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.

Built in 1906, this timeless Craftsman residence captures the elegance, warmth, and craftsmanship of a true turn-of-the-century San Rafael classic. Perched in the hills above downtown on nearly a quarter acre, the property is perfectly positioned to take in sweeping bay views, glimpses of the Richmond-San Rafael Bridge, and abundant natural sunlight throughout its many outdoor spaces. Rich in original character, the home showcases elegant wood moldings, beautifully maintained hardwood floors, custom built-ins, and the enduring quality of old-growth redwood construction. Thoughtful upgrades, including an improved foundation and owned solar, blend modern functionality with historic charm. The spacious and inviting floor plan includes a formal dining room, gracious living room, kitchen with expansive pantry and historic built-in cabinetry. Three generously sized bedrooms with a bonus flex space family room upstairs as well. The primary suite offers a true retreat, featuring soaring vaulted ceilings, multiple skylights, dual walk-in closet spaces, and an en-suite bath with additional closet storage. Distinctive details such as a custom fireplace surround, expanded foyer and entryway, and the remarkable scale of every room create an atmosphere that feels both grand and welcoming. A massive lower-level unfinished basement bonus space offers exceptional flexibility for creative, recreational, or future expansion possibilities or possible ADU. Outside, multiple entertaining areas invite gatherings, gardening, and relaxation among mature fruit trees and sun-drenched terraces. A large flat western portion of the property currently serves as a parking pad but offers a variety of potential future uses. Mt. Tam also beckons through the Oak tree on the western side of the property. Throughout the home and grounds, a rare sense of spaciousness and comfort is ever-present, making this one-of-a-kind property a truly special place to call home.

Located on one of Bret Harte's most desirable streets, this expanded turn-key home offers a level of space and modern comfort rarely seen in the area. Following a comprehensive renovation completed in 2022, this home consists of three bedrooms, three and a half bathrooms and 2,012 square feet. Numerous upgrades include dual pane windows, recessed LED lighting, an upgraded electrical panel and composite decking. The chef-inspired kitchen is a showstopper, featuring abundant custom cabinetry, sleek quartz countertops, and premium stainless steel appliances from Bosch, Kitchen Aid and Bertazzoni. The expansive breakfast bar serves as a natural gathering point, flowing seamlessly into the dining and family roomsperfect for modern living and effortless entertaining. With a backyard pool and ample deck space which includes an area for dining and lounging, the property fits the Marin County lifestyle. French doors in the family room provide a clear connection to the backyard, completing the seamless indoor-outdoor flow that begins in the kitchen. Ideally located just around the corner from the local-favorite Bret Harte Park, this residence combines quality craftsmanship with the convenience of a sought-after San Rafael location. Conveniently located a short distance to downtown San Rafael, the property borders Greenbrae and provides easy access to Highway 101 for commuters. This property really does have it all!