Winnetka, IL Homes

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  /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
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• 

  

  

  /20

  $1,795

  Total Monthly Price

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

  701 Elm St Unit J04P, Winnetka, IL 60093

  701 Elm St Unit J04P, Winnetka, IL 60093
• 

  

  

  /7

  $2,350,000

  Sold Oct 24, 2025

  466 Chestnut St, Winnetka, IL 60093

  • 5 Beds
  • 5.5 Baths
  • 4,433 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $530/SF

  Current Estimated Value $2,357,752

  Last Listing Agent Robert Milkowski Berger & Co. Realtors Ltd

  466 Chestnut St, Winnetka, IL 60093
• 

  

  /2

  Est $4,079,650

  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

  Last Listing Agent Linda Martin Coldwell Banker Realty
• 

  

  

  /41

  $1,795,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 4,356 Sq Ft

  180 Westview Rd, Winnetka, IL 60093

  BRAND NEW ROOF JUST INSTALLED WITH TRANSFERABLE WARRANTY!! Beautifully maintained home offering over 4,300 square feet above grade on a rare 0.53-acre corner lot in a sought-after Winnetka location. The centerpiece of the home is the dramatic main living space featuring soaring vaulted cathedral ceilings, abundant natural light, and an impressive open feel that creates an immediate sense of scale

  Cody McGuire @properties Commercial

  180 Westview Rd, Winnetka, IL 60093
• 

  

  /27

  $1,545 - $1,670

  Total Monthly Price

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

  924 Green Bay Rd, Winnetka, IL 60093

  924 Green Bay Rd, Winnetka, IL 60093
• 

  

  /29

  $1,103,000

  Sold May 13, 2026

  1523 Tower Rd, Winnetka, IL 60093

  • 4 Beds
  • 3 Baths
  • 2,503 Sq Ft
  • Built 1955

  Last Sold Summary

  • 1% Above List Price
  • $441/SF
  • 5 Days On Market

  Current Estimated Value $1,140,449

  Last Listing Agent Mary Grant @properties Christie's International Real Estate

  1523 Tower Rd, Winnetka, IL 60093
• 

  

  /5

  Est $3,593,967

  Not Listed For Sale

  269 Woodlawn Ave, Winnetka, IL 60093

  • 5 Beds
  • 6.5 Baths
  • 7,400 Sq Ft
  • Built 2024

  269 Woodlawn Ave, Winnetka, IL 60093

  Last Sold Summary

  • 52 Days On Market

  Last Listing Agent Derek Schiller Derek E. Schiller
• 

  

  /45

  $1,799,000

  Pending

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

  922 Ash St, Winnetka, IL 60093

  Exceptional 4-bedroom, 2.1-bath home on Winnetka's coveted Tree Streets, offering an expansive third-floor loft and situated on a 50' x 187' deep lot. Blending timeless charm with thoughtfully designed living spaces, this home is filled with natural light, soaring ceilings, and beautiful hardwood floors throughout. A welcoming covered front porch leads into gracious living and dining rooms, while

  Selma Nemeth @properties Christie's International Real Estate

  922 Ash St, Winnetka, IL 60093
• 

  

  /18

  $1,595 Per Month

  • 1 Bath
  • 400 Sq Ft
  • Apartment for Rent

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

  Phenomenal studio in Winnetka features rehabbed kitchen with stainless steel appliances, dishwasher, spacious living area, great closet space, hardwood floors throughout, rehabbed bathroom, laundry in unit, and pets are welcome. Steps to Hubbard Woods Metra stop, and a block to Tower Road Park Beach!

  Berthene Christos Urban Abodes Chicago

  918 Green Bay Rd Unit 2C, Winnetka, IL 60093
• 

  

  /19

  $1,117,000

  Sold Mar 11, 2026

  380 Green Bay Rd Unit 1B, Winnetka, IL 60093

  • 2 Beds
  • 2 Baths
  • 1,950 Sq Ft
  • Built 1997

  Last Sold Summary

  • 16% Above List Price
  • $573/SF
  • 1 Day On Market

  Current Estimated Value $1,085,815

  Last Listing Agent Julie Miller Compass

  380 Green Bay Rd Unit 1B, Winnetka, IL 60093
• 

  

