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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
No properties are listed in Winchester, Illinois at the moment.
Other Investment Properties for Sale in Illinois
4517 N Whipple Street Chicago , IL Stunning 5 bedroom 3.5 bath luxury farmhouse nestled in between the Ravenswood Manor and E...	4 beds \| 4 baths \| N/A	$999,000	Airbnb cash on cash: 1.25% Traditional cash on cash: -0.24% Airbnb Rental Income: $4331 Traditional Rental Income: $2037 Airbnb ROI: 1.25% Traditional ROI: -0.24%
1155 W 111th Street Chicago , IL 2-bedroom, 1-bath half duplex in Morgan Park. This home has a full basement and detached ...	2 beds \| 1 baths \| 1,264 sq.ft.	$170,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.92% Airbnb Rental Income: $null Traditional Rental Income: $1570 Airbnb ROI: N/A Traditional ROI: 6.92%
5737 N Oriole Avenue Chicago , IL Perfect LOCATION! This lovely updated brick home is ideally situated close to exceptional ...	2 beds \| 2 baths \| 1,875 sq.ft.	$440,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 3.95% Airbnb Rental Income: $1741 Traditional Rental Income: $2596 Airbnb ROI: 0.71% Traditional ROI: 3.95%
4836 S Dorchester Avenue Chicago , IL Stunning 3-Flat Georgian Style Multi-Family Building in Hyde Park, where historical elegan...	6 beds \| N/A baths \| N/A	$1,150,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 0.32% Airbnb Rental Income: $7292 Traditional Rental Income: $2659 Airbnb ROI: 3.33% Traditional ROI: 0.32%
1122 W Catalpa Avenue #501 Chicago , IL Beautifully appointed move-in ready corner unit concrete loft drenched in natural light st...	2 beds \| 2 baths \| N/A	$299,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 1.51% Airbnb Rental Income: $2832 Traditional Rental Income: $2382 Airbnb ROI: 0.76% Traditional ROI: 1.51%
5455 N Sheridan Road #1415 Chicago , IL Incredible lake, park and city views from this corner unit 1 bed, 1 bath condo at Edgewate...	1 beds \| 1 baths \| 980 sq.ft.	$214,900	Airbnb cash on cash: 0.62% Traditional cash on cash: 2.44% Airbnb Rental Income: $2248 Traditional Rental Income: $2056 Airbnb ROI: 0.62% Traditional ROI: 2.44%
4848 N Central Ave #301 Chicago , IL 4848 N Central Ave #301, Chicago, IL 60630 \| Condo/Coop	3 beds \| 2 baths \| 1,500 sq.ft.	$395,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 0.83% Airbnb Rental Income: $2437 Traditional Rental Income: $2063 Airbnb ROI: 0.23% Traditional ROI: 0.83%
1711 W Division Street #204 Chicago , IL Impressive, light-filled condo in a boutique elevator building set in the heart of Wicker ...	2 beds \| 2 baths \| 1,750 sq.ft.	$749,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 0.41% Airbnb Rental Income: $3941 Traditional Rental Income: $2848 Airbnb ROI: 0.77% Traditional ROI: 0.41%
1619 N BELL Avenue Chicago , IL Welcome to your new home that embodies the epitome of luxury, located in the vibrant heart...	5 beds \| 4 baths \| 4,350 sq.ft.	$1,899,000	Airbnb cash on cash: 1.05% Traditional cash on cash: -0.21% Airbnb Rental Income: $7817 Traditional Rental Income: $4093 Airbnb ROI: 1.05% Traditional ROI: -0.21%
840 N Lake Shore Drive #1502 Chicago , IL This stunning two-bedroom, two-and-a-half-bath condo in one of Chicago's premier buildings...	2 beds \| 3 baths \| 2,158 sq.ft.	$1,395,000	Airbnb cash on cash: -1.91% Traditional cash on cash: -2.14% Airbnb Rental Income: $5454 Traditional Rental Income: $4062 Airbnb ROI: -1.91% Traditional ROI: -2.14%
1815 N Harding Avenue Chicago , IL BRICK BUNGALOW LOCATED IN QUIET TREE LINED STREET. 3 LEVEL OF LIVING SPACE. ZIP CODE 60647...	4 beds \| 3 baths \| N/A	$519,000	Airbnb cash on cash: 8.95% Traditional cash on cash: 4.9% Airbnb Rental Income: $6798 Traditional Rental Income: $3509 Airbnb ROI: 8.95% Traditional ROI: 4.9%
8246 S Calumet Avenue Chicago , IL Welcome home to this charming two-story brick home in Chicago. This meticulously maintaine...	3 beds \| 2 baths \| 2,091 sq.ft.	$299,000	Airbnb cash on cash: 4.01% Traditional cash on cash: 7.63% Airbnb Rental Income: $2385 Traditional Rental Income: $2818 Airbnb ROI: 4.01% Traditional ROI: 7.63%

Real Estate investment in Winchester, IL

There are 0 properties for sale in the city of Winchester . The median list price in Winchester is $90,000 and the average price per square foot is $49. In December 2024, the average monthly cash on cash return in Winchester is 21.00%. The average monthly rental income in Winchester is $2,081.

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

There are 0 investment properties available for sale in Winchester.

In 2024, 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 | 4 baths | N/A

$999,000

Airbnb cash on cash: 1.25%

Traditional cash on cash: -0.24%

Airbnb Rental Income: $4331

Traditional Rental Income: $2037

Airbnb ROI: 1.25%

Traditional ROI: -0.24%

Chicago , IL

2 beds | 1 baths | 1,264 sq.ft.

$170,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.92%

Airbnb Rental Income: $null

Traditional Rental Income: $1570

Airbnb ROI: N/A

Traditional ROI: 6.92%

Chicago , IL

2 beds | 2 baths | 1,875 sq.ft.

$440,000

Airbnb cash on cash: 0.71%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $1741

Traditional Rental Income: $2596

Airbnb ROI: 0.71%

Traditional ROI: 3.95%

Chicago , IL

6 beds | N/A baths | N/A

$1,150,000

Airbnb cash on cash: 3.33%

Traditional cash on cash: 0.32%

Airbnb Rental Income: $7292

Traditional Rental Income: $2659

Airbnb ROI: 3.33%

Traditional ROI: 0.32%

Chicago , IL

2 beds | 2 baths | N/A

$299,000

Airbnb cash on cash: 0.76%

Traditional cash on cash: 1.51%

Airbnb Rental Income: $2832

Traditional Rental Income: $2382

Airbnb ROI: 0.76%

Traditional ROI: 1.51%

Chicago , IL

1 beds | 1 baths | 980 sq.ft.

$214,900

Airbnb cash on cash: 0.62%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $2248

Traditional Rental Income: $2056

Airbnb ROI: 0.62%

Traditional ROI: 2.44%

Chicago , IL

3 beds | 2 baths | 1,500 sq.ft.

$395,000

Airbnb cash on cash: 0.23%

Traditional cash on cash: 0.83%

Airbnb Rental Income: $2437

Traditional Rental Income: $2063

Airbnb ROI: 0.23%

Traditional ROI: 0.83%

Chicago , IL

2 beds | 2 baths | 1,750 sq.ft.

$749,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 0.41%

Airbnb Rental Income: $3941

Traditional Rental Income: $2848

Airbnb ROI: 0.77%

Traditional ROI: 0.41%

Chicago , IL

5 beds | 4 baths | 4,350 sq.ft.

$1,899,000

Airbnb cash on cash: 1.05%

Traditional cash on cash: -0.21%

Airbnb Rental Income: $7817