Juliette Contasti, Real Estate Broker, holding a Sold sign

Real Estate Agent in Winter Park, FL

Winter Park sits just north of downtown Orlando and was laid out as a planned resort town in the late 1800s, which is why it still has a street grid, brick streets in its older sections and a downtown people actually walk. It suits buyers who will trade some square footage for an established, close-in location.

Park Avenue, Rollins and the Train Station

Park Avenue is lined with shops and restaurants, Central Park hosts the Saturday farmers market and the spring Sidewalk Art Festival, and Rollins College sits on Lake Virginia a few blocks south. The SunRail station faces the park, so nearby homes come with a train option into downtown Orlando or north into Seminole County.

Lakes, Canals and Older Homes

Lake Virginia, Lake Osceola, Lake Maitland and the rest of the chain are linked by narrow canals that the Scenic Boat Tour has used for generations. Homes range from 1920s cottages and mid-century ranches to new custom builds where older houses once stood, plus condos near downtown. Not every lake in the city is on the navigable chain, so we confirm boat access on lakefront listings.

Rules Worth Knowing Before You Offer

The city requires a permit to remove many trees on private property, which matters if you plan a pool or an addition. Homes in historic districts such as the College Quarter, or on the city historic register, need design review for exterior changes. Winter Park also runs its own electric utility and has been moving overhead lines underground.

Explore Homes in Winter Park

Call, WhatsApp, email, or book a time. Juliette responds personally, in English or Spanish.

407-283-2412 WhatsApp

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Frequently Asked Questions

Can I live in Winter Park and commute without driving?

Sometimes. SunRail at Central Park runs to downtown Orlando and north into Seminole County. Most residents still drive I-4, US 17-92 or Aloma Avenue, so we test your route at the hour you would actually travel.

Is Winter Park only for luxury buyers?

No. Lakefront estates get the attention, but there are also condos, townhomes and smaller older homes on interior streets. We show you what your budget buys in each before narrowing the search.

Does a Winter Park mailing address mean the home is in the city?

Not always. Some fall outside city limits, and some are in Seminole County rather than Orange, which changes the school district. We confirm jurisdiction and assigned schools for the exact address.