Oakland Park

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.  

Oakland Park Homes for Sale

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166 Hammock Preserve Loop, OAKLAND

$850,000

166 Hammock Preserve Loop, OAKLAND

4 Beds 4 Baths 3,186 SqFt Residential MLS® # O6439973
Pending
944 Kylee Aly, WINTER GARDEN

$779,900

944 Kylee Aly, WINTER GARDEN

4 Beds 4 Baths 2,831 SqFt Residential MLS® # O6425976
Open House
844 Oakland Park Boulevard, WINTER GARDEN

$1,195,000

↓ $30,000

844 Oakland Park Boulevard, WINTER GARDEN

5 Beds 4 Baths 3,525 SqFt Residential
Sat, Sep 12th, 2026 @ 10am - 1pm
MLS® # O6419976
925 Easley Avenue, WINTER GARDEN

$1,125,000

↓ $40,000

925 Easley Avenue, WINTER GARDEN

4 Beds 4 Baths 2,667 SqFt Residential MLS® # O6412977
Pending
1338 Union Club Drive, WINTER GARDEN

$890,000

↓ $10,000

1338 Union Club Drive, WINTER GARDEN

4 Beds 4 Baths 2,637 SqFt Residential MLS® # O6412710
Pending
914 Trowman Alley, WINTER GARDEN

$595,000

↓ $30,000

914 Trowman Alley, WINTER GARDEN

3 Beds 3 Baths 1,642 SqFt Residential MLS® # O6410871
Open House
1101 Eagles Pass Way, WINTER GARDEN

$1,644,999

↓ $30,000

1101 Eagles Pass Way, WINTER GARDEN

6 Beds 5 Baths 4,104 SqFt Residential MLS® # O6408835
811 Civitas Way, WINTER GARDEN

$2,175,000

↓ $24,000

811 Civitas Way, WINTER GARDEN

4 Beds 5 Baths 5,138 SqFt Residential MLS® # O6403760
Open House
907 Easley Avenue, WINTER GARDEN

$859,000

↓ $6,000

907 Easley Avenue, WINTER GARDEN

3 Beds 3 Baths 2,252 SqFt Residential
Wed, Sep 9th, 2026 @ 12:30pm - 2:30pm
MLS® # O6406147
Open House
906 Allendale Lane, WINTER GARDEN

$1,725,000

↓ $40,000

906 Allendale Lane, WINTER GARDEN

5 Beds 4 Baths 3,784 SqFt Residential
Wed, Sep 9th, 2026 @ 12:30pm - 2:30pm
MLS® # G5107489
1258 Ridge Lake Way, OAKLAND

$2,098,000

↑ $100,000

1258 Ridge Lake Way, OAKLAND

4 Beds 4 Baths 4,557 SqFt Residential MLS® # O6373776
500 9th Street Ne, FORT MEADE

$309,900

↓ $10,000

500 9th Street Ne, FORT MEADE

3 Beds 2 Baths 1,545 SqFt Residential MLS® # P4937200

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Oakland Park Real Estate Market Statistics

Average Price $1.1M
Lowest Price $595K
Highest Price $2.2M
Total Listings 38
Avg. Days On Market 195
Avg. Price/SQFT $375
List to Sell Price Percentage 98 %

Property Types (active listings)

Winter Garden Communities

 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 - 2025
HOA: Yes
Square Footage: 1,584 - 5,600+
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
  • Tucker Oaks Village - Distance: 1 mile
  • West Market - Distance: 2 miles
  • West Point Commons - Distance: 2.5 miles

Parks and Recreation

  • West Orange Trail - Distance: Direct Access within the community
  • Roper YMCA Family Center - Distance: 4.5 miles
  • Speer Park - Distance: 1 mile
  • Oakland Nature Preserve - Distance: 1.5 miles
  • Johns Lake Conservation Area - Distance: 3 miles
  • Roper YMCA - Distance: 4.5 miles
  • Newton Park - Distance: 3.5 miles
  • Veterans Memorial Park - Distance: 2 miles

Hospitals

  • Health Central Hospital - Distance: 7 miles
  • AdventHealth Winter Garden - Distance: 5 miles

*Distances are approximately measured from the Oakland Park community entrance

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