4 Tips for Buying a Second Home in Kihei

4 Tips for Buying a Second Home in Kihei

  • Chelsea Dimin
  • 07/6/23

Six miles of pristine, white sand beaches adorn the southwest Maui city of Kihei. All of the best of Hawaii is available right here, from snorkeling to surfing, whale watching to lush flora and sunshine-filled days. Does this sound like your kind of paradise? Chelsea Dimin, local real estate agent and Kihei luxury home expert, couldn’t agree more. If you’re looking to buy a second home in Kihei, making a few good choices can help you find the perfect one.

Choose the right Kihei luxury home

Begin your search for the perfect Kihei house for sale right in your own living room. And no, I’m not talking about an online search. That will come. Start with your family, your lifestyle, and your needs. Evaluate the life you’re living, and the one you’d like to have, by reflecting on these questions:

  • How much time does your family spend on vacation, and what sort of vacationers are you? Do you get away to relax and take it easy, or do you prefer action-packed days with new adventures?

  • How would you use a second home? Do you anticipate keeping the circle small — just family and friends — or are you seeking to generate some rental income when you are not there?

  • How much time do you realistically expect to spend in your Kihei luxury home? If you haven’t had a vacation in three years, you may not utilize your property well. However, if you are a regular vacationer and love the idea of a “home away from home” in a tropical paradise, a Kihei house for sale may be just what you are looking for.

  • Might imminent changes in your family, such as the arrival of a new grandchild or an elderly parent moving into your household, affect your ability to enjoy your second home?

  • What features matter most to you in a vacation home?
Use these reflective questions to engage in a brainstorming conversation with your family and begin to put together a list of needs and wants. This list can guide your search, narrow your options, and help your realtor understand how to best serve you as she helps you locate and acquire your perfect second home.

Choose the right realtor

Selecting the right realtor opens doors to access the best properties. She is your insider ally who knows the nuances of the local market, up-and-coming developments and opportunities, and all of the legal aspects of the transaction. She will work tirelessly as your representative to make sure that your interests are protected and your real estate goals are met.

How do you choose the right realtor? Look for these traits:

  • Local experience and expertise - A realtor who lives, works, and plays in Kihei will know the community and its resources, providing first-hand knowledge of the best areas, local amenities and services.

  • Proactive vs. reactive approach - Choose a realtor who will go to work for you, reaching out to you with properties, updates, seeking solutions to problems and soliciting information about properties before you have to ask.

  • Outstanding listening skills - As your representative, the agent must take the time to learn your needs and your desires and be willing to work within the parameters of them.

  • Negotiation skills - When it comes to making an offer, determining the terms of sale, your agent has to know how to get you the best possible deal for that Kihei luxury home. She must work with skill, confidence, and resolve to represent your interests.

  • Proven track record - Great realtors develop long-term relationships with their clients and often have repeat customers. Inquire about her performance data and speak with former clients.
Realtor Chelsea Dimin brings each of these traits to her business and strives to exceed expectations in every transaction.

Choose the right time

Even when you are ready to make that second home purchase, evaluating what is happening in the economy and local housing market are important components of your research, and insights your realtor is trained to provide. According to the University of Hawaii’s Economic Research Organization, this is a good time to purchase real estate in Hawaii. Tourism increased 14% between March 2022 and 2023, indicating the industry is almost fully recovered from the COVID-19 pandemic. Hotel room rates have significantly increased over the last few years, so visitors are looking for different lodging opportunities. If you are considering using your Kihei luxury home as a vacation rental, this could prove very lucrative.

There’s more good news for the economy as a whole. Inflation, which peaked at 9% in the summer of 2022, has now receded to 5% and this descent toward a healthy 2% continues. Analysts are now optimistically watching the Fed to see if interest rates for home loans will now decline. The purpose in all of the rate hikes over the last year has been served. They were meant to curb inflation, and now that this is being achieved, lowering rates should follow. This is great news for any homebuyer who will have a mortgage.

Choose the right location

Would you prefer a single-family residence for your second home, or would you prefer a condo? There are unique features to consider with both which may enhance the quality of your vacation.

Single-family Kihei luxury homes typically offer privacy and beautiful vistas in the most desirable locations. They are out of the hustle-and-bustle of the community and provide a true sanctuary. Alternatively, condos offer convenient amenities, such as grilling areas, shared greenspace, and swimming pools without requiring maintenance work from you. The only upkeep that concerns the condo owner is their own personal unit. Everything else is covered by fees.

What will you choose?

An incredible vacation residence in Kihei is awaiting you. Are you ready to find it? Your local Kihei agent, Chelsea Dimin is at your service to guide you through choosing the right home, the right location, and the right time to buy. Give her a call today.
*Header photo courtesy of Chelsea Dimin

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, NYmag.com, 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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