26

Winnetka, IL Houses for Sale

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  • /57

    $2,895,000

    • 6 Beds
    • 6.5 Baths
    • 5,500 Sq Ft

    527 Warwick Rd, Kenilworth, IL 60043

    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

    Paul Harb Wilmette Real Estate & Management Company LLC

    527 Warwick Rd, Kenilworth, IL 60043
  • /63

    $2,575,000

    • 4 Beds
    • 4.5 Baths
    • 3,973 Sq Ft

    1300 Hackberry Ln, Winnetka, IL 60093

    This is the quintessential All-American Beauty nestled on private lane in desirable Winnetka on a half acre with a pool! This home was completely rebuilt and redsigned for today's lifestyle in (2003-2004) - it is impeccable inside and out! Not much remains of the original home. The attention detail is everywhere...outstanding craftmanship and exceptional millwork throughout. A large foyer with

    Megan Mawicke @properties Christie's International Real Estate

    1300 Hackberry Ln, Winnetka, IL 60093
  • /71

    $4,250,000

    • 8 Beds
    • 7 Baths
    • 7,168 Sq Ft

    5 Woodley Rd, Winnetka, IL 60093

    This estate delivers the ultimate outdoor summer experience. It's time to sip 5pm summer cocktails in a true country club setting with gorgeous vistas of precisely manicured grounds from the tiered entertaining bluestone patios with the soothing sounds of the fountain trickling in the background. And as the sun sets, enjoy evenings under the stars in the tasteful, boutique hotel level hot tub

    Jena Radnay @properties Christie's International Real Estate

    5 Woodley Rd, Winnetka, IL 60093
  • /49

    $2,499,000

    • 6 Beds
    • 7 Baths
    • 5,350 Sq Ft

    1423 Asbury Ave, Winnetka, IL 60093

    Better than NEW! Impeccably renovated 6BR/5.2BA center-entry colonial set on an oversized (66 x 159) professionally landscaped lot. This four-level home features abundant natural light, oversized windows, wide room openings, custom millwork and gleaming hardwood floors throughout. Spacious rooms, a current layout, high-end finishes and thoughtful design exist at every turn. First floor includes a

    Laura McCain Compass

    1423 Asbury Ave, Winnetka, IL 60093
  • /72

    $4,599,000

    • 6 Beds
    • 6 Baths
    • 6,639 Sq Ft

    22 Indian Hill Rd, Winnetka, IL 60093

    Nestled privately amidst the prestigious landscape of Indian Hill Road, this magnificent English manor, designed by renowned architect Edwin Clark, presents an unparalleled opportunity to immerse yourself in the epitome of understated luxury living. From its commanding position on an expansive 1.7-acre grounds, this once-in-a-lifetime estate exudes timeless elegance and refinement at every turn.

    Paige Dooley Compass

    22 Indian Hill Rd, Winnetka, IL 60093
  • /85

    $2,799,000 Open Sun 2PM - 3:30PM

    • 4 Beds
    • 4.5 Baths

    1098 Fisher Ln, Winnetka, IL 60093

    Welcome to your dream home, just steps from the Hubbard Woods shops restaurants, park and train, and Lake Michigan. Set on over an acre with lush lawns and ravine views, this property offers a tranquil setting like no other. Enjoy an outdoor spa with a fireplace and outdoor shower, all with breathtaking views and privacy. Inside, find a beautiful kitchen with a center island which opens to the

    Joanne Hudson Compass

    1098 Fisher Ln, Winnetka, IL 60093
  • /39

    $4,500,000

    • 4 Beds
    • 7 Baths
    • 8,294 Sq Ft

    977 Sheridan Rd, Winnetka, IL 60093

    Perfectly situated in a discreet upscale enclave east of Sheridan road. Beautifully tucked away is where you'll find this gorgeous estate on a professionally landscaped .659 acre. With exceptional quality, elegance and design throughout there are many updates that have been done over the last 3 years. Upon entering the foyer you'll see 12-14 ceilings and gorgeous marble floors. New Kitchen with

