Winnetka, IL Homes for Sale

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  /63

  $2,250,000

  Open Sat 2PM - 4PM

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

  42 Woodley Rd, Winnetka, IL 60093

  Rarely available first floor primary! 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. Owner extremely

  Peggy Lewis @properties Christie's International Real Estate

  42 Woodley Rd, Winnetka, IL 60093
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  /46

  $2,499,000

  Open Sun 12PM - 2PM

  • 4 Beds
  • 4.5 Baths
  • 3,610 Sq Ft

  1192 Chatfield Rd, Winnetka, IL 60093

  This is the opportunity buyers wait for. An architecturally significant Hubbard Woods Georgian that could never be duplicated today for anywhere near this cost. Perfectly positioned on one of the neighborhood's most coveted cul-de-sac streets, this distinctive home showcases extraordinary vintage details paired with over $1.2 million in thoughtful renovations and infrastructure improvements. Step

  Jena Radnay @properties Christie's International Real Estate

  1192 Chatfield Rd, Winnetka, IL 60093
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  /55

  $1,295,000

  • 4 Beds
  • 2.5 Baths
  • 3,362 Sq Ft

  1110 Elm St, Winnetka, IL 60093

  Timeless Elegance Meets Modern Luxury with this prime Winnetka home on a large corner lot. Discover the perfect blend of historic character and contemporary living in this meticulously maintained residence. From the moment you step inside, rich vintage craftsmanship takes center stage, highlighted by striking coffered ceilings, multiple cozy fireplaces, and an exquisite built-in buffet. At the

  Brian Grienenberger Baird & Warner

  1110 Elm St, Winnetka, IL 60093
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  /53

  $4,949,000

  • 6 Beds
  • 7 Baths
  • 13,000 Sq Ft

  320 Woodley Rd, Winnetka, IL 60093

  Perfectly nestled on one of Winnetka's finest enclaves, this stately 6-bedroom, 5.2-bath Georgian estate offers a rare fusion of architectural elegance, exceptional craftsmanship, and resort-style amenities. Set on nearly an acre of meticulously manicured grounds, the estate is introduced by a sweeping circular drive that highlights the home's classic brick facade, brand-new DaVinci slate roof,

  Susan Maman @properties Christie's International Real Estate

  320 Woodley Rd, Winnetka, IL 60093
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  /27

  $849,900

  $25K PRICE DROP Pending

  • 3 Beds
  • 3 Baths

  444 Oakdale Ave, Glencoe, IL 60022

  Classic brick home filled with timeless character, generous living spaces and thoughtful updates on one of Glencoe's desirable tree-lined streets. A welcoming arched foyer opens to a gracious living room highlighted by refinished hardwood floors, a wood-burning fireplace and a charming office nook. The formal dining room flows seamlessly into a bright enclosed porch overlooking the backyard,

  Peter Moore Baird & Warner

  444 Oakdale Ave, 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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