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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New Sold
Closed: 03/12/2026
Listing Image for 16 Kai Makani Loop 202 1 of 10 Listing Image for 16 Kai Makani Loop 202 2 of 10 Listing Image for 16 Kai Makani Loop 202 3 of 10 Listing Image for 16 Kai Makani Loop 202 4 of 10 Listing Image for 16 Kai Makani Loop 202 5 of 10 Listing Image for 16 Kai Makani Loop 202 6 of 10 Listing Image for 16 Kai Makani Loop 202 7 of 10 Listing Image for 16 Kai Makani Loop 202 8 of 10 Listing Image for 16 Kai Makani Loop 202 9 of 10 Listing Image for 16 Kai Makani Loop 202 10 of 10

$1,258,000

Kai Makani 202

16 Kai Makani Loop 202, Kihei

3 Beds 2 Baths 1,238 SqFt Residential MLS® # 409022 Date Sold: March 12, 2026
New Sold
Closed: 06/10/2026
Listing Image for 4400 Makena Rd 107 1 of 42 Listing Image for 4400 Makena Rd 107 2 of 42 Listing Image for 4400 Makena Rd 107 3 of 42 Listing Image for 4400 Makena Rd 107 4 of 42 Listing Image for 4400 Makena Rd 107 5 of 42 Listing Image for 4400 Makena Rd 107 6 of 42 Listing Image for 4400 Makena Rd 107 7 of 42 Listing Image for 4400 Makena Rd 107 8 of 42 Listing Image for 4400 Makena Rd 107 9 of 42 Listing Image for 4400 Makena Rd 107 10 of 42 Listing Image for 4400 Makena Rd 107 11 of 42 Listing Image for 4400 Makena Rd 107 12 of 42 Listing Image for 4400 Makena Rd 107 13 of 42 Listing Image for 4400 Makena Rd 107 14 of 42 Listing Image for 4400 Makena Rd 107 15 of 42 Listing Image for 4400 Makena Rd 107 16 of 42 Listing Image for 4400 Makena Rd 107 17 of 42 Listing Image for 4400 Makena Rd 107 18 of 42 Listing Image for 4400 Makena Rd 107 19 of 42 Listing Image for 4400 Makena Rd 107 20 of 42 Listing Image for 4400 Makena Rd 107 21 of 42 Listing Image for 4400 Makena Rd 107 22 of 42 Listing Image for 4400 Makena Rd 107 23 of 42 Listing Image for 4400 Makena Rd 107 24 of 42 Listing Image for 4400 Makena Rd 107 25 of 42 Listing Image for 4400 Makena Rd 107 26 of 42 Listing Image for 4400 Makena Rd 107 27 of 42 Listing Image for 4400 Makena Rd 107 28 of 42 Listing Image for 4400 Makena Rd 107 29 of 42 Listing Image for 4400 Makena Rd 107 30 of 42 Listing Image for 4400 Makena Rd 107 31 of 42 Listing Image for 4400 Makena Rd 107 32 of 42 Listing Image for 4400 Makena Rd 107 33 of 42 Listing Image for 4400 Makena Rd 107 34 of 42 Listing Image for 4400 Makena Rd 107 35 of 42 Listing Image for 4400 Makena Rd 107 36 of 42 Listing Image for 4400 Makena Rd 107 37 of 42 Listing Image for 4400 Makena Rd 107 38 of 42 Listing Image for 4400 Makena Rd 107 39 of 42 Listing Image for 4400 Makena Rd 107 40 of 42 Listing Image for 4400 Makena Rd 107 41 of 42 Listing Image for 4400 Makena Rd 107 42 of 42