  /51

  Est $5,537,794

  Not Listed For Sale

  139 Sheridan Rd, Winnetka, IL 60093

  • 5 Beds
  • 8 Baths
  • 9,723 Sq Ft
  • Built 2021

  139 Sheridan Rd, Winnetka, IL 60093

  Last Sold Summary

  • 29 Days On Market

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

  

  /38

  $3,025,000

  Pending

  • 6 Beds
  • 6.5 Baths
  • 6,689 Sq Ft

  566 Willow Rd, Winnetka, IL 60093

  Perfectly positioned in coveted East Winnetka, this exquisite newer-construction stone residence offers timeless elegance, thoughtful design, and over 6,500 square feet of luxurious living across four beautifully finished levels. Upon entering the home, you can almost feel the lake breeze and catch a sight line of Lake Michigan-a reminder of this home's premier location just moments from the

  Carrie Tarzon @properties Christie's International Real Estate

  566 Willow Rd, Winnetka, IL 60093
• 

  

  /10

  $1,545 Per Month

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

  918 Green Bay Rd Unit 3B, 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 new home in the charming village of Winnetka, IL. This property offers a comfortable and inviting living space complemented by an ideal location close to dining and shopping options.This residence features spacious bedrooms

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

  

  /19

  $985,000

  Sold Nov 20, 2025

  785 Locust St, Winnetka, IL 60093

  • 3 Beds
  • 1.5 Baths
  • 1,224 Sq Ft
  • Built 1911

  Last Sold Summary

  • 12% Above List Price
  • $805/SF
  • 12 Days On Market

  Current Estimated Value $1,113,177

  Last Listing Agent Crawford Group @properties Christie's International Real Estate

  785 Locust St, Winnetka, IL 60093
• 

  

  /16

  Est $594,880

  Not Listed For Sale

  680 Green Bay Rd Unit 201, Winnetka, IL 60093

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1970

  680 Green Bay Rd Unit 201, Winnetka, IL 60093

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Tim Ratty Baird & Warner
• 

  /2

  $2,799,388

  New Construction Pending

  • 6 Beds
  • 5.5 Baths

  510 Provident Ave, Winnetka, IL 60093

  Situated on a quiet, highly desirable street in the heart of Winnetka, 510 Provident represents a thoughtful expression of modern North Shore architecture - where structural integrity, material quality, and enduring design converge. This new construction home offers six-bedrooms, six baths, over-scaled proportions and architectural clarity throughout. Ten-foot ceilings create an elevated sense of

  John Park John Park

  510 Provident Ave, Winnetka, IL 60093
• 

  

  /20

  $1,655 Per Month

  • 1 Bath
  • 450 Sq Ft
  • Apartment for Rent

  733 Elm St Unit 301, Winnetka, IL 60093

  Quality studio in the heart of downtown Winnetka features heat and water included, newer kitchen with dishwasher, separate dining room, spacious living area, great closet space, hardwood floors, newer bathroom, laundry room in building, and pets are welcome. Steps to Winnetka Metra stop, and a couple blocks to the Beach!

  Berthene Christos Urban Abodes Chicago

  733 Elm St Unit 301, Winnetka, IL 60093
• 

  

  /41

  $1,550,000

  Sold Apr 30, 2026

  1004 Elm St, Winnetka, IL 60093

  • 5 Beds
  • 3.5 Baths
  • 3,047 Sq Ft

  Last Sold Summary

  • 7% Above List Price
  • $509/SF
  • 9 Days On Market

  Current Estimated Value $1,539,315

  Last Listing Agent Stephanie Cutter Coldwell Banker Realty

  1004 Elm St, Winnetka, IL 60093
• 

  

  /53

  Est $2,738,764

  Not Listed For Sale

  201 Linden St, Winnetka, IL 60093

  • 6 Beds
  • 7 Baths
  • 5,761 Sq Ft
  • Built 1973

  201 Linden St, Winnetka, IL 60093

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Paige Dooley Compass
• 

  

  /38

  $3,495,000

  • 6 Beds
  • 7.5 Baths
  • 8,303 Sq Ft

  1015 Sheridan Rd, Winnetka, IL 60093

  Nestled on a private lane east of Sheridan Road, this distinguished Winnetka residence offers privacy, scale, quality craftsmanship, and exceptional everyday livability in one of the North Shore's most coveted east-side locations. Designed for elegant entertaining, multigenerational living, work-from-home flexibility, and relaxed daily comfort, the home features 6+ bedrooms, including a private

  Linda Martin Coldwell Banker Realty

  1015 Sheridan Rd, Winnetka, IL 60093
• 

  

