Winnetka, IL Homes

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  /53

  $5,149,000

  • 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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  /47

  $1,595 - $2,095 per month

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

  910 Green Bay Rd, Winnetka, IL 60093

  910 Green Bay Rd, Winnetka, IL 60093
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  /33

  $1,381,000 Sold Jun 25, 2025

  1413 Tower Rd, Winnetka, IL 60093

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

  Last Sold Summary

  • 15% Above List Price
  • $456/SF
  • 5 Days On Market

  Current Estimated Value $1,419,363

  Last Listing Agent Cricket King @properties Christie's International Real Estate

  1413 Tower Rd, Winnetka, IL 60093
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  /5

  Est $1,605,527 Not Listed For Sale

  1501 Tower Rd, Winnetka, IL 60093

  • 4 Beds
  • 4.5 Baths
  • 3,462 Sq Ft
  • Built 1949

  1501 Tower Rd, Winnetka, IL 60093

  Last Sold Summary

  • 11% Above List Price
  • $419/SF
  • 22 Days On Market

  Last Sold Price $1,450,000

  Last Listing Agent Carrie Tarzon @ Properties
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  /39

  $1,995,000 Pending

  • 4 Beds
  • 5 Baths
  • 4,632 Sq Ft

  1370 Sunview Ln, Winnetka, IL 60093

  Exquisitely crafted for luxurious living and effortless entertaining, this exceptional residence, custom designed by the homeowner and noted local architectural firm W.D. Murphy Associates, backs onto the serene golf course, offering picturesque views from every room and utmost privacy. Encompassing over 4,600 square feet of refined living space, this home lives like a ranch, with the vast

  Janet Borden Compass

  1370 Sunview Ln, Winnetka, IL 60093
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  /15

  $1,645 - $2,145 per month

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

  914 Green Bay Rd, Winnetka, IL 60093

  Modern Living in Winnetka — 918 Green BayDiscover your next home at 918 Green Bay, where classic charm meets contemporary comfort in the heart of Winnetka. Offering spacious studios starting at $1,645 and 1-bedroom apartments from $1,645, our community delivers exceptional value in a premier North Shore location.Choose from a variety of thoughtfully designed layouts — some feature

  914 Green Bay Rd, Winnetka, IL 60093
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  /22

  $261,000 Sold Oct 31, 2025

  1101 Merrill St Unit M1, Winnetka, IL 60093

  • 2 Beds
  • 1 Bath

  Last Sold Summary

  • 5% Below List Price
  • 30 Days On Market

  Current Estimated Value $264,935

  Last Listing Agent Hilde Wheeler Carter Coldwell Banker Realty

  1101 Merrill St Unit M1, Winnetka, IL 60093
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  /28

  Est $1,223,360 Not Listed For Sale

  1476 Scott Ave, Winnetka, IL 60093

  • 3 Beds
  • 2.5 Baths
  • 2,970 Sq Ft
  • Built 1967

  1476 Scott Ave, Winnetka, IL 60093

  Last Sold Summary

  • 24% Above List Price
  • $332/SF
  • 4 Days On Market

  Last Sold Price $985,000

  Last Listing Agent Joanne Hudson Compass
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  /41

  $3,599,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 5,499 Sq Ft

  Unlisted Address

  Beautifully designed ranch by renowned architect Tony Grunsfeld, perfectly situated on a private street and a spacious half-acre lot. This remarkable 4+bedroom, 4.1-bath home combines timeless architecture with thoughtful modern updates, offering comfortable, elegant living in one of the North Shore's most sought-after locations. The newly updated kitchen is the heart of the home, featuring all

  Jody Dickstein @properties Christie's International Real Estate

  Unlisted Address
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  /65

  $1,750 - $2,195 per month

  • 1 - 2 Beds
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  894 Green Bay Rd, Winnetka, IL 60093

  Listing presented by Marshall Lee, licensed leasing agent with Fulton Grace. Renovated 2 bedroom apartment in Winnetka! Features hardwood floors, spacious living area, updated kitchen & bath. Laundry available on-site. Pets

