Kenilworth Real Estate

Kenilworth Real Estate

Welcome to Kenilworth, Illinois – a hidden gem nestled in the heart of Cook County. This picturesque village, located just 16 miles north of downtown Chicago, offers a unique blend of suburban charm and urban accessibility, making it a highly sought-after destination for families and professionals alike.

Kenilworth is renowned for its beautiful tree-lined streets, meticulously maintained parks, and historic architecture that reflects its rich heritage. With a population of just over 2,500 residents, this close-knit community fosters a warm and inviting atmosphere, where neighbors become friends and community events are cherished traditions. The village prides itself on its strong sense of community, with numerous social gatherings, farmers' markets, and seasonal celebrations that bring residents together.

Education is a top priority in Kenilworth, as it is home to some of the finest schools in Illinois, including the highly regarded Kenilworth School District and New Trier High School. Families appreciate the emphasis on academic excellence and the nurturing environment that encourages students to thrive.

Outdoor enthusiasts will find plenty to love in Kenilworth. The village boasts several parks, including the scenic Kenilworth Beach along Lake Michigan, where residents can enjoy picnics, swimming, and breathtaking sunsets. The nearby Metra train station provides convenient access to Chicago, making it easy to enjoy the vibrant city life while returning to the tranquility of this charming village.

Whether you’re considering a move or simply exploring the area, Kenilworth, Illinois, offers a perfect blend of community spirit, educational excellence, and natural beauty – truly a place to call home.

Newest Listings in Kenilworth

$1,395,000
4 Beds ⋅ 4 Baths ⋅ 12712630 MLS ⋅ ACTIVE Status
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-outdoor living today's buyers are seeking. A welcoming foyer introduces the gracious main level, featuring an expansive living room, formal dining room, and private office with French doors...ideal for working from home. At the heart of the home is a spacious kitchen with a center island, plenty of storage, and a separate dining area, seamlessly opening to the inviting family room with handsome fireplace. French doors lead to the beautifully landscaped, fully fenced backyard, providing an extraordinary amount of outdoor space for entertaining, recreation, and play. A coveted attached two-car garage, mudroom area and powder room complete the main level. Upstairs, four generously sized bedrooms: includeing a spacious primary suite featuring double vanities, a soaking tub, separate shower, and excellent closet space. The expansive lower level adds even more versatility with a large recreation room, bar area, fifth bedroom, and full bath...perfect for guest or extended family living. The location is simply unmatched. Just steps from award-winning Joseph Sears School via the convenient pedestrian tunnel, and minutes from New Trier High School, Lake Michigan beaches, the Metra, and the newly revitalized Plaza del Lago shopping and dining district. A rare combination of space, lot size, location, and lifestyle. Move in before the school year begins and enjoy everything Kenilworth has to offer.

542 Wayland Avenue, Kenilworth
$3,295,000
6 Beds ⋅ 9 Baths ⋅ 12698159 MLS ⋅ ACTIVE Status
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 architecture with exceptional craftsmanship and modern luxury. Rarely does a residence of this architectural beauty and scale become available close to Lake Michigan! Grandly scaled rooms showcase exquisite moldings, bespoke millwork, and five fireplaces, creating an atmosphere of refined elegance throughout. A gracious reception hall with a sweeping circular staircase sets the tone for the home's sophisticated interiors, including a handsome library and beautifully appointed living spaces designed for both intimate gatherings and grand entertaining. The kitchen is a gourmet chefs kitchen and opens into a sun filled family room. The second floor features a luxurious primary suite with a spa-inspired bath and two spacious walk-in closets, three additional bedrooms and three bathrooms. The third floor offers two additional bedrooms, two bathrooms, a reading loft/flex space and playroom. The exceptional lower level is designed for recreation and relaxation, complete with a theater, bar, fitness room, and wine cellar. A four-car garage adds convenience to this remarkable residence. Ideally located near Sears School, New Trier, the train, and just moments from the lakefront, this exceptional home offers an unparalleled North Shore lifestyle of elegance, comfort, and convenience.

