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Winnetka, IL Homes for Sale

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  • /45

    $2,100,000

    • 5 Beds
    • 6 Baths
    • 3,921 Sq Ft

    1333 Tower Rd, Winnetka, IL 60093

    Beautifully reimagined in 2023, this custom Hemphill-designed home blends modern elegance with timeless craftsmanship. This sophisticated Winnetka home is completely transformed, including new electrical and plumbing, an updated floor plan, bay windows, and new exterior doors, while maintaining the charm and character of original plaster crown moldings and Hemphill's signature wrought-iron

    Marta Lazic Redfin Corporation

    1333 Tower Rd, Winnetka, IL 60093
  • /63

    $4,799,000

    • 5 Beds
    • 7 Baths
    • 6,697 Sq Ft

    528 Roslyn Rd, Kenilworth, IL 60043

    Stunning French Manor house on one of East Kenilworth's most beautiful streets. Stylish and sophisticated, this unique home is perfectly situated near the lake, train, Sears School, and New Trier High School. Luxurious landscaping envelopes the property, highlighted by a serene backyard pool. Expansive marble foyer opens to gracious living room and charming dining room. Dramatic floating

    Dayle Lively Baird & Warner

    528 Roslyn Rd, Kenilworth, IL 60043
  • /57

    $2,735,000

    • 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
  • /21

    $7,275,000

    • 6 Beds
    • 7.5 Baths
    • 15,000 Sq Ft

    43 Indian Hill Rd, Winnetka, IL 60093

    New magnificent transitional home situated on 1 acre picturesque lot with approximately 15,000 square feet finished space. Exterior is constructed of stone and limestone with slate roof which represents timeless construction. The house features 6 bedrooms, 7.1 bath, 4 fireplaces, spectacular Neff kitchen with top-of-the-line appliances including Sub-Zero refrigerators/freezers, luxury Wolf range,

    Milena Birov @properties Christie's International Real Estate

    43 Indian Hill Rd, Winnetka, IL 60093
  • /71

    $3,199,900

    • 6 Beds
    • 7 Baths
    • 5,338 Sq Ft

    Unlisted Address

    Centrally located in a premiere "get to everything" A+ location, this quintessential North Shore coastal shingle home delivers the best of both worlds. Thoughtfully remodeled and reimagined by notable North Shore architect Paul Konstant that beautifully blends classic character with a refreshed, modern floor plan that marries timeless architecture with designer-perfected living. Step inside to a

    Jena Radnay @properties Christie's International Real Estate

    Unlisted Address
  • /38

    $3,750,000

    • 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
  • /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 and luxury at its finest. Recently renovated, 5 bedrooms, 3 baths + 2 half baths home seamlessly blends timeless elegance with modern sophistication, featuring premium finishes and meticulous attention to detail

    Kathleen Whalen @properties Christie's International Real Estate

    331 Sheridan Rd, Winnetka, IL 60093
  • /18

    $5,975,000

    • 7 Beds
    • 8.5 Baths
    • 11,000 Sq Ft

    455 Sheridan Rd, Winnetka, IL 60093

    New magnificent transitional home with approximately 11,000 square feet finished space. Exterior is constructed of brick and limestone with slate roof which represents timeless construction. Close to Plaza del Lago with its numerous shops and restaurants, Kenilworth beach, schools and train the house features 7 bedrooms, 8.1 bath, 3 fireplaces, spectacular kitchen with top-of-the-line appliances

    Milena Birov @properties Christie's International Real Estate

    455 Sheridan Rd, Winnetka, IL 60093
  • /53

    $5,349,000

    • 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
  • /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
  • /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
  • /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 a few blocks to Tower Road Park/ beach - Lake Michigan and Lloyd Park Boat Launch.. Steps to Green Bay Train - for biking, running, and casual strolls. Plus

    Vernon Spence Jason Mitchell Real Estate IL

    979 Vine St, Winnetka, IL 60093
  • /37

    $1,299,000

    • 4 Beds
    • 3 Baths
    • 2,316 Sq Ft

    1295 Sunview Ln, Winnetka, IL 60093

    Exciting chance to refashion this light-filled ranch home to your personal vision. Large windows throughout the home offer beautiful views and light. The spacious kitchen opens to the vaulted family room. The master bedroom and second bedroom are on the first floor, plus two full baths, family room, living room, dining room, and screened porch. Outdoors, there is an expansive stone patio and pond

