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 145 S Holokai Rd 1 of 50 Listing Image for 145 S Holokai Rd 2 of 50 Listing Image for 145 S Holokai Rd 3 of 50 Listing Image for 145 S Holokai Rd 4 of 50 Listing Image for 145 S Holokai Rd 5 of 50 Listing Image for 145 S Holokai Rd 6 of 50 Listing Image for 145 S Holokai Rd 7 of 50 Listing Image for 145 S Holokai Rd 8 of 50 Listing Image for 145 S Holokai Rd 9 of 50 Listing Image for 145 S Holokai Rd 10 of 50 Listing Image for 145 S Holokai Rd 11 of 50 Listing Image for 145 S Holokai Rd 12 of 50 Listing Image for 145 S Holokai Rd 13 of 50 Listing Image for 145 S Holokai Rd 14 of 50 Listing Image for 145 S Holokai Rd 15 of 50 Listing Image for 145 S Holokai Rd 16 of 50 Listing Image for 145 S Holokai Rd 17 of 50 Listing Image for 145 S Holokai Rd 18 of 50 Listing Image for 145 S Holokai Rd 19 of 50 Listing Image for 145 S Holokai Rd 20 of 50 Listing Image for 145 S Holokai Rd 21 of 50 Listing Image for 145 S Holokai Rd 22 of 50 Listing Image for 145 S Holokai Rd 23 of 50 Listing Image for 145 S Holokai Rd 24 of 50 Listing Image for 145 S Holokai Rd 25 of 50 Listing Image for 145 S Holokai Rd 26 of 50 Listing Image for 145 S Holokai Rd 27 of 50 Listing Image for 145 S Holokai Rd 28 of 50 Listing Image for 145 S Holokai Rd 29 of 50 Listing Image for 145 S Holokai Rd 30 of 50 Listing Image for 145 S Holokai Rd 31 of 50 Listing Image for 145 S Holokai Rd 32 of 50 Listing Image for 145 S Holokai Rd 33 of 50 Listing Image for 145 S Holokai Rd 34 of 50 Listing Image for 145 S Holokai Rd 35 of 50 Listing Image for 145 S Holokai Rd 36 of 50 Listing Image for 145 S Holokai Rd 37 of 50 Listing Image for 145 S Holokai Rd 38 of 50 Listing Image for 145 S Holokai Rd 39 of 50 Listing Image for 145 S Holokai Rd 40 of 50 Listing Image for 145 S Holokai Rd 41 of 50 Listing Image for 145 S Holokai Rd 42 of 50 Listing Image for 145 S Holokai Rd 43 of 50 Listing Image for 145 S Holokai Rd 44 of 50 Listing Image for 145 S Holokai Rd 45 of 50 Listing Image for 145 S Holokai Rd 46 of 50 Listing Image for 145 S Holokai Rd 47 of 50 Listing Image for 145 S Holokai Rd 48 of 50 Listing Image for 145 S Holokai Rd 49 of 50 Listing Image for 145 S Holokai Rd 50 of 50

