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
27W303 Chartwell Dr Winfield, IL Custom Built Sieffert Home Close to EVERYTHING! 4 Bedrooms + 3 Full & 1 Half Bathrooms + D...	4 beds \| 3 baths \| 2,292 sq.ft.	$569,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 3% Airbnb Rental Income: $2763 Traditional Rental Income: $3138 Airbnb ROI: 1.08% Traditional ROI: 3%
27W119 Cooley Ave Winfield, IL Experience peaceful living in this spacious half-duplex, perfectly suited for those seekin...	3 beds \| 1 baths \| 1,446 sq.ft.	$315,000	Airbnb cash on cash: 5.5% Traditional cash on cash: 4.41% Airbnb Rental Income: $3195 Traditional Rental Income: $2151 Airbnb ROI: 5.5% Traditional ROI: 4.41%
26W473 Parkway Dr Winfield, IL WonWonderful location. Wheaton Schools! Updated 3 - 4 Bedroom, 2 Bathroom home. Welcoming...	3 beds \| 2 baths \| 1,985 sq.ft.	$475,000	Airbnb cash on cash: 3% Traditional cash on cash: 3.76% Airbnb Rental Income: $3195 Traditional Rental Income: $2810 Airbnb ROI: 3% Traditional ROI: 3.76%
0S461 Madison St Winfield, IL Welcome to this beautifully maintained and thoughtfully updated 4-bedroom, 2.5-bath home o...	4 beds \| 2 baths \| 2,809 sq.ft.	$724,900	Airbnb cash on cash: 0.13% Traditional cash on cash: 1.31% Airbnb Rental Income: $2763 Traditional Rental Income: $2908 Airbnb ROI: 0.13% Traditional ROI: 1.31%
27W225 Ash Ct Winfield, IL Welcome home to this warm and inviting townhome nestled in the charming community of Winfi...	3 beds \| 2 baths \| 1,697 sq.ft.	$370,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 3.12% Airbnb Rental Income: $3195 Traditional Rental Income: $2624 Airbnb ROI: 2.69% Traditional ROI: 3.12%
0S415 Madison St Winfield, IL Stunning Curb Appeal and Inviting Front Porch Welcomes you to this Beautiful Home. Hardwoo...	4 beds \| 2 baths \| 2,868 sq.ft.	$689,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 1.51% Airbnb Rental Income: $2763 Traditional Rental Income: $2865 Airbnb ROI: 0.34% Traditional ROI: 1.51%
27W084 Fleming Dr Winfield, IL	4 beds \| 2 baths \| 1,992 sq.ft.	$465,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 3.77% Airbnb Rental Income: $2763 Traditional Rental Income: $3042 Airbnb ROI: 1.64% Traditional ROI: 3.77%
0S760 Cleveland St Winfield, IL 0S760 Cleveland St, Winfield, IL 60190 \| Other	N/A beds \| N/A baths \| N/A	$52,500	Airbnb cash on cash: N/A Traditional cash on cash: 7.39% Airbnb Rental Income: $null Traditional Rental Income: $653 Airbnb ROI: N/A Traditional ROI: 7.39%
0S775 Madison St Winfield, IL	5 beds \| 3 baths \| 4,000 sq.ft.	$750,000	Airbnb cash on cash: 2.83% Traditional cash on cash: 2.82% Airbnb Rental Income: $5041 Traditional Rental Income: $4002 Airbnb ROI: 2.83% Traditional ROI: 2.82%
0N421 Winfield Scott Dr Winfield, IL 0N421 Winfield Scott Dr, Winfield, IL 60190 \| Single Family Residential	4 beds \| 2 baths \| 2,276 sq.ft.	$599,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 0.95% Airbnb Rental Income: $2763 Traditional Rental Income: $2442 Airbnb ROI: 0.36% Traditional ROI: 0.95%
1N487 Seminole Ln Winfield, IL Beautiful semi-custom home ideally situated with a spacious lot in the sought after Klein ...	4 beds \| 2 baths \| 2,771 sq.ft.	$869,900	Airbnb cash on cash: -0.09% Traditional cash on cash: 1.68% Airbnb Rental Income: $2763 Traditional Rental Income: $3547 Airbnb ROI: -0.09% Traditional ROI: 1.68%
N350 County Farm Rd Winfield, IL N350 County Farm Rd, Winfield, IL 60190 \| Single Family Residential	5 beds \| 1 baths \| 2,000 sq.ft.	$374,000	Airbnb cash on cash: 7.92% Traditional cash on cash: 1.34% Airbnb Rental Income: $5041 Traditional Rental Income: $1702 Airbnb ROI: 7.92% Traditional ROI: 1.34%
