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Winnetka, IL Homes for Sale

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  • /57

    $2,949,500

    • 6 Beds
    • 6.5 Baths
    • 5,500 Sq Ft

    527 Warwick Rd, Kenilworth, IL 60043

    Fully Renovated 6BR 5.5BA Classic Home in Unbeatable East Kenilworth Location. This Elegant home sits on a large lot on one of Kenilworth's most serene streets. FIRST FLOOR: Elegant LR w/ Thibault Grasscloth Wallpaper & Custom Solid Wood Built Ins, Custom Handmade Mosaic Entry, Traditional DR w/ Brick Fireplace. Kitchen boasts both a Butler's Pantry and Prep Station, Quartz Countertops and

    Paul Harb Wilmette Real Estate & Management Company LLC

    527 Warwick Rd, Kenilworth, IL 60043
  • /71

    $4,250,000

    • 8 Beds
    • 7 Baths
    • 7,168 Sq Ft

    5 Woodley Rd, Winnetka, IL 60093

    This estate delivers the ultimate outdoor summer experience. It's time to sip 5pm summer cocktails in a true country club setting with gorgeous vistas of precisely manicured grounds from the tiered entertaining bluestone patios with the soothing sounds of the fountain trickling in the background. And as the sun sets, enjoy evenings under the stars in the tasteful, boutique hotel level hot tub

    Jena Radnay @properties Christie's International Real Estate

    5 Woodley Rd, Winnetka, IL 60093
  • /60

    $2,645,000 Open Sun 12PM - 2PM

    • 4 Beds
    • 4.5 Baths
    • 3,973 Sq Ft

    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
  • /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
  • /72

    $4,599,000

    • 6 Beds
    • 6 Baths
    • 6,639 Sq Ft

    22 Indian Hill Rd, Winnetka, IL 60093

    Nestled privately amidst the prestigious landscape of Indian Hill Road, this magnificent English manor, designed by renowned architect Edwin Clark, presents an unparalleled opportunity to immerse yourself in the epitome of understated luxury living. From its commanding position on an expansive 1.7-acre grounds, this once-in-a-lifetime estate exudes timeless elegance and refinement at every turn.

    Paige Dooley Compass

    22 Indian Hill Rd, 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
  • /39

    $4,500,000

    • 4 Beds
    • 7 Baths
    • 8,294 Sq Ft

    977 Sheridan Rd, Winnetka, IL 60093

    Perfectly situated in a discreet upscale enclave east of Sheridan road. Beautifully tucked away is where you'll find this gorgeous estate on a professionally landscaped .659 acre. With exceptional quality, elegance and design throughout there are many updates that have been done over the last 3 years. Upon entering the foyer you'll see 12-14 ceilings and gorgeous marble floors. New Kitchen with

    Kim Kelley Baird & Warner

    977 Sheridan Rd, 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
  • /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
  • /70

    $3,295,000 Open Sun 1PM - 3PM

    • 5 Beds
    • 5.5 Baths
    • 5,118 Sq Ft

    530 Essex Rd, Kenilworth, IL 60043

    Transitional, sun-filled newer construction home on an oversized lot (110 x 175) in a PRIME East Kenilworth location! This stunning home is on one of the best blocks in town, boasting over 6,000 square feet of living space with grandly scaled rooms, amazing natural light, high ceilings, beautiful windows, walnut floors throughout and 4 floors of fabulous living for today's lifestyle! The

    Megan Mawicke @properties Christie's International Real Estate

    530 Essex Rd, Kenilworth, IL 60043
  • /31

    $2,739,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 5,088 Sq Ft

    643 Abbotsford Rd, Kenilworth, IL 60043

    New construction home with over 4,600 square feet of living space and 2 car attached garage in east Kenilworth on a fantastic 200-foot-deep lot. Delivery Fall 2025. This brick home is designed for today's lifestyle with a large open floor plan on the main floor including a private office. The custom integrated kitchen is pure luxury with paneled appliances, quartzite counters, 9-foot island

    Darin Marcus Marcus Real Estate Group

    643 Abbotsford Rd, Kenilworth, IL 60043
  • /14

    $949,000

    • 3 Beds
    • 3 Baths
    • 1,920 Sq Ft

    1253 Cherry St, Winnetka, IL 60093

    Center entrance colonial, four square layout with great bones. Walk to Crow Island, Skokie, Washburne and park district field/sports complex. Two fireplaces, wood burning and gas. Update and decorate as you wish!