    Kim Kelley Baird & Warner

    977 Sheridan Rd, Winnetka, IL 60093
  • /64

    $3,299,000

    • 6 Beds
    • 5.5 Baths
    • 6,384 Sq Ft

    646 Prospect Ave, Winnetka, IL 60093

    Spectacular East Winnetka in-town oasis on almost 1/2 acre of lushly landscaped grounds offers a singular opportunity to walk everywhere from a private, fully renovated classic located in a premier location with 150 ft frontage, just steps to town, train, and beach. Meticulously transformed and completely reimagined inside and out with one of the best first floor living spaces, this 6 bedrooms

    Paige Dooley Compass

    646 Prospect Ave, Winnetka, IL 60093
  • /46

    $2,900,000

    • 8 Beds
    • 7 Baths
    • 7,215 Sq Ft

    1250 Westmoor Rd, Winnetka, IL 60093

    Upon entering the grounds of this remarkable English Manor Home through the grand stone circular driveway adorned with pillars, you're greeted by an impressive foyer featuring Paradiso marble flooring inlaid with creamy travertine. This area provides access to the first-floor rooms and leads to a 1,500-square-foot elevated bluestone terrace. The elegant living room, with its bay window, offers

    Dinny Dwyer Compass

    1250 Westmoor Rd, Winnetka, IL 60093
  • /38

    $2,849,000

    • 5 Beds
    • 6.5 Baths
    • 5,783 Sq Ft

    96 Harbor St, Glencoe, IL 60022

    Privately nestled on a beautifully landscaped half-acre in East Glencoe just steps from the lake, this striking contemporary home designed by renowned architect Tony Grunsfeld seamlessly blends architectural pedigree with modern sophistication. Elegantly reimagined with timeless upgrades, the home's airy, open-concept layout embraces natural light and the surrounding landscape through walls of

    Susan Maman @properties Christie's International Real Estate

    96 Harbor St, Glencoe, IL 60022
  • /70

    $3,295,000

    • 5 Beds
    • 5.5 Baths
    • 5,118 Sq Ft

    530 Essex Rd, Kenilworth, IL 60043

    Transitional, sun-filled newer construction home on an oversized lot (110 x 175) in a PRIME East Kenilworth location! This stunning home is on one of the best blocks in town, boasting over 6,000 square feet of living space with grandly scaled rooms, amazing natural light, high ceilings, beautiful windows, walnut floors throughout and 4 floors of fabulous living for today's lifestyle! The

    Megan Mawicke @properties Christie's International Real Estate

    530 Essex Rd, Kenilworth, IL 60043
  • /35

    $875,000 Open Sat 12PM - 3PM

    • 3 Beds
    • 1.5 Baths
    • 2,571 Sq Ft

    38 Brier St, Winnetka, IL 60093

    Distinctive architecture, throughout this Tudor-style home with a steep gabled roof. Spacious living room with prominent fireplace, a formal dining room, and a large cathedral ceiling family room are just a few of the special features. Beautifully refinished floors through. Large lot. Short walk to the train lake and award-winning Joseph Sears School. Home is being sold as-is.

    Joseph Nash @properties Christie's International Real Estate

    38 Brier St, Winnetka, IL 60093
  • /33

    $1,199,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 2.5 Baths
    • 3,520 Sq Ft

    458 Sunset Rd, Winnetka, IL 60093

    Bring your design ideas and creativity to this 4 Bedroom home located in prime East Winnetka location- walkable to Greeley, New Trier, Indian Hill train stop, beach, and parks! A thoughtful and functional main level features living room, dining room, powder room and kitchen, which opens to a generous sized family room and breakfast area. Three bedrooms plus the primary suite reside on the

