Real Estate Investment Properties for Sale in Highland, IL

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2131 HILL CREST DR Highland, IL EASY LIVING TUCKED INTO A PRIVATE NEIGHBORHOOD! This full brick backs up to a beautiful h...	2 beds \| 2 baths \| 1,068 sq.ft.	$210,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.27% Airbnb Rental Income: $null Traditional Rental Income: $1249 Airbnb ROI: N/A Traditional ROI: 3.27%
1312 Old Trenton Road Highland, IL Step back in time to when homes were built to last for generations to come! This 1870 Vic...	5 beds \| 3 baths \| 4,732 sq.ft.	$395,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.97% Airbnb Rental Income: $null Traditional Rental Income: $2806 Airbnb ROI: N/A Traditional ROI: 3.97%
4303 STATE ROUTE 160 Highland, IL 4.44 ACRES OF BEAUTIFUL TREES ADJOINING HIGHLAND SILVER LAKE! All brick home, remodeled k...	3 beds \| 3 baths \| 2,708 sq.ft.	$458,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.94% Airbnb Rental Income: $null Traditional Rental Income: $3570 Airbnb ROI: N/A Traditional ROI: 5.94%
120 SUPPIGER Lane #202 Highland, IL EASY AFFORDABLE LIVING! This condo sits on a cul de sac with amenities close by. It has ...	2 beds \| 1 baths \| 754 sq.ft.	$87,500	Airbnb cash on cash: N/A Traditional cash on cash: 9.41% Airbnb Rental Income: $null Traditional Rental Income: $1393 Airbnb ROI: N/A Traditional ROI: 9.41%
613 Washington Street Highland, IL Charming 2-bed, 1-bath home with an oversized detached garage/workshop with loft for more...	2 beds \| 1 baths \| 1,145 sq.ft.	$133,333	Airbnb cash on cash: N/A Traditional cash on cash: 9.98% Airbnb Rental Income: $null Traditional Rental Income: $1514 Airbnb ROI: N/A Traditional ROI: 9.98%
35 Zbinden Lane Highland, IL Location! Location! Location! Close to Korte Rec Center, Glik Park, Walking Trails, School...	3 beds \| 1 baths \| 1,876 sq.ft.	$194,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.83% Airbnb Rental Income: $null Traditional Rental Income: $1652 Airbnb ROI: N/A Traditional ROI: 5.83%
213 Broadway Highland, IL Great investment opportunity right in town! This 5 unit building is very large with 2 of t...	N/A beds \| N/A baths \| 6,519 sq.ft.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.27% Airbnb Rental Income: $null Traditional Rental Income: $1800 Airbnb ROI: N/A Traditional ROI: 0.27%
180 Keeven Drive Highland, IL Welcome Home! You can be all settled into this well-maintained home for the holidays! This...	3 beds \| 2 baths \| 1,152 sq.ft.	$218,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.11% Airbnb Rental Income: $null Traditional Rental Income: $1770 Airbnb ROI: N/A Traditional ROI: 6.11%
340 Nottingham Lane Highland, IL	3 beds \| 2 baths \| 1,454 sq.ft.	$295,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.13% Airbnb Rental Income: $null Traditional Rental Income: $1981 Airbnb ROI: N/A Traditional ROI: 4.13%
316 Madison Street Highland, IL Welcome to this single-family home that can be used for your next home, or an investment o...	2 beds \| 1 baths \| 1,534 sq.ft.	$165,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.18% Airbnb Rental Income: $null Traditional Rental Income: $1534 Airbnb ROI: N/A Traditional ROI: 7.18%
902 Walnut Street Highland, IL Step back in time with this charming early 1900's historic home, featuring 4 bedrooms and ...	4 beds \| 2 baths \| 2,280 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.43% Airbnb Rental Income: $null Traditional Rental Income: $2452 Airbnb ROI: N/A Traditional ROI: 7.43%
12926 Maple Street Highland, IL Time moves a little slower here. This solidly built, all-brick ranch sits on a full acre i...	4 beds \| 2 baths \| 2,129 sq.ft.	$345,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.35% Airbnb Rental Income: $null Traditional Rental Income: $2335 Airbnb ROI: N/A Traditional ROI: 4.35%
910 6th Street Highland, IL Discover the potential in this charming two-story fixer-upper offering 1,365 sq ft of livi...	2 beds \| 1 baths \| 1,365 sq.ft.	$134,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.45% Airbnb Rental Income: $null Traditional Rental Income: $1550 Airbnb ROI: N/A Traditional ROI: 8.45%
20 Pin Oak Drive Highland, IL New Year! New Home! Start out 2026 in this lovely home tucked away on a cul-de-sac. Situat...	3 beds \| 2 baths \| 2,198 sq.ft.	$235,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.94% Airbnb Rental Income: $null Traditional Rental Income: $2273 Airbnb ROI: N/A Traditional ROI: 6.94%
55 Bridgewater Lane #B Highland, IL Enjoy This Excellent Well Maintained Home In A Quiet Established Neighborhood; FEATURING: ...	3 beds \| 3 baths \| 2,125 sq.ft.	$279,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.34% Airbnb Rental Income: $null Traditional Rental Income: $2358 Airbnb ROI: N/A Traditional ROI: 6.34%

