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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

13 Properties Found. Page 1 of 1.
Photo of Listing #O6070974

708 Lake Brim Drive

MLS® # O6070974
5 Beds, 5 Baths, 3,339 Sf
Photo of Listing #O6060907
Reduced 2.1%

942 Densdale Lane

MLS® # O6060907
5 Beds, 4 Baths, 3,307 Sf
Photo of Listing #T3413806
MLS® # T3413806
5 Beds, 4 Baths, 2,985 Sf
Photo of Listing #G5061537
Reduced 5.3%
MLS® # G5061537
5 Beds, 4 Baths, 2,856 Sf
Photo of Listing #O6063906

1212 Civitas Way

MLS® # O6063906
3 Beds, 2 Baths, 2,219 Sf
Photo of Listing #O6045919
MLS® # O6045919
3 Beds, 3 Baths, 2,254 Sf
Photo of Listing #T3393958
MLS® # T3393958
4 Beds, 4 Baths, 2,822 Sf
Photo of Listing #T3390476
MLS® # T3390476
4 Beds, 4 Baths, 2,717 Sf
Photo of Listing #O6054221
Reduced 1.4%

927 Colie Alley

MLS® # O6054221
4 Beds, 4 Baths, 2,719 Sf
Photo of Listing #T3390451
MLS® # T3390451
3 Beds, 3 Baths, 2,333 Sf
Photo of Listing #T3390466
Reduced 4.9%
MLS® # T3390466
3 Beds, 3 Baths, 1,929 Sf
Photo of Listing #T3414417
MLS® # T3414417
3 Beds, 3 Baths, 1,584 Sf
Photo of Listing #T3400882
MLS® # T3400882
3 Beds, 3 Baths, 1,652 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 November 29th, 2022 at 3:03am EST.