    Margaret Goss @properties Christie's International Real Estate

    1295 Sunview Ln, Winnetka, IL 60093
  • /26

    $1,550,000

    • 3 Beds
    • 3.5 Baths
    • 3,146 Sq Ft

    764 Boal Pkwy, Winnetka, IL 60093

    Set amidst a stunning wooded backdrop between the tranquil Skokie Lagoons and the lush Winnetka Golf Club, this remarkable home offers three bedrooms and 3.1 baths across more than 3,000 square feet of thoughtfully designed living space. Situated at the end of a peaceful lane, the setting is as serene as it is beautiful. The interiors feature exceptional open spaces with elegant hardwood floors

    Gloria Matlin Compass

    764 Boal Pkwy, Winnetka, IL 60093
  • /14

    $55,000

    • 3 Beds
    • 2 Baths

    1300 W Branch Rd, Winnetka, IL 60093

    Affordable 3-bedroom, 2-bath mobile home with tons of potential! This home offers a functional layout with a separate kitchen and living area. The primary bedroom features its own bathroom and a spacious closet. This charming home is located with a school bus stop right out front-perfect for busy mornings. Located close to shopping, schools, and main roads-come take a look and imagine the

    Diana Gonzalez Luna Real Estate Inc.

    1300 W Branch Rd, Winnetka, IL 60093
  • /11

    $90,000

    • 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
  • /28

    $1,099,000

    • 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
  • /3

    $1,345,000

    • Land
    • 1.36 Acres
    • $988,971 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
  • /20

    $16,750,000

    • 7 Beds
    • 8.5 Baths
    • 17,000 Sq Ft

    501 Sheridan Rd, Kenilworth, IL 60043

    New lakefront magnificent transitional home with approximately 17,000 square feet finished space. This house has oversized windows with nonrestricted lake vews and a future private beach.Exterior is constructed of stone and limestone with slate roof which represents timeless construction. Close to Plaza del Lago with its numerous shops and restaurants, Kenilworth beach, schools and train the

    Milena Birov @properties Christie's International Real Estate

    501 Sheridan Rd, Kenilworth, IL 60043
  • /6

    $2,395,000 New Construction

    • 5 Beds
    • 5.5 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, IL, a North Shore village bordering Lake Michigan, is known for its scenic beauty and small-town charm. With a population of approximately 12,700, it offers a mix of historic and modern homes, including early 1900s farmhouses, bungalows, Colonial and Tudor Revivals, as well as newer luxury properties like French-style chateaus and English-inspired manors. The village is safer than the national average, making it a desirable place for families. Highly rated schools such as Crow Island School, The Skokie School, Carleton W. Washburne School, and New Trier Township High School serve the community, along with Avoca School District 37, Wilmette School District 39, and Loyola Academy.

Winnetka's attractions include several beaches like Lloyd Beach, which features a boat launch and paddleboard rentals, and the Green Bay Trail, a popular route for cyclists and hikers. The village also boasts community parks, the Winnetka Golf Club, and the A.C. Nielsen Tennis Center. Downtown Winnetka, centered around the Metra stations, is pedestrian-friendly with local businesses, dining options like Fred's Garage and Pomeroy, and shops such as The Book Stall and The Grand Food Center.

Transportation is convenient with three Metra stations—Winnetka, Hubbard Woods, and Indian Hill—providing access to downtown Chicago, just 15 miles away. The Pace bus routes and proximity to Interstate 94 further enhance connectivity. This combination of natural beauty, strong community focus, and excellent amenities makes Winnetka a unique and appealing place to live.

Frequently Asked Questions

What is the average home price in Winnetka, IL?
Homes for sale in Winnetka, IL have an average home price of $2,364,958.
How many homes have sold over the last 12 months in Winnetka, IL?
200 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 60093, 60022, 60043, 60091 and 60025.
How much do you need to make to afford a house in Winnetka?
The median home price in Winnetka is $1,824,500. If you put a 20% down payment of $364,900 and had a 30-year fixed mortgage with an interest rate of 6.23%, your estimated principal and interest payment would be $8,970 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $384K a year to afford the median home price in Winnetka. Learn how much home you can afford with our Home Affordability Calculator.
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
$1,858,000
Median Single Family Sale Price
$2,112,675
Median Townhouse Sale Price
$525,000
Median 2 Bedroom Sale Price
$625,000
Median 1 Bedroom Sale Price
$260,000
Average Price Per Sq Ft
$520
Number of Homes for Sale
12
Last 12 months Home Sales
200
Months of Supply
0.70
Median List Price
$1,824,500
Median Change From 1st List Price
-1%
Median Home Sale Price YoY Change
14%
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