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Orange County › Winter Park › Osceola Heights
Osceola Heights, Winter Park
Osceola Heights is a neighborhood in east Winter Park, in the 32789 zip code, built mostly in the 1920s. Homes are wood frame and block. Most homes fall between about 1,000 and 3,000 square feet under air, and the median lot is about an eighth of an acre.
Most of Osceola Heights carries no mandatory HOA.
What the homes are
- Built Mostly built in the 1920s, with homes from 1924 to 2026.
- Construction Wood frame and block. Shingle roofs are near universal.
- Style Bungalow, Traditional. Predominantly two story.
- Size Most homes fall between about 1,000 and 3,000 square feet under air.
- Bedrooms Three bedrooms is the most common plan, then four, then two.
- Lot The median lot is about an eighth of an acre.
- HOA Most of the neighborhood carries no mandatory HOA. Confirm on a specific parcel before relying on it.
Where Osceola Heights is
Drive times below are measured on the road network from the center of Osceola Heights, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.
| Driving to | Time | Miles |
|---|---|---|
| Downtown Orlando | 22 min | 7.8 |
| Walt Disney World | 36 min | 27.8 |
| Orlando International Airport | 32 min | 13.7 |
| Universal Orlando | 28 min | 15.9 |
Public schools nearby
- Lakemont Elementary School 2 min, 0.3 mi
- Brookshire Elementary School 6 min, 1.5 mi
- Aloma Elementary 6 min, 2.0 mi
- Winter Park High School 7 min, 2.0 mi
Private schools nearby
- Christian Education at Woodruff Academy 1 min, 0.2 mi
- Chesterton Academy of Orlando 7 min, 2.2 mi
- St. Margaret Mary Catholic School 7 min, 2.1 mi
Parks and recreation
- Marvin Smiley Park 3 min, 0.6 mi
- Phelps Park 2 min, 0.6 mi
- Ward Park Loch Lomond Trail 4 min, 0.9 mi
- Ward Park 4 min, 0.9 mi
Groceries and errands
- Sprouts Farmers Market 3 min, 0.4 mi
- Publix Super Market at Aloma Shopping Center 3 min, 0.7 mi
- Mild Soaps 4 min, 1.3 mi
- The Ancient Olive Gourmet of Winter Park 9 min, 2.1 mi
Nearest is not the same as zoned. The schools above are the closest ones to Osceola Heights 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 Osceola Heights actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 1 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 Osceola Heights
Sale prices ran from $1,035,000 to $1,035,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.
How buyers paid
Cash was 100% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.
Questions about a specific home in Osceola Heights, 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 Osceola Heights in Winter Park, 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.