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 44 Kanani Rd 3106 1 of 35 Listing Image for 44 Kanani Rd 3106 2 of 35 Listing Image for 44 Kanani Rd 3106 3 of 35 Listing Image for 44 Kanani Rd 3106 4 of 35 Listing Image for 44 Kanani Rd 3106 5 of 35 Listing Image for 44 Kanani Rd 3106 6 of 35 Listing Image for 44 Kanani Rd 3106 7 of 35 Listing Image for 44 Kanani Rd 3106 8 of 35 Listing Image for 44 Kanani Rd 3106 9 of 35 Listing Image for 44 Kanani Rd 3106 10 of 35 Listing Image for 44 Kanani Rd 3106 11 of 35 Listing Image for 44 Kanani Rd 3106 12 of 35 Listing Image for 44 Kanani Rd 3106 13 of 35 Listing Image for 44 Kanani Rd 3106 14 of 35 Listing Image for 44 Kanani Rd 3106 15 of 35 Listing Image for 44 Kanani Rd 3106 16 of 35 Listing Image for 44 Kanani Rd 3106 17 of 35 Listing Image for 44 Kanani Rd 3106 18 of 35 Listing Image for 44 Kanani Rd 3106 19 of 35 Listing Image for 44 Kanani Rd 3106 20 of 35 Listing Image for 44 Kanani Rd 3106 21 of 35 Listing Image for 44 Kanani Rd 3106 22 of 35 Listing Image for 44 Kanani Rd 3106 23 of 35 Listing Image for 44 Kanani Rd 3106 24 of 35 Listing Image for 44 Kanani Rd 3106 25 of 35 Listing Image for 44 Kanani Rd 3106 26 of 35 Listing Image for 44 Kanani Rd 3106 27 of 35 Listing Image for 44 Kanani Rd 3106 28 of 35 Listing Image for 44 Kanani Rd 3106 29 of 35 Listing Image for 44 Kanani Rd 3106 30 of 35 Listing Image for 44 Kanani Rd 3106 31 of 35 Listing Image for 44 Kanani Rd 3106 32 of 35 Listing Image for 44 Kanani Rd 3106 33 of 35 Listing Image for 44 Kanani Rd 3106 34 of 35 Listing Image for 44 Kanani Rd 3106 35 of 35

$850,000

Hale Kanani 3106

44 Kanani Rd 3106, Kihei

3 Beds 2 Baths 1,059 SqFt Residential MLS® # 409518

Days on Market: 134

Coldwell Banker Island Prop(S) Cell: 808-205-6696

Short Term Rental
Listing Image for 3200 Wailea Alanui Dr 1509 1 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 2 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 3 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 4 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 5 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 6 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 7 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 8 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 9 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 10 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 11 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 12 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 13 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 14 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 15 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 16 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 17 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 18 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 19 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 20 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 21 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 22 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 23 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 24 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 25 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 26 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 27 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 28 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 29 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 30 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 31 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 32 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 33 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 34 of 35 Listing Image for 3200 Wailea Alanui Dr 1509 35 of 35