$3,750,000

Polo Beach Club 107

4400 Makena Rd 107, Wailea/Makena

2 Beds 2 Baths 1,186 SqFt Residential MLS® # 408915 Date Sold: June 10, 2026
New Sold
Closed: 07/09/2026
Listing Image for 480 Kenolio Rd 4-206 1 of 44 Listing Image for 480 Kenolio Rd 4-206 2 of 44 Listing Image for 480 Kenolio Rd 4-206 3 of 44 Listing Image for 480 Kenolio Rd 4-206 4 of 44 Listing Image for 480 Kenolio Rd 4-206 5 of 44 Listing Image for 480 Kenolio Rd 4-206 6 of 44 Listing Image for 480 Kenolio Rd 4-206 7 of 44 Listing Image for 480 Kenolio Rd 4-206 8 of 44 Listing Image for 480 Kenolio Rd 4-206 9 of 44 Listing Image for 480 Kenolio Rd 4-206 10 of 44 Listing Image for 480 Kenolio Rd 4-206 11 of 44 Listing Image for 480 Kenolio Rd 4-206 12 of 44 Listing Image for 480 Kenolio Rd 4-206 13 of 44 Listing Image for 480 Kenolio Rd 4-206 14 of 44 Listing Image for 480 Kenolio Rd 4-206 15 of 44 Listing Image for 480 Kenolio Rd 4-206 16 of 44 Listing Image for 480 Kenolio Rd 4-206 17 of 44 Listing Image for 480 Kenolio Rd 4-206 18 of 44 Listing Image for 480 Kenolio Rd 4-206 19 of 44 Listing Image for 480 Kenolio Rd 4-206 20 of 44 Listing Image for 480 Kenolio Rd 4-206 21 of 44 Listing Image for 480 Kenolio Rd 4-206 22 of 44 Listing Image for 480 Kenolio Rd 4-206 23 of 44 Listing Image for 480 Kenolio Rd 4-206 24 of 44 Listing Image for 480 Kenolio Rd 4-206 25 of 44 Listing Image for 480 Kenolio Rd 4-206 26 of 44 Listing Image for 480 Kenolio Rd 4-206 27 of 44 Listing Image for 480 Kenolio Rd 4-206 28 of 44 Listing Image for 480 Kenolio Rd 4-206 29 of 44 Listing Image for 480 Kenolio Rd 4-206 30 of 44 Listing Image for 480 Kenolio Rd 4-206 31 of 44 Listing Image for 480 Kenolio Rd 4-206 32 of 44 Listing Image for 480 Kenolio Rd 4-206 33 of 44 Listing Image for 480 Kenolio Rd 4-206 34 of 44 Listing Image for 480 Kenolio Rd 4-206 35 of 44 Listing Image for 480 Kenolio Rd 4-206 36 of 44 Listing Image for 480 Kenolio Rd 4-206 37 of 44 Listing Image for 480 Kenolio Rd 4-206 38 of 44 Listing Image for 480 Kenolio Rd 4-206 39 of 44 Listing Image for 480 Kenolio Rd 4-206 40 of 44 Listing Image for 480 Kenolio Rd 4-206 41 of 44 Listing Image for 480 Kenolio Rd 4-206 42 of 44 Listing Image for 480 Kenolio Rd 4-206 43 of 44 Listing Image for 480 Kenolio Rd 4-206 44 of 44

