Winnetka Homes

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  /33

  $2,199,000 Pending

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

  355 Myrtle St, Winnetka, IL 60093

  Timeless Elegance in the Heart of East Winnetka! Set on an expansive, professionally landscaped lot, this East Winnetka residence exudes timeless elegance and exceptional curb appeal. A grand foyer welcomes you into a home where classic architecture meets modern comfort. The richly paneled family room offers a sophisticated retreat, while the formal living room, bathed in natural light, features

  

  Mary Grant

  @properties Christie's International Real Estate

  (224) 571-9499

  355 Myrtle St, Winnetka, IL 60093
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  /14

  $1,995 per month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  545 Chestnut St Unit 545-303, Winnetka, IL 60093

  Renovated 1 bedroom apartment in Winnetka! Unit features hardwood floors, updated kitchen & bath, separate dining area, laundry in-unit. Pet friendly building. Great location close to Dwyer Park, Metra, restaurants and shopping! Presented by Fulton Grace, Chicago IL.*Pictures may be of a similar unit in building.

  545 Chestnut St Unit 545-303, Winnetka, IL 60093
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  /29

  $2,200,000 Sold Sep 30, 2025

  • 3,659 Sq Ft
  • $601/SF
  • 4 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1943

  545 Sheridan Rd, Winnetka, IL 60093

  Welcome to this handsome Georgian located on highly sought-after Sheridan Road in Winnetka, IL, where timeless architecture meets modern living. This stately red brick residence offers an exceptional lifestyle just one half block from Lake Michigan, blending historic charm with contemporary comfort. The grand foyer sets the tone with classic detailing and gleaming hardwood floors that flow

  Julie Miller Compass

  545 Sheridan Rd, Winnetka, IL 60093
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  /34

  Est $2,449,685 Not Listed For Sale

  • 4 Beds
  • 5.5 Baths
  • 3,947 Sq Ft

  1189 Asbury Ave, Winnetka, IL 60093

  1189 Asbury Ave, Winnetka, IL 60093
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  /40

  $2,399,000 Open Sat 10:30AM - 12:30PM

  • 6 Beds
  • 5.5 Baths
  • 4,546 Sq Ft

  1183 Tower Rd, Winnetka, IL 60093

  Perfectly blending timeless character with thoughtful updates, this beautifully renovated and expanded home shines inside and out. Every detail has been selected for quality and style, creating a space that feels both elegant and effortlessly livable. Set on a fully fenced, landscaped, and hardscaped 1/3+ acre lot, the home welcomes you with its classic Nantucket shingle style. Inside, the

  Megan Leadbetter Coldwell Banker Realty

  1183 Tower Rd, Winnetka, IL 60093
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  /20

  $7,800 per month

  • 5 Beds
  • 3 Baths
  • House for Rent

  510 Ash St, Winnetka, IL 60093

  You will love this charming Winnetka home in prime east location on a coveted street two blocks from Lake Michigan. Easy walk to Greeley School, New Trier High School, Metra train, bike trails, beaches and town. Special features include large sunlit rooms, beautiful hardwood floors, a large eat-in kitchen with all stainless steel appliances and granite counters, a first floor office/ bedroom with

  Beth Groebe Coldwell Banker Realty

  510 Ash St, Winnetka, IL 60093
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  /61

  $2,600,000 Sold Sep 18, 2025

  • 4,698 Sq Ft
  • $553/SF
  • 5 Days On Market

  • 6 Beds
  • 5 Baths
  • Built 2000

  321 Woodland Ave, Winnetka, IL 60093

  On the market for the first time ever, this 6 bedroom, 5 bath, 4698 SQFT Winnetka home is not to be missed! Custom-built 25 years ago by Dennis McKenna, this charming brick home is set on beautifully landscaped grounds with mature trees and a bluestone inlaid path that divides the front yard, leading right to the front door. The entry foyer welcomes you home and separates the space evenly between

  Carrie McCormick @properties Christie's International Real Estate

  321 Woodland Ave, Winnetka, IL 60093
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  /29

  Est $2,263,941 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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  /38

  $2,695,000

  • 4 Beds
  • 5 Baths
  • 4,574 Sq Ft

  92 Indian Hill Rd, Winnetka, IL 60093

  This incredible & expansive 4 bedroom, 3.2 bathroom home is situated on .654 acres of spectacular property in an idyllic & private location. Surrounded by mature trees and beautiful foliage, the fantastic gardens & outdoor area boast three bluestone patios. The home brings the outdoors inside with oversized windows throughout the home. When you walk into the home, you are welcomed in the large

