Winnetka, IL Homes

• 

  

  

  /35

  $2,899,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 5,102 Sq Ft

  792 Walden Rd, Winnetka, IL 60093

  Stunning million dollar+ renovation of a picture perfect brick center-entry Georgian colonial ideally positioned on one of Winnetka's most coveted streets with breathtaking views. Thoughtfully reimagined and meticulously renovated from top to bottom in 2022, this exceptional residence blending timeless architecture with beautifully curated finishes, impeccable craftsmanship, and modern luxury

  Paige Dooley Compass

  792 Walden Rd, Winnetka, IL 60093
• 

  

  /2

  $2,450,000

  Sold Jul 30, 2026

  406 Woodley Woods, Winnetka, IL 60093

  • 6 Beds
  • 6 Baths
  • 5,458 Sq Ft
  • Built 1988

  Last Sold Summary

  • 2% Below List Price
  • $449/SF
  • 16 Days On Market

  Current Estimated Value $2,485,946

  Last Listing Agent Jason Wagner Greystone Realty

  406 Woodley Woods, Winnetka, IL 60093
• 

  

  

  /36

  Est $1,864,960

  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

  • 3 Days On Market

  Last Listing Agent Leslie Maguire @properties Christie's International Real Estate
• 

  

  

  /31

  $1,195,000

  Pending

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

  1208 Oak St, Winnetka, IL 60093

  Nestled in the heart of Winnetka's coveted " TREE STREETS" neighborhood sits the storybook home you've been waiting for. This special home is a sun-filled Mediterranean villa with an effortless blend of timeless architecture and a fresh, coastal-inspired aesthetic throughout. The home showcases airy interiors, soft neutral tones, and a well appointed floor plan that perfectly suits today's

  Alyson Tesar @properties Christie's International Real Estate

  1208 Oak St, Winnetka, IL 60093
• 

  

  

  /28

  $875,000

  Sold Aug 25, 2025

  640 Winnetka Mews Unit 105, Winnetka, IL 60093

  • 2 Beds
  • 2 Baths
  • Built 1971

  Last Sold Summary

  • 3% Above List Price
  • 5 Days On Market

  Current Estimated Value $866,352

  Last Listing Agent Megan Mawicke Jameson Sotheby's International Realty

  640 Winnetka Mews Unit 105, Winnetka, IL 60093
• 

  

  /45

  Est $1,166,843

  Not Listed For Sale

  Unlisted Address

  • 3 Beds
  • 3.5 Baths
  • 2,600 Sq Ft
  • Built 1933

  Unlisted Address

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Katie Hauser Compass
• 

  

  /5

  $1,500,000

  • 4 Beds
  • 2.5 Baths
  • 2,895 Sq Ft

  1360 Sunview Ln, Winnetka, IL 60093

  Incredible opportunity to develop, customize, or thoughtfully renovate this traditional four-bedroom home situated on a picturesque half-acre lot backing directly to the Winnetka Golf Club on a quiet, tree-lined street. Whether you're envisioning a stunning custom new construction or transforming the existing residence into your dream home, this exceptional property offers endless possibilities

  Axel Cohen Compass

  1360 Sunview Ln, Winnetka, IL 60093
• 

  

  /29

  $4,200,000

  Sold Dec 17, 2025

  518 Elder Ln, Winnetka, IL 60093

  • 6 Beds
  • 7 Baths
  • 7,500 Sq Ft
  • Built 2025

  Last Sold Summary

  • 5% Below List Price
  • $560/SF
  • 15 Days On Market

  Current Estimated Value $4,029,177

  Last Listing Agent Matan Aharoni Engel & Voelkers Chicago North Shore

  518 Elder Ln, Winnetka, IL 60093
• 

  

  /37

  Est $1,543,154

  Not Listed For Sale

  807 Cherry St, Winnetka, IL 60093

  • 6 Beds
  • 4.5 Baths
  • 2,284 Sq Ft
  • Built 1921

  807 Cherry St, Winnetka, IL 60093

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Susan Maman @properties Christie's International Real Estate
• 

  

  /48

  $3,095,000

  • 5 Beds
  • 5 Baths
  • 4,212 Sq Ft

  Unlisted Address

  The quintessential white-painted Colonial always makes a timeless statement-but set on one of East Winnetka's most spectacular blocks, just steps from town, train, beach and Village Green, it becomes truly exceptional. Welcoming in all the most beautiful ways, this designer showcase house is the one you look forward to coming home to this summer. After hitting the beach, be home in 5 min to get

  Jena Radnay @properties Christie's International Real Estate

  Unlisted Address
• 

  

