Real Estate Investment Properties for Sale in Charleston, IL

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
9 Orchard Dr CHARLESTON, IL Seller Financing Available! This 4 Bed 2 Bath Home Has Been Well Maintained. The Very Spac...	4 beds \| 2 baths \| 2,832 sq.ft.	$269,995	Airbnb cash on cash: N/A Traditional cash on cash: 8.54% Airbnb Rental Income: $null Traditional Rental Income: $2825 Airbnb ROI: N/A Traditional ROI: 8.54%
2401 Terrace Ln CHARLESTON, IL 2401 Terrace Ln, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 2 baths \| 1,747 sq.ft.	$205,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.64% Airbnb Rental Income: $null Traditional Rental Income: $2013 Airbnb ROI: N/A Traditional ROI: 6.64%
914 Westgate Dr CHARLESTON, IL 914 Westgate Dr, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 1 baths \| 1,168 sq.ft.	$175,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.22% Airbnb Rental Income: $null Traditional Rental Income: $1500 Airbnb ROI: N/A Traditional ROI: 5.22%
29 Jackson Ave CHARLESTON, IL 29 Jackson Ave, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 1 baths \| 1,176 sq.ft.	$97,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.44% Airbnb Rental Income: $null Traditional Rental Income: $1474 Airbnb ROI: N/A Traditional ROI: 11.44%
2007 Mckinley Ave CHARLESTON, IL 2007 Mckinley Ave, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 2 baths \| 1,672 sq.ft.	$215,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.3% Airbnb Rental Income: $null Traditional Rental Income: $2035 Airbnb ROI: N/A Traditional ROI: 6.3%
2519 Woodlawn Dr CHARLESTON, IL 2519 Woodlawn Dr, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 2 baths \| 1,582 sq.ft.	$214,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.18% Airbnb Rental Income: $null Traditional Rental Income: $2010 Airbnb ROI: N/A Traditional ROI: 6.18%
18 Miller Ave CHARLESTON, IL 18 Miller Ave, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 1 baths \| 1,056 sq.ft.	$149,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.26% Airbnb Rental Income: $null Traditional Rental Income: $1444 Airbnb ROI: N/A Traditional ROI: 6.26%
8 W Harrison Ave CHARLESTON, IL 8 W Harrison Ave, CHARLESTON, IL 61920 \| Single Family Residential	2 beds \| 1 baths \| 1,111 sq.ft.	$78,500	Airbnb cash on cash: 1.12% Traditional cash on cash: 11.89% Airbnb Rental Income: $736 Traditional Rental Income: $1257 Airbnb ROI: 1.12% Traditional ROI: 11.89%
1807 Reynolds Dr CHARLESTON, IL 1807 Reynolds Dr, CHARLESTON, IL 61920 \| Single Family Residential	5 beds \| 3 baths \| 3,346 sq.ft.	$314,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 6.91% Airbnb Rental Income: $1977 Traditional Rental Income: $3091 Airbnb ROI: 1.38% Traditional ROI: 6.91%
12511 Old State Rd CHARLESTON, IL 12511 Old State Rd, CHARLESTON, IL 61920 \| Single Family Residential	4 beds \| 3 baths \| 3,570 sq.ft.	$775,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.46% Airbnb Rental Income: $null Traditional Rental Income: $2777 Airbnb ROI: N/A Traditional ROI: 0.46%
21250 County Highway 17 CHARLESTON, IL 21250 County Highway 17, CHARLESTON, IL 61920 \| Single Family Residential	4 beds \| 2 baths \| 2,100 sq.ft.	$397,500	Airbnb cash on cash: N/A Traditional cash on cash: 2.43% Airbnb Rental Income: $null Traditional Rental Income: $2207 Airbnb ROI: N/A Traditional ROI: 2.43%
2945 Lincoln Highway Rd CHARLESTON, IL 2945 Lincoln Highway Rd, CHARLESTON, IL 61920 \| Single Family Residential	4 beds \| 2 baths \| 2,070 sq.ft.	$419,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.31% Airbnb Rental Income: $null Traditional Rental Income: $1489 Airbnb ROI: N/A Traditional ROI: 0.31%
20315 Airtight Rd CHARLESTON, IL 20315 Airtight Rd, CHARLESTON, IL 61920 \| Single Family Residential	2 beds \| 1 baths \| 1,180 sq.ft.	$340,000	Airbnb cash on cash: -2.2% Traditional cash on cash: -0.2% Airbnb Rental Income: $736 Traditional Rental Income: $1064 Airbnb ROI: -2.2% Traditional ROI: -0.2%
18321 Chief Rd CHARLESTON, IL 18321 Chief Rd, CHARLESTON, IL 61920 \| Single Family Residential	4 beds \| 3 baths \| 2,500 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.68% Airbnb Rental Income: $null Traditional Rental Income: $1489 Airbnb ROI: N/A Traditional ROI: 2.68%
18421 Chief Rd CHARLESTON, IL 18421 Chief Rd, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 3 baths \| 3,490 sq.ft.	$544,500	Airbnb cash on cash: N/A Traditional cash on cash: 1.4% Airbnb Rental Income: $null Traditional Rental Income: $2459 Airbnb ROI: N/A Traditional ROI: 1.4%
29 Miller Ave CHARLESTON, IL 29 Miller Ave, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 1 baths \| 1,185 sq.ft.	$185,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.02% Airbnb Rental Income: $null Traditional Rental Income: $1544 Airbnb ROI: N/A Traditional ROI: 5.02%
109 N 12th St CHARLESTON, IL 109 N 12th St, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 1 baths \| 1,134 sq.ft.	$111,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.47% Airbnb Rental Income: $null Traditional Rental Income: $1454 Airbnb ROI: N/A Traditional ROI: 9.47%
3494 Lincoln Highway Rd CHARLESTON, IL 3494 Lincoln Highway Rd, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 2 baths \| 1,579 sq.ft.	$270,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.21% Airbnb Rental Income: $null Traditional Rental Income: $1989 Airbnb ROI: N/A Traditional ROI: 4.21%
