Winnetka, IL Homes for Sale

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

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

Beautifully designed ranch by renowned architect Tony Grunsfeld, perfectly situated on a private street and a spacious half-acre lot. This remarkable 4+bedroom, 4.1-bath home combines timeless architecture with thoughtful modern updates, offering comfortable, elegant living in one of the North Shore's most sought-after locations. The newly updated kitchen is the heart of the home, featuring all

Jody Dickstein @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

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

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

The house is being sold as-is. Property is being sold as a two-lot subdivision. Property is in the process of being surveyed and owner is working with Northfield to subdivide the lot. Beautify private setting with mature trees along the perimeter.

Joseph Nash @properties Christie's International Real Estate

Welcome to this spacious and sun-filled top-floor residence at the Winnetka Mews, a thoughtfully designed and impeccably managed condominium community in the heart of Winnetka. This classically updated 3-bedroom, 3-bath home enjoys south, east, and west exposures and offers exceptional one-level living with generous room sizes and an effortless floor plan. The expansive living room, anchored by a

Joanne Hudson Compass

Beautiful 3 bed 2 bath mobile home in Glenview Schoool District. Home features an open concept kitchen. 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. Community has a clubhouse, fitness center and park with walking path.Lot rent is only $1397.83 per month and no rentals allowed.

Virgilio Arreguin-Solorio My Casa Realty Corp.

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

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

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

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

Classic Hemphill Colonial on an oversized 75-foot-wide lot, completely renovated in 2014 with all the charm of a 1950s home but the newness of newer construction. What you will love is this home is all done for you with all the must haves that are hard to find- like attached garage, mudroom, high ceilings, newer windows, designer kitchen, dream primary suite, 2nd floor laundry, huge basement with

Bonnie Tripton @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

Come one, come all to this beautifully updated and refreshed colonial-style house tucked away on a quiet, tree-lined street. This home offers the rare combination of peaceful surroundings and an unbeatable location: walking distance to elementary and middle schools, and is in the New Trier High School district. Step into the welcoming entryway that flows easily to all parts of the house. A

Tim Chung Berkshire Hathaway HomeServices Chicago

Tucked into a very private setting on a beautiful 1/3-acre lot in Winnetka, this mid-century modern ranch home offers timeless design and exceptional indoor-outdoor connection. Floor-to-ceiling windows fill the home with natural light and frame serene views throughout. A spacious great room and dining room combination creates an inviting, open layout ideal for everyday living and entertaining.

Brandy Simon Engel & Voelkers Chicago North Shore

Great opportunity to own this one of a kind 4 bed, 3.5 bath townhome situated in the heart of Winnetka; close to beach, parks, schools, Metra station and shops. Exquisite finishes including 10-foot ceilings, white custom cabinets, top-of-the-line appliances (Sub-Zero, Bosch, Thermador), hardwood floors & more. The Open concept on the first floor is perfect for your daily lifestyle or

Rita Rezko Coldwell Banker Realty

READY FOR OCCUPANCY FEBRUARY 2026! 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

Susan Maman @properties Christie's International Real Estate

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