Winnetka, IL Homes

• 

  

  

  /33

  $2,199,000

  • 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

  355 Myrtle St, Winnetka, IL 60093
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /14

  $2,150 per month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  545 Chestnut St Unit 817-306, 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 817-306, Winnetka, IL 60093
• 

  

  

  /62

  $1,865,000 Sold Jun 13, 2025

  • 3,600 Sq Ft
  • $518/SF
  • 11 Days On Market

  • 4 Beds
  • 8 Baths
  • Built 2003

  1522 Edgewood Ln, Winnetka, IL 60093

  STUNNING HOME REBUILT IN 2024-25 ACROSS FROM NICK CORWIN PARK - UNBELIEVABLE FINISHES IN THIS STATELY BRICK AND LIMESTONE HOME IN HUBBARD WOODS. NOTE THE 2C GARAGE IS DETACHED. LIVE ACROSS FROM THE PARK, PLAYGROUND & SOCCER FIELDS. EXQUISITE DETAILS INCLUDE HANDSOME MILLWORK, TALL CEILINGS, 4 FIREPLACES, SO MUCH NEW! NEW KITCHEN, APPLIANCES, GRANITE AND STONE SURFACES, PREP ISLAND WITH

  Robin Wilson @properties Christie's International Real Estate

  1522 Edgewood Ln, Winnetka, IL 60093
• 

  

  

  /41

  Est $2,129,085 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
• 

  

  

  /49

  $2,499,000

  • 6 Beds
  • 7 Baths
  • 5,350 Sq Ft

  1423 Asbury Ave, Winnetka, IL 60093

  Better than NEW! Impeccably renovated 6BR/5.2BA center-entry colonial set on an oversized (66 x 159) professionally landscaped lot. This four-level home features abundant natural light, oversized windows, wide room openings, custom millwork and gleaming hardwood floors throughout. Spacious rooms, a current layout, high-end finishes and thoughtful design exist at every turn. First floor includes a

  Laura McCain Compass

  1423 Asbury Ave, Winnetka, IL 60093
• 

  

  /20

  $9,200 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
• 

  

  /18

  $1,400,000 Sold Jun 12, 2025

  • 2,466 Sq Ft
  • $568/SF
  • 18 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1952

  1215 Hill Rd, Winnetka, IL 60093

  This wonderful and hard-to-find 3-bedroom, 2-bathroom RANCH home sits on an expansive 110 x 200 lot. As you enter, you'll be greeted by the warmth of a sun-filled living room featuring a large bay window, built-in bookshelves, a beautiful fireplace, and a large wet bar. Adjacent to the living room is the family room, with walls of windows, a hidden dry bar, and ample closet space. The bright

  Shelley Shelly @properties Christie's International Real Estate

  1215 Hill Rd, Winnetka, IL 60093
• 

  

  /34

  Est $2,335,159 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
• 

  

  /51

  $1,999,000

  • 4 Beds
  • 5 Baths
  • 3,524 Sq Ft

  475 Maple St, Winnetka, IL 60093

  Just steps from the Village Green, this expansive 5 bedroom/3.2 bath classic sits on a sprawling .3 acre (94' frontage) a walk to everything in the most desirable east Winnetka location. A stylized architectural gem boasts the elegantly designed living space, offering classical charm with soaring ceilings and oversized windows - perfect for today's lifestyle. Enjoy breathtaking views from the

  Paige Dooley Compass

  475 Maple St, Winnetka, IL 60093
• 

  

  /13

  $1,795 per month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  894 Green Bay Rd Unit 896A-10, Winnetka, IL 60093

  Renovated 1 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 896A-10, Winnetka, IL 60093
• 

  /2

  $2,550,000 Sold Jun 12, 2025

  • 4,460 Sq Ft
  • $572/SF
  • 133 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 1912

  1155 Chatfield Rd, Winnetka, IL 60093

  Gorgeous new construction home on a quiet street in Hubbard Woods! Close to town, schools, train and the lake! Best value for new construction in Winnetka! First floor includes an open floor plan including a Chef's kitchen with high end appliances, custom cabinetry & spacious island. Kitchen flows into the family room with fireplace and French doors to patio. Too much to mention! Tons of

  Annie flanagan @properties Christie's International Real Estate

  1155 Chatfield Rd, Winnetka, IL 60093
• 

  

  /29

  Est $2,123,803 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
• 

  

  /85

  $2,799,000

  • 4 Beds
  • 4.5 Baths

  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
• 

  

  /50

  $9,100 per month

  • 4 Beds
  • 3.5 Baths
  • 2,344 Sq Ft
  • House for Rent

  1443 Scott Ave, Winnetka, IL 60093

  Adorable, freshly renovated and updated, with loads of open space and light house.This is a 4 bedroom, 3.5 bath with partially finished basement home. Conveniently located at Winnetka's Hubbard Woods, where you find shopping, restaurants, parks, train station and many more. Excellent school district with great neighborhood. This house features large kitchen with pennicula, beautiful quartz

