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. 

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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: 06/12/2026
Listing Image for 110 Kaanapali Shores Pl 311 1 of 37 Listing Image for 110 Kaanapali Shores Pl 311 2 of 37 Listing Image for 110 Kaanapali Shores Pl 311 3 of 37 Listing Image for 110 Kaanapali Shores Pl 311 4 of 37 Listing Image for 110 Kaanapali Shores Pl 311 5 of 37 Listing Image for 110 Kaanapali Shores Pl 311 6 of 37 Listing Image for 110 Kaanapali Shores Pl 311 7 of 37 Listing Image for 110 Kaanapali Shores Pl 311 8 of 37 Listing Image for 110 Kaanapali Shores Pl 311 9 of 37 Listing Image for 110 Kaanapali Shores Pl 311 10 of 37 Listing Image for 110 Kaanapali Shores Pl 311 11 of 37 Listing Image for 110 Kaanapali Shores Pl 311 12 of 37 Listing Image for 110 Kaanapali Shores Pl 311 13 of 37 Listing Image for 110 Kaanapali Shores Pl 311 14 of 37 Listing Image for 110 Kaanapali Shores Pl 311 15 of 37 Listing Image for 110 Kaanapali Shores Pl 311 16 of 37 Listing Image for 110 Kaanapali Shores Pl 311 17 of 37 Listing Image for 110 Kaanapali Shores Pl 311 18 of 37 Listing Image for 110 Kaanapali Shores Pl 311 19 of 37 Listing Image for 110 Kaanapali Shores Pl 311 20 of 37 Listing Image for 110 Kaanapali Shores Pl 311 21 of 37 Listing Image for 110 Kaanapali Shores Pl 311 22 of 37 Listing Image for 110 Kaanapali Shores Pl 311 23 of 37 Listing Image for 110 Kaanapali Shores Pl 311 24 of 37 Listing Image for 110 Kaanapali Shores Pl 311 25 of 37 Listing Image for 110 Kaanapali Shores Pl 311 26 of 37 Listing Image for 110 Kaanapali Shores Pl 311 27 of 37 Listing Image for 110 Kaanapali Shores Pl 311 28 of 37 Listing Image for 110 Kaanapali Shores Pl 311 29 of 37 Listing Image for 110 Kaanapali Shores Pl 311 30 of 37 Listing Image for 110 Kaanapali Shores Pl 311 31 of 37 Listing Image for 110 Kaanapali Shores Pl 311 32 of 37 Listing Image for 110 Kaanapali Shores Pl 311 33 of 37 Listing Image for 110 Kaanapali Shores Pl 311 34 of 37 Listing Image for 110 Kaanapali Shores Pl 311 35 of 37 Listing Image for 110 Kaanapali Shores Pl 311 36 of 37 Listing Image for 110 Kaanapali Shores Pl 311 37 of 37

$1,560,000

↓ $390,000

Mahana 311

110 Kaanapali Shores Pl 311, Kaanapali

2 Beds 2 Baths 1,178 SqFt Residential MLS® # 407745 Date Sold: June 12, 2026
Sold
Closed: 01/28/2026
Listing Image for 3708 Lower Honoapiilani Rd E43 1 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 2 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 3 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 4 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 5 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 6 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 7 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 8 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 9 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 10 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 11 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 12 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 13 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 14 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 15 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 16 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 17 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 18 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 19 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 20 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 21 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 22 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 23 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 24 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 25 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 26 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 27 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 28 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 29 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 30 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 31 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 32 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 33 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 34 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 35 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 36 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 37 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 38 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 39 of 40 Listing Image for 3708 Lower Honoapiilani Rd E43 40 of 40

$610,000

The Breakers E43

3708 Lower Honoapiilani Rd E43, Napili/Kahana/Honokowai

2 Beds 1 Bath 809 SqFt Residential MLS® # 407844 Date Sold: January 28, 2026
Sold
Closed: 02/27/2026
Listing Image for 1002 S Kihei Rd 210 1 of 18 Listing Image for 1002 S Kihei Rd 210 2 of 18 Listing Image for 1002 S Kihei Rd 210 3 of 18 Listing Image for 1002 S Kihei Rd 210 4 of 18 Listing Image for 1002 S Kihei Rd 210 5 of 18 Listing Image for 1002 S Kihei Rd 210 6 of 18 Listing Image for 1002 S Kihei Rd 210 7 of 18 Listing Image for 1002 S Kihei Rd 210 8 of 18 Listing Image for 1002 S Kihei Rd 210 9 of 18 Listing Image for 1002 S Kihei Rd 210 10 of 18 Listing Image for 1002 S Kihei Rd 210 11 of 18 Listing Image for 1002 S Kihei Rd 210 12 of 18 Listing Image for 1002 S Kihei Rd 210 13 of 18 Listing Image for 1002 S Kihei Rd 210 14 of 18 Listing Image for 1002 S Kihei Rd 210 15 of 18 Listing Image for 1002 S Kihei Rd 210 16 of 18 Listing Image for 1002 S Kihei Rd 210 17 of 18 Listing Image for 1002 S Kihei Rd 210 18 of 18

