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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Closed: 01/20/2026
Listing Image for 273 Kawailani Cir 1 of 40 Listing Image for 273 Kawailani Cir 2 of 40 Listing Image for 273 Kawailani Cir 3 of 40 Listing Image for 273 Kawailani Cir 4 of 40 Listing Image for 273 Kawailani Cir 5 of 40 Listing Image for 273 Kawailani Cir 6 of 40 Listing Image for 273 Kawailani Cir 7 of 40 Listing Image for 273 Kawailani Cir 8 of 40 Listing Image for 273 Kawailani Cir 9 of 40 Listing Image for 273 Kawailani Cir 10 of 40 Listing Image for 273 Kawailani Cir 11 of 40 Listing Image for 273 Kawailani Cir 12 of 40 Listing Image for 273 Kawailani Cir 13 of 40 Listing Image for 273 Kawailani Cir 14 of 40 Listing Image for 273 Kawailani Cir 15 of 40 Listing Image for 273 Kawailani Cir 16 of 40 Listing Image for 273 Kawailani Cir 17 of 40 Listing Image for 273 Kawailani Cir 18 of 40 Listing Image for 273 Kawailani Cir 19 of 40 Listing Image for 273 Kawailani Cir 20 of 40 Listing Image for 273 Kawailani Cir 21 of 40 Listing Image for 273 Kawailani Cir 22 of 40 Listing Image for 273 Kawailani Cir 23 of 40 Listing Image for 273 Kawailani Cir 24 of 40 Listing Image for 273 Kawailani Cir 25 of 40 Listing Image for 273 Kawailani Cir 26 of 40 Listing Image for 273 Kawailani Cir 27 of 40 Listing Image for 273 Kawailani Cir 28 of 40 Listing Image for 273 Kawailani Cir 29 of 40 Listing Image for 273 Kawailani Cir 30 of 40 Listing Image for 273 Kawailani Cir 31 of 40 Listing Image for 273 Kawailani Cir 32 of 40 Listing Image for 273 Kawailani Cir 33 of 40 Listing Image for 273 Kawailani Cir 34 of 40 Listing Image for 273 Kawailani Cir 35 of 40 Listing Image for 273 Kawailani Cir 36 of 40 Listing Image for 273 Kawailani Cir 37 of 40 Listing Image for 273 Kawailani Cir 38 of 40 Listing Image for 273 Kawailani Cir 39 of 40 Listing Image for 273 Kawailani Cir 40 of 40

$1,010,000

↓ $90,000

Piilani II

273 Kawailani Cir, Kihei

3 Beds 2.5 Baths 1,616 SqFt Residential MLS® # 407589 Date Sold: January 20, 2026
Sold
Closed: 12/26/2025
Listing Image for 2481 Kaanapali Pkwy 1262y 1 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 2 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 3 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 4 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 5 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 6 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 7 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 8 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 9 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 10 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 11 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 12 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 13 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 14 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 15 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 16 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 17 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 18 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 19 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 20 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 21 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 22 of 23 Listing Image for 2481 Kaanapali Pkwy 1262y 23 of 23

