Welcome to this beautifully appointed 5bedroom, 4fullbath home offering exceptional space, timeless design, and modern technology, all perfectly situated on a quiet, low traffic cul-de-sac in sought after Jefferson Park. Designed for both comfort and style, this sun filled residence features a gorgeous open concept main floor highlighted by warm hardwood floors, a gas fireplace with custom mantel, designer lighting, and an open staircase that creates a seamless flow ideal for everyday living and entertaining. The chef's kitchen is truly the heart of the home, showcasing Bosch stainless steel appliances, classic shaker cabinetry, quartz countertops, a mosaic tile backsplash, and a generous center island with breakfast bar seating-perfect for casual meals or hosting gatherings. A main floor guest bedroom and full bath add flexibility, ideal for visitors, multigenerational living, or a home office. Upstairs, the sunny primary suite offers a private retreat with a spa bath featuring a frameless glass shower, designer tile, dual vanities, and a skylight. Two additional bedrooms, a full bath with tub, and a dedicated laundry room complete the upper level. The finished lower level elevates the home even further with impressive 13' ceiling heights, a spacious recreation room with wet bar and wine fridge, plus a fifth bedroom and full bath-perfect for guests, teens, or extended living. Outdoors, enjoy your own private patio, ideal for relaxing or entertaining. Additional highlights include a custom built, auto enthusiast's dream garage with epoxy flooring, abundant storage, and upgraded lighting. State-of-the-art security system, custom closets throughout, automatic shades in the family room, two zone HVAC with smart thermostats, and expandable smart Hue lighting in bedrooms and exterior-making this a truly move-in-ready, meticulously maintained home. Everyday convenience is unmatched, with nearby grocery stores, cafes, and locally loved restaurants along Foster and Lawrence Avenues, plus multiple neighborhood parks and green spaces just minutes away. The area is notably walkable for a residential setting and offers easy access to CTA bus routes and the Jefferson Park Transit Center, providing both Blue Line and Metra service for effortless commuting downtown or to O'Hare. Families will appreciate the home's close proximity to Beaubien Elementary School (PK8), located just a short walk away and widely regarded for its strong academics, active parent community, and welcoming neighborhood environment. High school students are typically served by William Howard Taft High School, rated in the upper tier of Chicago Public Schools A rare opportunity to own a thoughtfully designed, technology forward home offering exceptional space, natural light, privacy, and connectivity-this Jefferson Park gem truly checks every box. Check out the 3-D Tour and FACT SHEET (5033 WINONA AT A GLANCE) 1st showings 4/11/2026