Winter Garden

Welcome to Winter Garden

This highly desirable small town is blossoming with new developments, the perfect match for its strong traditions and history.

Pressed against the quiet southern shores of Lake Apopka, the city of Winter Garden radiates with an enchanting nostalgia. The city just 14 miles northwest of Orlando is well-known for its Old-Florida feeling, solidified by its historic Downtown district and an innate commitment to the preservation of heritage.

The city, which first began drawing settlers in the 1850s, has felt set apart from the busier Orlando suburbs throughout its history, due in part to its location on the outer limits of Orange County. However, in recent years, Winter Garden has experienced a rejuvenation and growth, creating a Downtown area rich in new developments and home builders. While the peaceful ambiance remains, Winter Garden is a city on the rise.

Winter Garden is saturated in enviable, custom-home communities, and the recent surge in builds means that buyers can choose from a vast range of styles and pricing. From million-dollar farmhouses still in progress to executive homes, single-family abodes built within the last five to ten years, and affordable lakefront properties, the city is one of Central Florida’s hottest real estate markets.

What to Love

  • Golfing at Orange County National, a famous golf course with the biggest driving range in America
  • Still under 40 minutes to Downtown Orlando
  • An impressive number of shops and eateries

Local Lifestyle

Winter Garden retains what some of the suburbs in the greater Orlando area have lost — a vibrant old-world feel in which community is put first, local events reign supreme, and historic preservation is a top priority. Residents can feel perfectly at home, even when shopping for the latest fashion finds or lounging by the lake.

Dining, Entertainment, Shopping

When it comes to name-brand goods and upscale chain restaurants, locals know to visit the Winter Garden Village, an open-air shopping center with more than 80 retailers such as Nike and Bath & Body Works. Niche boutiques, curated goods, art galleries, and museums can all be found centered in Historic Downtown Winter Garden.

Many of Winter Garden’s finest restaurants call Downtown home, particularly along the stretch of West Plant Street. Here, local favorites like Axum Coffee beckon, wafting out the enticing aroma of their own special roasts with each swing of the door. Axum Coffee enriches the community through service and donations, embodying the giving culture of Winter Garden perfectly.

Also on West Plant Street, Market to Table creates masterful New American fare and innovative cocktails in its historic venue ideally situated next to The Garden Theatre. A hip and trendy atmosphere accentuates the creative Mexican fare at The Whole Enchilada, where the dedication to using only the freshest ingredients can be tasted in every bite.

Things to Do

Downtown Winter Garden is a mecca for local activity, and residents can partake in everything from annual festivals and events to invigorating local spaces like the Plant Street Market. More than 20 vendors take up shop at this community market, specializing in organic, locally-grown produce and meats as well as handmade goods.
A West Plant Street landmark, The Garden Theatre has been running shows since its restoration in 2008. The theatre was built as a single-screen cinema in 1935, and now has a calendar of more than 200 performances a year. Along West Garden Avenue, Tanner Hall is a favored choice for hosting events — ranging from corporate to wedding — due to its spacious main hall, kitchen facilities, and picturesque gazebo for outdoor ceremonies.

Just six miles from Orlando’s hottest parks including Disney World and Universal Studios, The Grove Resort is a part water park and part 4-star hotel masterpiece. An ultimate retreat for family-friendly fun, the park has a 695-foot lazy river, a surf simulator, and plenty of action-packed slides.


Winter Garden is home to a number of excellent schools. Top educational opportunities include:

  • Foundation Academy, PK & K-12, highly regarded private education institution
  • West Orange High School, 9-12, highly rated public high school among the top in the Orlando area
  • Whispering Oak Elementary, PK & K-5, highly rated public elementary school


Work With Us

The Tate Advisory Group is ready and willing to assist you with all of your real estate needs. Contact us today to get started with your home buying or selling process!

Tate Advisory Group




(407) 476-8855



The Tate Advisory Group is a team of real estate agents affiliated with Compass. Compass Florida, LLC d/b/a Compass is a licensed real estate broker and abides by equal housing opportunity laws. All material presented herein is intended for informational purposes only. Information is compiled from sources deemed reliable but is subject to errors, omissions, changes in price, condition, sale, or withdrawal without notice. No statement is made as to accuracy of any description. All measurements and square footages are approximate. This is not intended to solicit propertyalready listed. Nothing herein shall be construed as legal, accounting or other professional advice outside the realm of real estate brokerage.

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