  Kathryn Mangel @properties Christie's International Real Estate

  92 Indian Hill Rd, Winnetka, IL 60093
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  /20

  $2,195 per month

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

  811 Elm St Unit A07C, Winnetka, IL 60093

  811 ElmElm + ChestnutWinnetka$2195 per MonthAvailable: NowAVAILABLE NOW! Handsome one bedroom, one bathroom in heart of downtown Winnetka features rehabbed kitchen, spacious living area, equal sized bedrooms, great closet space, rehabbed bathroom, hardwood floors throughout, laundry in unit, and pets welcome! Steps to Winnetka Metra stop, shops, restaurants, Public

  811 Elm St Unit A07C, Winnetka, IL 60093
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  $1,785,000 Sold Sep 15, 2025

  • 2,826 Sq Ft
  • $632/SF
  • 4 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1925

  1473 Edgewood Ln, Winnetka, IL 60093

  What a stunning transformation! Tucked away on a quiet, tree-lined street in coveted Hubbard Woods, this classic brick home has been completely transformed through an extensive renovation, seamlessly blending timeless elegance with modern luxury. With 4 bedrooms & 4.5 bathrooms, this residence offers exceptional craftsmanship & design at every turn. Wide-plank white oak floors lead you through

  Alicja Skibicki Baird & Warner

  1473 Edgewood Ln, Winnetka, IL 60093
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  /20

  Est $913,138 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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  /49

  $2,649,000 Open Sun 10AM - 12PM

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

  180 Apple Tree Rd, Winnetka, IL 60093

  Storybook Cape Cod set on enchanting Apple Tree Road complete with that magical sidewalk to Crow Island School, this red brick colonial accented with classic black shutters and white trim offers timeless comfort in a very special nook! Nestled on a lush half-acre lot with mature trees, a circular drive & attached 2-car garage accented by plantation shutter windows, this home radiates charm with

  Jena Radnay @properties Christie's International Real Estate

  180 Apple Tree Rd, Winnetka, IL 60093
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  $11,500 per month

  • 5 Beds
  • 5.5 Baths
  • 6,500 Sq Ft
  • House for Rent

  1010 Hubbard Place, Winnetka, IL 60093

  Available now for a 5-month lease with a possible option to extend month-to-month, this traditional cedar shake-style home offers around 6,500 square feet of living space on a very private corner lot with lusciously landscaped grounds in the heart of Hubbard Woods. The home features a first-floor primary suite and an updated white kitchen (2023) with island that opens to the family room with

  Bari Rae Kesner Coldwell Banker Realty

  1010 Hubbard Place, Winnetka, IL 60093
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  /63

  $2,450,000 Sold Sep 15, 2025

  • 3,973 Sq Ft
  • $617/SF
  • 16 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1953

  1300 Hackberry Ln, Winnetka, IL 60093

  This is the quintessential All-American Beauty nestled on private lane in desirable Winnetka on a half acre with a pool! This home was completely rebuilt and redsigned for today's lifestyle in (2003-2004) - it is impeccable inside and out! Not much remains of the original home. The attention detail is everywhere...outstanding craftmanship and exceptional millwork throughout. A large foyer with

  Megan Mawicke @properties Christie's International Real Estate

  1300 Hackberry Ln, Winnetka, IL 60093
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  /22

  Est $553,610 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,642 Sq Ft

  630 Winnetka Mews Unit 402, Winnetka, IL 60093

  630 Winnetka Mews Unit 402, Winnetka, IL 60093
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  /36

  $3,999,000

  • 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 residence combines timeless sophistication with everyday livability. With over 6 bedrooms (including an in-law/guest suite) and 7.1 baths, the home is designed to accommodate a variety of lifestyles - whether hosting large gatherings, working from home, or enjoying intimate quiet time. A sunlit two-story foyer with a sweeping

  Linda Martin Coldwell Banker Realty

  1015 Sheridan Rd, Winnetka, IL 60093
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  $2,195 - $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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  $1,820,000 Sold Sep 03, 2025

  • 5,445 Sq Ft
  • $334/SF
  • 7 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1956

