Winter Garden Neighborhood Guide

Winter Garden neighborhood guide: What’s new, why residents call it home & can’t-miss things to do

Though Winter Garden’s facade is one of quaint and lovingly preserved and/or restored brick, it was the orange blood of the citrus industry that first fueled this city’s growth. Beautiful brick streets lined with indie businesses, a fun and formidable indoor market and a trail system that lures the outdoorsy, make it an enticing choice for folks looking for both downtown proximity and small-town appeal.

A claim to fame

It’s high! Well, for Florida, anyway. Winter Garden boasts the highest elevation in Orange County, a whopping 222 feet above sea level.

Why live here

Colin Sharman, 42, has called Winter Garden home for 21 years. He has spent the last 11 years serving District 4 as its commissioner.

“Winter Garden has a thriving downtown with a small-town feel and historic charm,” he says, crediting the West Orange Trail as a catalyst for the area’s restoration and renaissance. “People would stop downtown for breakfast and lunch, and that in turn allowed new businesses to come in, prompted city investment and much of what residents and visitors enjoy today.”

In his own district, once home to orange groves, development continues, as well.

“Recently, Florida Hospital’s come in and brought with it high-quality jobs and great medical care for our community.”

Sharman touts events such as downtown music festivals, Light Up Winter Garden in the holiday season and spring’s Bloom & Grow garden fest, which also put the city on the Central Florida radar.

“There’s a sense of community here,” he says. “It’s not just a sprawling city.”

Coming soon

More downtown residents. A new mixed-use development, including 22 new luxury apartments, is slated for construction on the corner of Tremaine and South Boyd Streets, hence its name: Tremaine Boyd. Its target completion date is spring 2019.

Don’t miss

  • Central Florida Railroad Museum: This donation-funded gem is bigger on the inside, with more railroad artifacts than you’d imagine could fit. Photos and phenomenal memorabilia await. A must for train buffs. (101 S. Boyd St.; 407-656-0559)
  • Garden Theater: Architecture buffs will love its Mediterranean Revival style (the theater was built in 1935), fans of the arts will love its lively schedule of plays, concerts, films and more. (160 W. Plant St; 407-977-4736)
  • West Orange Trail: Only part of the trail’s 20.8 miles are in Winter Garden, but it’s a great place to start. Need a bike? Rent one at Winter Garden Station for $10/hour. (501 Crown Point Cross Road; 407-654-1108)

Dig in!

Dining options from Orlando Sentinel Foodie Lauren Delgado:

  • Chef’s Table at the Edgewater: For a heavily awarded restaurant, the experience at the Chef’s Table is intimate and down-to-earth, from the exceptional service to the sensational food on its prix-fixe menu. (99 W. Plant St., Winter Garden)
  • Plant St. Market: Plant St. Market hosts a slew of vendors hawking everything from wild Florida honey to candles. The eats and drinks in this indoor space are just as varied: sushi, mac and cheese, pizza, burgers, ice pops and more. Grab a brew from the business that started it all, Crooked Can Brewing Co. (426 W. Plant St., Winter Garden)

Find out more

Use our lifestyle finder or contact one of our local Realtors to get more information about living, working, and playing in Winter Garden!


Source: “Winter Garden Neighborhood Guide,” Orlando Sentinel