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. 

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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: 03/20/2026
Listing Image for 107 Kinohi Loa St 1 of 50 Listing Image for 107 Kinohi Loa St 2 of 50 Listing Image for 107 Kinohi Loa St 3 of 50 Listing Image for 107 Kinohi Loa St 4 of 50 Listing Image for 107 Kinohi Loa St 5 of 50 Listing Image for 107 Kinohi Loa St 6 of 50 Listing Image for 107 Kinohi Loa St 7 of 50 Listing Image for 107 Kinohi Loa St 8 of 50 Listing Image for 107 Kinohi Loa St 9 of 50 Listing Image for 107 Kinohi Loa St 10 of 50 Listing Image for 107 Kinohi Loa St 11 of 50 Listing Image for 107 Kinohi Loa St 12 of 50 Listing Image for 107 Kinohi Loa St 13 of 50 Listing Image for 107 Kinohi Loa St 14 of 50 Listing Image for 107 Kinohi Loa St 15 of 50 Listing Image for 107 Kinohi Loa St 16 of 50 Listing Image for 107 Kinohi Loa St 17 of 50 Listing Image for 107 Kinohi Loa St 18 of 50 Listing Image for 107 Kinohi Loa St 19 of 50 Listing Image for 107 Kinohi Loa St 20 of 50 Listing Image for 107 Kinohi Loa St 21 of 50 Listing Image for 107 Kinohi Loa St 22 of 50 Listing Image for 107 Kinohi Loa St 23 of 50 Listing Image for 107 Kinohi Loa St 24 of 50 Listing Image for 107 Kinohi Loa St 25 of 50 Listing Image for 107 Kinohi Loa St 26 of 50 Listing Image for 107 Kinohi Loa St 27 of 50 Listing Image for 107 Kinohi Loa St 28 of 50 Listing Image for 107 Kinohi Loa St 29 of 50 Listing Image for 107 Kinohi Loa St 30 of 50 Listing Image for 107 Kinohi Loa St 31 of 50 Listing Image for 107 Kinohi Loa St 32 of 50 Listing Image for 107 Kinohi Loa St 33 of 50 Listing Image for 107 Kinohi Loa St 34 of 50 Listing Image for 107 Kinohi Loa St 35 of 50 Listing Image for 107 Kinohi Loa St 36 of 50 Listing Image for 107 Kinohi Loa St 37 of 50 Listing Image for 107 Kinohi Loa St 38 of 50 Listing Image for 107 Kinohi Loa St 39 of 50 Listing Image for 107 Kinohi Loa St 40 of 50 Listing Image for 107 Kinohi Loa St 41 of 50 Listing Image for 107 Kinohi Loa St 42 of 50 Listing Image for 107 Kinohi Loa St 43 of 50 Listing Image for 107 Kinohi Loa St 44 of 50 Listing Image for 107 Kinohi Loa St 45 of 50 Listing Image for 107 Kinohi Loa St 46 of 50 Listing Image for 107 Kinohi Loa St 47 of 50 Listing Image for 107 Kinohi Loa St 48 of 50 Listing Image for 107 Kinohi Loa St 49 of 50 Listing Image for 107 Kinohi Loa St 50 of 50

