Sleepy Hollow Homes with Contemporary Style

Welcome to Sleepy Hollow, a hidden gem nestled in the picturesque city of Orinda, California, within the enchanting Contra Costa County. This charming subdivision is renowned for its serene ambiance and stunning landscapes, making it a perfect retreat for those seeking a tranquil yet vibrant community.

Sleepy Hollow is characterized by its contemporary-style homes that seamlessly blend modern design with the natural beauty of the surrounding hills. Each residence boasts sleek lines, open floor plans, and large windows that invite abundant natural light, creating a warm and inviting atmosphere. From chic kitchens to spacious living areas, these homes are thoughtfully designed to cater to today’s lifestyle, perfect for both entertaining and cozy family gatherings.

The neighborhood itself is a haven for outdoor enthusiasts, with easy access to hiking trails, parks, and scenic views that showcase the best of Northern California’s landscapes. Families will appreciate the top-rated schools and the strong sense of community that Sleepy Hollow fosters. Neighbors often come together for local events, creating lasting friendships and a welcoming environment.

Living in Sleepy Hollow means enjoying the best of both worlds: a peaceful suburban lifestyle with quick access to the vibrant culture, dining, and shopping options that nearby Orinda has to offer. Whether you’re sipping coffee on your sunlit patio or exploring the lush surroundings, Sleepy Hollow offers a lifestyle that is as charming as it is contemporary. Discover your dream home in this idyllic subdivision and embrace a life filled with beauty and connection.

Newest Sleepy Hollow Homes with Contemporary Style

$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

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