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: 07/09/2025
Listing Image for 300 Kolohala Dr 1 of 21 Listing Image for 300 Kolohala Dr 2 of 21 Listing Image for 300 Kolohala Dr 3 of 21 Listing Image for 300 Kolohala Dr 4 of 21 Listing Image for 300 Kolohala Dr 5 of 21 Listing Image for 300 Kolohala Dr 6 of 21 Listing Image for 300 Kolohala Dr 7 of 21 Listing Image for 300 Kolohala Dr 8 of 21 Listing Image for 300 Kolohala Dr 9 of 21 Listing Image for 300 Kolohala Dr 10 of 21 Listing Image for 300 Kolohala Dr 11 of 21 Listing Image for 300 Kolohala Dr 12 of 21 Listing Image for 300 Kolohala Dr 13 of 21 Listing Image for 300 Kolohala Dr 14 of 21 Listing Image for 300 Kolohala Dr 15 of 21 Listing Image for 300 Kolohala Dr 16 of 21 Listing Image for 300 Kolohala Dr 17 of 21 Listing Image for 300 Kolohala Dr 18 of 21 Listing Image for 300 Kolohala Dr 19 of 21 Listing Image for 300 Kolohala Dr 20 of 21 Listing Image for 300 Kolohala Dr 21 of 21

$970,000

Kealahou Farm Lots

300 Kolohala Dr, Kula/Ulupalakua/Kanaio

2 Beds 1 Bath 692 SqFt Residential MLS® # 406103 Date Sold: July 9, 2025
Sold
Closed: 07/09/2025
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$1,675,000

Kula/Ulupalakua/Kanaio

1515 Lower Kimo Dr, Kula/Ulupalakua/Kanaio

4 Beds 3.5 Baths 2,971 SqFt Residential MLS® # 405641 Date Sold: July 9, 2025
Sold
Closed: 07/15/2025
Listing Image for 485 Kaiwahine St 1 of 46 Listing Image for 485 Kaiwahine St 2 of 46 Listing Image for 485 Kaiwahine St 3 of 46 Listing Image for 485 Kaiwahine St 4 of 46 Listing Image for 485 Kaiwahine St 5 of 46 Listing Image for 485 Kaiwahine St 6 of 46 Listing Image for 485 Kaiwahine St 7 of 46 Listing Image for 485 Kaiwahine St 8 of 46 Listing Image for 485 Kaiwahine St 9 of 46 Listing Image for 485 Kaiwahine St 10 of 46 Listing Image for 485 Kaiwahine St 11 of 46 Listing Image for 485 Kaiwahine St 12 of 46 Listing Image for 485 Kaiwahine St 13 of 46 Listing Image for 485 Kaiwahine St 14 of 46 Listing Image for 485 Kaiwahine St 15 of 46 Listing Image for 485 Kaiwahine St 16 of 46 Listing Image for 485 Kaiwahine St 17 of 46 Listing Image for 485 Kaiwahine St 18 of 46 Listing Image for 485 Kaiwahine St 19 of 46 Listing Image for 485 Kaiwahine St 20 of 46 Listing Image for 485 Kaiwahine St 21 of 46 Listing Image for 485 Kaiwahine St 22 of 46 Listing Image for 485 Kaiwahine St 23 of 46 Listing Image for 485 Kaiwahine St 24 of 46 Listing Image for 485 Kaiwahine St 25 of 46 Listing Image for 485 Kaiwahine St 26 of 46 Listing Image for 485 Kaiwahine St 27 of 46 Listing Image for 485 Kaiwahine St 28 of 46 Listing Image for 485 Kaiwahine St 29 of 46 Listing Image for 485 Kaiwahine St 30 of 46 Listing Image for 485 Kaiwahine St 31 of 46 Listing Image for 485 Kaiwahine St 32 of 46 Listing Image for 485 Kaiwahine St 33 of 46 Listing Image for 485 Kaiwahine St 34 of 46 Listing Image for 485 Kaiwahine St 35 of 46 Listing Image for 485 Kaiwahine St 36 of 46 Listing Image for 485 Kaiwahine St 37 of 46 Listing Image for 485 Kaiwahine St 38 of 46 Listing Image for 485 Kaiwahine St 39 of 46 Listing Image for 485 Kaiwahine St 40 of 46 Listing Image for 485 Kaiwahine St 41 of 46 Listing Image for 485 Kaiwahine St 42 of 46 Listing Image for 485 Kaiwahine St 43 of 46 Listing Image for 485 Kaiwahine St 44 of 46 Listing Image for 485 Kaiwahine St 45 of 46 Listing Image for 485 Kaiwahine St 46 of 46

