Bear Gully Pointe
Homes for Sale in Winter Park, FL

Bear Gully Pointe market snapshot (as of September 20, 2026): the median sale price is about $1.01M ($263 per sq ft over the trailing 12 months of closed sales), and a median 78 days on market for closed sales. The trailing-12-month median is down 12% from the prior 12 months, computed from record-level Stellar MLS closed sales (3 closings in the current window).

In ZIP 32792 (Winter Park), 617 homes closed in the last 12 months at a median of $408K ($256/sq ft), down 1.9% year over year, with a median 28 days on market. Right now 49 active and 13 pending listings put supply at about 3.4 months — a balanced market. See the live ZIP 32792 housing market and the Orange County market.

County records show 7 qualified sales in Bear Gully Pointe across 2024–2025 (3 in 2024, 4 in 2025), median $1.15M — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.

Bear Gully Pointe is a community of 60 homes in Winter Park, Seminole County, built between 1972 and 1999 (median 1993.5), with a median living area of about 4,068 square feet. 93% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).

Bear Gully Pointe is a small, established enclave of about 60 larger homes in Winter Park's slice of Seminole County, where the median house is a substantial build from the mid-1990s vintage and price turns almost entirely on updating and layout.

• Eastbrook Elementary · Elementary
• Tuskawilla Middle · Middle
• Lake Howell High · High

Zoned schools reflect the assignments reported on recent Bear Gully Pointe listings and can change; always confirm with Seminole County Public Schools for a specific address.

Buying with schools in mind? We can confirm the exact zoned schools for any Bear Gully Pointe address.

With homes dating from 1972 to 1999 and a median build around 1993, the housing stock here is well past its original systems. Roofs, HVAC, kitchens, and baths are the real variables. The median price tells you the center of gravity — $1,095,000 — but the spread around it is about how much work a house still needs, not about tiers of new construction. Read every listing through that lens and budget for the difference.

A homestead share above 93 percent tells you these are overwhelmingly owner-occupied, long-held homes rather than a churn of rentals or flips. That tends to mean fewer listings and slower turnover, which lines up with a 75-day median on market. Inventory is thin, so timing matters more than in a larger neighborhood — the right house may not appear on your schedule.

In a small, condition-driven market like this, the value is in reading houses accurately — what a given home's age, systems, and square footage actually justify against that $1,095,000 median. With turnover this thin and days on market this long, we help buyers use the slower clock as negotiating room and help sellers price to the current down-trend rather than to last year's hopes.

Listings in this community report association dues of about $167 per month ($2,004 a year) — the median AssociationFee across 57 MLS records, normalised to a monthly figure; most are billed quarterly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-10.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.