Cypress Point

Cypress Point is a guard-gated luxury estate community in Windermere, FL (ZIP 34786), built out across multiple phases including Phase 2 and Phase 3. The community features custom homes on generous lots with mature landscaping, typically priced from approximately $2M to $4M+. Cypress Point operates with a standard HOA structure — no mandatory private club membership, no invitation-only ownership process — and is within the Windermere school attendance zone. Phased development means architectural styles vary somewhat across the community, but all phases share the same guard-gated entry and HOA framework.

Cypress Point developed in phases over multiple years, with each phase having slightly different architectural guidelines, lot sizes, and build years. Phase 2 and Phase 3 are both established sections of the community with similar guard-gated access and HOA structure, though specific phases may differ in lot orientation, conservation buffers, and community amenities. For buyers comparing Phase 2 vs Phase 3 inventory, the meaningful differences typically come down to lot location and individual home build year rather than community-wide distinctions. We can pull phase-specific comps and sold history on request.

Cypress Point and Cypress Shores are two distinct Windermere communities — easily confused by name but separate by HOA and location. Cypress Point is built out across multiple phases with custom estate homes typically $2M–$4M+. Cypress Shores is a separate guard-gated community with a similar profile but its own HOA. Both share the Windermere school zone and the broader Butler Chain corridor character; buyers shopping the area frequently consider both. The choice usually comes down to specific lot availability, lot size preferences, and individual home design.

HOA fees at Cypress Point are estimated at approximately $300–$550 per month, covering 24/7 staffed gate, common area maintenance, and community landscaping. There is no mandatory private club membership, no golf initiation fee, and no invitation-only ownership requirement. Always verify current HOA fees, any phase-specific assessments, and reserve fund status directly with the homeowners' association before closing.

Cypress Point is within the Windermere school attendance zone, typically serving Windermere Elementary, Bridgewater Middle School, and Windermere High School in Orange County Public Schools. These schools consistently rank among Orange County's top public schools for academic performance and college placement. Always verify specific address assignments with OCPS Find My School before closing, as boundaries can shift between phases.