$1,400,000

Hale Piilani

485 Kaiwahine St, Kihei

3 Beds 2 Baths 1,708 SqFt Residential MLS® # 405007 Date Sold: July 15, 2025
Sold
Closed: 08/27/2025
Listing Image for 3800 Wailea Alanui St E201 1 of 45 Listing Image for 3800 Wailea Alanui St E201 2 of 45 Listing Image for 3800 Wailea Alanui St E201 3 of 45 Listing Image for 3800 Wailea Alanui St E201 4 of 45 Listing Image for 3800 Wailea Alanui St E201 5 of 45 Listing Image for 3800 Wailea Alanui St E201 6 of 45 Listing Image for 3800 Wailea Alanui St E201 7 of 45 Listing Image for 3800 Wailea Alanui St E201 8 of 45 Listing Image for 3800 Wailea Alanui St E201 9 of 45 Listing Image for 3800 Wailea Alanui St E201 10 of 45 Listing Image for 3800 Wailea Alanui St E201 11 of 45 Listing Image for 3800 Wailea Alanui St E201 12 of 45 Listing Image for 3800 Wailea Alanui St E201 13 of 45 Listing Image for 3800 Wailea Alanui St E201 14 of 45 Listing Image for 3800 Wailea Alanui St E201 15 of 45 Listing Image for 3800 Wailea Alanui St E201 16 of 45 Listing Image for 3800 Wailea Alanui St E201 17 of 45 Listing Image for 3800 Wailea Alanui St E201 18 of 45 Listing Image for 3800 Wailea Alanui St E201 19 of 45 Listing Image for 3800 Wailea Alanui St E201 20 of 45 Listing Image for 3800 Wailea Alanui St E201 21 of 45 Listing Image for 3800 Wailea Alanui St E201 22 of 45 Listing Image for 3800 Wailea Alanui St E201 23 of 45 Listing Image for 3800 Wailea Alanui St E201 24 of 45 Listing Image for 3800 Wailea Alanui St E201 25 of 45 Listing Image for 3800 Wailea Alanui St E201 26 of 45 Listing Image for 3800 Wailea Alanui St E201 27 of 45 Listing Image for 3800 Wailea Alanui St E201 28 of 45 Listing Image for 3800 Wailea Alanui St E201 29 of 45 Listing Image for 3800 Wailea Alanui St E201 30 of 45 Listing Image for 3800 Wailea Alanui St E201 31 of 45 Listing Image for 3800 Wailea Alanui St E201 32 of 45 Listing Image for 3800 Wailea Alanui St E201 33 of 45 Listing Image for 3800 Wailea Alanui St E201 34 of 45 Listing Image for 3800 Wailea Alanui St E201 35 of 45 Listing Image for 3800 Wailea Alanui St E201 36 of 45 Listing Image for 3800 Wailea Alanui St E201 37 of 45 Listing Image for 3800 Wailea Alanui St E201 38 of 45 Listing Image for 3800 Wailea Alanui St E201 39 of 45 Listing Image for 3800 Wailea Alanui St E201 40 of 45 Listing Image for 3800 Wailea Alanui St E201 41 of 45 Listing Image for 3800 Wailea Alanui St E201 42 of 45 Listing Image for 3800 Wailea Alanui St E201 43 of 45 Listing Image for 3800 Wailea Alanui St E201 44 of 45 Listing Image for 3800 Wailea Alanui St E201 45 of 45

