Using a 1031 Exchange on Maui to Leverage Up Without Losing Your Gains to Taxes

1031 Exchange Maui

From the stable cash flow of rental income to the exceptional growth of property value and more, Maui investment properties hold tremendous financial potential. When you sell a rental property or second home, you will ideally enjoy a handsome profit. As is the case with all types of income, Uncle Sam try to take a cut.

Depending on how much appreciation your subject property of the 1031 exchange has had, tax liabilities from selling can be substantial. So, you'll understandably want to avoid taxes, if possible, and maximize your return on your initial investment. Fortunately, you can do so legally with one of the largest wealth-building tools for real estate investors in the US tax code, the 1031 exchange. 

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Understanding Capital Gains Taxation

The federal capital gains tax is considerable and is based on how profitable your investment was and how long you owned the property. Profit is calculated by the difference between the original purchase price and your net sales price minus the cost of improvements. How longed you have owned the property also matters. If you own your investment property on Maui or anywhere else for less than 12 months, your financial gain is taxed at your current ordinary income tax level.

High earners may pay as much as 37 percent on short-term capital gains. If you own the property for less than 12 months, your current income tax bracket will determine the rate you will pay. The highest capital gains tax rate for long-term investments held for more than 12 months is 20 percent.  

Enjoying Appreciation By Reinvesting

A significant financial benefit associated with investing in real estate is appreciation. Unfortunately, the capital gains tax can take away up to 37 percent of that appreciation. The 1031 exchange allows a property owner to participate in a “like-kind exchange,” which requires the seller to reinvest the gains on a replacement property by closing on it within 6 months of the subject property.

By doing so, you can continue building your real estate portfolio without unnecessary taxation. However, you will eventually cash out of your investments, and capital gains tax may be due then. Through one or more 1031 exchanges, however, you may dramatically reduce your overall tax liability over the years. This enables you to build wealth continuously and rapidly.

The Benefits of a 1031 Exchange 

Kapalua Condos For Sale

A 1031 exchange, which is named after the IRS code’s Section 1031, essentially enables you to swap one investment for another similar investment without concern for taxation. There are specific rules and requirements that must be met.

One of the reasons why many people do not take advantage of a 1031 exchange’s benefits is that the rules and requirements may seem onerous.

However, given the ability to potentially save a six-figure sum of money or more, the effort is worthwhile, and the purchase process does not differ substantially from buying with cash or a loan. It just requires retaining a skilled, experienced real estate agent and 1031 intermediary for the process, and having the escrow/title agent be experienced as well. 

Hoolei Condos For Sale

A common real estate investment strategy is to gradually move up to larger, more lucrative properties. For example, an investor may hold a small residential investment property for a few years before selling it for a profit.

The investor may then use the cash proceeds as a down payment on a short-term rentable condo in Kapalua, or on a rental home in Kula, for example.

This process may be repeated with progressively larger and more valuable real estate investments. When the government dips its hand into the pool of cash proceeds between each transaction, your reinvestment capabilities are diminished.

When this diminishment persists across multiple transactions over the years, the impact on your net worth and real estate income can be incredible. You probably already know all of this, though, so let's get into the details and how to make sure you complete the process successfully. 