110 Kenilworth Avenue, Kenilworth
$2,995,000
5 Beds ⋅ 6 Baths ⋅ 12685718 MLS ⋅ ACTIVE Status

224 Sheridan Road, Kenilworth
$1,595,000
5 Beds ⋅ 3 Baths ⋅ 12703063 MLS ⋅ ACTIVE Status
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 welcoming south-facing three-season porch opens to a grand foyer, leading to a gracious living room with a wood-burning fireplace. Flexible living spaces include an eat-in kitchen, dining room, den, and charming office. Upstairs offers four bedrooms, two Jack and Jill baths, including a primary suite with sitting room and decorative fireplace. The third floor provides endless possibilities as a studio, office, au pair suite, or future primary retreat. Enjoy a private brick paver patio and a home surrounded by mature perennial gardens. Ideally located in coveted East Kenilworth, just moments from Homer's, Joseph Sears School, Metra, and the beach-this exceptional home is a rare offering in one of the North Shore's most sought-after neighborhoods. Best value in East Kenilworth!

325 Oxford Road, Kenilworth
$2,595,000
5 Beds ⋅ 4 Baths ⋅ 12684108 MLS ⋅ ACTIVE Status
Perfectly situated in the heart of Kenilworth, this exceptional home has been completely reimagined for today's lifestyle. REBUILT FROM THE STUDS UP IN 2013 with extraordinary attention to detail, it blends timeless architectural character with modern amenities and a thoughtfully designed floor plan ideal for both everyday living and effortless entertaining. Bathed in sunlight throughout the day, every room is filled with natural light, while the golden hour transforms the surrounding mature trees into a breathtaking backdrop. The home's unique position adjacent to Memorial Park provides a permanent green oasis and rare privacy, with protected open space next door ensuring no future development. A fabulous front porch-widely considered the finest in Kenilworth-welcomes you home and offers the perfect place to relax, entertain friends, or simply enjoy the charm of the neighborhood. Inside, custom moldings, millwork, and a gracious center hall create an elegant flow between the inviting living room, dining room, and spacious family room. The beautifully designed kitchen serves as the heart of the home, featuring quartz countertops, custom cabinetry, high-end stainless-steel appliances, a large center island with seating, and an inviting breakfast area with built-in bench seating overlooking the private backyard. Open to the family room, this space was designed for both comfortable daily living and memorable gatherings. Plantation shutters, a stone fireplace surround, and custom built-in bookcases add warmth and character. A spacious mudroom provides exceptional functionality, while dedicated office spaces on multiple levels offer ideal flexibility for today's work-from-home lifestyle. The light-filled second floor features a generous primary suite that serves as a retreat, complete with built-in bookcases, a walk-in closet, and a ensuite bath with dual vanities and an oversized walk-in shower. Three additional bedrooms, including one with an ensuite bath, a well-appointed hall bath, and a convenient second-floor laundry room complete this level. A beautiful staircase connects all three floors and leads to an expansive third-floor bonus room with an adjoining office or fifth bedroom, providing exceptional flexibility for guests, work, fitness, or recreation. The unfinished basement offers abundant storage and endless possibilities for future expansion. Outside, the professionally landscaped backyard and brick paver patio create a private setting for outdoor entertaining and relaxation. Just steps from award-winning Sears School, New Trier High School, train, shops, restaurants, and only six blocks from Lake Michigan, beaches, and sailing area. This move-in-ready home offers an extraordinary combination of craftsmanship, natural beauty, privacy, and convenience. Rarely does a home combine this level of quality, light, setting, and location. Move right in and begin enjoying the very best of Kenilworth living.

412 Cumnor Road, Kenilworth
$4,499,000
5 Beds ⋅ 7 Baths ⋅ 12689820 MLS ⋅ ACTIVE Status
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 property, highlighted by a serene backyard pool. Expansive marble foyer opens to gracious living room and charming dining room. Dramatic floating staircase. Inviting kitchen with large marble island, fireplace, Grand Palais La Cornue range and table area. Bright sunroom, family room, handsome office and full bath complete the first floor. Second floor includes the primary suite with balcony and 3 more ensuite bedrooms--one with balcony. Third floor offers versatile playroom/lounge area, ensuite bedroom with kitchenette. Lower level exercise room and full bath. An elevator services all four levels, and the attached garage offers parking for 5 cars and EV charging setup. Truly a one-of-a-kind North Shore gem!

