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: 08/14/2026
Listing Image for 35 Walaka St L209 1 of 50 Listing Image for 35 Walaka St L209 2 of 50 Listing Image for 35 Walaka St L209 3 of 50 Listing Image for 35 Walaka St L209 4 of 50 Listing Image for 35 Walaka St L209 5 of 50 Listing Image for 35 Walaka St L209 6 of 50 Listing Image for 35 Walaka St L209 7 of 50 Listing Image for 35 Walaka St L209 8 of 50 Listing Image for 35 Walaka St L209 9 of 50 Listing Image for 35 Walaka St L209 10 of 50 Listing Image for 35 Walaka St L209 11 of 50 Listing Image for 35 Walaka St L209 12 of 50 Listing Image for 35 Walaka St L209 13 of 50 Listing Image for 35 Walaka St L209 14 of 50 Listing Image for 35 Walaka St L209 15 of 50 Listing Image for 35 Walaka St L209 16 of 50 Listing Image for 35 Walaka St L209 17 of 50 Listing Image for 35 Walaka St L209 18 of 50 Listing Image for 35 Walaka St L209 19 of 50 Listing Image for 35 Walaka St L209 20 of 50 Listing Image for 35 Walaka St L209 21 of 50 Listing Image for 35 Walaka St L209 22 of 50 Listing Image for 35 Walaka St L209 23 of 50 Listing Image for 35 Walaka St L209 24 of 50 Listing Image for 35 Walaka St L209 25 of 50 Listing Image for 35 Walaka St L209 26 of 50 Listing Image for 35 Walaka St L209 27 of 50 Listing Image for 35 Walaka St L209 28 of 50 Listing Image for 35 Walaka St L209 29 of 50 Listing Image for 35 Walaka St L209 30 of 50 Listing Image for 35 Walaka St L209 31 of 50 Listing Image for 35 Walaka St L209 32 of 50 Listing Image for 35 Walaka St L209 33 of 50 Listing Image for 35 Walaka St L209 34 of 50 Listing Image for 35 Walaka St L209 35 of 50 Listing Image for 35 Walaka St L209 36 of 50 Listing Image for 35 Walaka St L209 37 of 50 Listing Image for 35 Walaka St L209 38 of 50 Listing Image for 35 Walaka St L209 39 of 50 Listing Image for 35 Walaka St L209 40 of 50 Listing Image for 35 Walaka St L209 41 of 50 Listing Image for 35 Walaka St L209 42 of 50 Listing Image for 35 Walaka St L209 43 of 50 Listing Image for 35 Walaka St L209 44 of 50 Listing Image for 35 Walaka St L209 45 of 50 Listing Image for 35 Walaka St L209 46 of 50 Listing Image for 35 Walaka St L209 47 of 50 Listing Image for 35 Walaka St L209 48 of 50 Listing Image for 35 Walaka St L209 49 of 50 Listing Image for 35 Walaka St L209 50 of 50

$275,000

↓ $34,000

Kalama Terrace L209

35 Walaka St L209, Kihei

1 Bed 1 Bath 535 SqFt Residential MLS® # 409478 Date Sold: August 14, 2026
New Sold
Closed: 06/08/2026
Listing Image for 34 Paihua St 1 of 23 Listing Image for 34 Paihua St 2 of 23 Listing Image for 34 Paihua St 3 of 23 Listing Image for 34 Paihua St 4 of 23 Listing Image for 34 Paihua St 5 of 23 Listing Image for 34 Paihua St 6 of 23 Listing Image for 34 Paihua St 7 of 23 Listing Image for 34 Paihua St 8 of 23 Listing Image for 34 Paihua St 9 of 23 Listing Image for 34 Paihua St 10 of 23 Listing Image for 34 Paihua St 11 of 23 Listing Image for 34 Paihua St 12 of 23 Listing Image for 34 Paihua St 13 of 23 Listing Image for 34 Paihua St 14 of 23 Listing Image for 34 Paihua St 15 of 23 Listing Image for 34 Paihua St 16 of 23 Listing Image for 34 Paihua St 17 of 23 Listing Image for 34 Paihua St 18 of 23 Listing Image for 34 Paihua St 19 of 23 Listing Image for 34 Paihua St 20 of 23 Listing Image for 34 Paihua St 21 of 23 Listing Image for 34 Paihua St 22 of 23 Listing Image for 34 Paihua St 23 of 23