    Misael Chacon Beycome brokerage realty LLC

    1253 Cherry St, Winnetka, IL 60093
  • /29

    $1,999,000

    • 4 Beds
    • 3.5 Baths
    • 3,659 Sq Ft

    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
  • /45

    $1,599,000

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

    550 Oak St, Winnetka, IL 60093

    Opportunity to own and enhance a once-in-a-generation architecturally rich East Winnetka home built in 1894 and set on a beautifully landscaped .42-acre corner lot just steps from town, train, schools, Lake Michigan beaches and the Village Green. Bring your contractor with you to see this solidly built 5000 plus square foot, 5+ bedrooms, 3.2 baths vintage beauty that is surrounded by an iconic

    Paige Dooley Compass

    550 Oak St, Winnetka, IL 60093
  • /11

    $110,000

    • 3 Beds
    • 2 Baths

    804 8th St, Winnetka, IL 60093

    Beautiful 3 bed 2 bath Almost New Mobile Home Built in 2015, in Glenview School district. Home features an open concept kitchen with a big island, recessed lighting, full bath in master bathroom, big laundry room, stainless steel appliances. With a bigger driveway and big back yard with patio for all your summer gatherings. Community has clubhouse, fitness center and park near walking path. Lot

    Virgilio Arreguin-Solorio My Casa Realty Corp.

    804 8th St, Winnetka, IL 60093
  • /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
  • /15

    $20,000

    • 2 Beds
    • 1 Bath

    1327 W Branch Rd, Winnetka, IL 60093

    OWN YOUR OWN HOUSE & ENJOY YOUR PRIVACY! Fantastic MH opportunity at Sunset Village of Northfield (Glenview)! Low cost of living with $1,331.27 monthly lot rent. ------ This single-wide model with 2 parking spaces, has been updated inside & out, including new luxury vinyl plank flooring, appliances, fixtures, new ClimateGuard windows throughout, plus new exterior siding, skirting, gutters,

    Bob Parris Manchester Realty

    1327 W Branch Rd, Winnetka, IL 60093
  • /28

    $1,150,000

    • 4 Beds
    • 2.5 Baths
    • 2,380 Sq Ft

    1492 Asbury Ave, Winnetka, IL 60093

    Rehabbers-Opportunity Awaits! Have you been searching for a home on one of Hubbard Woods' most cherished streets? A place where your family can grow, in a community known for its charm and friendly community? This is that rare opportunity. This solid 4 bed, 2.5 bath home is full of potential and perfectly situated in a sought-after neighborhood with top-rated schools. With thoughtful updates

    Maria Welch Perennial Properties

    1492 Asbury Ave, Winnetka, IL 60093
  • /101

    $5,995,000

    • 5 Beds
    • 8 Baths
    • 13,482 Sq Ft

    624 Pine Ln, Winnetka, IL 60093

    Welcome to this stunning custom home designed by Morgante Wilson, with thoughtful input from discerning owners. This once in a lifetime home is nestled on a picturesque 0.86-acre lot on private Pine Lane near schools, town and train. This thoughtfully designed home is perfect for all ages, blending creativity and style throughout. The inviting entrance hall sets the tone as you walk in, leading

    Joanne Hudson Compass

    624 Pine Ln, 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
  • /55

    $4,500,000

    • 6 Beds
    • 5.5 Baths

    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
  • /55

    $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
  • /3

    $1,395,000

    • Land
    • 1.36 Acres
    • $1,025,735 per Acre

    2033 Winnetka Rd, Winnetka, IL 60093

    Rare chance to own 1.36 acres of land on beautiful Winnetka rd will provide you endless possibilities to build your dream home. Incredible opportunity to collaborate with experienced luxury builder or bring your own builder. Winnetka High School District. Amazing location- close to Northfield Park District,Westfield Shopping Center, Edens Expressway,the Glen Metra station.

    Natalya Gorodetsky Core Realty & Investments, Inc

    2033 Winnetka Rd, 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
  • /21

    $892,500

    • 4 Beds
    • 1.5 Baths
    • 1,355 Sq Ft

    979 Vine St, Winnetka, IL 60093

    Winnetka introduces a nostalgic bungalow perfectly appointed between Hubbard elementary school, shops, entertainment and restaurants! A charming fenced in yard allures guests to a beautiful entry where the floor plan unveils an open concept with a sprawling family room filled with an abundance of natural light. The family overshadows a separate sitting room with a gorgeous brick fireplace and

    Rob Morrison Coldwell Banker Realty

    979 Vine St, Winnetka, IL 60093
  • /26

    $4,495,000 New Construction

    • 5 Beds
    • 7 Baths
    • 7,500 Sq Ft

    518 Elder Ln, Winnetka, IL 60093

    Stunning new construction transitional home with approximately 7,500 square feet of meticulously finished space, the home is located on one of the most picturesque streets in East Winnetka in an unbeatable location. The home is close to town, walking distance to the beach, schools and train. This home features 6 bedrooms, 7 full baths, a show room worthy kitchen with luxury appliances including