  /7

  $1,795 Per Month

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

  733 Elm St Unit 304, 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 new home in the charming district of Winnetka, IL! This vibrant community is surrounded by great restaurants and department stores, offering convenience at your doorstep. The property is also in close proximity to notable educational

  733 Elm St Unit 304, Winnetka, IL 60093
• 

  /2

  $31,250,000

  Sold Aug 29, 2025

  419 Sheridan Rd, Winnetka, IL 60093

  • 7 Beds
  • 13 Baths
  • 13,894 Sq Ft
  • Built 1928

  Last Sold Summary

  • 11% Below List Price
  • $2,249/SF
  • 145 Days On Market

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

  419 Sheridan Rd, Winnetka, IL 60093
• 

  

  /23

  Est $960,008

  Not Listed For Sale

  660 Winnetka Mews Unit 214, Winnetka, IL 60093

  • 3 Beds
  • 3 Baths
  • 1,955 Sq Ft
  • Built 1973

  660 Winnetka Mews Unit 214, Winnetka, IL 60093

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Paige Dooley Compass
• 

  

  /31

  $1,399,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,992 Sq Ft

  1225 Elm St, Winnetka, IL 60093

  Privately tucked on an extra wide 1/3rd acre property, this fully re-imagined mid-century modern home offers exceptional design and incredible vistas of its lushly landscaped property. Thoughtfully curated with attention to detail and a sophisticated eye for design, the home blends timeless architecture with abundant natural beauty, right in the heart of Winnetka. A super chic, modern kitchen

  Paige Dooley Compass

  1225 Elm St, Winnetka, IL 60093
• 

  /2

  $1,670 Per Month

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

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

  Fantastic one bedroom, one bathroom in Winnetka features brand new kitchen with modern white cabinets, stainless steel appliances, dishwasher, separate dining area with ceiling fan, large living room with decorative fireplace, spacious bedroom, great closet space, hardwood floors, new bathroom, laundry in unit, and pets are welcome. Steps to Hubbard Woods Metra stop, and a block to Tower Road

  Berthene Christos Urban Abodes Chicago

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

  

  /43

  $1,515,000

  Sold Apr 30, 2026

  916 Oak St, Winnetka, IL 60093

  • 4 Beds
  • 2.5 Baths
  • 2,116 Sq Ft
  • Built 1911

  Last Sold Summary

  • 8% Above List Price
  • $716/SF
  • 4 Days On Market

  Current Estimated Value $1,531,459

  Last Listing Agent Joanne Hudson Compass

  916 Oak St, Winnetka, IL 60093
• 

  /2

  Est $1,845,975

  Not Listed For Sale

  1133 Scott Ave, Winnetka, IL 60093

  • 5 Beds
  • 4.5 Baths
  • 5,300 Sq Ft
  • Built 1923

  1133 Scott Ave, Winnetka, IL 60093

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Sherry Molitor Compass
• 

  

  /31

  $999,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,206 Sq Ft

  419 Provident Ave, Winnetka, IL 60093

  Winnetka "tree streets" gem! This fully updated home blends classic exterior charm with a modern, open layout! Featuring three bedrooms, two and a half baths, a gorgeous kitchen and a beautiful backyard. Huge living room anchored by pretty fireplace flows seamlessly into open newer white kitchen and dining area. Family room - located just off the kitchen - opens to a fully fenced backyard with

  Katharine Hackett @properties Christie's International Real Estate

  419 Provident Ave, Winnetka, IL 60093
• 

  

  /7

  $1,425 Per Month

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

  918 Green Bay Rd Unit 3J, 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 opportunity in the charming district of Winnetka, IL, where convenient living meets suburban tranquility. This lovely property is surrounded by several excellent restaurants and department stores, providing a vibrant

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

  

  /36

  $1,716,000

  Sold Aug 15, 2025

  567 Provident Ave, Winnetka, IL 60093

  • 5 Beds
  • 4.5 Baths
  • 3,747 Sq Ft
  • Built 2002

  Last Sold Summary

  • 11% Above List Price
  • $458/SF
  • 6 Days On Market

  Current Estimated Value $1,844,171

  Last Listing Agent Kathryn Moor Compass

  567 Provident Ave, Winnetka, IL 60093
• 

  