$700,001

Haliimaile

34 Paihua St, Makawao/Olinda/Haliimaile

3 Beds 1 Bath 1,132 SqFt Residential MLS® # 409542 Date Sold: June 8, 2026
New Sold
Closed: 07/30/2026
Listing Image for 35 Hui F Rd B 1 of 38 Listing Image for 35 Hui F Rd B 2 of 38 Listing Image for 35 Hui F Rd B 3 of 38 Listing Image for 35 Hui F Rd B 4 of 38 Listing Image for 35 Hui F Rd B 5 of 38 Listing Image for 35 Hui F Rd B 6 of 38 Listing Image for 35 Hui F Rd B 7 of 38 Listing Image for 35 Hui F Rd B 8 of 38 Listing Image for 35 Hui F Rd B 9 of 38 Listing Image for 35 Hui F Rd B 10 of 38 Listing Image for 35 Hui F Rd B 11 of 38 Listing Image for 35 Hui F Rd B 12 of 38 Listing Image for 35 Hui F Rd B 13 of 38 Listing Image for 35 Hui F Rd B 14 of 38 Listing Image for 35 Hui F Rd B 15 of 38 Listing Image for 35 Hui F Rd B 16 of 38 Listing Image for 35 Hui F Rd B 17 of 38 Listing Image for 35 Hui F Rd B 18 of 38 Listing Image for 35 Hui F Rd B 19 of 38 Listing Image for 35 Hui F Rd B 20 of 38 Listing Image for 35 Hui F Rd B 21 of 38 Listing Image for 35 Hui F Rd B 22 of 38 Listing Image for 35 Hui F Rd B 23 of 38 Listing Image for 35 Hui F Rd B 24 of 38 Listing Image for 35 Hui F Rd B 25 of 38 Listing Image for 35 Hui F Rd B 26 of 38 Listing Image for 35 Hui F Rd B 27 of 38 Listing Image for 35 Hui F Rd B 28 of 38 Listing Image for 35 Hui F Rd B 29 of 38 Listing Image for 35 Hui F Rd B 30 of 38 Listing Image for 35 Hui F Rd B 31 of 38 Listing Image for 35 Hui F Rd B 32 of 38 Listing Image for 35 Hui F Rd B 33 of 38 Listing Image for 35 Hui F Rd B 34 of 38 Listing Image for 35 Hui F Rd B 35 of 38 Listing Image for 35 Hui F Rd B 36 of 38 Listing Image for 35 Hui F Rd B 37 of 38 Listing Image for 35 Hui F Rd B 38 of 38

$1,132,000

Napili

35 Hui F Rd B, Napili/Kahana/Honokowai

3 Beds 1.5 Baths 1,416 SqFt Residential MLS® # 409617 Date Sold: July 30, 2026
New Sold
Closed: 08/24/2026
Listing Image for 4401 Lower Honoapiilani Rd A604 1 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 2 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 3 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 4 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 5 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 6 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 7 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 8 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 9 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 10 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 11 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 12 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 13 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 14 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 15 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 16 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 17 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 18 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 19 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 20 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 21 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 22 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 23 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 24 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 25 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 26 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 27 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 28 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 29 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 30 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 31 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 32 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 33 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 34 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 35 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 36 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 37 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 38 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 39 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 40 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 41 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 42 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 43 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 44 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 45 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 46 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 47 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 48 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 49 of 50 Listing Image for 4401 Lower Honoapiilani Rd A604 50 of 50

