Buying a Home in Winnetka

Winnetka Jena Radnay June 22, 2023

Winnetka is a truly mesmerizing town with gorgeous tree-lined roads, a lush landscape, and breathtaking views of the lake and Chicago skyline. Its beauty has made it a popular filming location for many classic films, while its charm has kept families rooted in the town for generations.

There's something undeniably alluring about Winnetka, so be warned: if you read too much about it, you might just fall under its spell. There’s so much to look forward to when buying a home in Winnetka, so let’s get started!

Why Winnetka?

  • A small-town atmosphere
  • Scenic and charming surroundings
  • Close to Chicago and all its amenities
As part of the glorious North Shore, Winnetka is replete with splendor and sophistication at every turn. With incredible beaches, green spaces, and parks galore, this is an outdoor enthusiast’s wonderland. Centennial Beach, a fun-filled swimming beach for dogs, is the go-to spot for your furry friends to make a splash. Other beautiful beaches in the area include Tower Road Beach, Maple Street Beach, and Lloyd Beach (a great spot for boating!).

Don’t miss a delightful meal at Kyoto Sushi, where the fried rice and chef’s specials never fail to impress. For exquisite French cuisine, look no further than Pomeroy. From the Maine lobster tail risotto to the fresh wild Holland Dover sole, the flavors here are endless.

If it’s retail therapy you’re after, explore one of Winnetka’s many special shopping spots. Head to Ellen’s on Elm for unique gifts or Bunny and Babe for designer clothing in an upscale boutique. And, don’t miss Winnetka’s many celebrations and festivities on the calendar, including the Winnetka Music Festival each June.

Top Winnetka neighborhoods

There are various subdivisions in Winnetka, but most locals divide it according to three of its elementary school boundaries. When buying a home in Winnetka, make sure to research individual subdivisions, as it’s essential to find a community that feels perfect for you and your lifestyle!


The Greeley neighborhood is on the southeastern side of Winnetka, bordering beautiful Lake Michigan to the east. It enjoys the longest stretch of Sheridan Road, which runs alongside the lake and its shimmering views. Public beaches and gorgeous lakefront homes can be found here. Many of the houses in the neighborhood are within walking distance of the Metra station, which makes commuting a breeze. Winnetka’s downtown district, with its charming shops and posh restaurants, is also in this area. It is easy to see why Greeley is the most coveted area in the village.

Hubbard Woods

Hubbard Woods is situated in the northern section of Winnetka and is filled with trees and lush greenery, with fantastic lakefront properties lining a section of Sheridan Road. Although not located in the downtown core, Hubbard Woods boasts its own walkable district on Green Bay Road with charming boutiques and eateries to explore.

Crow Island

To the west of the Greeley neighborhood and south of Hubbard Woods lies Crow Island. For what it lacks in water views, it makes up for in wide open grassy areas, hiking paths, and beautiful parks. The southern part of Crow Island is close to the Indian Hill Club and the village of Wilmette.

A closer look at the housing options in Winnetka

Single-family homes

The Winnetka real estate landscape features stunning properties in an array of impressive architectural styles. Queen Anne, English Tudor, Art Deco, Dutch Colonial, Georgian, and Contemporary are just a few of the astounding architectural styles found here. Buyers can seek out properties in nearly any style, from small bungalows to updated, palatial estates and everything in between.

If all of this sounds appealing, read on for an overview of what you can expect as you embark on your house hunt.

Determining your budget

Finding the right property for your finances in Winnetka

While the beginning of your homeownership journey is undoubtedly an exciting milestone, it’s essential to be prepared!

First, set a budget by evaluating your finances and getting pre-approved for a home loan. This will ensure that you focus on properties that meet your financial criteria while you search for a new home. There are several types of loans you may have heard about; work with your lender to determine which ones you qualify for and which ones best fit your goals. When getting quotes from lenders, don’t forget to compare rates from several lenders to find the best fit.

After you are pre-approved for a loan, your Winnetka real estate agent will connect you with amazing properties that fit your wish list, priorities, and budget. That way, you can move forward confidently toward your dream home!

Remember the closing costs and other expenses

Closing costs are fees associated with taking out a mortgage and are paid by the buyer at closing. Attorney’s fees, insurance, application fees, and more are all examples of closing costs. Of course, your agent will be by your side at every point, making sure you understand all your expenses and documentation. Other costs to keep in mind include property taxes and homeowner’s insurance, as well as HOA fees, if applicable.

The most important tip of them all

Buying a home in Winnetka is an exciting yet challenging journey. As you begin the process, you’ll soon find it’s not as easy as searching online for listings, making an offer, and packing up your belongings in boxes. The good news is, though, that you don’t have to go through it alone! One of the most essential home-buying tips is to team up with a real estate professional who knows the area inside and out.

Jena Radnay is a trusted broker whose accolades speak for themselves: she is the number one broker in Winnetka and the North Shore, with a success-focused mindset and a commitment to excellence. Buyers and sellers appreciate Jena’s personal touch and her knowledge and determination at every point. They know that when Jena is on their side, they don’t need to stress. If you have questions about the market or real estate goals you’re ready to reach, contact Jena today.

*Header photo courtesy of Jena Radnay

Work With Jena

Jena Radnay, and the focus of her real estate business, is all about people. Radnay’s love for real estate, houses, marketing, and people have allowed her business to grow organically, albeit explosively, in large part from referrals from her extensive network of contacts and connections.