Strategies of Buying and Selling Simultaneously

Buying and Selling a Home at the Same Time

You may have found yourself in a position where you would like to buy one property while simultaneously selling another property. While doing this does present some unique challenges, it's completely possible to pull this off with the proper strategy and some degree of flexibility

The reasons and strategies for wanting to buy and sell simultaneously will differ from a primary homeowner looking to relocate to an investor seeking to execute a 1031 exchange to avoid capital gains taxes. In either instance, it's important to have a sound strategy and understand what the undertaking will involve. 

Selling A Primary Residence While Buying Another

There are several different ways to do this and how you do it will depend on your financial philosophies. There isn't necessarily a right and wrong way to approach this, some consider selling their home first the priority and then are willing to rent for a period of 6 months while they find the perfect replacement. This is usually the lowest stress avenue.

Some will be intent on executing the sale and purchase in such a way that both properties close in close succession to remove the extra step of renting. Money is a huge consideration for this move, particularly when financing is involved. In many instances, sellers will need the equity from the sale of their home to fund the down payment on the purchase of the second. 

If Financing is Necessary, Get Prequalified for a New Mortgage First

Before you get serious about selling your home, you should thoroughly research the possibility of buying a new primary residence. The Maui housing market can change rapidly at times, and the lending environment is changing as well. When you get prequalified with a local Maui lender, you can better determine your price range for a new home.

You can get accurate information about the interest rates available for your credit score and other qualifications. In addition, you can confirm that you can afford the loan payment for the size and quality of the home you are interested in.

Discuss Your Plans with a Real Estate Agent

After learning about your prequalification status, consulting with real estate agents in Maui is the next step. An experienced Maui real estate agent can help you determine how long your home may reasonably remain on the market.

In addition, you can get details on a realistic sales price. By analyzing the sales price in combination with closing costs and the current mortgage payoff balance, you can determine the sales proceeds that you have available for a down payment on your new home purchase. 

Newest Maui Properties For Sale

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$1,350,000

Wailea Ekahi 17A

3300 Wailea Alanui Dr 17a, Wailea/Makena

1 Bed 2 Baths 885 SqFt Residential MLS® # 409758

Days on Market: 109

Hawaii Life (W) Cell: 808-357-5000

Short Term Rental
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$3,249,000

Montage Residences Kapalua Bay 2204

1 Bay Dr 2204, Kapalua

3 Beds 3.5 Baths 2,789 SqFt Residential MLS® # 409757

Days on Market: 110

Keller Williams Realty Maui-L Cell: 808-870-7736

In Escrow
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$1,799,999

Masters 603

50 Puu Anoano St 603, Kaanapali

3 Beds 2 Baths 1,544 SqFt Residential MLS® # 409756

Days on Market: 109

Coldwell Banker Island Prop-KP Cell: 808-283-3067

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

$1,235,000

↓ $100,000

Waiakoa Estates

20 Kuulani Pl, Kula/Ulupalakua/Kanaio

2 Beds 1 Bath 1,008 SqFt Residential MLS® # 409753

Days on Market: 110

Delmore Realty kim@delmore.net

Buying Real Estate on Maui

Buying Real Estate on Maui

Read Evan's complete guide to buying a home or condo on Maui.

