A Different Kind of Family Purchase

Why Some Families Approach It This Way

The reasons families consider multigenerational purchases vary. Some families want a fixed gathering point that brings everyone together more often. Some are responding to the increased flexibility of remote work. Some are planning for long-term succession and want to involve the next generation early. Each family's reason is its own.

What these purchases have in common is that they involve more than one household making the decision together — and that requires a different kind of planning than a single-buyer purchase.

Property Types That Support Multigenerational Living

Different property configurations on Maui support different living arrangements. Some examples:

Lockoff configurations. Some Maui condominium units — including certain floor plans at Wailea Ekahi, Maui Banyan in Kīhei, and Grand Champions — have a lockoff: a portion of the unit that can be closed off with its own entrance. There is still only one kitchen in the unit, but the lockoff side can function as an attached guest suite for extended family visits. Lockoff units are also popular among short-term rental buyers for the flexibility to rent the portions separately or not — having that option improves the value. It is important to be informed and to verify rentability, zoning, and HOA rules for any specific unit before purchase.

Adjacent or stacked unit purchasing. In condominium communities such as Hoʻolei at Grand Wailea, Wailea Beach Villas, Wailea Elua, Wailea Ekahi, and Polo Beach Club, some families purchase two separate units near each other — sometimes side by side, sometimes one above the other. Each household holds its own title and has its own entry. The proximity is the appeal. Hoʻolei at Grand Wailea is arranged as six units per building with main entrances and garage entrances into each unit.

Estate properties with detached structures. Some larger residential lots in Wailea and Mākena support detached guest cottages, ʻohana units, or pool houses under existing zoning. Zoning rules vary by parcel and current Maui County zoning regulations should always be verified for any specific property before purchase.

Branded residences with on-site services. The Andaz Maui Residences in Wailea are an example of branded residences offering fee-simple villa ownership with hotel services available on the property. For families who want to gather without managing day-to-day property logistics, this kind of arrangement removes some friction.

Ownership Structures Are an Estate Planning Decision

Multigenerational purchases rarely involve a simple two-name deed. The structures vary depending on the family's circumstances and goals. Examples include LLCs owned by a family trust, tenants in common with documented use rights, and qualified personal residence trusts. Each structure carries tax, succession, and gifting implications.

These decisions are estate planning decisions first and real estate decisions second. They should be worked out with a Hawaii-licensed estate attorney and a qualified CPA before an offer is written. The structure shapes which property is appropriate, not the other way around.

The Travel-Time Consideration

Maui is roughly five hours from Los Angeles, five and a half from San Francisco, six from Seattle, and approximately ten hours from New York. For a family with members in different cities, the flight time often encourages longer visits — a week or more rather than a weekend. Some families find that this naturally supports the kind of together-time a shared family property is meant to provide.

Jolanta's Feedback

Families who plan well tend to start with a conversation about how they want to use the property over the next many years — and then look at inventory. The families who find it harder are the ones who start with a property they have fallen in love with and try to make the family plan fit it. The order of operations matters. Estate planning first, property second.