$1,395,000

Palms at Wailea 1509

3200 Wailea Alanui Dr 1509, Wailea/Makena

2 Beds 2 Baths 1,242 SqFt Residential MLS® # 409516

Days on Market: 134

Coldwell Banker Island Prop-Ku Cell: 808-283-2891

Listing Image for 1073 Nanihoku Pl 1 of 50 Listing Image for 1073 Nanihoku Pl 2 of 50 Listing Image for 1073 Nanihoku Pl 3 of 50 Listing Image for 1073 Nanihoku Pl 4 of 50 Listing Image for 1073 Nanihoku Pl 5 of 50 Listing Image for 1073 Nanihoku Pl 6 of 50 Listing Image for 1073 Nanihoku Pl 7 of 50 Listing Image for 1073 Nanihoku Pl 8 of 50 Listing Image for 1073 Nanihoku Pl 9 of 50 Listing Image for 1073 Nanihoku Pl 10 of 50 Listing Image for 1073 Nanihoku Pl 11 of 50 Listing Image for 1073 Nanihoku Pl 12 of 50 Listing Image for 1073 Nanihoku Pl 13 of 50 Listing Image for 1073 Nanihoku Pl 14 of 50 Listing Image for 1073 Nanihoku Pl 15 of 50 Listing Image for 1073 Nanihoku Pl 16 of 50 Listing Image for 1073 Nanihoku Pl 17 of 50 Listing Image for 1073 Nanihoku Pl 18 of 50 Listing Image for 1073 Nanihoku Pl 19 of 50 Listing Image for 1073 Nanihoku Pl 20 of 50 Listing Image for 1073 Nanihoku Pl 21 of 50 Listing Image for 1073 Nanihoku Pl 22 of 50 Listing Image for 1073 Nanihoku Pl 23 of 50 Listing Image for 1073 Nanihoku Pl 24 of 50 Listing Image for 1073 Nanihoku Pl 25 of 50 Listing Image for 1073 Nanihoku Pl 26 of 50 Listing Image for 1073 Nanihoku Pl 27 of 50 Listing Image for 1073 Nanihoku Pl 28 of 50 Listing Image for 1073 Nanihoku Pl 29 of 50 Listing Image for 1073 Nanihoku Pl 30 of 50 Listing Image for 1073 Nanihoku Pl 31 of 50 Listing Image for 1073 Nanihoku Pl 32 of 50 Listing Image for 1073 Nanihoku Pl 33 of 50 Listing Image for 1073 Nanihoku Pl 34 of 50 Listing Image for 1073 Nanihoku Pl 35 of 50 Listing Image for 1073 Nanihoku Pl 36 of 50 Listing Image for 1073 Nanihoku Pl 37 of 50 Listing Image for 1073 Nanihoku Pl 38 of 50 Listing Image for 1073 Nanihoku Pl 39 of 50 Listing Image for 1073 Nanihoku Pl 40 of 50 Listing Image for 1073 Nanihoku Pl 41 of 50 Listing Image for 1073 Nanihoku Pl 42 of 50 Listing Image for 1073 Nanihoku Pl 43 of 50 Listing Image for 1073 Nanihoku Pl 44 of 50 Listing Image for 1073 Nanihoku Pl 45 of 50 Listing Image for 1073 Nanihoku Pl 46 of 50 Listing Image for 1073 Nanihoku Pl 47 of 50 Listing Image for 1073 Nanihoku Pl 48 of 50 Listing Image for 1073 Nanihoku Pl 49 of 50 Listing Image for 1073 Nanihoku Pl 50 of 50

$3,333,000

↓ $62,000

Haiku

1073 Nanihoku Pl, Haiku

7 Beds 4.5 Baths 1,859 SqFt Residential MLS® # 409514

Days on Market: 134

eXp Realty Cell: 808-707-0504

Listing Image for 658 Waiehu Beach Rd 1 of 37 Listing Image for 658 Waiehu Beach Rd 2 of 37 Listing Image for 658 Waiehu Beach Rd 3 of 37 Listing Image for 658 Waiehu Beach Rd 4 of 37 Listing Image for 658 Waiehu Beach Rd 5 of 37 Listing Image for 658 Waiehu Beach Rd 6 of 37 Listing Image for 658 Waiehu Beach Rd 7 of 37 Listing Image for 658 Waiehu Beach Rd 8 of 37 Listing Image for 658 Waiehu Beach Rd 9 of 37 Listing Image for 658 Waiehu Beach Rd 10 of 37 Listing Image for 658 Waiehu Beach Rd 11 of 37 Listing Image for 658 Waiehu Beach Rd 12 of 37 Listing Image for 658 Waiehu Beach Rd 13 of 37 Listing Image for 658 Waiehu Beach Rd 14 of 37 Listing Image for 658 Waiehu Beach Rd 15 of 37 Listing Image for 658 Waiehu Beach Rd 16 of 37 Listing Image for 658 Waiehu Beach Rd 17 of 37 Listing Image for 658 Waiehu Beach Rd 18 of 37 Listing Image for 658 Waiehu Beach Rd 19 of 37 Listing Image for 658 Waiehu Beach Rd 20 of 37 Listing Image for 658 Waiehu Beach Rd 21 of 37 Listing Image for 658 Waiehu Beach Rd 22 of 37 Listing Image for 658 Waiehu Beach Rd 23 of 37 Listing Image for 658 Waiehu Beach Rd 24 of 37 Listing Image for 658 Waiehu Beach Rd 25 of 37 Listing Image for 658 Waiehu Beach Rd 26 of 37 Listing Image for 658 Waiehu Beach Rd 27 of 37 Listing Image for 658 Waiehu Beach Rd 28 of 37 Listing Image for 658 Waiehu Beach Rd 29 of 37 Listing Image for 658 Waiehu Beach Rd 30 of 37 Listing Image for 658 Waiehu Beach Rd 31 of 37 Listing Image for 658 Waiehu Beach Rd 32 of 37 Listing Image for 658 Waiehu Beach Rd 33 of 37 Listing Image for 658 Waiehu Beach Rd 34 of 37 Listing Image for 658 Waiehu Beach Rd 35 of 37 Listing Image for 658 Waiehu Beach Rd 36 of 37 Listing Image for 658 Waiehu Beach Rd 37 of 37

