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View All Winnetka Homes for Sale _ Updated Every 15 minutes

$250,000 - $500,000 $500,000 - $750,000 $750,000 - $1,000,000
$1,000,000 - $2,000,000 $2,000,000 - $3,000,000 $3,000,000 - $5,000,000
$5,000,000 - $10,000,000
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555 Cherry Street, Winnetka, IL - $1,475,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
  • 5,625 SQFT
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Vintage Beauty With Show Stopping Curb Appeal And Amazing Street Presence Screams Welcome Home! Large Scale Rooms, Hardwood Flooring, Tons Of Windows Bringing In Natural Light; This Home Is Loaded With Charming Details, High Ceilings, And A Flexib...

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Photo of Listing #10742787

1235 Scott Avenue, Winnetka, IL - $1,395,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 4,546 SQFT
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This Luxurious Built (2003) French Tudor 5+1 Bedroom, 5.2 Bath Was Custom Designed By Greystone Builders. Old World Charm, Including 10 Foot+ Coffered Ceilings, Crown Moldings, Hardwood Floors, Arched Doorways, Decorative Finishes, 3 Fireplaces & ...

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Photo of Listing #10809407

844 Prospect Avenue, Winnetka, IL - $1,299,000

Residential, Detached Single
  • 6 Beds
  • 5 Baths
  • 4,500 SQFT
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Renovate And Make This Home Your Own! A Delightful Winnetka Charmer, Ideally Situated On An Oversized Corner Lot 100 X 150 Located Close To Hw Town, Train And The Beach. Character Abounds: Complete With Flowing Floor Plan, Sleeping Porches, Sunroo...

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250 Poplar Street, Winnetka, IL - $1,249,000

Residential, Detached Single
  • 5 Beds
  • 4 Baths
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This Idyllic Home Has 5 Bedrooms And 3.1 Baths In Sought After East Winnetka Corner Lot. Home Boasts A 2019 Award Winning Two Bedroom Addition, New Mudroom, New First Floor Bathroom And Attached Two Car Garage. Step Into Perfection As You Are Gree...

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132 Fuller Lane, Winnetka, IL - $1,150,000

Residential, Detached Single
  • 5 Beds
  • 4 Baths
  • 4,438 SQFT
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Fantastic East Winnetka Location. Charming Nantucket Style With A Fresh Vibe. Sunny 5 Br Retreat On Premier Street Steps To Lake, Train, Schools, Parks & Plaza Del Lago. Stylized Renovation/addition To A Colonial Classic By Architect-owner. Open, ...

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1000 Willow Road, Winnetka, IL - $1,149,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 3,426 SQFT
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Winnetka's Perfect Location! Walk To The Award-winning Crow Island, Skokie And Washburne Schools (k-8), Shopping, Dining, Coffee Shops, And The Metra. Newer Construction Built With Today's Busy Family Lifestyle In Mind. Sun-filled Spaces Include...

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340 Woodland Avenue, Winnetka, IL - $1,100,000

Residential, Detached Single
  • 6 Beds
  • 6 Baths
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Attractive Red Brick Georgian In Sought After East Location Near Schools, Train, Town And Beaches! Spacious Living Room Features Fireplace And Hardwood Floors. Sun-filled Family Room Opens To Formal Dining Room. Bright Airy White Kitchen Includ...

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512 Orchard Lane, Winnetka, IL - $1,100,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
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Gorgeous English Brick Home On A Tree Lined Street In Fabulous East Winnetka. Main Floor Has Great Flow For Entertaining Featuring A Large Living Room With A Fireplace And An Attached Sun Filled Florida Room. A Separate Dining Room Opens Up To An ...

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579 Hill Terrace, Winnetka, IL - $1,099,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 3,674 SQFT
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This Beautiful, Updated, Classic Center Entry Brick 4 Bedroom Colonial Home Is The Epitome Of Fine Design, Detail & Elegance. Gracious Entry Sandwiches A Formal Dining & Living Room With A Stunning Mantel Over The Wood Burning/gas Starter Marble ...

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Photo of Listing #11018892

1158 Oak Street, Winnetka, IL - $1,049,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
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Exactly What You Are Looking For On The Tree Streets! Beautiful Center Entry Red-brick Colonial On Oversized Lot Close To Schools, Park District And Town! Private First Floor Office, Awesome Circular Floor Plan, Hardwood Floors And Crown Molding A...

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Midwest Real Estate Data LLC Logo 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 April 11th, 2021 at 10:00am CDT.