0N462 Arbor Ct Winfield, IL 0N462 Arbor Ct, Winfield, IL 60190 \| Single Family Residential	4 beds \| 2 baths \| 3,495 sq.ft.	$859,900	Airbnb cash on cash: -0.73% Traditional cash on cash: -0.49% Airbnb Rental Income: $2763 Traditional Rental Income: $2308 Airbnb ROI: -0.73% Traditional ROI: -0.49%
26W373 Churchill Rd Winfield, IL Welcome to 26W373 Churchill, a renovated home offering 3,900 square feet of beautifully fi...	5 beds \| 2 baths \| 3,904 sq.ft.	$995,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 1.88% Airbnb Rental Income: $5041 Traditional Rental Income: $4167 Airbnb ROI: 1.71% Traditional ROI: 1.88%
0N069 Windermere Rd #2305 Winfield, IL This is where location, convenience and affordability all meet! 2 bedroom, 2 bath, den wit...	2 beds \| 2 baths \| 1,406 sq.ft.	$284,900	Airbnb cash on cash: 1.08% Traditional cash on cash: 4.52% Airbnb Rental Income: $1983 Traditional Rental Income: $2387 Airbnb ROI: 1.08% Traditional ROI: 4.52%
0N080 Vermont Ct Winfield, IL 0N080 Vermont Ct, Winfield, IL 60190 \| Townhouse	2 beds \| 2 baths \| 1,881 sq.ft.	$374,900	Airbnb cash on cash: -0.41% Traditional cash on cash: 2.17% Airbnb Rental Income: $1983 Traditional Rental Income: $2370 Airbnb ROI: -0.41% Traditional ROI: 2.17%
27W168 Chartwell Dr Winfield, IL Welcome to this wonderful Fredericksburg Farm neighborhood. This home is located on a cul-...	4 beds \| 2 baths \| 2,364 sq.ft.	$569,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 1.24% Airbnb Rental Income: $2763 Traditional Rental Income: $2453 Airbnb ROI: 0.6% Traditional ROI: 1.24%
0S099 Lee Ct #101 Winfield, IL 0S099 Lee Ct #101, Winfield, IL 60190 \| Condo/Coop	2 beds \| 2 baths \| 1,242 sq.ft.	$305,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 0.89% Airbnb Rental Income: $1983 Traditional Rental Income: $1804 Airbnb ROI: -0.29% Traditional ROI: 0.89%
27W194 Emerson Ct Winfield, IL 27W194 Emerson Ct, Winfield, IL 60190 \| Townhouse	2 beds \| 1 baths \| 1,824 sq.ft.	$339,000	Airbnb cash on cash: -0.14% Traditional cash on cash: -1.07% Airbnb Rental Income: $1983 Traditional Rental Income: $1166 Airbnb ROI: -0.14% Traditional ROI: -1.07%
27W327 Providence Ln Winfield, IL 27W327 Providence Ln, Winfield, IL 60190 \| Townhouse	3 beds \| 1 baths \| 1,260 sq.ft.	$305,000	Airbnb cash on cash: 4.16% Traditional cash on cash: 1.03% Airbnb Rental Income: $3195 Traditional Rental Income: $1575 Airbnb ROI: 4.16% Traditional ROI: 1.03%
S758 Grant St Winfield, IL S758 Grant St, Winfield, IL 60190 \| Single Family Residential	4 beds \| 2 baths \| 1,603 sq.ft.	$539,999	Airbnb cash on cash: 0.75% Traditional cash on cash: 0.84% Airbnb Rental Income: $2763 Traditional Rental Income: $2156 Airbnb ROI: 0.75% Traditional ROI: 0.84%
27W390 Waterford Dr Winfield, IL 27W390 Waterford Dr, Winfield, IL 60190 \| Single Family Residential	4 beds \| 2 baths \| 2,341 sq.ft.	$605,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 0.94% Airbnb Rental Income: $2763 Traditional Rental Income: $2461 Airbnb ROI: 0.33% Traditional ROI: 0.94%
26W482 Blair St Winfield, IL 26W482 Blair St, Winfield, IL 60190 \| Single Family Residential	3 beds \| 1 baths \| 1,988 sq.ft.	$300,000	Airbnb cash on cash: 5.19% Traditional cash on cash: 1.94% Airbnb Rental Income: $3195 Traditional Rental Income: $1557 Airbnb ROI: 5.19% Traditional ROI: 1.94%
0S630 Madison St Winfield, IL 0S630 Madison St, Winfield, IL 60190 \| Single Family Residential	5 beds \| 3 baths \| 3,693 sq.ft.	$649,900	Airbnb cash on cash: 3.21% Traditional cash on cash: 1.34% Airbnb Rental Income: $5041 Traditional Rental Income: $2880 Airbnb ROI: 3.21% Traditional ROI: 1.34%
26W286 Pinehurst Dr Winfield, IL 26W286 Pinehurst Dr, Winfield, IL 60190 \| Single Family Residential	4 beds \| 3 baths \| 3,101 sq.ft.	$899,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 0.37% Airbnb Rental Income: $2763 Traditional Rental Income: $3149 Airbnb ROI: -0.87% Traditional ROI: 0.37%

