Welcome to 299 Woodside Circle SW, a versatile 4-level split offering outstanding layout, solid bones, and exceptional outdoor space in one of southwest Calgary?s most established, nature-rich neighbourhoods. Nestled on a quiet circle in Woodlands, this home puts you steps away from mature parks, local schools, and the endless pathway networks and natural beauty of Fish Creek Provincial Park. With quick access to the Canyon Meadows Golf and Country Club, shopping plazas, and the Stoney Trail / Anderson Road corridors, the location perfectly balances everyday convenience with a tranquil suburban feel. The bright main level welcomes you with hardwood flooring throughout the expansive living room and dining area, flowing seamlessly into a kitchen featuring the ideal bones and layout for your custom culinary dream space. Upstairs hosts two well-proportioned guest bedrooms that make wonderful kids' rooms, effortlessly housing all their toys, desks, and more, alongside a full 4-piece bathroom and a generous primary retreat that easily accommodates a king-sized bed and features its own private 2-piece ensuite. The third level is tailored for relaxation, boasting a cozy family room centered around a classic wood-burning fireplace, a versatile flex space that could easily be enclosed to create a 4th bedroom, and a second full bathroom featuring a convenient 3-piece setup with a full shower. Down on the 4th level, you will find extensive utility and storage space including easy access to a large crawlspace located right off the furnace room, alongside a flex area ready for your finishing touches, whether you envision a private home theatre, games area, or home gym. Outside, the large, private backyard has plenty of room to design your ideal patio retreat, plant a garden, and give kids and pets room to play. An oversized detached garage handles parking and hobby storage, complemented by a dedicated RV parking pad. Added peace of mind comes from roof shingles replaced in 2019 and Hot Water Tank in approx 2017. A solid home with immense potential in a premier South Calgary community!