Perfectly positioned in one of the Plateau's most established neighborhoods between Highlands and less than three miles to Cashiers, this private 4.45-acre estate presents a rare opportunity for a legacy family compound or multi-family vacation rental investment. Spectacular, unobstructed year-round views of Whiteside Mountain set the tone, with an oversized open deck designed to capture the iconic backdrop and cool mountain evenings. The main residence blends comfort and functionality. A covered breezeway flanks the attached 2 car garage and leads to a formal foyer and inviting living spaces with beautiful hardwood floors. The spacious kitchen offers an island, breakfast area, and access to a formal dining room overlooking the mountains. The living room features a brick fireplace with gas logs (can be wood-burning), while a cozy den or library with a wood stove provides a quiet retreat. A butler's pantry and powder room enhance the layout. Three en-suite bedrooms are located on the main level, including a generous primary suite with a cathedral ceiling, alcove sitting area, double vanities, walk-in tile shower, and its own washer and dryer, allowing for convenient one-level living. Flexibility defines this property. A two-bedroom, one-bath apartment with full kitchen, living room, and stack washer and dryer is located above a detached two-car garage, offering privacy from the main home. The lower level of the main home includes another fully equipped apartment accessible from the interior (with privacy door) or exterior entrance, complete with kitchen, washer and dryer, bedroom, bonus room, full bath, and a game room with a ping pong table. A separate studio apartment with exterior entrance features a kitchenette, full bath, and combined living/sleeping area-ideal for guests or rental income. Additional improvements include a detached two-car garage - perfect for a workshop- and a separate two-car carport with an additional storage room. A paved driveway with level entrance adds ease of access. Extensive storage, including a cedar closet, two Rinnai tankless water heaters, two central vacuum systems, three septic systems (no records on file with Jackson County), owned propane tanks, private well, and gas furnace support the estate's scale and versatility. With privacy, acreage, infrastructure, and one of the Plateau's most iconic views, this exceptional property offers rare potential as a generational retreat, income-producing investment, or both!