Real Estate Investment Properties for Sale in Highland Park, IL

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2325 Shady Lane HIGHLAND PARK, IL Charming brick bungalow sitting on almost an acre of lush, wooded private property in the ...	3 beds \| 3 baths \| 1,387 sq.ft.	$649,900	Airbnb cash on cash: 0.3% Traditional cash on cash: 2.6% Airbnb Rental Income: $2189 Traditional Rental Income: $3031 Airbnb ROI: 0.3% Traditional ROI: 2.6%
860 Green Bay Road HIGHLAND PARK, IL Welcome to Your Next Dream Home or Investment Opportunity! This stunning, fully rehabbed ...	4 beds \| 4 baths \| 2,400 sq.ft.	$765,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 1.32% Airbnb Rental Income: $2096 Traditional Rental Income: $3260 Airbnb ROI: -1.07% Traditional ROI: 1.32%
650 Walnut Street #301 HIGHLAND PARK, IL Introducing the North Shore's most exquisite luxury residences, The Wolbright. Occupancy ...	3 beds \| 4 baths \| 4,105 sq.ft.	$2,840,000	Airbnb cash on cash: -1.29% Traditional cash on cash: -0.59% Airbnb Rental Income: $2189 Traditional Rental Income: $3489 Airbnb ROI: -1.29% Traditional ROI: -0.59%
1039 Deerfield Place #1039 HIGHLAND PARK, IL Beautiful, recently renovated 3 bedroom and 2 full bathroom condo offering 1850 square fee...	3 beds \| 2 baths \| 1,850 sq.ft.	$449,900	Airbnb cash on cash: -0.25% Traditional cash on cash: 1.65% Airbnb Rental Income: $2189 Traditional Rental Income: $2434 Airbnb ROI: -0.25% Traditional ROI: 1.65%
3464 Old Mill Road HIGHLAND PARK, IL WELCOME TO 3464 OLD MILL ROAD - A MASTERFULLY CRAFTED PRAIRIE-STYLE ESTATE INSPIRED BY FRA...	5 beds \| 6 baths \| 5,819 sq.ft.	$1,599,999	Airbnb cash on cash: -2.18% Traditional cash on cash: 2.03% Airbnb Rental Income: $1803 Traditional Rental Income: $7578 Airbnb ROI: -2.18% Traditional ROI: 2.03%
1672 Huntington Lane HIGHLAND PARK, IL New Construction in Coveted Sherwood Forest - Highland Park, IL. Experience luxury living ...	4 beds \| 4 baths \| 3,216 sq.ft.	$1,399,999	Airbnb cash on cash: -0.21% Traditional cash on cash: 1.59% Airbnb Rental Income: $2096 Traditional Rental Income: $3904 Airbnb ROI: -0.21% Traditional ROI: 1.59%
1490 Avignon Court HIGHLAND PARK, IL Don't miss it! Highly desirable 3 BR, 2.5 bath townhome in beautiful Chantilly. Very well ...	3 beds \| 3 baths \| 1,890 sq.ft.	$395,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 2.02% Airbnb Rental Income: $2189 Traditional Rental Income: $2625 Airbnb ROI: -0.65% Traditional ROI: 2.02%
3175 Applewood Court HIGHLAND PARK, IL Beautifully updated 4 bed 2.1 bath home with fabulous finished basement. Well designed flo...	4 beds \| 3 baths \| 3,100 sq.ft.	$799,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 1.27% Airbnb Rental Income: $2096 Traditional Rental Income: $3156 Airbnb ROI: -0.87% Traditional ROI: 1.27%

Real Estate investment in Highland-park, IL

There are 14 properties for sale in the city of Highland Park . The median list price in Highland Park is $782,000 and the average price per square foot is $280. In October 2025, the average monthly cash on cash return in Highland Park is 2.00%. The average monthly rental income in Highland Park is $3,156.

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

There are 14 investment properties available for sale in Highland-park.

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

The ROI for Long-Term is higher than the Short-Term in Highland-park with average rental income of $3,156.

Your search for investment property begins and ends here

Investment Property for Sale in Highland Park, IL

2325 Shady Lane

HIGHLAND PARK, IL

3 beds | 3 baths | 1,387 sq.ft.

$649,900

Airbnb cash on cash: 0.3%

Traditional cash on cash: 2.6%

Airbnb Rental Income: $2189

Traditional Rental Income: $3031

Airbnb ROI: 0.3%

Traditional ROI: 2.6%

860 Green Bay Road

HIGHLAND PARK, IL

4 beds | 4 baths | 2,400 sq.ft.

$765,000

Airbnb cash on cash: -1.07%

Traditional cash on cash: 1.32%

Airbnb Rental Income: $2096

Traditional Rental Income: $3260

Airbnb ROI: -1.07%

Traditional ROI: 1.32%

650 Walnut Street #301

HIGHLAND PARK, IL

3 beds | 4 baths | 4,105 sq.ft.

$2,840,000

Airbnb cash on cash: -1.29%

Traditional cash on cash: -0.59%

Airbnb Rental Income: $2189

Traditional Rental Income: $3489

Airbnb ROI: -1.29%

Traditional ROI: -0.59%

1039 Deerfield Place #1039

HIGHLAND PARK, IL

3 beds | 2 baths | 1,850 sq.ft.

$449,900

Airbnb cash on cash: -0.25%

Traditional cash on cash: 1.65%

Airbnb Rental Income: $2189

Traditional Rental Income: $2434

Airbnb ROI: -0.25%

Traditional ROI: 1.65%

3464 Old Mill Road

HIGHLAND PARK, IL

5 beds | 6 baths | 5,819 sq.ft.

$1,599,999

Airbnb cash on cash: -2.18%

Traditional cash on cash: 2.03%

Airbnb Rental Income: $1803

Traditional Rental Income: $7578

Airbnb ROI: -2.18%

Traditional ROI: 2.03%

1672 Huntington Lane

HIGHLAND PARK, IL

4 beds | 4 baths | 3,216 sq.ft.

$1,399,999

Airbnb cash on cash: -0.21%

Traditional cash on cash: 1.59%

Airbnb Rental Income: $2096

Traditional Rental Income: $3904

Airbnb ROI: -0.21%

Traditional ROI: 1.59%

1490 Avignon Court

HIGHLAND PARK, IL

3 beds | 3 baths | 1,890 sq.ft.

$395,000

Airbnb cash on cash: -0.65%

Traditional cash on cash: 2.02%

Airbnb Rental Income: $2189

Traditional Rental Income: $2625

Airbnb ROI: -0.65%

Traditional ROI: 2.02%

3175 Applewood Court

HIGHLAND PARK, IL

4 beds | 3 baths | 3,100 sq.ft.

$799,000

Airbnb cash on cash: -0.87%

Traditional cash on cash: 1.27%

Airbnb Rental Income: $2096

Traditional Rental Income: $3156

Airbnb ROI: -0.87%