  894 Green Bay Rd, Winnetka, IL 60093
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  /38

  $1,675,000 Sold Mar 28, 2025

  429 Walnut St, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 3,200 Sq Ft
  • Built 1930

  Last Sold Summary

  • 18% Above List Price
  • $523/SF
  • 2 Days On Market

  Current Estimated Value $1,762,237

  Last Listing Agent Katie Hauser Compass

  429 Walnut St, Winnetka, IL 60093
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  /59

  Est $1,678,273 Not Listed For Sale

  1321 Scott Ave, Winnetka, IL 60093

  • 6 Beds
  • 5 Baths
  • 3,358 Sq Ft
  • Built 1928

  1321 Scott Ave, Winnetka, IL 60093

  Last Sold Summary

  • 30% Above List Price
  • $386/SF
  • 3 Days On Market

  Last Sold Price $1,295,000

  Last Listing Agent Joanne Hudson Compass
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  /27

  $1,225,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,777 Sq Ft

  706 Foxdale Ave, Winnetka, IL 60093

  Move in ready and walk to everything! 706 Foxdale has the layout and amenities you are looking for. Step into this welcoming home and enjoy the soaring ceilings in the 2 story family room. The first floor layout is perfect for family gatherings, offering a formal living and dining rooms, as well as the family room with a fireplace and abuilt-ins with a wet bar. The kitchen opens to the family

  Kate Huff @properties Christie's International Real Estate

  706 Foxdale Ave, Winnetka, IL 60093
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  /70

  $1,995 - $2,395 per month

  • 1 - 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Condo for Rent

  545 Chestnut St, Winnetka, IL 60093

  Listing presented by Marshall Lee, licensed leasing agent with Fulton Grace. Renovated 1 bedroom apartment in Winnetka! Unit features hardwood floors, updated kitchen & bath, separate dining area, laundry

  545 Chestnut St, Winnetka, IL 60093
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  /2

  $935,000 Sold Jul 30, 2025

  1442 Asbury Ave, Winnetka, IL 60093

  • 3 Beds
  • 2.5 Baths
  • 2,264 Sq Ft
  • Built 1925

  Last Sold Summary

  • $413/SF
  • 4 Days On Market

  Current Estimated Value $1,012,138

  Last Listing Agent Sherry Molitor Compass

  1442 Asbury Ave, Winnetka, IL 60093
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  /26

  Est $1,641,238 Not Listed For Sale

  850 Eldorado St, Winnetka, IL 60093

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft
  • Built 1945

  850 Eldorado St, Winnetka, IL 60093

  Last Sold Summary

  • 6% Above List Price
  • $692/SF
  • 3 Days On Market

  Last Sold Price $1,550,000

  Last Listing Agent Meg Sudekum @ Properties
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  /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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  /16

  $2,250 per month

  • 3 Beds
  • 1.5 Baths
  • 1,400 Sq Ft
  • Condo for Rent

  953 Westmoor Rd Unit 1, Winnetka, IL 60093

  Beautiful and bright 3 Bedroom unit with large private patio. Hardwood floors throughout and bedrooms upstairs. One and one half baths and in unit laundry. One garage spot included and easy street parking. Living room dining room opens to the stone patio. Updated kitchen with stainless steel appliances. Master bedroom and 2 large bedrooms - good closet space and storage in the attic with pull

  953 Westmoor Rd Unit 1, Winnetka, IL 60093
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  /2

  $750,000 Sold Jul 03, 2025

  736 Oak St Unit 736, Winnetka, IL 60093

  • 3 Beds
  • 2.5 Baths
  • 1,600 Sq Ft
  • Built 1965

  Last Sold Summary

  • 19% Above List Price
  • $469/SF
  • 1 Day On Market

  Current Estimated Value $723,346

  Last Listing Agent David Chung Compass

  736 Oak St Unit 736, Winnetka, IL 60093
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  /25

  Est $535,010 Not Listed For Sale

  778 Green Bay Rd, Winnetka, IL 60093

  • 3 Beds
  • 3 Baths
  • 1,559 Sq Ft
  • Built 1968

  778 Green Bay Rd, Winnetka, IL 60093

  Last Sold Summary

  • 28% Above List Price
  • $269/SF
  • 4 Days On Market

  Last Sold Price $419,250

  Last Listing Agent Joanne Hudson Compass
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  /47

  $1,700,000 Pending

  • 4 Beds
  • 4 Baths
  • 3,686 Sq Ft

  1351 Scott Ave, Winnetka, IL 60093

  Classic brick Dutch Colonial on a picturesque, tree-lined street in the heart of Hubbard Woods, offering an unbeatable walk-to-everything location just steps to the Metra, shops, parks, dining, and top-rated schools. Originally built in 1924 and extensively renovated with a substantial addition in 2015, this 4-bedroom, 2 full and 2 half bath home blends timeless architectural charm with