  1118 Mount Pleasant Rd, Winnetka, IL 60093

  Welcome to this beautifully maintained 5 bedroom, 4.1 bathroom Colonial home with circular driveway nestled on a half acre at the end of a quiet street in Crow island offering privacy, space, and convenience. Enjoy the hard-to-find grand first-floor primary suite featuring a well designed bathroom, spacious walk-in closet and serene views of the professionally landscaped yard. Designed for easy

  Kelly Lundin Compass

  1118 Mount Pleasant Rd, Winnetka, IL 60093
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  /41

  Est $791,603 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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  /39

  $2,195,000

  • 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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  /28

  $4,300 per month

  • 3 Beds
  • 2 Baths
  • 2,200 Sq Ft
  • House for Rent

  381 Wilson St, Winnetka, IL 60093

  Welcome to 381 Wilson, a beautifully maintained and inviting Cape Cod-style home filled with warmth, character, and natural light. Perfectly situated just blocks from downtown Winnetka and the lake, this home offers the ideal blend of comfort, space, and convenience. Step into the welcoming living room, featuring lovely views of the backyard and built-in shelving-perfect for cozy evenings or

  Pamela McClamroch Coldwell Banker Realty

  381 Wilson St, Winnetka, IL 60093
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  /11

  $875,000 Sold Aug 29, 2025

  • 1,920 Sq Ft
  • $456/SF
  • 53 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1928

  1253 Cherry St, Winnetka, IL 60093

  Motivated seller! A beautiful red brick home, center entrance colonial, in a prime Winnetka location that gushes with natural sunlight. The combination of a prime location coupled with a superb floor plan and great bones puts this in a unique category all by itself. Walk to Crow Island, Skokie, Washburne and park district field/sports complex.: two fireplaces, wood burning and gas, walk up attic

  Misael Chacon Beycome brokerage realty LLC

  1253 Cherry St, Winnetka, IL 60093
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  /29

  Est $962,827 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,637 Sq Ft

  1103 Willow Rd, Winnetka, IL 60093

  1103 Willow Rd, Winnetka, IL 60093
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  /58

  $3,150,000

  • 6 Beds
  • 5.5 Baths
  • 6,384 Sq Ft

  646 Prospect Ave, Winnetka, IL 60093

  Extraordinary opportunity for an in town oasis in the heart of East Winnetka on ~ 1/2 acre of lushly landscaped grounds with walk to everywhere. A private, fully renovated classic located in a premier location with 150 ft frontage, just steps to town, train, beach, Community House and more. Meticulously transformed and completely reimagined inside and out with one of the best first floor living

  Paige Dooley Compass

  646 Prospect Ave, Winnetka, IL 60093
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  /11

  $2,045 per month

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

  910 Green Bay Rd Unit 918-3I, Winnetka, IL 60093

  910 Green Bay Rd Unit 918-3I, Winnetka, IL 60093
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  /85

  $2,550,000 Sold Aug 29, 2025

  • 4,591 Sq Ft
  • $555/SF
  • 78 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1976

  1098 Fisher Ln, Winnetka, IL 60093

  Welcome to your dream home, just steps from the Hubbard Woods shops restaurants, park and train, and Lake Michigan. Set on over an acre with lush lawns and ravine views, this property offers a tranquil setting like no other. Enjoy an outdoor spa with a fireplace and outdoor shower, all with breathtaking views and privacy. Inside, find a beautiful kitchen with a center island which opens to the

  Joanne Hudson Compass

  1098 Fisher Ln, Winnetka, IL 60093
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  /16

  Est $668,551 Not Listed For Sale

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

  680 Green Bay Rd Unit 201, Winnetka, IL 60093

  680 Green Bay Rd Unit 201, Winnetka, IL 60093
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  /49

  $3,150,000 Pending

  • 5 Beds
  • 7 Baths
  • 5,174 Sq Ft

  647 Garland Ave, Winnetka, IL 60093

  Take advantage as this is the ONLY new construction home currently available in Winnetka! Award-winning TREND Construction has once again delivered with this stunning new build, offering nearly 6,000 sq. ft. of sun-drenched living across 4 finished levels. With a fresh, tranquil aesthetic woven throughout, this home is the perfect mix of timeless architecture and modern lifestyle. Tucked on a

  Jena Radnay @properties Christie's International Real Estate

  647 Garland Ave, Winnetka, IL 60093
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  /58

  $1,995 - $2,550 per month

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

  894 Green Bay Rd, Winnetka, IL 60093

  Renovated vintage courtyard building in the heart of the Hubbard Woods district of Winnetka.