$6,185,000

Wailea Beach Villas E201

3800 Wailea Alanui St E201, Wailea/Makena

3 Beds 3.5 Baths 2,879 SqFt Residential MLS® # 406476 Date Sold: August 27, 2025
Sold
Closed: 08/28/2025
Listing Image for 700 Kaimana St 1 of 12 Listing Image for 700 Kaimana St 2 of 12 Listing Image for 700 Kaimana St 3 of 12 Listing Image for 700 Kaimana St 4 of 12 Listing Image for 700 Kaimana St 5 of 12 Listing Image for 700 Kaimana St 6 of 12 Listing Image for 700 Kaimana St 7 of 12 Listing Image for 700 Kaimana St 8 of 12 Listing Image for 700 Kaimana St 9 of 12 Listing Image for 700 Kaimana St 10 of 12 Listing Image for 700 Kaimana St 11 of 12 Listing Image for 700 Kaimana St 12 of 12

$1,171,000

Kahului

700 Kaimana St, Kahului

5 Beds 2.5 Baths 1,760 SqFt Residential MLS® # 406474 Date Sold: August 28, 2025
Sold
Closed: 06/12/2026
Listing Image for 26 E Mahi Pua Pl 1 of 49 Listing Image for 26 E Mahi Pua Pl 2 of 49 Listing Image for 26 E Mahi Pua Pl 3 of 49 Listing Image for 26 E Mahi Pua Pl 4 of 49 Listing Image for 26 E Mahi Pua Pl 5 of 49 Listing Image for 26 E Mahi Pua Pl 6 of 49 Listing Image for 26 E Mahi Pua Pl 7 of 49 Listing Image for 26 E Mahi Pua Pl 8 of 49 Listing Image for 26 E Mahi Pua Pl 9 of 49 Listing Image for 26 E Mahi Pua Pl 10 of 49 Listing Image for 26 E Mahi Pua Pl 11 of 49 Listing Image for 26 E Mahi Pua Pl 12 of 49 Listing Image for 26 E Mahi Pua Pl 13 of 49 Listing Image for 26 E Mahi Pua Pl 14 of 49 Listing Image for 26 E Mahi Pua Pl 15 of 49 Listing Image for 26 E Mahi Pua Pl 16 of 49 Listing Image for 26 E Mahi Pua Pl 17 of 49 Listing Image for 26 E Mahi Pua Pl 18 of 49 Listing Image for 26 E Mahi Pua Pl 19 of 49 Listing Image for 26 E Mahi Pua Pl 20 of 49 Listing Image for 26 E Mahi Pua Pl 21 of 49 Listing Image for 26 E Mahi Pua Pl 22 of 49 Listing Image for 26 E Mahi Pua Pl 23 of 49 Listing Image for 26 E Mahi Pua Pl 24 of 49 Listing Image for 26 E Mahi Pua Pl 25 of 49 Listing Image for 26 E Mahi Pua Pl 26 of 49 Listing Image for 26 E Mahi Pua Pl 27 of 49 Listing Image for 26 E Mahi Pua Pl 28 of 49 Listing Image for 26 E Mahi Pua Pl 29 of 49 Listing Image for 26 E Mahi Pua Pl 30 of 49 Listing Image for 26 E Mahi Pua Pl 31 of 49 Listing Image for 26 E Mahi Pua Pl 32 of 49 Listing Image for 26 E Mahi Pua Pl 33 of 49 Listing Image for 26 E Mahi Pua Pl 34 of 49 Listing Image for 26 E Mahi Pua Pl 35 of 49 Listing Image for 26 E Mahi Pua Pl 36 of 49 Listing Image for 26 E Mahi Pua Pl 37 of 49 Listing Image for 26 E Mahi Pua Pl 38 of 49 Listing Image for 26 E Mahi Pua Pl 39 of 49 Listing Image for 26 E Mahi Pua Pl 40 of 49 Listing Image for 26 E Mahi Pua Pl 41 of 49 Listing Image for 26 E Mahi Pua Pl 42 of 49 Listing Image for 26 E Mahi Pua Pl 43 of 49 Listing Image for 26 E Mahi Pua Pl 44 of 49 Listing Image for 26 E Mahi Pua Pl 45 of 49 Listing Image for 26 E Mahi Pua Pl 46 of 49 Listing Image for 26 E Mahi Pua Pl 47 of 49 Listing Image for 26 E Mahi Pua Pl 48 of 49 Listing Image for 26 E Mahi Pua Pl 49 of 49

$3,700,000

↓ $795,000

Pinnacle

26 E Mahi Pua Pl, Kaanapali

4 Beds 4.5 Baths 4,415 SqFt Residential MLS® # 405458 Date Sold: June 12, 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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