Downtown Winter Garden Neighborhood Guide

Updated: Oct 9, 2019



SCOPE | A CORNER STORE STYLED DOWNTOWN


Downtown Winter Garden is an inspiring testament to community revitalization. It

started as a small, citrus growing town in the early twentieth century, ebbed into a

sleepy suburb by the 1960s and, over the last twenty years, has bloomed into a

vibrant stretch of neighborhoods, shops, restaurants, and businesses.


Backing up to Lake Apopka’s south shore, this collection of brick roads, homes, and old Florida foliage has become an uncommon, deeply loved area for many.


FEEL | OUT & ABOUT


A day in the life could look like. . .


Jump “on the trail” for a morning run or ride. Grab a cup of coffee at the local spot on your way out of town (expect to be delayed 5 minutes by a familiar face). Commute to work. Return home in the evening for a walk or golf-cart ride down to Plant Street Market dinner and a beer.


ARCHITECTURE | MODERN, MIDCENTURY & CONTEMPORARY


The skyline is framed by a rare assemblage of buildings —young and old— spreading from the edge of Lake Apopka to Colonial Drive. The variety of homes range from bungalows built over half a century ago, to modern ones crafted to effortlessly fit alongside history while still incorporating hip additions.


Many of the more historic homes have been recently outfitted with new flooring and appliances, while some are just waiting to be your next fixer-upper project!




MARKET | TBD





WHAT TO EXPECT | KINDNESS IN A THROWBACK SETTING


As a “Winter Gardian”, it’s likely you will know your neighbors, live in or near a home with history and eccentricities, and enjoy Plant Street festivities on weekends and holidays.


WHAT MAKES IT UNIQUE | SMALL BUSINESS SPIRIT


So far, this area has somehow been able to maintain its small-town vibe, while becoming a garden of new restaurants, businesses and local chains in the last ten years.


The general age range of the community remains a wide balance of young professionals, families, and locals who have lived there for 40+ years, turning into a diverse and friendly marketplace.



PRACTICALLY SPEAKING | LIMITED PARKING, ARCHITECTURAL QUIRKS & ISLAND LIVING


Limited parking

It might take a little time to get street-savvy in navigating your way through parked cars, small crowds and cyclists on the main strip during the busy weekends and seasonal festivals.


Architectural quirks

While the number of new developments is quickly growing, the older buildings

feature quirks like limited closet space and small kitchens.


Island living

Because the charm and commerce of the area are so strong, it’s easy to forget you can venture out into other great parts of Central Florida in under a half-hour drive.

NEIGHBORHOOD LANDMARKS | FESTIVALS & MARKETS


Winter Garden Farmer’s Market

Every Saturday from 9 am - 2 pm.


Fridays on the Plaza

Enjoy live music every Friday night.


Garden Theater

Local productions + concerts year-round with classic family movies in the summer.


The Edgewater Hotel

Established in 1927, a historic bed and breakfast.


Annual Festivals

Spring Fever in the Garden, Winter Garden, Blues & BBQ, Light Up Winter Garden, etc.


Plant Street Market

Indoor market with surrounding patio seating.

EATS | MOM & POP


Breakfast & Coffee

Axum Coffee Community, Rosallie’s Le French Cafe, Sir Benji’s Donuts, Eggs & Oats.


Bites & Beverages

Urban Flats, The Attic Door Cafe & Wine Bar, Pilar’s (Martini), The Whole Enchilada

Fresh Mexican Grill & Bar, The Mooncricket Grille, The Deli Downtown, BurgerFi,

Scoops Old Fashioned Ice Cream Store, The Crooked Can Brewery, This Little Piggy,

Press’d Juice Bar, Michael’s Alli Pizza, Mac’d Out, Servando’s.


The Finer Side

Thai Blossom, Chef’s Table, Matthew’s Steakhouse, Market to Table

Cuisine.


SHOPPING | SPECIALTY


Plant Street Market

Small, local shops for essential oils, honey, locally roasted coffee, etc.


The Farmacy

Local, organic grocery store.



Adjectives Market

Hand-crafted home goods + vintage finds


Tri & Tun of West Orange

Athletic wear + shoes.


Winter Garden Wheel Works

Road bikes + cycling gear.


Woof Gang Bakery

Neighborhood pet store + groomer.


Winter Garden Village

9 min drive


Mall at Millenia

20 min drive


Disney Springs

28 min drive


PARKS & REC | TRAILS & WATERFRONT


West Orange Trail

22 mile-long multi-use, paved trail.


Newton Park

Lakefront picnic area with playground, fishing, community pool.


Chapin Station

West Orange Trail access with playground, garden + tennis/basketball courts.


Veteran’s Memorial Park

Picnic area with basketball, tennis + volleyball courts alongside multipurpose fields.


Jessie Brock Community Center

Outdoor trail with workout stations + a center for community arts/recreational classes.


Winter Garden Interactive Fountain & Splash Pad

Open every day from 9 am - 9 pm.


SCHOOLS | PUBLIC & PRIVATE


14 top public schools • Average student:teacher ratio of 18:1


Public

Dillard Street Elementary School, Tildenville Elementary School, Maxey Elementary

School, Lakeview Middle School, West Orange High School


Private

Montessori Academy of Winter Garden, St. Lillie V High School, Foundation Academy

North Campus


Higher

Orange Technical College, Westside Campus

6 min drive


Lake Sumter State College, Southlake Campus

19 min drive


Valencia College, West Campus

23 min drive


University of Central Florida

35 min drive


COMMUTE TIMES (ISH) | 23 MINUTES


Places to Go


Windermere

18 min


Disney

20 min drive


Apopka

22 min drive


Downtown Orlando

23 min drive


Downtown Clermont

23 min drive


International Drive

27 min drive


Orlando International Airport

28 min drive


coasts


Tampa (West)

1 hr + 22 min drive


Cocoa Beach (East)

1 hr + 19 min drive




Learn about investing or living in Winter Garden, Florida

Contact Us

OUR OFFICE

30 W Smith St.

Winter Garden, FL 34787

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