Colonial Homes for Sale in Winnetka, IL

A RARE OPPORTUNITY...in the HEART of East Winnetka, this iconic home is among the Village's most admired residences! Commanding an elevated setting atop Arbor Vitae, the magnificent home was designed by renowned architects Otis & Clark and has earned its grand reputation as Winnetka's own "Castle on the Hill." It boasts one of the most exceptional backyard retreats! Featured in Luxe Magazine and

Megan Panje-Wilson Jameson Sotheby's International Realty

Tucked away on one of Winnetka's most prestigious and serene lanes, this estate offers a rare blend of timeless North Shore elegance and a sense of true sanctuary. This isn't just a home; it's a sprawling residence designed for a lifestyle of both grand-scale entertaining and quiet, sun-drenched mornings. From the moment you pull up the winding drive, the home's commanding presence and lush,

Michael Mitchell @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 renovated and thoughtfully reimagined, this exceptional brick and stucco Colonial located in the heart of Hubbard Woods sits on an expanded 64 X 160 parcel, blending timeless architecture with today's most desired amenities and refined finishes. A total interior renovation completed in 2004 with added exterior renovation in 2006 and 2017 redesigns, transformed the home into a

Sara Sullivan Compass

Located in the heart of Winnetka and within the highly sought-after Crow Island School District, this impeccably maintained 5-bedroom, 3.1-bath home checks every box. Thoughtfully reimagined and beautifully updated, the first floor offers exceptional flow, abundant natural light and timeless finishes throughout. At the center of the home is the stunning kitchen, completely gutted and renovated in

Catherine Dunlop @properties Christie's International Real Estate

Generational opportunity...the chance of a lifetime now awaits in one of Winnetka's most premier "off lake" enclave neighborhood...936 Sunset Road with two golden options for this exclusive real estate offering. This extraordinary Ralph Lauren vibe, country ranch is all about casual elegance with a desirable first floor primary suite. Set on a magnificent 1.29 acre lot, this property now INCLUDES

Jena Radnay @properties Christie's International Real Estate

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

Inspired by timeless French Eclectic architecture and impeccably built in 2007, this extraordinary residence offers an exceptional blend of architectural character, refined craftsmanship, and modern luxury. Ideally located just blocks from Lake Michigan, top-rated schools, parks, town, and train, the home sits on a beautifully landscaped lot designed for both elegant entertaining and everyday

Kelly Lundin Compass

It's time to unveil the pinnacle of lakefront living in IL, as this newer construction estate is better than brand new construction as it encompasses features that could never be built today with the new lakefront building ordinances. Try to top this...your personal wellness club that is only 20 steps out to your own private, 141-foot wide, sandy beach with indoor pool, sauna, and

Jena Radnay @properties Christie's International Real Estate

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

Situated in the heart of Glencoe's most desirable neighborhood, this beautiful 4-bedroom, 2.1-bathroom home offers a rare blend of modern luxury and timeless elegance. Perched on a massive corner wooded lot, the property is not only beautiful and tranquil but also creates options galore for expansion should one choose. The main level of the home features hardwood floors, a gracious living room

Connie Grunwaldt @properties Christie's International Real Estate