Real Estate Investment Properties for Sale in Annapolis, IL

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
20030 N. 475th St. Annapolis, IL This stunning property offers natural beauty of trees & 3 stocked ponds that are manicured...	3 beds \| 3 baths \| 2,894 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.47% Airbnb Rental Income: $null Traditional Rental Income: $3363 Airbnb ROI: N/A Traditional ROI: 3.47%
Investment Properties for Sale in Other Cities of Illinois
4131 W Belmont Avenue #318 Chicago , IL Welcome to Belmont Lofts! This 3rd-floor condo in the vibrant Avondale neighborhood combin...	1 beds \| 1 baths \| 794 sq.ft.	$239,900	Airbnb cash on cash: 0.84% Traditional cash on cash: 4.22% Airbnb Rental Income: $1671 Traditional Rental Income: $1968 Airbnb ROI: 0.84% Traditional ROI: 4.22%
7240 S Oakley Avenue Chicago , IL BRING YOUR CLIENTS! THIS BEAUTHY LOOKS LITTLE BUT IS ENORMOUS! WITH PLANE OF ROOMS IDEAL F...	4 beds \| 2 baths \| 1,016 sq.ft.	$314,990	Airbnb cash on cash: 1.78% Traditional cash on cash: 5.31% Airbnb Rental Income: $1520 Traditional Rental Income: $2121 Airbnb ROI: 1.78% Traditional ROI: 5.31%
1722 N Keeler Avenue Chicago , IL Hot Hermosa location! Updated single family home on a great block. House went through ext...	3 beds \| 1 baths \| 842 sq.ft.	$315,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 3.35% Airbnb Rental Income: $1765 Traditional Rental Income: $1632 Airbnb ROI: 2.17% Traditional ROI: 3.35%
4141 N Kedzie Avenue #307 Chicago , IL Come see this stunning 2 bed / 2 bath condo loaded with upgrades! Step inside to a bright,...	2 beds \| 2 baths \| 1,691 sq.ft.	$415,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 2.09% Airbnb Rental Income: $1948 Traditional Rental Income: $2573 Airbnb ROI: -0.84% Traditional ROI: 2.09%
5151 W Winona Street Chicago , IL Welcome to this exquisite agent-owned residence located in the heart of Jefferson Park. Th...	5 beds \| 3 baths \| N/A	$750,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 2.76% Airbnb Rental Income: $2343 Traditional Rental Income: $3337 Airbnb ROI: 0.5% Traditional ROI: 2.76%
40 E 9th Street #1516 Chicago , IL Discover a unique gem within the South Loop's prominent high-rise community-a stunning thr...	3 beds \| 3 baths \| 2,000 sq.ft.	$400,000	Airbnb cash on cash: -3.49% Traditional cash on cash: 2.44% Airbnb Rental Income: $2495 Traditional Rental Income: $4117 Airbnb ROI: -3.49% Traditional ROI: 2.44%
6929 S Loomis Boulevard Chicago , IL This house has everything your client requested. 5 bedrooms, 3 full bathrooms, Full finis...	4 beds \| 3 baths \| 1,000 sq.ft.	$259,900	Airbnb cash on cash: 2.16% Traditional cash on cash: 7.88% Airbnb Rental Income: $1329 Traditional Rental Income: $2322 Airbnb ROI: 2.16% Traditional ROI: 7.88%
7216 S CENTRAL PARK Avenue Chicago , IL Well-maintained brick ranch in move-in condition! Features gleaming hardwood floors, origi...	3 beds \| 2 baths \| N/A	$315,300	Airbnb cash on cash: 0.3% Traditional cash on cash: 5.75% Airbnb Rental Income: $1133 Traditional Rental Income: $2371 Airbnb ROI: 0.3% Traditional ROI: 5.75%
7205 S HAMLIN Avenue Chicago , IL Maintenance free 4 bedroom ranch with finished basement. 3 bedrooms on the main and one in...	3 beds \| 2 baths \| 1,080 sq.ft.	$379,900	Airbnb cash on cash: 1.79% Traditional cash on cash: 3.88% Airbnb Rental Income: $1585 Traditional Rental Income: $1877 Airbnb ROI: 1.79% Traditional ROI: 3.88%
1620 W Huron Street #1 Chicago , IL All the top end amenities and three outdoor spaces in this first floor 2 bed, 2 bath condo...	2 beds \| 2 baths \| 1,162 sq.ft.	$485,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 2.23% Airbnb Rental Income: $1987 Traditional Rental Income: $2495 Airbnb ROI: -0.04% Traditional ROI: 2.23%
4836 S Dorchester Avenue Chicago , IL Stunning 3-Flat Georgian Style Multi-Family Building in the Hyde Park/Kenwood Community, w...	6 beds \| N/A baths \| N/A	$975,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 0.55% Airbnb Rental Income: $2523 Traditional Rental Income: $2659 Airbnb ROI: -0.27% Traditional ROI: 0.55%

