Welcome to this distinctive octagon bungalow where timeless character meets thoughtful modern updates creating a home that offers the space, comfort, and versatility for today's lifestyle demands. The original warmth of the property shines through the beautifully preserved stained glass front windows that allow natural light to fill its generously sized living room. Hardwood floors and a widened entryway from the living room, lead you to the formal dining room which offers a welcoming space for everyday meals, and special celebrations. The custom-designed kitchen is both stylish and functional, featuring stainless steel appliances, subway tiles, quartz countertops, a ceramic double sink, rich and abundant cabinetry, a built-in desk, and an island with dedicated space for bar stool seating-perfect for everyday living and entertaining. The main level bedrooms feature original hardwood floors, and nestled in between is an updated, full bathroom. On the second level you will appreciate the generously sized bedrooms with tasteful built-ins and an updated full bathroom. In the finished basement you will find two additional bedrooms, a family room, a full bathroom, a laundry space and the possibility of an area for a home gym or more storage. The backyard offers the perfect setting for your outdoor needs with plenty of space on the deck and in the yard. The dedicated garden area with retaining wall awaits your plantings of choice. This home's layout offers flexibility for multi-generational living, guests, or home office needs, with its three levels of living and is located right in the middle of Portage Park and Jefferson Park, allowing you quick access to the best each neighborhood has to offer. Proudly cared for and meticulously maintained, this home underwent an extensive renovation in 2016 with ongoing investments ensuring its condition remains impeccable over the years. - 2016 Renovations - Addition of Central Air, new HVAC and ductwork - providing the best of both heating worlds with boiler/radiator warmth and central air comfort (non-zoned). New hardwood floors on second level, and main level living room, dining room, and kitchen. New drywall and insulation on the main level and in the basement. Fully renovated all three bathrooms. New kitchen. Widened entryways - main level to dining room, and to kitchen. New second floor staircase. Restored radiators. Basement: family room with ceramic tile floor, full bathroom, added two bedrooms, and a dedicated work out or office space just outside of the newly added bathroom. New laundry sinks & washer/dryer. Additional improvements that followed: (2017) New deck. (2020) New concrete sidewalk east side of property, plus garage floor. (2021) Gutter & soffit fascia system w/leaf guard. (2021) Custom window treatments throughout the home that add a touch of sophistication and privacy. (2022) New windows *excl front & kitchen*, new screen doors front & back. (2024) Professional catch basin cleaning, air duct maintenance, and new stove. (2025) New washer, fresh paint, stained deck. This is a home where pride of ownership shows in every detail, ready to welcome its next chapter.