Winnetka, IL Homes for Sale

Striking stucco and stone home offers luxurious living in a highly desirable in-town location. From the moment you step inside, the elegant entryway welcomes you with timeless details and a sense of warmth. The formal living room, anchored by a beautifully crafted remote-control gas fireplace, opens to a sophisticated dining room-perfect for both intimate dinners and holiday gatherings. At the

Annie Cobb Challenger Baird & Warner

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

Looking for an East Winnetka home full of charm to check all of your boxes? Look no further! Premiere location - walk, cycle, skip to Greeley or New Trier schools, town, train, and lake - it's all here! A covered front entry porch draws you into the welcoming foyer. This spacious open floor plan was designed for ease of living with great traffic "flow" and gobs of natural light thru-out! The

Sally O'Donnell @properties Christie's International Real Estate

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

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

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

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

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

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

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

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

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

Welcome to 567 Provident. Ideally located just blocks from the train, schools, and all your favorite Winnetka shops and restaurants, this stylish in-town gem is the one you've been waiting for. With 5 bedrooms, 4.1 baths, and a terrific floorplan spread across four levels, this home offers unexpected space, flexibility, and charm. Originally taken down to the studs and rebuilt in 2002, the

Kathryn Moor Compass

Enjoy lake breezes on quiet coveted lane, steps to Centennial Park, Elder Beach, train, and schools. Classic 5-bedroom, 3.5-bath center entrance colonial offers a wonderful lifestyle, blending timeless design and solid construction with thoughtful modern updates. A gracious foyer highlights a gracious staircase welcomes you into a beautifully flowing floor plan designed for comfortable living

Paige Dooley Compass

Coveted Hedge Row Penthouse, HARD TO FIND ONE FLOOR living in the Heart of Winnetka! This Northwest *End unit - is on the market for the first time! This is one of only a few on the top floor that are on the *BACK* side of the building - so you don't face Green Bat Road and the train tracks - and no one is above you - so it is quiet!! This 2 bedroom, 2 bath + den condo is spacious and neutral.

Megan Mawicke @properties Christie's International Real Estate

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

Welcome to 1101 Oak Street - a beautifully updated home in the heart of the tree streets of Winnetka, offering the perfect blend of comfort, functionality, and fun. With 4 bedrooms, 2.1 baths, and an attached 2-car garage, this home is designed for easy everyday living and effortless entertaining. Step into a light-filled living room with gorgeous hardwood floors, seamlessly flowing into a

David Chung Compass

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

Spectacular home situated on 1/2 acre with lush landscaping on one of Winnetka's prettiest streets. This inviting home offers generous living rm w/fireplace, dining rm w/ fireplace, family rm w/fireplace, updated kitchen with quartz countertops, office with built-ins and screened-in porch overlooking gorgeous salt water pool. Beautifully updated, freshly painted, hardwood floors, new carpeting

Margaret Murphy Burton @properties Christie's International Real Estate

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

Tucked away on a serene cul-de-sac just steps from downtown Winnetka and Lake Michigan, this striking contemporary residence offers refined living in one of East Winnetka's most coveted locations. Designed by Gary Lee Partners and award-winning principal architect Sharlene Young, the home is a masterful expression of modern elegance, where innovative materials and meticulous craftsmanship create

Michael Canzolino Chicago Properties Firm

Unbeatable location, Award winning Hubbard Woods school, and the most wonderful neighborhood are waiting for you! Nestled in the heart of sought-after Winnetka, this 4-bedroom, 2.5-bath home offers endless possibilities on one of Hubbard Woods' most iconic streets. With only two owners since its construction, the home has been updated for comfort and ease of living, featuring a new HVAC system

Maria Welch Perennial Properties

Sophisticated Living in the Heart of Winnetka Step into timeless elegance with this meticulously crafted custom home, ideally located on a picturesque tree-lined street in one of Winnetka's most desirable neighborhoods. Built in 2005, 384 Provident Avenue offers nearly 3,500 square feet of thoughtfully designed living space with quality craftsmanship, architectural character, and exceptional

Scott Fishman Worth Clark Realty

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

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

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

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

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

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

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

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

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