$335,000

↓ $64,000

Waipuilani 210

1002 S Kihei Rd 210, Kihei

1 Bed 1 Bath 520 SqFt Residential MLS® # 407833 Date Sold: February 27, 2026
Sold
Closed: 02/12/2026
Listing Image for 707 Noweo Pl 1 of 23 Listing Image for 707 Noweo Pl 2 of 23 Listing Image for 707 Noweo Pl 3 of 23 Listing Image for 707 Noweo Pl 4 of 23 Listing Image for 707 Noweo Pl 5 of 23 Listing Image for 707 Noweo Pl 6 of 23 Listing Image for 707 Noweo Pl 7 of 23 Listing Image for 707 Noweo Pl 8 of 23 Listing Image for 707 Noweo Pl 9 of 23 Listing Image for 707 Noweo Pl 10 of 23 Listing Image for 707 Noweo Pl 11 of 23 Listing Image for 707 Noweo Pl 12 of 23 Listing Image for 707 Noweo Pl 13 of 23 Listing Image for 707 Noweo Pl 14 of 23 Listing Image for 707 Noweo Pl 15 of 23 Listing Image for 707 Noweo Pl 16 of 23 Listing Image for 707 Noweo Pl 17 of 23 Listing Image for 707 Noweo Pl 18 of 23 Listing Image for 707 Noweo Pl 19 of 23 Listing Image for 707 Noweo Pl 20 of 23 Listing Image for 707 Noweo Pl 21 of 23 Listing Image for 707 Noweo Pl 22 of 23 Listing Image for 707 Noweo Pl 23 of 23

$620,000

Wailuku

707 Noweo Pl, Wailuku

0 Beds 0 Baths 0 SqFt Land MLS® # 407566 Date Sold: February 12, 2026
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Sold
Closed: 02/06/2026
Listing Image for 106 Kaanapali Shores Pl 405 1 of 48 Listing Image for 106 Kaanapali Shores Pl 405 2 of 48 Listing Image for 106 Kaanapali Shores Pl 405 3 of 48 Listing Image for 106 Kaanapali Shores Pl 405 4 of 48 Listing Image for 106 Kaanapali Shores Pl 405 5 of 48 Listing Image for 106 Kaanapali Shores Pl 405 6 of 48 Listing Image for 106 Kaanapali Shores Pl 405 7 of 48 Listing Image for 106 Kaanapali Shores Pl 405 8 of 48 Listing Image for 106 Kaanapali Shores Pl 405 9 of 48 Listing Image for 106 Kaanapali Shores Pl 405 10 of 48 Listing Image for 106 Kaanapali Shores Pl 405 11 of 48 Listing Image for 106 Kaanapali Shores Pl 405 12 of 48 Listing Image for 106 Kaanapali Shores Pl 405 13 of 48 Listing Image for 106 Kaanapali Shores Pl 405 14 of 48 Listing Image for 106 Kaanapali Shores Pl 405 15 of 48 Listing Image for 106 Kaanapali Shores Pl 405 16 of 48 Listing Image for 106 Kaanapali Shores Pl 405 17 of 48 Listing Image for 106 Kaanapali Shores Pl 405 18 of 48 Listing Image for 106 Kaanapali Shores Pl 405 19 of 48 Listing Image for 106 Kaanapali Shores Pl 405 20 of 48 Listing Image for 106 Kaanapali Shores Pl 405 21 of 48 Listing Image for 106 Kaanapali Shores Pl 405 22 of 48 Listing Image for 106 Kaanapali Shores Pl 405 23 of 48 Listing Image for 106 Kaanapali Shores Pl 405 24 of 48 Listing Image for 106 Kaanapali Shores Pl 405 25 of 48 Listing Image for 106 Kaanapali Shores Pl 405 26 of 48 Listing Image for 106 Kaanapali Shores Pl 405 27 of 48 Listing Image for 106 Kaanapali Shores Pl 405 28 of 48 Listing Image for 106 Kaanapali Shores Pl 405 29 of 48 Listing Image for 106 Kaanapali Shores Pl 405 30 of 48 Listing Image for 106 Kaanapali Shores Pl 405 31 of 48 Listing Image for 106 Kaanapali Shores Pl 405 32 of 48 Listing Image for 106 Kaanapali Shores Pl 405 33 of 48 Listing Image for 106 Kaanapali Shores Pl 405 34 of 48 Listing Image for 106 Kaanapali Shores Pl 405 35 of 48 Listing Image for 106 Kaanapali Shores Pl 405 36 of 48 Listing Image for 106 Kaanapali Shores Pl 405 37 of 48 Listing Image for 106 Kaanapali Shores Pl 405 38 of 48 Listing Image for 106 Kaanapali Shores Pl 405 39 of 48 Listing Image for 106 Kaanapali Shores Pl 405 40 of 48 Listing Image for 106 Kaanapali Shores Pl 405 41 of 48 Listing Image for 106 Kaanapali Shores Pl 405 42 of 48 Listing Image for 106 Kaanapali Shores Pl 405 43 of 48 Listing Image for 106 Kaanapali Shores Pl 405 44 of 48 Listing Image for 106 Kaanapali Shores Pl 405 45 of 48 Listing Image for 106 Kaanapali Shores Pl 405 46 of 48 Listing Image for 106 Kaanapali Shores Pl 405 47 of 48 Listing Image for 106 Kaanapali Shores Pl 405 48 of 48