Real Estate investment in Highland, IL

There are 25 properties for sale in the city of Highland . The median list price in Highland is $245,000 and the average price per square foot is $114. In December 2025, the average monthly cash on cash return in Highland is 6.00%. The average monthly rental income in Highland is $1,945.

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

There are 25 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 $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Highland, IL

2131 HILL CREST DR

Highland, IL

2 beds | 2 baths | 1,068 sq.ft.

$210,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.27%

Airbnb Rental Income: $null

Traditional Rental Income: $1249

Airbnb ROI: N/A

Traditional ROI: 3.27%

1312 Old Trenton Road

Highland, IL

5 beds | 3 baths | 4,732 sq.ft.

$395,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.97%

Airbnb Rental Income: $null

Traditional Rental Income: $2806

Airbnb ROI: N/A

Traditional ROI: 3.97%

4303 STATE ROUTE 160

Highland, IL

3 beds | 3 baths | 2,708 sq.ft.

$458,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.94%

Airbnb Rental Income: $null

Traditional Rental Income: $3570

Airbnb ROI: N/A

Traditional ROI: 5.94%

120 SUPPIGER Lane #202

Highland, IL

2 beds | 1 baths | 754 sq.ft.

$87,500

Airbnb cash on cash: N/A

Traditional cash on cash: 9.41%

Airbnb Rental Income: $null

Traditional Rental Income: $1393

Airbnb ROI: N/A

Traditional ROI: 9.41%

613 Washington Street

Highland, IL

2 beds | 1 baths | 1,145 sq.ft.

$133,333

Airbnb cash on cash: N/A

Traditional cash on cash: 9.98%

Airbnb Rental Income: $null

Traditional Rental Income: $1514

Airbnb ROI: N/A

Traditional ROI: 9.98%

35 Zbinden Lane

Highland, IL

3 beds | 1 baths | 1,876 sq.ft.

$194,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.83%

Airbnb Rental Income: $null

Traditional Rental Income: $1652

Airbnb ROI: N/A

Traditional ROI: 5.83%

213 Broadway

Highland, IL

N/A beds | N/A baths | 6,519 sq.ft.

$575,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.27%

Airbnb Rental Income: $null

Traditional Rental Income: $1800

Airbnb ROI: N/A

Traditional ROI: 0.27%

180 Keeven Drive

Highland, IL

3 beds | 2 baths | 1,152 sq.ft.

$218,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.11%

Airbnb Rental Income: $null

Traditional Rental Income: $1770

Airbnb ROI: N/A