Winnetka, IL Homes

• 

  

  

  /45

  $1,400,000

  • 5 Beds
  • 4.5 Baths

  874 Boal Pkwy, Winnetka, IL 60093

  Set on approximately half an acre in sought-after Hubbard Woods, this five-bedroom + office, 4.1-bath home offers exceptional space, a versatile floor plan, and an outstanding North Shore location. The thoughtfully designed main level features a private office or living room, formal dining room, updated eat-in kitchen, and spacious family room overlooking the backyard, in-ground pool, oversized

  Christie Ascione @properties Christie's International Real Estate

  874 Boal Pkwy, Winnetka, IL 60093
• 

  

  /2

  $950,000

  Sold Jan 20, 2026

  Unlisted Address

  • 4 Beds
  • 3 Baths
  • 2,062 Sq Ft
  • Built 1928

  Last Sold Summary

  • $461/SF
  • 2 Days On Market

  Current Estimated Value $1,115,258

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

  Unlisted Address
• 

  

  

  /22

  Est $1,556,267

  Not Listed For Sale

  1028 Cherry St, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 2,711 Sq Ft
  • Built 1925

  1028 Cherry St, Winnetka, IL 60093

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Katie Traines @properties Christie's International Real Estate
• 

  

  

  /5

  $1,500,000

  Pending

  • 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
• 

  

  /2

  $910,000

  Sold Dec 17, 2025

  158 Woodland Ave, Winnetka, IL 60093

  • 3 Beds
  • 3 Baths
  • 2,200 Sq Ft
  • Built 1920

  Last Sold Summary

  • 2% Above List Price
  • $414/SF

  Current Estimated Value $1,042,697

  Last Listing Agent Catherine O'Connell @properties Christie's International Real Estate

  158 Woodland Ave, Winnetka, IL 60093
• 

  

  /32

  Est $1,849,436

  Not Listed For Sale

  804 Boal Pkwy, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 4,490 Sq Ft
  • Built 1955

  804 Boal Pkwy, Winnetka, IL 60093

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Selma Nemeth @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
• 

  /2

  $1,700,000

  Sold Sep 15, 2026

  854 Ash St, Winnetka, IL 60093

  • 4 Beds
  • 2.5 Baths
  • 3,653 Sq Ft
  • Built 1909

  Last Sold Summary

  • $465/SF
  • 1 Day On Market

  Current Estimated Value $1,701,490

  Last Listing Agent Ali Wenzke Compass

  854 Ash St, Winnetka, IL 60093
• 

  

  /31

  Est $3,061,215

  Not Listed For Sale

  824 Boal Pkwy, Winnetka, IL 60093

  • 5 Beds
  • 7 Baths
  • 6,300 Sq Ft
  • Built 2019

  824 Boal Pkwy, Winnetka, IL 60093

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Paul Gorney eXp Realty
• 

  

  /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
• 

  

  /46

  $2,200,000

  Sold Oct 15, 2025

  1503 Edgewood Ln, Winnetka, IL 60093

  • 4 Beds
  • 5 Baths
  • 3,319 Sq Ft
  • Built 1927

  Last Sold Summary

  • 23% Above List Price
  • $663/SF
  • 3 Days On Market

  Current Estimated Value $2,007,442

  Last Listing Agent Sarah Lyons @properties Christie's International Real Estate

  1503 Edgewood Ln, Winnetka, IL 60093
• 

  

  /5

  Est $1,534,813

  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

  • 22 Days On Market

  Last Listing Agent Carrie Tarzon @properties Christie's International Real Estate
• 

  

  /44

  $1,950,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,045 Sq Ft

  887 Ash St, Winnetka, IL 60093

  An inviting front porch welcomes you to this custom home designed by Reynolds Architecture. Fresh interiors with designer finishes and details create the feel of this curated residence, reflecting a modern sensibility and balance of casual and formal living. The foyer showcases herringbone hardwood floors leading to all first floor rooms. Custom cabinetry lines the hall adjacent to the elegant

  Howard Meyers Compass

  887 Ash St, Winnetka, IL 60093
• 

  

