Located in Winter Park's historic Charmont neighborhood, at the end of brick-paved road that is lined with mature, canopying oak trees, lies this 5-bed, 5/2-bath haven overlooking desirable Lake Virginia. This home's impeccable exterior is complemented by its professionally landscaped lawn with blooming trees and exudes southern charm with its brick wraparound porch. As you enter the foyer, you will instantly notice the craftsmanship and expert care that went into the custom wainscoting and carpentry details throughout. To the right of the foyer, you will find the formal living room with two large French doors with direct access to the front porch that provide an abundance of natural light, an elegant fireplace and access to your very own private office with wall-to-wall built-in bookshelves. To the left of the entryway is a hall leading into the formal dining room and a generously sized butler's pantry connecting to the gourmet kitchen. The magazine-worthy kitchen offers sweeping views of Lake Virginia, stunning marble counter tops and backsplash, a porcelain farmhouse sink and top-of-the-line appliances, including a 6-burner Viking range oven with a classic-styled pot filler above. The kitchen also includes a cozy eat-in space and a wooden-top center island with a stainless-steel vegetable sink for added convenience when preparing your favorite recipes! The inviting family room is filled with natural light pouring through a set of three French doors providing direct access to the extended lanai and pool area. The second-floor master bedroom features an ample-sized reading area, a marble-faced gas fireplace, and two French doors leading onto a private wraparound balcony, affording outdoor lakeview lounging or morning coffee al-fresco year-round. The ensuite master bath showcases marble flooring, separate vanities, a marble-covered soaking tub with a charming, old-fashioned chrome faucet and handheld sprayer combo, and a luxurious standalone shower stall with a rain showerhead, handheld sprayer, two body sprayers and a gradient marble tile throughout. As you enter the oversized walk-in closet you will find a customized organization system and a door that is a convenient access point to the laundry room. The second floor also features two secondary bedrooms and hardwood flooring throughout. The lower-level is a show stopper and true delight providing endless possibilities with approx. 2,000 sq.ft. of living space, as it includes a large tv room with a powder bath, multiple flex rooms, a custom bunk room (with ensuite full bath) that has served as the perfect space for sleep overs, but also offers an opportunity to be converted into a home gym or theater. The lower-level currently offers a dark room and photo editing room that could be converted to fit a large array of purposes. The perfectly manicured outdoor living space includes a heated pool and spa flanked by two well-maintained grassy areas on each side. Improvements made include two newer A/Cs (2020 & 2017), added hardwood flooring to the 2nd floor and lower-level, and the lanai extension. Ideally located to enjoy scenic walks to Rollins College, Park Avenue, and local favorites such as East End Market, Foxtail Coffee, Black Bean Deli and more. Downtown Orlando is conveniently just under 5 miles away, providing a quick commute to area hospitals, and is just 30 minutes to MCO. Zoned for Audubon K-8 and Winter Park High School!