Winnetka, IL Homes for Sale

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  /72

  $2,250,000

  • 4 Beds
  • 6 Baths
  • 4,225 Sq Ft

  42 Woodley Rd, Winnetka, IL 60093

  Rarely available unique mid-century contemporary in the heart of Winnetka. Your own private paradise with a flowing interior perfect for entertaining! Soaring teak ceilings add to the Aspen style influence. Tons of windows look out to the gorgeous landscaped grounds enhanced by a pool and gazebo. This home has been beautifully maintained by the current owners.

  Peggy Lewis @properties Christie's International Real Estate

  42 Woodley Rd, Winnetka, IL 60093
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  /24

  $975,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 2,427 Sq Ft

  882 Willow Rd, Winnetka, IL 60093

  Prepare to be captivated by this picture-perfect 4-bedroom, 3.1-bathroom colonial-cottage home, meticulously updated with high-end designer finishes throughout. Boasting incredible curb appeal with its deep blue siding, crisp white trim, and brick-paver paths, this turn-key residence seamlessly blends historic architectural character with contemporary luxury. Inside, an airy, light-filled layout

  Karen Arenson Engel & Voelkers Chicago North Shore

  882 Willow Rd, Winnetka, IL 60093
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  /49

  $2,795,000

  • 6 Beds
  • 4.5 Baths
  • 6,900 Sq Ft

  127 Glenwood Ave, Winnetka, IL 60093

  Nestled in one of the most sought-after and convenient locations in Winnetka/Hubbard Woods, this exceptional stone residence blends timeless architecture, refined design, and modern comfort just moments from town, the train, and Lake Michigan. Expertly crafted in 2006 by Adamczyk Fine Homes and Interiors, the home showcases nearly 7,000 square feet of beautifully designed living space across

  Marina Carney Compass

  127 Glenwood Ave, Winnetka, IL 60093
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  /71

  $3,200,000

  Pending

  • 6 Beds
  • 6 Baths
  • 7,914 Sq Ft

  100 Old Green Bay Rd, Winnetka, IL 60093

  Exceptional architecture meets thoughtful in this spectacular home with original design by Thomas Eddy Tallmadge and renovation design by Paul Konstant, all perfectly set in a park-like setting just steps from the shops, restaurants, train, and Hubbard Woods park and town. Four levels of beautifully imagined living spaces invite both grand entertaining and relaxed everyday living. Step inside the

  Joanne Hudson Compass

  100 Old Green Bay Rd, Winnetka, IL 60093
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  /48

  $2,245,000

  $50K PRICE DROP Pending

  • 5 Beds
  • 4.5 Baths
  • 4,390 Sq Ft

  1159 Chatfield Rd, Winnetka, IL 60093

  Blending timeless elegance with modern sophistication, this stunning 2016 Winnetka home feels better than new. Designed for light, flow, and effortless living, it features 10-foot ceilings, white oak floors, and expansive windows that fill each room with warmth. The gourmet kitchen showcases custom cabinetry, large island, and professional appliances is perfect for everyday living and

  Jason Rowland Compass

  1159 Chatfield Rd, Winnetka, IL 60093
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  /58

  $2,395,000

  Pending

  • 6 Beds
  • 5.5 Baths
  • 4,837 Sq Ft

  1482 Edgewood Ln, Winnetka, IL 60093

  Nestled on a charming, quiet, tree-lined street in Winnetka's highly sought-after Hubbard Woods neighborhood, 1482 Edgewood Lane offers the perfect blend of timeless style, modern functionality, and an unbeatable North Shore location-just steps from Nick Corwin Park, and less than a mile to town, train, and schools. Built in 2015, this stunning Nantucket-inspired newer construction home is

  Kathryn Moor Compass

  1482 Edgewood Ln, Winnetka, IL 60093
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  /36

  $1,298,000

  $202K PRICE DROP Pending

  • 4 Beds
  • 3.5 Baths
  • 3,200 Sq Ft

  90 Linden Ave, Glencoe, IL 60022

  Traditional colonial meets resort style living. Set back from Linden Avenue for space and privacy. Light and bright interior with upgraded finishes and custom details throughout. This charming 4-bedroom, 3.5 bath home is nestled in a highly sought-after neighborhood. Enjoy the perfect blend of peaceful retreat and easy access, just a short stroll to vibrant Hubbard Woods, charming downtown

  Suzanne Beu Jameson Sotheby's International Realty

  90 Linden Ave, Glencoe, IL 60022
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  /18

  $849,000

  $76K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 1,850 Sq Ft

  611 Roger Ave, Kenilworth, IL 60043

  Bright, sunny, and full of potential, this mid-century modern home brings an easy, elevated lifestyle to a convenient Kenilworth location. Thoughtfully updated and deceptively spacious, it lives far larger than it appears from the outside. The main level is designed for both everyday comfort and effortless living, featuring a welcoming living room with a gas fireplace and a dining room that opens

  Catherine King Compass

  611 Roger Ave, Kenilworth, IL 60043
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  /76

  $2,485,000

  Pending

  • 5 Beds
  • 7 Baths
  • 6,323 Sq Ft

  605 Skokie Ln S, Glencoe, IL 60022

  This beautifully refined brick home set on a half acre on a quiet cul-de-sac delivers the quality and space that discerning buyers covet. The floor plan is exceptional, with distinct spaces designed for the way people want to live. A two-story foyer filled with light sets the stage, opening to a formal living room and dining room, each with tray ceilings. The dramatic two-story family room with a

  Howard Meyers Compass

  605 Skokie Ln S, Glencoe, IL 60022
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  /20

  $16,750,000

  • 7 Beds
  • 8.5 Baths
  • 17,000 Sq Ft

  501 Sheridan Rd, Kenilworth, IL 60043

  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

  Milena Birov @properties Christie's International Real Estate

  501 Sheridan Rd, Kenilworth, IL 60043
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  /31

  $1,150,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,219 Sq Ft

  491 Drexel Ave, Glencoe, IL 60022

  Situated in the heart of Glencoe's most desirable neighborhood, this beautiful 4-bedroom, 2.1-bathroom home offers a rare blend of modern luxury and timeless elegance. Perched on a massive corner wooded lot, the property is not only beautiful and tranquil but also creates options galore for expansion should one choose. The main level of the home features hardwood floors, a gracious living room

  Connie Grunwaldt @properties Christie's International Real Estate

  491 Drexel Ave, Glencoe, IL 60022
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  /22

  $1,200,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  724 Maclean Ave, Kenilworth, IL 60043

  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-in bookshelves. The floor plan includes a formal dining room with built-in corner hutches and a kitchen that opens to a south-facing family room. The

  Joseph Nash @properties Christie's International Real Estate

  724 Maclean Ave, Kenilworth, IL 60043

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