Experience the lifestyle you have dreamed about in South On Main - Downtown Woodstock's Premier Community. Welcome to an exceptional opportunity to live in the heart of Downtown Woodstock's most sought-after neighborhood-South On Main. Nestled on a premier lot, this beautifully crafted four-story luxury home offers refined living at every level, complete with 5 bedrooms, 4.5 baths, a private elevator, and designer upgrades throughout. Step inside and discover a home bathed in natural light, where expansive windows, plantation shutters and an ideal orientation make every room feel bright and inviting. The main level is thoughtfully designed for both gracious entertaining and comfortable everyday living, featuring a formal dining room with upgraded trim, a welcoming sitting/office room with custom French doors, and an open-concept living space with upgraded lighting and custom finishes. The beautiful family room features built-ins on either side of the fireplace. At the heart of it all lies the chef's kitchen-a true culinary masterpiece. Outfitted with custom cabinetry, quartz countertops, a Thermador dual-fuel convection oven, and a generous center island, this space is sure to inspire your inner gourmet. Step outside to enjoy dining on the deck or unwind with a drink on the covered porch-perfect for morning coffee or sunset cocktails. Upstairs, the primary suite is a private sanctuary, showcasing elegant wainscoting, a spa-inspired ensuite bath with a soaking tub, double vanity, and an oversized walk-in, custom closet. Two additional bedrooms share a stylish Jack & Jill bathroom, and the spacious laundry room with a barn door-complete with a sink-adds everyday ease. The top-level is your personal retreat in the sky, featuring a fourth bedroom, full bath, and a generous bonus living area that opens to a Sky Terrace with panoramic views of the community garden and surrounding neighborhood. The terrace level brings even more versatility with a home office or media room, plus a flex space perfect for a guest suite, 5th bedroom or workout space with its own full bath. Completing this luxurious home is a 3-car garage, mudroom, irrigation system, and fully fenced yard! And perhaps best of all? You're just a short stroll or golf cart ride away from Downtown Woodstock's award-winning restaurants, boutiques, breweries, parks, and community events. This is more than a home-it's a lifestyle. Don't miss your chance to own one of the most feature-rich properties in South On Main.