Discover the best of community and convenience at 275 Virginia Drive! This charming, mid-century gem created treasured memories for the same owners since 1955. A perfect blend of vintage character with some fresh updates, this classic 4-bedroom, 2.5 bath ranch has been meticulously cared for and is move-in-ready, but could also present an ideal canvas for a designer’s brush. Situated on a quiet street in the golf cart district of downtown Winter Garden, this home has the benefit of being closely located to the vibrant downtown area where top-rated dining, trendy shops, and the weekly farmer’s market await. For even more recreation, the West Orange Trail is one block away for jogging and biking, or take a quick golf cart ride to appreciate the serenity of Lake Apopka. Beyond a front entrance showcasing the original owner’s beveled-glass artistry, natural light from a large picture window enhances the vintage hardwood floors and neutral colors flowing throughout the living room and secondary bedrooms. An efficient kitchen features a cozy breakfast nook adjacent to the combined great room and dining area; an ample, open space for entertainment and holiday gatherings with loved ones. The separate, primary bedroom is generous, boasting a private entrance and a full, tiled bath. The roof, HVAC, and some plumbing fixtures were replaced within the last few years and in August 2025, a new and upgraded electrical system was installed. Outside, a handy sprinkler-system helps keep the sunny front yard lush while the backyard is surrounded by mature trees and shrubbery, making it a perfect spot for little ones and four-legged friends to roam freely without worry, as well as cookouts, or just outdoor relaxation in the warm Florida weather. Creative folks will spend countless hours in the custom workshop situated on its own concrete slab, and complete with attic storage and window A/C. This shed could easily be insulated and upgraded to create a comfortable space for a hobby area, man cave or anything else to suit your needs! This charming home is brimming with nostalgia and is ready and waiting to be your new forever home. Don’t miss your chance to own a piece of Winter Garden history, schedule a private showing TODAY!!!