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Winter Garden FL


Looking to explore or settle in Winter Garden FL? This guide cuts straight to the heart of what you need to know. From its historic charm to outdoor adventures and the vibrant food scene, discover what makes Winter Garden a beloved part of West Orange County.

Winter Garden Florida Highlights

  • The City of Winter Garden FL is a city with a rich history tied to the citrus industry and has a well-preserved historic downtown area that reflects its vibrant past, including influences from the railroads and prominent figures in citrus farming.

  • Downtown Winter Garden offers a lively mix of shopping, dining, and entertainment, with unique attractions like the Plant Street market area for tourists and residents. The Winter Garden Village is awesome and the weekly Farmers Market feature local produce, vendors and live music once a week.

  • The city also provides ample outdoor recreational opportunities at attractions like Lake Apopka and the West Orange Trail, along with a thriving arts scene represented by the Garden Theatre and local museums, and is conveniently located near major Central Florida attractions.

A Glimpse into Winter Garden's Past

Historical downtown area of The City of Winter GardenLocated in the heart of West Orange County, Winter Garden’s history is as vibrant and diverse as the city itself. During its formative years, Winter Garden flourished as a focal point for Florida’s citrus industry. The city’s growth was greatly influenced by the expansion of rail travel, which significantly contributed to the development of the citrus trade. From sugar cane and vegetables during the Civil War to the bustling citrus, turpentine, and lumber industries facilitated by the arrival of the Orange Belt Railroad. Winter Garden’s history is a rich tapestry woven with threads of resilience, innovation, and progress.

Winter Garden consistently enchants visitors with its rich history and natural marvels to this day. The historic downtown area, teeming with preserved historical buildings and scenic vistas (good things), offers a glimpse into the city’s past while serving as the perfect destination for a leisurely stroll or a day of exploration. So, whether you’re a history enthusiast or a casual visitor, Winter Garden’s storied past promises a journey rich in discovery and charm.

See The Homes For Sale in Winter Garden FL

Former Citrus Town

Winter Garden’s vibrant history prominently features its illustrious era as a booming citrus town. The town established itself in citrus and vegetable farming by the end of the nineteenth century and emerged as the area’s primary cash crop, sparking rapid expansion and development as a commercial center. Prominent figures like Phillip Christian Peters and Jerry J. Chicone Jr. played significant roles in the growth of the industry.

Despite the decline of the citrus industry, due to the damaging freezes of the 1980s and Heller Bros. Packing Corp. stopping citrus production in 1939, its influence on Winter Garden’s cultural identity persists. The industry, deeply intertwined with the local culture, was more than just an economic force. It shaped the town’s history, provided employment opportunities, and became a symbol of Winter Garden’s heritage.

Now, this erstwhile citrus town still revels in its ‘juicy past’ and the lasting influence of its citrus heritage.

Historic Downtown

Entering Winter Garden’s historic downtown feels akin to journeying back in time. Located in Winter Garden FL 34787, this area is a testament to the city’s commitment to preserving its past. From historic buildings to landmarks like Tony’s Liquors and the Dillard & Boyd Building, every corner tells a story of the city’s rich past.

Efforts to preserve and revitalize the area have seen the repurposing of buildings, the adoption of a downtown design overlay, and the meticulous work of the Winter Garden Heritage Foundation. The result? A charming little city that not only offers a glimpse into the city’s past but also serves as a living, breathing testament to its historical and natural assets.

And with its position along the acclaimed West Orange Trail and its designation on the National Registry of Historic Places, the historic downtown area continues to provide an immersive cultural experience for all who visit.

Discovering Downtown Winter Garden

Vibrant atmosphere of Plant Street in Winter GardenTransitioning from the past into the present reveals downtown Winter Garden as a lively blend of tradition and modernity. This area serves as a cultural hub, offering a diverse range of shopping, dining, and cultural experiences. Whether you’re in the mood for some retail therapy, eager to savor local flavors, or simply looking to soak in the city’s culture, downtown Winter Garden has something for everyone.

Within the historic district, quaint shops and cafés rub shoulders with vibrant restaurants, each offering a unique slice of Winter Garden. And just a stone’s throw away is Winter Garden Village, where you can find chain establishments and an assortment of retail options. From one-of-a-kind boutiques to nationally recognized stores, the shopping experience in downtown Winter Garden is as diverse as it is captivating.

Plant Street Winter Garden

Plant Street undoubtedly stands out as a highlight in downtown Winter Garden. Known for its unique shops and restaurants, this street is a microcosm of the city’s charm and vibrancy. Whether you’re in the mood for some retail therapy or a gastronomical adventure, Plant Street has you covered.

If you’re a fan of live music, be sure to check out Fridays on the Plaza, a recurring series of complimentary live music gatherings held every Friday evening on Plant Street. And for craft beer enthusiasts, a visit to the highly regarded Crooked Can Brewing Company is a must. With its diverse offerings and vibrant ambiance, Plant Street truly embodies the spirit of Winter Garden.

