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Oakland Park Real Estate

Oakland Park is located in Winter Garden along the shores of Lake Brim and Lake Apopka. The community consists of 258 acres of homes with shady front porches and street lined with Live Oaks. Inspired by small towns from the early twentieth century Oakland Park brings the beauty of Old Florida nature and architectural charm. Oakland Park residents enjoy a natural Florida setting with open play fields, playgrounds, and a community pool. The community has direct access to the West Orange Trail connecting residents to 22 miles of preserved trails to enjoy biking, running, or a leisurely stroll to downtown Winter Garden.  

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Oakland Park Homes for Sale

11 Properties Found. Page 1 of 1.
Photo of Listing #O6219748
Reduced 2.8%
MLS® # O6219748
4 Beds, 4 Baths, 3,589 Sf
Photo of Listing #O6224418
MLS® # O6224418
5 Beds, 4 Baths, 3,803 Sf
Photo of Listing #O6216860

897 Landrum Drive

MLS® # O6216860
4 Beds, 4 Baths, 3,012 Sf
Photo of Listing #O6218297

931 Kylee Alley

MLS® # O6218297
4 Beds, 4 Baths, 2,831 Sf
Photo of Listing #O6214760
MLS® # O6214760
3 Beds, 3 Baths, 2,585 Sf
Photo of Listing #O6219373
Reduced 1.1%
MLS® # O6219373
5 Beds, 4 Baths, 3,084 Sf
Photo of Listing #O6217570
MLS® # O6217570
3 Beds, 3 Baths, 2,260 Sf
Photo of Listing #O6213614
MLS® # O6213614
4 Beds, 3 Baths, 2,240 Sf
Photo of Listing #O6201286
Reduced 3.3%
MLS® # O6201286
4 Beds, 3 Baths, 2,509 Sf
Photo of Listing #O6212096
Reduced 5.7%
MLS® # O6212096
3 Beds, 3 Baths, 2,421 Sf
Photo of Listing #O6207877
MLS® # O6207877
4 Beds, 4 Baths, 2,219 Sf

 Oakland Park - Cottage Series

Oakland Park was developed by Crescent Communities LLC and homes built by Ashton Woods, David Weekly, and J & J Building the community offers a variety of sized homes and architectural styles. Architectural styles in the community include Colonial Revival, Victorian, Craftsman, Spanish Colonial and Florida Vernacular.  All homes in the Oakland Park community are built to conform to FGBC Green certification standards.

Oakland Park Community Information

Location: Oakland Park Boulevard & East Oakland Avenue, North of W. Colonial Dr (HWY 50)
Surrounding Lakes:
 Lake Brim & Lake Apopka
Year(s) Built: 2008 - New Homesites Available
HOA Fee's: $1,200 per year *subject to change

Square Footage: 1,800 - 3,700
Community Amenities: Community Pool, Cabanas, Fitness Center, Playground, Direct Access to the West Orange Trail, Picnic Areas

Orange County Public Schools

  • Tildenville Elementary: Grades Pre-K - 5th  Distance: .5 mile 
  • Lakeview Middle School: Grades 6th - 8th  Distance: 2 miles
  • West Orange High School: Grades 9th - 12th  Distance: 4 miles

Dining and Shopping

  • Downtown Winter Garden: 2 miles
  • Restaurant Row Orlando - Distance: 17 miles
  • Winter Garden Village Retail Shopping Center with Super Target - Distance: 4 miles
  • Downtown Orlando - Distance: 16 miles

Parks and Recreation

  • West Orange Trail - Distance: Direct Access within the community
  • Roper YMCA Family Center - Distance: 4.5 miles


  • Health Central Hospital - Distance: 7 miles

*Distances are approximately measured from the Oakland Park community entrance

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 July 22nd, 2024 at 7:04am EDT.