Sleepy Hollow Real Estate

Welcome to Sleepy Hollow, a serene and picturesque subdivision nestled in the heart of Orinda, California. Known for its enchanting landscapes and a strong sense of community, Sleepy Hollow offers a unique blend of suburban tranquility and easy access to urban amenities.

As you meander through the tree-lined streets, you'll be captivated by the charm of the homes that grace this neighborhood. Each residence boasts its own character, with beautifully landscaped yards and stunning views of the surrounding hills. The area is renowned for its spacious lots, providing ample room for families to grow and thrive.

Sleepy Hollow is more than just a place to live; it's a lifestyle. The community prides itself on its friendly atmosphere, where neighbors become friends and families come together for seasonal events and gatherings. With top-rated schools nearby, it's an ideal location for families seeking an enriching environment for their children.

Outdoor enthusiasts will appreciate the proximity to nature, as Sleepy Hollow is just a stone’s throw away from hiking trails, parks, and the scenic beauty of the East Bay Regional Parks. Whether you're hiking the trails or enjoying a picnic at one of the local parks, the natural beauty of the area is sure to inspire.

Conveniently located, Sleepy Hollow offers easy access to major highways, making it a breeze to commute to nearby cities or explore the vibrant culture of the Bay Area. With its blend of charm, community spirit, and natural beauty, Sleepy Hollow is truly a hidden gem in Contra Costa County. Come discover your dream home in this idyllic neighborhood today!

Newest Listings in Sleepy Hollow

$1,490,000

4 Beds ⋅ 2 Baths ⋅ 41142914 MLS

45 Sleepy Hollow Lane is perched on a grand 0.58-acre lot in the highly sought-after Sleepy Hollow neighborhood. This spacious 4-bedroom, 2-bathroom home offers 1,723 square feet of serene living space in one of the area's most desirable communities. Enjoy the birds singing in the trees and gardens on perfect sunny mornings, as you join with families walking children down the street to the top-rated, and idyllic, Sleepy Hollow Elementary. Less than 10 minutes to restaurants, entertainment, and shopping in downtown Orinda and BART (to San Francisco in 20 minutes, Oakland 15, Walnut Creek 10), but blissfully quiet and away from the urban hubbub. This home combines convenience, character, and timeless appeal. Inside, you'll find beautiful hardwood flooring throughout, recessed lighting, and an inviting floor plan filled with natural light. The well-appointed cooks kitchen is designed for both everyday living and entertaining, featuring a Viking 6 burner gas cooktop, double electric ovens, skylights, and view up into the large back yard. There is a working real brick, wood burning, fireplace in the Great Room and built-in charcoal barbecue on a large covered entertainment deck and side yard situated perfectly for social gatherings. One of the home's most unique surprises is a hidden wine cellar/tasting room! (an additional ~200 sq/ft+) A rare feature that adds charm and conversation-worthy character. Step outside to enjoy the expansive side and backyard, pesticide free for over two decades, where over 15 different mature fruit trees and organic irrigated raised beds create a peaceful setting with ample space for playing, gardening, entertaining, or simply relaxing.

45 Sleepy Hollow Ln, Orinda

Listing courtesy of Matthew Castillo from Keller Williams Realty. 925-200-9423

$2,495,000

5 Beds ⋅ 4 Baths ⋅ 41142231 MLS

Enjoy unparalleled privacy and spectacular views from this beautifully maintained and spacious Sleepy Hollow Mediterranean. Incredible Chef’s kitchen with luxury finishes including a show-stopping, cobalt blue, Viking Gas Range, Miele warming drawer, Wolf Microwave, Subzero fridge, Bosch dishwasher, and an expansive center island. Five large bedrooms and four full bathrooms. Custom built-ins featured in living room, guest bedroom/office w/built-in Murphy Bed, primary bedroom, and downstairs bonus room. Enjoy serene indoor/outdoor living and entertaining from the expansive decks w/spa, while being sheltered by majestic oaks and surrounded by mature, low-maintenance landscaping and Bistro lighting. Lovely garden areas with built-in BBQ. Bonus work/Flex space in the converted garage with Split-system climate control system. Buyers will also appreciate the many Smart Home features including a Google Nest Security camera system; there is also a built-in Tesla charger on side of garage. Highly sought-after location near Sleepy Hollow Elementary, Orinda Country Club, Sleepy Hollow Swim and Tennis. Approximately 2 miles to Orinda Village, BART, Highway 24. Top-rated Orinda & Acalanes district schools.