Real Estate investment in Annapolis, IL

There are 1 properties for sale in the city of Annapolis . The median list price in Annapolis is $625,000 and the average price per square foot is $216. In September 2025, the average monthly cash on cash return in Annapolis is 3.00%. The average monthly rental income in Annapolis is $3,363.

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

There are 1 investment properties available for sale in Annapolis.

The ROI for Short-Term is higher than the Long-Term in Annapolis with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Annapolis, IL

20030 N. 475th St.

Annapolis, IL

3 beds | 3 baths | 2,894 sq.ft.

$625,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.47%

Airbnb Rental Income: $null

Traditional Rental Income: $3363

Airbnb ROI: N/A

Traditional ROI: 3.47%

Investment Properties for Sale in Other Cities of Illinois

Chicago , IL

1 beds | 1 baths | 794 sq.ft.

$239,900

Airbnb cash on cash: 0.84%

Traditional cash on cash: 4.22%

Airbnb Rental Income: $1671

Traditional Rental Income: $1968

Airbnb ROI: 0.84%

Traditional ROI: 4.22%

Chicago , IL

4 beds | 2 baths | 1,016 sq.ft.

$314,990

Airbnb cash on cash: 1.78%

Traditional cash on cash: 5.31%

Airbnb Rental Income: $1520

Traditional Rental Income: $2121

Airbnb ROI: 1.78%

Traditional ROI: 5.31%

Chicago , IL

3 beds | 1 baths | 842 sq.ft.

$315,000

Airbnb cash on cash: 2.17%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $1765

Traditional Rental Income: $1632

Airbnb ROI: 2.17%

Traditional ROI: 3.35%

Chicago , IL

2 beds | 2 baths | 1,691 sq.ft.

$415,000

Airbnb cash on cash: -0.84%

Traditional cash on cash: 2.09%

Airbnb Rental Income: $1948

Traditional Rental Income: $2573

Airbnb ROI: -0.84%

Traditional ROI: 2.09%

Chicago , IL

5 beds | 3 baths | N/A

$750,000

Airbnb cash on cash: 0.5%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $2343

Traditional Rental Income: $3337

Airbnb ROI: 0.5%

Traditional ROI: 2.76%

Chicago , IL

3 beds | 3 baths | 2,000 sq.ft.

$400,000

Airbnb cash on cash: -3.49%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $2495

Traditional Rental Income: $4117

Airbnb ROI: -3.49%

Traditional ROI: 2.44%

Chicago , IL

4 beds | 3 baths | 1,000 sq.ft.

$259,900

Airbnb cash on cash: 2.16%

Traditional cash on cash: 7.88%

Airbnb Rental Income: $1329

Traditional Rental Income: $2322

Airbnb ROI: 2.16%

Traditional ROI: 7.88%

Chicago , IL

3 beds | 2 baths | N/A

$315,300

Airbnb cash on cash: 0.3%

Traditional cash on cash: 5.75%