Real Estate Investment Properties for Sale in Winfield, IL

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
27W180 Cooley Ave Winfield, IL Now available, a multi-unit property with a great location in desirable Winfield on a corn...	5 beds \| 3 baths \| N/A	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.39% Airbnb Rental Income: $null Traditional Rental Income: $1434 Airbnb ROI: N/A Traditional ROI: -0.39%
0S732 Myrtle Street Winfield, IL Ranch Home- One Level Living- Hardwood Floors- FULLY FENCED Double Lot- quiet dead end str...	4 beds \| 2 baths \| 1,623 sq.ft.	$310,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 5.02% Airbnb Rental Income: $2249 Traditional Rental Income: $2575 Airbnb ROI: 1.96% Traditional ROI: 5.02%
27W225 Ash Ct Winfield, IL Contact Bob Bakas, Listing Agent (630)-534-0722 for a private showing or more information....	3 beds \| 2 baths \| 1,697 sq.ft.	$394,900	Airbnb cash on cash: 0.61% Traditional cash on cash: 3.91% Airbnb Rental Income: $1971 Traditional Rental Income: $2674 Airbnb ROI: 0.61% Traditional ROI: 3.91%
27W073 Jewell Road Winfield, IL January 31st public showing scheduled- feel free to stop by. Beautifully rehabbed 4-bedroo...	3 beds \| 3 baths \| 2,588 sq.ft.	$550,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 1.85% Airbnb Rental Income: $1971 Traditional Rental Income: $2341 Airbnb ROI: 0.13% Traditional ROI: 1.85%
27W084 Fleming Drive Winfield, IL	4 beds \| 3 baths \| 1,992 sq.ft.	$465,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 3.77% Airbnb Rental Income: $2249 Traditional Rental Income: $3042 Airbnb ROI: 0.65% Traditional ROI: 3.77%
0S760 Cleveland St Winfield, IL 0S760 Cleveland St, Winfield, IL 60190 \| Other	N/A beds \| N/A baths \| N/A	$60,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.15% Airbnb Rental Income: $null Traditional Rental Income: $653 Airbnb ROI: N/A Traditional ROI: 6.15%
27W0S Roosevelt Rd Winfield, IL 27W0S Roosevelt Rd, Winfield, IL 60190 \| Other	N/A beds \| N/A baths \| N/A	$30,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.29% Airbnb Rental Income: $null Traditional Rental Income: $558 Airbnb ROI: N/A Traditional ROI: 11.29%
Lot 17,18,19 Roosevelt Rd Winfield, IL Lot 17,18,19 Roosevelt Rd, Winfield, IL 60190 \| Other	N/A beds \| N/A baths \| N/A	$99,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.57% Airbnb Rental Income: $null Traditional Rental Income: $653 Airbnb ROI: N/A Traditional ROI: 2.57%
1N020 Prairie Path Ln Winfield, IL 1N020 Prairie Path Ln, Winfield, IL 60190 \| Townhouse	3 beds \| 2 baths \| 2,363 sq.ft.	$565,000	Airbnb cash on cash: -1.57% Traditional cash on cash: 0.75% Airbnb Rental Income: $1971 Traditional Rental Income: $2674 Airbnb ROI: -1.57% Traditional ROI: 0.75%
27W705 Grasmere Dr #1702 Winfield, IL 27W705 Grasmere Dr #1702, Winfield, IL 60190 \| Condo/Coop	2 beds \| 2 baths \| 1,200 sq.ft.	$275,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 5.3% Airbnb Rental Income: $1579 Traditional Rental Income: $2627 Airbnb ROI: -0.48% Traditional ROI: 5.3%

Real Estate investment in Winfield, IL

There are 15 properties for sale in the city of Winfield . The median list price in Winfield is $335,000 and the average price per square foot is $266. In January 2026, the average monthly cash on cash return in Winfield is 4.00%. The average monthly rental income in Winfield is $1,930.

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

There are 15 investment properties available for sale in Winfield.

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

The ROI for Long-Term is higher than the Short-Term in Winfield with average rental income of $1,930.

Your search for investment property begins and ends here

Investment Property for Sale in Winfield, IL

27W180 Cooley Ave

Winfield, IL

5 beds | 3 baths | N/A

$650,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.39%

Airbnb Rental Income: $null

Traditional Rental Income: $1434

Airbnb ROI: N/A

Traditional ROI: -0.39%

0S732 Myrtle Street

Winfield, IL

4 beds | 2 baths | 1,623 sq.ft.

$310,000

Airbnb cash on cash: 1.96%

Traditional cash on cash: 5.02%

Airbnb Rental Income: $2249

Traditional Rental Income: $2575

Airbnb ROI: 1.96%

Traditional ROI: 5.02%

27W225 Ash Ct

Winfield, IL

3 beds | 2 baths | 1,697 sq.ft.

$394,900

Airbnb cash on cash: 0.61%

Traditional cash on cash: 3.91%

Airbnb Rental Income: $1971

Traditional Rental Income: $2674

Airbnb ROI: 0.61%

Traditional ROI: 3.91%

27W073 Jewell Road

Winfield, IL

3 beds | 3 baths | 2,588 sq.ft.

$550,000

Airbnb cash on cash: 0.13%

Traditional cash on cash: 1.85%

Airbnb Rental Income: $1971

Traditional Rental Income: $2341

Airbnb ROI: 0.13%

Traditional ROI: 1.85%

27W084 Fleming Drive

Winfield, IL

4 beds | 3 baths | 1,992 sq.ft.

$465,000

Airbnb cash on cash: 0.65%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $2249

Traditional Rental Income: $3042

Airbnb ROI: 0.65%

Traditional ROI: 3.77%

0S760 Cleveland St

Winfield, IL

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

$60,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.15%

Airbnb Rental Income: $null

Traditional Rental Income: $653

Airbnb ROI: N/A

Traditional ROI: 6.15%

27W0S Roosevelt Rd

Winfield, IL

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

$30,000

Airbnb cash on cash: N/A

Traditional cash on cash: 11.29%

Airbnb Rental Income: $null

Traditional Rental Income: $558

Airbnb ROI: N/A

Traditional ROI: 11.29%

Lot 17,18,19 Roosevelt Rd

Winfield, IL

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

$99,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.57%

Airbnb Rental Income: $null

Traditional Rental Income: $653

Airbnb ROI: N/A