Welcome to 111 Deer Hollow Road, a rare opportunity in the highly coveted community of Sleepy Hollow. Set on nearly one acre along one of the neighborhood's most desirable streets, this exceptional property blends timeless character with thoughtful modern upgrades, creating an ideal retreat for today's lifestyle. The expansive 3,856 square foot main residence offers five bedrooms and four bathrooms, while a separate 300 square foot studio above the detached carport provides additional flexibility with its own full bathroom is perfect for guests, a home office, fitness space, or creative studio. Originally built in 1950 and updated over the years, the home features oak flooring throughout the main living areas, dual-pane windows, updated bathrooms with quartz countertops and sleek tile shower surrounds. The home also highlights to grand entertaining spaces with fireplaces in each and tons of windows to maximize natural light. Additional upgrades include updated electrical panels, a Navien tankless water heater, and a new roof with gutter guards installed in 2021. French doors in the living room open to the pool patio, creating seamless indoor-outdoor living. Designed for both everyday comfort and entertaining, the kitchen offers a breakfast nook, two sink areas, a combination of both gas and electric range tops, and a sliding door that leads out to an upgraded composite deck overlooking the western hills and swaying palm trees. The resort-inspired yard showcases a sparkling pool and spa surrounded by mature landscaping, providing a private setting for relaxation and gatherings year-round. The expansive parcel is enhanced by a long paved driveway with abundant parking, a detached carport equipped with a 220-volt outlet ready for EV charging, and three separate basement spaces offering endless possibilities for wine storage, game rooms, workshops, or additional flex storage space. Ideally situated just moments from the Sleepy Hollow Community Center, world-class hiking and biking trails, and the vibrant amenities of both San Anselmo and Fairfax, 111 Deer Hollow Road offers the perfect combination of prestige, privacy, recreation, and convenience. This is Sleepy Hollow living at its finest.