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Orange CountyWinter GardenOakglen Estates

Oakglen Estates, Winter Garden

Oakglen Estates is a 2000s neighborhood in northeast Winter Garden, in the 34787 zip code. Homes are block and stucco, predominantly single story. Most homes fall between about 1,900 and 3,000 square feet under air, the median lot is roughly a quarter acre, and a two car garage is standard.

Homes here carry an HOA, billed annually, typically around $369. Confirm the figure on a specific parcel before relying on it.

What the homes are

  • Built Essentially all built in the 2000s.
  • Construction Block and stucco. Shingle roofs are near universal.
  • Style Contemporary, Ranch. Predominantly single story.
  • Size Most homes fall between about 1,900 and 3,000 square feet under air.
  • Bedrooms Four bedrooms is the most common plan, then three.
  • Garage A two car garage is standard.
  • Lot The median lot is roughly a quarter acre.
  • HOA Billed annually, typically around $369. Confirm on a specific parcel before relying on it.

Where Oakglen Estates is

Oakglen Estates, centered at 28.574463, -81.577303. Drag to explore.
Street level, inside the neighborhood. Drag to look around.

Drive times below are measured on the road network from the center of Oakglen Estates, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.

Driving toTimeMiles
Downtown Orlando24 min16.9
Walt Disney World28 min23.9
Orlando International Airport29 min25.3
Universal Orlando23 min15.8

Public schools nearby

  • Dillard Street Elementary School 3 min, 0.8 mi
  • St Lillie V High School 4 min, 1.0 mi
  • SLV High School 5 min, 1.3 mi
  • Maxey Elementary School 5 min, 1.8 mi

Private schools nearby

  • Foundation Academy, Plant Street Campus 4 min, 1.1 mi

Parks and recreation

  • Newton Park 3 min, 0.8 mi
  • Dr. Bradford Memorial Park 4 min, 0.9 mi
  • The Chapin Station Ravine Park 4 min, 1.2 mi
  • Maple Street Park 5 min, 1.4 mi

Groceries and errands

  • A&E Grocery Store 3 min, 1.2 mi
  • D J Discount Market 5 min, 1.1 mi
  • Tn Food & Grocery 5 min, 1.1 mi
  • Tea Bar 4 min, 1.2 mi

Nearest is not the same as zoned. The schools above are the closest ones to Oakglen Estates by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Orange County Public Schools before it matters to a decision.

Places and drive times from Google, checked 20 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.

This page tracks what homes in Oakglen Estates actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 0 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated September 2026.

Read this one loosely. Fewer than eight homes closed here in the last year, so every median on this page rests on a small sample and can swing on a single sale.

What homes sold for in Oakglen Estates

n/aMedian sale price
n/aMedian per square foot
n/aMedian days to contract
0Homes sold in 12 months

Questions about a specific home in Oakglen Estates, or want to know what yours would sell for?
Call or text Brenden Rendo at 407-616-9019 or send a message.

About this data. Source is the Stellar MLS feed for Oakglen Estates in Winter Garden, Orange County, covering closed sales from 25 September 2025 through 20 September 2026, refreshed monthly and current as of September 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. Data believed accurate but not guaranteed; listings and closings change daily.