Real Estate Investment Properties for Sale in Simpson, IL

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
434 State Hwy 145N Simpson, IL Discover this beautifully remodeled open concept 3 bedroom, 2 bath home located on Highway...	3 beds \| 2 baths \| 1,327 sq.ft.	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.45% Airbnb Rental Income: $null Traditional Rental Income: $1933 Airbnb ROI: N/A Traditional ROI: 7.45%
664 State Hwy145 N Simpson, IL Welcome to a beautiful custom log home set on 40 picturesque acres, offering privacy, rust...	4 beds \| 3 baths \| 1,484 sq.ft.	$535,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 2.65% Airbnb Rental Income: $1609 Traditional Rental Income: $2220 Airbnb ROI: 0.52% Traditional ROI: 2.65%
Investment Properties for Sale in Other Cities of Illinois
13223 S Buffalo Ave Chicago , IL Nicely updated Bungalow with Basement in a Great Location in Hegewisch! Features a sun-fil...	3 beds \| 2 baths \| 1,100 sq.ft.	$199,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 7.5% Airbnb Rental Income: $881 Traditional Rental Income: $1876 Airbnb ROI: 0.45% Traditional ROI: 7.5%
13210 S Carondolet Avenue Chicago , IL Adorable all brick bungalow in the heart of Hegewisch. This classic bungalow has 2 bedroom...	2 beds \| 2 baths \| 1,700 sq.ft.	$239,900	Airbnb cash on cash: -0.37% Traditional cash on cash: 6.85% Airbnb Rental Income: $691 Traditional Rental Income: $2024 Airbnb ROI: -0.37% Traditional ROI: 6.85%
7801 S Ada St Chicago , IL Welcome to this stunning, fully remodeled solid-brick single-family home in Auburn Gresham...	4 beds \| 3 baths \| 1,200 sq.ft.	$240,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 8.19% Airbnb Rental Income: $1185 Traditional Rental Income: $2306 Airbnb ROI: 1.54% Traditional ROI: 8.19%
5918 S Albany Avenue Chicago , IL GREAT OPPORTUNITY TO OWN IN THIS FAST APPRECIATING AREA !!! REAR OF THE LOT !!BRICK SINGLE...	2 beds \| 2 baths \| 832 sq.ft.	$175,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 9.26% Airbnb Rental Income: $1074 Traditional Rental Income: $2024 Airbnb ROI: 1.35% Traditional ROI: 9.26%
5701 N Sheridan Road #3E Chicago , IL Bright, beautifully maintained 1-bedroom with sweeping lake and skyline views in the highl...	1 beds \| 1 baths \| 850 sq.ft.	$199,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 2.3% Airbnb Rental Income: $1452 Traditional Rental Income: $1566 Airbnb ROI: -0.58% Traditional ROI: 2.3%
5130 S Menard Ave Chicago , IL 5130 S Menard Ave, Chicago, IL 60638 \| Single Family Residential	3 beds \| 1 baths \| 945 sq.ft.	$280,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 2.29% Airbnb Rental Income: $1183 Traditional Rental Income: $1551 Airbnb ROI: -0.57% Traditional ROI: 2.29%
5705 S Nottingham Ave Chicago , IL 5705 S Nottingham Ave, Chicago, IL 60638 \| Single Family Residential	2 beds \| 2 baths \| 929 sq.ft.	$429,000	Airbnb cash on cash: -1.87% Traditional cash on cash: 0.95% Airbnb Rental Income: $1004 Traditional Rental Income: $1782 Airbnb ROI: -1.87% Traditional ROI: 0.95%
5728 S Stony Island Ave #2 Chicago , IL 5728 S Stony Island Ave #2, Chicago, IL 60637 \| Condo/Coop	1 beds \| 1 baths \| 900 sq.ft.	$95,000	Airbnb cash on cash: -9.8% Traditional cash on cash: 2% Airbnb Rental Income: $497 Traditional Rental Income: $1318 Airbnb ROI: -9.8% Traditional ROI: 2%
945 E Hyde Park Blvd #2 Chicago , IL Welcome to The Courtyard On The Boulevard. This vintage Hyde Park condominium boasts the l...	2 beds \| 1 baths \| 1,100 sq.ft.	$199,000	Airbnb cash on cash: -4.85% Traditional cash on cash: 1.47% Airbnb Rental Income: $717 Traditional Rental Income: $1603 Airbnb ROI: -4.85% Traditional ROI: 1.47%
5801 S Blackstone Ave Chicago , IL 5801 S Blackstone Ave, Chicago, IL 60637 \| Single Family Residential	5 beds \| 4 baths \| 3,919 sq.ft.	$1,745,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.28% Airbnb Rental Income: $null Traditional Rental Income: $3303 Airbnb ROI: N/A Traditional ROI: -1.28%
1709 NORTH PARK Avenue #1 Chicago , IL This charming vintage-chic condo blends classic character with thoughtful updates in a pri...	2 beds \| 2 baths \| N/A	$575,000	Airbnb cash on cash: -1.4% Traditional cash on cash: 0.88% Airbnb Rental Income: $1635 Traditional Rental Income: $2399 Airbnb ROI: -1.4% Traditional ROI: 0.88%
1905 N Bissell Street #2 Chicago , IL Impeccably designed resale from critically acclaimed PLD Development. This highly upgraded...	3 beds \| 2 baths \| N/A	$950,000	Airbnb cash on cash: -1.93% Traditional cash on cash: 1.7% Airbnb Rental Income: $1458 Traditional Rental Income: $4238 Airbnb ROI: -1.93% Traditional ROI: 1.7%
801 S Plymouth Court #1111 Chicago , IL Rarely available Penthouse unit overlooking Sears Tower (Willis) and downtown Chicago. 2 l...	2 beds \| 2 baths \| 1,300 sq.ft.	$265,000	Airbnb cash on cash: -4.3% Traditional cash on cash: 3.58% Airbnb Rental Income: $1014 Traditional Rental Income: $2626 Airbnb ROI: -4.3% Traditional ROI: 3.58%