$1,206,500

↓ $118,500

Cottages at Kehalani

107 Kinohi Loa St, Wailuku

3 Beds 2.5 Baths 1,824 SqFt Residential MLS® # 405832 Date Sold: March 20, 2026
Sold
Closed: 07/24/2025
Listing Image for 231 Leinani Dr 1 of 48 Listing Image for 231 Leinani Dr 2 of 48 Listing Image for 231 Leinani Dr 3 of 48 Listing Image for 231 Leinani Dr 4 of 48 Listing Image for 231 Leinani Dr 5 of 48 Listing Image for 231 Leinani Dr 6 of 48 Listing Image for 231 Leinani Dr 7 of 48 Listing Image for 231 Leinani Dr 8 of 48 Listing Image for 231 Leinani Dr 9 of 48 Listing Image for 231 Leinani Dr 10 of 48 Listing Image for 231 Leinani Dr 11 of 48 Listing Image for 231 Leinani Dr 12 of 48 Listing Image for 231 Leinani Dr 13 of 48 Listing Image for 231 Leinani Dr 14 of 48 Listing Image for 231 Leinani Dr 15 of 48 Listing Image for 231 Leinani Dr 16 of 48 Listing Image for 231 Leinani Dr 17 of 48 Listing Image for 231 Leinani Dr 18 of 48 Listing Image for 231 Leinani Dr 19 of 48 Listing Image for 231 Leinani Dr 20 of 48 Listing Image for 231 Leinani Dr 21 of 48 Listing Image for 231 Leinani Dr 22 of 48 Listing Image for 231 Leinani Dr 23 of 48 Listing Image for 231 Leinani Dr 24 of 48 Listing Image for 231 Leinani Dr 25 of 48 Listing Image for 231 Leinani Dr 26 of 48 Listing Image for 231 Leinani Dr 27 of 48 Listing Image for 231 Leinani Dr 28 of 48 Listing Image for 231 Leinani Dr 29 of 48 Listing Image for 231 Leinani Dr 30 of 48 Listing Image for 231 Leinani Dr 31 of 48 Listing Image for 231 Leinani Dr 32 of 48 Listing Image for 231 Leinani Dr 33 of 48 Listing Image for 231 Leinani Dr 34 of 48 Listing Image for 231 Leinani Dr 35 of 48 Listing Image for 231 Leinani Dr 36 of 48 Listing Image for 231 Leinani Dr 37 of 48 Listing Image for 231 Leinani Dr 38 of 48 Listing Image for 231 Leinani Dr 39 of 48 Listing Image for 231 Leinani Dr 40 of 48 Listing Image for 231 Leinani Dr 41 of 48 Listing Image for 231 Leinani Dr 42 of 48 Listing Image for 231 Leinani Dr 43 of 48 Listing Image for 231 Leinani Dr 44 of 48 Listing Image for 231 Leinani Dr 45 of 48 Listing Image for 231 Leinani Dr 46 of 48 Listing Image for 231 Leinani Dr 47 of 48 Listing Image for 231 Leinani Dr 48 of 48

$1,450,000

Fleming Tract

231 Leinani Dr, Wailuku

5 Beds 4 Baths 3,240 SqFt Residential MLS® # 405629 Date Sold: July 24, 2025
Sold
Closed: 09/02/2025
Listing Image for 18 Olina St 63 1 of 39 Listing Image for 18 Olina St 63 2 of 39 Listing Image for 18 Olina St 63 3 of 39 Listing Image for 18 Olina St 63 4 of 39 Listing Image for 18 Olina St 63 5 of 39 Listing Image for 18 Olina St 63 6 of 39 Listing Image for 18 Olina St 63 7 of 39 Listing Image for 18 Olina St 63 8 of 39 Listing Image for 18 Olina St 63 9 of 39 Listing Image for 18 Olina St 63 10 of 39 Listing Image for 18 Olina St 63 11 of 39 Listing Image for 18 Olina St 63 12 of 39 Listing Image for 18 Olina St 63 13 of 39 Listing Image for 18 Olina St 63 14 of 39 Listing Image for 18 Olina St 63 15 of 39 Listing Image for 18 Olina St 63 16 of 39 Listing Image for 18 Olina St 63 17 of 39 Listing Image for 18 Olina St 63 18 of 39 Listing Image for 18 Olina St 63 19 of 39 Listing Image for 18 Olina St 63 20 of 39 Listing Image for 18 Olina St 63 21 of 39 Listing Image for 18 Olina St 63 22 of 39 Listing Image for 18 Olina St 63 23 of 39 Listing Image for 18 Olina St 63 24 of 39 Listing Image for 18 Olina St 63 25 of 39 Listing Image for 18 Olina St 63 26 of 39 Listing Image for 18 Olina St 63 27 of 39 Listing Image for 18 Olina St 63 28 of 39 Listing Image for 18 Olina St 63 29 of 39 Listing Image for 18 Olina St 63 30 of 39 Listing Image for 18 Olina St 63 31 of 39 Listing Image for 18 Olina St 63 32 of 39 Listing Image for 18 Olina St 63 33 of 39 Listing Image for 18 Olina St 63 34 of 39 Listing Image for 18 Olina St 63 35 of 39 Listing Image for 18 Olina St 63 36 of 39 Listing Image for 18 Olina St 63 37 of 39 Listing Image for 18 Olina St 63 38 of 39 Listing Image for 18 Olina St 63 39 of 39

