Winnetka, IL Homes

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  /34

  $900,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,801 Sq Ft

  228 Poplar St, Winnetka, IL 60093

  This bright and expanded east Winnetka bungalow is move-in ready and larger than meets the eye! It's a spacious 4-bed, 3-bath home with a main floor that features a large and sunny living room, separate dining room, updated eat-in kitchen, two bedrooms and a full bath. The sizeable second-floor primary bedroom has a sitting area where you can enjoy the treetop views. The sunny bathroom on this

  

  Debbie Mora Evans

  Coldwell Banker Realty

  (224) 263-1133

  228 Poplar St, Winnetka, IL 60093
• Explore Winnetka

• 

  

  

  /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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  /27

  $1,825,000 Sold Oct 31, 2025

  • 2,960 Sq Ft
  • $617/SF
  • 2 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1955

  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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  /41

  Est $2,227,363 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 3,828 Sq Ft

  110 N Sheridan Rd, Winnetka, IL 60093

  110 N Sheridan Rd, Winnetka, IL 60093
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  /58

  $2,850,000 Open Sun 11AM - 1PM

  • 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
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  /29

  $8,800 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
• 

  

  /22

  $261,000 Sold Oct 31, 2025

  • 30 Days On Market

  • 2 Beds
  • 1 Bath

  1101 Merrill St Unit M1, Winnetka, IL 60093

  Welcome to this beautifully refreshed, rarely available 2-bedroom condominium perfectly situated in the vibrant heart of Hubbard Woods. Here, you're just steps from the train, boutiques, cafes, fine dining, and the sparkling shoreline of Lake Michigan-making it the ultimate in convenient, walkable living. Inside, the home blends timeless character with thoughtful updates. All-new windows flood

  Hilde Wheeler Carter Coldwell Banker Realty

  1101 Merrill St Unit M1, Winnetka, IL 60093
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  /34

  Est $2,450,145 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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  /55

  $2,195,000

  • 4 Beds
  • 2.5 Baths
  • 3,667 Sq Ft

  1161 Pine St, Winnetka, IL 60093

  Welcome to your serene oasis nestled on a private .85-acre lot in the heart of Winnetka. This enchanting home greets you with a gated drive and is surrounded by mature trees, offering unmatched privacy. Inside, the living room boasts a cozy fireplace, while the updated kitchen flows into a adjacent dining room. The family room, also with a fireplace, opens to a patio and spacious yard, offering

  Joanne Hudson Compass

  1161 Pine St, Winnetka, IL 60093
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  /2

  $2,250 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 you're 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

  896 Green Bay Rd Unit 7, Winnetka, IL 60093
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  /2

  $4,250,000 Sold Oct 30, 2025

  • 5,479 Sq Ft
  • $776/SF
  • 137 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 1922

  90 Locust Rd, Winnetka, IL 60093

  Experience the perfect fusion of timeless elegance and contemporary luxury at 90 Locust Road. Set upon over an acre of land, this majestic brick Georgian welcomes you through wrought iron gates and along a newly crafted circular driveway to its grand entrance. Step into the exquisite parlor, adorned with high ceilings, stenciled wood floors, and intricate dentil moldings, serving as the heart of

  Sarah Dwyer Compass

  90 Locust Rd, Winnetka, IL 60093
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  /29

  Est $2,116,056 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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  /46

  $2,739,000

  • 6 Beds
  • 6 Baths
  • 7,000 Sq Ft

  62 Woodley Rd, Winnetka, IL 60093

  Gracefully tucked away on 1.55 acres of lush manicured grounds, 62 Woodley Road is a true Southern-inspired masterpiece reimagined for today's living. From the moment you approach the iconic black lacquered screen door with its Chippendale detail, you're drawn into a world of classic sophistication. Step inside to a grand foyer entrance where timeless black and white checkered marble floors meet

  Jena Radnay @properties Christie's International Real Estate

  62 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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  /35

  $1,675,000 Sold Oct 29, 2025

  • 3,807 Sq Ft
  • $440/SF
  • 4 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1958

  1340 Westmoor Trail, Winnetka, IL 60093

  This timeless 4 bedroom 3.1 bathroom white brick split-level home sits on a beautifully landscaped 1/2-acre lot on a quiet, private street. A true Winnetka gem- this Hemphill home has 3,800 SF! The property offers the rare convenience of both an attached garage and a circle driveway, with a welcoming bluestone walkway leading to the front door. Inside, a bright foyer opens to sun-filled living

  Bonnie Tripton @properties Christie's International Real Estate

  1340 Westmoor Trail, Winnetka, IL 60093
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  /20

  Est $892,000 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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  /82

  $2,888,000

  • 5 Beds
  • 5 Baths

  331 Sheridan Rd, Winnetka, IL 60093

  East Winnetka One-of-a-Kind Home with Private Beach Access. Tucked away on an exclusive private lane, this exceptional East Winnetka residence offers a rare opportunity to enjoy privacy, luxury, and direct access to your own private beach. Recently renovated, 5 bedrooms, 3 baths + 2 half baths home seamlessly blends timeless elegance with modern sophistication, featuring premium finishes and

  Kathleen Whalen @properties Christie's International Real Estate

  331 Sheridan Rd, 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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  /49

  $3,070,000 Sold Oct 28, 2025

  • 5,174 Sq Ft
  • $593/SF
  • 6 Days On Market

  • 5 Beds
  • 7 Baths
  • Built 2025

  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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  /41

