Winnetka, IL Homes

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  /50

  $2,499,900

  Pending

  • 6 Beds
  • 6 Baths
  • 5,458 Sq Ft

  406 Woodley Woods, Winnetka, IL 60093

  MULTIPLE OFFERS! HIGHEST AND BEST DUE 5PM ON 4/24/26! Set at the end of a quiet, private cul-de-sac on a rare acre lot, this custom-built Georgia marble home with an inground pool showcases timeless elegance and exceptional craftsmanship in the Woodley neighborhood of Winnetka. A gracious foyer with stained glass double entry doors, marble tile floors, fresh paint, and a sparkling crystal

  Jason Wagner Greystone Realty

  406 Woodley Woods, Winnetka, IL 60093
• Explore Winnetka

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  /7

  Starting at $1,870 Per Month

  • 1 Bed

  458 Winnetka Ave, Winnetka, IL 60093

  Renovated 1 bedroom in a well run vintage two story building! . Hardwood floors. Bright apartment w large picture windows, Eat in kitchen with dishwasher and microwave. Large bedroom (with closet) fitting for even a king size bed. Large bathroom.Heat and water included. Clean and tidy laundry room in building plus bike storage. Classic, original details combine with fresh updates to

  460 Winnetka Ave.

  458 Winnetka Ave, Winnetka, IL 60093
• 

  

  

  /58

  $2,750,000

  Sold Feb 13, 2026

  205 Scott Ave, Winnetka, IL 60093

  • 5 Beds
  • 5 Baths
  • 6,162 Sq Ft
  • Built 1933

  Last Sold Summary

  • 4% Below List Price
  • $446/SF
  • 21 Days On Market

  Current Estimated Value $2,713,641

  Last Listing Agent Nicole Hajdu Baird & Warner

  205 Scott Ave, Winnetka, IL 60093
• 

  

  

  /33

  Est $1,474,428

  Not Listed For Sale

  1413 Tower Rd, Winnetka, IL 60093

  • 4 Beds
  • 4 Baths
  • 3,029 Sq Ft
  • Built 1930

  1413 Tower Rd, Winnetka, IL 60093

  Last Sold Summary

  • 5 Days On Market
• 

  

  

  /19

  $360,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,360 Sq Ft

  134 Green Bay Rd Unit 104, Winnetka, IL 60093

  Sun-drenched mornings define this coveted two-bedroom, two-bathroom residence. Located in a premier building within a highly sought-after location, this home welcomes you with a bright, cheerful, thoughtful layout. The east-facing exposure ensures the living spaces are bathed in natural light, while the charming private balcony offers the perfect spot for a morning coffee or an evening breeze.

  Dinny Dwyer Compass

  134 Green Bay Rd Unit 104, Winnetka, IL 60093
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  /2

  $1,770 Per Month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  916 Green Bay Rd Unit 918-2L, Winnetka, IL 60093

  Charming 1 bedroom apartment in Winnetka! Unit features hardwood floors, spacious living area. Electric heat. Close to Metra, Hubbard Woods Park, grocery, restaurants and more! Presented by Fulton Grace, Chicago IL. *Pictures may be of a similar unit in building.

  916 Green Bay Rd Unit 918-2L, Winnetka, IL 60093
• 

  /2

  $875,000

  Sold Jan 12, 2026

  1288 Sunview Ln, Winnetka, IL 60093

  • 5 Beds
  • 3.5 Baths
  • 2,714 Sq Ft
  • Built 1955

  Last Sold Summary

  • 27% Below List Price
  • $322/SF
  • 158 Days On Market

  Current Estimated Value $1,168,777

  Last Listing Agent Dinny Dwyer Compass

  1288 Sunview Ln, Winnetka, IL 60093
• 

  

  /23

  Est $1,040,757

  Not Listed For Sale

  283 Ridge Ave, Winnetka, IL 60093

  • 3 Beds
  • 2 Baths
  • 2,008 Sq Ft
  • Built 1926

  283 Ridge Ave, Winnetka, IL 60093

  Last Sold Summary

  • 3 Days On Market
• 

  