  /39

  $2,030,000

  Sold Nov 24, 2025

  386 Fairview Ave, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 5,284 Sq Ft
  • Built 1921

  Last Sold Summary

  • 12% Below List Price
  • $384/SF
  • 10 Days On Market

  Current Estimated Value $2,094,151

  Last Listing Agent Alexa Hara @properties Christie's International Real Estate

  386 Fairview Ave, Winnetka, IL 60093
• 

  

  /56

  Est $1,937,384

  Not Listed For Sale

  550 Sheridan Rd, Winnetka, IL 60093

  • 5 Beds
  • 4.5 Baths
  • 4,443 Sq Ft
  • Built 1942

  550 Sheridan Rd, Winnetka, IL 60093

  Last Sold Summary

  • 58 Days On Market

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

  

  /45

  $1,395,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 3,199 Sq Ft

  Unlisted Address

  Storybook Cape Cod in the Heart of Winnetka...Walk to Everything! Picture-perfect curb appeal, timeless character, and an unbeatable in-town location - this home has it all! Thoughtfully expanded and beautifully updated, this home offers the charm buyers love with the space and functionality for today's lifestyle. A welcoming center entrance opens to gracious living spaces designed for both

  Megan Mawicke Jameson Sotheby's International Realty

  Unlisted Address
• 

  

  /40

  $2,460,000

  Sold Nov 12, 2025

  228 Old Green Bay Rd, Winnetka, IL 60093

  • 5 Beds
  • 6 Baths
  • 7,788 Sq Ft
  • Built 1998

  Last Sold Summary

  • 7% Above List Price
  • $316/SF
  • 8 Days On Market

  Last Listing Agent Susan Maman @properties Christie's International Real Estate

  228 Old Green Bay Rd, Winnetka, IL 60093
• 

  

  /38

  Est $2,866,015

  Not Listed For Sale

  1024 Westmoor Rd, Winnetka, IL 60093

  • 5 Beds
  • 8 Baths
  • 5,619 Sq Ft
  • Built 2008

  1024 Westmoor Rd, Winnetka, IL 60093

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Rene Firmin @properties Christie's International Real Estate
• 

  

  /58

  $3,049,000

  Pending

  • 5 Beds
  • 4.5 Baths
  • 5,212 Sq Ft

  654 Pine St, Winnetka, IL 60093

  Inspired by timeless French Eclectic architecture and impeccably built in 2007, this extraordinary residence offers an exceptional blend of architectural character, refined craftsmanship, and modern luxury. Ideally located just blocks from Lake Michigan, top-rated schools, parks, town, and train, the home sits on a beautifully landscaped lot designed for both elegant entertaining and everyday

  Kelly Lundin Compass

  654 Pine St, Winnetka, IL 60093
• 

  

  /55

  $1,589,647

  Sold May 28, 2026

  Unlisted Address

  • 4 Beds
  • 4 Baths
  • 2,318 Sq Ft
  • Built 1921

  Last Sold Summary

  • 6% Above List Price
  • $686/SF
  • 4 Days On Market

  Current Estimated Value $1,600,541

  Last Listing Agent Emily Smart LeMire Compass

  Unlisted Address
• 

  

  /48

  Est $3,203,923

  Not Listed For Sale

  1016 Westmoor Rd, Winnetka, IL 60093

  • 5 Beds
  • 6.5 Baths
  • 4,600 Sq Ft
  • Built 2005

  1016 Westmoor Rd, Winnetka, IL 60093

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Jeannie Kurtzhalts Baird & Warner
• 

  

  /45

  $2,795,000

  • 5 Beds
  • 5.5 Baths
  • 4,089 Sq Ft

  73 Locust Rd, Winnetka, IL 60093

  A rare opportunity to own a home on one of the most sought after, serene country-like settings on the North Shore. The house is just steps from the Indian Hill Golf Club and part of the coveted Indian Hill neighborhood. Be close to other magnificent homes and wooded and mature landscaping. Only one owner since home was completed on this property in 2012. Stately and traditional two story brick

  Beverly Smith @properties Christie's International Real Estate

  73 Locust Rd, Winnetka, IL 60093
• 

  

  /25

  $55,500

  Sold Mar 10, 2026

  1300 W Branch Rd, Winnetka, IL 60093

  • 3 Beds
  • 2 Baths
  • Built 1988

  Last Sold Summary

  • 15% Below List Price
  • 54 Days On Market

  Last Listing Agent Virgilio Arreguin-Solorio My Casa Realty Corp.

