Colonial Homes for Sale in Winnetka, IL

Relax in this storybook setting reminiscent of rural Connecticut...An exceptional and rare opportunity to find a luxuriously simplistic, stylized Colonial classic located in the heart of Winnetka! Designed by noted architect, Paul Konstant, this breathtaking home is artfully sited on an oversized lot (120' wide) of abundant, panoramic landscaped grounds that exudes quality in every thoughtful

Paige Dooley Compass

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

An extraordinary Colonial offering timeless elegance, exceptional estate-like privacy, and breathtaking views along the 12th hole of the Winnetka Golf Course. Set on nearly one acre of beautifully landscaped grounds and positioned approximately 250 feet from the road, this property feels like a private retreat yet is just minutes from downtown Winnetka, the Metra, premier shopping, dining, and

Sarah Lyons @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

Nestled in an exceptional location, this beautifully appointed home offers the perfect combination of charm, comfort, and convenience. Just moments from vibrant downtown Winnetka, you'll enjoy easy access to outstanding restaurants, boutique shopping, the train station, and the beach-making it easy to embrace the very best of the community. Inside, the thoughtfully designed floor plan features

Anne Malone Engel & Voelkers Chicago North Shore

Stunning million dollar+ renovation of a picture perfect brick center-entry Georgian colonial ideally positioned on one of Winnetka's most coveted streets with breathtaking views. Thoughtfully reimagined and meticulously renovated from top to bottom in 2022, this exceptional residence blending timeless architecture with beautifully curated finishes, impeccable craftsmanship, and modern luxury

Paige Dooley Compass

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

A rare opportunity to own a home on one of the most sought after, serene country-like settings on the North Shore. The house is just steps from the Indian Hill Golf Club and part of the coveted Indian Hill neighborhood. Be close to other magnificent homes and wooded and mature landscaping. Only one owner since home was completed on this property in 2012. Stately and traditional two story brick

Beverly Smith @properties Christie's International Real Estate

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

This is the opportunity buyers wait for. An architecturally significant Hubbard Woods Georgian that could never be duplicated today for anywhere near this cost. Perfectly positioned on one of the neighborhood's most coveted cul-de-sac streets, this distinctive home showcases extraordinary vintage details paired with over $1.2 million in thoughtful renovations and infrastructure improvements. Step

Jena Radnay @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

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