Sleepy Hollow

Welcome to Sleepy Hollow

A small, hillside village tucked along the outskirts of Dundee Township

Known as “one of the quietest places in the world,” Sleepy Hollow is a peaceful retreat away from the hustle and bustle of city life. This small, rural community is home to just over 4,000 residents and spans a total of two square miles. Residents enjoy a homey feel in their small village and take great pride in their community’s annual events. Despite the “sleepy” namesake, there are plenty of things to do in this wonderfully charming village.

Floyd T. Falese bought Sleepy Hollow Farm in 1953. Back then, it was regarded as a “parcel of the Dundee community,” and Falese did not want the land to become too “suburban” by grid lines and clustered businesses. His mission was to maintain the “farmland” atmosphere and build up the community with a few residential areas. He hired an architect who tactfully created winding roads, cul-de-sacs, and developments without ever cutting down a single tree. The promise to keep Sleepy Hollow as a peaceful retreat has remained to this day, and residents enjoy a slow, quiet life along the outskirts of Dundee Township.

Local Lifestyle

Young families and retirees looking for a reprieve from busy city life make their home in Sleepy Hollow. The neighborhood is lined with a mix of custom-built homes of the 1960s, and newly constructed homes can be found in The Bluffs, the newest subdivision in Sleepy Hollow. Residents of this tiny town are highly community-focused and put a lot of time into various ways to uplift the community and help others. Communal gardens and the “Giving Garden” are found throughout the neighborhood, with residents growing produce to donate to different organizations in Sleepy Hollow and beyond. For a quiet and charming reprieve from city life, Sleepy Hollow is the ultimate place to call home.

Dining, Entertainment, and Shopping

Part of Sleepy Hollow’s charm is that it’s strictly a residential community, meaning there aren’t many options within the small, two-mile neighborhood for dining and shopping. Residents make the short trip to the outskirts of Sleepy Hollow to East or West Dundee for dining and shopping options. However, Sleepy Hollow offers one incredible restaurant within village limits: Salsa Street Mexican Restaurant. This family-owned, authentic Mexican restaurant offers delicious Mexican cuisine with signature sauces and fresh ingredients. They have an extensive wine and spirit list (with the best tequilas) and feature large, outdoor patios with live music during the warmer months. They also rent their space for private events and offer fantastic catering options.

Things to Do

Sleepy Hollow Pool is the place to be during the summer months. Featuring diving boards, no-depth entries, dozens of picnic tables and shady areas, and a concession stand with one of the best menus in town, the Sleepy Hollow Pool is the perfect place to go for residents of all ages. Kick back and relax in a lounge chair by the water, or cool down in the deep end! Sabatino Park is known as the best destination for kite flying in Kane County, as the large, open space provides excellent opportunities to catch the wind. The 12-acre park also offers a baseball field, a pleasant lake for fishing, and a playground.

The annual Fourth of July Celebration is the community event of the year. Every resident comes out to celebrate their country and small village, and local residents help set up and tear down after the festivities. The celebration is a testament to the dedication and care of Sleepy Hollow residents – from the organizational effort to the packed schedule. The day commences with a Fishing Derby and a car show with dozens of food, beer, and wine options and ends with live music, a parade, and the announcement of the yearly raffle winners.  The Sleepy Hollow 4th of July Fireworks consistently rank in the Top 10 shows in the Chicagoland area.

The Legend of the Headless Horseman is alive and well every Halloween in the Hollow.  Even though the Legend didn’t originate here, the residents get together every year to bring the Legend to Life.  Chili cookoffs, costume contests and a bonfire conjure the spirit of the Headless Horseman who culminates the celebration by riding through the village.  Check out THIS ARTICLE in the Wall Street Journal about this unique annual event.


Sleepy Hollow is home to several excellent schools within the Dundee district. Some of them include:

Sleepy Hollow Elementary, a public school for grades K-5.

Dundee Middle School, a public school for grades 6-8.

Dundee-Crown High School, a public school for grades 9-12.

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