Winnetka, IL Homes for Sale

Set at the end of a quiet, private cul-de-sac on a rare acre lot, this custom-built Georgia marble home with an inground pool showcases timeless elegance and exceptional craftsmanship in the Woodley neighborhood of Winnetka. A gracious foyer with stained glass double entry doors, marble tile floors, fresh paint, and a sparkling crystal chandelier, greets you to six bedrooms, four full baths, two

Jason Wagner Greystone Realty

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

Rarely available unique mid-century contemporary in the heart of Winnetka. Your own private paradise with a flowing interior perfect for entertaining! Soaring teak ceilings add to the Aspen style influence. Tons of windows look out to the gorgeous landscaped grounds enhanced by a pool and gazebo. This home has been beautifully maintained by the current owners.

Peggy Lewis @properties Christie's International Real Estate

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

Situated on a quiet, highly desirable street in the heart of Winnetka, 510 Provident represents a thoughtful expression of modern North Shore architecture - where structural integrity, material quality, and enduring design converge. This new construction home offers six-bedrooms, six baths, over-scaled proportions and architectural clarity throughout. Ten-foot ceilings and vaulted second-floor

John Park John Park

Set behind mature landscaping on a breathtaking and rarely available full acre, this extraordinary Winnetka residence offers the kind of space, privacy, and walk-to-everything convenience that almost never coexist. Thoughtfully reimagined through a complete gut renovation and expansion in 2010-including a new lower level, this 6-bedroom, 5.2-bath home lives beautifully for today while honoring

Julie Miller 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

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 the

Joanne Hudson Compass

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

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

New construction home with 5BR, 6Bath,2 car detached garage, will be ready by March 2026. This more than 4000 sqft house boasts thoughtfully designed living space, combining modern luxury with everyday functionality, front and back porches and second floor primary BR with balcony, two heating and cooling zones, two laundries, two dishwashers, two wine coolers. Step inside to soaring ceilings, and

Nehru Arunasalam @properties Christie's International Real Estate

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

Reimagined, refreshed, and beautifully renovated, this 4-bedroom plus office, 2 full and 2 half bath home is ideally situated in a prime East Winnetka location-just moments from Greeley, New Trier, the Indian Hill Metra stop, beaches, and parks. A thoughtfully designed main level offers a seamless flow between formal and informal living spaces. The inviting living room is anchored by a gas

Emily Smart LeMire Compass

Coveted East Winnetka location just two blocks from Tower Road Beach! This charming 5-bedroom, 3.1-bath home offers timeless character and wonderful living space, complete with an inviting front porch. The living room showcases a coffered ceiling, oversized wood-burning fireplace, and beautiful period millwork. A bright sunroom with built-in bookcases provides the perfect retreat. Hardwood floors

Christie Ascione @properties Christie's International Real Estate

Welcome to the charming chimneys. Quiet and secluded. Pretty and bright top floor unit looking out on quaint, treelined courtyard. A large living room greets you with abundant natural light and a charming, wood burning fireplace. Separate, updated white kitchen with shaker style cabinets and granite countertops. Appliances include a double oven, gas stove, dishwasher and refrigerator/freezer.

Celia Nelson @properties Christie's International Real Estate

Refined elegance meets timeless North Shore charm in this premier East Winnetka location, served by Joseph Sears School (JK-8) and New Trier High School. This beautifully updated and impeccably appointed residence offers 5 bedrooms and 4.1 baths, gracious formal living and dining rooms, and a seamless open-concept layout designed for both sophisticated entertaining and everyday living. At the

Laura Fitzpatrick @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

This mobile home features 3 bedrooms and 2 bathrooms and is located within the desirable Glenview School District. The home offers an large kitchen with an additional eating area, in addition to the large dining room. A laundry room is right off the kitchen. The master bathroom includes a full bath. Two additional bedrooms round out this spaces 45X25 mobile home. The furnace and boiler are newer.

Michelle Galindo Baird & Warner

Idyllic Cape Cod offering resort-like living with 4+ bedrooms and 5.2 baths, beautifully designed for both everyday living and exceptional entertaining. The home features a sought-after first-floor primary suite plus an additional bedroom with full ensuite bath in that wing of the home. An outstanding chef's kitchen with top-of-the-line appliances, generous workspace, and a spacious breakfast

Joanne Hudson Compass

Better than NEW! This artfully restored & renovated home has the incredible combination of a classic center entry colonial home with sophisticated formal rooms and all the current amenities for today's modern lifestyle. This four-level home features abundant natural light, oversized windows, wide room openings and gleaming hardwood floors throughout. Spacious rooms, a current layout, high-end

Laura McCain Compass

Perfectly situated in a prime East Winnetka location, this charming home offers an exceptional opportunity to enjoy one of the North Shore's most sought-after neighborhoods at an approachable price point. Just blocks from the lake, town, Metra, Greeley Elementary, and New Trier High School, the lifestyle and convenience are unmatched. Thoughtfully updated over time, the home features bright,

Danielle Wylie Baird & Warner

Blending timeless elegance with modern sophistication, this stunning 2016 Winnetka home feels better than new. Designed for light, flow, and effortless living, it features 10-foot ceilings, white oak floors, and expansive windows that fill each room with warmth. The gourmet kitchen showcases custom cabinetry, large island, and professional appliances is perfect for everyday living and

Jason Rowland Compass

Beautifully updated home offering over 4,300 square feet above grade on a rare 0.53-acre corner lot in a quiet, tree-lined Winnetka location. The heart of the home is the stunning main living space featuring soaring vaulted cathedral ceilings, creating an open, airy feel filled with natural light and delivering an immediate "wow" factor. The layout flows effortlessly for both everyday living and

Cody McGuire @properties Commercial

Traditional colonial meets resort style living. Set back from Linden Avenue for space and privacy. Light and bright interior with upgraded finishes and custom details throughout. This charming 4-bedroom, 3.5 bath home is nestled in a highly sought-after neighborhood. Enjoy the perfect blend of peaceful retreat and easy access, just a short stroll to vibrant Hubbard Woods, charming downtown

Suzanne Beu Jameson Sotheby's International Realty

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