Winter Park

Winter Park Homes for Sale

Learn all about Winter Park

Winter Park is located Northeast of downtown Orlando. In 1880, a railroad track was constructed between Orlando and Sanford. Loring Chase founded Winter Park when he and Oliver Chapmen assembled the land around Winter Park. Loring had found the location after coming to Florida to recuperate from lung disease.  The land was plotted and planned, and the properties were sold with the requirement that all buildings must meet stylistic and architectural standards.  Loring and Chase marketed the property heavily, and during a real estate bubble, the prices of the land rose from $2 an acre to $200 an acre.  The town was visited by Chester Arther and Grover Cleveland.  With reports from newspapers, the town became a fashionable winter resort. Winter Park to this day is one of the wealthiest communities around Orlando.

Rollins College

Rollins College was Florida’s first four-year college which was opened in 1885. The college has been called one of the most beautiful campus’s in the nation.  It is also been ranked among the top universities in the South. The college is nestled along the shores of Lake Virginia. The streets are brick paved and are located within the City of Winter Park on 70 acres.  Rollins has a “Walk of Fame” with stones from across the globe in honor of people and places.

Lake Rose

In May 1981, during low water levels, a large sink hole opened up at the corner of Denning Drive and Fairbanks near the residence of Mae Rose Williams.  The sinkhole swallowed up a tree, home of Mae Rose Williams, five Porsches, a pick-up truck and the Winter Park municipal pool. The sink hole was described as “the largest sinkhole event witnessed by man as a result of natural geologic reasons or conditions.”(Winter Park Magazine) The sinkhole began to fill with water over the following months, and the city repaired the damage by removing several of the Porsches and the truck and then filling the bottom with dirt and concrete. The sinkhole gradually filled with water and became named as Lake Rose in honor of Mae Rose Williams.

Ward Park 

Ward Park is a large public park is a 66 acre park supporting many athletic needs in the area. The park has a playground, four tennis courts, ten baseball fields, five soccer fields, pavilion, stadium, two concession buildings, restrooms, fitness trail, bike trail, walking path, little league complex and one olympic-sized pool.  Ward Park is home to many children’s athletic teams including the training of Orlando City Soccer’s Little Lions team (children ages 4-8).

Winter Park Village

Winter Park Village is located on 17-92 between Lee Road and Fairbanks Avenue.  It offers local residents and travelers high-end retailers and restaurants as well as a cinema.  It is an open-aired shopping center with numerous boutiques.

Park Avenue

Park Ave which is located just across the street from Rollins College is lined with more upscale shops and restaurants to meet the needs of the affluent residents of Winter Park and the surrounding area. At the center of Park Avenue, is a large open park with trees and fountains.  The railroad runs to one side of the park making a great stop along the train line which connects commuters from as far away as Debary to the final stop at Sand Lake in Orlando. Its a great location to enjoy lunch or take the kids for ice cream and enjoy the park.


There are four public elementary schools in Winter Park including Brookshire, Lakemont, Audubon Park, and Dommerich. Maitland, Glenridge, Jackson, and Union Park are the Middle schools in Winter Park. The high Schools are Edgewater, Maitland and Winter Park. There are several of these schools which have poor school grades. Many of the local affluent residents living in the area have their children in private schools. School zones change so be sure to verify the school by address before purchasing a property with Orange County Public Schools. The school grades also change. It is a good idea to look at grades over a few year period to get an idea on the overall character of a school.


In an effort to keep the speed down in Winter Park, the city ripped up the paved concrete and added brick roads which have added a charm to the community.  Older homes have gradually been undergoing remodeling.  With it’s close proximity to downtown Orlando, Winter Park is highly sought after with those working in downtown Orlando wanting to avoid heavy commute times.  Homes in Winter Park vary in price depending on size, condition, and location.  Small older homes can be found in the high 100k’s to 200k’s.  As size and condition increase, the price significantly increases. There are large remodeled homes and large newer homes on large lots that are priced as much as $6 million.  Some lake front homes with gorgeous lake views also have soaring price tags.

Winter Park Homes for Sale

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