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
2009 Skyelar Court HIGHLAND PARK, IL Welcome to effortless luxurious living in Highland Park. This stunning custom contemporar...	4 beds \| 5 baths \| 3,400 sq.ft.	$1,299,000	Airbnb cash on cash: -2.71% Traditional cash on cash: -0.84% Airbnb Rental Income: $1661 Traditional Rental Income: $3454 Airbnb ROI: -2.71% Traditional ROI: -0.84%
1039 Deerfield Place unit: 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.	$495,900	Airbnb cash on cash: -1.24% Traditional cash on cash: 1.4% Airbnb Rental Income: $1678 Traditional Rental Income: $2434 Airbnb ROI: -1.24% Traditional ROI: 1.4%
3464 Old Mill Road HIGHLAND PARK, IL Expanded and renovated in 2008, this two-story prairie-style executive home offers over 9,...	5 beds \| 6 baths \| 5,819 sq.ft.	$1,575,000	Airbnb cash on cash: -2.09% Traditional cash on cash: 2.08% Airbnb Rental Income: $2006 Traditional Rental Income: $7578 Airbnb ROI: -2.09% Traditional ROI: 2.08%
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.	$1,350,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 1.69% Airbnb Rental Income: $1661 Traditional Rental Income: $3904 Airbnb ROI: -0.47% Traditional ROI: 1.69%
1851 Cooper Lane HIGHLAND PARK, IL INTERIOR OF HOME CAN BE SHOWN STARTING 3/3. APPOINTMENT MUST BE CONFIRMED. PLEASE DO NOT C...	3 beds \| 3 baths \| 3,164 sq.ft.	$950,000	Airbnb cash on cash: -1.61% Traditional cash on cash: 1.81% Airbnb Rental Income: $1678 Traditional Rental Income: $4230 Airbnb ROI: -1.61% Traditional ROI: 1.81%
1475 Avignon Court HIGHLAND PARK, IL One of only 67 homes in the community with a wood-burning fireplace, this beautifully upda...	2 beds \| 3 baths \| 1,890 sq.ft.	$414,900	Airbnb cash on cash: -2.84% Traditional cash on cash: 2.51% Airbnb Rental Income: $1338 Traditional Rental Income: $3003 Airbnb ROI: -2.84% Traditional ROI: 2.51%
650 Walnut Street unit: 301 HIGHLAND PARK, IL Introducing the North Shore's most exquisite luxury residences, The Wolbright. Occupancy W...	3 beds \| 4 baths \| 4,105 sq.ft.	$2,840,000	Airbnb cash on cash: -1.45% Traditional cash on cash: -0.59% Airbnb Rental Income: $1678 Traditional Rental Income: $3489 Airbnb ROI: -1.45% Traditional ROI: -0.59%
50 Red Oak Lane HIGHLAND PARK, IL This beautiful spacious home has a great open floorplan and wonderful natural light in eve...	4 beds \| 3 baths \| N/A	$775,000	Airbnb cash on cash: -1.58% Traditional cash on cash: 1.55% Airbnb Rental Income: $1661 Traditional Rental Income: $3454 Airbnb ROI: -1.58% Traditional ROI: 1.55%

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 $775,000 and the average price per square foot is $277. In March 2026, the average monthly cash on cash return in Highland Park is 2.00%. The average monthly rental income in Highland Park is $3,454.

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

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

In 2026, 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 $3,454.

Your search for investment property begins and ends here

Investment Property for Sale in Highland Park, IL

2009 Skyelar Court

HIGHLAND PARK, IL

4 beds | 5 baths | 3,400 sq.ft.

$1,299,000

Airbnb cash on cash: -2.71%

Traditional cash on cash: -0.84%

Airbnb Rental Income: $1661

Traditional Rental Income: $3454

Airbnb ROI: -2.71%

Traditional ROI: -0.84%

1039 Deerfield Place unit: 1039

HIGHLAND PARK, IL

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

$495,900

Airbnb cash on cash: -1.24%

Traditional cash on cash: 1.4%

Airbnb Rental Income: $1678

Traditional Rental Income: $2434

Airbnb ROI: -1.24%

Traditional ROI: 1.4%

3464 Old Mill Road

HIGHLAND PARK, IL

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

$1,575,000

Airbnb cash on cash: -2.09%

Traditional cash on cash: 2.08%

Airbnb Rental Income: $2006

Traditional Rental Income: $7578

Airbnb ROI: -2.09%

Traditional ROI: 2.08%

1672 Huntington Lane

HIGHLAND PARK, IL

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

$1,350,000

Airbnb cash on cash: -0.47%

Traditional cash on cash: 1.69%

Airbnb Rental Income: $1661

Traditional Rental Income: $3904

Airbnb ROI: -0.47%

Traditional ROI: 1.69%

1851 Cooper Lane

HIGHLAND PARK, IL

3 beds | 3 baths | 3,164 sq.ft.

$950,000

Airbnb cash on cash: -1.61%

Traditional cash on cash: 1.81%

Airbnb Rental Income: $1678

Traditional Rental Income: $4230

Airbnb ROI: -1.61%

Traditional ROI: 1.81%

1475 Avignon Court

HIGHLAND PARK, IL

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

$414,900

Airbnb cash on cash: -2.84%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $1338

Traditional Rental Income: $3003

Airbnb ROI: -2.84%

Traditional ROI: 2.51%

650 Walnut Street unit: 301

HIGHLAND PARK, IL

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

$2,840,000

Airbnb cash on cash: -1.45%

Traditional cash on cash: -0.59%

Airbnb Rental Income: $1678

Traditional Rental Income: $3489

Airbnb ROI: -1.45%

Traditional ROI: -0.59%

50 Red Oak Lane

HIGHLAND PARK, IL

4 beds | 3 baths | N/A

$775,000

Airbnb cash on cash: -1.58%

Traditional cash on cash: 1.55%

Airbnb Rental Income: $1661

Traditional Rental Income: $3454

Airbnb ROI: -1.58%