Sleepy Hollow is a leafy enclave on the northwest side of Orinda, where sun-warmed hillsides, winding lanes, and generous lots create a calm, everyday retreat. Architecture ranges from mid-century ranch homes to thoughtfully renewed contemporaries, often on quarter- to half-acre parcels. Mornings bring birdsong under heritage oaks; afternoons stretch into patio dinners and bike rides to nearby trailheads, reinforcing the easy indoor-outdoor rhythm that draws people here.
Families prize the neighborhood’s strong academic path. The walkable centerpiece, Sleepy Hollow Elementary School, feeds into Orinda Intermediate and on to Miramonte High School, a consistent top performer. Community spirit shows up at the member-run Sleepy Hollow Swim & Tennis Club, a summertime hub for swim meets, tennis drills, and neighborhood gatherings. For date nights and weekend matinees, the glowing marquee of the restored Orinda Theatre anchors downtown, along with casual cafes and weekly errands.
Commuters appreciate quick access to Highway 24 and BART; the Orinda station is a short drive, and the Caldecott Tunnel keeps regional commutes efficient. Everyday conveniences in Lafayette are minutes away, and county services are provided by Contra Costa County, while city programs—from parks to seasonal events—remain close at hand.
Whether you’re upsizing for more space or downsizing to simplify, Sleepy Hollow offers a polished, low-stress backdrop for daily life. If you’re considering a move, Agent Pronto can connect you with a top local real estate professional—whether you’re buying or selling.