Bear Gully Bay
Homes for Sale in Winter Park, FL

A small, water-oriented enclave inside Winter Park but sitting in Seminole County — close-in location with a quieter, low-turnover feel. Expect to evaluate homes one at a time rather than by a running market rhythm.

Stellar MLS sales records identify 12 homes in Bear Gully Bay that have changed hands since 2005, built between 1986 and 1989 (median 1988), with a median living area of about 2,561 sq ft and a typical 4-bedroom, 2.5-bath layout; 92% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.

Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.

Bear Gully Bay is too small for its own price trend, so here is the market around it.

In ZIP 32792, 137 homes are on the market and 21% are under contract — a steady corner of Winter Park.

Across Seminole County, 1,646 homes are active and 585 pending (26% under contract).

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.

ZIP and county figures describe the wider market, not Bear Gully Bay specifically. Momentum Research analysis of MLS records.

The defining feature of Bear Gully Bay is scarcity of transactions. With a limited closings window in a compact area, there isn't a deep well of recent sales to triangulate value. That means condition-driven pricing: an updated home and a dated one can sit far apart, and the spread between them tells you more than any single headline figure.

Location does real work here. You get a Winter Park address with Seminole County positioning — a combination that appeals to buyers who want proximity without the density of the core. The trade-off is that with few homes changing hands, opportunities are episodic. You buy when something surfaces that fits, not when the calendar says so.

In a low-volume enclave, the value is in judgment, not in a spreadsheet of comps. We underwrite each property against its condition, lot, and position rather than a neighborhood average that doesn't really exist yet — and we'll tell you plainly when a listing is priced on optimism rather than evidence.

Listings in this community report association dues of about $38 per month ($456 a year) — the median AssociationFee across 13 MLS records, normalised to a monthly figure; most are billed annually. 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, 2026-09.

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