Winnetka, IL Houses for Rent

/21
$18,000 Per Month
- 6 Beds
- 5.5 Baths
- House for Rent
82 Woodley Rd, Winnetka, IL 60093

Tucked away on one of Winnetka's most prestigious and serene lanes, this estate offers a rare blend of timeless North Shore elegance and a sense of true sanctuary. This isn't just a home; it's a sprawling residence designed for a lifestyle of both grand-scale entertaining and quiet, sun-drenched mornings. From the moment you pull up the winding drive, the home's commanding presence and lush,

Michael Mitchell @properties Christie's International Real Estate

82 Woodley Rd, Winnetka, IL 60093
Explore Winnetka
/75
$35,000 Per Month
- 6 Beds
- 9 Baths
- 7,539 Sq Ft
- House for Rent
70 Harbor St, Glencoe, IL 60022

Discover paradise in this custom-built home on lake Michigan in the beautiful village of Glencoe with its own private beach and deck. This furnished gem of a property is a perfect opportunity for a discerning family interested in gaining access to the desirable New Trier school district for 2026-2027 academic year. Ideal for entertaining, the interior highlights include a saltwater pool, vaulted

Merav Argov Baird & Warner

70 Harbor St, Glencoe, IL 60022

Illinois Cook County

Frequently Asked Questions

How much does it cost to rent a single-family home in Winnetka, IL?

The median rent for a single-family home in Winnetka, IL is $9,900 per month, though prices vary by neighborhood, size, and property type. As of July 2026, condos tend to be the most affordable option while townhouses and single-family homes are currently more expensive.

How much do you need to make to afford rent in Winnetka, IL?

To comfortably afford the median rent in Winnetka, IL, a household needs to earn roughly $71,800 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $1,795 per month in Winnetka, IL, renters typically need to show $5,385 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.

Is it more affordable to rent or buy in Winnetka, IL?

In Winnetka, IL, the price-to-rent ratio is 88.1, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.

What neighborhoods in Winnetka, IL are best for renting a single-family home?

The best neighborhood for renting in Winnetka, IL depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a single-family home include North Skokie and East Highland Park, each with its own character and price range.

Rental Home Trends in Winnetka, IL

There are currently 2 single-family homes available for rent in Winnetka, IL. The median rent is $9,900 per month, with 3-bedroom houses renting at $4,300, 4-bedroom houses at $9,900 and 5-bedroom houses at $9,000.

Rental Home Trends

Number of Houses for Rent 2	Median Single Family Home Rent $9,900
Median 3 Bedroom Single Family Home Rent $4,300	Median 4 Bedroom Single Family Home Rent $9,900
Median 5 Bedroom Single Family Home Rent $9,000

How to Rent a Home

Rentals in Winnetka

Houses for Rent by Bedrooms in Winnetka

5 Bedroom Houses for Rent in Winnetka

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