WOODLANDS is an extraordinary 7-bedroom, 5-bathroom estate offering two distinct residences set on approximately 63 private acres of mature forest, scenic trails, and meticulously landscaped gardens. Perfectly positioned at the prestigious corner of Escarpment Sideroad and St. Andrews Road, surrounded by grand country estates and directly across from Paintbrush Golf Club, while just minutes to Devil's Pulpit Golf Association. The main residence is highlighted by a breathtaking 14-foot floor-to-ceiling great room and an elegant open-concept marble and onyx kitchen. A dramatic two-sided floor-to-ceiling fireplace beautifully separates the principal living and dining rooms, while expansive wraparound terraces provide seamless indoor-outdoor living from every principal space. Two luxurious primary suites each feature walk-in closets and spa-inspired 5-piece ensuites. The walk-out lower level is designed for exceptional entertaining, complete with a spacious family room, wine cellar, recreation area, mirrored fitness studio, two above-grade bedrooms, and a custom 10-person wet bar. The contemporary Pool House offers two additional bedrooms, dramatic floor-to-ceiling windows, a spacious 3-piece wet room, and stunning views over the infinity-edge pool and hot tub. Outdoor entertaining is equally impressive with an expansive dining terrace, championship tennis court, beautifully manicured gardens, woodland walking trails, and a tranquil fire pit setting surrounded by towering pines. Offering approximately 6,000 sq. ft. of total living space, WOODLANDS presents a truly exceptional private estate in one of Caledon's most coveted locations.