Sleepy Hollow Homes with Contemporary Style

Welcome to Sleepy Hollow, a picturesque subdivision nestled in the heart of Orinda, California, within the stunning Contra Costa County. This charming community is renowned for its serene ambiance, lush landscapes, and welcoming neighbors, making it an ideal place for families and individuals seeking a peaceful retreat from the hustle and bustle of city life.

Sleepy Hollow is characterized by its contemporary-style homes that blend modern aesthetics with comfort and functionality. These residences boast sleek lines, open floor plans, and an abundance of natural light, creating an inviting atmosphere that is perfect for both relaxing and entertaining. Many of the homes feature expansive windows that frame breathtaking views of the surrounding hills and valleys, allowing residents to immerse themselves in the beauty of nature right from their living rooms.

This subdivision is not only a haven for contemporary architecture enthusiasts but also a community that values outdoor living. With nearby parks, hiking trails, and recreational facilities, residents can easily enjoy an active lifestyle while being surrounded by the stunning landscapes of Orinda. The friendly neighborhood vibe fosters a sense of belonging, where families can thrive and create lasting memories.

In addition to its beautiful homes and natural surroundings, Sleepy Hollow offers convenient access to top-rated schools, vibrant shopping districts, and a variety of dining options. Whether you’re looking for a cozy family home or a stylish retreat, Sleepy Hollow in Orinda is a place where contemporary living meets community spirit, making it a truly desirable destination in California’s Contra Costa County. Come discover the charm of Sleepy Hollow and find your dream home today!

Newest Sleepy Hollow Homes with Contemporary Style

$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

$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

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

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