Real Estate Investment Properties for Sale in Winchester, IL

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
No properties are listed in Winchester, Illinois at the moment.
Other Investment Properties for Sale in Illinois
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: -0.35% Traditional cash on cash: 5.31% Airbnb Rental Income: $761 Traditional Rental Income: $2121 Airbnb ROI: -0.35% 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: 2.14% Traditional cash on cash: 3.35% Airbnb Rental Income: $1756 Traditional Rental Income: $1632 Airbnb ROI: 2.14% 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: -1.17% Traditional cash on cash: 2.09% Airbnb Rental Income: $1795 Traditional Rental Income: $2573 Airbnb ROI: -1.17% Traditional ROI: 2.09%
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: -4.13% Traditional cash on cash: 2.44% Airbnb Rental Income: $2210 Traditional Rental Income: $4117 Airbnb ROI: -4.13% Traditional ROI: 2.44%
1528 W Monroe St #200 Chicago , IL 1528 W Monroe St #200, Chicago, IL 60607 \| Condo/Coop	3 beds \| 2 baths \| 1,550 sq.ft.	$585,000	Airbnb cash on cash: -1.92% Traditional cash on cash: 0.11% Airbnb Rental Income: $1910 Traditional Rental Income: $2512 Airbnb ROI: -1.92% Traditional ROI: 0.11%
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: 0.6% Traditional cash on cash: 7.88% Airbnb Rental Income: $872 Traditional Rental Income: $2322 Airbnb ROI: 0.6% 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	$304,900	Airbnb cash on cash: 0.36% Traditional cash on cash: 5.98% Airbnb Rental Income: $1139 Traditional Rental Income: $2371 Airbnb ROI: 0.36% Traditional ROI: 5.98%
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: 1.45% Traditional cash on cash: 3.88% Airbnb Rental Income: $1438 Traditional Rental Income: $1877 Airbnb ROI: 1.45% Traditional ROI: 3.88%

Real Estate investment in Winchester, IL

There are 0 properties for sale in the city of Winchester . The median list price in Winchester is $85,950 and the average price per square foot is $65. In October 2025, the average monthly cash on cash return in Winchester is 18.00%. The average monthly rental income in Winchester is $1,847.

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

There are 0 investment properties available for sale in Winchester.

In 2025, the best neighborhood to buy investment property is Winchester.

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

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, IL

Other Investment Properties for Sale in Illinois

Chicago , IL

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

$314,990

Airbnb cash on cash: -0.35%

Traditional cash on cash: 5.31%

Airbnb Rental Income: $761

Traditional Rental Income: $2121

Airbnb ROI: -0.35%

Traditional ROI: 5.31%

Chicago , IL

3 beds | 1 baths | 842 sq.ft.

$315,000

Airbnb cash on cash: 2.14%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $1756

Traditional Rental Income: $1632

Airbnb ROI: 2.14%

Traditional ROI: 3.35%

Chicago , IL

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

$415,000

Airbnb cash on cash: -1.17%

Traditional cash on cash: 2.09%

Airbnb Rental Income: $1795

Traditional Rental Income: $2573

Airbnb ROI: -1.17%

Traditional ROI: 2.09%

Chicago , IL

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

$400,000

Airbnb cash on cash: -4.13%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $2210

Traditional Rental Income: $4117

Airbnb ROI: -4.13%

Traditional ROI: 2.44%

Chicago , IL

3 beds | 2 baths | 1,550 sq.ft.

$585,000

Airbnb cash on cash: -1.92%

Traditional cash on cash: 0.11%

Airbnb Rental Income: $1910

Traditional Rental Income: $2512

Airbnb ROI: -1.92%

Traditional ROI: 0.11%

Chicago , IL

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

$259,900

Airbnb cash on cash: 0.6%

Traditional cash on cash: 7.88%

Airbnb Rental Income: $872

Traditional Rental Income: $2322

Airbnb ROI: 0.6%

Traditional ROI: 7.88%

Chicago , IL

3 beds | 2 baths | N/A

$304,900

Airbnb cash on cash: 0.36%

Traditional cash on cash: 5.98%

Airbnb Rental Income: $1139

Traditional Rental Income: $2371

Airbnb ROI: 0.36%

Traditional ROI: 5.98%

Chicago , IL

3 beds | 2 baths | 1,080 sq.ft.

$379,900

Airbnb cash on cash: 1.45%

Traditional cash on cash: 3.88%

Airbnb Rental Income: $1438

Traditional Rental Income: $1877

Airbnb ROI: 1.45%

Traditional ROI: 3.88%

Real Estate investment in Winchester, IL

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

How many investment properties are available for sale in Winchester?

Which neighborhoods in Winchester to invest in 2025?

Long-Term vs. Short-Term Rentals in Winchester, Illinois: Which will earn the best returns?

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