Winnetka, IL Homes

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  /58

  $2,850,000 Pending

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

  205 Scott Ave, Winnetka, IL 60093

  Beautifully renovated lannon stone luxury residence steps from town, train and the lake. Enter through the grand center hall that leads to both the dining room with floor to ceiling windows and an inviting living room with wood burning fireplace and views of the lush yard. The renovated Chef's kitchen features custom cabinets, high-end appliances including a La Cornue range, double oven, beverage

  Nicole Hajdu Baird & Warner

  205 Scott Ave, Winnetka, IL 60093
• Explore Winnetka

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  /15

  $15,000 per month

  • 6 Beds
  • 5.5 Baths
  • House for Rent

  82 Woodley Rd, Winnetka, IL 60093

  Fantastic furnished short-term rental opportunity! Available August 12th, 2025 thru May 31st, 2026. This exquisite residence sits on just over 1.5 professionally, landscaped acres in sought after Indian Hill. The home boasts 6 bedrooms and 5.1 baths and has been tastefully renovated and lovingly maintained throughout the years. The incredible chef's kitchen features top of the line appliances

  

  Michael Mitchell

  @properties Christie's International Real Estate

  (224) 524-1299

  82 Woodley Rd, Winnetka, IL 60093
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  /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

  Last Listing Agent Dinny Dwyer Compass

  1288 Sunview Ln, Winnetka, IL 60093
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  /15

  Est $230,613 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft

  561 Hill Terrace Unit 310, Winnetka, IL 60093

  561 Hill Terrace Unit 310, Winnetka, IL 60093
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  /73

  $3,495,000

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

  42 Woodley Rd, Winnetka, IL 60093

  Rarely available 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.

  Peggy Lewis @properties Christie's International Real Estate

  42 Woodley Rd, Winnetka, IL 60093
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  /5

  $1,845 per month

  458 Winnetka Ave

  Studio - 2 Beds

  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

  458 Winnetka Ave, Winnetka, IL 60093
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  /61

  $9,575,000 Sold Jun 06, 2025

  381 Sheridan Rd, Winnetka, IL 60093

  • 5 Beds
  • 8 Baths
  • 8,086 Sq Ft
  • Built 2015

  Last Sold Summary

  • 7% Below List Price
  • $1,184/SF
  • 25 Days On Market

  Current Estimated Value $10,867,919

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

  381 Sheridan Rd, Winnetka, IL 60093
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  /22

  Est $1,033,280 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,756 Sq Ft

  1260 Ash St, Winnetka, IL 60093

  1260 Ash St, Winnetka, IL 60093
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  /48

  $2,295,000

  • 5 Beds
  • 4.5 Baths
  • 4,390 Sq Ft

  1159 Chatfield Rd, Winnetka, IL 60093

  Blending timeless elegance with modern sophistication, this stunning 2016 Winnetka home feels better than new. Designed for light, flow, and effortless living, it features 10-foot ceilings, white oak floors, and expansive windows that fill each room with warmth. The gourmet kitchen showcases custom cabinetry, large island, and professional appliances is perfect for everyday living and

  Jason Rowland Compass

  1159 Chatfield Rd, Winnetka, IL 60093
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  /26

  $3,000 per month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  Unlisted Address

  GREAT OPPORTUNITY IN WINNETKA! STEPS TO BOTH THE TRAIN AND DOWNTOWN, THIS SPRAWLING 2 BEDROOM UNIT FEELS LIKE HOME! SPACIOUS AND SUNNY UNIT WITH NEWLY REFINISHED HARDWOOD FLOORS FEATURES PLENTY OF CLOSET SPACE, LARGE BEDROOMS, AND AN OFFICE OFF OF THE LIVING ROOM! WALK UPSTAIRS FROM PRIVATE ENTRANCE AND YOU ENTER THE BRIGHT LIVING ROOM FOLLOWED BY A FORMAL DINING ROOM. KITCHEN IS UPDATED W/ SS

  Jim Streff Berkshire Hathaway HomeServices Chicago

  Unlisted Address
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  /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

  Last Listing Agent Grace Goro Compass

  917 Willow Rd, Winnetka, IL 60093
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  /19

  Est $729,724 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,995 Sq Ft

  711 Oak St Unit 303, Winnetka, IL 60093

  711 Oak St Unit 303, Winnetka, IL 60093
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  /52

  $4,560,000 Pending

  • 6 Beds
  • 7 Baths
  • 8,549 Sq Ft

  640 Hill Rd, Winnetka, IL 60093

  Greeley and Winnetka schools!! Welcome to Meadowpool - a distinguished Tudor residence nestled on a meticulously landscaped and wooded one acre lot. Built in 1923, the home's design exudes classic Tudor charm with stucco and stone exterior and a slate roof. The entryway is adorned with leaded glass windows and rich woodwork and leads to a charming living room featuring a limestone fireplace. The

  Deborah Richwine @properties Christie's International Real Estate

  640 Hill Rd, Winnetka, IL 60093
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  /13

  $1,995 per month

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  894 Green Bay Rd Unit 896B-17, Winnetka, IL 60093

  Renovated 2 bedroom apartment in Winnetka! Features hardwood floors, spacious living area, updated kitchen & bath. Laundry available on-site. Pets welcome. Close to Hubbard Woods Park, Metra, restaurants and more! Presented by Fulton Grace, Chicago IL. *Pictures may be of a similar unit in building.

