Welcome to a special place where comfort and enjoyment is woven into the fabric of this unique Dutch Colonial, nestled into the leafy hillside overlooking Hillsborough. With its gambrel roofs and multiple wings, the three story floor plan offers numerous spaces to entertain or retreat and recharge. Tucked behind a picket fence with a lush front lawn, the five-bedroom home with 4.5 baths was built in 1925 and has been lovingly maintained and substantially improved, while never losing its original charm.

Welcome to 371 Glendale Road, San Mateo.

Stepping into the foyer, the gleaming parquet floor, a grand staircase and a sun-filled space spreads out in all directions beckoning you further in. Off the entry is an expansive living room with wainscoting, a huge fireplace and a bank of windows. Beyond is a large sun-drenched library with French doors leading out to a treetop deck. Heading back along the main level, you’ll find two bedrooms, one with access to the outdoors, along with a full bath.  The flexibility of multiple spaces throughout the residence will suit all your work-from-home needs! 

A formal dining room with windows on two sides leads into a large gourmet kitchen with new quartz counters, backsplash, fixtures and an expansive central island. Create culinary delights with upscale stainless steel appliances recessed into custom cabinetry. A gently curving bay with four large windows and canyon views is the perfect spot for your morning coffee and breakfast. Guests and family will naturally congregate in this gorgeous welcoming space, completely open to a charming family room. An entertainment pantry with a sink, mini-fridge, and prep counter leads out to the back deck, perfect for dining al fresco! There’s also a convenient powder room with a corner sink. 

Primary sleeping quarters are found upstairs, including a delightful primary suite with a reading nook, sitting area, dressing room and an incredible walk-in closet. French doors lead into a huge showcase bathroom with vaulted ceiling, skylights, windows, a twin-sink marble vanity, glorious walk-in shower with a skylight, and a freestanding deep soaking tub. There’s even an alcove with a washer and dryer. Across the hall is a second large bedroom with a reading nook and two closets, plus a full bath. 

More options await on the lower level, with new wood floors, an abundance of natural light and views from a wall of french doors, and a giant entertainment room. On this level you’ll also find the fifth bedroom with a private, full bath with frameless shower, walk-in closet, and a wine cellar. French doors from both the bedroom and the entertainment area lead to an expansive trellis-covered deck, and access to the lower lawn. There is also easy access to the two-car garage with fantastic extra storage spaces.

Outdoor spaces play an integral role in the charm of this home, with multiple decks wrapping around the house. From the family room, enjoy the outdoor fireplace on cool nights, or prepare meals with an outdoor kitchen featuring both a gas grille and a smoker. There’s a beautiful overhead trellis on the lower level deck, with rustic stone walls and rolling scenic views overlooking Hillsborough. Steps lead down to an additional lawn with a play area. You’ll seldom discover a home like this, framed by wisteria, roses, daisies, tasteful shrubs and gracious shade trees. 

371 Glendale Road sits in the hills of San Mateo Park, above Hillsborough. The serene enclave with its canopies of trees is a wonderful place to walk and wander. You’re just a mile from historic downtown San Mateo with vibrant shopping and top eateries, parks, and more. Burlingame is just over a mile away, too! Convenient access to US-101, CA-92, and CalTrain means you can quickly and easily access anything you need.