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Seminole County › Winter Park › Bear Gully Bay
Bear Gully Bay, Winter Park
Bear Gully Bay is a 1980s neighborhood in Winter Park, in the 32792 zip code. Homes are wood frame and stucco. Most homes fall between about 2,200 and 3,400 square feet under air, the median lot is roughly a third of an acre, and a two car garage is standard.
Homes here carry an HOA, billed annually, typically around $400. Confirm the figure on a specific parcel before relying on it.
What the homes are
- Built Essentially all built in the 1980s.
- Construction Wood frame and stucco. Shingle roofs are near universal.
- Style Traditional, Contemporary. Predominantly two story.
- Size Most homes fall between about 2,200 and 3,400 square feet under air.
- Bedrooms Four bedrooms is the most common plan.
- Garage A two car garage is standard.
- Lot The median lot is roughly a third of an acre.
- HOA Billed annually, typically around $400. Confirm on a specific parcel before relying on it.
Where Bear Gully Bay is
Drive times below are measured on the road network from the center of Bear Gully Bay, 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 | 24 min | 15.0 |
| Orlando International Airport | 27 min | 20.8 |
| Winter Park | 15 min | 5.9 |
| Heathrow and Lake Mary offices | 34 min | 17.6 |
Public schools nearby
- Lake Howell High School 4 min, 1.5 mi
- Eastbrook Elementary School 4 min, 1.5 mi
- Red Bug Elementary School 5 min, 1.8 mi
- Aloma Charter High School 8 min, 3.0 mi
Private schools nearby
- Trinity Preparatory School 6 min, 2.0 mi
- Tuskawilla Montessori Academy 4 min, 1.8 mi
Parks and recreation
- Goldenrod Park 4 min, 1.5 mi
- Red Bug Lake Park 6 min, 2.5 mi
- Sunrise Community Park 8 min, 3.2 mi
- Jamestown Park 11 min, 4.4 mi
Groceries and errands
- Publix Super Market at Shoppes at Aloma Walk 8 min, 2.7 mi
- Fresh Produce, Fruit, Meat & Grocery 6 min, 2.1 mi
- Publix Super Market at Willa Springs Village 6 min, 2.3 mi
- Walmart Deli 5 min, 1.8 mi
Nearest is not the same as zoned. The schools above are the closest ones to Bear Gully Bay 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 Seminole County Public Schools before it matters to a decision.
Places and drive times from Google, checked 18 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.
This page tracks what homes in Bear Gully Bay 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 Bear Gully Bay
Sale prices ran from $625,000 to $625,000, 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 0% 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 Bear Gully Bay, 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 Bear Gully Bay in Winter Park, Seminole County, covering closed sales from 23 September 2025 through 18 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.