528 Roslyn Road, Kenilworth
$2,345,000
6 Beds ⋅ 5 Baths ⋅ 12685606 MLS ⋅ ACTIVE Status
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, the home blends classic detailing with a tailored, city-chic aesthetic across every level. A gracious foyer introduces dramatic entertaining spaces including a striking living room with fireplace and an elegant formal dining room. The butler's pantry connects seamlessly to the custom kitchen, featuring high-end appliances, oversized island seating, and clean-lined finishes, all overlooking the expansive professionally landscaped grounds. The sought-after open floor plan flows effortlessly through the breakfast area and into the family room, creating a polished yet highly functional living space. A private first-floor office with custom built-ins is discreetly tucked away. Additional functional spaces include a spacious mudroom, first-floor laundry, and attached two-car garage. The second level features five bedrooms, including a stunning primary suite with two walk-in closets and a luxe bath with walk-in shower, soaking tub, and dual vanities. One secondary bedroom includes an ensuite bath and walk-in closet, while three additional bedrooms share a well-designed double Jack-and-Jill bath arrangement. The show stopping third-floor addition introduces over 1,200 square feet of architecturally significant living space with sweeping ceiling heights and a distinctly loft-inspired, city-chic sensibility. The level includes a recreation room with kitchenette, exercise studio with reinforced soundproof flooring, full bath, and additional bedroom or flex space. The lower level continues the home's impressive scale with a large recreation room, wet bar, second laundry room, and exceptional storage. Professionally landscaped grounds extend the living space outdoors with a sport court, bluestone terrace, built-in outdoor kitchen, custom firepit, and multiple entertaining areas integrated throughout the property. The thoughtfully executed renovation and expansion by Chip Hackley Architects includes the third-floor addition, new primary suite, mudroom and first-floor laundry, bluestone patio, outdoor kitchen, sport court, window replacement throughout, updated electrical and plumbing systems, and renovated lower level. Throughout, the home reflects a rare combination of architectural integrity, modern functionality, and polished design in one of the North Shore's most sought-after communities.

520 Greenwood Avenue, Kenilworth
$5,975,000
6 Beds ⋅ 9 Baths ⋅ 12672126 MLS ⋅ ACTIVE Status
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 restaurants, Kenilworth beach, schools and train the house features 7 bedrooms, 8.1 bath, 3 fireplaces, spectacular kitchen with top-of-the-line appliances including Sub-Zero refrigerators/freezers, luxury Wolf range, espresso/cappuccino machine, drawer style microwave, and much more, walnut library has a built-in desk and filing cabinets. Spectacular finished lower level includes entertainment room with fireplace and TV, refrigerated wine cellar, full size wet bar, media room with 4K technology, surround sound and leather reclining chairs. Sport Court. The house also offers security system, back-up generator. home is prewired for Smart home system. House has 3 stops elevator. This house has it all! Agent owned.

455 Sheridan Road, Kenilworth
$2,975,000
4 Beds ⋅ 5 Baths ⋅ 12561462 MLS ⋅ ACTIVE Status
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 the one of kind features that make this home unique in its construction and details. First floor features stunning two-story foyer with iron rail. A step-down living room includes inlaid wood floor, beamed ceiling and bay, and an elegant limestone fireplace. Handsome paneled library with fireplace. An open floor plan creates great spaces for family living and entertaining. Tile roof. Fabulous East location being the third house from Lake Michigan.

123 Oxford Road, Kenilworth
$16,750,000
6 Beds ⋅ 9 Baths ⋅ 12522887 MLS ⋅ ACTIVE Status
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 roof which represents timeless construction. Close to Plaza del Lago with its numerous shops and restaurants, Kenilworth beach, schools and train the house features 7 bedrooms, 8.1 bath, 4 fireplaces, spectacular Neff kitchen with top-of-the-line appliances including Sub-Zero refrigerators/freezers, luxury Wolf range, espresso/cappuccino machine, drawer style microwave, and much more, walnut library has a built-in desk and filing cabinets. Spectacular finished lower level includes entertainment room with fireplace and TV, refrigerated wine cellar, full size wet bar, media room with 4K technology, surround sound and leather reclining chairs. Sport Court. The house also offers security system, back-up generator. home is prewired for Smart home system. House has 3 stops elevator. This house has it all! Agent owned.