Winter Garden Village

Located just a brief drive away from downtown Winter Garden, the Winter Garden Village is a thriving shopping spot that boasts a distinct mix of local allure and prominent retailers. Home to over 80 diverse shops and restaurants, this place is a shopper’s paradise.

But shopping isn’t all that Winter Garden Village has to offer. The local businesses contribute to its unique charm, encompassing a variety of options such as:

  • America’s Best

  • AT&T

  • Adjectives Market

  • and many more

Whether you’re looking for a quick bite, a leisurely brunch, or a shopping spree, Winter Garden Village has got you covered.

Winter Garden Farmers Market: A Local Treasure

A visit to the Winter Garden Farmers Market is essential for those seeking to savor the local flavor of Winter Garden. Held every Saturday at the Downtown Pavilion, this market offers:

  • A wide array of fresh produce

  • Live music

  • Entertainment for visitors to enjoy

  • Locally grown produce

  • Homemade soaps

  • Artisan creations

The market offers a plethora of options to choose from.

As you navigate through the bustling market, the sound of live music fills the air, adding to the lively atmosphere. Take a moment to soak in the scene - the vibrant colors of fresh produce, fresh flowers, the enticing aroma of baked goods, and the rhythmic beat of music. It’s not just a market; it’s a celebration of the local community and a testament to Winter Garden’s vibrant spirit.

Live Music and Entertainment

One of the highlights of the Winter Garden Farmers Market is its live music. Showcasing local talent, the market features live music every Saturday from 9:00 am to 1:00 pm, and also every Friday night on the Plaza. As the music fills the air, it brings the market to life, adding a dash of vibrancy and excitement to the shopping experience.

But the music isn’t just for background entertainment. It’s a platform for local artists to showcase their talent and for the community to come together and celebrate their shared love for music. Whether it’s the lively beats of a local band or the soulful strains of a solo artist, the music at the Winter Garden Farmers Market is sure to leave you tapping your feet and humming along.

Exploring the Great Outdoors in Winter Garden

Scenic view of Lake Apopka in Winter GardenWinter Garden has an abundance to offer for those who are enthusiastic about nature. From the serene beauty of Lake Apopka to the scenic West Orange Trail, the city offers numerous outdoor attractions that promise to awaken your love for nature. Whether you’re a seasoned adventurer or a casual explorer, the great outdoors of Winter Garden are sure to captivate your senses.

Lake Apopka, one of Florida’s largest lakes, is the centerpiece of Winter Garden’s outdoor attractions. Offering opportunities for birdwatching, fishing, and boating, Lake Apopka is a haven for nature lovers. And if you’re in the mood for a leisurely stroll or a bike ride, the West Orange Trail, with its picturesque views and diverse landscapes, is perfect for you.

Beautiful Lake Apopka

Lake Apopka, with its diverse range of outdoor activities and serene surroundings, is one of Winter Garden’s prime outdoor attractions. Some of the activities you can enjoy at Lake Apopka include:

  • Fishing

  • Hiking

  • Birdwatching

  • Canoeing

  • Camping

Once known for its premier bass fishery, Lake Apopka today is a popular destination for outdoor enthusiasts.

But Lake Apopka isn’t just about outdoor activities. The lake holds historical significance as the initial settlement of Winter Garden began in the 1850s, with settlers drawn to the fertile muck land surrounding the lake. Today, Lake Apopka continues to play a crucial role in the region’s geography, with the lowest elevation in Winter Garden measuring 64 feet near the lake.

West Orange Trail

Another unmissable outdoor treasure in Winter Garden is the West Orange Trail. Completed in 1999, this paved trail spans downtown Oakland, Winter Garden, and Apopka, providing a recreational pathway for biking, walking, and jogging.

Apart from being a recreational trail, the West Orange Trail also serves as a connector, linking small communities and suburban neighborhoods along its route. Whether you’re a fitness enthusiast looking for a scenic running route or a casual explorer in search of stunning landscapes, the West Orange Trail promises an experience like no other.

Arts and Culture in Winter Garden

Historic Garden Theatre in Winter GardenA thriving arts and culture scene is nestled among Winter Garden’s natural splendors and historical allure. At the heart of this cultural landscape lies the Garden Theatre, a historic venue offering a diverse range of performances and community events. Alongside the theatre, the city is also home to two museums - the Winter Garden Heritage Museum and the Central Florida Railroad Museum - which offer a captivating glimpse into the city’s history and heritage.

Whether you’re a theatre enthusiast looking for a riveting performance, a history buff keen to explore the city’s past, or a casual visitor seeking a cultural experience, Winter Garden’s arts and culture scene offers something for everyone.

Garden Theatre

The Garden Theatre, a cornerstone of Winter Garden’s arts and culture scene, is a place where history and artistry come together. Originally inaugurated in December 1935, the theatre was the first in Central Florida specifically constructed for ‘talkies’. Its architectural design in the Mediterranean Revival style and the interior, inspired by a Spanish courtyard, offer a distinctive and immersive ambiance for patrons.

