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Oakland Trails Winter Garden

Oakland Trails is a neighborhood of single-family residential homes located in Oakland, a small community on the edge of Winter Garden. This neighborhood is perfectly situated south of Florida’s third largest lake, the 30,000-acre Lake Apopka, and just north of Johns Lake. On the border of Orange and Lake County, Oakland Trails residents have direct access to the 22-mile West Orange Trail. The Town of Oakland is about 16 miles west of Downtown Orlando and an ideal location for getting to nearby shopping and entertainment, and for commuting to Orlando’s famous theme parks including Walt Disney World Resorts and Universal Orlando.

Oakland Trails Homes For Sale

8 Properties Found. Page 1 of 1.
Photo of Listing #G5076776
Reduced 1.9%
MLS® # G5076776
5 Beds, 3 Baths, 3,416 Sf
Photo of Listing #S5105743
MLS® # S5105743
5 Beds, 4 Baths, 3,248 Sf
Photo of Listing #O6202301
Reduced 1.9%
MLS® # O6202301
4 Beds, 3 Baths, 2,418 Sf
Photo of Listing #O6200569
Reduced 0.4%
MLS® # O6200569
3 Beds, 3 Baths, 2,082 Sf
Photo of Listing #O6205390
MLS® # O6205390
3 Beds, 3 Baths, 2,082 Sf
Photo of Listing #O6210225
Reduced 0.6%
MLS® # O6210225
3 Beds, 3 Baths, 1,904 Sf
Photo of Listing #O6199481
Reduced 1.1%
MLS® # O6199481
3 Beds, 3 Baths, 1,904 Sf
Photo of Listing #O6209273
Reduced 3.4%
MLS® # O6209273
3 Beds, 3 Baths, 1,663 Sf


Oakland Trails, a neighborhood that will ultimately consist of about 305 single-family homes, is located on the shores of Florida’s third largest lake, Lake Apopka. Homeowners at Oakland Trails enjoy that Killarney Station, a stop on the West Orange Trail with picnic areas and a children’s playground, is within walking distance of the neighborhood entrance. With it’s moss-draped oak trees, Oakland is a quaint town known for its proximity to both Johns Lake and Lake Apopka, in addition being directly connected to Winter Garden’s Historic Downtown by the West Orange Trail.

Homes with in Oakland Trails range from three and five bedrooms and from two to four bathrooms. Houses are one or two stories and each has a two-car garage.
This neighborhood is positioned near Winter Garden’s historic downtown that features boutique shops, locally owned restaurants, coffeehouses, the refurbished Garden Theatre and more. Additionally, homeowners appreciate being just a short drive from the Winter Garden Village that encompasses a Super Target, several clothing stores and many chain restaurants.

Oakland Trails Amenities

Homeowners at Oakland Trails enjoy access to a number of neighborhood amenities that are maintained by the homeowners association including a community clubhouse, a swimming pool, a dog park and a children’s playground.

Oakland Trails Community Information

Location: Florida’s Turnpike and West Colonial Drive
Year Built: 2017 - Present
Total Properties: 305
Builder: Meritage Homes
Square Feet: 1,641 - 3,446
HOA: Yes
Community Amenities: clubhouse, dog park, swimming pool, children’s playground, outdoor recreation space.

Orange County Area Schools

  • Tildenville Elementary: Grades Pre-K - 5th Distance: 2.7 miles
  • Lakeview Middle School: Grades 6th - 8th Distance: 3.1 miles
  • West Orange High School: Grades 9th - 12th Distance: 5.0 miles
  • Oakland Avenue Charter School: Grades Kindergarten - 5th Distance: 1.7 miles

Dining and Shopping

  • East Towne Center, Publix Super Market - Distance: 1.7 miles
  • Winter Garden Village Retail Shopping Center with Super Target - Distance: 4.2 miles
  • Historic Downtown Winter Garden - Distance: 4.0 miles
  • The Mall at Millenia, Retail Shopping Centers, & BJ's Wholesale Club - Distance: 13.7 miles
  • Downtown Orlando - Distance: 16.0 miles

Parks and Recreation

  • West Orange Trail - Distance: 0.06 miles
  • Johns Lake Public Boat Ramp - Distance: 0.4 miles
  • Oakland Nature Reserve, Hiking Trails, Wildlife Viewing - Distance: 0.8 miles
  • Newton Park, Lakefront Playground, Fishing, Picnic Area - Distance: 4.3 miles
  • South Lake YMCA - Distance 4.4 miles


  • Florida Hospital Winter Garden - Distance: 4.0 miles
  • Health Central Hospital - Distance: 7.4 miles

*Distances are approximately measured from JW Jones Road and Florida State Road 438.


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 independently 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.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on June 20th, 2024 at 5:50pm EDT.