Welcome to 919 S Oak Avenue! Sitting proudly on a corner lot on Historic Downtown Sanford's coveted Oak Avenue, this 4 bedroom, 3 bath with rare TWO CAR detached GARAGE offers the perfect blend of timeless elegance and contemporary convenience. As you step through the front gate, you'll be greeted by the wide and welcoming front porch - just one of three beautiful porches on this home - the second story porch allows you to soak in the rich history of the area from above, while a cozy side porch beckons for your morning coffee. Upon entering, notice the open and inviting layout of the first floor - a formal living room up front, formal dining room, family room, kitchen and large mudroom/utility room off of the kitchen, as well as one bedroom and one bathroom conveniently located downstairs, with potential to be a primary bedroom, guest room or home office. The well-appointed kitchen features a large pantry and shares an open layout with the family room, a cozy space to make memories. Upstairs, three bedrooms and 2 baths await, including the primary bedroom with en suite bathroom. The second upstairs bedroom features the most ADORABLE built in window seat/reading nook. This home boasts SO MUCH storage - very unusual in a home of this age! A door just off of the upstairs landing leads you to the upper porch, a place to relax in privacy and shade, taking in the beauty of Oak Avenue below. The oversized back deck, offers an incredible space for outdoor entertaining, grilling or simply basking in the Florida sun - ideal for hosting gatherings for weekend cookouts and parties in this private retreat. Sail shades provide shade and the outdoor cafe lights cast the perfect ambient light. The lovely backyard includes Pineapple plants, a native Florida herb garden and outdoor compost area. The oversized 2 car garage with openers includes loft storage space. Behind the garage is an asphalt parking area - perfect to store your toys of choice! Recent updates include foundation upgrades, (2) 2021 HVAC units, ROOF - 2020, custom-made doors/screen doors, smart thermostats, wood fence (2023) and transferrable termite bond for your peace of mind! This home's location is truly unparalleled, with Historic Downtown Sanford at your doorstep. Explore the vibrant local shops, lively events, restaurants, and cultural attractions that make this area so beloved. Don't miss this rare opportunity to own a piece of history with rare combination of the location + modern amenities you desire. Schedule your showing today!