60 Tarry Ln, Orinda

Listing courtesy of Glenn Beaubelle from Compass. 925-200-5011

$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

$3,395,000

4 Beds ⋅ 3 Baths ⋅ 41139237 MLS

Custom designed by renowned Bay Area architects EnvelopeAD and completed in 2009, this striking contemporary residence offers 4 bedrooms, 3 baths, and approximately 3,907 square feet of living space on a private .52-acre lot in Orinda’s coveted Sleepy Hollow neighborhood. Thoughtfully positioned to capture beautiful ridgeline views and blend seamlessly with its natural surroundings, the home offers a rare combination of architectural sophistication, exceptional construction, and everyday comfort. The open, light-filled floor plan features dramatic walls of glass, soaring ceilings, and seamless indoor-outdoor living. Clean lines and warm modern finishes create spaces that feel both elegant and inviting, while the flexible layout provides ideal separation between gathering spaces and private retreats. A gated driveway and detached two-car garage provide privacy, convenience, and ample off-street parking. Built with an emphasis on quality and longevity, the home incorporates Class A fire-rated Italian siding by Abet, radiant heat, extensive copper plumbing, laminated glass windows and doors, interior fire sprinklers, built-in speakers, and high-end aluminum sliding doors. Substantial engineering, including approximately 70 piers anchored to bedrock, reflects the thoughtful planning and craftsmanship behind this exceptional residence. Located just minutes from Sleepy Hollow Swim and Tennis Club, award-winning Sleepy Hollow Elementary School, downtown Orinda, BART, Highway 24, and miles of scenic trails, 2 Crane Court offers a rare opportunity to enjoy contemporary architecture in one of Orinda’s most desirable neighborhoods. A truly distinctive custom home where design, quality, and setting come together beautifully.

2 Crane Ct, Orinda

Listing courtesy of Ann Sharf from Village Associates Real Estate. 925-200-0222

$2,499,000

4 Beds ⋅ 3 Baths ⋅ 41138118 MLS

Luxury Oasis in Orinda’s exclusive Sandhill enclave of Sleepy Hollow, this remodeled single-level Mid Century Modern retreat blends privacy, luxury, and seamless indoor/outdoor living with sweeping views, dramatic floor-to-ceiling windows, and nine skylights that bathe the home in warm natural light. The chef is never left out of the action with this open floor which includes a gourmet kitchen featuring a Sub-Zero refrigerator, 6-burner Wolf range, quartz countertops, and an oversized island designed for entertaining. Spa-inspired bathrooms include programmable radiant heated floors with Phylrich and Grohe fixtures, while a 7-zone HVAC mini split system provides personalized comfort throughout. The manicured backyard offers a true private haven with an outdoor BBQ, firepit, and peaceful spaces to relax, entertain, with pastoral views as if from an eagle's nest. Close to the Sleepy Hollow Swim and Tennis club, scenic trails, downtown Orinda, BART, and award-winning Orinda schools. Experience life in one of Orinda’s most coveted neighborhoods, where privacy, beauty, and luxury living come together.

233 Melody Ln, Orinda

Listing courtesy of Vlatka Bathgate from Coldwell Banker. 925-597-1573

$2,499,000

5 Beds ⋅ 5 Baths ⋅ 41136328 MLS

Improved price! Nestled on a peaceful cul-de-sac in Orinda's coveted Sleepy Hollow neighborhood, this beautifully remodeled residence offers an exceptional combination of modern design, flexible living spaces, and a serene natural setting. Featuring 5 bedrooms, 4.5 bathrooms, approximately 2,741± sq. ft. of living space, and situated on a generous .55-acre lot, the home is thoughtfully designed with dramatic walls of glass that blur the lines between indoor and outdoor living while filling the home with abundant natural light. The open-concept floor plan showcases engineered hardwood floors throughout and seamlessly connects the main living spaces to an expansive terrace—perfect for al fresco dining, entertaining, or simply relaxing while overlooking the peaceful surroundings. The versatile lower level features three secondary bedrooms and a spacious second family room ideal as a media room, playroom, teen retreat, or guest lounge. Outside, a level yard area near the upper driveway offers space for a play area, garden, or your own outdoor vision, while the remainder of the property is surrounded by mature trees and scenic natural beauty that enhance the home's sense of privacy and tranquility. Ample off-street parking complements the attached two-car garage, providing convenience for family and guests alike. Ideally located within walking distance of the popular Sleepy Hollow Swim & Tennis Club and just minutes from top-rated K-12 schools, downtown Orinda, BART, freeway access, and the iconic Orinda Theatre, this turnkey home delivers the perfect blend of privacy, convenience, and the coveted Sleepy Hollow lifestyle.

16 Sunnyside Ct, Orinda

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

$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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