  /49

  $2,350,000

  Sold Jan 09, 2026

  180 Apple Tree Rd, Winnetka, IL 60093

  • 5 Beds
  • 3.5 Baths
  • 4,800 Sq Ft
  • Built 1955

  Last Sold Summary

  • 6% Below List Price
  • $490/SF
  • 45 Days On Market

  Current Estimated Value $2,425,342

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

  180 Apple Tree Rd, Winnetka, IL 60093
• 

  

  /28

  Est $1,376,535

  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

  • 4 Days On Market

  Last Listing Agent Joanne Hudson Compass
• 

  

  /43

  $2,675,000

  Open Sat 12PM - 2PM $120K PRICE DROP

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

  73 Locust Rd, Winnetka, IL 60093

  Basement renovation just done to add 6th bedroom that adjoins full bath! So much light enters basement through windows! 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

  Beverly Smith @properties Christie's International Real Estate

  73 Locust Rd, Winnetka, IL 60093
• 

  

  /39

  $1,305,000

  Sold Sep 15, 2026

  600 Sheridan Rd, Winnetka, IL 60093

  • 3 Beds
  • 2.5 Baths
  • 2,535 Sq Ft
  • Built 1949

  Last Sold Summary

  • 1% Above List Price
  • $515/SF
  • 5 Days On Market

  Current Estimated Value $1,661,286

  Last Listing Agent John Mawicke @properties Christie's International Real Estate

  600 Sheridan Rd, Winnetka, IL 60093
• 

  

  /10

  Est $1,062,850

  Not Listed For Sale

  826 Humboldt Ave, Winnetka, IL 60093

  • 3 Beds
  • 1.5 Baths
  • 1,059 Sq Ft
  • Built 1913

  826 Humboldt Ave, Winnetka, IL 60093

  Last Sold Summary

  • 873 Days On Market

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

  

  /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
• 

  

  /26

  $625,000

  Sold Jul 01, 2026

  680 Green Bay Rd Unit 306, Winnetka, IL 60093

  • 2 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1978

  Last Sold Summary

  • $372/SF
  • 2 Days On Market

  Current Estimated Value $620,070

  Last Listing Agent Connie Dornan @properties Christie's International Real Estate

  680 Green Bay Rd Unit 306, Winnetka, IL 60093
• 

  

  /26

  Est $1,668,730

  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

  • 3 Days On Market

  Last Listing Agent Meg Sudekum @properties Christie's International Real Estate
• 

  

  /51

  $2,749,900

  Pending

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

  438 Birch St, Winnetka, IL 60093

  Exceptional newer construction in an A+ Tree Streets location, this French Provincial-inspired brick and limestone home offers approximately 5,000 square feet of beautifully finished living space, an outstanding floor plan and an extraordinary level of care and maintenance. Built in 2012, this 5-bedroom, 4.1-bath home is ideally located just moments from schools, parks, the train, restaurants,

  Stacy Burgoon Compass

  438 Birch St, Winnetka, IL 60093
• 

  

  /33

  $1,925,000

  Sold Oct 23, 2025

  355 Myrtle St, Winnetka, IL 60093

  • 5 Beds
  • 4.5 Baths
  • 4,544 Sq Ft
  • Built 1930

  Last Sold Summary

  • 12% Below List Price
  • $424/SF
  • 45 Days On Market

  Current Estimated Value $2,097,175

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

  355 Myrtle St, Winnetka, IL 60093
• 

  

  /25

  Est $512,211

  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

  • 4 Days On Market

  Last Listing Agent Joanne Hudson Compass
• 

  

  /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
• 

  

  /48

  $2,825,000

  Sold Sep 11, 2026

  567 Oak St, Winnetka, IL 60093

  • 5 Beds
  • 5 Baths
  • 4,212 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Below List Price
  • $671/SF
  • 9 Days On Market

  Current Estimated Value $2,913,126

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

  567 Oak St, Winnetka, IL 60093
• 

  

