Is Buying a Second Home in Wailea Right for You?

Is Buying a Second Home in Wailea Right for You?

  • Chelsea Dimin
  • 05/5/23

Buyers seeking a second home aren't alone; their desire for another property is shared by millions of people around the U.S. These primarily exist in Florida, California, New York, Texas, Michigan, and Hawaii.

Before searching for homes for sale in Wailea, buyers should be aware of the long-term responsibilities that come with owning two homes to decide if now is the right time to invest.

Twice the financial burden

Buyers can expect to deal with repairs as well as everyday expenses twice as often when buying a second home. Although it sounds like common sense, many buyers don't financially account for just how much money it costs to own two homes.

For example, if you have a sewer pipe problem in your main residence and then, a short time later, your HVAC system needs repair in your second home, you’ll have two substantial back-to-back bills.

In addition to the unforeseen issues that may occur, there are double the regular expenses associated with owning a second home. Such costs include HOA fees, rental management fees, utilities, property taxes, mortgage payments, and even travel costs when visiting your second home.

When it comes to buying a home, constructing an accurate budget is paramount. Be sure to include additional costs like flood insurance and possible appliance replacements. Unforeseen or long-term costs can add up if not originally accounted for.

As you contemplate living in Wailea, keeping your long-term objectives in mind is crucial. Consider if this purchase will still allow you to save for retirement and how much debt you currently have. Moreover, ask yourself whether the proposed house will cut into an emergency fund and if your current home is paid off. The more of these elements that are taken care of before acquiring a second property, the better equipped you will be to make a purchase.

How to finance a second home

If buyers already have a mortgage and have now set their sights on a second home, they should know that banks will assess their eligibility for the loan. This includes reviewing not only both credit reports but also income levels, job history, possessions, and liabilities. When it comes to financing a second home, buyers should feel confident in the financial picture they're painting.

Applying for a loan to finance your second home is not as intimidating as many people think, and it's pretty similar to applying for a primary mortgage. Consider your financing options, including securing a second home mortgage, taking out an equity loan or line of credit from your current residence, or refinancing with cash-out from existing mortgages.

Utilizing a home equity line of credit (HELOC) or other low-interest products to consolidate your high-interest credit card debt can make it easier for lenders to have confidence in buyers. Additionally, if possible and feasible, waiting until most of the first home has been paid off or until all extra debt has been settled could help strengthen a financial situation.

Making the trip

If buyers are contemplating the idea of living in Wailea seasonally, they should think it through carefully. The saying “too much of a good thing can be bad” is applicable to holiday homes. After 10 summers spent under the sun in one location, allure may quickly fade and give way to frustration (and expenses) linked with maintenance or extensive travel time, and leave you wondering if this was what you wanted on a long-term basis.

Purchasing a second home shouldn't compromise travel to other places. If one enjoys being in the same destination annually, then it may be wise to invest in a property there. However, if a buyer's long-term plan includes exploring different parts of the world every year, keeping up with expenses for two homes could become difficult. Consider both options when making this important decision.

Renting as supplemental income

If buyers are searching for supplemental income when looking for homes for sale in Wailea, leasing is the way to go. However, before doing so, it's essential that buyers check if any neighborhood bylaws and Homeowners Association (HOA) rules permit renters or Airbnb-like rentals.

When budgeting for a second home, homeowners should also account for the costs of cleaning services, upkeep, home management, and insurance. However, covering these costs (including the mortgage) could mean the homeowner must sacrifice their desired time in the residence due to renting it out. Additionally, the highest demand from renters will be during peak season, which is probably when a buyer most wants to enjoy their second home. For the reasons listed above, it is crucial the buyer considers long-term goals and works with a trusted realtor or financial advisor to determine if renting the home out is right for them.

Reasons to consider buying a second home

Investing in a second home is a great way for buyers to open themselves up to new income possibilities. Now, more than ever before, with platforms like Airbnb and VRBO, owning a second property can be utilized as an avenue for extra passive income. If buyers are savvy enough when choosing a second home, such as one in Wailea, a second home could be a lucrative asset.

Investing in a second home can be an excellent way to branch out beyond stocks, bonds, and a 401(k). Second-home buyers stand to benefit from real estate appreciation over time while also having something valuable to leave to any children.

Not only can a second home be financially beneficial, but it also allows you and your family to have quality time together in one special place.

Become a second home owner

No one can decide if buying a second home is the right choice for a prospective buyer except for the buyers themselves, with the help of a good financial planner. As laid out in this article, there are a lot of pros and cons to owning a second home. If you're ready to start looking for homes for sale in Wailea, contact realtor Chelsea Dimin today to learn more.

Chelsea Dimin

Chelsea Dimin

Realtor® Broker

About The Author

Chelsea Dimin stands at the pinnacle of Maui's luxury real estate, consistently ranking among the top 1% of agents in sales volume. Chelsea specializes in oceanfront property and vacation homes and has over 17 years of expertise in real estate, business development, and advertising sales.

Originally from Milwaukee, Wisconsin, Chelsea holds degrees in Journalism and Spanish from the University of Wisconsin Madison. Her career journey led her to Los Angeles in 2006, honing negotiation skills representing top brands in digital media and advertising sales. In 2010, she joined New York Magazine's digital publication,, as the West Coast Advertising Sales Account Executive. In 2014, Chelsea embraced Maui's allure, obtaining her real estate license and collaborating with a local developer. As a Realtor Salesperson, she played a key role in transforming vacation rental estates into profitable ventures, attracting a global clientele.

Acquiring her Broker license in 2017, Chelsea made history in January 2023, becoming the first female Realtor to list and sell a $32 million dollar home in Makena, as reported by the Wall Street Journal. Today, Chelsea guides buyers in realizing their Maui dream homes. Known for tenacity and creativity, she forges connections, assesses needs, and delivers strategic results. Chelsea's signature is creating opportunities, leveraging a global network for off-market deals and win-win negotiations.

Clients appreciate Chelsea's commitment to staying informed, providing updates on values, market trends, and recommendations. Beyond real estate, Chelsea enjoys an active lifestyle, engaging in surfing, yoga, barre classes, mountain biking, beach runs, jungle hikes, and waterfall adventures with her husband Tim and beloved pitbull, Lulu.

“My mission is to exceed your expectations so that you never hesitate to refer your friends, family or coworkers to me in the future.”

Work With Chelsea

Are you interested in buying or selling a home on Maui? Contact me to tap into my local knowledge and global connections. My mission is to exceed your expectations so that you never hesitate to refer your friends, family or coworkers to me in the future.

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