  1300 W Branch Rd, Winnetka, IL 60093
• 

  

  /50

  Est $1,964,669

  Not Listed For Sale

  1509 Asbury Ave, Winnetka, IL 60093

  • 4 Beds
  • 4.5 Baths
  • 3,123 Sq Ft
  • Built 2003

  1509 Asbury Ave, Winnetka, IL 60093

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Nathan Freeborn Redfin Corporation
• 

  

  /81

  $29,900,000

  • 8 Beds
  • 13 Baths
  • 20,000 Sq Ft

  319 Sheridan Rd, Winnetka, IL 60093

  It's time to unveil the pinnacle of lakefront living in IL, as this newer construction estate is better than brand new construction as it encompasses features that could never be built today with the new lakefront building ordinances. Try to top this...your personal wellness club that is only 20 steps out to your own private, 141-foot wide, sandy beach with indoor pool, sauna, and

  Jena Radnay @properties Christie's International Real Estate

  319 Sheridan Rd, Winnetka, IL 60093
• 

  

  /39

  $1,885,000

  Sold Mar 27, 2026

  1370 Sunview Ln, Winnetka, IL 60093

  • 4 Beds
  • 5 Baths
  • 4,632 Sq Ft
  • Built 1988

  Last Sold Summary

  • 6% Below List Price
  • $407/SF
  • 18 Days On Market

  Current Estimated Value $1,969,107

  Last Listing Agent Janet Borden Compass

  1370 Sunview Ln, Winnetka, IL 60093
• 

  

  /42

  Est $1,643,102

  Not Listed For Sale

  1041 Elm St, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 2,354 Sq Ft
  • Built 1923

  1041 Elm St, Winnetka, IL 60093

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Leslie Maguire @properties Christie's International Real Estate
• 

  

  /48

  $1,495,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 3,362 Sq Ft

  1110 Elm St, Winnetka, IL 60093

  Timeless Elegance Meets Modern Luxury with this prime Winnetka home on a large corner lot. Discover the perfect blend of historic character and contemporary living in this meticulously maintained residence. From the moment you step inside, rich vintage craftsmanship takes center stage, highlighted by striking coffered ceilings, multiple cozy fireplaces, and an exquisite built-in buffet. At the

  Brian Grienenberger Baird & Warner

  1110 Elm St, Winnetka, IL 60093
• 

  

  /16

  $987,000

  Sold Feb 24, 2026

  436 Maple St, Winnetka, IL 60093

  • 4 Beds
  • 1.5 Baths
  • 3,100 Sq Ft
  • Built 1923

  Last Sold Summary

  • 13% Above List Price
  • $318/SF
  • 5 Days On Market

  Current Estimated Value $1,059,881

  Last Listing Agent Mark Jak @properties Christie's International Real Estate

  436 Maple St, Winnetka, IL 60093
• 

  

  /51

  Est $2,661,144

  Not Listed For Sale

  390 Hawthorn Ln, Winnetka, IL 60093

  • 4 Beds
  • 5.5 Baths
  • 5,300 Sq Ft
  • Built 2006

  390 Hawthorn Ln, Winnetka, IL 60093

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Paige Dooley Compass
• 

  

  /56

  $4,950,000

  • 5 Beds
  • 7 Baths
  • 9,908 Sq Ft

  32 Woodley Rd, Winnetka, IL 60093

  Nestled down a winding, private road on 1.9 meticulous park-like acres, this grand, almost 10,000 square foot residence exudes luxury and timeless elegance. The front entrance is set apart from the road by a sweeping circular drive bordered by private hedges and mature trees. Upon entering the stately, two-story foyer with a 25' ceiling, bridal staircase, black and white marble floor, formal

  Katharine Hackett @properties Christie's International Real Estate

  32 Woodley Rd, Winnetka, IL 60093
• 

  

  /41

  $3,525,000

  Sold Jun 15, 2026

  Unlisted Address

  • 4 Beds
  • 4.5 Baths
  • 5,499 Sq Ft
  • Built 1984

  Last Sold Summary

  • 2% Below List Price
  • $641/SF
  • 26 Days On Market

  Current Estimated Value $3,547,169

  Last Listing Agent Jody Dickstein @properties Christie's International Real Estate

  Unlisted Address
• 

  

  /20

  Est $605,262

  Not Listed For Sale

  711 Oak St Unit 401, Winnetka, IL 60093

  • 2 Beds
  • 2 Baths
  • 1,544 Sq Ft
  • Built 1983

  711 Oak St Unit 401, Winnetka, IL 60093

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Jason Zonis Crown Heights Realty
• 

  