  /63

  Est $10,553,855

  Not Listed For Sale

  765 Sheridan Rd, Winnetka, IL 60093

  • 7 Beds
  • 8 Baths
  • 15,784 Sq Ft
  • Built 2005

  765 Sheridan Rd, Winnetka, IL 60093

  Last Sold Summary

  • 8 Days On Market

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

  

  /46

  $2,499,000

  Pending

  • 4 Beds
  • 4.5 Baths
  • 3,610 Sq Ft

  1192 Chatfield Rd, Winnetka, IL 60093

  This is the opportunity buyers wait for. An architecturally significant Hubbard Woods Georgian that could never be duplicated today for anywhere near this cost. Perfectly positioned on one of the neighborhood's most coveted cul-de-sac streets, this distinctive home showcases extraordinary vintage details paired with over $1.2 million in thoughtful renovations and infrastructure improvements. Step

  Jena Radnay @properties Christie's International Real Estate

  1192 Chatfield Rd, Winnetka, IL 60093
• 

  

  /23

  $639,000

  Sold Mar 27, 2026

  640 Winnetka Mews Unit 405, Winnetka, IL 60093

  • 3 Beds
  • 3 Baths
  • 1,862 Sq Ft
  • Built 1971

  Last Sold Summary

  • $343/SF
  • 5 Days On Market

  Current Estimated Value $639,816

  Last Listing Agent Joanne Hudson Compass

  640 Winnetka Mews Unit 405, Winnetka, IL 60093
• 

  

  /46

  Est $2,740,334

  Not Listed For Sale

  953 Spruce St, Winnetka, IL 60093

  • 4 Beds
  • 5.5 Baths
  • 5,026 Sq Ft
  • Built 2009

  953 Spruce St, Winnetka, IL 60093

  Last Sold Summary

  • 10 Days On Market

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

  

  /53

  $4,949,000

  • 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
• 

  

  /10

  $500,000

  Sold May 01, 2026

  97 High St, Winnetka, IL 60093

  • 2 Beds
  • 3.5 Baths
  • 1,364 Sq Ft
  • Built 1949

  Last Sold Summary

  • 17% Below List Price
  • $367/SF
  • 16 Days On Market

  Current Estimated Value $519,386

  Last Listing Agent Lilia Balan Pavlova Properties

  97 High St, 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
• 

  

  /58

  $2,400,000

  Sold Aug 27, 2026

  920 Pine Tree Ln, Winnetka, IL 60093

  • 5 Beds
  • 5.5 Baths
  • 3,626 Sq Ft
  • Built 1963

  Last Sold Summary

  • 14% Above List Price
  • $662/SF
  • 4 Days On Market

  Current Estimated Value $2,110,777

  Last Listing Agent Joanne Hudson Compass

  920 Pine Tree Ln, Winnetka, IL 60093
• 

  

  /45

  Est $1,182,151

  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
• 

  

  /35

  $1,615,000

  Sold May 29, 2026

  841 Prospect Ave, Winnetka, IL 60093

  • 5 Beds
  • 3.5 Baths
  • 2,478 Sq Ft
  • Built 1899

  Last Sold Summary

  • 11% Above List Price
  • $652/SF
  • 5 Days On Market

  Current Estimated Value $1,629,314

  Last Listing Agent Christie Ascione @properties Christie's International Real Estate

  841 Prospect Ave, Winnetka, IL 60093
• 

  

  /37

  Est $1,629,266

  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
• 

  

  /45

  $2,345,000

  Sold Jul 15, 2026

  1258 Scott Ave, Winnetka, IL 60093

  • 5 Beds
  • 5.5 Baths
  • 3,426 Sq Ft
  • Built 1979

  Last Sold Summary

  • 7% Above List Price
  • $684/SF
  • 3 Days On Market

  Current Estimated Value $2,174,173

  Last Listing Agent Sara Sullivan Compass

  1258 Scott 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
• 

  /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 $2,507,151

  Last Listing Agent Jason Wagner Greystone Realty

  406 Woodley Woods, Winnetka, IL 60093

Showing Results 81 - 120, Page 3 of 18