Real Estate Investment Properties for Sale in Winnetka, IL

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

Explore a variety of short-term homes & houses in Winnetka, IL. Invest wisely with VRBO & Winnetka, IL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Winnetka, IL

Search for Single Family Residential for Sale in Winnetka, Illinois. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 9 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
305 Poplar Street WINNETKA, IL One of East Winnetka's most coveted locations! Handsome brick Colonial with separate studi...	3 beds \| 3 baths \| 3,128 sq.ft.	$1,250,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 0.22% Airbnb Rental Income: $2256 Traditional Rental Income: $3271 Airbnb ROI: -1.14% Traditional ROI: 0.22%
275 White Oak Lane WINNETKA, IL First Time on the Market - Coveted White Oak Lane Tucked away on a private 1/2 acre lot...	4 beds \| 6 baths \| 3,598 sq.ft.	$1,599,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 1.6% Airbnb Rental Income: $4334 Traditional Rental Income: $6708 Airbnb ROI: -0.61% Traditional ROI: 1.6%
342 Rosewood Avenue WINNETKA, IL Sophisticated perfection on an extra wide lot in one of Winnetka's most picturesque neighb...	4 beds \| 5 baths \| 4,585 sq.ft.	$1,995,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 0.46% Airbnb Rental Income: $4334 Traditional Rental Income: $5110 Airbnb ROI: -0.45% Traditional ROI: 0.46%
650 Winnetka Mews #310 WINNETKA, IL Fabulous opportunity to own this 2 Bed/2 Bath condo in sought after Winnetka Mews building...	2 beds \| 2 baths \| 1,630 sq.ft.	$489,000	Airbnb cash on cash: -2.88% Traditional cash on cash: -0.81% Airbnb Rental Income: $2011 Traditional Rental Income: $2432 Airbnb ROI: -2.88% Traditional ROI: -0.81%
334 Woodland Avenue WINNETKA, IL Absolutely breathtaking "better-than-new" East Winnetka Classic on an oversized (75' wide)...	4 beds \| 5 baths \| 3,748 sq.ft.	$2,799,000	Airbnb cash on cash: -0.95% Traditional cash on cash: -0.27% Airbnb Rental Income: $4334 Traditional Rental Income: $5191 Airbnb ROI: -0.95% Traditional ROI: -0.27%
1333 Tower Road WINNETKA, IL Beautifully reimagined in 2023, this custom Hemphill-designed home blends modern elegance ...	5 beds \| 6 baths \| 3,921 sq.ft.	$2,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.83% Airbnb Rental Income: $null Traditional Rental Income: $7701 Airbnb ROI: N/A Traditional ROI: 1.83%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winnetka, IL

305 Poplar Street

WINNETKA, IL

3 beds | 3 baths | 3,128 sq.ft.

$1,250,000

Airbnb cash on cash: -1.14%

Traditional cash on cash: 0.22%

Airbnb Rental Income: $2256

Traditional Rental Income: $3271

Airbnb ROI: -1.14%

Traditional ROI: 0.22%

275 White Oak Lane

WINNETKA, IL

4 beds | 6 baths | 3,598 sq.ft.

$1,599,000

Airbnb cash on cash: -0.61%

Traditional cash on cash: 1.6%

Airbnb Rental Income: $4334

Traditional Rental Income: $6708

Airbnb ROI: -0.61%

Traditional ROI: 1.6%

342 Rosewood Avenue

WINNETKA, IL

4 beds | 5 baths | 4,585 sq.ft.

$1,995,000

Airbnb cash on cash: -0.45%

Traditional cash on cash: 0.46%

Airbnb Rental Income: $4334

Traditional Rental Income: $5110

Airbnb ROI: -0.45%

Traditional ROI: 0.46%

650 Winnetka Mews #310

WINNETKA, IL

2 beds | 2 baths | 1,630 sq.ft.

$489,000

Airbnb cash on cash: -2.88%

Traditional cash on cash: -0.81%

Airbnb Rental Income: $2011

Traditional Rental Income: $2432

Airbnb ROI: -2.88%

Traditional ROI: -0.81%

334 Woodland Avenue

WINNETKA, IL

4 beds | 5 baths | 3,748 sq.ft.

$2,799,000

Airbnb cash on cash: -0.95%

Traditional cash on cash: -0.27%

Airbnb Rental Income: $4334

Traditional Rental Income: $5191

Airbnb ROI: -0.95%

Traditional ROI: -0.27%

1333 Tower Road

WINNETKA, IL

5 beds | 6 baths | 3,921 sq.ft.

$2,100,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.83%

Airbnb Rental Income: $null

Traditional Rental Income: $7701

Airbnb ROI: N/A

Traditional ROI: 1.83%

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