Homes For Sale In Winter Park FL

Winter Park is home to traditional yet sustainable living.  Find homes for sale in Winter Park FL and research local real estate market trends. Search new listings, scheduled open houses, recent solds, and price reductions in Winter Park. To adjust how your search is displayed, click the gray arrows next to "Sort" to display Winter Park homes in Orlando by price, number of bedrooms, or days on market.

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Winter Park is one of Orlando’s finest cities, it is famous for spectacular homes, abundant parks, world class museums, beautiful lakes, and fine shopping. Winter Park is a city of about $37,000 residents just north of Orlando. With some of the cities best dining experiences, most luxurious homes, and serene nature parks, Winter Park is one of the most desirable places to live in Central Florida.

Winter Park is a small city full of rich history. Starting out as an eight-acre parcel of land purchased in 1858, Winter Park was originally called Lakeview. By 1883, the city expanded by 600 acres and was renamed Winter Park. The city was originally intended to be a winter haven for wealthy northerners seeking refuge from the harsh winters, ergo the new name, a park for the winter. In 1883, Winter Park’s first school opened and quickly following the public library which is still the library today. However, come Spring of 2021, a new public library facility is set to open with world-class, future ready technology. 

Ever expanding and changing with the times, Winter Park’s combination of established roots and new construction homes provides the area’s unique charm and pull to live here. There is plenty of tradition in Winter Park but the city also treasures new, eclectic architecture as well. Spanish-roofed architecture is prevalent in the area, but you will also see traditional American styled homes, Mediterranean features, and contemporary styles with playful colors and bright greenery. 

Winter park is a Mecca for world-class art and rich cultural experiences. A city filled with art and culture, Winter Park cherishes its traditional charm while building a sustainable future for the generations to come. Considered by many to be a premier urban village in the sunshine state, Winter Park is coined one of the finest cities in the United States. 

Winter Park is home to the one and only “Park Ave.” A destination for dining and shopping like none other. With more than 140 upscale boutiques and restaurants, on Park Ave you can find almost anything your heart desires. One night enjoy more laid back traditional Turkish cuisine from Bosphorous and then tomorrow you can treat yourself to a fine dining experience in a five-star environment at Luma on Park. 

Winter Park is also home to A-rated elementary, middle and high schools, outstanding and always happening community events, and one of the most amazing college campuses in the US, Rollins College. Whether you are seeking refuge from the cold north and retiring in Winter Park or coming to this unique city to start your family, Winter Park is a city like none other. The demand to live in this traditional, eclectic city is always high.