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: 09/15/2025
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$1,895,000

Yokote Subdivision

806 Kukia Pl, Kula/Ulupalakua/Kanaio

3 Beds 2 Baths 1,948 SqFt Residential MLS® # 406249 Date Sold: September 15, 2025
Sold
Closed: 08/29/2025
Listing Image for 2038 Kahekili Hwy 1 of 48 Listing Image for 2038 Kahekili Hwy 2 of 48 Listing Image for 2038 Kahekili Hwy 3 of 48 Listing Image for 2038 Kahekili Hwy 4 of 48 Listing Image for 2038 Kahekili Hwy 5 of 48 Listing Image for 2038 Kahekili Hwy 6 of 48 Listing Image for 2038 Kahekili Hwy 7 of 48 Listing Image for 2038 Kahekili Hwy 8 of 48 Listing Image for 2038 Kahekili Hwy 9 of 48 Listing Image for 2038 Kahekili Hwy 10 of 48 Listing Image for 2038 Kahekili Hwy 11 of 48 Listing Image for 2038 Kahekili Hwy 12 of 48 Listing Image for 2038 Kahekili Hwy 13 of 48 Listing Image for 2038 Kahekili Hwy 14 of 48 Listing Image for 2038 Kahekili Hwy 15 of 48 Listing Image for 2038 Kahekili Hwy 16 of 48 Listing Image for 2038 Kahekili Hwy 17 of 48 Listing Image for 2038 Kahekili Hwy 18 of 48 Listing Image for 2038 Kahekili Hwy 19 of 48 Listing Image for 2038 Kahekili Hwy 20 of 48 Listing Image for 2038 Kahekili Hwy 21 of 48 Listing Image for 2038 Kahekili Hwy 22 of 48 Listing Image for 2038 Kahekili Hwy 23 of 48 Listing Image for 2038 Kahekili Hwy 24 of 48 Listing Image for 2038 Kahekili Hwy 25 of 48 Listing Image for 2038 Kahekili Hwy 26 of 48 Listing Image for 2038 Kahekili Hwy 27 of 48 Listing Image for 2038 Kahekili Hwy 28 of 48 Listing Image for 2038 Kahekili Hwy 29 of 48 Listing Image for 2038 Kahekili Hwy 30 of 48 Listing Image for 2038 Kahekili Hwy 31 of 48 Listing Image for 2038 Kahekili Hwy 32 of 48 Listing Image for 2038 Kahekili Hwy 33 of 48 Listing Image for 2038 Kahekili Hwy 34 of 48 Listing Image for 2038 Kahekili Hwy 35 of 48 Listing Image for 2038 Kahekili Hwy 36 of 48 Listing Image for 2038 Kahekili Hwy 37 of 48 Listing Image for 2038 Kahekili Hwy 38 of 48 Listing Image for 2038 Kahekili Hwy 39 of 48 Listing Image for 2038 Kahekili Hwy 40 of 48 Listing Image for 2038 Kahekili Hwy 41 of 48 Listing Image for 2038 Kahekili Hwy 42 of 48 Listing Image for 2038 Kahekili Hwy 43 of 48 Listing Image for 2038 Kahekili Hwy 44 of 48 Listing Image for 2038 Kahekili Hwy 45 of 48 Listing Image for 2038 Kahekili Hwy 46 of 48 Listing Image for 2038 Kahekili Hwy 47 of 48 Listing Image for 2038 Kahekili Hwy 48 of 48