6 Brosam Dr CHARLESTON, IL 6 Brosam Dr, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 2 baths \| 1,728 sq.ft.	$168,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.03% Airbnb Rental Income: $null Traditional Rental Income: $2055 Airbnb ROI: N/A Traditional ROI: 9.03%
2389 Lincoln Highway Rd CHARLESTON, IL 2389 Lincoln Highway Rd, CHARLESTON, IL 61920 \| Single Family Residential	4 beds \| 3 baths \| 3,406 sq.ft.	$849,500	Airbnb cash on cash: N/A Traditional cash on cash: 0.14% Airbnb Rental Income: $null Traditional Rental Income: $2782 Airbnb ROI: N/A Traditional ROI: 0.14%
929 Reynolds Dr CHARLESTON, IL 929 Reynolds Dr, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 1 baths \| 984 sq.ft.	$172,300	Airbnb cash on cash: N/A Traditional cash on cash: 4.74% Airbnb Rental Income: $null Traditional Rental Income: $1400 Airbnb ROI: N/A Traditional ROI: 4.74%
942 E St CHARLESTON, IL 942 E St, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 2 baths \| 2,000 sq.ft.	$147,500	Airbnb cash on cash: N/A Traditional cash on cash: 11.13% Airbnb Rental Income: $null Traditional Rental Income: $2118 Airbnb ROI: N/A Traditional ROI: 11.13%
1103 & 1105 6th St CHARLESTON, IL 1103 & 1105 6th St, CHARLESTON, IL 61920 \| Multi Family	N/A beds \| N/A baths \| 0 sq.ft.	$160,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.92% Airbnb Rental Income: $null Traditional Rental Income: $725 Airbnb ROI: N/A Traditional ROI: 0.92%
9620 N County Road 1300e Rd CHARLESTON, IL 9620 N County Road 1300e Rd, CHARLESTON, IL 61920 \| Other	N/A beds \| N/A baths \| N/A	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.67% Airbnb Rental Income: $null Traditional Rental Income: $759 Airbnb ROI: N/A Traditional ROI: -0.67%
2102 Whetstone Rd CHARLESTON, IL 2102 Whetstone Rd, CHARLESTON, IL 61920 \| Other	N/A beds \| N/A baths \| N/A	$89,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.39% Airbnb Rental Income: $null Traditional Rental Income: $759 Airbnb ROI: N/A Traditional ROI: 4.39%
Buxton Wood Dr CHARLESTON, IL Buxton Wood Dr, CHARLESTON, IL 61920 \| Other	N/A beds \| N/A baths \| N/A	$215,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.04% Airbnb Rental Income: $null Traditional Rental Income: $759 Airbnb ROI: N/A Traditional ROI: 0.04%
Fairfax Ln CHARLESTON, IL Fairfax Ln, CHARLESTON, IL 61920 \| Other	N/A beds \| N/A baths \| N/A	$79,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.3% Airbnb Rental Income: $null Traditional Rental Income: $759 Airbnb ROI: N/A Traditional ROI: 5.3%
747 W State St CHARLESTON, IL 747 W State St, CHARLESTON, IL 61920 \| Other	N/A beds \| N/A baths \| N/A	$49,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.98% Airbnb Rental Income: $null Traditional Rental Income: $759 Airbnb ROI: N/A Traditional ROI: 9.98%
Hawthorne Dr CHARLESTON, IL Hawthorne Dr, CHARLESTON, IL 61920 \| Other	N/A beds \| N/A baths \| N/A	$289,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.79% Airbnb Rental Income: $null Traditional Rental Income: $759 Airbnb ROI: N/A Traditional ROI: -0.79%
East Rt 16 CHARLESTON, IL East Rt 16, CHARLESTON, IL 61920 \| Other	N/A beds \| N/A baths \| N/A	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.46% Airbnb Rental Income: $null Traditional Rental Income: $759 Airbnb ROI: N/A Traditional ROI: -2.46%
Douglas St CHARLESTON, IL Douglas St, CHARLESTON, IL 61920 \| Other	N/A beds \| N/A baths \| N/A	$264,900	Airbnb cash on cash: N/A Traditional cash on cash: -0.57% Airbnb Rental Income: $null Traditional Rental Income: $759 Airbnb ROI: N/A Traditional ROI: -0.57%
749 W State St CHARLESTON, IL 749 W State St, CHARLESTON, IL 61920 \| Other	N/A beds \| N/A baths \| N/A	$99,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.66% Airbnb Rental Income: $null Traditional Rental Income: $759 Airbnb ROI: N/A Traditional ROI: 3.66%
Lot #14 Forest Hills Dr CHARLESTON, IL Lot #14 Forest Hills Dr, CHARLESTON, IL 61920 \| Other	N/A beds \| N/A baths \| N/A	$65,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.12% Airbnb Rental Income: $null Traditional Rental Income: $759 Airbnb ROI: N/A Traditional ROI: 7.12%
1057 7th St CHARLESTON, IL 1057 7th St, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 1 baths \| 1,352 sq.ft.	$167,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.18% Airbnb Rental Income: $null Traditional Rental Income: $1599 Airbnb ROI: N/A Traditional ROI: 6.18%
2644 N County Road 1800 Rd E CHARLESTON, IL 2644 N County Road 1800 Rd E, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 1 baths \| 1,996 sq.ft.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.72% Airbnb Rental Income: $null Traditional Rental Income: $1490 Airbnb ROI: N/A Traditional ROI: 1.72%
1422 Madison Ave CHARLESTON, IL 1422 Madison Ave, CHARLESTON, IL 61920 \| Single Family Residential	2 beds \| 1 baths \| 980 sq.ft.	$79,500	Airbnb cash on cash: 1.07% Traditional cash on cash: 10.56% Airbnb Rental Income: $736 Traditional Rental Income: $1167 Airbnb ROI: 1.07% Traditional ROI: 10.56%
1832 Ashby Dr CHARLESTON, IL 1832 Ashby Dr, CHARLESTON, IL 61920 \| Single Family Residential	4 beds \| 2 baths \| 1,965 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.66% Airbnb Rental Income: $null Traditional Rental Income: $2193 Airbnb ROI: N/A Traditional ROI: 5.66%

