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Orange County › Winter Garden › Deer Island
Deer Island, Winter Garden
Deer Island is a neighborhood in west Winter Garden, in the 34787 zip code, built most often in the 1990s. Homes are block and stucco. Most homes fall between about 2,800 and 6,500 square feet under air, and the median lot is about an acre.
Homes here carry an HOA, billed semi-annually, typically around $705. Confirm the figure on a specific parcel before relying on it.
What the homes are
- Built Most often built in the 1990s (35% of homes), with homes from 1937 to 2023.
- Construction Block and stucco. Shingle roofs on 75% of homes.
- Style Contemporary, Traditional, Mediterranean. Predominantly two story.
- Size Most homes fall between about 2,800 and 6,500 square feet under air.
- Bedrooms Four bedrooms is the most common plan, then five, then three.
- Lot The median lot is about an acre.
- HOA Billed semi-annually, typically around $705. Confirm on a specific parcel before relying on it.
Where Deer Island is
Drive times below are measured on the road network from the center of Deer Island, 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 | 25 min | 19.6 |
| Walt Disney World | 30 min | 26.6 |
| Orlando International Airport | 30 min | 28.0 |
| Universal Orlando | 25 min | 18.6 |
Public schools nearby
- Oakland Avenue Charter School 8 min, 3.0 mi
- Whispering Oak Elementary School 15 min, 7.2 mi
- Tildenville Elementary School 10 min, 4.1 mi
- SunRidge Elementary School 12 min, 5.1 mi
Private schools nearby
- Family Christian School, Oakland 6 min, 2.1 mi
Parks and recreation
- Oakland Nature Preserve 7 min, 2.3 mi
- Pollard Park 6 min, 2.3 mi
- Healthy West Orange Boardwalk at Oakland Nature Preserve 8 min, 2.5 mi
- Speer Park 8 min, 2.9 mi
Groceries and errands
- Publix Super Market at Stoneybrook West Village 14 min, 6.6 mi
- Publix Super Market at East Towne Center 7 min, 2.8 mi
- A&E Grocery Store 10 min, 4.4 mi
- Armazém X Clermont 7 min, 3.1 mi
Nearest is not the same as zoned. The schools above are the closest ones to Deer Island 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 Deer Island actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 4 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 November 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 Deer Island
Sale prices ran from $975,000 to $2,775,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.
By size
| Home size | Sales | Median price | Median $/sq ft | Median days |
|---|---|---|---|---|
| 3,000 sq ft and up | 4 | $1,434,984 | $443 | 108 days |
A price per foot taken from the whole neighborhood should never be applied straight to one house.
Price cuts and time to contract
Median days to go under contract. Shorter is better.
Sellers who held their number went under contract in a median 16 days. Sellers who had to reduce took 192 days and still closed at 95.5% of their already reduced price, after a typical cut of $125,000.
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 25% 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 Deer Island, 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 Deer Island in Winter Garden, Orange County, covering closed sales from 7 November 2025 through 2 November 2026, refreshed monthly and current as of November 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.