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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Listing Image for 379 Maka Hou Loop 1 of 49 Listing Image for 379 Maka Hou Loop 2 of 49 Listing Image for 379 Maka Hou Loop 3 of 49 Listing Image for 379 Maka Hou Loop 4 of 49 Listing Image for 379 Maka Hou Loop 5 of 49 Listing Image for 379 Maka Hou Loop 6 of 49 Listing Image for 379 Maka Hou Loop 7 of 49 Listing Image for 379 Maka Hou Loop 8 of 49 Listing Image for 379 Maka Hou Loop 9 of 49 Listing Image for 379 Maka Hou Loop 10 of 49 Listing Image for 379 Maka Hou Loop 11 of 49 Listing Image for 379 Maka Hou Loop 12 of 49 Listing Image for 379 Maka Hou Loop 13 of 49 Listing Image for 379 Maka Hou Loop 14 of 49 Listing Image for 379 Maka Hou Loop 15 of 49 Listing Image for 379 Maka Hou Loop 16 of 49 Listing Image for 379 Maka Hou Loop 17 of 49 Listing Image for 379 Maka Hou Loop 18 of 49 Listing Image for 379 Maka Hou Loop 19 of 49 Listing Image for 379 Maka Hou Loop 20 of 49 Listing Image for 379 Maka Hou Loop 21 of 49 Listing Image for 379 Maka Hou Loop 22 of 49 Listing Image for 379 Maka Hou Loop 23 of 49 Listing Image for 379 Maka Hou Loop 24 of 49 Listing Image for 379 Maka Hou Loop 25 of 49 Listing Image for 379 Maka Hou Loop 26 of 49 Listing Image for 379 Maka Hou Loop 27 of 49 Listing Image for 379 Maka Hou Loop 28 of 49 Listing Image for 379 Maka Hou Loop 29 of 49 Listing Image for 379 Maka Hou Loop 30 of 49 Listing Image for 379 Maka Hou Loop 31 of 49 Listing Image for 379 Maka Hou Loop 32 of 49 Listing Image for 379 Maka Hou Loop 33 of 49 Listing Image for 379 Maka Hou Loop 34 of 49 Listing Image for 379 Maka Hou Loop 35 of 49 Listing Image for 379 Maka Hou Loop 36 of 49 Listing Image for 379 Maka Hou Loop 37 of 49 Listing Image for 379 Maka Hou Loop 38 of 49 Listing Image for 379 Maka Hou Loop 39 of 49 Listing Image for 379 Maka Hou Loop 40 of 49 Listing Image for 379 Maka Hou Loop 41 of 49 Listing Image for 379 Maka Hou Loop 42 of 49 Listing Image for 379 Maka Hou Loop 43 of 49 Listing Image for 379 Maka Hou Loop 44 of 49 Listing Image for 379 Maka Hou Loop 45 of 49 Listing Image for 379 Maka Hou Loop 46 of 49 Listing Image for 379 Maka Hou Loop 47 of 49 Listing Image for 379 Maka Hou Loop 48 of 49 Listing Image for 379 Maka Hou Loop 49 of 49

