7 Things to Look For When Buying a Vacation Home in Wailea

7 Things to Look For When Buying a Vacation Home in Wailea

  • Chelsea Dimin
  • 10/24/23

Wailea is a peaceful community on the southern coast of Maui. Spanning approximately 1,500 acres, the oceanside paradise is known for its stunning gated communities and breathtaking sunsets. Wailea real estate puts residents within walking distance of the water, making it an ideal destination for those hoping to invest in a vacation property. 

With a little bit of everything, Wailea is quickly becoming one of the more popular local spots to call home. If you’ve been wondering whether a Hawaiian vacation home is right for you, make sure you keep these seven things in mind while you make your decision.

1. Hire a local Realtor

As you browse Wailea homes and condos for sale, don’t forget to partner with an experienced real estate agent with local knowledge. Unless you already live here, navigating a home purchase from afar can be tricky. A local Realtor can work on your behalf to scout top properties and provide you with detailed information such as various HOA fees, vacation rental income history, average daily rates for specific complexes, and common floor plans in specific subdivisions.

Although the Wailea market is competitive and inventory is low, resales are consistent giving buyers options to choose from at any given time. The right real estate broker can help you set your budget, find a local lender, explore properties virtually, and ultimately secure your dream vacation home or condo, all from the comfort of your existing home office.

2. The right location

When you look for a Wailea vacation home, you want to make sure you’re set on the location. It’s a good idea to visit Wailea before investing so you can be sure it’s the right place for you. One of the biggest draws to the area is the fact that, though it’s small, there’s still a variety of activities to do. The sand and surf are only the beginning. The Wailea Golf Course is right at the heart of town, or there’s the Wailea Tennis Club and the Wailea Blue Course to the south. The Shops of Wailea, art galleries, parks, restaurants, and the Wailea Beach walking path, are just the tip of the iceberg when it comes to enjoying your vacation home in Wailea.

3. Your preferred home style

Wailea homes for sale come in a variety of styles, and interested buyers will want to make sure they know which one suits them best. Split-level homes are a popular choice that offers residents multiple floors and lovely views in neighborhoods such as Wailea Pualani and Wailea Kai. Single story, open floor plans and homes with swimming pools are popular in Wailea Highlands and the newest subdivision Wailea Golf Estates II.

4. Top interior amenities

Are you hoping for the latest in appliances and automated home technology? Do you want updated fixtures in the kitchen and bathroom? Besides the smaller details, think through how many bedrooms and bathrooms you’d prefer and the type of layout that appeals to you most. Buyers in Hawaii tend to place value on high ceilings, ocean views, and privacy. Work with your real estate broker to determine your top list of amenities before you start your search. Rely on them to connect you with reliable local vendors such home audio/visual installers, pool and spa maintenance companies, landscape designers, and local solar and roofing companies.

5. Functionality

Whenever you search for a vacation home, you’ll want to think about its functionality. How often and for how long will you use it? What do you hope to do there? If you imagine yourself spending most of your time relaxing on your lanai, you may want to look for a home with higher square footage and private outdoor space. If you plan on spending most of your time away from the property to take in all the best of the local scenery, size may not be as big of a factor as location is. Always keep in mind, too, that your priorities and interests may shift once you actually start spending time in your new home.

6. Low upkeep costs

Another important consideration to make before buying a vacation home is the cost of upkeep, especially if your primary residence is on the mainland. How will you manage repairs or renovations on your new property? Are you willing to take on additional costs year-to-year? Thinking through these financial pieces in advance can help you feel more confident about your investment when buying. Work with a knowledgeable real estate broker who can recommend trusted property managers, and quality local vendors to help service your property.

7. Local regulations

Finally, it’s important to keep local regulations in mind, particularly if you plan on using your vacation home as a short-term rental property when you’re not there. Certain areas across Maui have restrictions on the number of days per year a home can be used as a short-term rental. Properties that offer stays under 180 days are considered short-term vacation rentals. They require a transient vacation rental permit to allow short-term rentals. Before committing to any one place, remember to speak to your Realtor to determine whether you can use your property as you’d like.

Find your next home in Wailea

Wailea is the perfect blend of beauty, bliss, and bustle, making it a lovely choice for any buyer’s next vacation property. If you’re interested in learning more about what Wailea real estate offers, work with local real estate broker Chelsea Dimin. With a specialization in luxury vacation properties across Maui, Chelsea is well-equipped to help clients find what they’re looking for. Contact Chelsea Dimin today.

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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