$910,000

Maui Kai 405

106 Kaanapali Shores Pl 405, Kaanapali

1 Bed 1 Bath 647 SqFt Residential MLS® # 407725 Date Sold: February 6, 2026
Sold
Closed: 01/26/2026
Listing Image for 00 Hauola Pl 1 of 5 Listing Image for 00 Hauola Pl 2 of 5 Listing Image for 00 Hauola Pl 3 of 5 Listing Image for 00 Hauola Pl 4 of 5 Listing Image for 00 Hauola Pl 5 of 5

$630,000

Lahaina

00 Hauola Pl, Lahaina

0 Beds 0 Baths 0 SqFt Land MLS® # 407815 Date Sold: January 26, 2026
Sold
Closed: 06/26/2026
Listing Image for 641 Hihimanu St 28 1 of 42 Listing Image for 641 Hihimanu St 28 2 of 42 Listing Image for 641 Hihimanu St 28 3 of 42 Listing Image for 641 Hihimanu St 28 4 of 42 Listing Image for 641 Hihimanu St 28 5 of 42 Listing Image for 641 Hihimanu St 28 6 of 42 Listing Image for 641 Hihimanu St 28 7 of 42 Listing Image for 641 Hihimanu St 28 8 of 42 Listing Image for 641 Hihimanu St 28 9 of 42 Listing Image for 641 Hihimanu St 28 10 of 42 Listing Image for 641 Hihimanu St 28 11 of 42 Listing Image for 641 Hihimanu St 28 12 of 42 Listing Image for 641 Hihimanu St 28 13 of 42 Listing Image for 641 Hihimanu St 28 14 of 42 Listing Image for 641 Hihimanu St 28 15 of 42 Listing Image for 641 Hihimanu St 28 16 of 42 Listing Image for 641 Hihimanu St 28 17 of 42 Listing Image for 641 Hihimanu St 28 18 of 42 Listing Image for 641 Hihimanu St 28 19 of 42 Listing Image for 641 Hihimanu St 28 20 of 42 Listing Image for 641 Hihimanu St 28 21 of 42 Listing Image for 641 Hihimanu St 28 22 of 42 Listing Image for 641 Hihimanu St 28 23 of 42 Listing Image for 641 Hihimanu St 28 24 of 42 Listing Image for 641 Hihimanu St 28 25 of 42 Listing Image for 641 Hihimanu St 28 26 of 42 Listing Image for 641 Hihimanu St 28 27 of 42 Listing Image for 641 Hihimanu St 28 28 of 42 Listing Image for 641 Hihimanu St 28 29 of 42 Listing Image for 641 Hihimanu St 28 30 of 42 Listing Image for 641 Hihimanu St 28 31 of 42 Listing Image for 641 Hihimanu St 28 32 of 42 Listing Image for 641 Hihimanu St 28 33 of 42 Listing Image for 641 Hihimanu St 28 34 of 42 Listing Image for 641 Hihimanu St 28 35 of 42 Listing Image for 641 Hihimanu St 28 36 of 42 Listing Image for 641 Hihimanu St 28 37 of 42 Listing Image for 641 Hihimanu St 28 38 of 42 Listing Image for 641 Hihimanu St 28 39 of 42 Listing Image for 641 Hihimanu St 28 40 of 42 Listing Image for 641 Hihimanu St 28 41 of 42 Listing Image for 641 Hihimanu St 28 42 of 42

$1,585,000

↓ $165,000

Hokulani Golf Villas 28

641 Hihimanu St 28, Kihei

2 Beds 2 Baths 1,831 SqFt Residential MLS® # 407700 Date Sold: June 26, 2026
Sold
Closed: 11/07/2025
402 Puaehu St, Wailuku

$1,445,000

Ilima at Kehalani

402 Puaehu St, Wailuku

3 Beds 2 Baths 1,845 SqFt Residential MLS® # 407670 Date Sold: November 7, 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. 

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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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