Real Estate investment in Simpson, IL

There are 2 properties for sale in the city of Simpson . The median list price in Simpson is $209,950 and the average price per square foot is $138. In May 2026, the average monthly cash on cash return in Simpson is 5.00%. The average monthly rental income in Simpson is $2,077.

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

There are 2 investment properties available for sale in Simpson.

In 2026, the best neighborhood to buy investment property is Simpson.

The ROI for Long-Term is higher than the Short-Term in Simpson with average rental income of $2,077.

Your search for investment property begins and ends here

Investment Property for Sale in Simpson, IL

434 State Hwy 145N

Simpson, IL

3 beds | 2 baths | 1,327 sq.ft.

$199,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7.45%

Airbnb Rental Income: $null

Traditional Rental Income: $1933

Airbnb ROI: N/A

Traditional ROI: 7.45%

664 State Hwy145 N

Simpson, IL

4 beds | 3 baths | 1,484 sq.ft.

$535,000

Airbnb cash on cash: 0.52%

Traditional cash on cash: 2.65%

Airbnb Rental Income: $1609

Traditional Rental Income: $2220

Airbnb ROI: 0.52%

Traditional ROI: 2.65%

Investment Properties for Sale in Other Cities of Illinois

Chicago , IL

3 beds | 2 baths | 1,100 sq.ft.

$199,000

Airbnb cash on cash: 0.45%

Traditional cash on cash: 7.5%

Airbnb Rental Income: $881

Traditional Rental Income: $1876

Airbnb ROI: 0.45%

Traditional ROI: 7.5%

Chicago , IL

2 beds | 2 baths | 1,700 sq.ft.

$239,900

Airbnb cash on cash: -0.37%

Traditional cash on cash: 6.85%

Airbnb Rental Income: $691

Traditional Rental Income: $2024

Airbnb ROI: -0.37%

Traditional ROI: 6.85%

Chicago , IL

4 beds | 3 baths | 1,200 sq.ft.

$240,000

Airbnb cash on cash: 1.54%

Traditional cash on cash: 8.19%

Airbnb Rental Income: $1185

Traditional Rental Income: $2306

Airbnb ROI: 1.54%

Traditional ROI: 8.19%

Chicago , IL

2 beds | 2 baths | 832 sq.ft.

$175,000

Airbnb cash on cash: 1.35%

Traditional cash on cash: 9.26%

Airbnb Rental Income: $1074

Traditional Rental Income: $2024

Airbnb ROI: 1.35%

Traditional ROI: 9.26%

Chicago , IL

1 beds | 1 baths | 850 sq.ft.

$199,000

Airbnb cash on cash: -0.58%

Traditional cash on cash: 2.3%

Airbnb Rental Income: $1452

Traditional Rental Income: $1566

Airbnb ROI: -0.58%

Traditional ROI: 2.3%

Chicago , IL

3 beds | 1 baths | 945 sq.ft.

$280,000

Airbnb cash on cash: -0.57%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $1183

Traditional Rental Income: $1551

Airbnb ROI: -0.57%

Traditional ROI: 2.29%

Chicago , IL

2 beds | 2 baths | 929 sq.ft.

$429,000

Airbnb cash on cash: -1.87%