$1,050,000

↓ $150,000

Wailuku

658 Waiehu Beach Rd, Wailuku

3 Beds 1 Bath 1,386 SqFt Residential MLS® # 405845

Days on Market: 501

Sunward Realty Inc

Buying Real Estate on Maui

Buying Real Estate on Maui

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

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Listing Image for 486 Polulani Dr 1 of 30 Listing Image for 486 Polulani Dr 2 of 30 Listing Image for 486 Polulani Dr 3 of 30 Listing Image for 486 Polulani Dr 4 of 30 Listing Image for 486 Polulani Dr 5 of 30 Listing Image for 486 Polulani Dr 6 of 30 Listing Image for 486 Polulani Dr 7 of 30 Listing Image for 486 Polulani Dr 8 of 30 Listing Image for 486 Polulani Dr 9 of 30 Listing Image for 486 Polulani Dr 10 of 30 Listing Image for 486 Polulani Dr 11 of 30 Listing Image for 486 Polulani Dr 12 of 30 Listing Image for 486 Polulani Dr 13 of 30 Listing Image for 486 Polulani Dr 14 of 30 Listing Image for 486 Polulani Dr 15 of 30 Listing Image for 486 Polulani Dr 16 of 30 Listing Image for 486 Polulani Dr 17 of 30 Listing Image for 486 Polulani Dr 18 of 30 Listing Image for 486 Polulani Dr 19 of 30 Listing Image for 486 Polulani Dr 20 of 30 Listing Image for 486 Polulani Dr 21 of 30 Listing Image for 486 Polulani Dr 22 of 30 Listing Image for 486 Polulani Dr 23 of 30 Listing Image for 486 Polulani Dr 24 of 30 Listing Image for 486 Polulani Dr 25 of 30 Listing Image for 486 Polulani Dr 26 of 30 Listing Image for 486 Polulani Dr 27 of 30 Listing Image for 486 Polulani Dr 28 of 30 Listing Image for 486 Polulani Dr 29 of 30 Listing Image for 486 Polulani Dr 30 of 30

$1,398,000

Wailuku Heights

486 Polulani Dr, Wailuku

3 Beds 2.5 Baths 1,802 SqFt Residential MLS® # 409509

Days on Market: 134

Berkshire Hathaway HI Isl Prop

Short Term Rental
Listing Image for 3543 Lower Honoapiilani Rd F406 1 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 2 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 3 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 4 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 5 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 6 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 7 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 8 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 9 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 10 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 11 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 12 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 13 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 14 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 15 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 16 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 17 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 18 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 19 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 20 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 21 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 22 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 23 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 24 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 25 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 26 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 27 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 28 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 29 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 30 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 31 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 32 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 33 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 34 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 35 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 36 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 37 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 38 of 39 Listing Image for 3543 Lower Honoapiilani Rd F406 39 of 39

$1,345,000

Papakea Resort F406

3543 Lower Honoapiilani Rd F406, Napili/Kahana/Honokowai

3 Beds 3 Baths 1,127 SqFt Residential MLS® # 409508

Days on Market: 135

Maui Rentals and Realty LLC

In Escrow
Listing Image for 79 Kaniela St 1 of 7 Listing Image for 79 Kaniela St 2 of 7 Listing Image for 79 Kaniela St 3 of 7 Listing Image for 79 Kaniela St 4 of 7 Listing Image for 79 Kaniela St 5 of 7 Listing Image for 79 Kaniela St 6 of 7 Listing Image for 79 Kaniela St 7 of 7

$950,000

Wailuku

79 Kaniela St, Wailuku

4 Beds 3 Baths 1,684 SqFt Residential MLS® # 409507

Days on Market: 137

Agency Rental

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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.

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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