$34,000

Whaler 1262Y

2481 Kaanapali Pkwy 1262y, Kaanapali

0 Beds 1 Bath 542 SqFt Residential Income MLS® # 407828 Date Sold: December 26, 2025
Sold
Closed: 05/20/2026
Listing Image for 3036 Kalua Koi Rd 1 of 50 Listing Image for 3036 Kalua Koi Rd 2 of 50 Listing Image for 3036 Kalua Koi Rd 3 of 50 Listing Image for 3036 Kalua Koi Rd 4 of 50 Listing Image for 3036 Kalua Koi Rd 5 of 50 Listing Image for 3036 Kalua Koi Rd 6 of 50 Listing Image for 3036 Kalua Koi Rd 7 of 50 Listing Image for 3036 Kalua Koi Rd 8 of 50 Listing Image for 3036 Kalua Koi Rd 9 of 50 Listing Image for 3036 Kalua Koi Rd 10 of 50 Listing Image for 3036 Kalua Koi Rd 11 of 50 Listing Image for 3036 Kalua Koi Rd 12 of 50 Listing Image for 3036 Kalua Koi Rd 13 of 50 Listing Image for 3036 Kalua Koi Rd 14 of 50 Listing Image for 3036 Kalua Koi Rd 15 of 50 Listing Image for 3036 Kalua Koi Rd 16 of 50 Listing Image for 3036 Kalua Koi Rd 17 of 50 Listing Image for 3036 Kalua Koi Rd 18 of 50 Listing Image for 3036 Kalua Koi Rd 19 of 50 Listing Image for 3036 Kalua Koi Rd 20 of 50 Listing Image for 3036 Kalua Koi Rd 21 of 50 Listing Image for 3036 Kalua Koi Rd 22 of 50 Listing Image for 3036 Kalua Koi Rd 23 of 50 Listing Image for 3036 Kalua Koi Rd 24 of 50 Listing Image for 3036 Kalua Koi Rd 25 of 50 Listing Image for 3036 Kalua Koi Rd 26 of 50 Listing Image for 3036 Kalua Koi Rd 27 of 50 Listing Image for 3036 Kalua Koi Rd 28 of 50 Listing Image for 3036 Kalua Koi Rd 29 of 50 Listing Image for 3036 Kalua Koi Rd 30 of 50 Listing Image for 3036 Kalua Koi Rd 31 of 50 Listing Image for 3036 Kalua Koi Rd 32 of 50 Listing Image for 3036 Kalua Koi Rd 33 of 50 Listing Image for 3036 Kalua Koi Rd 34 of 50 Listing Image for 3036 Kalua Koi Rd 35 of 50 Listing Image for 3036 Kalua Koi Rd 36 of 50 Listing Image for 3036 Kalua Koi Rd 37 of 50 Listing Image for 3036 Kalua Koi Rd 38 of 50 Listing Image for 3036 Kalua Koi Rd 39 of 50 Listing Image for 3036 Kalua Koi Rd 40 of 50 Listing Image for 3036 Kalua Koi Rd 41 of 50 Listing Image for 3036 Kalua Koi Rd 42 of 50 Listing Image for 3036 Kalua Koi Rd 43 of 50 Listing Image for 3036 Kalua Koi Rd 44 of 50 Listing Image for 3036 Kalua Koi Rd 45 of 50 Listing Image for 3036 Kalua Koi Rd 46 of 50 Listing Image for 3036 Kalua Koi Rd 47 of 50 Listing Image for 3036 Kalua Koi Rd 48 of 50 Listing Image for 3036 Kalua Koi Rd 49 of 50 Listing Image for 3036 Kalua Koi Rd 50 of 50

$3,760,000

↓ $440,000

Papohaku Ranchlands

3036 Kalua Koi Rd, Molokai

2 Beds 2.5 Baths 3,794 SqFt Residential MLS® # 407620 Date Sold: May 20, 2026
Sold
Closed: 02/06/2026
Listing Image for 633 Meakanu Ln 204 1 of 36 Listing Image for 633 Meakanu Ln 204 2 of 36 Listing Image for 633 Meakanu Ln 204 3 of 36 Listing Image for 633 Meakanu Ln 204 4 of 36 Listing Image for 633 Meakanu Ln 204 5 of 36 Listing Image for 633 Meakanu Ln 204 6 of 36 Listing Image for 633 Meakanu Ln 204 7 of 36 Listing Image for 633 Meakanu Ln 204 8 of 36 Listing Image for 633 Meakanu Ln 204 9 of 36 Listing Image for 633 Meakanu Ln 204 10 of 36 Listing Image for 633 Meakanu Ln 204 11 of 36 Listing Image for 633 Meakanu Ln 204 12 of 36 Listing Image for 633 Meakanu Ln 204 13 of 36 Listing Image for 633 Meakanu Ln 204 14 of 36 Listing Image for 633 Meakanu Ln 204 15 of 36 Listing Image for 633 Meakanu Ln 204 16 of 36 Listing Image for 633 Meakanu Ln 204 17 of 36 Listing Image for 633 Meakanu Ln 204 18 of 36 Listing Image for 633 Meakanu Ln 204 19 of 36 Listing Image for 633 Meakanu Ln 204 20 of 36 Listing Image for 633 Meakanu Ln 204 21 of 36 Listing Image for 633 Meakanu Ln 204 22 of 36 Listing Image for 633 Meakanu Ln 204 23 of 36 Listing Image for 633 Meakanu Ln 204 24 of 36 Listing Image for 633 Meakanu Ln 204 25 of 36 Listing Image for 633 Meakanu Ln 204 26 of 36 Listing Image for 633 Meakanu Ln 204 27 of 36 Listing Image for 633 Meakanu Ln 204 28 of 36 Listing Image for 633 Meakanu Ln 204 29 of 36 Listing Image for 633 Meakanu Ln 204 30 of 36 Listing Image for 633 Meakanu Ln 204 31 of 36 Listing Image for 633 Meakanu Ln 204 32 of 36 Listing Image for 633 Meakanu Ln 204 33 of 36 Listing Image for 633 Meakanu Ln 204 34 of 36 Listing Image for 633 Meakanu Ln 204 35 of 36 Listing Image for 633 Meakanu Ln 204 36 of 36

