Welcome to 200 Deer Hollow Road, a timeless single-family home sited on a gracious 17,100sf lot (per tax records)in the treasured Sleepy Hollow neighborhood. Owned by the same family for almost four decades, this cherished property was designed for privacy and to capture the natural beauty of its surroundings. A short flight of stairs leads up to the front entry and welcomes you into the generous living space spanning 3197sf (per tax records). The open-concept floor plan is flooded with abundant light and walls of windows that grace the Living and Dining rooms. The tall, natural wood cathedral ceilings exude character and warmth. A built-in window bench and cozy wood burning fireplace complete the space. The open-concept kitchen is the heart of the home featuring an island and breakfast bar with butcher block countertops. A professional Viking range and built-in wall oven ensure the home is suited for easy entertaining. The adjacent formal dining room offers custom built-in cabinetry and access to an outdoor patio. The Great Room provides an additional living area with a fireplace and French doors leading into the backyard, where a sparkling pool awaits along with a separate hot tub. A generous Primary Suite is also located on this floor with a walk-in closet, private terrace and light-filled en-suite bath. The remaining three bedrooms are in a separate wing with a conveniently located laundry closet and shared bath. Two of the three bedrooms have playful lofted areas for flexible sleeping or storage space. The lower level has its own exterior entrance, and features a media room with full kitchen, an office or 5th bedroom with bath offering an exceptional option as a potential Inlaw or AuPair space. The 2-car attached garage offers a second washer / dryer, with guest parking in the driveway and an oversized detached workshop. Located near the desirable Sleepy Hollow Community Clubhouse, hiking and biking trails, San Domenico School and the charming towns of Fairfax and San Anselmo - 200 Deer Hollow is a true legacy property ready to welcome its next chapter.