$725,000

↓ $125,000

Hololani A604

4401 Lower Honoapiilani Rd A604, Napili/Kahana/Honokowai

2 Beds 2 Baths 1,066 SqFt Residential MLS® # 409456 Date Sold: August 24, 2026
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New Sold
Closed: 07/24/2026
Listing Image for 2881 S Kihei Rd 8 1 of 48 Listing Image for 2881 S Kihei Rd 8 2 of 48 Listing Image for 2881 S Kihei Rd 8 3 of 48 Listing Image for 2881 S Kihei Rd 8 4 of 48 Listing Image for 2881 S Kihei Rd 8 5 of 48 Listing Image for 2881 S Kihei Rd 8 6 of 48 Listing Image for 2881 S Kihei Rd 8 7 of 48 Listing Image for 2881 S Kihei Rd 8 8 of 48 Listing Image for 2881 S Kihei Rd 8 9 of 48 Listing Image for 2881 S Kihei Rd 8 10 of 48 Listing Image for 2881 S Kihei Rd 8 11 of 48 Listing Image for 2881 S Kihei Rd 8 12 of 48 Listing Image for 2881 S Kihei Rd 8 13 of 48 Listing Image for 2881 S Kihei Rd 8 14 of 48 Listing Image for 2881 S Kihei Rd 8 15 of 48 Listing Image for 2881 S Kihei Rd 8 16 of 48 Listing Image for 2881 S Kihei Rd 8 17 of 48 Listing Image for 2881 S Kihei Rd 8 18 of 48 Listing Image for 2881 S Kihei Rd 8 19 of 48 Listing Image for 2881 S Kihei Rd 8 20 of 48 Listing Image for 2881 S Kihei Rd 8 21 of 48 Listing Image for 2881 S Kihei Rd 8 22 of 48 Listing Image for 2881 S Kihei Rd 8 23 of 48 Listing Image for 2881 S Kihei Rd 8 24 of 48 Listing Image for 2881 S Kihei Rd 8 25 of 48 Listing Image for 2881 S Kihei Rd 8 26 of 48 Listing Image for 2881 S Kihei Rd 8 27 of 48 Listing Image for 2881 S Kihei Rd 8 28 of 48 Listing Image for 2881 S Kihei Rd 8 29 of 48 Listing Image for 2881 S Kihei Rd 8 30 of 48 Listing Image for 2881 S Kihei Rd 8 31 of 48 Listing Image for 2881 S Kihei Rd 8 32 of 48 Listing Image for 2881 S Kihei Rd 8 33 of 48 Listing Image for 2881 S Kihei Rd 8 34 of 48 Listing Image for 2881 S Kihei Rd 8 35 of 48 Listing Image for 2881 S Kihei Rd 8 36 of 48 Listing Image for 2881 S Kihei Rd 8 37 of 48 Listing Image for 2881 S Kihei Rd 8 38 of 48 Listing Image for 2881 S Kihei Rd 8 39 of 48 Listing Image for 2881 S Kihei Rd 8 40 of 48 Listing Image for 2881 S Kihei Rd 8 41 of 48 Listing Image for 2881 S Kihei Rd 8 42 of 48 Listing Image for 2881 S Kihei Rd 8 43 of 48 Listing Image for 2881 S Kihei Rd 8 44 of 48 Listing Image for 2881 S Kihei Rd 8 45 of 48 Listing Image for 2881 S Kihei Rd 8 46 of 48 Listing Image for 2881 S Kihei Rd 8 47 of 48 Listing Image for 2881 S Kihei Rd 8 48 of 48