$475,000

↓ $24,000

Southpointe at Waiakoa 4-206

480 Kenolio Rd 4-206, Kihei

2 Beds 1.5 Baths 750 SqFt Residential MLS® # 408845 Date Sold: July 9, 2026
New Sold
Closed: 03/16/2026
Listing Image for 50 Nohea Kai Dr 1-801 1 of 27 Listing Image for 50 Nohea Kai Dr 1-801 2 of 27 Listing Image for 50 Nohea Kai Dr 1-801 3 of 27 Listing Image for 50 Nohea Kai Dr 1-801 4 of 27 Listing Image for 50 Nohea Kai Dr 1-801 5 of 27 Listing Image for 50 Nohea Kai Dr 1-801 6 of 27 Listing Image for 50 Nohea Kai Dr 1-801 7 of 27 Listing Image for 50 Nohea Kai Dr 1-801 8 of 27 Listing Image for 50 Nohea Kai Dr 1-801 9 of 27 Listing Image for 50 Nohea Kai Dr 1-801 10 of 27 Listing Image for 50 Nohea Kai Dr 1-801 11 of 27 Listing Image for 50 Nohea Kai Dr 1-801 12 of 27 Listing Image for 50 Nohea Kai Dr 1-801 13 of 27 Listing Image for 50 Nohea Kai Dr 1-801 14 of 27 Listing Image for 50 Nohea Kai Dr 1-801 15 of 27 Listing Image for 50 Nohea Kai Dr 1-801 16 of 27 Listing Image for 50 Nohea Kai Dr 1-801 17 of 27 Listing Image for 50 Nohea Kai Dr 1-801 18 of 27 Listing Image for 50 Nohea Kai Dr 1-801 19 of 27 Listing Image for 50 Nohea Kai Dr 1-801 20 of 27 Listing Image for 50 Nohea Kai Dr 1-801 21 of 27 Listing Image for 50 Nohea Kai Dr 1-801 22 of 27 Listing Image for 50 Nohea Kai Dr 1-801 23 of 27 Listing Image for 50 Nohea Kai Dr 1-801 24 of 27 Listing Image for 50 Nohea Kai Dr 1-801 25 of 27 Listing Image for 50 Nohea Kai Dr 1-801 26 of 27 Listing Image for 50 Nohea Kai Dr 1-801 27 of 27

$2,180,000

Kaanapali Alii 1-801

50 Nohea Kai Dr 1-801, Kaanapali

1 Bed 2 Baths 1,441 SqFt Residential MLS® # 409051 Date Sold: March 16, 2026
New Sold
Closed: 03/20/2026
Listing Image for 133 Hoowaiwai Loop 2304 1 of 2 Listing Image for 133 Hoowaiwai Loop 2304 2 of 2

$720,000

Hoolea Terrace at Kehalani 2304

133 Hoowaiwai Loop 2304, Wailuku

3 Beds 2 Baths 953 SqFt Residential MLS® # 409077 Date Sold: March 20, 2026
New Sold
Closed: 06/25/2026
Listing Image for 50 Waipaa Ln 103 1 of 21 Listing Image for 50 Waipaa Ln 103 2 of 21 Listing Image for 50 Waipaa Ln 103 3 of 21 Listing Image for 50 Waipaa Ln 103 4 of 21 Listing Image for 50 Waipaa Ln 103 5 of 21 Listing Image for 50 Waipaa Ln 103 6 of 21 Listing Image for 50 Waipaa Ln 103 7 of 21 Listing Image for 50 Waipaa Ln 103 8 of 21 Listing Image for 50 Waipaa Ln 103 9 of 21 Listing Image for 50 Waipaa Ln 103 10 of 21 Listing Image for 50 Waipaa Ln 103 11 of 21 Listing Image for 50 Waipaa Ln 103 12 of 21 Listing Image for 50 Waipaa Ln 103 13 of 21 Listing Image for 50 Waipaa Ln 103 14 of 21 Listing Image for 50 Waipaa Ln 103 15 of 21 Listing Image for 50 Waipaa Ln 103 16 of 21 Listing Image for 50 Waipaa Ln 103 17 of 21 Listing Image for 50 Waipaa Ln 103 18 of 21 Listing Image for 50 Waipaa Ln 103 19 of 21 Listing Image for 50 Waipaa Ln 103 20 of 21 Listing Image for 50 Waipaa Ln 103 21 of 21

$500,000

Iao Parkside IV-A 103

50 Waipaa Ln 103, Wailuku

2 Beds 2 Baths 830 SqFt Residential MLS® # 409023 Date Sold: June 25, 2026
New Sold
Closed: 09/02/2026
Listing Image for 50 Hauoli St 106 1 of 24 Listing Image for 50 Hauoli St 106 2 of 24 Listing Image for 50 Hauoli St 106 3 of 24 Listing Image for 50 Hauoli St 106 4 of 24 Listing Image for 50 Hauoli St 106 5 of 24 Listing Image for 50 Hauoli St 106 6 of 24 Listing Image for 50 Hauoli St 106 7 of 24 Listing Image for 50 Hauoli St 106 8 of 24 Listing Image for 50 Hauoli St 106 9 of 24 Listing Image for 50 Hauoli St 106 10 of 24 Listing Image for 50 Hauoli St 106 11 of 24 Listing Image for 50 Hauoli St 106 12 of 24 Listing Image for 50 Hauoli St 106 13 of 24 Listing Image for 50 Hauoli St 106 14 of 24 Listing Image for 50 Hauoli St 106 15 of 24 Listing Image for 50 Hauoli St 106 16 of 24 Listing Image for 50 Hauoli St 106 17 of 24 Listing Image for 50 Hauoli St 106 18 of 24 Listing Image for 50 Hauoli St 106 19 of 24 Listing Image for 50 Hauoli St 106 20 of 24 Listing Image for 50 Hauoli St 106 21 of 24 Listing Image for 50 Hauoli St 106 22 of 24 Listing Image for 50 Hauoli St 106 23 of 24 Listing Image for 50 Hauoli St 106 24 of 24

