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 |
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...
If There Was A Master Class In How To Transform An Architecturally Significant Home Through Creative Reinvention With A Fearless Celebration Of Incredible Design, 320 Melrose Would Win The Prize, Along With A Second For The Newly Finished Matching...
CONTINGENT This Distinctive Center-entrance Brick Dutch Colonial Is Located On A Quiet, Tree-lined Street Near The Lake, Train, And Local Schools. The Main Level Features A Spacious Entryway Leading To A Living Room With A Wood-burning Fireplace And Built...
Set On A Coveted Street In Kenilworth, This Impeccably Maintained Home Pairs Timeless Architecture With An Exceptionally Rare Floor Plan Featuring Six Bedrooms, Including Five On The Second Level. Thoughtfully Expanded And Extensively Renovated, T...
Enjoy The Lake Michigan Breezes At This Spectacular 9 Bedroom 5.2 Bathroom Home Clarence A. Hemphill Built For Himself! Located At The Eastern Corner Of Sheridan Road And Kenilworth Avenue, This Amazing, Oversized Property Boasts A Beautiful Front...
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 Picture-perfect And Deceptively Spacious, This Kenilworth Gem Delivers The Lifestyle Everyone Is Looking For! A Welcoming Front Porch Sets The Tone, Perfect For Morning Coffee Or Unwinding At Sunset. Inside, The Main Level Offers Effortless Flow F...
CONTINGENT This Gorgeous And Pristine Home Checks All The Boxes! Beautifully Updated Throughout With Lovely Flow For Entertaining And Perfectly Proportioned Room Sizes, Your Ideal Lifestyle Is Here! The Generous Foyer Leads To The Spacious Living Room With...
This Extraordinary 6-bedroom, 7.2 Bath Stone French Normandy Manor Is Set On An Expansive, Exquisitely Landscaped Estate And Has Been Masterfully Restored, Expanded, And Renovated. This Wonderful Estate Seamlessly Blends Timeless European Architec...
CONTINGENT A Charming, Bright, And Light Tudor Located On A Fabulous, Quiet Street In The Heart Of Kenilworth. Completely Rebuilt In 1997...including A New Foundation...this Home Was Taken Down To The Studs And Redesigned With An Exceptional Floor Plan Ideal...
Sought After Brick And Limestone Georgian On 100 X 175 Lot In East Kenilworth. Tile Roof On Timeless Architectural Details Abound In This Exceptional Home In East Kenilworth. Plaster Cast Ceilings, Leaded And Stain Glass Windows Are Just Some Of T...
Stunning French Manor House On One Of East Kenilworth's Most Beautiful Streets. Stylish And Sophisticated, This Unique Home Is Perfectly Situated Near The Lake, Train, Sears School, And New Trier High School. Luxurious Landscaping Envelopes The P...
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 June 8th, 2026 at 1:29am CDT.
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