$1,250,000

↓ $175,000

Haiku

145 S Holokai Rd, Haiku

3 Beds 3 Baths 1,648 SqFt Residential MLS® # 409390

Days on Market: 144

REMAX Hawaii Maui

Listing Image for 137 Holomoana Way 4a 1 of 50 Listing Image for 137 Holomoana Way 4a 2 of 50 Listing Image for 137 Holomoana Way 4a 3 of 50 Listing Image for 137 Holomoana Way 4a 4 of 50 Listing Image for 137 Holomoana Way 4a 5 of 50 Listing Image for 137 Holomoana Way 4a 6 of 50 Listing Image for 137 Holomoana Way 4a 7 of 50 Listing Image for 137 Holomoana Way 4a 8 of 50 Listing Image for 137 Holomoana Way 4a 9 of 50 Listing Image for 137 Holomoana Way 4a 10 of 50 Listing Image for 137 Holomoana Way 4a 11 of 50 Listing Image for 137 Holomoana Way 4a 12 of 50 Listing Image for 137 Holomoana Way 4a 13 of 50 Listing Image for 137 Holomoana Way 4a 14 of 50 Listing Image for 137 Holomoana Way 4a 15 of 50 Listing Image for 137 Holomoana Way 4a 16 of 50 Listing Image for 137 Holomoana Way 4a 17 of 50 Listing Image for 137 Holomoana Way 4a 18 of 50 Listing Image for 137 Holomoana Way 4a 19 of 50 Listing Image for 137 Holomoana Way 4a 20 of 50 Listing Image for 137 Holomoana Way 4a 21 of 50 Listing Image for 137 Holomoana Way 4a 22 of 50 Listing Image for 137 Holomoana Way 4a 23 of 50 Listing Image for 137 Holomoana Way 4a 24 of 50 Listing Image for 137 Holomoana Way 4a 25 of 50 Listing Image for 137 Holomoana Way 4a 26 of 50 Listing Image for 137 Holomoana Way 4a 27 of 50 Listing Image for 137 Holomoana Way 4a 28 of 50 Listing Image for 137 Holomoana Way 4a 29 of 50 Listing Image for 137 Holomoana Way 4a 30 of 50 Listing Image for 137 Holomoana Way 4a 31 of 50 Listing Image for 137 Holomoana Way 4a 32 of 50 Listing Image for 137 Holomoana Way 4a 33 of 50 Listing Image for 137 Holomoana Way 4a 34 of 50 Listing Image for 137 Holomoana Way 4a 35 of 50 Listing Image for 137 Holomoana Way 4a 36 of 50 Listing Image for 137 Holomoana Way 4a 37 of 50 Listing Image for 137 Holomoana Way 4a 38 of 50 Listing Image for 137 Holomoana Way 4a 39 of 50 Listing Image for 137 Holomoana Way 4a 40 of 50 Listing Image for 137 Holomoana Way 4a 41 of 50 Listing Image for 137 Holomoana Way 4a 42 of 50 Listing Image for 137 Holomoana Way 4a 43 of 50 Listing Image for 137 Holomoana Way 4a 44 of 50 Listing Image for 137 Holomoana Way 4a 45 of 50 Listing Image for 137 Holomoana Way 4a 46 of 50 Listing Image for 137 Holomoana Way 4a 47 of 50 Listing Image for 137 Holomoana Way 4a 48 of 50 Listing Image for 137 Holomoana Way 4a 49 of 50 Listing Image for 137 Holomoana Way 4a 50 of 50

$2,900,000

Makalii at Wailea 4A

137 Holomoana Way 4a, Wailea/Makena

3 Beds 3 Baths 1,574 SqFt Residential MLS® # 409389

Days on Market: 144

Island Sotheby's International Realty(W) Cell: 808-283-7965

In Escrow
Listing Image for 579 Kuanana St 1 of 34 Listing Image for 579 Kuanana St 2 of 34 Listing Image for 579 Kuanana St 3 of 34 Listing Image for 579 Kuanana St 4 of 34 Listing Image for 579 Kuanana St 5 of 34 Listing Image for 579 Kuanana St 6 of 34 Listing Image for 579 Kuanana St 7 of 34 Listing Image for 579 Kuanana St 8 of 34 Listing Image for 579 Kuanana St 9 of 34 Listing Image for 579 Kuanana St 10 of 34 Listing Image for 579 Kuanana St 11 of 34 Listing Image for 579 Kuanana St 12 of 34 Listing Image for 579 Kuanana St 13 of 34 Listing Image for 579 Kuanana St 14 of 34 Listing Image for 579 Kuanana St 15 of 34 Listing Image for 579 Kuanana St 16 of 34 Listing Image for 579 Kuanana St 17 of 34 Listing Image for 579 Kuanana St 18 of 34 Listing Image for 579 Kuanana St 19 of 34 Listing Image for 579 Kuanana St 20 of 34 Listing Image for 579 Kuanana St 21 of 34 Listing Image for 579 Kuanana St 22 of 34 Listing Image for 579 Kuanana St 23 of 34 Listing Image for 579 Kuanana St 24 of 34 Listing Image for 579 Kuanana St 25 of 34 Listing Image for 579 Kuanana St 26 of 34 Listing Image for 579 Kuanana St 27 of 34 Listing Image for 579 Kuanana St 28 of 34 Listing Image for 579 Kuanana St 29 of 34 Listing Image for 579 Kuanana St 30 of 34 Listing Image for 579 Kuanana St 31 of 34 Listing Image for 579 Kuanana St 32 of 34 Listing Image for 579 Kuanana St 33 of 34 Listing Image for 579 Kuanana St 34 of 34