$895,000

Maui Hill 8

2881 S Kihei Rd 8, Kihei

3 Beds 3 Baths 1,395 SqFt Residential MLS® # 409329 Date Sold: July 24, 2026
New Sold
Closed: 07/28/2026
Listing Image for 10 Wailea Ekolu Pl 308 1 of 49 Listing Image for 10 Wailea Ekolu Pl 308 2 of 49 Listing Image for 10 Wailea Ekolu Pl 308 3 of 49 Listing Image for 10 Wailea Ekolu Pl 308 4 of 49 Listing Image for 10 Wailea Ekolu Pl 308 5 of 49 Listing Image for 10 Wailea Ekolu Pl 308 6 of 49 Listing Image for 10 Wailea Ekolu Pl 308 7 of 49 Listing Image for 10 Wailea Ekolu Pl 308 8 of 49 Listing Image for 10 Wailea Ekolu Pl 308 9 of 49 Listing Image for 10 Wailea Ekolu Pl 308 10 of 49 Listing Image for 10 Wailea Ekolu Pl 308 11 of 49 Listing Image for 10 Wailea Ekolu Pl 308 12 of 49 Listing Image for 10 Wailea Ekolu Pl 308 13 of 49 Listing Image for 10 Wailea Ekolu Pl 308 14 of 49 Listing Image for 10 Wailea Ekolu Pl 308 15 of 49 Listing Image for 10 Wailea Ekolu Pl 308 16 of 49 Listing Image for 10 Wailea Ekolu Pl 308 17 of 49 Listing Image for 10 Wailea Ekolu Pl 308 18 of 49 Listing Image for 10 Wailea Ekolu Pl 308 19 of 49 Listing Image for 10 Wailea Ekolu Pl 308 20 of 49 Listing Image for 10 Wailea Ekolu Pl 308 21 of 49 Listing Image for 10 Wailea Ekolu Pl 308 22 of 49 Listing Image for 10 Wailea Ekolu Pl 308 23 of 49 Listing Image for 10 Wailea Ekolu Pl 308 24 of 49 Listing Image for 10 Wailea Ekolu Pl 308 25 of 49 Listing Image for 10 Wailea Ekolu Pl 308 26 of 49 Listing Image for 10 Wailea Ekolu Pl 308 27 of 49 Listing Image for 10 Wailea Ekolu Pl 308 28 of 49 Listing Image for 10 Wailea Ekolu Pl 308 29 of 49 Listing Image for 10 Wailea Ekolu Pl 308 30 of 49 Listing Image for 10 Wailea Ekolu Pl 308 31 of 49 Listing Image for 10 Wailea Ekolu Pl 308 32 of 49 Listing Image for 10 Wailea Ekolu Pl 308 33 of 49 Listing Image for 10 Wailea Ekolu Pl 308 34 of 49 Listing Image for 10 Wailea Ekolu Pl 308 35 of 49 Listing Image for 10 Wailea Ekolu Pl 308 36 of 49 Listing Image for 10 Wailea Ekolu Pl 308 37 of 49 Listing Image for 10 Wailea Ekolu Pl 308 38 of 49 Listing Image for 10 Wailea Ekolu Pl 308 39 of 49 Listing Image for 10 Wailea Ekolu Pl 308 40 of 49 Listing Image for 10 Wailea Ekolu Pl 308 41 of 49 Listing Image for 10 Wailea Ekolu Pl 308 42 of 49 Listing Image for 10 Wailea Ekolu Pl 308 43 of 49 Listing Image for 10 Wailea Ekolu Pl 308 44 of 49 Listing Image for 10 Wailea Ekolu Pl 308 45 of 49 Listing Image for 10 Wailea Ekolu Pl 308 46 of 49 Listing Image for 10 Wailea Ekolu Pl 308 47 of 49 Listing Image for 10 Wailea Ekolu Pl 308 48 of 49 Listing Image for 10 Wailea Ekolu Pl 308 49 of 49