  /38

  Est $3,382,214

  Not Listed For Sale

  745 Sheridan Rd, Winnetka, IL 60093

  • 6 Beds
  • 7.5 Baths
  • 9,930 Sq Ft
  • Built 1990

  745 Sheridan Rd, Winnetka, IL 60093

  Last Sold Summary

  • 251 Days On Market

  Last Listing Agent Vaciliki Ress Berkshire Hathaway HomeServices Chicago
• 

  

  /8

  $2,595,000

  • Land
  • 1.45 Acres
  • $1,789,655 per Acre

  61 Woodley Rd, Winnetka, IL 60093

  Discover a once-in-a-lifetime opportunity to build your dream estate in one of the North Shore's most coveted neighborhoods. Situated on prestigious Woodley Road in Winnetka, this rarely available 1.45-acre property offers an extraordinary canvas for creating a truly exceptional residence. The existing home has already been demolished, leaving this premier homesite shovel-ready. Bring your own

  Stephen Todd Jameson Sotheby's Intl Realty

  61 Woodley Rd, Winnetka, IL 60093
• 

  

  /12

  $2,000 Per Month

  • 2 Beds
  • 1 Bath
  • 771 Sq Ft
  • Apartment for Rent

  909 Green Bay Rd Unit 3S, Winnetka, IL 60093

  This charming second-floor walk-up is ideally located in the heart of the Hubbard Woods Design District, near the train, restaurants, coffee shops, and boutique retail. The unit features classic vintage character, with double entry from the hall, two generously sized bedrooms, a large, inviting living area, and ample storage. Laundry is conveniently located one level down from the unit, on the

  Andra O'Neill @properties Christie's International Real Estate

  909 Green Bay Rd Unit 3S, Winnetka, IL 60093
• 

  

  /49

  $1,875,000

  Sold Apr 24, 2026

  1092 Ash St, Winnetka, IL 60093

  • 4 Beds
  • 3 Baths
  • 3,622 Sq Ft
  • Built 1926

  Last Sold Summary

  • 6% Above List Price
  • $518/SF

  Current Estimated Value $1,873,747

  Last Listing Agent Sally O'Donnell @properties Christie's International Real Estate

  1092 Ash St, Winnetka, IL 60093
• 

  

  /46

  Est $2,239,232

  Not Listed For Sale

  17 Longmeadow Rd, Winnetka, IL 60093

  • 7 Beds
  • 7 Baths
  • 6,000 Sq Ft
  • Built 1966

  17 Longmeadow Rd, Winnetka, IL 60093

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Daniel Mirea Berkshire Hathaway HomeServices Chicago
• 

  

  /16

  $285,000

  Pending

  • 2 Beds
  • 1 Bath

  1101 Merrill St Unit M1, Winnetka, IL 60093

  Rarely available 2 bed/1 bath condominium in the heart of Hubbard Woods, just steps from the Metra, shops, restaurants, cafes, and Lake Michigan. This beautifully refreshed home features new windows, freshly painted interiors, hardwood floors throughout, an updated bath, and a kitchen with granite countertops and newer stainless steel appliances. A separate dining room offers flexible space for

  Julie Cassin @properties Christie's International Real Estate

  1101 Merrill St Unit M1, Winnetka, IL 60093
• 

  

  /3

  $1,595 Per Month

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

  918 Green Bay Rd Unit 2C, 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 new home in the desirable district of Winnetka, IL. This charming property offers a perfect blend of comfort and convenience, ideal for those looking to enjoy a vibrant community life. The residence features spacious bedrooms

  918 Green Bay Rd Unit 2C, Winnetka, IL 60093
• 

  

  /33

  $1,305,000

  Sold May 15, 2026

  1505 Tower Rd, Winnetka, IL 60093

  • 4 Beds
  • 4 Baths
  • 3,225 Sq Ft
  • Built 1943

  Last Sold Summary

  • 31% Above List Price
  • $405/SF
  • 3 Days On Market

  Current Estimated Value $1,274,338

  Last Listing Agent Bonnie Tripton @properties Christie's International Real Estate

  1505 Tower Rd, Winnetka, IL 60093
• 

  

  /15

  Est $222,874

  Not Listed For Sale

  561 Hill Terrace Unit 310, Winnetka, IL 60093

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft
  • Built 1928

  561 Hill Terrace Unit 310, Winnetka, IL 60093

  Last Sold Summary

  • 67 Days On Market

  Last Listing Agent Michael Mitchell @properties Christie's International Real Estate

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