    Emily Smart LeMire Compass

    458 Sunset Rd, Winnetka, IL 60093
  • /25

    $1,195,000

    • 5 Beds
    • 3.5 Baths
    • 2,714 Sq Ft

    1288 Sunview Ln, Winnetka, IL 60093

    Discover an incredible opportunity to either construct a brand-new home or renovate this charming traditional residence situated on a picturesque half-acre lot. Step into the welcoming entrance hall, complete with a guest powder room and closet, leading to a spacious living room featuring a cozy fireplace and panoramic views of the property. The inviting dining room sits conveniently adjacent to

    Dinny Dwyer Compass

    1288 Sunview Ln, Winnetka, IL 60093
  • /11

    $899,000

    • 3 Beds
    • 3 Baths
    • 1,920 Sq Ft

    1253 Cherry St, Winnetka, IL 60093

    Motivated seller! A beautiful red brick home, center entrance colonial, in a prime Winnetka location that gushes with natural sunlight. The combination of a prime location coupled with a superb floor plan and great bones puts this in a unique category all by itself. Walk to Crow Island, Skokie, Washburne and park district field/sports complex.: two fireplaces, wood burning and gas, walk up attic

    Misael Chacon Beycome brokerage realty LLC

    1253 Cherry St, Winnetka, IL 60093
  • /33

    $2,199,000

    • 5 Beds
    • 4.5 Baths
    • 4,544 Sq Ft

    355 Myrtle St, Winnetka, IL 60093

    Timeless Elegance in the Heart of East Winnetka! Set on an expansive, professionally landscaped lot, this East Winnetka residence exudes timeless elegance and exceptional curb appeal. A grand foyer welcomes you into a home where classic architecture meets modern comfort. The richly paneled family room offers a sophisticated retreat, while the formal living room, bathed in natural light, features

    Mary Grant @properties Christie's International Real Estate

    355 Myrtle St, Winnetka, IL 60093
  • /28

    $1,135,000

    • 4 Beds
    • 2.5 Baths
    • 2,380 Sq Ft

    1492 Asbury Ave, Winnetka, IL 60093

    Rehabbers-Opportunity Awaits! Have you been searching for a home on one of Hubbard Woods' most cherished streets? A place where your family can grow, in a community known for its charm and friendly community? This is that rare opportunity. This solid 4 bed, 2.5 bath home is full of potential and perfectly situated in a sought-after neighborhood with top-rated schools. With thoughtful updates

    Maria Welch Perennial Properties

    1492 Asbury Ave, Winnetka, IL 60093
  • /101

    $5,995,000

    • 5 Beds
    • 8 Baths
    • 13,482 Sq Ft

    624 Pine Ln, Winnetka, IL 60093

    Welcome to this stunning custom home designed by Morgante Wilson, with thoughtful input from discerning owners. This once in a lifetime home is nestled on a picturesque 0.86-acre lot on private Pine Lane near schools, town and train. This thoughtfully designed home is perfect for all ages, blending creativity and style throughout. The inviting entrance hall sets the tone as you walk in, leading

    Joanne Hudson Compass

    624 Pine Ln, Winnetka, IL 60093
  • /19

    $1,995,000

    • 4 Beds
    • 5 Baths
    • 3,700 Sq Ft

    314 Woodland Ave, Winnetka, IL 60093

    Handsome Georgian home underwent a complete restoration and remodel (2016) to preserve its antique charm and vintage details. Fantastic east Winnetka location - walk to Greeley, New Trier, Lake Michigan, and commuter train. Beautiful brick exterior with slate roof sets the tone for the entire home. kitchen with Decora cabinets, two spacious pantries, eat-in bar plus table space. 3 fireplaces,

    Margaret Goss @properties Christie's International Real Estate

    314 Woodland Ave, Winnetka, IL 60093
  • /55

    $4,950,000 Open Sun 1PM - 3PM

    • 5 Beds
    • 7 Baths
    • 9,908 Sq Ft

    32 Woodley Rd, Winnetka, IL 60093

    Nestled down a winding, private road on 1.9 meticulous park-like acres, this grand, almost 10,000 square foot residence exudes luxury and timeless elegance. The front entrance is set apart from the road by a sweeping circular drive bordered by private hedges and mature trees. Upon entering the stately, two-story foyer with a 25' ceiling, bridal staircase, black and white marble floor, formal

