Winter Garden

Rich in Florida history this quaint, lakeside community is located just west of the city of Orlando and nestled South of Lake Apopka. Residents and visitors boast its great resurgence of historical Plant St. with its tree-lined, cobblestone streets adorned with top-rated fine dining restaurants, cafes, coffee shops, boutiques, and home to one of the South's most popular Farmer's Markets, all this along the 22-mile West Orange Trail. If retail therapy is on your to-do list you can browse the boutiques and specialty shops, or sit on a bench along the tree-lined sidewalks with your favorite coffee, tea, or ice cream treat. Residents enjoy their close proximity to Plant Street, family-oriented events, and golf cart accessibility.

Clock tower gate in Winter Garden, Florida Beautiful fountain in a courtyard in Winter Garden, Florida Farmers Market in Winter Garden, Florida Centennial Plaza gate in Winter Garden, Florida Fountain in a courtyard in Winter Garden, Florida

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0001 Tucker Oaks Boulevard, WINTER GARDEN


0001 Tucker Oaks Boulevard, WINTER GARDEN

0 Beds 0 Baths 0 SqFt Commercial MLS® # S5075843


17802 Old Ymca Road, WINTER GARDEN


17802 Old Ymca Road, WINTER GARDEN

0 Beds 0 Baths 0 SqFt Land MLS® # O5968921


13377 Lake Butler Boulevard, WINTER GARDEN


13377 Lake Butler Boulevard, WINTER GARDEN

5 Beds 5 Baths 6,210 SqFt Residential MLS® # O6100391


14401 Isleview Drive, WINTER GARDEN


14401 Isleview Drive, WINTER GARDEN

6 Beds 9 Baths 8,552 SqFt Residential MLS® # O6099409


14501 Grove Resort Avenue 1211, WINTER GARDEN


14501 Grove Resort Avenue 1211, WINTER GARDEN

30 Beds 24 Baths 1,265 SqFt Residential MLS® # O6052380


14629 Isleview Dr, WINTER GARDEN


↓ $195,000

14629 Isleview Dr, WINTER GARDEN

6 Beds 6 Baths 9,275 SqFt Residential MLS® # O6047200


12408 Walker Pond Road, WINTER GARDEN


↓ $50,000

12408 Walker Pond Road, WINTER GARDEN

9 Beds 10 Baths 10,765 SqFt Residential MLS® # O6018784


1253 East Fullers Cross Road, WINTER GARDEN


1253 East Fullers Cross Road, WINTER GARDEN

4 Beds 5 Baths 3,495 SqFt Residential MLS® # G5049866


900 West Plant Street, WINTER GARDEN


900 West Plant Street, WINTER GARDEN

7 Beds 8 Baths 7,704 SqFt Residential MLS® # O6075358


16250 West Colonial, WINTER GARDEN


↑ $600,000

16250 West Colonial, WINTER GARDEN

0 Beds 0 Baths 0 SqFt Commercial MLS® # G5014486


7827 Skiing Way, WINTER GARDEN


↓ $100,000

7827 Skiing Way, WINTER GARDEN

5 Beds 7 Baths 5,564 SqFt Residential MLS® # O6039897


130 N West Crown Point, WINTER GARDEN


↓ $327,200

130 N West Crown Point, WINTER GARDEN

0 Beds 0 Baths 0 SqFt Commercial MLS® # O5982921


About Winter Garden, Florida

Winter Garden is located 14 miles west of Downtown Orlando, in Orange County. It is located on the south shore of Lake Apopka and is bordered by the city of Ocoee to the East, Oakland to the west, and Windermere to the South. Its population is approximately 47,000, over an area of 17.9 square miles.

The city was established in 1857 and features a charmingly historical downtown core, listed on the National Registry of Historic Places. Its roots were based in citrus grove, farming, and rail travel. Its town motto is, fittingly, “A charming little city with a juicy past”.

Winter Garden is bisected by Florida State Road 50 (West Colonial Drive), separating the city into northern and southern sections. Farmland and orange groves in the south of the city have been the site of much construction, and the creation of newer neighborhoods and communities.

Not only is downtown Orlando only a 20-minute drive away via Interstate 408, but Walt Disney World is within 25 minutes (12.4 miles), and Orlando International Airport is a half-hour away (25.8 miles).

Winter Garden is popular with those seeking an active lifestyle with numerous parks including a splash pad, pavilions, fishing, and grilling. The neighborhood offers perfect opportunities for walking, biking, and jogging. Many of the historic buildings still stand, including the Winter Garden Theatre, The Central Florida Railroad Museum, and the Edgewater Hotel. 

Winter Garden Real Estate

Winter Garden is a desirable market for everyone from young professionals commuting to surrounding communities, local entrepreneurs, families, and retirees. Residents love the area’s tight-knit, small-town feel, local amenities, and proximity to Orange County employment, tourism, and entertainment opportunities.

The southern areas of town feature newer neighborhoods, as farmland and orange groves make way for newer developments. Large-scale developments like Johns Lake Pointe, Stoneybrook West, Stonecrest, Westfield, and Wintermere Pointe offer a great variety of upscale options. Neighborhoods like McAllister Landing offer resort-style amenities within the security of a gated community.

Discover beautiful homes in a variety of styles, with influences from the Mediterranean to Craftsman to Key West, with oversized living and entertaining spaces, and luxurious finishes. Many homes offer lanais for indoor/outdoor relaxation, well-appointed pool and spa spaces, and even lakefront access.