$1,550,000

Cottages @ Kehalani

379 Maka Hou Loop, Wailuku

3 Beds 2.5 Baths 1,824 SqFt Residential MLS® # 410458

Days on Market: 38

eXp Realty Cell: 808-870-7162

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$9,195,000

Kihei

1614 Halama St, Kihei

4 Beds 3.5 Baths 3,511 SqFt Residential MLS® # 410457

Days on Market: 38

Coldwell Banker Island Prop-Ku Cell: 808-563-3268

Listing Image for 33 Kokea St 901 1 of 38 Listing Image for 33 Kokea St 901 2 of 38 Listing Image for 33 Kokea St 901 3 of 38 Listing Image for 33 Kokea St 901 4 of 38 Listing Image for 33 Kokea St 901 5 of 38 Listing Image for 33 Kokea St 901 6 of 38 Listing Image for 33 Kokea St 901 7 of 38 Listing Image for 33 Kokea St 901 8 of 38 Listing Image for 33 Kokea St 901 9 of 38 Listing Image for 33 Kokea St 901 10 of 38 Listing Image for 33 Kokea St 901 11 of 38 Listing Image for 33 Kokea St 901 12 of 38 Listing Image for 33 Kokea St 901 13 of 38 Listing Image for 33 Kokea St 901 14 of 38 Listing Image for 33 Kokea St 901 15 of 38 Listing Image for 33 Kokea St 901 16 of 38 Listing Image for 33 Kokea St 901 17 of 38 Listing Image for 33 Kokea St 901 18 of 38 Listing Image for 33 Kokea St 901 19 of 38 Listing Image for 33 Kokea St 901 20 of 38 Listing Image for 33 Kokea St 901 21 of 38 Listing Image for 33 Kokea St 901 22 of 38 Listing Image for 33 Kokea St 901 23 of 38 Listing Image for 33 Kokea St 901 24 of 38 Listing Image for 33 Kokea St 901 25 of 38 Listing Image for 33 Kokea St 901 26 of 38 Listing Image for 33 Kokea St 901 27 of 38 Listing Image for 33 Kokea St 901 28 of 38 Listing Image for 33 Kokea St 901 29 of 38 Listing Image for 33 Kokea St 901 30 of 38 Listing Image for 33 Kokea St 901 31 of 38 Listing Image for 33 Kokea St 901 32 of 38 Listing Image for 33 Kokea St 901 33 of 38 Listing Image for 33 Kokea St 901 34 of 38 Listing Image for 33 Kokea St 901 35 of 38 Listing Image for 33 Kokea St 901 36 of 38 Listing Image for 33 Kokea St 901 37 of 38 Listing Image for 33 Kokea St 901 38 of 38

$1,199,000

Villas at Kehalani 901

33 Kokea St 901, Wailuku

3 Beds 2.5 Baths 1,724 SqFt Residential MLS® # 410456

Days on Market: 38

Island Sotheby's International Realty(M) Cell: 808-357-4444

In Escrow
Listing Image for 162 Anamuli St 1 of 23 Listing Image for 162 Anamuli St 2 of 23 Listing Image for 162 Anamuli St 3 of 23 Listing Image for 162 Anamuli St 4 of 23 Listing Image for 162 Anamuli St 5 of 23 Listing Image for 162 Anamuli St 6 of 23 Listing Image for 162 Anamuli St 7 of 23 Listing Image for 162 Anamuli St 8 of 23 Listing Image for 162 Anamuli St 9 of 23 Listing Image for 162 Anamuli St 10 of 23 Listing Image for 162 Anamuli St 11 of 23 Listing Image for 162 Anamuli St 12 of 23 Listing Image for 162 Anamuli St 13 of 23 Listing Image for 162 Anamuli St 14 of 23 Listing Image for 162 Anamuli St 15 of 23 Listing Image for 162 Anamuli St 16 of 23 Listing Image for 162 Anamuli St 17 of 23 Listing Image for 162 Anamuli St 18 of 23 Listing Image for 162 Anamuli St 19 of 23 Listing Image for 162 Anamuli St 20 of 23 Listing Image for 162 Anamuli St 21 of 23 Listing Image for 162 Anamuli St 22 of 23 Listing Image for 162 Anamuli St 23 of 23

$1,179,000

Na Hoku at Maui Lani

162 Anamuli St, Kahului

3 Beds 2.5 Baths 2,241 SqFt Residential MLS® # 410454

Days on Market: 38

Pono Real Estate LLC Leslene@ponorealestate.com

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 705 Alulike St Lot 27 1 of 27 Listing Image for 705 Alulike St Lot 27 2 of 27 Listing Image for 705 Alulike St Lot 27 3 of 27 Listing Image for 705 Alulike St Lot 27 4 of 27 Listing Image for 705 Alulike St Lot 27 5 of 27 Listing Image for 705 Alulike St Lot 27 6 of 27 Listing Image for 705 Alulike St Lot 27 7 of 27 Listing Image for 705 Alulike St Lot 27 8 of 27 Listing Image for 705 Alulike St Lot 27 9 of 27 Listing Image for 705 Alulike St Lot 27 10 of 27 Listing Image for 705 Alulike St Lot 27 11 of 27 Listing Image for 705 Alulike St Lot 27 12 of 27 Listing Image for 705 Alulike St Lot 27 13 of 27 Listing Image for 705 Alulike St Lot 27 14 of 27 Listing Image for 705 Alulike St Lot 27 15 of 27 Listing Image for 705 Alulike St Lot 27 16 of 27 Listing Image for 705 Alulike St Lot 27 17 of 27 Listing Image for 705 Alulike St Lot 27 18 of 27 Listing Image for 705 Alulike St Lot 27 19 of 27 Listing Image for 705 Alulike St Lot 27 20 of 27 Listing Image for 705 Alulike St Lot 27 21 of 27 Listing Image for 705 Alulike St Lot 27 22 of 27 Listing Image for 705 Alulike St Lot 27 23 of 27 Listing Image for 705 Alulike St Lot 27 24 of 27 Listing Image for 705 Alulike St Lot 27 25 of 27 Listing Image for 705 Alulike St Lot 27 26 of 27 Listing Image for 705 Alulike St Lot 27 27 of 27