    Katharine Hackett @properties Christie's International Real Estate

    32 Woodley Rd, Winnetka, IL 60093
  • /50

    $2,190,000

    • 4 Beds
    • 4 Baths
    • 4,460 Sq Ft

    803 Pine St, Winnetka, IL 60093

    Absolute perfection in the heart of East Winnetka! Completed in 2022, this contemporary two-story masterpiece offers the perfect combination of luxury and convenience. Situated on a beautifully landscaped lot, the home is adorned with Brazilian Ipe Norwegian board siding, triple-pane windows, and a stunning modern front door, all adding to its striking curb appeal. The open-concept first floor

    Michael Kelly Compass

    803 Pine St, Winnetka, IL 60093
  • /21

    $892,500

    • 4 Beds
    • 1.5 Baths
    • 1,355 Sq Ft

    979 Vine St, Winnetka, IL 60093

    Winnetka introduces a nostalgic bungalow perfectly appointed between Hubbard elementary school, shops, entertainment and restaurants! A charming fenced in yard allures guests to a beautiful entry where the floor plan unveils an open concept with a sprawling family room filled with an abundance of natural light. The family overshadows a separate sitting room with a gorgeous brick fireplace and

    Rob Morrison Coldwell Banker Realty

    979 Vine St, Winnetka, IL 60093
  • /26

    $4,495,000 New Construction

    • 5 Beds
    • 7 Baths
    • 7,500 Sq Ft

    518 Elder Ln, Winnetka, IL 60093

    Stunning new construction transitional home with approximately 7,500 square feet of meticulously finished space, the home is located on one of the most picturesque streets in East Winnetka in an unbeatable location. The home is close to town, walking distance to the beach, schools and train. This home features 6 bedrooms, 7 full baths, a show room worthy kitchen with luxury appliances including

    Matan Aharoni Coldwell Banker Realty

    518 Elder Ln, Winnetka, IL 60093
  • /59

    $6,499,900

    • 9 Beds
    • 11 Baths
    • 9,592 Sq Ft

    Unlisted Address

    After a sun-soaked day at the beach and a quick stroll home, the evening unfolds effortlessly-fire up the BBQ, let the spa heat up, and get ready for a magical night swim under the stars. This is the perfect way to end the perfect day at this incredible and rare East Kenilworth compound. A stunning shingle-style beauty just fully outfitted with a brand new cedar composite roof is tucked away on

    Jena Radnay @properties Christie's International Real Estate

    Unlisted Address
  • /29

    $5,725,000 New Construction

    • 5 Beds
    • 8 Baths
    • 8,300 Sq Ft

    515 Roslyn Rd, Kenilworth, IL 60043

    Life is Short. Seize the rare opportunity to custom build your dream home on one of the most coveted and private streets in East Kenilworth-just steps from Sears School and New Trier HS, the beach, and town/train. Construction is already underway, with completion projected for the end of 2026. This exceptional transitional-style residence blends timeless elegance with modern luxury, featuring a

    Steven Aisen @properties Christie's International Real Estate

    515 Roslyn Rd, Kenilworth, IL 60043
  • /6

    $2,395,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 4,971 Sq Ft

    150 Linden Ave, Glencoe, IL 60022

    Proposed New Construction~ Sophisticated farmhouse with a welcoming front porch with a metal roof and approximately 4500 sq ft of finished space situated on a deep 55 X 180 lot. Get in while there is still time to customize and make this your dream home. Super desirable location with close proximity to town, parks, schools, public transportation and the beach for both Hubbard Woods and Glencoe.

    Susan Maman @properties Christie's International Real Estate

    150 Linden Ave, Glencoe, IL 60022
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