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Orange County › Winter Park › Hills
Hills, Winter Park
Hills is a 1960s neighborhood in north Winter Park, in the 32789 zip code. Homes are block and brick, predominantly single story. Most homes fall between about 2,000 and 2,800 square feet under air, the median lot is roughly a quarter acre, and a two car garage is standard.
Hills has an optional homeowners association rather than a mandatory one, so there is no deed restricted membership to inherit. Dues run about $50 annually for those who join. Confirm the position on a specific parcel before relying on it.
What the homes are
- Built Essentially all built in the 1960s.
- Construction Block and brick. Shingle roofs are near universal.
- Style Traditional, Ranch. Predominantly single story.
- Size Most homes fall between about 2,000 and 2,800 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 Optional rather than mandatory, so there is no deed restricted membership. Dues run about $50 annually for those who join. Confirm on a specific parcel before relying on it.
Where Hills is
Drive times below are measured on the road network from the center of Hills, 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 | 23 min | 12.2 |
| Walt Disney World | 37 min | 31.4 |
| Orlando International Airport | 31 min | 24.1 |
| Universal Orlando | 30 min | 19.4 |
Public schools nearby
- Dommerich Elementary School 6 min, 1.9 mi
- Lakemont Elementary School 6 min, 1.8 mi
- English Estates Elementary School 8 min, 2.9 mi
- Aloma Charter High School 7 min, 2.7 mi
Private schools nearby
- Lake Forrest Preparatory School 6 min, 1.9 mi
- Christian Education at Woodruff Academy 6 min, 1.9 mi
- Chesterton Academy of Orlando 5 min, 2.1 mi
Parks and recreation
- Howell Branch Preserve 2 min, 0.6 mi
- Branch Tree Park 3 min, 1.0 mi
- John Langdon Park 3 min, 0.9 mi
- Lake Knowles Park 5 min, 1.4 mi
Groceries and errands
- DG Market 2 min, 0.6 mi
- Publix Super Market at Casselberry Commons 3 min, 1.0 mi
- SuperFresh Market 5 min, 1.2 mi
- In-N-Out Market 6 min, 1.6 mi
Nearest is not the same as zoned. The schools above are the closest ones to Hills 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 Hills actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 2 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 Hills
Sale prices ran from $750,000 to $1,027,000, 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 76 days. Sellers who had to reduce took 44 days and still closed at 91.6% of their already reduced price, after a typical cut of $70,000. 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 50% 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 Hills, 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 Hills 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.