Sleepy Hollow Real Estate

Welcome to Sleepy Hollow, a hidden gem nestled in the picturesque hills of Orinda, California, within the heart of Contra Costa County. This charming subdivision is a perfect blend of serene suburban living and vibrant community spirit, making it an ideal place for families, professionals, and retirees alike.

Sleepy Hollow is renowned for its lush landscapes, tree-lined streets, and stunning views of the surrounding hills. Here, residents enjoy a tranquil lifestyle, with easy access to nature trails and parks that invite outdoor enthusiasts to explore the beauty of the East Bay. The community is characterized by its spacious homes, many of which feature unique architectural designs and expansive yards, offering ample space for gardening, play, and relaxation.

Education is a cornerstone of the Sleepy Hollow community, with highly-rated schools nearby, ensuring that children receive a top-notch education. The local community is actively involved in various events and activities, fostering a strong sense of belonging and camaraderie among neighbors.

Conveniently located just a short drive from downtown Orinda, residents can easily access shopping, dining, and cultural attractions. Commuters appreciate the proximity to major highways and BART stations, providing seamless connections to San Francisco and beyond.

Whether you’re looking to settle down in a peaceful environment or seeking a vibrant community to call home, Sleepy Hollow offers the perfect blend of comfort, convenience, and charm. Discover the allure of this enchanting subdivision and envision your future in this idyllic setting!

Newest Listings in Sleepy Hollow

$2,395,000

5 Beds ⋅ 5 Baths ⋅ 41148080 MLS

A fresh opportunity and one of Orinda’s best values in the coveted Sleepy Hollow neighborhood! Set on a peaceful cul-de-sac and surrounded by mature trees and natural beauty, this beautifully remodeled 5-bedroom, 4.5-bath residence offers approximately 2,741± sq. ft. of thoughtfully designed living space on a generous .55-acre lot. Dramatic walls of glass fill the home with natural light, frame the serene surroundings, and create a seamless connection between indoors and out. The open-concept main living spaces feature engineered hardwood floors and an effortless flow ideal for both everyday living and entertaining. Step from the living area onto the expansive terrace—an inviting extension of the home for al fresco dinners, morning coffee, entertaining friends, or simply unwinding while taking in the peaceful setting. The beautifully updated kitchen connects naturally to the surrounding living spaces, creating a warm and welcoming heart of the home. The flexible floor plan provides excellent separation of space. The lower level features three secondary bedrooms along with a spacious second family room—perfect for a media room, playroom, teen retreat, home office, or additional gathering space. With 5 bedrooms and 4.5 baths, there is room to comfortably accommodate family, guests, work-from-home needs, and changing lifestyles. Outdoors, a level yard area near the upper driveway provides space for play, gardening, or creating your own outdoor retreat. The remainder of the property embraces the natural contours of the .55-acre setting, with mature landscaping and trees contributing to the home's wonderful sense of privacy and tranquility. Ample off-street parking complements the attached 2-car garage. Enjoy the sought-after Sleepy Hollow lifestyle with the popular Sleepy Hollow Swim & Tennis Club within walking distance and Sleepy Hollow Elementary nearby. Downtown Orinda’s shopping and dining, BART, freeway access, and the iconic Orinda Theatre are all just minutes away. Beautifully remodeled, move-in ready, and surrounded by nature—an exceptional opportunity to call one of Orinda’s most desirable neighborhoods home.

16 Sunnyside Ct, Orinda

Listing courtesy of Alex Villasenor from Coldwell Banker. 925-351-4949

$4,895,000

6 Beds ⋅ 6 Baths ⋅ 41141240 MLS

Once in a while, a home comes along that genuinely stops you. 240 Tappan Lane is that home. A long cobblestone drive winds beneath a canopy of Valley oaks before this stunning 6,800 sq ft contemporary comes into view. Set on 4.63 private acres above Briones Reservoir, the architecture is striking inside and out, cedar and steel exterior, glass and light throughout. The entry sets the tone immediately with floor to ceiling windows framing the reservoir through the oaks, and Porcelanosa porcelain tile underfoot. To the left, the living room opens up with warm oak floors, an exposed cedar beam ceiling, and walls of glass that keep that view front and center. The heart of the home is the great room, where a full glass roof and floor to ceiling sliding walls open the living space directly to the pool terrace and the oaks beyond. The kitchen is thoughtfully designed with dark cabinetry, granite counters, and a gas cooktop island that looks out over the living area without being separated from it. Two bedrooms on the main floor including a primary suite keep daily living entirely on one level. A second primary suite upstairs is perfect for guests or family. Six bedrooms and six and a half baths in total, finished with real care throughout, including a spa shower tiled in graphite porcelain. The home theater is its own world, lined with framed vintage film posters and purpose built for movie nights that actually matter. Outside, a sleek pool sits within terraced concrete gardens surrounded by mature trees, with the reservoir and rolling hills as a backdrop. A four car garage and expansive motor court complete the picture. Minutes to top rated schools and downtown Orinda.

240 Tappan Ln, Orinda

Listing courtesy of Shannon Conner from Village Associates Real Estate. 925-980-3829

$499,000

41121819 MLS

Rare offering in secluded Sleepy Hollow, -quiet cul-de-sac location with private driveway, substantially sunny exposure, yet also verdant views. Great privacy, large flat pad parking/garage area for entry and living level. Orinda SB-9 approved split, with possibly NO discretionary approvals needed. No cramped feel here! Walk to Sleepy Hollow Elementary and Swim & Tennis. Value-added in very favorable work-product of -Geotechnical soils reconnaissance, survey, topography, arborist report. There is no better value in this category! Secure this site for your forever home. All services available at street. -Please, before walking onto the site -text day/time to show & go! Seller may carry 1st deed of trust. 'Walk-around' video https://vimeo.com/1095701543?share=copy

13 St. James Ct., Orinda

Listing courtesy of Gerry Bakalian from Gerry Bakalian, Broker. 925-262-3333

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