Winter Park packs a lot into a small city: brick streets under a canopy of old oaks, a chain of lakes, a lively downtown on Park Avenue and neighborhoods that range from 1920s bungalows to new builds. It is a wonderful place to live. It also has a few quirks that can turn a simple move into a long day if you do not plan for them.
Here is our local guide to moving to Winter Park, whether you are coming from across town in Orlando or from somewhere else in Florida.
Why people love living in Winter Park
- Park Avenue and Central Park: shops, cafés and restaurants around a leafy downtown park, with a SunRail station right next to it.
- The Chain of Lakes: a string of lakes connected by canals, famous for the long-running Scenic Boat Tour.
- Saturday Farmers' Market: a local tradition held at the historic train depot downtown.
- Culture close to home: Rollins College and the Morse Museum, home to a large collection of Tiffany glass.
- Easy reach: Orlando, Maitland and I-4 are minutes away.
Moving-day challenges in Winter Park
The same things that give Winter Park its character can slow a move down. Knowing them ahead of time is half the battle.
Brick streets and narrow lanes. Many older neighborhoods have narrow brick streets with cars parked on both sides. A big truck may not fit close to your door, which means longer carries.
Low oak branches. The famous tree canopy is beautiful, but low limbs can block a tall truck from pulling into a driveway or down a street. A smaller truck, or two trips, is sometimes faster than a long walk from the corner.
Older homes. Classic bungalows often have narrow doorways, tight hallways and steep stairs. Measure large furniture and doorways before moving day so there are no surprises.
Downtown condos and apartments. Buildings near Park Avenue usually have loading rules, elevator reservations and limited parking. Ask the management office what they require at least a week ahead.
Tell us about your street
When you ask for a quote, mention if your street is narrow, has low branches or has no driveway. It helps us pick the right truck size and avoid a long carry on moving day.
Your Winter Park moving checklist
Before moving day
- Measure your largest furniture and the new home's doorways
- Ask your HOA or building about moving hours and elevator booking
- Check whether you need permission to park a truck on the street
- Save a spot in the driveway or in front of the house
- Plan around big downtown events that close streets
- Pack, tape and label every box by room
For questions about street parking or road closures, the City of Winter Park website is the best place to check.
Best time to move in Winter Park
Weekday mornings are usually easiest: less traffic, more open parking and cooler temperatures. Avoid Saturday mornings near downtown when the farmers' market is running, and keep an eye on the city's event calendar for weekends when streets around Central Park close.
The cooler, drier months from late fall through spring are the most comfortable time to move anywhere in Central Florida.
Moving within Winter Park or nearby?
We handle local moves in Winter Park and the surrounding area every week, including apartment and condo moves with elevators and loading docks. See our Winter Park movers page for more about the area we serve.
Planning a move to Winter Park?
Our 2-mover crew is $129/hr with no travel fee, and we speak English and Spanish. Request a free quote and tell us about your street, and we will help you plan the right truck.
Frequently asked questions
Is it hard to move a big truck in Winter Park?
In some older neighborhoods, yes. Narrow brick streets, parked cars and low oak branches can keep a large truck from getting close to the door. Telling your mover about the street and parking ahead of time helps them choose the right truck size.
Do I need a permit to park a moving truck in Winter Park?
It depends on the street and how long the truck will be there. Check with the City of Winter Park and your HOA or building management before moving day.
When is the best day to move in Winter Park?
A weekday morning is usually easiest. Traffic is lighter, parking is easier and it is cooler. Try to avoid Saturday mornings near downtown and weekends with big events.