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.

Condos for Sale in Winnetka, IL

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

Showing 1 Condo 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
640 Winnetka Mews unit: 405 WINNETKA, IL Welcome to this spacious and sun-filled top-floor residence at the Winnetka Mews, a though...	3 beds \| 3 baths \| 1,862 sq.ft.	$639,000	Airbnb cash on cash: -2.38% Traditional cash on cash: 5.03% Airbnb Rental Income: $2256 Traditional Rental Income: $6110 Airbnb ROI: -2.38% Traditional ROI: 5.03%
Other Investment Properties for Sale in Winnetka
1333 Tower Road WINNETKA , IL Step into a beautifully transformed Hemphill home in Winnetka with private access to the F...	5 beds \| 6 baths \| 3,921 sq.ft.	$1,850,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.25% Airbnb Rental Income: $null Traditional Rental Income: $7701 Airbnb ROI: N/A Traditional ROI: 2.25%
1159 Chatfield Road WINNETKA , IL Blending timeless elegance with modern sophistication, this stunning 2016 Winnetka home fe...	4 beds \| 5 baths \| 4,390 sq.ft.	$2,245,000	Airbnb cash on cash: -0.97% Traditional cash on cash: -0.31% Airbnb Rental Income: $4334 Traditional Rental Income: $4786 Airbnb ROI: -0.97% Traditional ROI: -0.31%
1185 Hill Road WINNETKA , IL Idyllic Cape Cod offering resort-like living with 4+ bedrooms and 5.2 baths, beautifully d...	4 beds \| 7 baths \| 4,269 sq.ft.	$2,439,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 0.88% Airbnb Rental Income: $4334 Traditional Rental Income: $7269 Airbnb ROI: -0.82% Traditional ROI: 0.88%
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%
916 Oak Street WINNETKA , IL An inviting front porch welcomes you into this beautifully renovated home in the heart of ...	4 beds \| 3 baths \| 2,116 sq.ft.	$1,399,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 0.43% Airbnb Rental Income: $4334 Traditional Rental Income: $3819 Airbnb ROI: 0.13% Traditional ROI: 0.43%
985 Pine Tree Lane WINNETKA , IL Set on a half-acre, this custom-built 5+ bedroom, 5.1 bath home offers elegant design, wel...	5 beds \| 6 baths \| 7,200 sq.ft.	$2,885,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.36% Airbnb Rental Income: $null Traditional Rental Income: $7495 Airbnb ROI: N/A Traditional ROI: 0.36%

Your search for investment property begins and ends here

Condos for Sale in Winnetka, IL

640 Winnetka Mews unit: 405

WINNETKA, IL

3 beds | 3 baths | 1,862 sq.ft.

$639,000

Airbnb cash on cash: -2.38%

Traditional cash on cash: 5.03%

Airbnb Rental Income: $2256

Traditional Rental Income: $6110

Airbnb ROI: -2.38%

Traditional ROI: 5.03%

Other Investment Properties for Sale in Winnetka

1333 Tower Road

WINNETKA , IL

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

$1,850,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.25%

Airbnb Rental Income: $null

Traditional Rental Income: $7701

Airbnb ROI: N/A

Traditional ROI: 2.25%

1159 Chatfield Road

WINNETKA , IL

4 beds | 5 baths | 4,390 sq.ft.

$2,245,000

Airbnb cash on cash: -0.97%

Traditional cash on cash: -0.31%

Airbnb Rental Income: $4334

Traditional Rental Income: $4786

Airbnb ROI: -0.97%

Traditional ROI: -0.31%

1185 Hill Road

WINNETKA , IL

4 beds | 7 baths | 4,269 sq.ft.

$2,439,000

Airbnb cash on cash: -0.82%

Traditional cash on cash: 0.88%

Airbnb Rental Income: $4334

Traditional Rental Income: $7269

Airbnb ROI: -0.82%

Traditional ROI: 0.88%

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%

916 Oak Street

WINNETKA , IL

4 beds | 3 baths | 2,116 sq.ft.

$1,399,000

Airbnb cash on cash: 0.13%

Traditional cash on cash: 0.43%

Airbnb Rental Income: $4334

Traditional Rental Income: $3819

Airbnb ROI: 0.13%

Traditional ROI: 0.43%

985 Pine Tree Lane

WINNETKA , IL

5 beds | 6 baths | 7,200 sq.ft.

$2,885,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.36%

Airbnb Rental Income: $null

Traditional Rental Income: $7495

Airbnb ROI: N/A

Traditional ROI: 0.36%

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