  894 Green Bay Rd Unit 896B-17, 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 $1,508,514

  Last Listing Agent Patricia Skirving Compass

  605 Lincoln Ave, Winnetka, IL 60093
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  /29

  Est $2,150,764 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,400 Sq Ft

  1060 Spruce St, Winnetka, IL 60093

  1060 Spruce St, Winnetka, IL 60093
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  /75

  $3,999,900 Pending

  • 5 Beds
  • 7 Baths
  • 7,548 Sq Ft

  145 Woodley Rd, Winnetka, IL 60093

  If My Best Friend's Wedding had a sequel...it would be filmed right here. This coastal Colonial estate set on 1.4 acres of lush, manicured grounds on premier Woodley Road offers the ultimate backdrop for timeless North Shore living. Elegant, welcoming, and effortlessly cinematic, it's the kind of home where every day feels like a scene straight out of a movie. A rare generational opportunity,

  Jena Radnay @properties Christie's International Real Estate

  145 Woodley Rd, Winnetka, IL 60093
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  /17

  $3,000 per month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  1097 Tower Rd Unit A, Winnetka, IL 60093

  GREAT OPPORTUNITY IN WINNETKA! STEPS TO BOTH THE TRAIN AND DOWNTOWN, THIS SPRAWLING 2 BEDROOM UNIT FEELS LIKE HOME! SPACIOUS AND SUNNY UNIT HAS BEEN FRESHLY PAINTED WITH NEWLY REFINISHED HARDWOOD FLOORS FEATURES PLENTY OF CLOSET SPACE, LARGE BEDROOMS, AND MORE! WALK INTO YOUR UNIT FROM A PRIVATE ENTRANCE AND YOU ENTER THE BRIGHT LIVING ROOM FOLLOWED BY A FORMAL DINING ROOM. KITCHEN IS UPDATED W/

  Jim Streff Berkshire Hathaway HomeServices Chicago

  1097 Tower Rd Unit A, Winnetka, IL 60093
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  /18

  $1,500,000 Sold May 01, 2025

  965 Spruce St, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft
  • Built 1886

  Last Sold Summary

  • 3% Above List Price
  • $500/SF
  • 18 Days On Market

  Current Estimated Value $1,626,489

  Last Listing Agent Glenn Pankau Compass

  965 Spruce St, Winnetka, IL 60093
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  /20

  Est $955,107 Not Listed For Sale

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

  812 Oak St Unit 201, Winnetka, IL 60093

  812 Oak St Unit 201, Winnetka, IL 60093
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  /44

  $2,500,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 5,184 Sq Ft

  355 Linden St, Winnetka, IL 60093

  Meticulously renovated, this exceptional Winnetka home blends timeless charm with modern luxury. The five-bedroom, four-and-a-half-bath home features thoughtfully curated details throughout. Ideally situated near the lake, train, schools, parks, and downtown. The interiors have been fully reimagined with high-end finishes throughout, including custom white oak herringbone flooring on the main

  Iris Kohl Compass

  355 Linden St, Winnetka, IL 60093
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  /7

  $1,995 per month

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  896 Green Bay Rd Unit 7, Winnetka, IL 60093

  Winnetka ~ Two Bedroom Small Pets WelcomeThis apartment has everything you need for stylish, convenient living in one of the North Shore s most desirable neighborhoods. Whether youre commuting to the city or enjoying the local charm of Winnetka, you ll love coming home to this beautifully updated space.Live in the heart of charming Downtown Winnetka in this beautifully updated one

  896 Green Bay Rd Unit 7, Winnetka, IL 60093
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  /21

  $575,000 Sold Mar 31, 2025

  606 Lincoln Ave Unit 606, Winnetka, IL 60093

  • 2 Beds
  • 1.5 Baths
  • 1,500 Sq Ft
  • Built 1956

  Last Sold Summary

  • 10% Above List Price
  • $383/SF
  • 0 Days On Market

  Current Estimated Value $588,982

  Last Listing Agent Sara Sullivan Compass

  606 Lincoln Ave Unit 606, Winnetka, IL 60093
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  /22

  Est $655,822 Not Listed For Sale

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

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

  720 Green Bay Rd Unit 3B, Winnetka, IL 60093
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  /53

  $2,799,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 3,748 Sq Ft

  334 Woodland Ave, Winnetka, IL 60093

  Absolutely breathtaking "better-than-new" East Winnetka Classic on an oversized (75' wide) property in a desirable walk-to-all location beautifully balances elegance and ease. Exquisitely renovated with timeless details and high-end designer finishes, it offers a harmonious blend of refined design and modern comfort on 1/3-acre of beautifully landscaped grounds with an attached two-car garage.

