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
3443 43rd Street Highland, IN This inviting 3-bedroom, 2-bathroom ranch offers comfort, space, and charm--perfect for th...	3 beds \| 2 baths \| 2,156 sq.ft.	$279,900	Airbnb cash on cash: -0.58% Traditional cash on cash: 6.6% Airbnb Rental Income: $739 Traditional Rental Income: $2321 Airbnb ROI: -0.58% Traditional ROI: 6.6%
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: 2.75% Traditional cash on cash: 3.32% Airbnb Rental Income: $1687 Traditional Rental Income: $1351 Airbnb ROI: 2.75% Traditional ROI: 3.32%
9210 Woodward Avenue Highland, IN Seller Says: BRING YOUR OFFERS! The main level features 3 bedrooms, 1 bathroom, a bright l...	3 beds \| 1 baths \| 2,052 sq.ft.	$319,500	Airbnb cash on cash: -0.71% Traditional cash on cash: 3.32% Airbnb Rental Income: $739 Traditional Rental Income: $1640 Airbnb ROI: -0.71% Traditional ROI: 3.32%
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.	$185,000	Airbnb cash on cash: 3.81% Traditional cash on cash: 6.53% Airbnb Rental Income: $1687 Traditional Rental Income: $1695 Airbnb ROI: 3.81% Traditional ROI: 6.53%
9331 Wildwood Drive Highland, IN Fresh painted tri level home with 3 bedrooms, 2 & 1/2 baths, 2 car garage and fenced yard....	3 beds \| 3 baths \| 2,028 sq.ft.	$320,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 6.18% Airbnb Rental Income: $739 Traditional Rental Income: $2491 Airbnb ROI: -0.68% Traditional ROI: 6.18%
2303 99th Street Highland, IN Back on the market--no fault of the sellers! This charming single-level townhouse offers a...	2 beds \| 2 baths \| 1,438 sq.ft.	$234,900	Airbnb cash on cash: 3.15% Traditional cash on cash: 5.97% Airbnb Rental Income: $1687 Traditional Rental Income: $1844 Airbnb ROI: 3.15% Traditional ROI: 5.97%
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: 3.83% Traditional cash on cash: 6.04% Airbnb Rental Income: $1948 Traditional Rental Income: $1967 Airbnb ROI: 3.83% Traditional ROI: 6.04%
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.	$220,999	Airbnb cash on cash: 0.02% Traditional cash on cash: 4.5% Airbnb Rental Income: $739 Traditional Rental Income: $1365 Airbnb ROI: 0.02% Traditional ROI: 4.5%
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: -0.68% Traditional cash on cash: 4.35% Airbnb Rental Income: $739 Traditional Rental Income: $1847 Airbnb ROI: -0.68% Traditional ROI: 4.35%
2291 Martha Street #B2 Highland, IN WHOA! Massive price drop - NO BRAINER! What a great location and setting for local shoppin...	2 beds \| 2 baths \| 1,600 sq.ft.	$159,975	Airbnb cash on cash: 2.81% Traditional cash on cash: 4.65% Airbnb Rental Income: $1687 Traditional Rental Income: $1498 Airbnb ROI: 2.81% Traditional ROI: 4.65%
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.	$285,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 5.24% Airbnb Rental Income: $739 Traditional Rental Income: $1963 Airbnb ROI: -0.48% Traditional ROI: 5.24%
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.	$339,900	Airbnb cash on cash: -1.15% Traditional cash on cash: 6.35% Airbnb Rental Income: $739 Traditional Rental Income: $2823 Airbnb ROI: -1.15% Traditional ROI: 6.35%
3128 Eder Street Highland, IN "Beautifully updated 3 bed, 2 bath tri-level in the heart of Highland! Fresh paint through...	3 beds \| 2 baths \| 1,728 sq.ft.	$279,999	Airbnb cash on cash: -0.47% Traditional cash on cash: 5.72% Airbnb Rental Income: $739 Traditional Rental Income: $2061 Airbnb ROI: -0.47% Traditional ROI: 5.72%
8820 St James Place Highland, IN Welcome to 8820 St James Place in Highland, Indiana! This charming 2 bedroom, 1.5 bathroom...	2 beds \| 2 baths \| 1,211 sq.ft.	$229,900	Airbnb cash on cash: 3.16% Traditional cash on cash: 5.33% Airbnb Rental Income: $1687 Traditional Rental Income: $1688 Airbnb ROI: 3.16% Traditional ROI: 5.33%
3318 Strong Street Highland, IN 379,900 or Trade! Don't get stuck owning two homes! This Rare Highland Move Up home is loc...	3 beds \| 3 baths \| 3,428 sq.ft.	$379,990	Airbnb cash on cash: -0.73% Traditional cash on cash: 5.34% Airbnb Rental Income: $739 Traditional Rental Income: $2593 Airbnb ROI: -0.73% Traditional ROI: 5.34%
3637 42nd Drive Highland, IN Discover this move-in ready Tri-Level in the heart of Highland, offering over 2,000 finish...	3 beds \| 2 baths \| 2,033 sq.ft.	$335,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 5.15% Airbnb Rental Income: $739 Traditional Rental Income: $2343 Airbnb ROI: -0.93% Traditional ROI: 5.15%
3134 Lakeside Drive Highland, IN Dive into Luxury Living on a Private Lake This extraordinary lakefront retreat blends eleg...	4 beds \| 4 baths \| 4,202 sq.ft.	$725,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 4.52% Airbnb Rental Income: $1948 Traditional Rental Income: $4395 Airbnb ROI: 0.14% Traditional ROI: 4.52%