  /84

  $3,850,000

  Pending

  • 7 Beds
  • 5.5 Baths

  605 Arbor Vitae Rd, Winnetka, IL 60093

  A RARE OPPORTUNITY...in the HEART of East Winnetka, this iconic home is among the Village's most admired residences! Commanding an elevated setting atop Arbor Vitae, the magnificent home was designed by renowned architects Otis & Clark and has earned its grand reputation as Winnetka's own "Castle on the Hill." It boasts one of the most exceptional backyard retreats! Featured in Luxe Magazine and

  Megan Panje-Wilson Jameson Sotheby's International Realty

  605 Arbor Vitae Rd, Winnetka, IL 60093
• 

  

  /13

  $1,770 Per Month

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Condo for Rent

  918 Green Bay Rd Unit 3E, Winnetka, IL 60093

  Book a tour by copying this link into your browser. PLEASE MAKE SURE TO INCLUDE THE ADDRESS & UNIT # DURING BOOKING TO CONFIRM AVAILABILITY. Welcome to your next home in the charming district of Winnetka, IL! This delightful property offers a comfortable living space near a variety of local amenities, including popular restaurants and department stores. Enjoy the convenience of nearby

  918 Green Bay Rd Unit 3E, Winnetka, IL 60093
• 

  

  /15

  $1,675,000

  Sold Aug 28, 2025

  917 Willow Rd, Winnetka, IL 60093

  • 4 Beds
  • 5 Baths
  • 4,352 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $385/SF
  • 38 Days On Market

  Current Estimated Value $1,750,000

  Last Listing Agent Grace Goro Compass

  917 Willow Rd, Winnetka, IL 60093
• 

  

  /16

  Est $702,634

  Not Listed For Sale

  518 Winnetka Ave Unit 203, Winnetka, IL 60093

  • 2 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • Built 2004

  518 Winnetka Ave Unit 203, Winnetka, IL 60093

  Last Sold Summary

  • 4 Days On Market
• 

  

  /18

  $5,975,000

  New Construction

  • 7 Beds
  • 8.5 Baths
  • 11,000 Sq Ft

  455 Sheridan Rd, Winnetka, IL 60093

  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

  Milena Birov @properties Christie's International Real Estate

  455 Sheridan Rd, Winnetka, IL 60093
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  /13

  $1,595 Per Month

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Condo for Rent

  918 Green Bay Rd Unit 2F, Winnetka, IL 60093

  Book a tour by copying this link into your browser. PLEASE MAKE SURE TO INCLUDE THE ADDRESS & UNIT # DURING BOOKING TO CONFIRM AVAILABILITY. Welcome to your ideal rental home in the picturesque district of Winnetka, IL. This charming property offers a perfect blend of comfort and convenience, making it a great choice for your next move. Located within walking distance to Tower Road

  918 Green Bay Rd Unit 2F, Winnetka, IL 60093
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  /49

  $1,520,000

  Sold Aug 12, 2025

  605 Lincoln Ave, Winnetka, IL 60093

  • 4 Beds
  • 5 Baths
  • 3,000 Sq Ft
  • Built 1914

  Last Sold Summary

  • 17% Above List Price
  • $507/SF
  • 5 Days On Market

  Current Estimated Value $1,573,435

  Last Listing Agent Patricia Skirving Compass

  605 Lincoln Ave, Winnetka, IL 60093
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  /32

  Est $1,014,744

  Not Listed For Sale

  154 Glenwood Ave, Winnetka, IL 60093

  • 3 Beds
  • 2 Baths
  • 2,420 Sq Ft
  • Built 1919

  154 Glenwood Ave, Winnetka, IL 60093

  Last Sold Summary

  • 4 Days On Market
• 

  