  Paige Dooley Compass

  334 Woodland Ave, Winnetka, IL 60093
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  /29

  $9,500 per month

  • 4 Beds
  • 3.5 Baths
  • 3,076 Sq Ft
  • House for Rent

  526 Orchard Ln, Winnetka, IL 60093

  Discover an incredible rental opportunity in the highly sought-after East Winnetka! This beautiful home features 4 bedrooms, 3.5 bathrooms, and generous living spaces on a wide 65-foot lot. The interior showcases hardwood floors, a cozy fireplace, and a modern updated kitchen with stainless steel appliances and stunning Calcutta white marble countertops. The kitchen seamlessly connects to a

  Marlene Rubenstein Baird & Warner

  526 Orchard Ln, Winnetka, IL 60093
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  /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 $1,139,726

  Last Listing Agent Carly Jones Engel & Voelkers Chicago North Shore

  886 Willow Rd, Winnetka, IL 60093
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  /41

  Est $775,638 Not Listed For Sale

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

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

  720 Green Bay Rd Unit 2D, Winnetka, IL 60093
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  /21

  $7,275,000

  • 6 Beds
  • 7.5 Baths
  • 15,000 Sq Ft

  43 Indian Hill Rd, Winnetka, IL 60093

  New magnificent transitional home situated on 1 acre picturesque lot with approximately 15,000 square feet finished space. Exterior is constructed of stone and limestone with slate roof which represents timeless construction. The house features 6 bedrooms, 7.1 bath, 4 fireplaces, spectacular Neff kitchen with top-of-the-line appliances including Sub-Zero refrigerators/freezers, luxury Wolf range,

  Milena Birov @properties Christie's International Real Estate

  43 Indian Hill Rd, Winnetka, IL 60093
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  /13

  $2,195 per month

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  894 Green Bay Rd Unit 894B-05, Winnetka, IL 60093

  Renovated 2 bedroom apartment in Winnetka! Features hardwood floors, spacious living area, updated kitchen & bath. Laundry available on-site. Pets welcome. Close to Hubbard Woods Park, Metra, restaurants and more! Presented by Fulton Grace, Chicago IL. *Pictures may be of a similar unit in building.

  894 Green Bay Rd Unit 894B-05, Winnetka, IL 60093
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  /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 $1,945,485

  Last Listing Agent Paige Dooley Compass

  475 Maple St, Winnetka, IL 60093
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  /2

  Est $3,716,500 Not Listed For Sale

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

  104 Longmeadow Rd, Winnetka, IL 60093

  104 Longmeadow Rd, Winnetka, IL 60093
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  /2

  $1,600,000

  • 4 Beds
  • 5 Baths
  • 4,681 Sq Ft

  33 Longmeadow Rd, Winnetka, IL 60093

  The house is being sold as-is. Property is being sold as a two-lot subdivision. Property is in the process of being surveyed and owner is working with Northfield to subdivide the lot. Beautify private setting with mature trees along the perimeter.

  Joseph Nash @properties Christie's International Real Estate

  33 Longmeadow Rd, Winnetka, IL 60093
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  /14

  $2,000 per month

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

  913 Green Bay Rd Unit 2N, Winnetka, IL 60093

  This second floor walk up is in the heart of Hubbard Woods Design District near train, restaurants, coffee shops, and retail stores. The unit showcases vintage charm and character, offering two bedrooms and a separate dining room with glass French doors, a four-season room, and one full bathroom. The beautiful kitchen has good counter and cabinet space, highlighted by quartz countertops and

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

  913 Green Bay Rd Unit 2N, Winnetka, IL 60093
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  /2

  $2,600,000 Sold Apr 09, 2025

  1172 Hamptondale Ave, Winnetka, IL 60093

  • 5 Beds
  • 6 Baths
  • 4,870 Sq Ft
  • Built 1920

  Last Sold Summary

  • 8% Above List Price
  • $534/SF
  • 4 Days On Market

  Current Estimated Value $2,716,961

  Last Listing Agent Howard Meyers Compass

  1172 Hamptondale Ave, Winnetka, IL 60093
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  /5

  Est $2,843,635 Not Listed For Sale

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

  269 Woodlawn Ave, Winnetka, IL 60093

  269 Woodlawn Ave, Winnetka, IL 60093
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  /59

  $1,995,000

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

  1215 Spruce St, Winnetka, IL 60093

  A RARE find...Amazing home with an expansive *first floor Primary suite, set on a spectacular half-acre in a prime Winnetka location! This deceptively spacious home offers exceptional indoor-outdoor living and a versatile floor plan. The professionally landscaped backyard is a true showstopper, featuring mature trees, perennial gardens and a spacious bluestone patio...perfect for large-scale

  Megan Mawicke Jameson Sotheby's International Realty

  1215 Spruce St, Winnetka, IL 60093
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  /2

  $1,625 per month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  916 Green Bay Rd Unit 918-G, 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-G, Winnetka, IL 60093
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  /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 $2,426,113

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

  107 Woodley Rd, Winnetka, IL 60093
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  /30

  Est $2,019,653 Not Listed For Sale

  • 4 Beds
  • 5.5 Baths
  • 3,656 Sq Ft

  285 Woodlawn Ave, Winnetka, IL 60093

  285 Woodlawn Ave, Winnetka, IL 60093

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