3048 Laporte Street Highland, IN Don't miss your chance to own this Highland gem! Perfectly situated on a beautifully lands...	3 beds \| 1 baths \| 1,457 sq.ft.	$279,900	Airbnb cash on cash: -0.58% Traditional cash on cash: 3.72% Airbnb Rental Income: $739 Traditional Rental Income: $1562 Airbnb ROI: -0.58% Traditional ROI: 3.72%
2609 41st Street Highland, IN This beautifully remodeled brick home near Highland Schools is freshly updated and move-in...	3 beds \| 1 baths \| 1,173 sq.ft.	$275,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 3.55% Airbnb Rental Income: $739 Traditional Rental Income: $1486 Airbnb ROI: -0.54% Traditional ROI: 3.55%
9343 Saric Drive Highland, IN Wonderful brick home with HUGE Potential in central Highland!! Possibilities abound with t...	3 beds \| 1 baths \| 1,053 sq.ft.	$229,900	Airbnb cash on cash: -0.43% Traditional cash on cash: 3.9% Airbnb Rental Income: $739 Traditional Rental Income: $1369 Airbnb ROI: -0.43% Traditional ROI: 3.9%
3336 Garfield Avenue Highland, IN Welcome to this charming 2 bedroom, 2 bath ranch that has been lovingly maintained and is ...	2 beds \| 2 baths \| 2,472 sq.ft.	$289,900	Airbnb cash on cash: 2.34% Traditional cash on cash: 5.57% Airbnb Rental Income: $1687 Traditional Rental Income: $2099 Airbnb ROI: 2.34% Traditional ROI: 5.57%
3122 44th Street Highland, IN Tucked away on a peaceful cul-de-sac, this beautifully updated Cape Cod-style home offers ...	4 beds \| 2 baths \| 1,632 sq.ft.	$334,900	Airbnb cash on cash: 2.57% Traditional cash on cash: 4.74% Airbnb Rental Income: $1948 Traditional Rental Income: $2117 Airbnb ROI: 2.57% Traditional ROI: 4.74%
2642 Grand Boulevard Highland, IN Gorgeous renovated home top to bottom! The front door opens up to the Living room complete...	3 beds \| 1 baths \| 825 sq.ft.	$229,700	Airbnb cash on cash: 0.03% Traditional cash on cash: 3.93% Airbnb Rental Income: $739 Traditional Rental Income: $1275 Airbnb ROI: 0.03% Traditional ROI: 3.93%
3101 98th Street Highland, IN 3 bed 1 bath ranch house with a full basement. Fully fenced yard and 2 car detached garage...	3 beds \| 1 baths \| 1,052 sq.ft.	$226,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 4.13% Airbnb Rental Income: $739 Traditional Rental Income: $1397 Airbnb ROI: -0.41% Traditional ROI: 4.13%
3210 O Day Drive Highland, IN Welcome to 3210 Oday Dr. in Highland! This spacious tri-level home offers 5 bedrooms and 2...	5 beds \| 2 baths \| 1,884 sq.ft.	$309,900	Airbnb cash on cash: 3.05% Traditional cash on cash: 6.62% Airbnb Rental Income: $2068 Traditional Rental Income: $2574 Airbnb ROI: 3.05% Traditional ROI: 6.62%
8011 Sycamore Avenue Highland, IN Charming 3-bedroom, 1-bath ranch--perfect for a starter home or downsizing! This cozy prop...	3 beds \| 1 baths \| 957 sq.ft.	$190,000	Airbnb cash on cash: -1.08% Traditional cash on cash: 3.97% Airbnb Rental Income: $739 Traditional Rental Income: $1339 Airbnb ROI: -1.08% Traditional ROI: 3.97%
2116 Briarwood Lane Highland, IN Welcome to easy living in the coveted White Oak Estates of Highland! This beautifully main...	2 beds \| 2 baths \| 1,939 sq.ft.	$349,900	Airbnb cash on cash: 1.01% Traditional cash on cash: 3.96% Airbnb Rental Income: $1687 Traditional Rental Income: $2187 Airbnb ROI: 1.01% Traditional ROI: 3.96%
2649 Georgetowne Drive #B2 Highland, IN Welcome home to this bright and beautifully maintained 2 bedroom, 2 bath second-floor cond...	2 beds \| 2 baths \| 1,264 sq.ft.	$214,900	Airbnb cash on cash: 3.58% Traditional cash on cash: 6.32% Airbnb Rental Income: $1687 Traditional Rental Income: $1775 Airbnb ROI: 3.58% Traditional ROI: 6.32%
2117 Azalea Drive Highland, IN Well-Built One-Owner Home Near Meadows Park in Highland Welcome home to this spacious and...	5 beds \| 2 baths \| 2,428 sq.ft.	$329,900	Airbnb cash on cash: 2.64% Traditional cash on cash: 5.87% Airbnb Rental Income: $2068 Traditional Rental Income: $2535 Airbnb ROI: 2.64% Traditional ROI: 5.87%
3631 Manor Drive Highland, IN This all-brick, 4 bed, 3 bath bi-level offers over 2400 sq. ft. of living space making it ...	4 beds \| 3 baths \| 2,464 sq.ft.	$388,900	Airbnb cash on cash: 1.96% Traditional cash on cash: 5.71% Airbnb Rental Income: $1948 Traditional Rental Income: $2801 Airbnb ROI: 1.96% Traditional ROI: 5.71%
9448 Parkway Drive Highland, IN This is the home you've been searching for! Spacious and beautifully maintained, this rare...	5 beds \| 3 baths \| 2,618 sq.ft.	$405,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 5.6% Airbnb Rental Income: $2068 Traditional Rental Income: $2941 Airbnb ROI: 1.89% Traditional ROI: 5.6%
9624 O Day Drive Highland, IN Welcome home to this well-cared-for property featuring hardwood floors throughout the main...	3 beds \| 2 baths \| 2,128 sq.ft.	$294,900	Airbnb cash on cash: -0.59% Traditional cash on cash: 6.17% Airbnb Rental Income: $739 Traditional Rental Income: $2304 Airbnb ROI: -0.59% Traditional ROI: 6.17%