The northern areas of town, closer to the West Orange trail, feature beautiful older heavily-treed neighborhoods, with vintage homes on large lots. These unique homes are often modernly updated for the demands of today’s families while keeping their period-appropriate original details and personality.

Winter Garden also features an impressive array of lot listings, both residential and commercial. With its ideal location in West Orange County, there is outstanding potential for development.

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Winter Garden Attractions

With its thriving downtown core full of local small businesses, natural beauty, and excellent walkability, Winter Garden residents have no shortage of things to do in their own backyard. At the same time, it is close enough to Orlando to take advantage of its attractions on a whim.

The heart of Winter Garden is its quaint downtown core. The main thoroughfare, Plant Street, features many of the town’s original buildings. Many have been converted into unique cafes, eateries, boutiques, and antique shops. Some local faves include Sweet Dee’s Cupcakery, The Attic Door, The Whole Enchilada, Axum Coffee, and Winter Garden Pizza. The Plant Street Market is anchored by the Crooked Can Brewing Company and features 20 vendors offering a variety of cuisines, including organic and vegan options.

While local businesses are the backbone of this tight-knit community, Winter Garden still offers all the big-box retailers and chains one will need. Located in the south of town, Winter Garden Village offers over a million square feet of outdoor shopping, with anchor stores like Super Target, Best Buy, and Lowe’s, and national chain restaurants like Starbucks, Chili’s, Chipotle, Panera, Five Guys and more.

There’s always something going on in Winter Garden, with live music in the downtown core, car shows, weekly food truck roundups, holiday festivals, and more. The award-winning Winter Garden Farmers Market runs every Saturday rain or shine, featuring vendors with local produce, dairy products, baked goods, handcrafted jewelry, and more.

Winter Garden is also a major cultural center in West Orange County. It is home to the Central Florida Railway Museum, and numerous historical sites. The Garden Theatre, constructed in 1935, one of the original venues in central Florida to feature “talkies”, has been lovingly restored and hosts weekly live theatre and musical performances. The SoBo Gallery and Art Center host monthly rotating exhibitions, as well as all-ages workshops and kids programs year-round.

If you love the outdoors, Winter Garden is a great place to be. While the city welcomes new developments and businesses, it ensures that natural beauty is maintained. The West Orange Trail is the city’s crown jewel, as a 22-mile long paved multi-use pathway perfect for walking, running, and biking. The trail runs along the decommissioned railway path through the downtown core, through forested neighborhoods and city parks, and along the lakeshore. The Lake Apopka Wildlife Drive is another local favorite, an 11-mile trail along restored wetlands showcasing not only the landscape but over 360 bird species and other native creatures and gators.

When you are ready to relax indoors after your outdoor activities, head to the Plant Street Market! This indoor artisan market featuring food vendors and is anchored by Crooked Can Brewery Company. Open 7 days a week and also offers outdoor yoga classes, a children's area, and ample parking. Check out their holiday festival list for events throughout the year. 

With its ideal location in West Orange County, Winter Garden is close enough to all the theme parks, beaches, sporting and event venues one could need in the Orlando area. Downtown Orlando is 25 minutes (14 miles) away, and residents can access attractions like Walt Disney World, Universal Studios, and Sea World within a half hour.

Winter Garden Education

Winter Garden is a very family-friendly community, with numerous highly-rated schools. Serviced by the Orange County Public School District, many of the public schools receive A ratings, including Whispering Oak and Independence Elementary. Alternative options include charter schools like Innovation Montessori, Hope Charter, and Legacy High School.

Winter Garden is also within a half-hour drive of many of Orlando’s colleges, perfect for older students who can commute from home. These include Central University of Florida, Rollins College, Florida Technical College, and more.

Winter Garden is also within a half-hour drive of many of Orlando’s colleges, perfect for older students who can commute from home. These include Central University of Florida, Rollins College, Florida Technical College, and more.


What is Winter Garden known for?

Winter Garden is known for its vibrant culture and ‘Old Florida’ charm. It has many historical buildings and museums, as well as arts venues and community events such as the Winter Garden Farmers market. It attracts people from all walks of life thanks to its safe subdivisions, easy-going atmosphere and close proximity to nature trails and green spaces.

How far is Winter Garden from Orlando?

Winter Garden is just a 26-minute drive to Orlando, making it a prime destination for those who want to be close to a major urban center, but in a much more peaceful environment. 

What is the closest beach to Winter Garden?

The closest beaches to Winter Garden are New Smyrna Beach and Cocoa Beach on the Atlantic Coast. Both are about an hour and 20-minute drive from Winter Garden.

What are housing prices like in Winter Garden?

The median home price in Winter Garden is $420,000. However, you can find homes to fit all budgets here including luxury estates, spacious single-family homes, condos, duplexes and homes for rent. 

Does Winter Garden get hurricanes?

Winter Garden is located in Central Florida about 65 miles from the Atlantic Coast, so it is a very low-risk area for hurricanes. Residents may experience rain and wind from time to time, but hurricanes very rarely cause damage in the community.

Is Winter Garden a good place to invest in real estate?

There are many reasons why Winter Garden is a great place to invest in real estate. The community has seen consistent growth over the past two decades, and people continue to seek out houses for sale here thanks to the great weather, laid-back atmosphere and excellent amenities. Home values have seen significant increases over the past few years and there are good reasons to believe that this trend will continue in the future.

Winter Garden Real Estate Stats

Average Home Price $453K
Lowest Listing Price $0
Highest Listing Price $4.3B
Total Property Listings 486,849
Avg. Days On Market 188
Avg. Price/SQFT $258

Property Types (active listings)

Kari Fleck, Owner & Broker

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