Winter Park

With its tony brick streets, trendy shopping, dining scene and million dollar homes, Winter Park is a very well-known city in the Orlando metro region, but it’s larger than most people realize, spreading far beyond posh Park Avenue and a place with many affordable housing options, as well. Young families will be lured by its top-rated schools, empty nesters by the myriad shopping, dining, and entertainment. Rollins College, of course, brings in a new crop of students each year. Many fall in love with the area or Orlando in general and never go home.

Winter Park is one of Orlando’s best areas. Its thriving center and the best-known neighborhood is Park Avenue, where high-end restaurant and boutiques are buffered by museums and galleries, lovely Central Park with its fountains and towering oaks and nearby Rollins College, with its beautiful Spanish Colonial architecture. The surrounding neighborhoods are among the metro’s priciest, but fanning out, homes grow more affordable.

A train runs through Winter Park, literally — Amtrak and SunRail passengers disembark into Central Park with the spoils of Park Avenue at their fingertips. Less than eight miles from downtown Orlando, one could easily take Interstate 4 for a commute, but many area residents simply take local roads. Between congestion and construction– Orlando is a growing city– you’d do better to learn the local streets, anyway.

Beyond the obvious spoils of Winter Park’s downtown– rife with highly regarded bistros and bars– its chain of lakes offer opportunities for water pursuits, whether hopping into a kayak or opting for the city’s boat tour. You could also catch the sunset over cocktails at Hillstone or a burger at Shake Shack and avoid the possibility of getting wet altogether. Annual events, from the Sidewalk Arts Festival to the foodie-friendly Cows’n Cabs, fill the calendar.