  Est $757,998 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
• 

  

  /49

  $2,499,900

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

  180 Apple Tree Rd, Winnetka, IL 60093

  The perfect Halloween block to trick-or-treat on as this storybook Cape Cod set on enchanting Apple Tree Road complete with that magical sidewalk to Crow Island School 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 fantastic curb

  Jena Radnay @properties Christie's International Real Estate

  180 Apple Tree Rd, Winnetka, IL 60093
• 

  

  /20

  $6,500 per month

  • 5 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • 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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  /53

  $2,650,000 Sold Oct 27, 2025

  • 5,904 Sq Ft
  • $449/SF
  • 6 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1906

  755 Lincoln Ave, Winnetka, IL 60093

  The iconic front porch has you at hello...welcoming you to this exceptionally updated classic on an oversized (100' wide) professionally landscaped yard on one of East Winnetka's most desirable streets! Masterful renovations have enhanced the home's historic charm with an air of elevated contemporary aesthetic, preserving the timeless elegance while seamlessly incorporating updates to exceed

  Paige Dooley Compass

  755 Lincoln Ave, Winnetka, IL 60093
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  /52

  Est $4,015,112 Not Listed For Sale

  • 6 Beds
  • 9 Baths
  • 10,753 Sq Ft

  102 Longmeadow Rd, Winnetka, IL 60093

  102 Longmeadow Rd, Winnetka, IL 60093
• 

  

  /36

  $3,999,000 Open Sun 2PM - 4PM

  • 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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  /76

  $1,750 - $2,250 per month

  • 1 - 2 Beds
  • 1 Bath
  • 650 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
• 

  

  /36

  $1,385,000 Sold Oct 27, 2025

  • 2,810 Sq Ft
  • $493/SF
  • 14 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1905

  274 Ridge Ave, Winnetka, IL 60093

  Beautiful colonial home located on a deep lot in prime Winnetka location, walk to schools, town, Metra. Architectural detail and charm abound throughout. Gracious entrance hall, living room with custom built in shelving and fireplace. Fantastic high end kitchen opens to spacious family room featuring lovely built ins, vaulted ceiling & fireplace. French doors from both the family room and dining

  Mary Haight Himes Compass

  274 Ridge Ave, Winnetka, IL 60093
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  /5

  Est $3,372,690 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
• 

  

  /52

  $4,560,000

  • 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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  /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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  /7

  $2,350,000 Sold Oct 24, 2025

  • 4,433 Sq Ft
  • $530/SF

  • 5 Beds
  • 5.5 Baths
  • Built 2025

  466 Chestnut St, Winnetka, IL 60093

  Custom built new construction in the heart of Winnetka with open floor plan. House is designed for seamless living between all 4 floors, fabulous staircase being a focal point, lit by the dramatic two-story window unit. Kitchen will delight any chef with professional grade SubZero/Wolf appliances package, large island, custom cabinets and walk-in pantry. Fully customizable office/living room

  Robert Milkowski Berger & Co. Realtors Ltd

  466 Chestnut St, Winnetka, IL 60093
• 

  

  /30

  Est $2,079,103 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
• 

  

  /51

  $2,499,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 5,500 Sq Ft

  1004 Oak St, Winnetka, IL 60093

  Nestled in the vibrant heart of Winnetka, 1004 Oak Street is a 2015-built, Nantucket-style masterpiece that redefines luxury living. Perfectly positioned just steps from the train, charming downtown, acclaimed restaurants, serene parks, and top-rated schools, this custom home on an oversized corner lot seamlessly blends timeless elegance with everyday functionality. The exterior stuns with

  Colleen Archer Daugherty @properties Christie's International Real Estate

  1004 Oak St, Winnetka, IL 60093
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  /2

  $2,195 per month

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

  811 Elm St Unit A07C, Winnetka, IL 60093

  811 Elm St Unit A07C, Winnetka, IL 60093
• 

  

  /33

  $1,925,000 Sold Oct 23, 2025

  • 4,544 Sq Ft
  • $424/SF
  • 45 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1930

  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

  355 Myrtle 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
• 

  

  /39

  $2,295,000 Pending

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

  386 Fairview Ave, Winnetka, IL 60093

  Situated in the desirable Greeley School District, this stunning 5-bedroom, 3.5-bath home is just one block from the lakefront and a short walk to charming downtown Winnetka. With over 4200sqft of above ground living space the fully finished basement is not included in the size! Designed for both style and function, the home showcases a chef's kitchen by Benvinuti & Stein with Viking, Sub-Zero,

  Alexa Hara @properties Christie's International Real Estate

  386 Fairview Ave, Winnetka, IL 60093
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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

  82 Woodley Rd, Winnetka, IL 60093
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  /46

  $2,607,500 Sold Oct 17, 2025

  • 7,215 Sq Ft
  • $361/SF
  • 112 Days On Market

  • 8 Beds
  • 7 Baths
  • Built 1929

  1250 Westmoor Rd, Winnetka, IL 60093

  Upon entering the grounds of this remarkable English Manor Home through the grand stone circular driveway adorned with pillars, you're greeted by an impressive foyer featuring Paradiso marble flooring inlaid with creamy travertine. This area provides access to the first-floor rooms and leads to a 1,500-square-foot elevated bluestone terrace. The elegant living room, with its bay window, offers

  Dinny Dwyer Compass

  1250 Westmoor Rd, Winnetka, IL 60093
• 

  

  /16

  Est $584,501 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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