Real Estate investment in Highland, IN

There are 38 properties for sale in the city of Highland . The median list price in Highland is $285,000 and the average price per square foot is $155. In October 2025, the average monthly cash on cash return in Highland is 6.00%. The average monthly rental income in Highland is $2,061.

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

There are 38 investment properties available for sale in Highland.

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

The ROI for Short-Term is higher than the Long-Term in Highland with average rental income of $739.

Your search for investment property begins and ends here

Investment Property for Sale in Highland, IN

3443 43rd Street

Highland, IN

3 beds | 2 baths | 2,156 sq.ft.

$279,900

Airbnb cash on cash: -0.58%

Traditional cash on cash: 6.6%

Airbnb Rental Income: $739

Traditional Rental Income: $2321

Airbnb ROI: -0.58%

Traditional ROI: 6.6%

2418 Ridge Road

Highland, IN

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

$249,900

Airbnb cash on cash: 2.75%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $1687

Traditional Rental Income: $1351

Airbnb ROI: 2.75%

Traditional ROI: 3.32%

9210 Woodward Avenue

Highland, IN

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

$319,500

Airbnb cash on cash: -0.71%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $739

Traditional Rental Income: $1640

Airbnb ROI: -0.71%

Traditional ROI: 3.32%

2305 Martha Street #D2

Highland, IN

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

$185,000

Airbnb cash on cash: 3.81%

Traditional cash on cash: 6.53%

Airbnb Rental Income: $1687

Traditional Rental Income: $1695

Airbnb ROI: 3.81%

Traditional ROI: 6.53%

9331 Wildwood Drive

Highland, IN

3 beds | 3 baths | 2,028 sq.ft.

$320,000

Airbnb cash on cash: -0.68%

Traditional cash on cash: 6.18%

Airbnb Rental Income: $739

Traditional Rental Income: $2491

Airbnb ROI: -0.68%

Traditional ROI: 6.18%

2303 99th Street

Highland, IN

2 beds | 2 baths | 1,438 sq.ft.

$234,900

Airbnb cash on cash: 3.15%

Traditional cash on cash: 5.97%

Airbnb Rental Income: $1687

Traditional Rental Income: $1844

Airbnb ROI: 3.15%

Traditional ROI: 5.97%

10010 Kennedy Avenue

Highland, IN

4 beds | 2 baths | 1,344 sq.ft.

$255,000

Airbnb cash on cash: 3.83%

Traditional cash on cash: 6.04%

Airbnb Rental Income: $1948

Traditional Rental Income: $1967

Airbnb ROI: 3.83%

Traditional ROI: 6.04%

2841 43rd Street

Highland, IN

3 beds | 1 baths | 988 sq.ft.

$220,999

Airbnb cash on cash: 0.02%

Traditional cash on cash: 4.5%

Airbnb Rental Income: $739

Traditional Rental Income: $1365

Airbnb ROI: 0.02%