  Bonnie Tripton @properties Christie's International Real Estate

  1351 Scott Ave, Winnetka, IL 60093
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  /18

  $1,995 per month

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

  555 Chestnut St Unit J08W, Winnetka, IL 60093

  545 ChestnutChestnut + ElmWinnetka$1995 per MonthAvailable: NowAVAILABLE NOW! Fabulous one bedroom, one bathroom in heart of downtown Winnetka features reahbbed kitchen with espresso cabinets, stainless steel appliances, dishwasher, spacious living area, large bedroom, great closet space, rehabbed bathroom, hardwood floors throughout, laundry in unit, and pets are welcome!

  555 Chestnut St Unit J08W, Winnetka, IL 60093
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  /44

  $4,625,000 Sold Jun 16, 2025

  66 Fox Ln, Winnetka, IL 60093

  • 6 Beds
  • 8 Baths
  • 8,025 Sq Ft
  • Built 1926

  Last Sold Summary

  • 12% Below List Price
  • $576/SF
  • 84 Days On Market

  Current Estimated Value $4,656,870

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

  66 Fox Ln, Winnetka, IL 60093
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  /23

  Est $757,306 Not Listed For Sale

  800 Green Bay Rd, Winnetka, IL 60093

  • 3 Beds
  • 2 Baths
  • 1,612 Sq Ft
  • Built 1921

  800 Green Bay Rd, Winnetka, IL 60093

  Last Sold Summary

  • 40% Above List Price
  • $335/SF
  • 12 Days On Market

  Last Sold Price $540,000

  Last Listing Agent Michael Mitchell @ Properties
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  /33

  $1,800,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,560 Sq Ft

  312 Rosewood Ave, Winnetka, IL 60093

  This home delivers space, style, and everyday ease. The outdoor space is elegantly appointed with a large patio, pergola, and beautifully landscaped. Inside, this 4 bedroom, 3 and a half bath home offers a smart, flexible layout with generous room sizes, hardwood floors, and natural light throughout. The primary suite has been reimagined with custom closets and a new spa-inspired bath, plus a

  Nick Nastos Fulton Grace Realty

  312 Rosewood Ave, Winnetka, IL 60093
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  /20

  $2,195 per month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Condo for Rent

  890 Green Bay Rd Unit J07W, Winnetka, IL 60093

  894 Green BayGreen Bay + TowerWinnetka$2195 per MonthAvailable: NowAVAILABLE NOW! Peaceful two bedroom, one bathroom in beautiful Winnetka courtyard building features newer kitchen with stainless steel appliances, dishwasher, spacious living area, equal sized bedrooms, great closet space, new bathroom, hardwood floors throughout, laundry room in building, and pets are

  890 Green Bay Rd Unit J07W, Winnetka, IL 60093
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  /71

  $3,900,000 Sold May 14, 2025

  865 Gordon Terrace, Winnetka, IL 60093

  • 5 Beds
  • 6.5 Baths
  • 9,350 Sq Ft
  • Built 2017

  Last Sold Summary

  • 7% Below List Price
  • $417/SF
  • 45 Days On Market

  Current Estimated Value $4,305,023

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

  865 Gordon Terrace, Winnetka, IL 60093
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  /50

  Est $2,131,768 Not Listed For Sale

  1162 Scott Ave, Winnetka, IL 60093

  • 5 Beds
  • 6 Baths
  • 4,311 Sq Ft
  • Built 1920

  1162 Scott Ave, Winnetka, IL 60093

  Last Sold Summary

  • 11% Above List Price
  • $447/SF
  • 16 Days On Market

  Last Sold Price $1,925,000

  Last Listing Agent Bonnie Tripton @ Properties
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  /30

  $1,399,000 Open Sat 2:30PM - 4:30PM

  • 4 Beds
  • 2.5 Baths
  • 3,248 Sq Ft

  174 Woodland Ave, Winnetka, IL 60093

  This exceptional brick Dutch Colonial blends timeless charm with modern updates for effortless living. Sunlight fills generously-sized rooms, creating an inviting flow throughout this 4 bed/3.1 bath home. The formal living room, anchored by a striking wood-burning fireplace, opens seamlessly to a screened-in porch-perfect for entertaining or quiet relaxation. The spacious dining room accommodates

