Sleepy Hollow

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Sleepy Hollow

Discover Sleepy Hollow: A Serene Community in San Anselmo, California

Welcome to Sleepy Hollow, a charming and sought-after neighborhood nestled deep within the rolling hills of San Anselmo, California. This picturesque community offers a unique blend of tranquility, scenic beauty, and a rich history. As a seasoned real estate broker with an in-depth knowledge of the area, I'm excited to guide you through all that Sleepy Hollow has to offer. In this article, we'll explore the neighborhood's geographical location, delve into its history, highlight local amenities, outdoor activities, entertainment options, school information, and provide insights into the housing market. So, let's embark on a journey to discover the hidden charms of Sleepy Hollow.



Geographic Location

Sleepy Hollow is positioned deep within the rolling hills of San Anselmo, Marin County, making it an ideal place for those seeking a serene escape without sacrificing proximity to essential amenities. The neighborhood's unique topography is characterized by lush greenery, wooded areas, and scenic vistas, making it a nature lover's paradise.




The history of Sleepy Hollow is intertwined with the development of Marin County. Originally a part of Rancho Punta de Quentin, the land was divided into smaller parcels in the early 20th century. It was during this time that Sleepy Hollow began to take shape as a residential community. The neighborhood's name, Sleepy Hollow, conjures up images of peaceful, rural living, and it has certainly lived up to that reputation over the years.


In the mid-20th century, the community saw substantial growth and development, with the construction of single-family homes that have become iconic to the area. The community's commitment to preserving its natural beauty and tight-knit, friendly atmosphere has remained steadfast, making Sleepy Hollow a place where families and individuals find both solace and a sense of community.



Local Shopping

While Sleepy Hollow offers a retreat that is unique to the area, you're never too far from excellent shopping options. The charming town of San Anselmo, just a short drive away, is known for its delightful boutique stores, quaint shops, and a variety of dining options. Whether you're looking for unique gifts, gourmet food, or everyday essentials, San Anselmo has you covered. Additionally, residents have access to larger shopping centers in nearby towns like Fairfax and San Rafael, which feature popular retail chains and grocery stores.



Outdoor Activities

One of the standout features of Sleepy Hollow is its abundance of outdoor activities and recreational opportunities. The neighborhood is surrounded by pristine natural beauty, making it an excellent destination for nature enthusiasts. Residents can explore the various parks and open spaces in the area, such as the Terra Linda Sleepy Hollow Northern Divide preserve, which offers hiking trails and serene picnic spots.


Furthermore, Sleepy Hollow is part of the larger Marin County, known for its extensive trail system. Whether you're into hiking, biking, or simply enjoying a leisurely stroll, there are numerous trails to explore, each offering breathtaking views of the rolling hills and redwood forests.




While Sleepy Hollow is cherished for its tranquil ambiance, entertainment options are not far away. San Anselmo is home to a vibrant community,  a charming downtown, boutique stores, and community events that showcase the talents of Marin County residents. If you're in the mood for a night out, explore the diverse restaurant scene in San Anselmo, offering a variety of cuisines to please your palate. Additionally, the neighboring towns of San Rafael and Fairfax provide additional entertainment options, including movie theaters and live music venues.



School Information

Families in Sleepy Hollow have access to top-notch educational opportunities. The neighborhood is served by the Ross Valley School District, offering a range of public schools known for their strong academic programs. Some of the schools serving Sleepy Hollow include Wade Thomas Elementary and White Hill Middle School, both of which are highly regarded for their educational quality.


For families seeking private school options, San Anselmo is home to some prestigious institutions, such as San Domenico School, known for its rigorous curriculum and nurturing environment. Additionally, Marin Catholic High School in nearby Kentfield offers excellent high school education for the students in the area.



Housing Market

Sleepy Hollow's real estate market is as unique and appealing as the neighborhood itself. The housing stock primarily consists of single-family homes, each with its own distinct charm. The architectural styles in the area vary, ranging from mid-century modern to contemporary designs, and even some custom-built residences. With an emphasis on preserving the natural landscape and maintaining a sense of seclusion, you'll find that many homes in Sleepy Hollow are nestled among lush landscapes or situated on expansive lots, offering a blend of privacy and a connection to the outdoors.


The average home price in Sleepy Hollow reflects its desirability and the idyllic lifestyle it offers.  Home prices in Sleepy Hollow typically increase in values as you go deeper into the valley. It is not uncommon to find less expensive and smaller homes closer to Sir Francis Drake Blvd., homes from $1.2 million to $1.6 million. However, further up you get the lot sizes tend to increase along with the overall square footage of the homes, so very common to find homes anywhere from $2-4M.


Whether you're looking for a cozy cottage, a spacious family home, or a contemporary architectural masterpiece, Sleepy Hollow has a wide range of options to suit various tastes and preferences. The real estate market is competitive, and properties tend to sell relatively quickly, so it's advisable to work with an experienced real estate professional who understands the nuances of the San Anselmo market.




Sleepy Hollow in San Anselmo, California, is a beautiful community, offering the perfect blend of natural beauty, history, and modern convenience. Its unique geographical location, rich history, and proximity to excellent schools, shopping, outdoor activities, and entertainment make it an ideal place to call home. If you're looking to buy or sell a property in Sleepy Hollow, don't hesitate to reach out to me, your local real estate expert. I'm here to help you explore all that Sleepy Hollow has to offer and guide you through your real estate journey in this remarkable neighborhood. Contact me today to discover your dream home in Sleepy Hollow, San Anselmo.



Explore Other Neighborhoods of San Anselmo

Brookside  /  Calumet Sais, Madrone, Yolanda Station  /  Camino De Herrera, San Anselmo, Oak Springs Woodside  /  Crescent Road, Robson-Harrington, Oak  /  Ross Avenue  /  Sleepy Hollow  /  Sorich Park and Sequoia Park  /  Yolansdale  /  Winship Park

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I first strive to understand your unique situations, whether you are buying or selling. Through asking questions and attentively listening, I support and guide you in finding the best fit.

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