Sleepy Hollow Homes for Sale

Welcome to Sleepy Hollow, a picturesque subdivision nestled in the heart of Orinda, California, within the stunning Contra Costa County. Known for its serene ambiance and breathtaking natural beauty, Sleepy Hollow is a hidden gem that offers a perfect blend of tranquility and convenience. This charming community is surrounded by lush greenery, rolling hills, and scenic views, making it an idyllic retreat for nature lovers and families alike.

Sleepy Hollow boasts a variety of homes for sale, each uniquely designed to cater to diverse lifestyles and preferences. From sprawling single-family residences to cozy cottages, the architectural styles reflect the area’s rich history and commitment to quality living. Many homes feature spacious yards, inviting outdoor spaces, and modern amenities, ensuring that every resident can enjoy the best of California living.

Living in Sleepy Hollow means you’re just a stone’s throw away from Orinda’s vibrant downtown, where you’ll find an array of boutique shops, delightful restaurants, and cultural attractions. Families will appreciate the highly-rated schools in the area, making it a fantastic place to raise children. Additionally, with easy access to major highways and public transportation, commuting to nearby cities like San Francisco and Berkeley is a breeze.

If you’re looking for a peaceful retreat with a strong sense of community, Sleepy Hollow is the perfect place to call home. Explore the available homes for sale and discover the charm and beauty that this enchanting subdivision has to offer. Your dream home awaits!

Newest Sleepy Hollow Homes for Sale

$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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