A sleepy town with historic homes and maybe some ghosts
Founded in 1827, the small town of Monticello is blooming with historic charm and community spirit. As the seat of Jefferson County, the downtown area is home to multiple buildings dating from the 1800s, including the historic Perkins Opera House, as well as restaurants, coffee shops, boutiques, bed and breakfasts and more. “Monticello is a modern-day Mayberry. People are very nice. When somebody passes away, everybody goes to the funeral, and it’s standing room only. It's caring and neighborly,” says Lynette Sirmon, a real estate agent with All Realty Services with more than 45 years of real estate experience in the Tallahassee area. “There are no traffic lights. It's a sleepy little town.” And with all those historic homes, it’s no surprise Monticello is widely recognized as the most haunted small town in the South. Ghost tours are offered year-round.
Numerous mom-and-pop restaurants are clustered downtown
Monticello’s downtown area, with a roundabout encircling the stately Jefferson County Courthouse, exudes small-town charm, and its restaurants are great places to experience it firsthand. In the morning, CowHaus Coffee Company is the go-to spot for an espresso and pastry. Locals settle in to chat over pancakes, chicken salad and burgers at Jackie’s Brickhouse Eatery, which is also downtown. Two blocks north, Rev Café serves burgers, sandwiches and classic southern fare like shrimp and grits and fried chicken. The Jefferson Farmers Market, open every day except Sunday, sells local produce and meats, including Southern classics such as boiled peanuts. Winn-Dixie is just south of downtown, and big-box retailers are about 30 miles away in Tallahassee.
Historic homes date to the 19th and 20th centuries
Old Florida charm radiates across the historic core, where moss-draped live oaks frame a diverse range of historic homes, including 1920s bungalows, mid-century cottages and classic Florida cracker homes. Victorian mansions with turrets and sweeping verandas as well as neoclassical and Greek Revival homes with large columns and porticos are also seen. Many of these buildings have been converted into local businesses, but some are still residential. When they pop up on the market, historic homes typically list between $330,000 and $500,000, depending on the degree of renovation. Beyond the historic district, residential properties include mid-century brick ranch-style homes and Minimal Traditional homes on mid-sized lawns. Further west along Washington Street toward Monticello’s city limits, brand-new developments feature spacious homes with farmhouse and Craftsman accents. Prices across Monticello range from $170,000 to $600,000.
The Monticello Bike Trail runs through downtown
For a walk, Sirmon recommends the Monticello Ecological Park, which has a loop trail just under a mile that winds through pine and live oak trees. Just south of downtown, Clifford Brown Memorial Park, also known as Chase Street Park, has a playground and open green space. The Monticello Bike Trail runs along the edge of the park, so cyclists can conveniently hop on the 2-mile path and pedal north-south through the city. The Monticello Community Garden has plots available for local gardeners. The Jefferson County Recreational Park has four tennis courts, a playground and a baseball complex with several ball fields.
The elementary, middle and high school share a campus
Children of all ages attend Jefferson Somerset K-12 School, also known as Jefferson Somerset Academy Charter School, which includes three separate schools serving elementary, middle and high school students. Originally housed in the first brick school building in Florida, Jefferson Academy was established in 1852 and moved to its present facility in 2004. The elementary school and the middle school earn a grade of C from Niche while the high school earns a B.
Watermelons, ghouls and Christmas have their own celebrations
As a small town, Monticello prides itself on hosting community events and festivals throughout the year, including the two-day Watermelon Festival in June and the Ghoul’s Night Out and Downtown Candy Crawl close to Halloween. Each year on December 1st, the Downtown Monticello Christmas celebration features a Christmas Light Parade, tree lighting, plus live music and local vendors. Perkins Opera House hosts classic plays and musicals. Tom Brown Park in Tallahassee throws a big regional Fourth of July celebration, with fireworks, live music and food trucks.
Downtown Monticello is pedestrian friendly
Downtown is easy to navigate without a car. “Everything is within one mile,” says Sirmon, and it's easy to get around. “It’s walkable, people use golf carts and bicycles.” Commuters from Monticello drive to either Tallahassee or to Thomasville, Georgia for work, and both cities are about a 30-minute drive away, says Sirmon. Tallahassee International Airport is 40 miles west.