$2,275,000

Kenolio Estates

705 Alulike St Lot 27, Kihei

3 Beds 2 Baths 1,754 SqFt Residential MLS® # 410444

Days on Market: 39

Coldwell Banker Island Prop(S) Cell: 808-463-4644

Short Term Rental
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$4,200,000

Wailea Beach Villas H102

3800 Wailea Alanui Blvd H102, Wailea/Makena

2 Beds 2 Baths 1,899 SqFt Residential MLS® # 410442

Days on Market: 39

Hawaii Life (W) Cell: 808-280-2055

View 6 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: 04/24/2026
101 Maa St Lot 76-a, Kahului

$1,900,000

Maui Lani Village Center Lot 76-A

101 Maa St Lot 76-a, Kahului

0 Beds 0 Baths 0 SqFt Commercial Sale MLS® # 409409 Date Sold: April 24, 2026
Sold
Closed: 06/30/2026
Listing Image for 1911 Pohakea Pl 1 of 31 Listing Image for 1911 Pohakea Pl 2 of 31 Listing Image for 1911 Pohakea Pl 3 of 31 Listing Image for 1911 Pohakea Pl 4 of 31 Listing Image for 1911 Pohakea Pl 5 of 31 Listing Image for 1911 Pohakea Pl 6 of 31 Listing Image for 1911 Pohakea Pl 7 of 31 Listing Image for 1911 Pohakea Pl 8 of 31 Listing Image for 1911 Pohakea Pl 9 of 31 Listing Image for 1911 Pohakea Pl 10 of 31 Listing Image for 1911 Pohakea Pl 11 of 31 Listing Image for 1911 Pohakea Pl 12 of 31 Listing Image for 1911 Pohakea Pl 13 of 31 Listing Image for 1911 Pohakea Pl 14 of 31 Listing Image for 1911 Pohakea Pl 15 of 31 Listing Image for 1911 Pohakea Pl 16 of 31 Listing Image for 1911 Pohakea Pl 17 of 31 Listing Image for 1911 Pohakea Pl 18 of 31 Listing Image for 1911 Pohakea Pl 19 of 31 Listing Image for 1911 Pohakea Pl 20 of 31 Listing Image for 1911 Pohakea Pl 21 of 31 Listing Image for 1911 Pohakea Pl 22 of 31 Listing Image for 1911 Pohakea Pl 23 of 31 Listing Image for 1911 Pohakea Pl 24 of 31 Listing Image for 1911 Pohakea Pl 25 of 31 Listing Image for 1911 Pohakea Pl 26 of 31 Listing Image for 1911 Pohakea Pl 27 of 31 Listing Image for 1911 Pohakea Pl 28 of 31 Listing Image for 1911 Pohakea Pl 29 of 31 Listing Image for 1911 Pohakea Pl 30 of 31 Listing Image for 1911 Pohakea Pl 31 of 31

$1,185,000

Nanea at Kehalani

1911 Pohakea Pl, Wailuku

3 Beds 2.5 Baths 1,713 SqFt Residential MLS® # 409375 Date Sold: June 30, 2026
Sold
Closed: 06/29/2026
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$2,025,000

Hana Agricultural Park

285 Kalo Rd, Hana

3 Beds 3 Baths 3,417 SqFt Residential MLS® # 409355 Date Sold: June 29, 2026
Sold
Closed: 05/28/2026
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$1,395,000

Haiku

85 Nolu Rd, Haiku

3 Beds 2 Baths 1,248 SqFt Residential MLS® # 409353 Date Sold: May 28, 2026
Sold
Closed: 05/14/2026
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$762,500

Kamaole Sands 7-410

2695 S Kihei Rd 7-410, Kihei

2 Beds 2 Baths 1,188 SqFt Residential MLS® # 409352 Date Sold: May 14, 2026
Sold
Closed: 08/25/2026
Listing Image for 3300 Wailea Alanui Dr 17d 1 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 2 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 3 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 4 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 5 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 6 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 7 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 8 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 9 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 10 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 11 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 12 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 13 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 14 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 15 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 16 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 17 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 18 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 19 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 20 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 21 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 22 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 23 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 24 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 25 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 26 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 27 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 28 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 29 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 30 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 31 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 32 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 33 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 34 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 35 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 36 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 37 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 38 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 39 of 40 Listing Image for 3300 Wailea Alanui Dr 17d 40 of 40

$1,450,000

↓ $45,000

Wailea Ekahi 17D

3300 Wailea Alanui Dr 17d, Wailea/Makena

1 Bed 2 Baths 960 SqFt Residential MLS® # 409350 Date Sold: August 25, 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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