Read the Guide
Listing Image for 28 Kai Makani Loop 28-103 1 of 50 Listing Image for 28 Kai Makani Loop 28-103 2 of 50 Listing Image for 28 Kai Makani Loop 28-103 3 of 50 Listing Image for 28 Kai Makani Loop 28-103 4 of 50 Listing Image for 28 Kai Makani Loop 28-103 5 of 50 Listing Image for 28 Kai Makani Loop 28-103 6 of 50 Listing Image for 28 Kai Makani Loop 28-103 7 of 50 Listing Image for 28 Kai Makani Loop 28-103 8 of 50 Listing Image for 28 Kai Makani Loop 28-103 9 of 50 Listing Image for 28 Kai Makani Loop 28-103 10 of 50 Listing Image for 28 Kai Makani Loop 28-103 11 of 50 Listing Image for 28 Kai Makani Loop 28-103 12 of 50 Listing Image for 28 Kai Makani Loop 28-103 13 of 50 Listing Image for 28 Kai Makani Loop 28-103 14 of 50 Listing Image for 28 Kai Makani Loop 28-103 15 of 50 Listing Image for 28 Kai Makani Loop 28-103 16 of 50 Listing Image for 28 Kai Makani Loop 28-103 17 of 50 Listing Image for 28 Kai Makani Loop 28-103 18 of 50 Listing Image for 28 Kai Makani Loop 28-103 19 of 50 Listing Image for 28 Kai Makani Loop 28-103 20 of 50 Listing Image for 28 Kai Makani Loop 28-103 21 of 50 Listing Image for 28 Kai Makani Loop 28-103 22 of 50 Listing Image for 28 Kai Makani Loop 28-103 23 of 50 Listing Image for 28 Kai Makani Loop 28-103 24 of 50 Listing Image for 28 Kai Makani Loop 28-103 25 of 50 Listing Image for 28 Kai Makani Loop 28-103 26 of 50 Listing Image for 28 Kai Makani Loop 28-103 27 of 50 Listing Image for 28 Kai Makani Loop 28-103 28 of 50 Listing Image for 28 Kai Makani Loop 28-103 29 of 50 Listing Image for 28 Kai Makani Loop 28-103 30 of 50 Listing Image for 28 Kai Makani Loop 28-103 31 of 50 Listing Image for 28 Kai Makani Loop 28-103 32 of 50 Listing Image for 28 Kai Makani Loop 28-103 33 of 50 Listing Image for 28 Kai Makani Loop 28-103 34 of 50 Listing Image for 28 Kai Makani Loop 28-103 35 of 50 Listing Image for 28 Kai Makani Loop 28-103 36 of 50 Listing Image for 28 Kai Makani Loop 28-103 37 of 50 Listing Image for 28 Kai Makani Loop 28-103 38 of 50 Listing Image for 28 Kai Makani Loop 28-103 39 of 50 Listing Image for 28 Kai Makani Loop 28-103 40 of 50 Listing Image for 28 Kai Makani Loop 28-103 41 of 50 Listing Image for 28 Kai Makani Loop 28-103 42 of 50 Listing Image for 28 Kai Makani Loop 28-103 43 of 50 Listing Image for 28 Kai Makani Loop 28-103 44 of 50 Listing Image for 28 Kai Makani Loop 28-103 45 of 50 Listing Image for 28 Kai Makani Loop 28-103 46 of 50 Listing Image for 28 Kai Makani Loop 28-103 47 of 50 Listing Image for 28 Kai Makani Loop 28-103 48 of 50 Listing Image for 28 Kai Makani Loop 28-103 49 of 50 Listing Image for 28 Kai Makani Loop 28-103 50 of 50

$949,000

↓ $41,000

Kai Makani 28-103

28 Kai Makani Loop 28-103, Kihei

2 Beds 2 Baths 1,126 SqFt Residential MLS® # 409749

Days on Market: 110

Engel & Volkers Maui

234 Halenani Dr, Wailuku

$1,100,000

Sand Hills

234 Halenani Dr, Wailuku

4 Beds 2.5 Baths 1,644 SqFt Residential MLS® # 409746

Days on Market: 111

Claire's Realty LLC

In Escrow
Listing Image for 94 Mehani Pl 1 of 48 Listing Image for 94 Mehani Pl 2 of 48 Listing Image for 94 Mehani Pl 3 of 48 Listing Image for 94 Mehani Pl 4 of 48 Listing Image for 94 Mehani Pl 5 of 48 Listing Image for 94 Mehani Pl 6 of 48 Listing Image for 94 Mehani Pl 7 of 48 Listing Image for 94 Mehani Pl 8 of 48 Listing Image for 94 Mehani Pl 9 of 48 Listing Image for 94 Mehani Pl 10 of 48 Listing Image for 94 Mehani Pl 11 of 48 Listing Image for 94 Mehani Pl 12 of 48 Listing Image for 94 Mehani Pl 13 of 48 Listing Image for 94 Mehani Pl 14 of 48 Listing Image for 94 Mehani Pl 15 of 48 Listing Image for 94 Mehani Pl 16 of 48 Listing Image for 94 Mehani Pl 17 of 48 Listing Image for 94 Mehani Pl 18 of 48 Listing Image for 94 Mehani Pl 19 of 48 Listing Image for 94 Mehani Pl 20 of 48 Listing Image for 94 Mehani Pl 21 of 48 Listing Image for 94 Mehani Pl 22 of 48 Listing Image for 94 Mehani Pl 23 of 48 Listing Image for 94 Mehani Pl 24 of 48 Listing Image for 94 Mehani Pl 25 of 48 Listing Image for 94 Mehani Pl 26 of 48 Listing Image for 94 Mehani Pl 27 of 48 Listing Image for 94 Mehani Pl 28 of 48 Listing Image for 94 Mehani Pl 29 of 48 Listing Image for 94 Mehani Pl 30 of 48 Listing Image for 94 Mehani Pl 31 of 48 Listing Image for 94 Mehani Pl 32 of 48 Listing Image for 94 Mehani Pl 33 of 48 Listing Image for 94 Mehani Pl 34 of 48 Listing Image for 94 Mehani Pl 35 of 48 Listing Image for 94 Mehani Pl 36 of 48 Listing Image for 94 Mehani Pl 37 of 48 Listing Image for 94 Mehani Pl 38 of 48 Listing Image for 94 Mehani Pl 39 of 48 Listing Image for 94 Mehani Pl 40 of 48 Listing Image for 94 Mehani Pl 41 of 48 Listing Image for 94 Mehani Pl 42 of 48 Listing Image for 94 Mehani Pl 43 of 48 Listing Image for 94 Mehani Pl 44 of 48 Listing Image for 94 Mehani Pl 45 of 48 Listing Image for 94 Mehani Pl 46 of 48 Listing Image for 94 Mehani Pl 47 of 48 Listing Image for 94 Mehani Pl 48 of 48

