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
Harrison St CHARLESTON, IL Harrison St, CHARLESTON, IL 61912 \| Other	N/A beds \| N/A baths \| N/A	$62,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.31% Airbnb Rental Income: $null Traditional Rental Income: $804 Airbnb ROI: N/A Traditional ROI: 8.31%
21137 E County Road 1050 N CHARLESTON, IL 21137 E County Road 1050 N, CHARLESTON, IL 61912 \| Single Family Residential	4 beds \| 2 baths \| 2,360 sq.ft.	$315,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $2335 Airbnb ROI: N/A Traditional ROI: 4.32%
2236 University Dr CHARLESTON, IL This very beautiful and spacious home sits on a 3/4 acre lot, is heavily insulated with 6&...	3 beds \| 3 baths \| 2,688 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.31% Airbnb Rental Income: $null Traditional Rental Income: $2575 Airbnb ROI: N/A Traditional ROI: 4.31%
12511 Old State Rd CHARLESTON, IL 12511 Old State Rd, CHARLESTON, IL 61920 \| Single Family Residential	4 beds \| 3 baths \| 3,570 sq.ft.	$770,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.48% Airbnb Rental Income: $null Traditional Rental Income: $2777 Airbnb ROI: N/A Traditional ROI: 0.48%
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	$240,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.3% Airbnb Rental Income: $null Traditional Rental Income: $759 Airbnb ROI: N/A Traditional ROI: -0.3%
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%
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%
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.	$279,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.07% Airbnb Rental Income: $null Traditional Rental Income: $1490 Airbnb ROI: N/A Traditional ROI: 2.07%
802 Reynolds Dr CHARLESTON, IL 802 Reynolds Dr, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 2 baths \| 1,267 sq.ft.	$224,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.49% Airbnb Rental Income: $null Traditional Rental Income: $1736 Airbnb ROI: N/A Traditional ROI: 4.49%
802 Van Buren Ave CHARLESTON, IL 802 Van Buren Ave, CHARLESTON, IL 61920 \| Multi Family	N/A beds \| N/A baths \| N/A	$118,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.07% Airbnb Rental Income: $null Traditional Rental Income: $813 Airbnb ROI: N/A Traditional ROI: 3.07%
5911 N County Road 1200e CHARLESTON, IL 5911 N County Road 1200e, CHARLESTON, IL 61920 \| Single Family Residential	4 beds \| 2 baths \| 5,097 sq.ft.	$499,500	Airbnb cash on cash: N/A Traditional cash on cash: 1.43% Airbnb Rental Income: $null Traditional Rental Income: $2280 Airbnb ROI: N/A Traditional ROI: 1.43%
2347 Saratoga Pl CHARLESTON, IL 2347 Saratoga Pl, CHARLESTON, IL 61920 \| Single Family Residential	4 beds \| 3 baths \| 4,274 sq.ft.	$429,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.76% Airbnb Rental Income: $null Traditional Rental Income: $2909 Airbnb ROI: N/A Traditional ROI: 3.76%
59 Kickapoo Valley Dr CHARLESTON, IL 59 Kickapoo Valley Dr, CHARLESTON, IL 61920 \| Single Family Residential	4 beds \| 3 baths \| 3,489 sq.ft.	$700,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.97% Airbnb Rental Income: $null Traditional Rental Income: $2850 Airbnb ROI: N/A Traditional ROI: 0.97%
18973 Harrison Street Rd CHARLESTON, IL 18973 Harrison Street Rd, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 3 baths \| 2,040 sq.ft.	$297,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.67% Airbnb Rental Income: $null Traditional Rental Income: $2586 Airbnb ROI: N/A Traditional ROI: 5.67%
1704 Monroe Ave CHARLESTON, IL 1704 Monroe Ave, CHARLESTON, IL 61920 \| Multi Family	2 beds \| N/A baths \| 1,056 sq.ft.	$94,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.07% Airbnb Rental Income: $null Traditional Rental Income: $950 Airbnb ROI: N/A Traditional ROI: 6.07%
2523 Carriage Ln CHARLESTON, IL 2523 Carriage Ln, CHARLESTON, IL 61920 \| Single Family Residential	5 beds \| 3 baths \| 3,706 sq.ft.	$369,800	Airbnb cash on cash: 1.33% Traditional cash on cash: 5.56% Airbnb Rental Income: $2245 Traditional Rental Income: $3150 Airbnb ROI: 1.33% Traditional ROI: 5.56%
2301 Cortland Dr CHARLESTON, IL 2301 Cortland Dr, CHARLESTON, IL 61920 \| Single Family Residential	6 beds \| 3 baths \| 2,384 sq.ft.	$329,900	Airbnb cash on cash: 1.88% Traditional cash on cash: 5.73% Airbnb Rental Income: $2245 Traditional Rental Income: $2876 Airbnb ROI: 1.88% Traditional ROI: 5.73%
2071 Whetstone Rd CHARLESTON, IL 2071 Whetstone Rd, CHARLESTON, IL 61920 \| Single Family Residential	4 beds \| 3 baths \| 3,323 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.1% Airbnb Rental Income: $null Traditional Rental Income: $2899 Airbnb ROI: N/A Traditional ROI: 0.1%