$249,500

↓ $28,277

Milowai 106

50 Hauoli St 106, Maalaea

1 Bed 1 Bath 557 SqFt Residential MLS® # 408893 Date Sold: September 2, 2026
New Sold
Closed: 08/25/2026
Listing Image for 149 Luluka Pl 1 of 50 Listing Image for 149 Luluka Pl 2 of 50 Listing Image for 149 Luluka Pl 3 of 50 Listing Image for 149 Luluka Pl 4 of 50 Listing Image for 149 Luluka Pl 5 of 50 Listing Image for 149 Luluka Pl 6 of 50 Listing Image for 149 Luluka Pl 7 of 50 Listing Image for 149 Luluka Pl 8 of 50 Listing Image for 149 Luluka Pl 9 of 50 Listing Image for 149 Luluka Pl 10 of 50 Listing Image for 149 Luluka Pl 11 of 50 Listing Image for 149 Luluka Pl 12 of 50 Listing Image for 149 Luluka Pl 13 of 50 Listing Image for 149 Luluka Pl 14 of 50 Listing Image for 149 Luluka Pl 15 of 50 Listing Image for 149 Luluka Pl 16 of 50 Listing Image for 149 Luluka Pl 17 of 50 Listing Image for 149 Luluka Pl 18 of 50 Listing Image for 149 Luluka Pl 19 of 50 Listing Image for 149 Luluka Pl 20 of 50 Listing Image for 149 Luluka Pl 21 of 50 Listing Image for 149 Luluka Pl 22 of 50 Listing Image for 149 Luluka Pl 23 of 50 Listing Image for 149 Luluka Pl 24 of 50 Listing Image for 149 Luluka Pl 25 of 50 Listing Image for 149 Luluka Pl 26 of 50 Listing Image for 149 Luluka Pl 27 of 50 Listing Image for 149 Luluka Pl 28 of 50 Listing Image for 149 Luluka Pl 29 of 50 Listing Image for 149 Luluka Pl 30 of 50 Listing Image for 149 Luluka Pl 31 of 50 Listing Image for 149 Luluka Pl 32 of 50 Listing Image for 149 Luluka Pl 33 of 50 Listing Image for 149 Luluka Pl 34 of 50 Listing Image for 149 Luluka Pl 35 of 50 Listing Image for 149 Luluka Pl 36 of 50 Listing Image for 149 Luluka Pl 37 of 50 Listing Image for 149 Luluka Pl 38 of 50 Listing Image for 149 Luluka Pl 39 of 50 Listing Image for 149 Luluka Pl 40 of 50 Listing Image for 149 Luluka Pl 41 of 50 Listing Image for 149 Luluka Pl 42 of 50 Listing Image for 149 Luluka Pl 43 of 50 Listing Image for 149 Luluka Pl 44 of 50 Listing Image for 149 Luluka Pl 45 of 50 Listing Image for 149 Luluka Pl 46 of 50 Listing Image for 149 Luluka Pl 47 of 50 Listing Image for 149 Luluka Pl 48 of 50 Listing Image for 149 Luluka Pl 49 of 50 Listing Image for 149 Luluka Pl 50 of 50

$1,400,000

Kihei

149 Luluka Pl, Kihei

3 Beds 2 Baths 960 SqFt Residential MLS® # 409035 Date Sold: August 25, 2026
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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