Timeless elegance meets classic, high-quality updates in this stunning French Country home, perfectly situated on one of Glencoe's most coveted "President" streets. With true walkability to parks, schools, shopping, dining, recreation, and the Metra train, the location alone is a rare find - and the home itself is even better. Solid craftsmanship, architectural charm, and an exceptional circular floorplan set the tone for a one-of-a-kind living experience. From the moment you step into the gracious foyer, complete with a dramatic curved staircase, 505 Jackson radiates warmth, sophistication, and quality at every turn. The oversized living room features a beamed ceiling, handsome fireplace, and three walls of elegant windows. The spacious dining room sparkles with a statement chandelier, French doors, and lush views of the greenery outside. At the heart of the home, the updated kitchen delivers on every level: a massive island for gathering and entertaining, abundant cabinetry, quartz counters, stainless steel appliances, beverage cooler, pantry, and breakfast bar make this a true chef's kitchen. Open to both the kitchen and dining room, the showstopping family room is flooded with natural light from walls of windows. Adjacent to the breakfast area and with direct access to the backyard, this expansive space seamlessly connects indoor and outdoor living. A stylish powder room and functional mudroom complete the main level. Upstairs, four charming bedrooms each offer unique character. The spacious primary suite is a serene retreat with backyard views, while the northwest bedroom delights with a whimsical play area and sunny painted ceiling. The southeast bedroom boasts a cathedral ceiling with treetop views, and the fourth bedroom provides a quaint and cozy haven. The finished basement offers versatile living space for all ages - complete with a bonus room ideal for a playroom, office, or guest area, plus a wet bar, laundry zone, and ample storage. (It's also plumbed for a future bathroom.) Enjoy quintessential North Shore living near Downtown Glencoe, Hubbard Woods, the Weinberg Recreation Center, and award-winning New Trier schools. The roomy one-car garage and extensive behind-the-scenes improvements - including all-new electrical, a 2019 roof, and a $20K drain tile + vapor barrier system - make this home as solid as it is beautiful. Please note: All externally mounted and outdoor speakers are excluded from the sale, along with the mounted primary bedroom headboard. Fireplaces, chimneys, and windows are sold as is.