Sleepy Hollow Homes with Trees/Woods View

Welcome to Sleepy Hollow, a picturesque subdivision nestled in the heart of Orinda, California, within the beautiful Contra Costa County. This enchanting community is a hidden gem that perfectly blends the serenity of nature with the comforts of suburban living. Sleepy Hollow is characterized by its stunning homes that are surrounded by lush trees and scenic woodland views, making it a perfect retreat for those seeking tranquility and a connection with nature.

As you stroll through the charming streets of Sleepy Hollow, you’ll be captivated by the sight of stately homes that boast expansive windows, allowing for breathtaking views of the towering trees and serene landscapes that envelop the area. Many of these residences feature spacious decks and outdoor living spaces, perfect for enjoying the gentle California breeze while sipping your morning coffee or hosting evening gatherings with friends and family.

The community of Sleepy Hollow is not just about beautiful homes; it’s also about lifestyle. Residents here enjoy easy access to an array of outdoor activities, including hiking trails, parks, and recreational facilities that encourage an active lifestyle. The nearby Orinda Community Center and local farmers' markets provide opportunities for socializing and community engagement.

With its unique combination of natural beauty, charming architecture, and a welcoming community atmosphere, Sleepy Hollow is more than just a place to live—it’s a place to thrive. Discover your dream home in this idyllic subdivision and experience the magic of Sleepy Hollow for yourself!

Newest Sleepy Hollow Homes with Trees/Woods View

$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

$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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