Most Recently Closed Properties on Maui

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Sold
Closed: 04/20/2026
Listing Image for 79 Kapihaa Pl 2b 1 of 23 Listing Image for 79 Kapihaa Pl 2b 2 of 23 Listing Image for 79 Kapihaa Pl 2b 3 of 23 Listing Image for 79 Kapihaa Pl 2b 4 of 23 Listing Image for 79 Kapihaa Pl 2b 5 of 23 Listing Image for 79 Kapihaa Pl 2b 6 of 23 Listing Image for 79 Kapihaa Pl 2b 7 of 23 Listing Image for 79 Kapihaa Pl 2b 8 of 23 Listing Image for 79 Kapihaa Pl 2b 9 of 23 Listing Image for 79 Kapihaa Pl 2b 10 of 23 Listing Image for 79 Kapihaa Pl 2b 11 of 23 Listing Image for 79 Kapihaa Pl 2b 12 of 23 Listing Image for 79 Kapihaa Pl 2b 13 of 23 Listing Image for 79 Kapihaa Pl 2b 14 of 23 Listing Image for 79 Kapihaa Pl 2b 15 of 23 Listing Image for 79 Kapihaa Pl 2b 16 of 23 Listing Image for 79 Kapihaa Pl 2b 17 of 23 Listing Image for 79 Kapihaa Pl 2b 18 of 23 Listing Image for 79 Kapihaa Pl 2b 19 of 23 Listing Image for 79 Kapihaa Pl 2b 20 of 23 Listing Image for 79 Kapihaa Pl 2b 21 of 23 Listing Image for 79 Kapihaa Pl 2b 22 of 23 Listing Image for 79 Kapihaa Pl 2b 23 of 23

$2,575,000

Terraces Manele Bay 2B

79 Kapihaa Pl 2b, Lanai

2 Beds 2.5 Baths 1,972 SqFt Residential MLS® # 408537 Date Sold: April 20, 2026
Sold
Closed: 04/24/2026
Listing Image for 3788 Lower Honoapiilani Rd A210 1 of 5 Listing Image for 3788 Lower Honoapiilani Rd A210 2 of 5 Listing Image for 3788 Lower Honoapiilani Rd A210 3 of 5 Listing Image for 3788 Lower Honoapiilani Rd A210 4 of 5 Listing Image for 3788 Lower Honoapiilani Rd A210 5 of 5

$350,000

↓ $138,000

Hale Royale A210

3788 Lower Honoapiilani Rd A210, Napili/Kahana/Honokowai

1 Bed 2 Baths 790 SqFt Residential MLS® # 408261 Date Sold: April 24, 2026
Sold
Closed: 03/20/2026
Listing Image for 155 Wailea Ike Pl 65 1 of 37 Listing Image for 155 Wailea Ike Pl 65 2 of 37 Listing Image for 155 Wailea Ike Pl 65 3 of 37 Listing Image for 155 Wailea Ike Pl 65 4 of 37 Listing Image for 155 Wailea Ike Pl 65 5 of 37 Listing Image for 155 Wailea Ike Pl 65 6 of 37 Listing Image for 155 Wailea Ike Pl 65 7 of 37 Listing Image for 155 Wailea Ike Pl 65 8 of 37 Listing Image for 155 Wailea Ike Pl 65 9 of 37 Listing Image for 155 Wailea Ike Pl 65 10 of 37 Listing Image for 155 Wailea Ike Pl 65 11 of 37 Listing Image for 155 Wailea Ike Pl 65 12 of 37 Listing Image for 155 Wailea Ike Pl 65 13 of 37 Listing Image for 155 Wailea Ike Pl 65 14 of 37 Listing Image for 155 Wailea Ike Pl 65 15 of 37 Listing Image for 155 Wailea Ike Pl 65 16 of 37 Listing Image for 155 Wailea Ike Pl 65 17 of 37 Listing Image for 155 Wailea Ike Pl 65 18 of 37 Listing Image for 155 Wailea Ike Pl 65 19 of 37 Listing Image for 155 Wailea Ike Pl 65 20 of 37 Listing Image for 155 Wailea Ike Pl 65 21 of 37 Listing Image for 155 Wailea Ike Pl 65 22 of 37 Listing Image for 155 Wailea Ike Pl 65 23 of 37 Listing Image for 155 Wailea Ike Pl 65 24 of 37 Listing Image for 155 Wailea Ike Pl 65 25 of 37 Listing Image for 155 Wailea Ike Pl 65 26 of 37 Listing Image for 155 Wailea Ike Pl 65 27 of 37 Listing Image for 155 Wailea Ike Pl 65 28 of 37 Listing Image for 155 Wailea Ike Pl 65 29 of 37 Listing Image for 155 Wailea Ike Pl 65 30 of 37 Listing Image for 155 Wailea Ike Pl 65 31 of 37 Listing Image for 155 Wailea Ike Pl 65 32 of 37 Listing Image for 155 Wailea Ike Pl 65 33 of 37 Listing Image for 155 Wailea Ike Pl 65 34 of 37 Listing Image for 155 Wailea Ike Pl 65 35 of 37 Listing Image for 155 Wailea Ike Pl 65 36 of 37 Listing Image for 155 Wailea Ike Pl 65 37 of 37