501 Sheridan Road, Kenilworth
$1,900,000
12476302 MLS ⋅ ACTIVE Status
Mixed-Use Investment Opportunity on the North Shore! 626-630 Green Bay Road offers a rare chance to acquire a distinctive mixed-use property in one of Chicagoland's most desirable communities- ideal for investors, owner-users, or developers seeking upside. Property Overview; Situated in the heart of Kenilworth along prestigious Green Bay Road, this 10,925 SF mixed-use building sits on a 9,000 SF lot and combines retail, office, and residential space. Parking: 10 on-site spaces; Residential & Office Components: Three (3) 2BR / 1BA Apartments - spacious layouts with strong rental demand, condo-quality upgrades. Two Loft-Style Office Spaces - modern design, each with ADA-compliant restrooms, making them ideal for professional tenants or creative firms. Retail/Commercial Space: Ground floor features high-visibility retail with unique architectural character, excellent signage opportunities, and steady foot traffic. Flexible floor plan allows for a wide variety of tenant uses and potential to divide. Location Highlights; Positioned on Green Bay Road, a main retail artery, offering maximum exposure and accessibility. Walking distance to the Metra station, providing convenient commuter access. Surrounded by boutique shops, restaurants, and affluent residential neighborhoods. Versatile design with multiple revenue streams. Prime North Shore location ensures long-term value appreciation and strong tenant demand.

630 Green Bay Road, Kenilworth
$2,660,000
6 Beds ⋅ 7 Baths ⋅ 12356234 MLS ⋅ ACTIVE Status
Fully Renovated 6BR 5.5BA Classic Home in Unbeatable East Kenilworth Location. This Elegant home sits on a large lot on one of Kenilworth's most serene streets. FIRST FLOOR: Elegant LR w/ Thibault Grasscloth Wallpaper & Custom Solid Wood Built Ins, Custom Handmade Mosaic Entry, Traditional DR w/ Brick Fireplace. Kitchen boasts both a Butler's Pantry and Prep Station, Quartz Countertops and herringbone Italian Calacatta Marble backsplashes & features: A full eating area & a counter bar eating area too, a 30" Subsero combo fridge/ freezer, Larger pantry, Two double under-mount cast iron sinks, two Bosch SS D/W & two Garbage disposals, One gas oven, one electric oven, one 30" SS microwave w digital displays. A 48" Wolf gas Rangetop, 4 gas burners, 1 electric burner Grill Cook Top for the breakfast area, A white Countertop and blue Marble countertop for the breakfast area & an under & inside cabinet lights. Eat-In Breakfast Nook with space for a larger table & 4 chairs w/w/skylight overlooks sunny large backyard & over counter bar seating area. A bar area w liquor & glass cabinet, an under-counter shelf refrigerator, Ice maker & a beverage refrigerator. Attached 3 Garage with Massive Storage availability. Superior Flow for casual gatherings and entertaining & an Extra 3 Season Porch. SECOND FLOOR: 4 BRS each with En Suite BA, each with thoughtful design. PRIMARY Bedroom w/ HIS/HERS BAs and Closets. Make up bathroom w/ carrara marble & a seat-in area, floor-to-ceiling custom mirror, full bathroom with glass shower doors. All Baths completely remodeled with Italian marble and hand-poured tile / Restoration Hardware Fixtures. Second Floor Laundry with Large Linen Closet and Brand New LG Machines. THIRD FLOOR: 2 Spacious Bedrooms and Full BA with Stone Fixtures and Calacatta Tile. BASEMENT - Completely Renovated Basement with New Perimeter Drain Tile and Sump Pump with Front Yard Pop Up Emitter Water Control System. Full Large Laundry Room and Finished Rec Room Perfect for an additional Play Room, Office, or Exercise Room. New attached 3-car garage. Large lot and professionally designed landscaping-walking distance to Sears (JK-8) and New Trier.

527 Warwick Road, Kenilworth
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