$1,399,000

Wailuku

2038 Kahekili Hwy, Wailuku

3 Beds 2 Baths 1,356 SqFt Residential MLS® # 405994 Date Sold: August 29, 2025
Sold
Closed: 03/27/2026
Listing Image for 244 N Makaleha Pl 1 of 28 Listing Image for 244 N Makaleha Pl 2 of 28 Listing Image for 244 N Makaleha Pl 3 of 28 Listing Image for 244 N Makaleha Pl 4 of 28 Listing Image for 244 N Makaleha Pl 5 of 28 Listing Image for 244 N Makaleha Pl 6 of 28 Listing Image for 244 N Makaleha Pl 7 of 28 Listing Image for 244 N Makaleha Pl 8 of 28 Listing Image for 244 N Makaleha Pl 9 of 28 Listing Image for 244 N Makaleha Pl 10 of 28 Listing Image for 244 N Makaleha Pl 11 of 28 Listing Image for 244 N Makaleha Pl 12 of 28 Listing Image for 244 N Makaleha Pl 13 of 28 Listing Image for 244 N Makaleha Pl 14 of 28 Listing Image for 244 N Makaleha Pl 15 of 28 Listing Image for 244 N Makaleha Pl 16 of 28 Listing Image for 244 N Makaleha Pl 17 of 28 Listing Image for 244 N Makaleha Pl 18 of 28 Listing Image for 244 N Makaleha Pl 19 of 28 Listing Image for 244 N Makaleha Pl 20 of 28 Listing Image for 244 N Makaleha Pl 21 of 28 Listing Image for 244 N Makaleha Pl 22 of 28 Listing Image for 244 N Makaleha Pl 23 of 28 Listing Image for 244 N Makaleha Pl 24 of 28 Listing Image for 244 N Makaleha Pl 25 of 28 Listing Image for 244 N Makaleha Pl 26 of 28 Listing Image for 244 N Makaleha Pl 27 of 28 Listing Image for 244 N Makaleha Pl 28 of 28

$800,000

↓ $375,000

Makawao/Olinda/Haliimaile

244 N Makaleha Pl, Makawao/Olinda/Haliimaile

3 Beds 3 Baths 1,774 SqFt Residential MLS® # 405978 Date Sold: March 27, 2026
Sold
Closed: 09/23/2025
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$850,000

Wailuku

1930 E Vineyard St, Wailuku

0 Beds 0 Baths 0 SqFt Commercial Sale MLS® # 405825 Date Sold: September 23, 2025
Sold
Closed: 09/11/2025
Listing Image for 3044 Lower Kula Rd 1 of 44 Listing Image for 3044 Lower Kula Rd 2 of 44 Listing Image for 3044 Lower Kula Rd 3 of 44 Listing Image for 3044 Lower Kula Rd 4 of 44 Listing Image for 3044 Lower Kula Rd 5 of 44 Listing Image for 3044 Lower Kula Rd 6 of 44 Listing Image for 3044 Lower Kula Rd 7 of 44 Listing Image for 3044 Lower Kula Rd 8 of 44 Listing Image for 3044 Lower Kula Rd 9 of 44 Listing Image for 3044 Lower Kula Rd 10 of 44 Listing Image for 3044 Lower Kula Rd 11 of 44 Listing Image for 3044 Lower Kula Rd 12 of 44 Listing Image for 3044 Lower Kula Rd 13 of 44 Listing Image for 3044 Lower Kula Rd 14 of 44 Listing Image for 3044 Lower Kula Rd 15 of 44 Listing Image for 3044 Lower Kula Rd 16 of 44 Listing Image for 3044 Lower Kula Rd 17 of 44 Listing Image for 3044 Lower Kula Rd 18 of 44 Listing Image for 3044 Lower Kula Rd 19 of 44 Listing Image for 3044 Lower Kula Rd 20 of 44 Listing Image for 3044 Lower Kula Rd 21 of 44 Listing Image for 3044 Lower Kula Rd 22 of 44 Listing Image for 3044 Lower Kula Rd 23 of 44 Listing Image for 3044 Lower Kula Rd 24 of 44 Listing Image for 3044 Lower Kula Rd 25 of 44 Listing Image for 3044 Lower Kula Rd 26 of 44 Listing Image for 3044 Lower Kula Rd 27 of 44 Listing Image for 3044 Lower Kula Rd 28 of 44 Listing Image for 3044 Lower Kula Rd 29 of 44 Listing Image for 3044 Lower Kula Rd 30 of 44 Listing Image for 3044 Lower Kula Rd 31 of 44 Listing Image for 3044 Lower Kula Rd 32 of 44 Listing Image for 3044 Lower Kula Rd 33 of 44 Listing Image for 3044 Lower Kula Rd 34 of 44 Listing Image for 3044 Lower Kula Rd 35 of 44 Listing Image for 3044 Lower Kula Rd 36 of 44 Listing Image for 3044 Lower Kula Rd 37 of 44 Listing Image for 3044 Lower Kula Rd 38 of 44 Listing Image for 3044 Lower Kula Rd 39 of 44 Listing Image for 3044 Lower Kula Rd 40 of 44 Listing Image for 3044 Lower Kula Rd 41 of 44 Listing Image for 3044 Lower Kula Rd 42 of 44 Listing Image for 3044 Lower Kula Rd 43 of 44 Listing Image for 3044 Lower Kula Rd 44 of 44