$945,000

Grand Champions 65

155 Wailea Ike Pl 65, Wailea/Makena

2 Beds 2 Baths 1,056 SqFt Residential MLS® # 408285 Date Sold: March 20, 2026
Sold
Closed: 04/27/2026
Listing Image for 130 Kai Malina Pkwy Sr538 1 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 2 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 3 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 4 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 5 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 6 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 7 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 8 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 9 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 10 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 11 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 12 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 13 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 14 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 15 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 16 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 17 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 18 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 19 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 20 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 21 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 22 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 23 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 24 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 25 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 26 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 27 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 28 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 29 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 30 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 31 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 32 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 33 of 34 Listing Image for 130 Kai Malina Pkwy Sr538 34 of 34

$1,200,000

↓ $200,000

Honua Kai - Hoku Lani SR538

130 Kai Malina Pkwy Sr538, Kaanapali

1 Bed 1 Bath 700 SqFt Residential MLS® # 408479 Date Sold: April 27, 2026
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Sold
Closed: 02/27/2026
Listing Image for 170 Kualapa Pl 70 1 of 50 Listing Image for 170 Kualapa Pl 70 2 of 50 Listing Image for 170 Kualapa Pl 70 3 of 50 Listing Image for 170 Kualapa Pl 70 4 of 50 Listing Image for 170 Kualapa Pl 70 5 of 50 Listing Image for 170 Kualapa Pl 70 6 of 50 Listing Image for 170 Kualapa Pl 70 7 of 50 Listing Image for 170 Kualapa Pl 70 8 of 50 Listing Image for 170 Kualapa Pl 70 9 of 50 Listing Image for 170 Kualapa Pl 70 10 of 50 Listing Image for 170 Kualapa Pl 70 11 of 50 Listing Image for 170 Kualapa Pl 70 12 of 50 Listing Image for 170 Kualapa Pl 70 13 of 50 Listing Image for 170 Kualapa Pl 70 14 of 50 Listing Image for 170 Kualapa Pl 70 15 of 50 Listing Image for 170 Kualapa Pl 70 16 of 50 Listing Image for 170 Kualapa Pl 70 17 of 50 Listing Image for 170 Kualapa Pl 70 18 of 50 Listing Image for 170 Kualapa Pl 70 19 of 50 Listing Image for 170 Kualapa Pl 70 20 of 50 Listing Image for 170 Kualapa Pl 70 21 of 50 Listing Image for 170 Kualapa Pl 70 22 of 50 Listing Image for 170 Kualapa Pl 70 23 of 50 Listing Image for 170 Kualapa Pl 70 24 of 50 Listing Image for 170 Kualapa Pl 70 25 of 50 Listing Image for 170 Kualapa Pl 70 26 of 50 Listing Image for 170 Kualapa Pl 70 27 of 50 Listing Image for 170 Kualapa Pl 70 28 of 50 Listing Image for 170 Kualapa Pl 70 29 of 50 Listing Image for 170 Kualapa Pl 70 30 of 50 Listing Image for 170 Kualapa Pl 70 31 of 50 Listing Image for 170 Kualapa Pl 70 32 of 50 Listing Image for 170 Kualapa Pl 70 33 of 50 Listing Image for 170 Kualapa Pl 70 34 of 50 Listing Image for 170 Kualapa Pl 70 35 of 50 Listing Image for 170 Kualapa Pl 70 36 of 50 Listing Image for 170 Kualapa Pl 70 37 of 50 Listing Image for 170 Kualapa Pl 70 38 of 50 Listing Image for 170 Kualapa Pl 70 39 of 50 Listing Image for 170 Kualapa Pl 70 40 of 50 Listing Image for 170 Kualapa Pl 70 41 of 50 Listing Image for 170 Kualapa Pl 70 42 of 50 Listing Image for 170 Kualapa Pl 70 43 of 50 Listing Image for 170 Kualapa Pl 70 44 of 50 Listing Image for 170 Kualapa Pl 70 45 of 50 Listing Image for 170 Kualapa Pl 70 46 of 50 Listing Image for 170 Kualapa Pl 70 47 of 50 Listing Image for 170 Kualapa Pl 70 48 of 50 Listing Image for 170 Kualapa Pl 70 49 of 50 Listing Image for 170 Kualapa Pl 70 50 of 50