$630,000

Kehalani Gardens 204

633 Meakanu Ln 204, Wailuku

2 Beds 2.5 Baths 935 SqFt Residential MLS® # 407767 Date Sold: February 6, 2026
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Sold
Closed: 03/20/2026
Listing Image for 54 Hua Nui Way 1 of 42 Listing Image for 54 Hua Nui Way 2 of 42 Listing Image for 54 Hua Nui Way 3 of 42 Listing Image for 54 Hua Nui Way 4 of 42 Listing Image for 54 Hua Nui Way 5 of 42 Listing Image for 54 Hua Nui Way 6 of 42 Listing Image for 54 Hua Nui Way 7 of 42 Listing Image for 54 Hua Nui Way 8 of 42 Listing Image for 54 Hua Nui Way 9 of 42 Listing Image for 54 Hua Nui Way 10 of 42 Listing Image for 54 Hua Nui Way 11 of 42 Listing Image for 54 Hua Nui Way 12 of 42 Listing Image for 54 Hua Nui Way 13 of 42 Listing Image for 54 Hua Nui Way 14 of 42 Listing Image for 54 Hua Nui Way 15 of 42 Listing Image for 54 Hua Nui Way 16 of 42 Listing Image for 54 Hua Nui Way 17 of 42 Listing Image for 54 Hua Nui Way 18 of 42 Listing Image for 54 Hua Nui Way 19 of 42 Listing Image for 54 Hua Nui Way 20 of 42 Listing Image for 54 Hua Nui Way 21 of 42 Listing Image for 54 Hua Nui Way 22 of 42 Listing Image for 54 Hua Nui Way 23 of 42 Listing Image for 54 Hua Nui Way 24 of 42 Listing Image for 54 Hua Nui Way 25 of 42 Listing Image for 54 Hua Nui Way 26 of 42 Listing Image for 54 Hua Nui Way 27 of 42 Listing Image for 54 Hua Nui Way 28 of 42 Listing Image for 54 Hua Nui Way 29 of 42 Listing Image for 54 Hua Nui Way 30 of 42 Listing Image for 54 Hua Nui Way 31 of 42 Listing Image for 54 Hua Nui Way 32 of 42 Listing Image for 54 Hua Nui Way 33 of 42 Listing Image for 54 Hua Nui Way 34 of 42 Listing Image for 54 Hua Nui Way 35 of 42 Listing Image for 54 Hua Nui Way 36 of 42 Listing Image for 54 Hua Nui Way 37 of 42 Listing Image for 54 Hua Nui Way 38 of 42 Listing Image for 54 Hua Nui Way 39 of 42 Listing Image for 54 Hua Nui Way 40 of 42 Listing Image for 54 Hua Nui Way 41 of 42 Listing Image for 54 Hua Nui Way 42 of 42

$1,500,000

Kahana Wai

54 Hua Nui Way, Napili/Kahana/Honokowai

3 Beds 2.5 Baths 1,926 SqFt Residential MLS® # 407647 Date Sold: March 20, 2026
Sold
Closed: 11/14/2025
Listing Image for 517 Imi Pl 1 of 3 Listing Image for 517 Imi Pl 2 of 3 Listing Image for 517 Imi Pl 3 of 3