  Marlene Rubenstein Baird & Warner

  174 Woodland Ave, Winnetka, IL 60093
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  /32

  $1,895 - $1,995 per month

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

  545 Chestnut St, Winnetka, IL 60093

  Wonderful Vintage Landmark Building in WinnetkaIn the heart of downtown Winnetka, these units are surrounded by some incredible restaurants and shops including Peet’s Coffee and the Book Stall. This location is within walking distance of local schools and parks.Amenities:- Hardwood Floors- Separate Kitchen and Dining Area- Updated Bathroom- Miniblinds- Ceiling

  545 Chestnut St, Winnetka, IL 60093
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  /10

  $705,000 Sold May 01, 2025

  826 Humboldt Ave, Winnetka, IL 60093

  • 3 Beds
  • 1.5 Baths
  • 1,059 Sq Ft

  Last Sold Summary

  • 20% Below List Price
  • $666/SF
  • 873 Days On Market

  Current Estimated Value $883,724

  Last Listing Agent Paul Harb Wilmette Real Estate & Management Company LLC

  826 Humboldt Ave, Winnetka, IL 60093
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  /36

  Est $1,840,643 Not Listed For Sale

  385 Provident Ave, Winnetka, IL 60093

  • 4 Beds
  • 4.5 Baths
  • 3,178 Sq Ft
  • Built 1996

  385 Provident Ave, Winnetka, IL 60093

  Last Sold Summary

  • 14% Above List Price
  • $508/SF
  • 3 Days On Market

  Last Sold Price $1,615,000

  Last Listing Agent Leslie Maguire @ Properties
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  /42

  $1,050,000 Pending

  • 3 Beds
  • 4 Baths
  • 1,982 Sq Ft

  607 Orchard Ln, Winnetka, IL 60093

  So much to love about this East Winnetka charmer, from its curb appeal and large lot to the sun-filled rooms and multiple living spaces. The bluestone walkway, front steps and porch welcome you to this perfectly sized home. Main floor features include formal living room, large eat-in kitchen, separate dining area, powder room and step-down family room. The upstairs offers 3 bedrooms, including

  Julie Jensen Baird & Warner

  607 Orchard Ln, Winnetka, IL 60093
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  /47

  $1,595 - $2,095 per month

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

  910 Green Bay Rd, Winnetka, IL 60093

  910 Green Bay Rd, Winnetka, IL 60093
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  /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
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  /19

  Est $4,748,969 Not Listed For Sale

  41 Indian Hill Rd, Winnetka, IL 60093

  • 6 Beds
  • 8 Baths
  • 6,650 Sq Ft
  • Built 1924

  41 Indian Hill Rd, Winnetka, IL 60093

  Last Sold Summary

  • 4% Below List Price
  • $744/SF

  Last Sold Price $4,949,000

  Last Listing Agent Dinny Dwyer Compass
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  /37

  $1,299,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,316 Sq Ft

  1295 Sunview Ln, Winnetka, IL 60093

  Exciting chance to refashion this light-filled ranch home to your personal vision. Large windows throughout the home offer beautiful views and light. The spacious kitchen opens to the vaulted family room. The master bedroom and second bedroom are on the first floor, plus two full baths, family room, living room, dining room, and screened porch. Outdoors, there is an expansive stone patio and pond

  Margaret Goss @properties Christie's International Real Estate

  1295 Sunview Ln, Winnetka, IL 60093
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  /65

  $1,750 - $2,195 per month

  • 1 - 2 Beds
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  894 Green Bay Rd, Winnetka, IL 60093

  Listing presented by Marshall Lee, licensed leasing agent with Fulton Grace. Renovated 2 bedroom apartment in Winnetka! Features hardwood floors, spacious living area, updated kitchen & bath. Laundry available on-site. Pets

  894 Green Bay Rd, Winnetka, IL 60093
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  /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 $1,748,263

  Last Listing Agent Kathryn Moor Compass

  567 Provident Ave, Winnetka, IL 60093
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  /39

  Est $1,722,652 Not Listed For Sale

  1271 Asbury Ave, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 3,111 Sq Ft
  • Built 1920

  1271 Asbury Ave, Winnetka, IL 60093

  Last Sold Summary

  • 15% Above List Price
  • $483/SF
  • 3 Days On Market

  Last Sold Price $1,502,000

  Last Listing Agent Bonnie Tripton @ Properties

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