$850,000

Kula/Ulupalakua/Kanaio

3044 Lower Kula Rd, Kula/Ulupalakua/Kanaio

2 Beds 1 Bath 624 SqFt Residential MLS® # 406689 Date Sold: September 11, 2025
Sold
Closed: 12/08/2025
Listing Image for 1899 Keahikano Pl 1 of 37 Listing Image for 1899 Keahikano Pl 2 of 37 Listing Image for 1899 Keahikano Pl 3 of 37 Listing Image for 1899 Keahikano Pl 4 of 37 Listing Image for 1899 Keahikano Pl 5 of 37 Listing Image for 1899 Keahikano Pl 6 of 37 Listing Image for 1899 Keahikano Pl 7 of 37 Listing Image for 1899 Keahikano Pl 8 of 37 Listing Image for 1899 Keahikano Pl 9 of 37 Listing Image for 1899 Keahikano Pl 10 of 37 Listing Image for 1899 Keahikano Pl 11 of 37 Listing Image for 1899 Keahikano Pl 12 of 37 Listing Image for 1899 Keahikano Pl 13 of 37 Listing Image for 1899 Keahikano Pl 14 of 37 Listing Image for 1899 Keahikano Pl 15 of 37 Listing Image for 1899 Keahikano Pl 16 of 37 Listing Image for 1899 Keahikano Pl 17 of 37 Listing Image for 1899 Keahikano Pl 18 of 37 Listing Image for 1899 Keahikano Pl 19 of 37 Listing Image for 1899 Keahikano Pl 20 of 37 Listing Image for 1899 Keahikano Pl 21 of 37 Listing Image for 1899 Keahikano Pl 22 of 37 Listing Image for 1899 Keahikano Pl 23 of 37 Listing Image for 1899 Keahikano Pl 24 of 37 Listing Image for 1899 Keahikano Pl 25 of 37 Listing Image for 1899 Keahikano Pl 26 of 37 Listing Image for 1899 Keahikano Pl 27 of 37 Listing Image for 1899 Keahikano Pl 28 of 37 Listing Image for 1899 Keahikano Pl 29 of 37 Listing Image for 1899 Keahikano Pl 30 of 37 Listing Image for 1899 Keahikano Pl 31 of 37 Listing Image for 1899 Keahikano Pl 32 of 37 Listing Image for 1899 Keahikano Pl 33 of 37 Listing Image for 1899 Keahikano Pl 34 of 37 Listing Image for 1899 Keahikano Pl 35 of 37 Listing Image for 1899 Keahikano Pl 36 of 37 Listing Image for 1899 Keahikano Pl 37 of 37

$1,050,000

Nanea

1899 Keahikano Pl, Wailuku

3 Beds 2 Baths 1,401 SqFt Residential MLS® # 406712 Date Sold: December 8, 2025
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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