Today, the Garden Theatre continues to captivate audiences with its diverse roster of performances. From live musical acts like Gary Roland & The Landsharks to film screenings like ‘The Goonies’, the theatre offers a rich selection of entertainment options that cater to a variety of tastes.

Two Museums to Visit

For those interested in delving into Winter Garden’s history, the city is home to two museums - the Central Florida Railroad Museum and the Winter Garden Heritage Museum. These establishments play a crucial role in preserving the city’s history, offering fascinating insights into the past of West Orange County.

The Winter Garden Heritage Museum, with its rotating exhibits, provides visitors with an opportunity to explore the diverse history of West Orange County, from its early settlers to its citrus-laden past. On the other hand, The Central Florida Railroad Museum focuses on the history of railroading in Central Florida, paying tribute to the industry that played a significant role in the city’s growth.

Dining Delights: Award-Winning Restaurants and Local Favorites

Nothing matches the satisfaction of a delectable meal after a day filled with exploration and discovery. And when it comes to dining, Winter Garden does not disappoint. The city boasts a vibrant dining scene, featuring award-winning restaurants and local favorites that promise to satisfy your culinary cravings.

From the upscale Chef’s Table at the Edgewater to the comfort food at 4 Rivers Smokehouse, the city’s restaurants offer a diverse range of cuisines, each with their own unique twist. Whether you’re a foodie in search of a gourmet experience or a casual diner looking for a cozy café, Winter Garden’s dining scene has got you covered.

Plant St Dining Options

Plant Street, the heart of Winter Garden’s culinary scene, is a haven for food lovers. With a diverse range of dining options, this street serves up a culinary adventure like no other.

Whether you’re in the mood for a hearty American breakfast, a spicy Thai curry, or a refreshing scoop of ice cream, Plant Street has it all. Each restaurant and café on the street offers a unique dining experience, ensuring that every meal is a memorable one.

Winter Park Dining Scene

Just a stone’s throw away from Winter Garden is Winter Park, another culinary hotspot in Central Florida. Known for its diverse selection of restaurants and cuisines, this dining scene is a food lover’s paradise. Which is better?

Winter Park offers a culinary journey that spans the globe. Whether you’re in the mood for:

  • Michelin-starred restaurants like Swine & Sons

  • Local favorites like Ethos Vegan Kitchen

  • A Mediterranean feast

  • A Greek delicacy

  • An American classic

  • A Mexican fiesta

Winter Park’s dining scene has something to suit every palate.

Convenient Access to Central Florida Attractions

Although Winter Garden has ample attractions of its own, its strategic location renders it an ideal base for venturing into the broader Central Florida region. The city’s close proximity to Orlando and the major theme parks offers a world of entertainment options and attractions just a short drive away.

Whether you’re looking to experience the magic of:

  • Walt Disney World

  • Universal Studios

  • SeaWorld

  • the vibrant city life of Orlando

Winter Garden puts you in the perfect spot to access all these attractions and more.

So why wait? Start planning your Winter Garden adventure today!

Proximity to Orlando

Orlando, celebrated for its vibrant nightlife, bustling shopping districts, and top-tier attractions, is a mere 22-minute car ride away from Winter Garden. From the iconic Cinderella Castle at Walt Disney World to the thrilling rides at Universal Studios, Orlando is a city where dreams come to life.

And with numerous modes of transportation available, including buses, taxis, and shuttles, getting from Winter Garden to Orlando is a breeze. So if you’re looking to add a dash of city life to your Winter Garden adventure, Orlando is just a short ride away.

Theme Parks and More

Winter Garden’s closeness to Florida’s premier theme parks is a dream come true for those who seek thrills and adventures. Whether you’re looking to meet your favorite Disney characters, experience the magic of Hogwarts at Universal Studios, or marvel at the underwater wonders at SeaWorld, these attractions are just a short drive away.

With its convenient location, Winter Garden serves as the perfect base to explore these attractions. So why limit your adventure to just one city? With Winter Garden as your starting point, the whole of Central Florida is yours to explore.


As we come to the end of our journey, it’s clear that Winter Garden is more than just a city. It’s a vibrant tapestry of history, culture, nature, and gastronomy. Whether you’re a history buff, a food lover, an outdoor enthusiast, or a culture vulture, Winter Garden has something for you.

With its rich history, thriving arts scene, diverse dining options, and convenient location, Winter Garden isn’t just a great place to visit - it’s a great place to live, work, and play. So why wait? Come and discover the charm of Winter Garden Florida.

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independent verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. The source of the listing data is as follows: Stellar MLS (updated 6/22/24 2:18 PM) |
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Contact Wendy Morris


Wendy Morris LLC
DBA Wendy Morris Realty
Licensed in the State of Florida
BK 3146762
16797 Broadwater Avenue
Winter Garden, Florida 34787

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