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Winter Park

Winter Park

The beautifully crafted suburb of Winter Park lies just outside of downtown Orlando. What was founded as a resort community in the late nineteenth century has quietly blossomed into a cultural and economic hub for the greater Central Florida area. Additionally, with a multitude of educational institutes and outdoor activities, this brick-paved town of Approximately 29,000, combines old Florida charm with modern amenities and geographic centrality. With virtually more history and parks than any other area in Central Florida, Winter Park is an ideal place to call home.


Due to its close proximity to Orlando, Winter Park is an ideal commuter neighborhood for those working in and around the downtown area. Situated amongst the Winter Park Chain of Lakes, the town of Winter Park was incorporated in 1885, after which, land prices jumped from less than $2 an acre to over $200 per acre (proof that it has always been a great place to put down roots). Once a stopping point for the now-defunct Atlantic Railroad, Winter Park is now home to a stopping point on the new SunRail commuter system. SunRail currently links twelve stations in three counties via state-of -the-art commuter trains (with expansion plans in progress). The current rail station is located in downtown Winter Park’s historic Central Park and is also serviced by Amtrak. Winter Park is serviced by a well-connected roadway system as well, with I-4, the 408 (East/West Expressway), and the 417 (Greenway) being readily accessible. Both Orlando International Airport and the Sanford Executive Airport can easily and quickly be reached using these high-speed highway routes.


The beautiful downtown area is the primary focal point of this lovely community. Old Winter Park is nestled under a gorgeous canopy of old southern live oak and camphor trees with winding brick streets for added character and charm. The area plays host to many different festivals and gatherings throughout the year including the nation’s largest and oldest juried outdoor arts festival. The Winter Park Art Festival has been rated as one of the top shows by Sunshine Artist and American Style magazines and has been a Winter Park standard for over fifty years drawing hundreds of artist from all over the world. Additionally, Winter Park hosts the Bach Festival in the spring as well as the Florida Film Festival which showcases new talent and independent films. The Winter Park Farmers’ Market takes place every Saturday and is a great opportunity for residents to shop local produce and goods. The Winter Park area provides an array of services and amenities to its community including the Winter Park Garden Club, Winter Park Country Club, Winter Park Tennis Center and the Winter Park Library, among many others.


Winter Park has a well-earned reputation as a top-notch educational destination. From the first years of a child’s education to the graduate degree stage, the options are all first-rate. The area is served by the Orange County School district and offers a variety of options for elementary and middle schools. Winter Park High School and Trinity Prep are among the top choices for high schools in the area and the options for post- high school are even more varied. Winter Park is home to the Crealde School of Art, a non-profit, all-ages art school, Full Sail University, which specializes in degrees focused on the entertainment industry, and Rollins College, a liberal arts college which is also home to Crummer School of Business featuring a top-ranked and nationally accredited MBA program. There are also numerous possibilities to expand one’s cultural education as Winter Park boasts an impressive array of museums, galleries and parks. These include: The Charles Hosmer Morse Museum of American Art which houses the largest collection of Tiffany Art in the world; the Cornell Fine Arts Museum featuring painting, prints, drawing and photography; the Kraft Azalea Garden with thousands of azaleas, tropical shrubs and trees; the Mead Botanical Gardens; the Albin Palosek Museum and Sculpture Gardens with world-class sculptures and paintings; and Ward Park, featuring 66.44 acres of dedicated sports fields including baseball/softball, soccer, and football among others. This list only scratches the surface of all that the city of Winter Park has to offer for cultural and educational enrichment and enlightenment—there is so much to see and do within this small part of Orlando.


The downtown area which includes Park Avenue is the bustling commercial heart of Winter Park. This beautiful area offers boutique shops, cafes and the Park Plaza Hotel. One can grab a quick lunch at the Briarpatch and the Coop or enjoy an evening out at the Park Social Winter Park or the Red Lion Pub. For additional options, the Winter Park Village area lies off of Canton Avenue, halfway between Park Avenue and I-4, and has Interesting restaurants, local boutiques, and a large Regal movie theater. For other accommodations when in the Winter Park area guest can visit the Alfond Inn. The Alfond Inn is a stunning boutique hotel which was rated the #2 hotel in Florida by Conde Nast readers in 2014. Winter Park has myriad opportunities for business growth and development. From retail to restaurants, investment opportunities abound for small business entrepreneurs. And, although it has a small-town feel, there are a few corporate offices which have their homes in Winter Park; among them are Adventist Health System and Bonnier Corporation.

Real Estate

If one takes a stroll in and around Winter Park they will notice that nearly every home is different and has its own character. The downtown area has an eclectic blend of townhomes, boutique cottages and grand estate homes. In the areas surrounding downtown one can find diverse homes in both established neighborhoods and those which are newer. There are many great neighborhoods in the Winter Park area, among them are: Comstock Park; Sevilla, which features a unique blend of architectural styles; Casa Jardin with its old world Spanish-style homes; and the Via’s area which is one of the most highly sought after areas of Winter Park. Whether one is looking to find a great starter home with the feel of a wooded cottage or if it’s a Tudor style manor that is warranted, Winter Park offers some of the most diverse real estate options in all of Orlando.

Comstock Park



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