  Derek Eisenberg Continental Real Estate Group

  1443 Scott Ave, Winnetka, IL 60093
• 

  

  /40

  $2,400,000 Sold Jun 11, 2025

  • 6,000 Sq Ft
  • $400/SF
  • 2 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1921

  495 Willow Rd, Winnetka, IL 60093

  Steps from Lake Michigan, this stunning 5BR+/4.1BA brick home is ideally situated on an expansive extra-wide lot (70x186) in a prime walk-to-everything east Winnetka location. Renovated down to the studs with an addition in 2002 plus a kitchen refresh in 2019, this home combines timeless architecture, modern sophistication and thoughtfully designed interiors boasting soaring ceilings, arched

  Paige Dooley Compass

  495 Willow Rd, Winnetka, IL 60093
• 

  

  /20

  Est $841,989 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
• 

  

  /64

  $3,299,000

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

  646 Prospect Ave, Winnetka, IL 60093

  Spectacular East Winnetka in-town oasis on almost 1/2 acre of lushly landscaped grounds offers a singular opportunity to walk everywhere from a private, fully renovated classic located in a premier location with 150 ft frontage, just steps to town, train, and beach. Meticulously transformed and completely reimagined inside and out with one of the best first floor living spaces, this 6 bedrooms

  Paige Dooley Compass

  646 Prospect Ave, Winnetka, IL 60093
• 

  

  /10

  $2,150 per month

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

  545 Chestnut St Unit E817-206, 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 E817-206, Winnetka, IL 60093
• 

  

  /89

  $5,157,000 Sold Jun 09, 2025

  • 3,117 Sq Ft
  • $1654/SF
  • 0 Days On Market

  • 6 Beds
  • 10 Baths
  • Built 2009

  675 Blackthorn Rd, Winnetka, IL 60093

  Tucked away on idyllic Blackthorn Road in the heart of Winnetka, this stunning newer-construction home offers the rare combination of privacy and convenience. Secluded, yet so close to schools, town, train and all of your favorite Winnetka shops and restaurants, the location cannot be beat. With 7 en suite bedrooms, 7 full baths, 3 half-baths, and a generous lot size of nearly a half-acre, this

  Kathryn Moor Compass

  675 Blackthorn Rd, Winnetka, IL 60093
• 

  

  /22

  Est $513,753 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
• 

  

  /46

  $2,900,000

  • 8 Beds
  • 7 Baths
  • 7,215 Sq Ft

  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
• 

  

  /57

  $2,295 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
• 

  

  /61

  $9,575,000 Sold Jun 06, 2025

  • 8,086 Sq Ft
  • $1184/SF
  • 25 Days On Market

  • 5 Beds
  • 8 Baths
  • Built 2015

  381 Sheridan Rd, Winnetka, IL 60093

  Extremely RARE opportunity to own this premier in-town "Sheridan Road-to Shore" dreamy lakefront showstopper on the best lakefront block nestled between the most posh North Shore estates! Trend Construction hit it out of the park with this new phenomenal walk-out entertainment galore lower level with a low voltage Control 4 system to run the house from anywhere in the world. Luxe designer touches

  Jena Radnay @properties Christie's International Real Estate

  381 Sheridan Rd, Winnetka, IL 60093
• 

  

  /55

  Est $2,019,521 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 3,823 Sq Ft

  191 Scott Ave, Winnetka, IL 60093

  191 Scott Ave, Winnetka, IL 60093
• 

  

  /19

  $1,995,000

  • 4 Beds
  • 5 Baths
  • 3,700 Sq Ft

  314 Woodland Ave, Winnetka, IL 60093

  Handsome Georgian home underwent a complete restoration and remodel (2016) to preserve its antique charm and vintage details. Fantastic east Winnetka location - walk to Greeley, New Trier, Lake Michigan, and commuter train. Beautiful brick exterior with slate roof sets the tone for the entire home. kitchen with Decora cabinets, two spacious pantries, eat-in bar plus table space. 3 fireplaces,

  Margaret Goss @properties Christie's International Real Estate

  314 Woodland Ave, Winnetka, IL 60093
• 

  

  /57

  $1,850 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
• 

  

  /37

  $1,000,000 Sold Jun 05, 2025

  • 1,594 Sq Ft
  • $627/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1916

  340 Walnut St, Winnetka, IL 60093

  Welcome to this charming home in East Winnetka! The delightful home boasts a bright, open floor plan that offers exceptional living space. The inviting living room features a stunning white quartz fireplace and elegant shelving, seamlessly connecting to the adjacent dining area. The spacious dining room is perfect for enjoying meals, surrounded by windows, beautiful built-ins, and charming window

  Katie Hauser Compass

  340 Walnut St, Winnetka, IL 60093
• 

  

  /28

  Est $854,305 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,972 Sq Ft

  812 Oak St Unit 203, Winnetka, IL 60093

  812 Oak St Unit 203, Winnetka, IL 60093
• 

  

