Winter Park Country Club and Golf Course

Casa Feliz, or "Happy House" in Spanish, is the signature residential work of noted architect James Gamble Rogers II. Initially known as the Barbour Estate, this Andalusian-style masonry farmhouse has significantly influenced the architectural and cultural aspects of this community. This house is one of Rogers' best-known residences in Florida. In 2000, in order to save it from destruction, the city of Winter Park moved it to its current location at 656 Park Avenue North in Winter Park. On December 31, 2008, it was added to the United States National Register of Historic Places.

The Tiffany Chapel is a chapel interior designed by Louis Comfort Tiffany and created by the Tiffany Glass and Decorating Company. First installed for the 1893 World's Columbian Exposition in Chicago, the chapel was later moved to the Cathedral of St. John the Divine in New York City, then re-acquired by Tiffany in 1916 and displayed in his own home. After the chapel was dismantled in 1949, parts were sold and the remaining portions were put on display at the Charles Hosmer Morse Museum of American Art in Winter Park, Florida in April 1999.

Winter Park station is a train station in Winter Park, Florida. It is served by SunRail, the commuter rail system of Greater Orlando, and Amtrak, the national passenger rail system of the United States. The current station was built in 2014, replacing earlier stations going back to 1882.

Interlachen Avenue Historic District is a national historic district in Winter Park, Florida, Orange County. Including buildings constructed from 1882 through 1964, it is bounded by Canton Avenue on the north, Knowles Avenue on the west, Lake Osceola on the east, and New England Avenue on the south.It was added to the National Register of Historic Places in 2011.

Downtown Winter Park Historic District is a national historic district in Winter Park, Florida, Orange County. Including buildings constructed from 1882 through 1965, runs along Park Avenue from Canton to Comstock avenues.It was added to the National Register of Historic Places in 2011.

Winter Park History Museum, also known as the Winter Park Historical Museum, is a local history museum in Winter Park, Orange County, Florida. It is operated by the Winter Park Historical Association and located in a former railroad freight depot.The museum's collections of historic artifacts include area schools, medical and military items, vintage postcards and photographs, Boy Scout items, and items of local businesses and industries. Exhibitions have included local area history subjects such as area railroads, the history and culture of the turpentine industry, Winter Park High School history, and the city's Colony Theatre (Winter Park, Florida).

Winter Park Village is an outdoor shopping center in Winter Park, Florida, United States featuring many shops, restaurants, and a 20-screen Regal Cinemas. The center opened in 1999 on the site of the former Winter Park Mall.

The Seminole Hotel was a hotel in Winter Park, Florida. The hotel opened on January 1, 1886 and had 250 guest rooms. It was situated on a site bounded by Osceola Avenue and Lake Osceola and sat at the eastern end of New England Avenue . Many people referred to it as the grand resort of Florida. At that time, wagons, carriages and bicycles were the only common modes of local transportation. The hotel operated its own street railway which ran from the South Florida Railroad station up New England Avenue, a distance of approximately ⅓ of a mile to the hotel. A slight extension down Chase/Ollie Avenue from the hotel to the Orlando and Winter Park (AKA: The Dinky Line) Railroad station and dock on Lake Virginia was completed after that railroad opened. Riding the horse drawn streetcar, hotel guests avoided the bumpy, sandy streets surrounded by posh comforts of velvet, brass and polished native and exotic hardwood finishes. Indeed, all of the streetcars manufactured by the John Stephenson Company in New York City, were state-of-the-art and on the cutting edge of urban transportation development. Many of these passengers came to Winter Park in the winter months to escape the snow and frigid temperatures of the North. In its early years, the hotel was able to attract many wealthy northerners using luxuries such as gaslights and steam heating. The hotel featured a 42 x 100 foot beautiful formal dining room, many parlors, suites with open fireplaces, a barbershop, laundry services, and a 567 foot long colonnaded porch. Guests could take the elevator to view the surrounding area from the promenade on the top of the hotel. For the guests entertainment, the hotel provided a bowling alley, a billiard hall, tennis and croquet grounds, and an orchestra for dancing. Other activities including horseback riding, fishing, and sailing on Lake Osceola in sailboats and steam yachts provided by the hotel.Along with neighboring Rollins College, the hotel and college brought luxury to the edge of the Florida frontier. The college’s opening offered many job opportunities around the Orlando area. For African-Americans living on the west side of Winter Park, this was crucial. Many young African-Americans were able to find jobs at the Seminole Hotel and earn decent wages. On February 24, 1888, President Grover Cleveland visited the Seminole Hotel, along with several senators and prominent citizens from the nation's capital.The original Seminole Hotel burned to the ground in September, 1902. In 1912, a second, smaller Seminole Hotel was built. The new hotel was located on East Webster Avenue and sat on the northwest banks of Lake Osceola. This hotel was torn down in 1970.

