Sleepy Hollow is a quiet community several miles from the Fox River
The Village of Sleepy Hollow, in the Fox River Valley, is about 45 miles northwest of downtown Chicago . Founded in 1958, the village was developed on the site of the Sleepy Hollow Farm. Though the name comes from "The Legend of Sleepy Hollow," an 1820 story by Washington Irving, the environment is far from scary. Rather, it evokes a secluded, somewhat rural feeling, perhaps with a hint of mystery. "It's an older community and just a nice, quiet place to live. I can't stress it enough that it's not cookie-cutter, you feel like you're in a special place when you are there," says Jane Boeckelmann, a real estate broker with Suburban Life Realty.
According to U.S. Census estimates, Sleepy Hollow's population is about 3,200. The river is a couple of miles to the east, bordering West Dundee .
Roomy 20th century homes, many large lots and some condos
Detached single-family homes make up the bulk of Sleepy Hollow's housing stock, according to a community data snapshot released by the Chicago Metropolitan Agency for Planning (CMAP) in 2023. Most homes were built from the 1950s to the '90s, and include midcentury ranch-style homes, colonial revivals and contemporaries. "The houses are all three to four bedrooms, so it's ideal for families," Boeckelmann says. "There are beautiful architect-designed custom homes. Some are on bigger lots, but they aren't all the same size."
Prices typically range from about $360,000 to $630,000. Subdivisions include Saddle Club Estates, Sleepy Hollow Manor and Deer Creek. Condos, though limited in number, are typically in the 200,000s. Home sites closest to Jelkes Creek may be susceptible to flooding.
Parks, a bird sanctuary, Fox River recreation and Santa's Village
Sabatino Park includes a playground, picnic shelter and a baseball diamond. Lake Sharon is stocked with fish such as bluegills, bass and catfish. To the south, the Jelke Creek Bird Sanctuary has preserved habitats for wildlife, including birds like great blue herons and red-tailed hawks. The Fox River is a destination for outdoor recreation. "Kayaking is a big thing here, there's a lot of biking and hiking along the river," Boeckelmann says. West Dundee has a river walk, and, from East Dundee, the multiuse Fox River Trail is a scenic connector.
It's several miles to Santa's Village Amusement & Water Park in East Dundee . It's open year round, though the water park portion is seasonal.
There's plenty to do in Sleepy Hollow, with community events all year
Many of the community's events are planned by the Sleepy Hollow Service Club and held at Sabatino Park. Halloween in the Hollow includes a chili contest and an appearance by the Headless Horseman. December's Holiday in the Hollow features a tree lighting and visits from Santa. In April, miniature cars made by residents take to the race track during the Sleepy Hollow Pine Car Derby. The July Fourth celebration includes a parade, a pie-eating contest and fireworks.
Some of the most significant area events include the December festival Dickens in Dundee, inspired by "A Christmas Carol," and West Dundee's Heritage Fest, a multiday September celebration with an art and craft fair, carnival games and a car show.
Schools graded B and higher in the Community Unit School District 300
The Community Unit School District 300 serves Sleepy Hollow. Students may attend Sleepy Hollow Elementary School, which earns an A-minus grade from Niche. Dundee Middle School receives a B-plus, and Dundee-Crown High School has a B. The high school has about 30 clubs or extracurricular groups, such as Scholastic Bowl, a chess club and an environmental club.
Shopping and dining in West Dundee or along Randall Road
Sleepy Hollow has no downtown area, so people visit adjacent villages for retail and eating out. "They would absolutely go to West Dundee. There's a lot of good shopping there," Boeckelmann says. The West Dundee French Market is a Parisian-style outdoor market held seasonally. West Dundee also has a Jewel-Osco.
East of Sleepy Hollow, South Eighth Street has retail areas. Restaurants in Century Plaza include Maple & Hash for breakfast and lunch, Gilbert's Kitchen for Chinese cuisine and Dominick's Italian Ristorante. To the west, Randall Road offers a variety of options. "We call it the dining/shopping corridor of Randall Road. It takes you to other city centers. The Randall Road strip in Elgin is considered pretty good."
Winding roads, cul-de-sacs and an Illinois Pleasure Driveway
Sleepy Hollow doesn't have a gridded layout, and it lacks long through streets, so it's walkable in terms of limited traffic. However, sidewalks aren't standard. "There are lots of cul-de-sacs, winding roads and some rolling hills," Boeckelmann says. In 2000, the village employed an 1800s state law to designate the scenic Sleepy Hollow Road an Illinois Pleasure Driveway. This status allows the village to set restrictions on vehicles, speed limits and other factors, thereby preserving the picturesque road.
Commuting, access to highways and nearby medical facilities
According to CMAP's data snapshot, about 75% of people in Sleepy Hollow commute by car, whereas less than 10% carpool or use public transportation. The nearest Pace Bus stops are on the periphery of the village. There's access to state Routes 72 and 31 and Interstate 90, on the north, east and south, respectively. Medical facilities close by include the Advocate Outpatient Center in West Dundee and the Advocate Sherman Hospital in Elgin. It's about a 27-mile drive to Chicago O'Hare International Airport.
Written By
Robin Silberman
