History
Winter Springs sits on the low, marshy south shore of Lake Jesup, and before it had one name the area went by many: Tuskawilla, Wagner, Clifton, Gee Hammock, White's Landing and Solary's Wharf among them. Much of the land was once part of a Spanish land grant held by New York merchant Moses Levy, and disputes over that grant dragged through the courts into the 1850s. In the steamboat era, wharves on Lake Jesup made the shore a landing point for boats coming up the St. Johns River, but once railroads took over after 1880, the lack of a main rail line or highway left the area rural until after 1950.
The town was incorporated in 1959 as North Orlando. The North Orlando Company began building out the western end of town in the late 1950s and early 1960s, and its sales office at Fairfax Avenue and SR 434 later served as the first city hall. The name caused confusion because the town did not touch Orlando, but a 1966 postcard poll narrowly kept it.
In 1970 the Winter Springs Development Corporation acquired about 3,500 acres east of town, including the land that became Tuscawilla Country Club, and an annexation approved in early 1972 roughly doubled the town's size and made it the largest city in Seminole County by land area. A charter revision followed. The council briefly chose the name Semoran, then reversed itself after objections and settled on Winter Springs, which voters affirmed with the new charter.
What it’s like to live there
Winter Springs grew mostly as a collection of separate planned developments rather than around an old downtown. The western end of the city holds the earliest subdivisions, laid out by the North Orlando Company starting in the late 1950s. The large eastern annexation of 1972 brought in the Tuscawilla area, planned around Tuscawilla Country Club, and the Highlands, a community built with its own clubhouse; the Sheoah golf course opened on the northwest side in the same era.
State Road 434 is the main east-west street, and the city's southern and western sections stretch along it while Lake Jesup and its wetlands form the northern edge. Because the shoreline is low and marshy, much of the lakefront is preserve and park land rather than housing.
The Winter Springs Town Center gave the city a center for the first time. Planned by Dover, Kohl & Partners on roughly 200 mostly undeveloped acres, it uses Tuskawilla Road as a main street running off SR 434, linking a busier Market Square with the smaller Magnolia Square, with offices, shops and housing in surrounding mixed-use blocks. Townhomes and apartments flank the shopping core, and new townhome projects in the Town Center District were still going through city review as of late 2025.
Getting around
State Road 434 is the main road through the city, connecting west to Longwood and east to Oviedo. State Road 417, the Seminole Expressway toll road, has an interchange at SR 434 in Winter Springs; it runs south into Orange County, where SR 417 continues as the Central Florida GreeneWay with an exit for Orlando International Airport, and north to I-4 in Sanford, with an exit at Lake Mary Boulevard for Orlando Sanford International Airport.
SunRail commuter trains stop in neighboring Longwood at 149 East Church Avenue and run south through Altamonte Springs, Maitland and Winter Park to downtown Orlando's Church Street and LYNX Central stations, and north to Sanford, DeBary and DeLand. LYNX discontinued its Link 434 bus along State Road 434 in January 2026, so it is worth checking LYNX for current routes before relying on the bus.
The paved Cross Seminole Trail is the best walking and cycling route. It runs through the city on an old railroad bed, crosses SR 434 on a bridge, and has trailheads at the Town Center and Central Winds Park. To the south it reaches Oviedo and continues to the Orange County line near the Cady Way Trail, and to the west it passes Spring Hammock Preserve on the way to Longwood, Lake Mary and Sanford.
Things to do
Central Winds Park, on Lake Jesup near the Cross Seminole Trail, is the city's main park, with sports fields, picnic shelters, a playground and a nature trail with lake views. Near the city dog park, Hicks Avenue leads a short way to a public fishing pier on Lake Jesup, and farther along the trail, the Black Hammock trailhead, on an old rail spur that once ran toward the lake, has parking, water and equestrian parking. Trotwood Park on Northern Way is a smaller neighborhood park.
The Cross Seminole Trail itself is a destination: its section from Oviedo through Winter Springs and Spring Hammock Preserve to Big Tree Park in Longwood follows a former railroad line. Spring Hammock Preserve has an unpaved trail through its wilderness area, Soldiers Creek Park has a short mountain bike trail, and Big Tree Park is known for its very old bald cypress trees and boardwalk.
The Winter Springs Town Center is the closest thing to a downtown, with a fountain, benches and shops around Tuskawilla Road. Golf has been part of the city since the 1970s, with the Tuscawilla and Sheoah courses developed during the city's main growth period.