Real Estate investment in Charleston, IL

There are 37 properties for sale in the city of Charleston . The median list price in Charleston is $349,000 and the average price per square foot is $155. In January 2026, the average monthly cash on cash return in Charleston is 13.00%. The average monthly rental income in Charleston is $767.

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

There are 37 investment properties available for sale in Charleston.

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

The ROI for Long-Term is higher than the Short-Term in Charleston with average rental income of $767.

Your search for investment property begins and ends here

Investment Property for Sale in Charleston, IL

9 Orchard Dr

CHARLESTON, IL

4 beds | 2 baths | 2,832 sq.ft.

$269,995

Airbnb cash on cash: N/A

Traditional cash on cash: 8.54%

Airbnb Rental Income: $null

Traditional Rental Income: $2825

Airbnb ROI: N/A

Traditional ROI: 8.54%

2401 Terrace Ln

CHARLESTON, IL

3 beds | 2 baths | 1,747 sq.ft.

$205,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.64%

Airbnb Rental Income: $null

Traditional Rental Income: $2013

Airbnb ROI: N/A

Traditional ROI: 6.64%

914 Westgate Dr

CHARLESTON, IL

3 beds | 1 baths | 1,168 sq.ft.

$175,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.22%

Airbnb Rental Income: $null

Traditional Rental Income: $1500

Airbnb ROI: N/A

Traditional ROI: 5.22%

29 Jackson Ave

CHARLESTON, IL

3 beds | 1 baths | 1,176 sq.ft.

$97,000

Airbnb cash on cash: N/A

Traditional cash on cash: 11.44%

Airbnb Rental Income: $null

Traditional Rental Income: $1474

Airbnb ROI: N/A

Traditional ROI: 11.44%

2007 Mckinley Ave

CHARLESTON, IL

3 beds | 2 baths | 1,672 sq.ft.

$215,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.3%

Airbnb Rental Income: $null

Traditional Rental Income: $2035

Airbnb ROI: N/A

Traditional ROI: 6.3%

2519 Woodlawn Dr

CHARLESTON, IL

3 beds | 2 baths | 1,582 sq.ft.

$214,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.18%

Airbnb Rental Income: $null

Traditional Rental Income: $2010

Airbnb ROI: N/A

Traditional ROI: 6.18%

18 Miller Ave

CHARLESTON, IL

3 beds | 1 baths | 1,056 sq.ft.

$149,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.26%

Airbnb Rental Income: $null

Traditional Rental Income: $1444

Airbnb ROI: N/A

Traditional ROI: 6.26%

8 W Harrison Ave

CHARLESTON, IL

2 beds | 1 baths | 1,111 sq.ft.

$78,500

Airbnb cash on cash: 1.12%

Traditional cash on cash: 11.89%

Airbnb Rental Income: $736

Traditional Rental Income: $1257

Airbnb ROI: 1.12%