Hawaii vacation homes for sale with Caretaker’s cottages

Many buyers come from outside of the state to buy vacation homes here in Hawaii. And who wouldn't want a vacation here with our beautiful weather and beaches? It's no wonder that we attract thousands of people every year to buy vacation homes. With the purchase of a vacation home, a big concern is that many buyers have is “Who will take care of my property when I'm not here?”. There are people and companies that help take care of your property. For example, Hawaii House takes care of some clients’ properties: making needed repairs and preparing them for when the owners come into town. It’s always good to keep the property in tip-top shape and not let any maintenance get deferred.

Caretakers to help maintain your Hawaii Vacation Home

However, some people may choose to actually have an on-site caretaker. This can actually be very nice having someone live on the property day in and day out. Being able to notice some extra care items like if the swimming pool needs attention or if it is time to paint the exterior. These are all added things that someone living on the property every day can address very easily. The addition of possibly a reduced rent in exchange for this care can create a nice symbiotic relationship between property owner and caretaker.

A good caretaker can keep the property in pristine condition and thus relieve the owner of the stress and constant work on day to day upkeep of a house. This is why it's nice to consider homes that already have a caretaker apartment or cottage so that the seamless transition can occur from purchasing a property to immediately being able to put a caretaker in place to manage the property. The truth this is that there are quite a few very reliable people that would love to have this arrangement to take care of and watch over a property on behalf of the owner. Let's look at a few properties that have caretaker quarters already in place in areas of the island when people are looking for a vacation home:

Three Oahu Hawaii vacation homes for sale with Caretaker's quarters.

4026 black point Road Honolulu - Vacation home

4026 Black Point Road in Diamond Head

1. 4026 Black point Road Diamond Head is in a gated section Black Point between Diamond head and Kahala. The homes here are tightly compacted and have a loose association to pay for the entry gate and the limited amount of common areas that exist in this little neighborhood. This home has a total of 5 bedrooms and 4 bathrooms with just under 4000 ft.² living area inside. The land area is 12,214 ft.² and the list price is $2,888,000. The main level of the home has 3 bedrooms and 2 baths and a large deck with ocean views. There is putting green and a small basketball sports court which could allow room enough for a future swimming pool. Downstairs, with a separate entrance, is a 1 bedroom, 1 bath caretaker apartment. An ideal situation to take care of this property. The home does come with photovoltaic on the roof to reduce electricity. It’s a beautiful home. If you're buying this as a vacation home, you have the added secure feeling of not only being in a gated community but also being able to have a caretaker who watches over the property. View all Black Point homes here. 




2. 334 Lala Place in Lanikai.

334 Lala Place Lanikai home

334 Lala Place Lanikai

This 4 bedroom, 4 bath Lanikai beach home has 3000 ft.² interior and just under 13,000 ft.² square feet of land. The asking price is $2,695,000. This home is on the hillside part of Lanikai. Homes on the hillside of Lanikai tend to have beautiful views of the ocean and the Mokulua islands. This is perhaps one of the most photographed beaches on the island. This is such a popular neighborhood, located in the Kailua district of Oahu,  for people that vacation as well as local residents. Lanikai beach has truly been popular for many, many years. This home’s casual elegance really makes it ideal for a beach house and is perfect for entertaining. Because of its location, it's in a very quiet section of Lanikai too. The open floor plan expands out to a very large lanai and there is a separate bedroom and bathroom which is perfect for a caretaker. View all Lanikai homes here 






3. 61-785 Papailoa Road in Kawailoa in Haleiwa.

61785 Papailoa Road Haleiwa, North Shore

61785 Papailoa Road Haleiwa, North Shore

This North Shore home is actually much more of an estate. This half acre parcel close to Haleiwa town on the North Shore of Oahu has a total of 7 bedrooms and 7 1/2 bathrooms. The living area is 7680 ft.² and the lanai area is an additional 3420 ft.². Built in 2001, this is a gorgeous estate listed for $9,975,000. Because of its positioning, the home has panoramic views not only the ocean and the beaches surrounding but also back towards the mountains. This is truly a wonderful place to gather. The main residence has a grand living room, a gourmet kitchen, a spacious dining room and surround sound theater. There's over 100 linear feet of direct beach frontage which is such a large amount. A caretaker's cottage sits above the garage. This is like your own mini resort with lush tropical plantings, open-space and long sandy beach for a nice long walk. The caretaker's cottage is perhaps the most key element. Having someone onsite year-round at a property like this can make all the difference to manage the landscaping and the house. The caretaker can give any absentee owner peace of mind that their properties being maintained properly. View all North Shore real estate here. 




I have many clients who are foreign buyers of Hawaii real estate from places like Hong Kong, Australia, New Zealand, Korea, Canada and Europe. They always want to know that your property is being maintained. Having a caretaker is one of the easiest ways to do it. Picking a property that already has space for caretaker can be key. If you're looking for a Hawaii vacation home or an investment property or your forever home, please don't hesitate to call me. I am more than happy to help you find your piece of paradise.

Give me a call at 808-394-9779   or click here to email me

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