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Orange County › Winter Garden › Pleasant Park
Pleasant Park, Winter Garden
Pleasant Park is a neighborhood in Winter Garden, in the 34787 zip code, built mostly in the 1950s. Homes are block and wood frame, predominantly single story. Most homes fall between about 1,100 and 2,500 square feet under air, and the median lot is roughly a quarter acre.
Most of Pleasant Park carries no mandatory HOA.
What the homes are
- Built Mostly built in the 1950s, with homes from 1928 to 2021.
- Construction Block and wood frame. Shingle roofs are near universal.
- Style Ranch, Craftsman. Predominantly single story.
- Size Most homes fall between about 1,100 and 2,500 square feet under air.
- Bedrooms Three bedrooms is the most common plan, then four, then two.
- Lot The median lot is roughly a quarter acre.
- HOA Most of the neighborhood carries no mandatory HOA. Confirm on a specific parcel before relying on it.
Where Pleasant Park is
Drive times below are measured on the road network from the center of Pleasant Park, 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 | 26 min | 16.4 |
| Walt Disney World | 28 min | 20.5 |
| Orlando International Airport | 31 min | 24.8 |
| Universal Orlando | 25 min | 15.4 |
Public schools nearby
- SLV High School 4 min, 0.9 mi
- Maxey Elementary School 4 min, 1.0 mi
- Dillard Street Elementary School 5 min, 1.4 mi
- Tildenville Elementary School 4 min, 1.3 mi
Private schools nearby
- Foundation Academy, Plant Street Campus 5 min, 1.2 mi
Parks and recreation
- Veterans Memorial Park 2 min, 0.4 mi
- Maple Street Park 3 min, 0.8 mi
- Dr. Bradford Memorial Park 6 min, 1.5 mi
- Butterfly Garden, WO Trail 5 min, 1.5 mi
Groceries and errands
- Key Food Supermarket 3 min, 0.5 mi
- Suns Market 2 min, 0.5 mi
- ALDI 2 min, 0.7 mi
- The Ancient Olive Gourmet of Winter Garden 4 min, 1.0 mi
Nearest is not the same as zoned. The schools above are the closest ones to Pleasant Park 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 Pleasant Park actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 3 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 Pleasant Park
Sale prices ran from $440,000 to $861,360, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.
Homes priced right sold far faster
Median days to go under contract. Shorter is better.
Sellers who priced correctly and held their number went under contract in a median 43 days. Sellers who had to reduce took 155 days and still closed at 96.9% of their already reduced price, after a typical cut of $95,000. Opening high costs time and money, in that order.
Seller concessions
A seller credit covers part of the buyer's closing costs and comes off the seller's proceeds, so the headline sale price overstates what the seller kept. Budget for it if you are selling, and ask for it if you are buying.
How buyers paid
Cash was 67% 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 Pleasant Park, 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 Pleasant Park 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.