Colonial Homes for Sale in Winnetka, IL

This extraordinary residence, originally dating to the 1920s and completely rebuilt in 2010-including a fully excavated lower level-offers an exceptional blend of timeless architectural character and refined modern luxury across four impeccably finished levels. Set on an expansive 75 x 187 lot, the stately brick exterior, enhanced by a handsome porte cochere, creates a memorable and elegant

Joanne Hudson Compass

The time is NOW to jump on this "southern charm" architectural beauty on exclusive Woodley Road. Beautifully appointed on a magnificent 1.5 acre lush lot with rolling greens, this estate is in prime position to be elevated to the next level of luxury. With over 8500 square feet of classic tasteful space over three floors of living, this house could never be duplicated close for the list price as

Jena Radnay @properties Christie's International Real Estate

Classic cedar shake Colonial on an exceptional 100-foot-wide lot in East Winnetka, just moments from the train, schools, beaches and town. Thoughtfully renovated with a fresh coastal aesthetic, this light-filled home beautifully blends timeless architectural detail and old-world craftsmanship with today's airy, modern style. A welcoming foyer opens to a gracious living room with hardwood floors,

Colleen Archer Daugherty @properties Christie's International Real Estate

Exceptional East Winnetka Georgian on serene and lush . 4-acre grounds (96x160) with sweeping views of the Village Green. Architecturally significant and award-winning William Aiken classic restored and preserved to the modern standard, including a 2007 addition. Just a short walk to everything - town, train, beaches, school, and more - with your own private backyard garden oasis, this home

Paige Dooley Compass

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

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

Picture perfect 4 bed, 3.1 bath colonial farmhouse set on a deep (50 X 178) lot in the coveted "tree streets" of Winnetka. (prime location - walking to preschool thru 8th grade) Lovingly renovated and maintained, 1082 Ash offers an artful blend of charm, modern amenities, and the finest of finishes. This home boasts gracious rooms, timeless architectural details, and exceptional millwork

Sara Sullivan Compass

Bright, spacious, and beautifully maintained, this charming home offers timeless character, gracious proportions, and an exceptional in-town location on a lush, deep lot with a gorgeous patio with thoughtfully designed seating wall - perfect for entertaining and outdoor enjoyment. High ceilings, classic architectural details, and abundant natural light create a warm and inviting atmosphere

Joanne Hudson Compass

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

736 Cummings has it all - charming curb appeal and turnkey living after an 18-month extensive renovation in one of the North Shore's most desirable, family-friendly neighborhoods. A new 2-story rear addition (completed 2021 by Edward A. Anderson Co.) plus whole-house improvements inside and out create a fabulous first-floor circular plan ideal for today's lifestyle. The showstopper is the

Ted Pickus @properties Christie's International Real Estate