$1,350,000

↓ $25,000

Waimahaihai

94 Mehani Pl, Kihei

3 Beds 3.5 Baths 1,696 SqFt Residential MLS® # 409735

Days on Market: 111

Keller Williams Realty Maui-Ka Cell: 808-868-6260

View 7 More Listings

Apply for a Home Equity Loan

While you may ideally want to sell your current house before buying a new one, this may not be an absolute requirement for some sellers. You could tap into your home’s equity by applying for an equity line of credit. Before moving forward with this possibility, be aware that the payment on the new home equity line will affect your debt-to-income ratio.

Mortgage lenders review your debt-to-income ratio as part of their qualification process. Because of this, you should discuss this option in detail with your lender to ensure that it will not impair your ability to qualify for a new mortgage.

Recent Sales on Maui

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
Sold
Closed: 08/11/2026
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$968,000

↓ $32,000

Maui Lani

17 Molehulehu Loop, Kahului

3 Beds 2 Baths 1,426 SqFt Residential MLS® # 408476 Date Sold: August 11, 2026
Sold
Closed: 03/30/2026
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$960,000

Maalaea Kai 403

70 Hauoli St 403, Maalaea

2 Beds 2 Baths 824 SqFt Residential MLS® # 408475 Date Sold: March 30, 2026
Sold
Closed: 03/04/2026
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$1,175,000

Ohia at Kehalani

668 Komo Ohia St, Wailuku

3 Beds 2.5 Baths 1,766 SqFt Residential MLS® # 408474 Date Sold: March 4, 2026
Buying Real Estate on Maui

Buying Real Estate on Maui

Read Evan's complete guide to buying a home or condo on Maui.

Read the Guide
Sold
Closed: 04/17/2026
Listing Image for 235 Wailau Pl 1 of 41 Listing Image for 235 Wailau Pl 2 of 41 Listing Image for 235 Wailau Pl 3 of 41 Listing Image for 235 Wailau Pl 4 of 41 Listing Image for 235 Wailau Pl 5 of 41 Listing Image for 235 Wailau Pl 6 of 41 Listing Image for 235 Wailau Pl 7 of 41 Listing Image for 235 Wailau Pl 8 of 41 Listing Image for 235 Wailau Pl 9 of 41 Listing Image for 235 Wailau Pl 10 of 41 Listing Image for 235 Wailau Pl 11 of 41 Listing Image for 235 Wailau Pl 12 of 41 Listing Image for 235 Wailau Pl 13 of 41 Listing Image for 235 Wailau Pl 14 of 41 Listing Image for 235 Wailau Pl 15 of 41 Listing Image for 235 Wailau Pl 16 of 41 Listing Image for 235 Wailau Pl 17 of 41 Listing Image for 235 Wailau Pl 18 of 41 Listing Image for 235 Wailau Pl 19 of 41 Listing Image for 235 Wailau Pl 20 of 41 Listing Image for 235 Wailau Pl 21 of 41 Listing Image for 235 Wailau Pl 22 of 41 Listing Image for 235 Wailau Pl 23 of 41 Listing Image for 235 Wailau Pl 24 of 41 Listing Image for 235 Wailau Pl 25 of 41 Listing Image for 235 Wailau Pl 26 of 41 Listing Image for 235 Wailau Pl 27 of 41 Listing Image for 235 Wailau Pl 28 of 41 Listing Image for 235 Wailau Pl 29 of 41 Listing Image for 235 Wailau Pl 30 of 41 Listing Image for 235 Wailau Pl 31 of 41 Listing Image for 235 Wailau Pl 32 of 41 Listing Image for 235 Wailau Pl 33 of 41 Listing Image for 235 Wailau Pl 34 of 41 Listing Image for 235 Wailau Pl 35 of 41 Listing Image for 235 Wailau Pl 36 of 41 Listing Image for 235 Wailau Pl 37 of 41 Listing Image for 235 Wailau Pl 38 of 41 Listing Image for 235 Wailau Pl 39 of 41 Listing Image for 235 Wailau Pl 40 of 41 Listing Image for 235 Wailau Pl 41 of 41

