Seize a rare opportunity to own TWO distinct homes on a single lot, ideally situated in the heart of vibrant Downtown Woodstock! 8175 Main Street is a premier location, directly across from prestigious Adair Park, with its restaurants, shops and luxury flats. This dual-living property, perfect for multi-generational living, business, entertaining, or extended stay guests offers exceptional flexibility as well as investment opportunity. The primary residence, originally an historic home constructed in 1948, was masterfully reimagined by owner/designer and her team of architects in 2022 into a stunning residence which retains some of the original timeless charm and character, blended with modern luxury and cutting-edge upgrades. This property was uniquely curated to combine CHARM, LUXURY, CONVENIENCE, OUTDOOR LIVING and ENTERTAINING as its key components. The home boasts a chef's dream kitchen anchored by a breathtaking 12 foot island adorned with a gorgeous Brazilian Quartz, also featured in the backsplash and wet bar in the living area. Entertain effortlessly with a spacious oversized butler pantry, indoor wet bar, and flowing open floor plan. The living area off kitchen is centered around a cozy fire place and has three sets of french doors leading to the show-stopping outdoor oasis poolside. The custom designed pool features a tanning ledge and a unique swim ledge that curves along the water's edge. Outdoor living takes center stage with an outdoor covered kitchen featuring a smoker, oversized gas grill, Blackstone griddle, gourmet pizza oven , dishwasher, two beverage refrigerators and an ice machine, all surrounding a large entertainment area with a cozy outdoor fireplace. There is also a "DJ Balcony" perched above the entertaining space, ready for the party! The main home has wide corridors leading to each of the three bedrooms, perfectly positioned each with its own 'wing" for peace and privacy. A beautifully appointed second residence is located directly behind the poolside oasis, featuring three private bedrooms, one on the main level and two on the secondary level, a split bedroom plan for privacy. The main level features an expansive 6-car garage, which can also be used as indoor event space, an EV charging station, a set up for a second laundry, a dog shower, a private sitting porch ,a custom putting green, and a large detached tool/equipment shed. The second story comprises an open floorplan, kitchenette, dining area, living room, two bedrooms ( one with a balcony overlooking pool with views of downtown, currently used as office space), a full bath and generous closet space throughout. Lovely landscaping, outdoor lighting, a large yard for PETS, a commercial grade security system with AV closet, and a charming front sitting porch overlooking downtown add to the charm and appeal of this special downtown property. Experience all the perks of downtown Woodstock living as you walk to restaurants, spas, shopping, the summer concerts in the park, and outdoor events. Experience life without the hassles and restrictions of HOAs and management fees! This extraordinary property is a rare find--two residences, thoughtfully designed for comfort, entertaining and luxurious everyday living in one of Woodstock's most desirable locations.