$1,895,000

Vintage at Kaanapali 70

170 Kualapa Pl 70, Kaanapali

3 Beds 2.5 Baths 1,799 SqFt Residential MLS® # 408315 Date Sold: February 27, 2026
Sold
Closed: 12/01/2025
721 Mill St, Lahaina

$608,000

Lahaina

721 Mill St, Lahaina

0 Beds 0 Baths 0 SqFt Land MLS® # 408323 Date Sold: December 1, 2025
Sold
Closed: 10/14/2026
Listing Image for 2747 S Kihei Rd B203 1 of 44 Listing Image for 2747 S Kihei Rd B203 2 of 44 Listing Image for 2747 S Kihei Rd B203 3 of 44 Listing Image for 2747 S Kihei Rd B203 4 of 44 Listing Image for 2747 S Kihei Rd B203 5 of 44 Listing Image for 2747 S Kihei Rd B203 6 of 44 Listing Image for 2747 S Kihei Rd B203 7 of 44 Listing Image for 2747 S Kihei Rd B203 8 of 44 Listing Image for 2747 S Kihei Rd B203 9 of 44 Listing Image for 2747 S Kihei Rd B203 10 of 44 Listing Image for 2747 S Kihei Rd B203 11 of 44 Listing Image for 2747 S Kihei Rd B203 12 of 44 Listing Image for 2747 S Kihei Rd B203 13 of 44 Listing Image for 2747 S Kihei Rd B203 14 of 44 Listing Image for 2747 S Kihei Rd B203 15 of 44 Listing Image for 2747 S Kihei Rd B203 16 of 44 Listing Image for 2747 S Kihei Rd B203 17 of 44 Listing Image for 2747 S Kihei Rd B203 18 of 44 Listing Image for 2747 S Kihei Rd B203 19 of 44 Listing Image for 2747 S Kihei Rd B203 20 of 44 Listing Image for 2747 S Kihei Rd B203 21 of 44 Listing Image for 2747 S Kihei Rd B203 22 of 44 Listing Image for 2747 S Kihei Rd B203 23 of 44 Listing Image for 2747 S Kihei Rd B203 24 of 44 Listing Image for 2747 S Kihei Rd B203 25 of 44 Listing Image for 2747 S Kihei Rd B203 26 of 44 Listing Image for 2747 S Kihei Rd B203 27 of 44 Listing Image for 2747 S Kihei Rd B203 28 of 44 Listing Image for 2747 S Kihei Rd B203 29 of 44 Listing Image for 2747 S Kihei Rd B203 30 of 44 Listing Image for 2747 S Kihei Rd B203 31 of 44 Listing Image for 2747 S Kihei Rd B203 32 of 44 Listing Image for 2747 S Kihei Rd B203 33 of 44 Listing Image for 2747 S Kihei Rd B203 34 of 44 Listing Image for 2747 S Kihei Rd B203 35 of 44 Listing Image for 2747 S Kihei Rd B203 36 of 44 Listing Image for 2747 S Kihei Rd B203 37 of 44 Listing Image for 2747 S Kihei Rd B203 38 of 44 Listing Image for 2747 S Kihei Rd B203 39 of 44 Listing Image for 2747 S Kihei Rd B203 40 of 44 Listing Image for 2747 S Kihei Rd B203 41 of 44 Listing Image for 2747 S Kihei Rd B203 42 of 44 Listing Image for 2747 S Kihei Rd B203 43 of 44 Listing Image for 2747 S Kihei Rd B203 44 of 44