1819 Reynolds Dr CHARLESTON, IL 1819 Reynolds Dr, CHARLESTON, IL 61920 \| Single Family Residential	5 beds \| 3 baths \| 2,757 sq.ft.	$229,500	Airbnb cash on cash: 4.09% Traditional cash on cash: 10.74% Airbnb Rental Income: $2245 Traditional Rental Income: $3127 Airbnb ROI: 4.09% Traditional ROI: 10.74%
15046 E County Road 600n Rd CHARLESTON, IL 15046 E County Road 600n Rd, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 2 baths \| 2,213 sq.ft.	$329,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.82% Airbnb Rental Income: $null Traditional Rental Income: $2281 Airbnb ROI: N/A Traditional ROI: 3.82%
600 W Monroe Ave CHARLESTON, IL 600 W Monroe Ave, CHARLESTON, IL 61920 \| Single Family Residential	2 beds \| 1 baths \| 1,004 sq.ft.	$86,000	Airbnb cash on cash: 9.84% Traditional cash on cash: 11.22% Airbnb Rental Income: $1655 Traditional Rental Income: $1307 Airbnb ROI: 9.84% Traditional ROI: 11.22%
1811 Madison Ave CHARLESTON, IL 1811 Madison Ave, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 1 baths \| 1,968 sq.ft.	$175,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.1% Airbnb Rental Income: $null Traditional Rental Income: $1646 Airbnb ROI: N/A Traditional ROI: 6.1%
120 Heather Dr CHARLESTON, IL 120 Heather Dr, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 2 baths \| 1,652 sq.ft.	$259,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.4% Airbnb Rental Income: $null Traditional Rental Income: $2212 Airbnb ROI: N/A Traditional ROI: 5.4%
302 N 16th St CHARLESTON, IL 302 N 16th St, CHARLESTON, IL 61920 \| Single Family Residential	2 beds \| 1 baths \| 704 sq.ft.	$87,500	Airbnb cash on cash: 9.62% Traditional cash on cash: 9.64% Airbnb Rental Income: $1655 Traditional Rental Income: $1192 Airbnb ROI: 9.62% Traditional ROI: 9.64%
2314 University Dr CHARLESTON, IL 2314 University Dr, CHARLESTON, IL 61920 \| Single Family Residential	5 beds \| 3 baths \| 3,880 sq.ft.	$589,900	Airbnb cash on cash: -0.37% Traditional cash on cash: 2.21% Airbnb Rental Income: $2245 Traditional Rental Income: $3104 Airbnb ROI: -0.37% Traditional ROI: 2.21%
1 Deerfield Ln CHARLESTON, IL 1 Deerfield Ln, CHARLESTON, IL 61920 \| Single Family Residential	5 beds \| 3 baths \| 3,870 sq.ft.	$420,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 4.41% Airbnb Rental Income: $2245 Traditional Rental Income: $3105 Airbnb ROI: 0.79% Traditional ROI: 4.41%
2346 Saratoga Pl CHARLESTON, IL 2346 Saratoga Pl, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 2 baths \| 3,186 sq.ft.	$312,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.1% Airbnb Rental Income: $null Traditional Rental Income: $1958 Airbnb ROI: N/A Traditional ROI: 3.1%
1018 Westgate Dr CHARLESTON, IL 1018 Westgate Dr, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 1 baths \| 1,452 sq.ft.	$180,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.38% Airbnb Rental Income: $null Traditional Rental Income: $1739 Airbnb ROI: N/A Traditional ROI: 6.38%
19 Miller Ave CHARLESTON, IL 19 Miller Ave, CHARLESTON, IL 61920 \| Single Family Residential	2 beds \| 2 baths \| 1,152 sq.ft.	$150,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 7.18% Airbnb Rental Income: $1655 Traditional Rental Income: $1585 Airbnb ROI: 4.43% Traditional ROI: 7.18%
1117 Polk Ave CHARLESTON, IL 1117 Polk Ave, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 2 baths \| 1,808 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.09% Airbnb Rental Income: $null Traditional Rental Income: $2162 Airbnb ROI: N/A Traditional ROI: 4.09%
505 Ashby Dr CHARLESTON, IL 505 Ashby Dr, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 1 baths \| 1,225 sq.ft.	$154,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.37% Airbnb Rental Income: $null Traditional Rental Income: $1660 Airbnb ROI: N/A Traditional ROI: 7.37%
717 Eastgate Dr CHARLESTON, IL 717 Eastgate Dr, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 1 baths \| 1,056 sq.ft.	$149,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.99% Airbnb Rental Income: $null Traditional Rental Income: $1557 Airbnb ROI: N/A Traditional ROI: 6.99%
1606 10th St CHARLESTON, IL 1606 10th St, CHARLESTON, IL 61920 \| Single Family Residential	2 beds \| 1 baths \| 870 sq.ft.	$89,900	Airbnb cash on cash: 9.3% Traditional cash on cash: 9.84% Airbnb Rental Income: $1655 Traditional Rental Income: $1237 Airbnb ROI: 9.3% Traditional ROI: 9.84%
1917 18th St CHARLESTON, IL 1917 18th St, CHARLESTON, IL 61920 \| Single Family Residential	3 beds \| 2 baths \| 1,563 sq.ft.	$259,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.11% Airbnb Rental Income: $null Traditional Rental Income: $2134 Airbnb ROI: N/A Traditional ROI: 5.11%