  /21

  $2,785,000

  • 6 Beds
  • 5.5 Baths

  82 Woodley Rd, Winnetka, IL 60093

  Tucked away on one of Winnetka's most prestigious and serene lanes, this estate offers a rare blend of timeless North Shore elegance and a sense of true sanctuary. This isn't just a home; it's a sprawling residence designed for a lifestyle of both grand-scale entertaining and quiet, sun-drenched mornings. From the moment you pull up the winding drive, the home's commanding presence and lush,

  Michael Mitchell @properties Christie's International Real Estate

  82 Woodley Rd, Winnetka, IL 60093
• 

  

  /13

  $1,930 Per Month

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Condo for Rent

  918 Green Bay Rd Unit 3G, Winnetka, IL 60093

  Book a tour by copying this link into your browser. PLEASE MAKE SURE TO INCLUDE THE ADDRESS & UNIT # DURING BOOKING TO CONFIRM AVAILABILITY. Welcome to your future home in the charming district of Winnetka, IL. This inviting property is perfectly situated near delightful restaurants and convenient department stores, making it an ideal spot for dining and shopping enthusiasts. Families

  918 Green Bay Rd Unit 3G, Winnetka, IL 60093
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  /5

  $5,600,000

  Sold Feb 26, 2026

  674 Hill Rd, Winnetka, IL 60093

  • 6 Beds
  • 6 Baths
  • 9,000 Sq Ft
  • Built 1916

  Last Sold Summary

  • 32% Above List Price
  • $622/SF
  • 16 Days On Market

  Current Estimated Value $5,255,345

  Last Listing Agent Lori Neuschel @properties Christie's International Real Estate

  674 Hill Rd, Winnetka, IL 60093
• 

  

  /20

  Est $886,342

  Not Listed For Sale

  812 Oak St Unit 201, Winnetka, IL 60093

  • 2 Beds
  • 2 Baths
  • 1,745 Sq Ft
  • Built 1997

  812 Oak St Unit 201, Winnetka, IL 60093

  Last Sold Summary

  • 3 Days On Market
• 

  

  /26

  $625,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,680 Sq Ft

  680 Green Bay Rd Unit 306, Winnetka, IL 60093

  Classic Gold Coast boutique building energy-but reimagined for Winnetka living, with western sunset views, a beautifully renovated interior, and that rare walk-to-everything lifestyle buyers chase for years. Tucked inside an intimate boutique building in one of Winnetka's most coveted locations, this stunning residence lives like the perfect blend of sophistication, comfort, and effortless

  Connie Dornan @properties Christie's International Real Estate

  680 Green Bay Rd Unit 306, Winnetka, IL 60093
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  /10

  $1,595 Per Month

  • Studio
  • 1 Bath
  • 400 Sq Ft
  • Condo for Rent

  918 Green Bay Rd Unit 3C, Winnetka, IL 60093

  Actual Unit # *3C*Book a tour by copying this link into your browser. PLEASE MAKE SURE TO INCLUDE THE ADDRESS & UNIT # DURING BOOKING TO CONFIRM AVAILABILITY. Comfortable and well-maintained apartment located in a convenient Chicago-area neighborhood. This unit offers a functional layout, spacious living areas, and easy access to shopping, dining, public transportation, parks, and

  918 Green Bay Rd Unit 3C, Winnetka, IL 60093
• 

  

  /35

  $1,100,000

  Sold Aug 01, 2025

  886 Willow Rd, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 2,534 Sq Ft
  • Built 1910

  Last Sold Summary

  • $434/SF
  • 19 Days On Market

  Current Estimated Value $1,187,330

  Last Listing Agent Carly Jones Engel & Voelkers Chicago North Shore

  886 Willow Rd, Winnetka, IL 60093
• 

  

  /22

  Est $1,191,239

  Not Listed For Sale

  812 Oak St Unit 200, Winnetka, IL 60093

  • 3 Beds
  • 2.5 Baths
  • 2,300 Sq Ft
  • Built 1997

  812 Oak St Unit 200, Winnetka, IL 60093

  Last Sold Summary

  • 5 Days On Market
• 

  

