This multigenerational compound offers nearly an acre of private South Austin living, tucked away at the end of a quiet, dead-end street beneath a heritage red oak. The front home is an original 3-bedroom, 2-bath Mid-Century Modern rambler, beautifully restored and rich with character, warmth, and thoughtful updates throughout. A circular drive welcomes you under a red oak canopy, leading to a light-filled space that feels enchanting from the moment you arrive. A crisp and thorough make-ready has perfected every detail, ensuring the home is elevated, functional, and move-in ready. The property backs to Wayside Academy Charter Elementary and is within walking distance of Cunningham Elementary and Berkeley Methodist Church & Preschool, offering unmatched convenience near Garrison Park & Pool, local favorites along Manchaca Road, and quick access to downtown. The second home is a fully ADA-compliant 2-bedroom. A 2.5-bath guest house features a spacious kitchen, soaring ceilings, and covered decks overlooking the lush backyard. Both the primary suite and guest house open onto patios with tranquil koi pond views creating a private retreat perfect for morning coffee or evening wine. Enjoy a sparkling pool and spa, built-in bar, pergola, and fire pit — the ultimate setting for relaxed South Austin living. A rainwater retention system supports the in-ground sprinklers, raised garden beds, and pool which is ideal for eco-friendly gardening and water management. Additional highlights include an outdoor shower, three covered garage spaces, and a detached carriage house with a living area, bedroom, and bath. Lovingly maintained and pre-inspected with updates completed prior to listing. Just 15 minutes or less to downtown Austin and 15 minutes to Austin-Bergstrom International Airport, this rare South Austin unicorn offers versatility, privacy, and undeniable charm.