  /50

  $2,190,000

  • 4 Beds
  • 4 Baths
  • 4,460 Sq Ft

  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
• 

  

  /57

  $2,295 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
• 

  

  /30

  $1,207,000 Sold Jun 05, 2025

  • 2,297 Sq Ft
  • $525/SF
  • 4 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1924

  867 Lincoln Ave, Winnetka, IL 60093

  Ideally located between downtown Hubbard Woods and Tower Road Beach, this beautifully maintained Colonial blends timeless charm with thoughtful modern updates. Step inside to find warm hardwood floors and sun-filled rooms that create an inviting, elegant atmosphere. The traditional floor plan offers a formal living room with a wood-burning fireplace, a spacious dining room perfect for gatherings,

  Cricket King @properties Christie's International Real Estate

  867 Lincoln Ave, Winnetka, IL 60093
• 

  

  /41

  Est $716,978 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
• 

  

  /70

  $2,389,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 4,600 Sq Ft

  385 Rosewood Ave, Winnetka, IL 60093

  Discover an exquisite blend of architectural brilliance and top-tier craftsmanship in this stunning home, newly constructed in 2023 in the heart of town. This home is adorned with fabulous upgrades including premium appliances, hardwood flooring throughout, extensive custom millwork (coffered ceilings, paneling, moldings, and wainscoting), 10 foot ceilings, advanced technology for seamless

  Joanne Hudson Compass

  385 Rosewood Ave, Winnetka, IL 60093
• 

  

  /16

  $2,250 per month

  • 3 Beds
  • 1.5 Baths
  • 1,400 Sq Ft
  • Condo for Rent

  953 Westmoor Rd Unit 1, Winnetka, IL 60093

  Beautiful and bright 3 Bedroom unit with large private patio. Hardwood floors throughout and bedrooms upstairs. One and one half baths and in unit laundry. One garage spot included and easy street parking. Living room dining room opens to the stone patio. Updated kitchen with stainless steel appliances. Master bedroom and 2 large bedrooms - good closet space and storage in the attic with pull

  953 Westmoor Rd Unit 1, Winnetka, IL 60093
• 

  

  /28

  $2,017,000 Sold Jun 05, 2025

  • 3,170 Sq Ft
  • $636/SF
  • 4 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2008

  1132 Oak St, Winnetka, IL 60093

  Nestled in sought after in town location. The front porch welcomes you as you enter the home! Beautiful LR and DR with hardwood floors, detailed custom molding and window treatments. Light and airy kitchen, with quartz counters, stainless steel appliances, breakfast bar, table space, planning desk, walk in pantry. Family room with hardwood floors, fireplace. Fabulous mud room with built-in

  Kathleen Doron Coldwell Banker Realty

  1132 Oak St, Winnetka, IL 60093
• 

  

  /52

  Est $3,698,686 Not Listed For Sale

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

  102 Longmeadow Rd, Winnetka, IL 60093

  102 Longmeadow Rd, Winnetka, IL 60093
• 

  

  /46

  $2,650,000 Pending

  • 5 Beds
  • 6.5 Baths
  • 5,573 Sq Ft

  260 Woodlawn Ave, Winnetka, IL 60093

  California Dreamin'..... Enjoy easy California living in this one-of-a-kind, East Winnetka, new construction home! No expense was spared in constructing this 6-bedroom, 6 1/2-bath home where every modern convenience awaits you. Situated on a .34 acre, corner lot, this private home boasts 2 large, side yards and overlooks a quiet park across the street. With south and west-facing exposure, light

  Elizabeth Smith @properties Christie's International Real Estate

  260 Woodlawn Ave, Winnetka, IL 60093
• 

  

  /25

  $2,145 per month

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

  910 Green Bay Rd, Winnetka, IL 60093

  910 Green Bay Rd, Winnetka, IL 60093
• 

  

  /51

  $2,400,000 Sold Jun 03, 2025

  • 5,300 Sq Ft
  • $453/SF
  • 1 Day On Market

  • 4 Beds
  • 5.5 Baths
  • Built 2006

  390 Hawthorn Ln, Winnetka, IL 60093

  Nestled in the heart of East Winnetka, an exceptional, "better-than-new" sophisticated home on a wider lot (63') in the best in-town, walk-to-beach/park/train/schools location designed with distinction for the most discriminating buyer. Offering a harmonious blend of modern design and luxurious living with an acute attention to detail and the finest, high-end finishes. Crisp moldings, soaring

  Paige Dooley Compass

  390 Hawthorn Ln, Winnetka, IL 60093
• 

  

  /66

  Est $3,975,173 Not Listed For Sale

  • 4 Beds
  • 9 Baths
  • 11,847 Sq Ft

  106 Longmeadow Rd, Winnetka, IL 60093

  106 Longmeadow Rd, Winnetka, IL 60093

Showing Results 1 - 40, Page 1 of 18