  /67

  $7,999,900

  • 6 Beds
  • 9 Baths
  • 10,588 Sq Ft

  919 Hill Rd, Winnetka, IL 60093

  An extraordinary "boutique hotel" living experience, impeccably situated in the heart of Winnetka. Beyond a stately solid-iron gate adorned with gold medallion accents lies a private sanctuary just 18 miles from Chicago and less than half a mile from the sandy shores of Lake Michigan. Evoking the glamour and grandeur of a Roaring Twenties estate, this remarkable residence channels the elegance of

  Jena Radnay @properties Christie's International Real Estate

  919 Hill Rd, Winnetka, IL 60093
• 

  

  /9

  $1,885 Per Month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  733 Elm St Unit 302, Winnetka, IL 60093

  Book a tour by copying this link into your browser. PLEASE MAKE SURE TO INCLUDE THE ADDRESS & UNIT # DURING BOOKING TO CONFIRM AVAILABILITY. Welcome to a charming rental opportunity in the desirable district of Winnetka, IL. This thoughtfully located property offers a serene living experience near several delicious restaurants and convenient department stores, making daily errands a

  733 Elm St Unit 302, Winnetka, IL 60093
• 

  

  /52

  $1,900,000

  Sold Jul 10, 2025

  475 Maple St, Winnetka, IL 60093

  • 4 Beds
  • 5 Baths
  • 3,524 Sq Ft
  • Built 1888

  Last Sold Summary

  • 5% Below List Price
  • $539/SF
  • 19 Days On Market

  Current Estimated Value $1,977,850

  Last Listing Agent Paige Dooley Compass

  475 Maple St, Winnetka, IL 60093
• 

  

  /22

  Est $597,243

  Not Listed For Sale

  720 Green Bay Rd Unit 3B, Winnetka, IL 60093

  • 2 Beds
  • 2 Baths
  • 1,676 Sq Ft
  • Built 2007

  720 Green Bay Rd Unit 3B, Winnetka, IL 60093

  Last Sold Summary

  • 38 Days On Market
• 

  

  /53

  $5,149,000

  $200K PRICE DROP

  • 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
• 

  

  /10

  $1,595 Per Month

  • Studio
  • 1 Bath
  • 500 Sq Ft
  • Condo for Rent

  918 Green Bay Rd Unit 918 Green Bay Rd, Winnetka, IL 60093

  Property Id: 2620747Charming studio apartment in the heart of Winnetka! This unit features a spacious bathroom, hardwood floors, and shared washer/dryer. The kitchen includes a refrigerator and oven. Pets allowed with restrictions. Rent includes garbage, sewage, and water. Don't miss out on this cozy living space! Available for rent starting June 22, 2026. Schedule a viewing today!

  918 Green Bay Rd Unit 918 Green Bay Rd, Winnetka, IL 60093
• 

  /2

  $1,890,008

  Sold May 18, 2026

  67 Brier St, Winnetka, IL 60093

  • 5 Beds
  • 6 Baths
  • 4,200 Sq Ft
  • Built 2026

  Last Sold Summary

  • 3% Below List Price
  • $450/SF
  • 34 Days On Market

  Current Estimated Value $1,875,148

  Last Listing Agent Nehru Arunasalam @properties Christie's International Real Estate

  67 Brier St, Winnetka, IL 60093
• 

  

  /13

  Est $516,383

  Not Listed For Sale

  720 Green Bay Rd Unit 2E, Winnetka, IL 60093

  • 2 Beds
  • 2 Baths
  • 1,216 Sq Ft
  • Built 2007

  720 Green Bay Rd Unit 2E, Winnetka, IL 60093

  Last Sold Summary

  • 8 Days On Market
• 

  

