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Nestled on the 14th fairway of the acclaimed Cupp Course, this beautifully appointed 5-bedroom, 4-bathroom brick estate offers a rare blend of timeless sophistication and resort-style living within the sought after gated community of Woodside. A sunlit foyer welcomes you into a formal dining room with views of the manicured front lawn, while the elegant living room—highlighted by stunning Hitchcock ceilings—serves as a graceful gathering space overlooking the backyard sanctuary. At the heart of the home, the chef's kitchen is both stylish and functional, featuring gleaming granite countertops, stainless steel appliances, a gas range, statement backsplash, and a central island. A bright breakfast nook flows seamlessly into a spacious secondary living area complete with a wet bar and ice maker—ideal for entertaining. The main-level primary suite is a true retreat, offering an expansive layout, spa inspired en suite with dual vanities, a makeup station, oversized garden tub, separate tile shower, and a generous walk-in closet. Two additional bedrooms on the main level share a well-appointed Jack-and-Jill bathroom, while upstairs, two more spacious bedrooms each offer large closets and abundant natural light. An enclosed sunroom overlooks the private backyard oasis, where you'll find a covered patio with TREX decking—perfect for alfresco dining or unwinding while enjoying the golf course views. The fenced, heated saltwater pool is a luxurious centerpiece to this serene outdoor escape. Immaculate hardwood flooring runs throughout, and the oversized 3-car garage with epoxy flooring adds both function and finish. Updated and meticulously maintained, this home provides exclusive access to over 14 miles of scenic trails, two private country clubs, championship golf, tennis, pickleball, swimming, and upscale dining—elevating every aspect of daily living.