  894 Green Bay Rd, Winnetka, IL 60093
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  /2

  $31,250,000 Sold Aug 29, 2025

  • 13,894 Sq Ft
  • $2,249/SF
  • 145 Days On Market

  • 7 Beds
  • 13 Baths
  • Built 1928

  419 Sheridan Rd, Winnetka, IL 60093

  Defining a league of its own, this is the chance of a lifetime to own the most iconic lakefront estate in IL. The "Windsor House" has been elevated to a new grandeur of living with a best in class collaboration lead by nationally recognized interior design, landscape architects & coastal engineering teams. Gloriously expanded to 2.3 acres with the purchase of 429 Sheridan transformed into a

  Jena Radnay @properties Christie's International Real Estate

  419 Sheridan Rd, Winnetka, IL 60093
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  /6

  Est $1,118,633 Not Listed For Sale

  • 4 Beds

  1580 Tower Rd, Winnetka, IL 60093

  1580 Tower Rd, Winnetka, IL 60093
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  /27

  $1,650,000

  • 3 Beds
  • 3 Baths
  • 2,960 Sq Ft

  1560 Tower Rd, Winnetka, IL 60093

  Welcome home! This beautifully updated 3-bedroom, 3-bath ranch rests on an sprawling half-acre lot with a circular driveway. Inside, a sun-filled living room with a fireplace and oversized windows offers serene views of the private backyard. A spacious family room with built-ins opens to the patio, while a separate office offers flexibility as a potential fourth bedroom. The renovated kitchen

  Selma Nemeth @properties Christie's International Real Estate

  1560 Tower Rd, Winnetka, IL 60093
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  /42

  $2,195 - $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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  /15

  $1,675,000 Sold Aug 28, 2025

  • 4,352 Sq Ft
  • $385/SF
  • 38 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 2025

  917 Willow Rd, Winnetka, IL 60093

  Enjoy a completely custom home in the heart of Winnetka. Conveniently located only blocks from Crow Island Elementary and walking distance to local favorite boutiques and restaurants including Pomeroy, 501 Local, La Taquiza and Tocco. Built by fourth generation custom home builders, this thoughtful floorplan features 5 bedrooms, 5 bathrooms, a finished lower level and a chef's kitchen ready for

  Grace Goro Compass

  917 Willow Rd, Winnetka, IL 60093
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  /2

  Est $1,691,601 Not Listed For Sale

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

  1133 Scott Ave, Winnetka, IL 60093

  1133 Scott Ave, Winnetka, IL 60093
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  /18

  $950,000

  • 4 Beds
  • 1.5 Baths
  • 2,100 Sq Ft

  979 Vine St, Winnetka, IL 60093

  Nestled just blocks from Winnetka's famed lakefront, this 4-bed/1.5-bath single-family home at 979 Vine St offers approximately 2,100 sq ft of living space, hardwood floors, a spacious kitchen, and thoughtful layout across levels. Located within walking distance to Beach Tower and downtown amenities. Homes within a one-mile radius average about $1.7-2.2 million, making this residence a rare

  Vernon Spence Jason Mitchell Real Estate IL

  979 Vine St, Winnetka, IL 60093
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  /20

  $2,195 per month

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

  545 Chestnut St Unit E817-306, 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 Unit E817-306, Winnetka, IL 60093
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  /50

  $2,050,000 Sold Aug 28, 2025

  • 4,460 Sq Ft
  • $460/SF
  • 320 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2022

  803 Pine St, Winnetka, IL 60093

  Absolute perfection in the heart of East Winnetka! Completed in 2022, this contemporary two-story masterpiece offers the perfect combination of luxury and convenience. Situated on a beautifully landscaped lot, the home is adorned with Brazilian Ipe Norwegian board siding, triple-pane windows, and a stunning modern front door, all adding to its striking curb appeal. The open-concept first floor

  Michael Kelly Compass

  803 Pine St, Winnetka, IL 60093
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  /32

  Est $5,551,963 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 4,368 Sq Ft

  473 Sheridan Rd, Winnetka, IL 60093

  473 Sheridan Rd, Winnetka, IL 60093

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