Winnetka, IL Homes for Sale

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

Charming House in Winnetka with Timeless Appeal Welcome to this charming four-bedroom, 1 1/2 bath Winnetka home that beautifully blends classic character with comfortable, inviting living spaces. Warm and welcoming from the moment you walk past the stately over four-hundred-year-old Burr Oak in the front yard, this home offers a wonderful combination of livability and an in-town location.

Constance Browne Coldwell Banker Realty

A rare opportunity on one of Winnetka's most beloved neighborhood streets. Welcome to 790 Foxdale Avenue, a charming Dutch Colonial offering timeless character, a wonderful sense of community and an exceptional location in the sought-after Greeley Elementary attendance area and New Trier High School district. Foxdale is more than just a beautiful tree-lined street-it's the kind of block where

Cory Green Compass

Phenomenal value as this finely built newer construction home privately set with serene panoramic Winnetka Golf Club vistas just hit "elevated luxury" status with an impeccable 2026 no expense spared rehab. Starting off with the new stunning Chef's kitchen that radiates with extra-thick Taj Mahal honed quartzite c-tops, Perrin & Rowe fixtures, Frankie sink, Visual Comfort brushed brass pendants &

Jena Radnay @properties Christie's International Real Estate

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

***Build your dream home!!!*** Amazing opportunity in the East Winnetka neighborhood, tear down and build your forever home! Original 1913 home standing on 11,555 sf 70x165 Corner LOT. Prime Winnetka location, walking distance to lake, parks, school, Metra stop and downtown Winnetka. 'As-IS/Where-Is' Estate Sale.

Edith Schell @properties Christies International Real Estate

Completely reimagined and thoughtfully designed, 1288 Sunview is an exceptional Winnetka home set on a picturesque half-acre lot. The property has been transformed from top to bottom with a focus on design, functionality and quality, creating a home that feels entirely new while maintaining the character and setting of the original property. The spacious floor plan offers 5 bedrooms, 3 full

Mike LeFevere Compass

A rare, fully renovated and updated home offering move-in-ready luxury and thoughtful craftsmanship throughout. The primary bath was renovated down to the studs, and now offers a generous shower, private water closet, and all-new fixtures, plumbing, and lighting, plus a huge closet/dressing room with a 7-foot quartz-topped built-in with 24 custom drawers, and floor to ceiling custom built-ins.

Anne Maitland Jameson Sotheby's International Realty

A rare Winnetka offering, this distinguished 1965 Hemphill-built Georgian residence showcases exceptional main-level living on a spectacular one-acre property. With a primary suite and two additional bedrooms on the first floor, the home embraces the ease of living predominantly on one level while retaining the scale, privacy and timeless North Shore architecture for which Hemphill homes are

Monica Childs @properties Christie's International Real Estate

Set on over half an acre on private Indian Hill Road within the sought-after Greeley School District, this exceptional 6-bedroom, 6.2-bath home offers the perfect blend of timeless elegance and everyday livability. Striking curb appeal sets the tone for the gracious yet highly functional interior. A grand foyer with a dramatic curved staircase introduces beautifully scaled living spaces,

Mary Grant @properties Christie's International Real Estate

**Multiple Offers Received** Highest and Best due Tuesday 9/15 by 9am** A rare expression of extraordinary North Shore living, this quintessential red-brick Colonial sits on a 100' x 175' double lot (.39 of an acre) on coveted Hill Terrace, one of Winnetka's prettiest private lanes, in an A+ walk-to-everything location. Designed by prolific architect Bertram A. Weber, this much-loved residence

Susan Sullivan @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

Built to impress, this beautifully designed, custom crafted home is discreetly tucked in next to Crow Island Woods you will have nature at your doorstep and be perfectly situated on an amazing half-acre lot. This stunning 5 + bedroom, 6.3 bath home combines timeless architecture with thoughtful modern accents, offering a level of comfortable, elegant living in the North Shore's most sought-after

Eugene Fu @properties Christie's International Real Estate

Beautifully restored idyllic Victorian home expanded for today's living features a flexible floorplan with easy flow, generously sized rooms, dramatic ceiling heights, detailed millwork and plaster moldings, inlaid floors and an abundance of tall oversized windows. The lushly landscaped property highlighted by majestic oak trees is ideally located on a favorite east Winnetka street near lakefront

