Real Estate Information on Maitland Market and Winter Park Market

Maitland and Winter Park, two cities just north of downtown Orlando are located right next door to each other. While both are known for their upscale homes and estates, chain of lakes, and array of parks, they also have quite the small-town feel with a real sense of community among neighbors.

Winter Park is known for it’s “olde downtown” area featuring winding brick streets canopied by old oak and camphor trees dripping in Spanish moss, an eclectic mix of shops and restaurants along Park Avenue, bordered by Central Park, home to the rose garden and site of many outdoor festivals and events, a quaint little train depot, and Florida’s first four-year university, Rollins College. There are currently 320 single-family homes available for sale in the city of Winter Park with prices ranging from just over $40,000 to nearly $9,000,000 with most homes priced in the ballpark of $250,000-$400,000.

Maitland is best known for it’s illustrious school district, featuring Dommerich and Lake Sybelia Elementary schools, Maitland Middle and Winter Park High, is home to the Florida Film Festival, held annually at the only independent movie theatre in Central Florida, the Enzian, as well as the Maitland Art Center, listed on the historic registry and featuring unique Mayan/Aztec sculptures, murals, and bas reliefs. Maitland currently has 161 single family homes available for sale ranging from $46,000 to $3,500,000 with most homes also priced in the ballpark of $250,000-$400,000.

Living in the Winter Park Maitland area can include Saturdays boating on the lake, Sundays eating crepes for breakfast at the farmer’s market, lunch at Palmano’s outdoor cafe, and dinner at Antonio’s. Have a drink at Luma’s or enjoy a glass of wine while watching the sun set over the lake on the lawn at Houston’s. Once a month you can lay down a blanket, bring a picnic basket, and watch the movie in central park but it’ll be interrupted from time to time as they’ll pause the movie when the train goes by. There’s a line outside of Jeremiah’s Italian ice every night around 7pm and everyone hangs outside to eat. Sometimes the local fire department will even stop by and join in. The parents at Dommerich elementary not only send their kids there, they went there themselves years ago, and grew up in the same neighborhood they now live in with their own families. You’ll find pancake breakfasts, street parades, kids riding bikes and playing street hockey… it truly is a throwback to times gone by but can still be experienced today.

If you’re looking for a great neighborhood full of history, a sense of true community spirit, and plenty of places to get outside and play… look no further than the Winter Park Maitland area.