  /58

  $2,099,000

  Pending

  • 5 Beds
  • 5.5 Baths

  920 Pine Tree Ln, Winnetka, IL 60093

  Easy living at its best! Discerning updates and renovations combine with impeccable maintenance to create this exceptional home with the ease of one-floor living with outstanding design, gracious proportions, and an effortless flow throughout. Set on a gorgeous 4/10 acre property, the grounds are a true private retreat, featuring lush, professional landscaping, mature trees, colorful plantings,

  Joanne Hudson Compass

  920 Pine Tree Ln, Winnetka, IL 60093
• 

  

  /5

  $1,665 Per Month

  • Studio
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  733 Elm St Unit 301, Winnetka, IL 60093

  Actual Unit # *301*Book a tour by copying this link into your browser. PLEASE MAKE SURE TO INCLUDE THE ADDRESS & UNIT # DURING BOOKING TO CONFIRM AVAILABILITY. Comfortable and well-maintained apartment located in a convenient Chicago-area neighborhood. This unit offers a functional layout, spacious living areas, and easy access to shopping, dining, public transportation, parks,

  733 Elm St Unit 301, Winnetka, IL 60093
• 

  

  /56

  $2,450,000

  Sold Oct 06, 2025

  107 Woodley Rd, Winnetka, IL 60093

  • 5 Beds
  • 4.5 Baths
  • 5,001 Sq Ft
  • Built 1956

  Last Sold Summary

  • 14% Above List Price
  • $490/SF
  • 8 Days On Market

  Current Estimated Value $2,489,178

  Last Listing Agent Jena Radnay @properties Christie's International Real Estate

  107 Woodley Rd, Winnetka, IL 60093
• 

  

  /41

  Est $727,319

  Not Listed For Sale

  720 Green Bay Rd Unit 2D, Winnetka, IL 60093

  • 3 Beds
  • 2.5 Baths
  • 1,931 Sq Ft
  • Built 2007

  720 Green Bay Rd Unit 2D, Winnetka, IL 60093

  Last Sold Summary

  • 120 Days On Market
• 

  

  /45

  $2,199,000

  Pending

  • 5 Beds
  • 5.5 Baths
  • 3,426 Sq Ft

  1258 Scott Ave, Winnetka, IL 60093

  Beautifully renovated and thoughtfully reimagined, this exceptional brick and stucco Colonial located in the heart of Hubbard Woods sits on an expanded 64 X 160 parcel, blending timeless architecture with today's most desired amenities and refined finishes. A total interior renovation completed in 2004 with added exterior renovation in 2006 and 2017 redesigns, transformed the home into a

  Sara Sullivan Compass

  1258 Scott Ave, Winnetka, IL 60093
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  /14

  $2,150 Per Month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  545 Chestnut St Unit 545-301, Winnetka, IL 60093

  Renovated 1 bedroom apartment in Winnetka! Unit features hardwood floors, updated kitchen & bath, separate dining area, laundry in-unit. Pet friendly building. Great location close to Dwyer Park, Metra, restaurants and shopping! Presented by Fulton Grace, Chicago IL.*Pictures may be of a similar unit in building.

  545 Chestnut St Unit 545-301, Winnetka, IL 60093
• 

  

  /59

  $2,000,000

  Sold Apr 01, 2026

  1215 Spruce St, Winnetka, IL 60093

  • 4 Beds
  • 5 Baths
  • 3,633 Sq Ft
  • Built 1955

  Last Sold Summary

  • $551/SF
  • 6 Days On Market

  Current Estimated Value $2,015,624

  Last Listing Agent Megan Mawicke Jameson Sotheby's International Realty

  1215 Spruce St, Winnetka, IL 60093
• 

  /2

  Est $3,771,045

  Not Listed For Sale

  104 Longmeadow Rd, Winnetka, IL 60093

  • 7 Beds
  • 8.5 Baths
  • 12,998 Sq Ft
  • Built 2008

  104 Longmeadow Rd, Winnetka, IL 60093

  Last Sold Summary

  • 91 Days On Market

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