$1,415,000

Kahului

18 Olina St 63, Kahului

4 Beds 2.5 Baths 2,404 SqFt Residential MLS® # 405861 Date Sold: September 2, 2025
Sold
Closed: 09/05/2025
Listing Image for 811 S Kihei Rd 5h 1 of 48 Listing Image for 811 S Kihei Rd 5h 2 of 48 Listing Image for 811 S Kihei Rd 5h 3 of 48 Listing Image for 811 S Kihei Rd 5h 4 of 48 Listing Image for 811 S Kihei Rd 5h 5 of 48 Listing Image for 811 S Kihei Rd 5h 6 of 48 Listing Image for 811 S Kihei Rd 5h 7 of 48 Listing Image for 811 S Kihei Rd 5h 8 of 48 Listing Image for 811 S Kihei Rd 5h 9 of 48 Listing Image for 811 S Kihei Rd 5h 10 of 48 Listing Image for 811 S Kihei Rd 5h 11 of 48 Listing Image for 811 S Kihei Rd 5h 12 of 48 Listing Image for 811 S Kihei Rd 5h 13 of 48 Listing Image for 811 S Kihei Rd 5h 14 of 48 Listing Image for 811 S Kihei Rd 5h 15 of 48 Listing Image for 811 S Kihei Rd 5h 16 of 48 Listing Image for 811 S Kihei Rd 5h 17 of 48 Listing Image for 811 S Kihei Rd 5h 18 of 48 Listing Image for 811 S Kihei Rd 5h 19 of 48 Listing Image for 811 S Kihei Rd 5h 20 of 48 Listing Image for 811 S Kihei Rd 5h 21 of 48 Listing Image for 811 S Kihei Rd 5h 22 of 48 Listing Image for 811 S Kihei Rd 5h 23 of 48 Listing Image for 811 S Kihei Rd 5h 24 of 48 Listing Image for 811 S Kihei Rd 5h 25 of 48 Listing Image for 811 S Kihei Rd 5h 26 of 48 Listing Image for 811 S Kihei Rd 5h 27 of 48 Listing Image for 811 S Kihei Rd 5h 28 of 48 Listing Image for 811 S Kihei Rd 5h 29 of 48 Listing Image for 811 S Kihei Rd 5h 30 of 48 Listing Image for 811 S Kihei Rd 5h 31 of 48 Listing Image for 811 S Kihei Rd 5h 32 of 48 Listing Image for 811 S Kihei Rd 5h 33 of 48 Listing Image for 811 S Kihei Rd 5h 34 of 48 Listing Image for 811 S Kihei Rd 5h 35 of 48 Listing Image for 811 S Kihei Rd 5h 36 of 48 Listing Image for 811 S Kihei Rd 5h 37 of 48 Listing Image for 811 S Kihei Rd 5h 38 of 48 Listing Image for 811 S Kihei Rd 5h 39 of 48 Listing Image for 811 S Kihei Rd 5h 40 of 48 Listing Image for 811 S Kihei Rd 5h 41 of 48 Listing Image for 811 S Kihei Rd 5h 42 of 48 Listing Image for 811 S Kihei Rd 5h 43 of 48 Listing Image for 811 S Kihei Rd 5h 44 of 48 Listing Image for 811 S Kihei Rd 5h 45 of 48 Listing Image for 811 S Kihei Rd 5h 46 of 48 Listing Image for 811 S Kihei Rd 5h 47 of 48 Listing Image for 811 S Kihei Rd 5h 48 of 48