$1,600,000

Wailuku

517 Imi Pl, Wailuku

7 Beds 1 Bath 2,277 SqFt Residential Income MLS® # 407758 Date Sold: November 14, 2025
Sold
Closed: 10/12/2026
Listing Image for 2619 S Kihei Rd A409 1 of 48 Listing Image for 2619 S Kihei Rd A409 2 of 48 Listing Image for 2619 S Kihei Rd A409 3 of 48 Listing Image for 2619 S Kihei Rd A409 4 of 48 Listing Image for 2619 S Kihei Rd A409 5 of 48 Listing Image for 2619 S Kihei Rd A409 6 of 48 Listing Image for 2619 S Kihei Rd A409 7 of 48 Listing Image for 2619 S Kihei Rd A409 8 of 48 Listing Image for 2619 S Kihei Rd A409 9 of 48 Listing Image for 2619 S Kihei Rd A409 10 of 48 Listing Image for 2619 S Kihei Rd A409 11 of 48 Listing Image for 2619 S Kihei Rd A409 12 of 48 Listing Image for 2619 S Kihei Rd A409 13 of 48 Listing Image for 2619 S Kihei Rd A409 14 of 48 Listing Image for 2619 S Kihei Rd A409 15 of 48 Listing Image for 2619 S Kihei Rd A409 16 of 48 Listing Image for 2619 S Kihei Rd A409 17 of 48 Listing Image for 2619 S Kihei Rd A409 18 of 48 Listing Image for 2619 S Kihei Rd A409 19 of 48 Listing Image for 2619 S Kihei Rd A409 20 of 48 Listing Image for 2619 S Kihei Rd A409 21 of 48 Listing Image for 2619 S Kihei Rd A409 22 of 48 Listing Image for 2619 S Kihei Rd A409 23 of 48 Listing Image for 2619 S Kihei Rd A409 24 of 48 Listing Image for 2619 S Kihei Rd A409 25 of 48 Listing Image for 2619 S Kihei Rd A409 26 of 48 Listing Image for 2619 S Kihei Rd A409 27 of 48 Listing Image for 2619 S Kihei Rd A409 28 of 48 Listing Image for 2619 S Kihei Rd A409 29 of 48 Listing Image for 2619 S Kihei Rd A409 30 of 48 Listing Image for 2619 S Kihei Rd A409 31 of 48 Listing Image for 2619 S Kihei Rd A409 32 of 48 Listing Image for 2619 S Kihei Rd A409 33 of 48 Listing Image for 2619 S Kihei Rd A409 34 of 48 Listing Image for 2619 S Kihei Rd A409 35 of 48 Listing Image for 2619 S Kihei Rd A409 36 of 48 Listing Image for 2619 S Kihei Rd A409 37 of 48 Listing Image for 2619 S Kihei Rd A409 38 of 48 Listing Image for 2619 S Kihei Rd A409 39 of 48 Listing Image for 2619 S Kihei Rd A409 40 of 48 Listing Image for 2619 S Kihei Rd A409 41 of 48 Listing Image for 2619 S Kihei Rd A409 42 of 48 Listing Image for 2619 S Kihei Rd A409 43 of 48 Listing Image for 2619 S Kihei Rd A409 44 of 48 Listing Image for 2619 S Kihei Rd A409 45 of 48 Listing Image for 2619 S Kihei Rd A409 46 of 48 Listing Image for 2619 S Kihei Rd A409 47 of 48 Listing Image for 2619 S Kihei Rd A409 48 of 48

$555,000

↓ $144,000

Haleakala Shores A409

2619 S Kihei Rd A409, Kihei

2 Beds 2 Baths 1,048 SqFt Residential MLS® # 407919 Date Sold: October 12, 2026
Sold
Closed: 07/28/2026
Listing Image for 55 Waiaka Ln 34-203 1 of 17 Listing Image for 55 Waiaka Ln 34-203 2 of 17 Listing Image for 55 Waiaka Ln 34-203 3 of 17 Listing Image for 55 Waiaka Ln 34-203 4 of 17 Listing Image for 55 Waiaka Ln 34-203 5 of 17 Listing Image for 55 Waiaka Ln 34-203 6 of 17 Listing Image for 55 Waiaka Ln 34-203 7 of 17 Listing Image for 55 Waiaka Ln 34-203 8 of 17 Listing Image for 55 Waiaka Ln 34-203 9 of 17 Listing Image for 55 Waiaka Ln 34-203 10 of 17 Listing Image for 55 Waiaka Ln 34-203 11 of 17 Listing Image for 55 Waiaka Ln 34-203 12 of 17 Listing Image for 55 Waiaka Ln 34-203 13 of 17 Listing Image for 55 Waiaka Ln 34-203 14 of 17 Listing Image for 55 Waiaka Ln 34-203 15 of 17 Listing Image for 55 Waiaka Ln 34-203 16 of 17 Listing Image for 55 Waiaka Ln 34-203 17 of 17

$363,000

↓ $27,000

Iao Parkside IV-A 34-203

55 Waiaka Ln 34-203, Wailuku

2 Beds 2 Baths 837 SqFt Residential MLS® # 407787 Date Sold: July 28, 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. 

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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