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Oakland Park Homes for Sale

1091 Eaglecrest Drive, Winter Garden image
1091 Eaglecrest Drive, Winter Garden $1,850,000

Under Construction. Homeowner is offering this brand new Oakland Park custom home under construction for sale. This 4340 SF J&J Building home is a traditional front porch...

  • 5 Beds
  • 4.5 Baths
  • Oakland Park Unit 6b-2 SubDv.
  • 34787 Zip Code
760 Lake Brim Drive, Winter Garden image
760 Lake Brim Drive, Winter Garden $879,900 ▼

OAKLAND PARK, one of the most highly sought after neighborhoods in Winter Garden! Hop on your GOLF CART or bike and cruise into downtown where you can enjoy outdoor dini...

  • 3 Beds
  • 2.5 Baths
  • Oakland Park SubDv.
  • 34787 Zip Code
613 Cheekwood Alley, Oakland image
613 Cheekwood Alley, Oakland $820,000

Prepare to be impressed with this NEWLY built PARK-FRONT home with partial WATER views! The Sunset model is a neighborhood favorite for its oversized kitchen and spaciou...

  • 4 Beds
  • 2.5 Baths
  • Oakland Park SubDv.
  • 34787 Zip Code
1036 Kershaw Drive, Winter Garden image
1036 Kershaw Drive, Winter Garden $799,900

4 bed 2.5 bath David Weekly home in the sought after parade of homes community of Oakland Park. Just steps away from the Resort style Community Pool, clubhouse and Trail....

  • 4 Beds
  • 2.5 Baths
  • Oakland Park SubDv.
  • 34787 Zip Code
1087 Huntspoint Street, Winter Garden image
1087 Huntspoint Street, Winter Garden $795,900

RARE OPPORTUNITY! THE ONLY SINGLE STORY HOME AVAILABLE IN THE HIGHLY DESIRED COMMUNITY OF OAKLAND PARK, JUST A GOLF CART RIDE FROM DOWNTOWN WINTER GARDEN OR STEPS FROM T...

  • 3 Beds
  • 2 Baths
  • Oakland Parka SubDv.
  • 34787 Zip Code
1061 Sadler Oaks Way, Winter Garden image
1061 Sadler Oaks Way, Winter Garden $789,900

Under Construction. Welcome to the charming, storybook community of Oakland Park! This Florida Vernacular home features stunning structural upgrades, including 8' doors...

  • 4 Beds
  • 3 Baths
  • Oakland Park SubDv.
  • 34787 Zip Code
947 Honeywood Alley, Winter Garden image
947 Honeywood Alley, Winter Garden $785,000 ▼

ENJOY THIS SUMMER IN YOUR NEW HOME! Oakland Park is the perfect blend of old Florida’s nature and architectural charm. No matter where you are, you are not far from a p...

  • 3 Beds
  • 2.5 Baths
  • Oakland Park SubDv.
  • 34787 Zip Code
973 Tilden Oaks Trail, Winter Garden image
973 Tilden Oaks Trail, Winter Garden $775,000 ▼

Your search is over! This gorgeous home is equipped with a large, open concept 1st floor. The gourmet kitchen boasts stainless steel appliances and a large island. St...

  • 3 Beds
  • 2.5 Baths
  • Oakland Park SubDv.
  • 34787 Zip Code

Winter Garden › Oakland Park

Oakland Park - Winter Garden

Oakland Park is a Winter Garden neighborhood of non-gated, Single Family Homes off Tildenville School Road & Oakland Ave just North of Hwy 50 in the Northwest section of Winter Garden. The majority of the homes in Oakland Park were built 2012-2019 by David Weekley Homes, Ashton Woods, Dream Finders Homes, J&J Building and various other builders.

The The West Orange Trail is nearby as is an entrance to Hwy 50/Colonial Drive which will take you East to the Florida Turnpike, the 429 Expressway and Downtown Orlando or West to Clermont.

Oakland Park Neighborhood Amenities

There is a mandatory HOA for Oakland Park which includes the following amenities:

  • Golf Carts Allowed
  • Park
  • Playground
  • Pool
  • Sidewalks
  • Waterfront
  • Clubhouse
  • Fitness Center
  • Recreation Facilities
  • Fishing

Where is Oakland Park in Winter Garden?

Oakland Park is located in the 34787 zip code in the Western Oakland area of Winter Garden.

The Oakland Park neighborhood is bordered by Lake Apopka to the North, the Oakland Hills neighborhood to the South, the Lakeview Reserve neighborhood to the East, and vacant land to the West.

What's Around & Near Oakland Park?

