Windsor Island vs Windsor Cay

Windsor Island sits around Sand Mine Road, with its association address on Aloha Boulevard in Davenport. Windsor Cay centers on Windsor Cay Boulevard, with a Clermont address in Lake County's Four Corners area. Both serve the Orlando-area market, but neither is within Orlando city limits. During viewings, compare routes from each actual home to the same destinations that matter to you, whether a particular Disney park, your workplace or places you expect to visit regularly. Test those journeys at relevant times rather than choosing a community on a broad claim of better Disney access.

Compare ownership charges for the specific homes on your shortlist, not just the community names. Association charges and their inclusions are one part of the picture; community development district assessments are another. Windsor Island is associated with Sandmine Road CDD, while Windsor Cay has Windsor Cay CDD. Request current association information and review parcel-specific district records so you understand what applies to each property. Ask which services are covered and which require separate payment. Cabana use, for example, is separately chargeable at both communities. A clubhouse and pool on the amenity list do not mean every related service is included in your regular charges.

Both communities are described as short-term-rental resorts, so second-home enjoyment and potential rental use belong in the comparison. That designation does not replace a review of the rules attached to the property you want to buy. Read the current declarations, amendments and property-specific requirements with your intended use in mind. If you hope to live there permanently, confirm that use explicitly. For a second home, check owner-stay provisions, occupancy limits and letting requirements before planning your calendar. We recommend resolving these questions early, so you compare homes that fit your plans rather than relying on the resort label alone.