Winnetka, IL Homes for Sale under $2,000,000

BRAND NEW ROOF JUST INSTALLED WITH TRANSFERABLE WARRANTY!! Beautifully maintained home offering over 4,300 square feet above grade on a rare 0.53-acre corner lot in a sought-after Winnetka location. The centerpiece of the home is the dramatic main living space featuring soaring vaulted cathedral ceilings, abundant natural light, and an impressive open feel that creates an immediate sense of scale

Cody McGuire @properties Commercial

Exceptional 4-bedroom, 2.1-bath home on Winnetka's coveted Tree Streets, offering an expansive third-floor loft and situated on a 50' x 187' deep lot. Blending timeless charm with thoughtfully designed living spaces, this home is filled with natural light, soaring ceilings, and beautiful hardwood floors throughout. A welcoming covered front porch leads into gracious living and dining rooms, while

Selma Nemeth @properties Christie's International Real Estate

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

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

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

They don't build them like this anymore, but they should! This solidly built custom Hemphill home is ideally located in sought-after East Winnetka and offers timeless character, quality craftsmanship, and thoughtful updates. Built in 1936 with exceptional materials and lovingly maintained by only two owners, this home combines classic elegance with modern comfort. The spacious living room

Cha McDaniel @properties Christie's International Real Estate