Howard Meyers Compass

Your perfect Winnetka lifestyle awaits! Grab a coffee from Hometown and walk to the beach, library, or jump on the Metra. Don't feel like cooking dinner? Head to one of the many great restaurants right in town. All are just steps away from this East Winnetka Gem. A pleasure to show, this entire condo was thoughtfully & beautifully renovated by Benvenuti and Stein with quality details and finishes

Kimberly Ann Hoegler @properties Christie's International Real Estate

Enjoy an East Winnetka lifestyle on a beautifully landscaped expansive .3 acre all brick home in an ideal location, only blocks to Tower Road beach, Hubbard Woods/Winnetka shops and restaurants, schools, parks, and train. This sophisticated Georgian offering a great circular floorplan, grandly scaled rooms filled with natural light, fabulous outdoor spaces with a fully fenced yard, and an

Eileen Collins 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

A Home That Redefines Scale and Lifestyle. With over 17,000 square feet of meticulously designed living space-including 7,500 square feet dedicated to main-floor living and entertaining-this residence represents one of the most comprehensive lifestyle homes ever built in Winnetka. Designed and built by noted builder, every element was curated for collectors, entertainers, and owners who value

Mary Maris Village Realty Group Inc

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

Set on approximately half an acre in sought-after Hubbard Woods, this five-bedroom + office, 4.1-bath home offers exceptional space, a versatile floor plan, and an outstanding North Shore location. The thoughtfully designed main level features a private office or living room, formal dining room, updated eat-in kitchen, and spacious family room overlooking the backyard, in-ground pool, oversized

Christie Ascione @properties Christie's International Real Estate

Incredible opportunity to develop, customize, or thoughtfully renovate this traditional four-bedroom home situated on a picturesque half-acre lot backing directly to the Winnetka Golf Club on a quiet, tree-lined street. Whether you're envisioning a stunning custom new construction or transforming the existing residence into your dream home, this exceptional property offers endless possibilities

Axel Cohen Compass

Storybook Cape Cod in the Heart of Winnetka...Walk to Everything! Picture-perfect curb appeal, timeless character, and an unbeatable in-town location - this home has it all! Thoughtfully expanded and beautifully updated, this home offers the charm buyers love with the space and functionality for today's lifestyle. A welcoming center entrance opens to gracious living spaces designed for both

Megan Mawicke Jameson Sotheby's International Realty

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

An inviting front porch welcomes you to this custom home designed by Reynolds Architecture. Fresh interiors with designer finishes and details create the feel of this curated residence, reflecting a modern sensibility and balance of casual and formal living. The foyer showcases herringbone hardwood floors leading to all first floor rooms. Custom cabinetry lines the hall adjacent to the elegant

Howard Meyers Compass

Basement renovation just done to add 6th bedroom that adjoins full bath! So much light enters basement through windows! 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

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

Exceptional newer construction in an A+ Tree Streets location, this French Provincial-inspired brick and limestone home offers approximately 5,000 square feet of beautifully finished living space, an outstanding floor plan and an extraordinary level of care and maintenance. Built in 2012, this 5-bedroom, 4.1-bath home is ideally located just moments from schools, parks, the train, restaurants,

Stacy Burgoon Compass

Rarely available first floor primary! 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. Owner extremely

Peggy Lewis @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

Be prepared to be impressed by this rarely available, beautifully updated top-floor 4 bedroom, 3 bath residence in the historic Winnetka Mews, perfectly positioned with a Pine Street exposure. Thoughtfully renovated with exceptional attention to detail, this sun drenched home combines gracious living spaces, timeless finishes and an abundance of thoughtfully designed storage. At the heart of the

Jenny Fisher @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

Enjoy lake breezes and seasonal views from this beautifully renovated East Kenilworth home. Tucked down a private dead-end lane east of Sheridan Road, the home was fully renovated prior to the current owner's purchase in 2021, and they have continually updated the home since - adding some amazing attributes. The home has been reconfigured for today's living with a large open floor plan which has

John Mawicke @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

Elegant, distinctive, and impeccably refreshed, this 5 bedroom & 7 bathroom home is a one-of-a-kind North Shore residence offering an exceptional lifestyle in the heart of East Kenilworth with an attached 5 car garage (EV charging capability) for the car enthusiast, an elevator and outdoor pool. A truly exceptional French Manor residence designed by North Shore architect, Paul Konstant &

Kathryn Mangel @properties Christie's International Real Estate