IN Beautiful 3 bedroom Tri-Level Home Nestled in a beautiful, well-kept neighborhood and just...	3 beds \| 1 baths \| 1,267 sq.ft.	$240,000	Airbnb cash on cash: 1.9% Traditional cash on cash: 4.88% Airbnb Rental Income: $1289 Traditional Rental Income: $1561 Airbnb ROI: 1.9% Traditional ROI: 4.88%
2291 Martha Street #B2 Highland, IN What a great location and setting for local shopping + designated garage - Oversized with ...	2 beds \| 1 baths \| 1,600 sq.ft.	$194,925	Airbnb cash on cash: 2.3% Traditional cash on cash: 3.66% Airbnb Rental Income: $1720 Traditional Rental Income: $1498 Airbnb ROI: 2.3% Traditional ROI: 3.66%
3622 Highway Avenue Highland, IN Beautiful cape cod home on Highway Ave. This well cared for 3 bedroom home has large rooms...	3 beds \| 2 baths \| 1,550 sq.ft.	$295,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 5.03% Airbnb Rental Income: $1289 Traditional Rental Income: $1963 Airbnb ROI: 1.15% Traditional ROI: 5.03%
9117 Kennedy Avenue Highland, IN Welcome to this rare opportunity to own a unique 3-bedroom, 2.5-bath, 1.5-story Cape Cod-s...	3 beds \| 3 baths \| 2,632 sq.ft.	$369,900	Airbnb cash on cash: 0.18% Traditional cash on cash: 5.76% Airbnb Rental Income: $1289 Traditional Rental Income: $2823 Airbnb ROI: 0.18% Traditional ROI: 5.76%

Real Estate investment in Highland, IN

There are 28 properties for sale in the city of Highland . The median list price in Highland is $269,950 and the average price per square foot is $164. In September 2025, the average monthly cash on cash return in Highland is 5.00%. The average monthly rental income in Highland is $1,856.

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

There are 28 investment properties available for sale in Highland.

In 2025, the best neighborhood to buy investment property is Highland.

The ROI for Long-Term is higher than the Short-Term in Highland with average rental income of $1,856.

Your search for investment property begins and ends here

Investment Property for Sale in Highland, IN

8816 Woodward Avenue

Highland, IN

4 beds | 3 baths | 3,130 sq.ft.

$475,000

Airbnb cash on cash: 0.47%

Traditional cash on cash: 5.15%

Airbnb Rental Income: $1508

Traditional Rental Income: $3145

Airbnb ROI: 0.47%

Traditional ROI: 5.15%

10236 Prairie Avenue

Highland, IN

2 beds | 2 baths | 1,549 sq.ft.

$290,000

Airbnb cash on cash: 2.25%

Traditional cash on cash: 4.94%

Airbnb Rental Income: $1720

Traditional Rental Income: $1981

Airbnb ROI: 2.25%

Traditional ROI: 4.94%

2418 Ridge Road

Highland, IN

2 beds | 1 baths | 1,872 sq.ft.

$249,900

Airbnb cash on cash: 2.87%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $1720

Traditional Rental Income: $1351

Airbnb ROI: 2.87%

Traditional ROI: 3.32%

9328 Cline Avenue

Highland, IN

3 beds | 1 baths | 1,722 sq.ft.

$100,000

Airbnb cash on cash: 3.69%

Traditional cash on cash: 11.41%

Airbnb Rental Income: $1289

Traditional Rental Income: $1636

Airbnb ROI: 3.69%

Traditional ROI: 11.41%

2440 Martha Street

Highland, IN

3 beds | 2 baths | 2,572 sq.ft.

$328,900

Airbnb cash on cash: 0.68%

Traditional cash on cash: 5.39%

Airbnb Rental Income: $1289

Traditional Rental Income: $2343

Airbnb ROI: 0.68%

Traditional ROI: 5.39%

9210 Woodward Avenue

Highland, IN

3 beds | 1 baths | 2,052 sq.ft.

$324,850

Airbnb cash on cash: 0.78%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $1289

Traditional Rental Income: $1640

Airbnb ROI: 0.78%

Traditional ROI: 3.25%

2305 Martha Street #D2

Highland, IN

2 beds | 2 baths | 1,270 sq.ft.

$192,500

Airbnb cash on cash: 3.78%

Traditional cash on cash: 6.24%

Airbnb Rental Income: $1720

Traditional Rental Income: $1695

Airbnb ROI: 3.78%

Traditional ROI: 6.24%

3348 Eder Street

Highland, IN

3 beds | 1 baths | 1,008 sq.ft.

$260,000

Airbnb cash on cash: 1.38%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $1289

Traditional Rental Income: $1396

Airbnb ROI: 1.38%