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

$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

$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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