  • Grocery-Restaurants: West Point Commons
  • Mall: Winter Garden Village
  • Hospital: Orlando Health
  • Schools: Orange County Find My School
  • Attractions: Walt Disney World & Universal Studios
  • Get Out & Play: The West Orange Trail
  • Local Hang Out: Downtown Winter Garden
  • Closest Beach: Cocoa Beach

Typical Oakland Park Home Features

Oakland Park included home features below are common but may vary from home to home:

  • Builder(s): David Weekley Homes - Ashton Woods Homes
  • Architectural Style(s): Craftsman, Florida, Cape Cod, Key West, Bungalow, Colonial and Traditional
  • Number of Bedrooms:3-5
  • Number of Garage Spaces: 2-3
  • Sq Ft Size under Air: Approx 1900-3600
  • Interior Rooms: Attic, Den/Library/Office, Family Room, Formal Dining Room Separate, Formal Living Room Separate, Inside Utility
  • Average Lot Size: zero lot line to quarter acre
  • Construction Material: Metal, and Shingle
  • Roof: Metal, and Shingle
  • Exterior Features: Fenced, Irrigation System, Outdoor Grill, Outdoor Kitchen, Rain Gutters, Sidewalk and some homes offer park, garden or water views.

Schedule your viewing of Oakland Park today!

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Address Search

Realtor David MyersDavid Myers 407-801-3286
Your Winter Garden Real Estate Expert

Winter Garden Areas

  • Downtown Winter Garden
  • Horizon West
  • Oakland
  • Winter Garden Village

Downtown Winter Garden Area Neighborhoods

  • Downtown Winter Garden
  • Brandy Creek
  • Chapin Station
  • Courtlea Oaks
  • Courtlea Park
  • Covington Chase
  • Crown Point Springs
  • Daniels Crossing
  • Fullers Crossing
  • Fullers Landing
  • Heritage at Plant Street
  • Island Pointe
  • Kings Bay
  • Lake Cove Pointe
  • Lakeview Reserve
  • Magnolia Wood
  • McAllister Landing
  • Oakglen Estates
  • Oaks at Brandy Lake
  • Park Place
  • Regal Pointe
  • Stanton Estates
  • Sterling Pointe
  • Timbercreek Pines
  • Traditions
  • Trails of Winter Garden
  • Tuscany
  • Walkers Grove
  • Winter Oaks

Winter Garden Village Area Neighborhoods

  • Alexander Ridge
  • Amberleigh
  • Avalon Reserve
  • Avalon Ridge (NEW)
  • Banana Bay Estates
  • Bay Isle
  • Belle Meade
  • Black Lake Park
  • Black Lake Preserve
  • Bradford Creek
  • Bronsons Landing
  • Canopy Oaks
  • Carriage Pointe
  • Cobblestone
  • Country Lakes
  • Cypress Reserve
  • Daniels Landing
  • Deerfield Place
  • Emerald Ridge
  • Foxcrest
  • Glynwood
  • Grove Park
  • Grovehurst
  • Hickory Hammock
  • Johns Lake Pointe
  • Lake Roberts Landing
  • Orange Cove
  • The Orchard
  • Oxford Chase
  • Regency Oaks
  • Reserve at Carriage Pointe
  • Roper Reserve
  • Sanctuary at Twin Waters
  • Southern Pines
  • Stone Creek
  • Stoneybrook West
  • Sunset Lakes
  • Tilden Place
  • Twinwaters
  • Waterside
  • Westfield Lakes
  • Windermere Crossing
  • Windward Cay
  • Wintermere Harbor
  • Wintermere Pointe
  • Woodbridge on the Green

Horizon West Area Neighborhoods

  • Avalon Cove
  • Cove At Hamlin
  • Enclave at Hamlin
  • Encore at Ovation
  • Hamilton Gardens
  • Hamlin Reserve
  • Hawksmoor
  • Highland Ridge (NEW)
  • Highlands Summerlake
  • Independence
  • Isles Of Lake Hancock
  • Lake Hancock Preserve
  • Lakeshore
  • Lakeside at Hamlin
  • Lakeview Pointe
  • Lakeview Preserve
  • Latham Park
  • Mezzano (NEW)
  • Orchard Hills
  • Orchard Park
  • Osprey Ranch (NEW)
  • Overlook At Hamlin
  • Panther View
  • Ravenna
  • Sanctuary at Hamlin
  • Storey Grove
  • Summerlake
  • Summerlake Groves
  • Waterleigh
  • Watermark
  • Westhaven Ovation (NEW)
  • Wincey Groves
  • Winding Bay

Oakland Area Neighborhoods

  • Deer Island
  • Downtown Oakland
  • Hull Island
  • Johns Cove
  • Johns Landing
  • Longleaf at Oakland
  • Oakland Hills
  • Oakland Park
  • Oakland Trails
  • Trailside Station
  • Tucker Oaks
  • Verde Park

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David Myers - Broker Associate
WinterGardenNeighborhoodRealty.com Team
Ziro Realty, LLC
619 Celebration Ave
Celebration, FL 34747
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