$440,000

↓ $109,000

Kihei Shores B203

2747 S Kihei Rd B203, Kihei

2 Beds 2 Baths 719 SqFt Residential MLS® # 408452 Date Sold: October 14, 2026
Sold
Closed: 12/01/2025
915 Puiki Pl, Lahaina

$424,000

Lahaina

915 Puiki Pl, Lahaina

0 Beds 0 Baths 0 SqFt Land MLS® # 408320 Date Sold: December 1, 2025
View 8 More Listings

Requirements for a 1031 Exchange on Maui

What does it take to protect your wealth through a 1031 exchange on Maui? The most common type of 1031 exchange is a delayed exchange. With this type of exchange, you are given 45 days after the sale of one property to identify a “like-kind” property that you want to invest in.

To comply with the IRS’s tax guidelines, you must then close on the property you identified within 180 days of the sale of the original property.

West Maui Condos For Sale

The IRS code specifically states that a 1031 exchange is for similar investments only. This may sound constricting, but it actually is a very lenient rule. For example, you can exchange a small apartment complex for a large retail center or a plot of land for an office building investment, a condo for a home, etc.

Essentially, you must exchange a real estate investment for a real estate investment. Keep in mind that a 1031 exchange does not pertain to a personal residence, but there is a loophole for exchanging vacation homes. The 1031 exchange addendum is added to the Hawaii Purchase Contract and is coordinated by the intermediary assigned during escrow.

The Exchange Process

A delayed 1031 exchange is completed through a qualified intermediary, also known as a QI. You must set up the 1031 exchange before the sale of your original subject property has been finalized. The funds from that sale will be transferred immediately to a holding account via the qualified intermediary.

It can take time and leverage to secure suitable investment properties on Maui, so your search for a replacement property should begin before the sale of the relinquished property is finalized. However, you have 45 days to identify the property that you wish to buy.

Be aware that you must notify the IRS of the property that you intend to buy, and that must be the property that you eventually close on. You may actually choose up to three properties, and you must close on one of the identified properties to avoid paying capital gains tax.

You will then walk through the purchase process for the new property as you normally would. The seller will sign a disclosure related to the 1031 exchange upfront, but all other aspects of the purchase will proceed as usual. At closing, the QI will disperse the held funds directly to the closing agent, and the transaction will be complete.

Different Types of 1031 Exchanges

The other types of 1031 exchanges are reverse exchanges, simultaneous exchanges, and improvement exchanges. A reverse 1031 exchange occurs when the investor purchases the replacement property before selling the relinquished property. A simultaneous exchange is when the relinquished property is sold at the same time the replacement property is purchased.

An improvement exchange enables the investor to use the proceeds from the relinquished property to make capital improvements on the replacement property.

In Conclusion

While a 1031 exchange on Maui or anywhere else requires extra effort and inevitably involves more paperwork, the effort can be well-rewarded. Using a skilled realtor with 1031 experience will be a great help, of course.  Keep in mind that there is no limit to the number of 1031 exchanges you can do.

I have extensive experience representing clients exchanging into and out of Maui. If you are interested in a 1031 exchange,  please reach out to me, and I can connect you with my preferred qualified intermediaries, who can answer your questions and guide you through the process seamlessly. 

Get In Touch With Evan!

Evan Harlow Maui

Evan Harlow ranks among the best real estate agents on Maui annually and is in the top 1% of Coldwell Banker agents worldwide in production. Evan has the expertise, experience, and work ethic to help you achieve your real estate buying and selling goals. We promise exceptional service and support from the beginning of the process through closing and beyond. See what Evan's clients are saying on Google.

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