Real Estate investment in Winfield, IL

There are 32 properties for sale in the city of Winfield . The median list price in Winfield is $449,631 and the average price per square foot is $225. In August 2026, the average monthly cash on cash return in Winfield is 2.00%. The average monthly rental income in Winfield is $2,370.

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

There are 32 investment properties available for sale in Winfield.

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

The ROI for Short-Term is higher than the Long-Term in Winfield with average rental income of $2,763.

Your search for investment property begins and ends here

Investment Property for Sale in Winfield, IL

27W303 Chartwell Dr

Winfield, IL

4 beds | 3 baths | 2,292 sq.ft.

$569,000

Airbnb cash on cash: 1.08%

Traditional cash on cash: 3%

Airbnb Rental Income: $2763

Traditional Rental Income: $3138

Airbnb ROI: 1.08%

Traditional ROI: 3%

27W119 Cooley Ave

Winfield, IL

3 beds | 1 baths | 1,446 sq.ft.

$315,000

Airbnb cash on cash: 5.5%

Traditional cash on cash: 4.41%

Airbnb Rental Income: $3195

Traditional Rental Income: $2151

Airbnb ROI: 5.5%

Traditional ROI: 4.41%

26W473 Parkway Dr

Winfield, IL

3 beds | 2 baths | 1,985 sq.ft.

$475,000

Airbnb cash on cash: 3%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $3195

Traditional Rental Income: $2810

Airbnb ROI: 3%

Traditional ROI: 3.76%

0S461 Madison St

Winfield, IL

4 beds | 2 baths | 2,809 sq.ft.

$724,900

Airbnb cash on cash: 0.13%

Traditional cash on cash: 1.31%

Airbnb Rental Income: $2763

Traditional Rental Income: $2908

Airbnb ROI: 0.13%

Traditional ROI: 1.31%

27W225 Ash Ct

Winfield, IL

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

$370,000

Airbnb cash on cash: 2.69%

Traditional cash on cash: 3.12%

Airbnb Rental Income: $3195

Traditional Rental Income: $2624

Airbnb ROI: 2.69%

Traditional ROI: 3.12%

0S415 Madison St

Winfield, IL

4 beds | 2 baths | 2,868 sq.ft.

$689,000

Airbnb cash on cash: 0.34%

Traditional cash on cash: 1.51%

Airbnb Rental Income: $2763

Traditional Rental Income: $2865

Airbnb ROI: 0.34%

Traditional ROI: 1.51%

27W084 Fleming Dr

Winfield, IL

4 beds | 2 baths | 1,992 sq.ft.

$465,000

Airbnb cash on cash: 1.64%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $2763

Traditional Rental Income: $3042

Airbnb ROI: 1.64%

Traditional ROI: 3.77%

0S760 Cleveland St

Winfield, IL

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

$52,500

Airbnb cash on cash: N/A

Traditional cash on cash: 7.39%

Airbnb Rental Income: $null

Traditional Rental Income: $653

Airbnb ROI: N/A