Real Estate investment in Charleston, IL

There are 44 properties for sale in the city of Charleston . The median list price in Charleston is $155,907 and the average price per square foot is $61. In August 2026, the average monthly cash on cash return in Charleston is 13.00%. The average monthly rental income in Charleston is $1,060.

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

There are 44 investment properties available for sale in Charleston.

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

The ROI for Short-Term is higher than the Long-Term in Charleston with average rental income of $1,655.

Your search for investment property begins and ends here

Investment Property for Sale in Charleston, IL

Harrison St

CHARLESTON, IL

N/A beds | N/A baths | N/A

$62,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.31%

Airbnb Rental Income: $null

Traditional Rental Income: $804

Airbnb ROI: N/A

Traditional ROI: 8.31%

21137 E County Road 1050 N

CHARLESTON, IL

4 beds | 2 baths | 2,360 sq.ft.

$315,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.32%

Airbnb Rental Income: $null

Traditional Rental Income: $2335

Airbnb ROI: N/A

Traditional ROI: 4.32%

2236 University Dr

CHARLESTON, IL

3 beds | 3 baths | 2,688 sq.ft.

$349,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.31%

Airbnb Rental Income: $null

Traditional Rental Income: $2575

Airbnb ROI: N/A

Traditional ROI: 4.31%

12511 Old State Rd

CHARLESTON, IL

4 beds | 3 baths | 3,570 sq.ft.

$770,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.48%

Airbnb Rental Income: $null

Traditional Rental Income: $2777

Airbnb ROI: N/A

Traditional ROI: 0.48%

9620 N County Road 1300e Rd

CHARLESTON, IL

N/A beds | N/A baths | N/A

$240,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.3%

Airbnb Rental Income: $null

Traditional Rental Income: $759

Airbnb ROI: N/A

Traditional ROI: -0.3%

2102 Whetstone Rd

CHARLESTON, IL

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

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

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