$840,000

Koa Resort 5H

811 S Kihei Rd 5h, Kihei

2 Beds 2 Baths 1,066 SqFt Residential MLS® # 405386 Date Sold: September 5, 2025
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: 11/21/2025
Listing Image for 203 Hoalike St 1 of 17 Listing Image for 203 Hoalike St 2 of 17 Listing Image for 203 Hoalike St 3 of 17 Listing Image for 203 Hoalike St 4 of 17 Listing Image for 203 Hoalike St 5 of 17 Listing Image for 203 Hoalike St 6 of 17 Listing Image for 203 Hoalike St 7 of 17 Listing Image for 203 Hoalike St 8 of 17 Listing Image for 203 Hoalike St 9 of 17 Listing Image for 203 Hoalike St 10 of 17 Listing Image for 203 Hoalike St 11 of 17 Listing Image for 203 Hoalike St 12 of 17 Listing Image for 203 Hoalike St 13 of 17 Listing Image for 203 Hoalike St 14 of 17 Listing Image for 203 Hoalike St 15 of 17 Listing Image for 203 Hoalike St 16 of 17 Listing Image for 203 Hoalike St 17 of 17

$800,000

Kihei

203 Hoalike St, Kihei

2 Beds 1 Bath 864 SqFt Residential MLS® # 405777 Date Sold: November 21, 2025
Sold
Closed: 08/24/2026
Listing Image for 89 Kupalaiki Loop 1 of 40 Listing Image for 89 Kupalaiki Loop 2 of 40 Listing Image for 89 Kupalaiki Loop 3 of 40 Listing Image for 89 Kupalaiki Loop 4 of 40 Listing Image for 89 Kupalaiki Loop 5 of 40 Listing Image for 89 Kupalaiki Loop 6 of 40 Listing Image for 89 Kupalaiki Loop 7 of 40 Listing Image for 89 Kupalaiki Loop 8 of 40 Listing Image for 89 Kupalaiki Loop 9 of 40 Listing Image for 89 Kupalaiki Loop 10 of 40 Listing Image for 89 Kupalaiki Loop 11 of 40 Listing Image for 89 Kupalaiki Loop 12 of 40 Listing Image for 89 Kupalaiki Loop 13 of 40 Listing Image for 89 Kupalaiki Loop 14 of 40 Listing Image for 89 Kupalaiki Loop 15 of 40 Listing Image for 89 Kupalaiki Loop 16 of 40 Listing Image for 89 Kupalaiki Loop 17 of 40 Listing Image for 89 Kupalaiki Loop 18 of 40 Listing Image for 89 Kupalaiki Loop 19 of 40 Listing Image for 89 Kupalaiki Loop 20 of 40 Listing Image for 89 Kupalaiki Loop 21 of 40 Listing Image for 89 Kupalaiki Loop 22 of 40 Listing Image for 89 Kupalaiki Loop 23 of 40 Listing Image for 89 Kupalaiki Loop 24 of 40 Listing Image for 89 Kupalaiki Loop 25 of 40 Listing Image for 89 Kupalaiki Loop 26 of 40 Listing Image for 89 Kupalaiki Loop 27 of 40 Listing Image for 89 Kupalaiki Loop 28 of 40 Listing Image for 89 Kupalaiki Loop 29 of 40 Listing Image for 89 Kupalaiki Loop 30 of 40 Listing Image for 89 Kupalaiki Loop 31 of 40 Listing Image for 89 Kupalaiki Loop 32 of 40 Listing Image for 89 Kupalaiki Loop 33 of 40 Listing Image for 89 Kupalaiki Loop 34 of 40 Listing Image for 89 Kupalaiki Loop 35 of 40 Listing Image for 89 Kupalaiki Loop 36 of 40 Listing Image for 89 Kupalaiki Loop 37 of 40 Listing Image for 89 Kupalaiki Loop 38 of 40 Listing Image for 89 Kupalaiki Loop 39 of 40 Listing Image for 89 Kupalaiki Loop 40 of 40

$910,000

↓ $290,000

Kauhale Nani

89 Kupalaiki Loop, Kihei

3 Beds 1.5 Baths 1,344 SqFt Residential MLS® # 406565 Date Sold: August 24, 2026
View 6 More Listings

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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