Bay Isle
Homes for Sale in Winter Garden, FL

Bay Isle sits in Winter Garden as a gated, deed-restricted community of larger-format homes from the early-to-mid 2000s, with association-owned recreation and reclaimed-water irrigation built into the HOA structure.

Stellar MLS sales records identify 52 homes in Bay Isle that have changed hands since 2004, built between 2002 and 2006 (median 2004), with a median living area of about 3,485 sq ft and a typical 4-bedroom, 3.5-bath layout; 100% 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.

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

In ZIP 34787, 957 homes are on the market and 30% are under contract — a steady corner of Winter Garden.

Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).

In ZIP 34787 (WINTER GARDEN), 2,162 homes closed in the last 12 months at a median of $595K ($251/sq ft), down 0.6% year over year, with a median 36 days on market. Right now 357 active and 169 pending listings put supply at about 3.8 months - a balanced market. See the live ZIP 34787 housing market and the Orange County market.

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

• SunRidge Elementary · Elementary
• SunRidge Middle · Middle
• West Orange High · High

Zoned schools reflect the assignments reported on recent Bay Isle listings and can change; always confirm with Orange County Public Schools for a specific address.

Buying with schools in mind? We can confirm the exact zoned schools for any Bay Isle address.

At 90 homes total, Bay Isle is not a high-volume community, and the current single active listing reflects that. The homes themselves cluster around a 2004 median build year, and the 3,371-square-foot median living area signals this was platted for larger, move-up-style floor plans rather than starter product. That size profile, combined with the narrow four-year build window, means homes here tend to share similar bones - buyers are usually comparing layout and condition rather than era.

The homestead share of 74.4% is a useful market signal: a large majority of owners have filed for homestead exemption, which typically points to longer hold periods rather than frequent investor turnover. Paired with deed restrictions and a gated structure - the listings reference both guarded and non-guarded gated access, so this should be confirmed at the HOA level - Bay Isle reads as a community built for stability rather than rapid resale.

A community with one active listing and infrequent closings rewards an agent who tracks it closely rather than one relying on general area data. We watch Bay Isle's actual closing activity and homestead patterns to help sellers price against real, current comparables and help buyers move quickly when the rare listing appears.

Listings in this community report association dues of about $150 per month ($1,800 a year) - the median AssociationFee across 12 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, 2026-09.

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