  /48

  $2,699,000

  Pending

  • 5 Beds
  • 5.5 Baths
  • 5,000 Sq Ft

  1050 Spruce St, Winnetka, IL 60093

  Winnetka! This checks all of the boxes! 5 Beds/5.1 Baths. This gorgeous SFH comes with all of the perks. Gourmet kitchen with Sub-Zero/Thermador, large island, walk-in pantry and gorgeous breakfast area that opens to the family room. The first floor office has built-ins and French doors. Step into the formal dining room with beautiful ceiling details and moldings. Relax in the formal living room

  Bradley Dumes Baird & Warner

  1050 Spruce St, Winnetka, IL 60093
• 

  

  /20

  $300,000

  Sold Jun 05, 2026

  555 Hill Terrace Unit 307, Winnetka, IL 60093

  • 1 Bed
  • 1 Bath
  • 760 Sq Ft
  • Built 1926

  Last Sold Summary

  • $395/SF
  • 10 Days On Market

  Current Estimated Value $296,065

  Last Listing Agent Celia Nelson @properties Christie's International Real Estate

  555 Hill Terrace Unit 307, Winnetka, IL 60093
• 

  

  /54

  Est $1,620,044

  Not Listed For Sale

  1168 Hamptondale Ave, Winnetka, IL 60093

  • 4 Beds
  • 4.5 Baths
  • 2,949 Sq Ft
  • Built 1916

  1168 Hamptondale Ave, Winnetka, IL 60093

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Stephanie Melgard @properties Christie's International Real Estate
• 

  

  /8

  $1,299,000

  Pending

  • Land
  • 21,344 Sq Ft
  • $2,651,020 per Acre

  1295 Sunview Ln, Winnetka, IL 60093

  Beautiful 21,755 sq. ft lot on quiet cul-de-sac. Lot size 95 x 229. The permitted gross floor area for new construction or rehab is 6,805 sq. ft.

  Margaret Goss @properties Christie's International Real Estate

  1295 Sunview Ln, Winnetka, IL 60093
• 

  

  /60

  $3,000,000

  Sold Apr 17, 2026

  985 Pine Tree Ln, Winnetka, IL 60093

  • 6 Beds
  • 5.5 Baths
  • 7,200 Sq Ft
  • Built 2003

  Last Sold Summary

  • 4% Above List Price
  • $417/SF
  • 5 Days On Market

  Current Estimated Value $3,000,706

  Last Listing Agent Howard Meyers Compass

  985 Pine Tree Ln, Winnetka, IL 60093
• 

  

  /24

  Est $1,521,298

  Not Listed For Sale

  1173 Cherry St, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 2,860 Sq Ft
  • Built 1934

  1173 Cherry St, Winnetka, IL 60093

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Vanessa Carlson Illinois Discount Realty
• 

  

  /63

  $2,250,000

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

  42 Woodley Rd, Winnetka, IL 60093

  Rarely available first floor primary! 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. Owner extremely

  Peggy Lewis @properties Christie's International Real Estate

  42 Woodley Rd, Winnetka, IL 60093
• 

  /2

  $2,009,100

  Sold May 15, 2026

  91 Abbottsford Rd, Winnetka, IL 60093

  • 5 Beds
  • 4.5 Baths
  • 5,231 Sq Ft
  • Built 1926

  Last Sold Summary

  • 6% Above List Price
  • $384/SF
  • 3 Days On Market

  Current Estimated Value $1,957,607

  Last Listing Agent Laura Fitzpatrick @properties Christie's International Real Estate

  91 Abbottsford Rd, Winnetka, IL 60093
• 

  

  /64

  Est $2,586,878

  Not Listed For Sale

  384 Hawthorn Ln, Winnetka, IL 60093

  • 4 Beds
  • 7 Baths
  • 3,434 Sq Ft
  • Built 2007

  384 Hawthorn Ln, Winnetka, IL 60093

  Last Sold Summary

  Last Listing Agent Kelly Dunn Rynes Berkshire Hathaway HomeServices Chicago
• 

  

  /24

  $975,000

  Pending Pre-Foreclosure

  • 4 Beds
  • 3.5 Baths
  • 2,427 Sq Ft

  882 Willow Rd, Winnetka, IL 60093

  Prepare to be captivated by this picture-perfect 4-bedroom, 3.1-bathroom colonial-cottage home, meticulously updated with high-end designer finishes throughout. Boasting incredible curb appeal with its deep blue siding, crisp white trim, and brick-paver paths, this turn-key residence seamlessly blends historic architectural character with contemporary luxury. Inside, an airy, light-filled layout

  Karen Arenson Engel & Voelkers Chicago North Shore

  882 Willow Rd, Winnetka, IL 60093

Showing Results 121 - 160, Page 4 of 18