Kenilworth is a meticulously designed community with less than 1,000 homes occupying a scenic .6-mile radius. Coveted for its graciousness and natural beauty, your choices will range from architecturally significant lakefront mansions to contemporary Prairie-style homes, all within a close proximity to the finest schools, including top-rated Joseph Sears and New Trier High School, cozy parks, public beaches, restaurants, and the Kenilworth Metra Station, for a quick ride to downtown Chicago. New construction is also an option but designs must meet strict architectural standards to maintain Kenilworth’s tradition of elegance. LEARN MORE
| $1,000,000 - $2,000,000 | $2,000,000 - $3,000,000 | $3,000,000 - $5,000,000 |
| $5,000,000 - $10,000,000 | Over $10,000,000 |
Rare Opportunity To Complete A Comprehensive Renovation Of A Stately Prairie-influenced Residence On A Prominent Corner Lot Along One Of Kenilworth's Most Picturesque, Tree-lined Streets. The Home's Interior Has Been Substantially Gutted, Includin...
Elegant, Distinctive, And Impeccably Refreshed, This 5 Bedroom & 7 Bathroom Home Is A One-of-a-kind North Shore Residence Offering An Exceptional Lifestyle In The Heart Of East Kenilworth With An Attached 5 Car Garage (ev Charging Capability) For ...
Perfectly Situated In The Heart Of Kenilworth, This Exceptional Home Combines An Irreplaceable Setting With Timeless Character, Abundant Natural Light, And Modern Functionality. Rebuilt From The Studs Up In 2013, The Home Sits Adjacent To Memorial...
Enjoy Lake Breezes And Seasonal Views From This Beautifully Renovated East Kenilworth Home. Tucked Down A Private Dead-end Lane East Of Sheridan Road, The Home Was Fully Renovated Prior To The Current Owner's Purchase In 2021, And They Have Contin...
CONTINGENT Better Than New! This Extraordinary Kenilworth Home...seamlessly Blends Timeless Architectural Character With A Comprehensive, Down-to-the-studs Renovation And A Significant Rear Addition Completed In 2025. Expanded And Reimagined For Today's Life...
CONTINGENT Perfectly Located On Soughtafter Sheridan Road In The Heart Of Kenilworth, This Stately Redbrick Colonial Sits Quietly Behind A Circular Drive And Landscaped Gardens, Offering Wonderful Privacy On Nearly A Halfacre. Originally Built In 1918, The H...
CONTINGENT Rarely Available, This Spacious All-american Home Sits On An Oversized Private Lot (149 X 135 X 125 X 55). Built In 1994 And Deceptively Large, This Thoughtfully Designed Residence Offers The Generous Room Sizes, Functional Floor Plan, And Indoor-...
CONTINGENT Incredible Price Improvement In This Gorgeous Designer-owned Serene East Kenilworth Home In An Idyllic Setting. Filled With Timeless Vintage Charm And Beautiful Architectural Details. Sun-drenched, Spacious Rooms And Large Windows Throughout. A We...
New Magnificent Transitional Home With Approximately 11,000 Square Feet Finished Space. Exterior Is Constructed Of Brick And Limestone With Slate Roof Which Represents Timeless Construction. Close To Plaza Del Lago With Its Numerous Shops And Rest...
New Lakefront Magnificent Transitional Home With Approximately 17,000 Square Feet Finished Space. This House Has Oversized Windows With Nonrestricted Lake Vews And A Future Private Beach.exterior Is Constructed Of Stone And Limestone With Slate Ro...
Kenilworth School District 38: This district operates The Joseph Sears School, which is a public elementary school serving grades pre-kindergarten through 8. It is the only school within the district.
New Trier Township High School District 203: This district operates New Trier High School, which is a highly regarded public high school serving the communities of Kenilworth, Winnetka, Glencoe, Northfield, and parts of Wilmette and Glenview.
The North Shore Chicago listings on this page include Kenilworth IL homes for sale. The property listings are updated as soon as they hit the market with new Kenilworth homes for sale and rent. Start your home search and schedule showings online or to learn more about Kenilworth and Chicago's North Shore call 312.961.6212
The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than Sotheby's International Realty are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.
Listing information last updated on September 14th, 2026 at 9:14pm CDT.
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