    Matan Aharoni Coldwell Banker Realty

    518 Elder Ln, Winnetka, IL 60093
  • /38

    $1,175,000

    • 4 Beds
    • 3 Baths
    • 2,087 Sq Ft

    503 Oakdale Ave, Glencoe, IL 60022

    This sun-filled 4 bedroom, 3 full bath farmhouse style home has been extensively renovated with two brand new 2nd floor bathrooms and much, much more! The exceptional layout of this home lives larger than one would expect, offering many places for family members to retreat to and gather: a sun porch with sitting area; a formal living room; a dining room; a 1st floor bedroom/office/former nanny

    Diana Peterson AW Properties Global/Auction Works

    503 Oakdale Ave, Glencoe, IL 60022
  • /44

    $3,250,000

    • 5 Beds
    • 6.5 Baths
    • 5,600 Sq Ft

    96 Harbor St, Glencoe, IL 60022

    Serene & tranquil living awaits at this East Glencoe Tony Grunsfeld transitional ranch-like beauty set on a gorgeous half-acre lot. Steps to the lake with an outdoor pool & hot tub, this is the ultimate oasis for summer entertainment. Beautifully oriented, the exterior organically blends seamlessly into the interior space as the entire property was reimagined by its current owners. Relaxing &

    Jena Radnay @properties Christie's International Real Estate

    96 Harbor St, Glencoe, IL 60022
  • /6

    $2,395,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 4,971 Sq Ft

    150 Linden Ave, Glencoe, IL 60022

    Proposed New Construction~ Sophisticated farmhouse with a welcoming front porch with a metal roof and approximately 4500 sq ft of finished space situated on a deep 55 X 180 lot. Get in while there is still time to customize and make this your dream home. Super desirable location with close proximity to town, parks, schools, public transportation and the beach for both Hubbard Woods and Glencoe.

    Susan Maman @properties Christie's International Real Estate

    150 Linden Ave, Glencoe, IL 60022

Why Live in Winnetka

Winnetka, a North Shore village bordering Lake Michigan, is known for its beaches, parks, and proximity to the Forest Preserves of Cook County. Located about 15 miles from downtown Chicago, it offers convenient access via multiple Metra train stations. With a population of approximately 12,700, Winnetka maintains a small-town character with community and school-based activities. The area is safer than the national average, with a crime score of 1 out of 10. The neighborhood features a mix of home styles, including early 1900s farmhouses, bungalows, Colonial and Tudor Revivals, as well as newer luxury homes and more typical suburban Cape Cods and ranch-style houses. Notable attractions include Lloyd Beach, the Green Bay Trail, and the Winnetka Golf Club. Downtown Winnetka, centered around the Metra stations, is pedestrian-friendly and home to local businesses like Fred's Garage, Hometown Coffee & Juice, and The Book Stall. The village is served by highly rated schools, including Crow Island School, The Skokie School, Carleton W. Washburne School, and New Trier Township High School. Additional educational options include Avoca School District 37, Wilmette School District 39, and Loyola Academy. Transportation is facilitated by three Metra stations and Pace bus routes, with easy access to Interstate 94 for driving into Chicago.

Frequently Asked Questions

What is the average home price in Winnetka, IL?
Homes for sale in Winnetka, IL have an average home price of $2,248,257.
How many homes have sold over the last 12 months in Winnetka, IL?
208 homes have sold in Winnetka, IL over the last 12 months.
What are the most popular zip codes in Winnetka, IL?
The most popular zip codes in Winnetka, IL include 60611, 60614, 60610, 60657 and 60647.
How much do you need to make to afford a house in Winnetka?
The median home price in Winnetka is $1,795,000. If you put a 20% down payment of $359,000 and had a 30-year fixed mortgage with an interest rate of 6.77%, your estimated principal and interest payment would be $9,330 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $400K a year to afford the median home price in Winnetka.
How are the schools in Winnetka, IL?
Winnetka, IL has highly rated public and private schools. Some of the best schools in Winnetka based on Niche Grades are New Trier Township High School, North Shore Country Day School and Sacred Heart School. Browse all the schools in Winnetka, IL to learn more.

Home Trends in Winnetka, IL

Housing Trends

Median Sale Price
$1,687,500
Median Single Family Sale Price
$2,010,000
Median Townhouse Sale Price
$472,125
Median 2 Bedroom Sale Price
$605,000
Median 1 Bedroom Sale Price
$237,500
Average Price Per Sq Ft
$511
Number of Homes for Sale
25
Last 12 months Home Sales
208
Months of Supply
1.40
Median List Price
$1,795,000
Median Change From 1st List Price
-1%
Median Home Sale Price YoY Change
5%
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