$872,000

Skill Village

579 Kuanana St, Spreckelsville/Paia/Kuau

3 Beds 1 Bath 1,608 SqFt Residential MLS® # 409379

Days on Market: 147

Coldwell Banker Island Prop(S) Cell: 808-280-8118

Short Term Rental
Listing Image for 150 Puukolii Rd 36 1 of 31 Listing Image for 150 Puukolii Rd 36 2 of 31 Listing Image for 150 Puukolii Rd 36 3 of 31 Listing Image for 150 Puukolii Rd 36 4 of 31 Listing Image for 150 Puukolii Rd 36 5 of 31 Listing Image for 150 Puukolii Rd 36 6 of 31 Listing Image for 150 Puukolii Rd 36 7 of 31 Listing Image for 150 Puukolii Rd 36 8 of 31 Listing Image for 150 Puukolii Rd 36 9 of 31 Listing Image for 150 Puukolii Rd 36 10 of 31 Listing Image for 150 Puukolii Rd 36 11 of 31 Listing Image for 150 Puukolii Rd 36 12 of 31 Listing Image for 150 Puukolii Rd 36 13 of 31 Listing Image for 150 Puukolii Rd 36 14 of 31 Listing Image for 150 Puukolii Rd 36 15 of 31 Listing Image for 150 Puukolii Rd 36 16 of 31 Listing Image for 150 Puukolii Rd 36 17 of 31 Listing Image for 150 Puukolii Rd 36 18 of 31 Listing Image for 150 Puukolii Rd 36 19 of 31 Listing Image for 150 Puukolii Rd 36 20 of 31 Listing Image for 150 Puukolii Rd 36 21 of 31 Listing Image for 150 Puukolii Rd 36 22 of 31 Listing Image for 150 Puukolii Rd 36 23 of 31 Listing Image for 150 Puukolii Rd 36 24 of 31 Listing Image for 150 Puukolii Rd 36 25 of 31 Listing Image for 150 Puukolii Rd 36 26 of 31 Listing Image for 150 Puukolii Rd 36 27 of 31 Listing Image for 150 Puukolii Rd 36 28 of 31 Listing Image for 150 Puukolii Rd 36 29 of 31 Listing Image for 150 Puukolii Rd 36 30 of 31 Listing Image for 150 Puukolii Rd 36 31 of 31