$1,375,000

Wailea Ekolu 308

10 Wailea Ekolu Pl 308, Wailea/Makena

2 Beds 2 Baths 1,071 SqFt Residential MLS® # 409418 Date Sold: July 28, 2026
New Sold
Closed: 07/02/2026
Listing Image for 22 Kakawahie St 83 1 of 42 Listing Image for 22 Kakawahie St 83 2 of 42 Listing Image for 22 Kakawahie St 83 3 of 42 Listing Image for 22 Kakawahie St 83 4 of 42 Listing Image for 22 Kakawahie St 83 5 of 42 Listing Image for 22 Kakawahie St 83 6 of 42 Listing Image for 22 Kakawahie St 83 7 of 42 Listing Image for 22 Kakawahie St 83 8 of 42 Listing Image for 22 Kakawahie St 83 9 of 42 Listing Image for 22 Kakawahie St 83 10 of 42 Listing Image for 22 Kakawahie St 83 11 of 42 Listing Image for 22 Kakawahie St 83 12 of 42 Listing Image for 22 Kakawahie St 83 13 of 42 Listing Image for 22 Kakawahie St 83 14 of 42 Listing Image for 22 Kakawahie St 83 15 of 42 Listing Image for 22 Kakawahie St 83 16 of 42 Listing Image for 22 Kakawahie St 83 17 of 42 Listing Image for 22 Kakawahie St 83 18 of 42 Listing Image for 22 Kakawahie St 83 19 of 42 Listing Image for 22 Kakawahie St 83 20 of 42 Listing Image for 22 Kakawahie St 83 21 of 42 Listing Image for 22 Kakawahie St 83 22 of 42 Listing Image for 22 Kakawahie St 83 23 of 42 Listing Image for 22 Kakawahie St 83 24 of 42 Listing Image for 22 Kakawahie St 83 25 of 42 Listing Image for 22 Kakawahie St 83 26 of 42 Listing Image for 22 Kakawahie St 83 27 of 42 Listing Image for 22 Kakawahie St 83 28 of 42 Listing Image for 22 Kakawahie St 83 29 of 42 Listing Image for 22 Kakawahie St 83 30 of 42 Listing Image for 22 Kakawahie St 83 31 of 42 Listing Image for 22 Kakawahie St 83 32 of 42 Listing Image for 22 Kakawahie St 83 33 of 42 Listing Image for 22 Kakawahie St 83 34 of 42 Listing Image for 22 Kakawahie St 83 35 of 42 Listing Image for 22 Kakawahie St 83 36 of 42 Listing Image for 22 Kakawahie St 83 37 of 42 Listing Image for 22 Kakawahie St 83 38 of 42 Listing Image for 22 Kakawahie St 83 39 of 42 Listing Image for 22 Kakawahie St 83 40 of 42 Listing Image for 22 Kakawahie St 83 41 of 42 Listing Image for 22 Kakawahie St 83 42 of 42

$865,000

Kamani at Kehalani 83

22 Kakawahie St 83, Wailuku

3 Beds 2.5 Baths 1,457 SqFt Residential MLS® # 409469 Date Sold: July 2, 2026
New Sold
Closed: 03/27/2026
Listing Image for 52 Kai Malu Dr 101 (9a) 1 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 2 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 3 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 4 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 5 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 6 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 7 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 8 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 9 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 10 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 11 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 12 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 13 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 14 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 15 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 16 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 17 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 18 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 19 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 20 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 21 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 22 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 23 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 24 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 25 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 26 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 27 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 28 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 29 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 30 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 31 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 32 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 33 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 34 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 35 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 36 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 37 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 38 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 39 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 40 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 41 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 42 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 43 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 44 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 45 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 46 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 47 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 48 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 49 of 50 Listing Image for 52 Kai Malu Dr 101 (9a) 50 of 50

$3,850,000

La'i Loa 101 (9A)

52 Kai Malu Dr 101 (9a), Wailea/Makena

3 Beds 3 Baths 1,742 SqFt Residential MLS® # 409120 Date Sold: March 27, 2026
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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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