Oakglen Estates Homes for Sale

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Browse Oakglen Estates Homes for Sale in Winter Garden, FL.
Discover community amenities, nearby attractions, schools, and the lifestyle this neighborhood offers.

Oakglen Estates – Winter Garden

Oakglen Estates is a non-gated neighborhood of single-family homes located off East Division Street and East Crest Avenue, just west of North Dillard Street in the northern section of Winter Garden, Florida. Most homes in Oakglen Estates were built between 2005 and 2006 by Adams Homes, offering a blend of contemporary, ranch, and traditional styles in a quiet, residential setting.

Downtown Winter Garden is just minutes away, giving residents easy access to Plant Street dining, shops, and local events. Nearby access to the 429 Expressway makes commuting simple—head south to Walt Disney World and I-4, or north to the Florida Turnpike and Northwest Orlando in Lake County.

Oakglen Estates Neighborhood Amenities

Oakglen Estates has a mandatory HOA that helps maintain the community and includes:

  • • Golf carts allowed

Where Is Oakglen Estates in Winter Garden?

Oakglen Estates is located in the 34787 zip code, within the Northern Original and Downtown Winter Garden area of Winter Garden.

Neighborhood Borders:

  • North: Covington Chase neighborhood

  • South: Courtlea Oaks neighborhood

  • East: West Orange Trail

  • West: Courtlea Park neighborhood

What’s Around & Nearby?

Grocery & Restaurants: West Point Commons

Shopping: Winter Garden Village

Hospital: Orlando Health

Schools: Orange County “Find My School”

Attractions: Walt Disney World & Universal Studios

Outdoor Fun: The West Orange Trail

Local Hangout: Downtown Winter Garden

Closest Beach: Cocoa Beach

Typical Oakglen Estates Home Features

  • Builder: Adams Homes

  • Architectural Styles: Ranch, Contemporary, Traditional

  • Bedrooms: 4

  • Garage: 2-car garages

  • Living Area: Approximately 1,800–2,200 sq. ft.

  • Interior Rooms: Attic, Inside Utility

  • Average Lot Size: Quarter acre

  • Construction Material: Shingle

  • Roof: Shingle

  • Exterior Features: Irrigation system, sprinkler metered; some homes offer trees/woods views.

Thinking about a home in Oakglen Estates?

Call or text the Jared Jones Real Estate Team at 407-706-5000 to learn more today!

Winter Garden Village Area Neighborhoods

Estates Lakeview Preserve

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

Del Webb Oasis (NEW)

Enclave at Hamlin

Encore at Ovation

Hamilton Gardens

Hamlin Reserve

Hawksmoor

Harvest at Ovation

Highland Ridge

Highlands Summerlake

Independence

Isles Of Lake Hancock

Lake Hancock Preserve

Lakeshore

Lakeside at Hamlin

Lakeview Pointe

Lakeview Preserve

Latham Park

Mezzano

Orchard Hills

Orchard Park

Osprey Ranch

Overlook At Hamlin

Panther View

Ravenna

Sanctuary at Hamlin

Storey Grove

Summerlake

Summerlake Groves

Waterleigh

Watermark

Westhaven Ovation

Wincey Groves

Winding Bay

Hamlin Pointe

Hamlin Ridge

Horizon Isle

Lake Star at Ovation

Northlake at Ovation

Parkview at Hamlin

Serenade at Ovation

Silverleaf Oaks

Silverleaf Reserve

Tribute at Ovation

Oakland Area Neighborhoods

Deer Island

Downtown Oakland

Hull Island

Johns Cove

Johns Landing

Lake Apopka Sound (NEW)

Longleaf at Oakland

Oakland Hills

Oakland Park

Oakland Trails

Trailside Station

Tucker Oaks

Verde Park

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