$2,950,000

Mahanalua Nui

235 Wailau Pl, Lahaina

4 Beds 3.5 Baths 2,760 SqFt Residential MLS® # 408463 Date Sold: April 17, 2026
Sold
Closed: 05/11/2026
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$1,130,000

Kahului

189 W Hawaii St, Kahului

4 Beds 3 Baths 2,432 SqFt Residential MLS® # 408457 Date Sold: May 11, 2026
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Consider a Bridge Loan

When looking at how to buy a house before selling yours, a bridge loan may be a great solution. A bridge loan, a short-term loan with a higher interest rate, can be used to refinance your current home mortgage or pull equity out as a second lien.

With interest-only payments, you can tap into your equity to use as a down payment to purchase a second home. You can also potentially decrease your first home’s mortgage payments, which will be beneficial if the closing dates do not align perfectly.

Choose a Low Down Payment Loan Program

While many mortgage lenders will require you to make a sizable down payment when you buy a house, there are lending solutions available that allow you to put down 5% or less. A Fannie Mae loan, for example, only requires 3% down. While the interest rates on these loans are competitive, you may be responsible for Mortgage Payment Insurance (MPI).

MPI could add hundreds of dollars to your monthly mortgage payment. With a low down payment loan, however, you may not need to access your current home’s equity to complete your purchase.

Borrow Against Your Retirement Account

Generally, your retirement account’s funds are inaccessible to you until you reach the age of 59.5 years old. Most withdrawals taken before you reach this age can trigger a penalty and will be taxable. However, the IRS allows you to withdraw funds without penalty to buy a house.

There are specific rules and requirements that you should research thoroughly before pursuing this option. Your retirement account funds can be used for a down payment as well as closing costs, and this could eliminate the need to sell your house before buying a new one.

Add a Contingency to the Sales Contract

If you have determined that the other options available are not suitable for your unique situation, another possibility is available. When considering how to buy a second home without selling the first, a sales contingency could be written into the new sales contract. A sales contingency can be worded so that your purchase is dependent on the sale of the current house. 

While this can seem like the perfect solution, be aware that many sellers may not accept this contingency. Like you, other sellers may be trying to sell their house to buy another property. If they delay their sale because of a sales contingency, they may not be able to structure their own timeline to suit their needs. Your real estate agent can work with you to structure a sales contingency with an agreeable seller.

Turn Your Home Into an Investment Property

If you are concerned about the possibility of having two mortgage payments at the same time, you could consider renting out your first home. The monthly rent from your rental property could cover its mortgage payment, property taxes, and other expenses. The remaining rental income is a profit that can be used as desired.

If you are unable to qualify for a new home loan for your purchase with the old mortgage in place, renting the property can help. Once you have a signed lease in place on your first home, your mortgage lender can apply that income to your debt-to-income ratio. 

Before turning your home into a rental, consult with your realtor. Your real estate agent can provide you with a fair market rental rate for the property. This information is required to determine if its monthly rent will cover its expenses. The IRS allows you to write off many property expenses, including upkeep costs, management fees, property taxes, etc. Depending on the situation, a property owner could possibly turn a profit on a rental house while enjoying a tax loss.

Consider Buying a Second Home

Buying a second home has advantages to consider as well. If you buy a second home, you can enjoy traveling back and forth between the locations as desired. When you are not using a home for personal use, you could rent it out as a rental property. A second home also has tax benefits

Even if you do not use the second home to produce rental income, you may qualify for the same homeowner tax deductions as you benefit from with your first home. Before buying a second home or turning your current home into a rental property, consider speaking to a tax advisor and a management company to explore all of the financial ramifications in detail.

Executing a 1031 Exchange

1031 Exchange Maui

When doing a 1031 exchange, you'll typically be selling the property you are going to exchange first and then immedietley seeking a replacement property. Read my full rundown on how to successfully navigate the process here

Explore Your Options Today

Keep in mind that you can combine multiple solutions presented here as you walk through the real estate process. For example, you could take out a home equity loan on your current home to access down payment funds to purchase your second home. At the same time, you could turn your first home into a rental property to generate monthly income.

This example is only one of many ways to combine these solutions and set up a scenario that suits your needs. Contact a local real estate agent to learn more about the housing and rental market.

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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