Sunset Bay Homes for Sale

About Sunset Bay Neighborhood

Sunset Bay forms a peninsula extending into Lake Down at its southernmost end, accessed via a single entrance off Conroy-Windermere Road. The neighborhood is not gated at the community level — instead, many of the individual estate homes feature their own driveway gates, giving the streetscape a stately, custom-built character rather than the production-home uniformity of newer master-planned developments. A central pond with a fountain, palm trees, and benches anchors the community's interior, while the outer ring of lots wraps around the lakefront.

Of the approximately 35 homes, 24 back directly to Lake Down — a 69% lakefront density that is exceptional even by Butler Chain standards. Homes were built between 1989 and 2005 by various custom luxury builders, producing genuine architectural variety: brick paver driveways, tile roofs, individual gates, and 4-to-6-bedroom floor plans ranging roughly 4,000 to 9,600 square feet. The neighborhood gets its name from the western-facing lake views, which deliver dramatic sunsets across the open water of Lake Down nearly every evening.

Sunset Bay's location is one of the most strategically valuable in Windermere. Across Conroy-Windermere Road to the south sits the main entrance to Isleworth; a few hundred feet east is The Grove at Isleworth shopping center with its Publix, restaurants, and services; and Downtown Windermere is about a mile west via the same road. The combination of Butler Chain frontage, walkable upscale retail, and proximity to Isleworth's gates is essentially impossible to replicate today — Butler Chain lots are nearly never available for new construction.

Sunset Bay Location & Connections

Sunset Bay is located on the eastern side of Windermere in the 34786 ZIP code, with its single entrance on the north side of Conroy-Windermere Road. The peninsula geography means the community is bounded by Lake Down on the north, west, and east of its outer ring, with the neck of the peninsula opening to Conroy-Windermere Road at its southern edge.

The location offers unusually fast access to multiple infrastructure spines: Conroy-Windermere Road runs east to I-4 and Sand Lake Road's Restaurant Row in roughly 10 minutes, while Florida's Turnpike and the 429 Expressway are easily reachable for commutes north toward Apopka or south toward Disney and the attractions corridor.

Sunset Bay Amenities & Lifestyle

Sunset Bay's lifestyle is defined by Butler Chain water access and walkable proximity to one of Windermere's best upscale retail clusters. With most homes backing directly to Lake Down, daily life often includes morning paddleboarding, evening boat rides across the chain to other Butler Chain lakes, and sunset gatherings on lakeside docks. The community itself is intentionally low-amenity — there is no pool, no clubhouse, and no fitness center — because the lake, the docks, and the surrounding Windermere infrastructure provide what residents actually use.

The trade-off most buyers find compelling: in exchange for skipping community amenities they would rarely use, they get a 35-home enclave with custom architecture, decades of mature landscaping, and Butler Chain lakefront density that newer master-planned luxury communities cannot match.

How Sunset Bay Compares

Sunset Bay's value proposition is best understood against two alternatives: newer master-planned luxury communities (Horizon West, parts of Keene's Pointe) and the most prestigious nearby option, Isleworth. Sunset Bay sits in an unusual middle position — Butler Chain frontage like Isleworth's, intimate scale like a custom enclave, but without club membership requirements or new-construction CDD assessments.

Sunset Bay HOA & CDD Information

Sunset Bay operates with a homeowners association that maintains the community's central pond, fountain, common landscaping, and entry signage. Because the community has no pool, clubhouse, or fitness center, HOA assessments are modest relative to amenity-heavy master-planned developments — the trade-off is that residents get a low-fee structure in exchange for self-managing private dock and lakefront upkeep on their own lots.

Sunset Bay does not have a Community Development District (CDD) — see What's a CDD? for context — which is meaningful because most newer luxury communities in the Windermere/Horizon West corridor carry CDD assessments of $2,000–$6,000+ annually layered on top of property taxes.

Frequently Asked Questions