Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1 acre lot. Exuding timeless charm with a subtle New England ambiance, this residence represents the best of historic Winter Park livingall within walking distance to Park Avenue. This stately 6 bedroom, 5.5 bathroom home offers 5,759 square feet of thoughtfully designed living space, plus an additional 1,859 square foot unfinished basement that spans the entire length of the home, offering endless possibilities for expansion or customization. Upon entry, you'll be welcomed by coffered ceilings in the spacious formal living room, rich dark oak floors, and one of the homes three gas fireplaces. This elegant yet inviting room overlooks the lush gardens, making it an ideal setting for both entertaining and quiet relaxation. Adjacent to the living room is a cozy, beautifully appointed den featuring another gas fireplace and natural jute flooringundoubtedly one of the most beloved spaces in the home. The kitchen is filled with natural light and includes a large casual dining area, a charming butlers pantry, and direct access to both the laundry roomcomplete with a full size refrigerator and half bathand the oversized 2 car garage. The formal dining room showcases lattice framed bay windows with views of the back garden and pool area, creating a warm and elegant space perfect for holiday dinners and family gatherings. The home features two primary bedroom suites on the main level, including one expansive L shaped suite with its own gas fireplace and views of the pool, gardens, and outdoor terrace. The primary bathroom includes a dressing area and marble finishes throughout. Upstairs, the south wing includes two generous bedrooms with a shared full bathroom, while the north winglocated above the kitchenoffers two additional bedrooms and a charming full bath. The expansive backyard is a private sanctuary, framed by majestic oak trees, bamboo, and thoughtfully designed gardens, with several inviting sitting areas for outdoor relaxation. An extra large swimming pool completes the settingperfect for warm Florida days or evening gatherings under the stars.