Hannibal Square Library was a library established to serve the Black community in Winter Park, Florida that operated from 1937 to 1979. In 1881, the Hannibal Square neighborhood was built to house to Black families who worked for white residents and visitors and in the railroad or service industry. In 1936, Mertie Graham Grover, a former teacher, was hit by a car and killed in Winter Park. Her husband, Rollins College professor Dr. Edwin O. Grover, started a fund to build a library in her memory in the Hannibal Square neighborhood that would serve the Black residents who were barred by segregation laws from using the county library. The Hannibal Square Public Library-Mertie Graham Grover Memorial was built on the north side of West New England Avenue near Pennsylvania Avenue, next to the Black elementary school. It opened on July 1, 1937. In the 1950s, the library began to receive some funding from the city, although less than the public library received. In 1955, a children's room was added, funded with donations of time, labor and money. In 1962 and 1963, the Winter Park Public Library changed its policies to allow all residents, regardless of race, to access its library services. In 1968, Hannibal Square Library became a branch of the Winter Park Public Library. In 1979, the Hannibal Square library closed when the 460 East New England Avenue library opened. The Hannibal Square building was moved to a place behind the Winter Park Community Center.

The Hannibal Square Heritage Center is a community center in Winter Park, Florida which is run by the Crealdé School of Art. Founded in 2007, the Hannibal Square Heritage Center is located in a historical neighborhood on New England Avenue two blocks west of Park Avenue, between Virginia and Pennsylvania Avenues. Operating and programming costs are funded by Crealdé School of Art, the Community Redevelopment Agency of the City of Winter Park, United Arts of Central Florida and the Division of Cultural Affairs through the State of Florida.

Mount Moriah Missionary Baptist Church was founded in 1886 and was the first black Baptist church organized in Winter Park, Florida, United States. Originally, the church began at the home of Reverend Charles and Mrs. Missouri Ambrose on Pennsylvania Avenue in the town's predominantly African American Westside. The church presented the community with a safe place to form close friendships, and offered a number of wholesome activities for children and adults. Clyde W. Hall, a member of the church, recalls that “the church also provided a place where African-Americans could dress in their best attire on Sundays and enjoy equality without encountering the racial deprivations of everyday living in the South at that time.” The first minister to lead the congregation was Reverend Charles Johnson Smith, who came to Mount Moriah in 1887. Reverend Smith's position as a moderator of the First Florida Missionary Baptist Association helped allow the developing church to be granted membership in the organization in 1910. Reverend Smith continued to serve Mount Moriah until 1911.

Winter Park is a city in Orange County, Florida, United States. The population was 30,183 according to the 2022 census population estimate. It is part of the Orlando–Kissimmee–Sanford, Florida Metropolitan Statistical Area. Winter Park was founded as a resort community by northern business magnates in the late 19th and early 20th centuries^ . Its main street, called Park Avenue, is located in the middle of town. It includes civic buildings, retail, art galleries, a private liberal arts college (Rollins College), museums, a park, a train station, a golf course country club, a historic cemetery, and a beach and boat launch.