Winnetka, IL Homes for Sale

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

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

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

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

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

Incredible Coveted Home with 5 bedrooms, 5.2 bathrooms, 3 garages on 1/3 acre property boasts Winnetka address and Kenilworth School District. Built in 2004, this beautiful brick home feels like new construction with a complete first floor renovation in 2019 and upgrades throughout the home. As you enter the sun filled foyer, you are greeted with an open floor plan and 9'.5" ceilings. Flanking

Kathryn Mangel @properties Christie's International Real Estate

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

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

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

Exceptional architecture meets thoughtful in this spectacular home with original design by Thomas Eddy Tallmadge and renovation design by Paul Konstant, all perfectly set in a park-like setting just steps from the shops, restaurants, train, and Hubbard Woods park and town. Four levels of beautifully imagined living spaces invite both grand entertaining and relaxed everyday living. Step inside

Joanne Hudson Compass

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

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

Tucked away on almost half an acre in East Glencoe, this pristine 5 bedroom, 4.2 bath light-filled Georgian brick home blends timeless architecture with thoughtfully designed interiors that balance sophistication and comfort. Inside, a dramatic two-story foyer sets the tone with gleaming stone and hardwood floors, and two elegant formal spaces: a refined living room with a fireplace and a

Susan Maman @properties Christie's International Real Estate

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

Wonderful right-size home in the heart of Winnetka...just steps from town, train, library and schools. First floor features a handsome living room with fireplace and sliding doors to the private, walled patio; a bright and white kitchen with roomy eating area, also with sliding glass doors that open to the patio plus a conveniently located 1st floor powder room. The second floor offers a primary

Joanne Hudson Compass

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

Sophisticated perfection on an extra wide lot in one of Winnetka's most picturesque neighborhoods! Breathtaking 5BR/4.1BA beauty immediately captivates with its stately facade, grand walk-up entrance and exceptional curb appeal. A seamless blend of comfortable elegance and contemporary refinement, every detail reflects thoughtful design and superior craftsmanship.A bold designer palette

Paige Dooley Compass

Estate-Owned Property in coveted Winnetka Location. Exceptional opportunity on a 9,000 sq ft lot (60 x 150) in one of Winnetka's most desirable neighborhoods. This home offers incredible potential. Renovate. Expand. Build new....up to approx. 3,600 sq ft (per current Village guidelines, to be confirmed by buyer). Ideal for downsizing or growing family...bring your ideas and plans and lets go!

Crawford Group @properties Christie's International Real Estate

This exceptional residence is nestled on one of Winnetka's most sought after "tree" streets in a walk to everything location, offering unparalleled convenience and charm. Ideally located just blocks from the train, schools and all the coveted Winnetka shops and restaurants, this in-town gem is a newer custom built 5 bedroom, 4.1 bath home offering 4 levels of flexible living space with

Anne Rodia @properties Christie's International Real Estate

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

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

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

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

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

Margaret Goss @properties Christie's International Real Estate

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

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.

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.

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

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

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

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

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