$1,349,500

Kaanapali Plantation 36

150 Puukolii Rd 36, Kaanapali

2 Beds 2 Baths 1,152 SqFt Residential MLS® # 406133

Days on Market: 471

Berkshire Hathaway Maui Prop-L Cell: 808-280-7061

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 544 Iiwi Way 1 of 50 Listing Image for 544 Iiwi Way 2 of 50 Listing Image for 544 Iiwi Way 3 of 50 Listing Image for 544 Iiwi Way 4 of 50 Listing Image for 544 Iiwi Way 5 of 50 Listing Image for 544 Iiwi Way 6 of 50 Listing Image for 544 Iiwi Way 7 of 50 Listing Image for 544 Iiwi Way 8 of 50 Listing Image for 544 Iiwi Way 9 of 50 Listing Image for 544 Iiwi Way 10 of 50 Listing Image for 544 Iiwi Way 11 of 50 Listing Image for 544 Iiwi Way 12 of 50 Listing Image for 544 Iiwi Way 13 of 50 Listing Image for 544 Iiwi Way 14 of 50 Listing Image for 544 Iiwi Way 15 of 50 Listing Image for 544 Iiwi Way 16 of 50 Listing Image for 544 Iiwi Way 17 of 50 Listing Image for 544 Iiwi Way 18 of 50 Listing Image for 544 Iiwi Way 19 of 50 Listing Image for 544 Iiwi Way 20 of 50 Listing Image for 544 Iiwi Way 21 of 50 Listing Image for 544 Iiwi Way 22 of 50 Listing Image for 544 Iiwi Way 23 of 50 Listing Image for 544 Iiwi Way 24 of 50 Listing Image for 544 Iiwi Way 25 of 50 Listing Image for 544 Iiwi Way 26 of 50 Listing Image for 544 Iiwi Way 27 of 50 Listing Image for 544 Iiwi Way 28 of 50 Listing Image for 544 Iiwi Way 29 of 50 Listing Image for 544 Iiwi Way 30 of 50 Listing Image for 544 Iiwi Way 31 of 50 Listing Image for 544 Iiwi Way 32 of 50 Listing Image for 544 Iiwi Way 33 of 50 Listing Image for 544 Iiwi Way 34 of 50 Listing Image for 544 Iiwi Way 35 of 50 Listing Image for 544 Iiwi Way 36 of 50 Listing Image for 544 Iiwi Way 37 of 50 Listing Image for 544 Iiwi Way 38 of 50 Listing Image for 544 Iiwi Way 39 of 50 Listing Image for 544 Iiwi Way 40 of 50 Listing Image for 544 Iiwi Way 41 of 50 Listing Image for 544 Iiwi Way 42 of 50 Listing Image for 544 Iiwi Way 43 of 50 Listing Image for 544 Iiwi Way 44 of 50 Listing Image for 544 Iiwi Way 45 of 50 Listing Image for 544 Iiwi Way 46 of 50 Listing Image for 544 Iiwi Way 47 of 50 Listing Image for 544 Iiwi Way 48 of 50 Listing Image for 544 Iiwi Way 49 of 50 Listing Image for 544 Iiwi Way 50 of 50

$2,390,000

↓ $100,000

Wailuku Heights

544 Iiwi Way, Wailuku

4 Beds 3 Baths 3,696 SqFt Residential MLS® # 409373

Days on Market: 146

Keller Williams Realty Maui-Ka Cell: 808-673-8138

Listing Image for 371 Lono Ave 1 of 11 Listing Image for 371 Lono Ave 2 of 11 Listing Image for 371 Lono Ave 3 of 11 Listing Image for 371 Lono Ave 4 of 11 Listing Image for 371 Lono Ave 5 of 11 Listing Image for 371 Lono Ave 6 of 11 Listing Image for 371 Lono Ave 7 of 11 Listing Image for 371 Lono Ave 8 of 11 Listing Image for 371 Lono Ave 9 of 11 Listing Image for 371 Lono Ave 10 of 11 Listing Image for 371 Lono Ave 11 of 11

$1,950,000

↓ $250,000

Kahului

371 Lono Ave, Kahului

3 Beds 2 Baths 1,057 SqFt Residential MLS® # 409369

Days on Market: 147

Big Wave Realty LLC

Listing Image for 505 Hoohalahala St 1 of 50 Listing Image for 505 Hoohalahala St 2 of 50 Listing Image for 505 Hoohalahala St 3 of 50 Listing Image for 505 Hoohalahala St 4 of 50 Listing Image for 505 Hoohalahala St 5 of 50 Listing Image for 505 Hoohalahala St 6 of 50 Listing Image for 505 Hoohalahala St 7 of 50 Listing Image for 505 Hoohalahala St 8 of 50 Listing Image for 505 Hoohalahala St 9 of 50 Listing Image for 505 Hoohalahala St 10 of 50 Listing Image for 505 Hoohalahala St 11 of 50 Listing Image for 505 Hoohalahala St 12 of 50 Listing Image for 505 Hoohalahala St 13 of 50 Listing Image for 505 Hoohalahala St 14 of 50 Listing Image for 505 Hoohalahala St 15 of 50 Listing Image for 505 Hoohalahala St 16 of 50 Listing Image for 505 Hoohalahala St 17 of 50 Listing Image for 505 Hoohalahala St 18 of 50 Listing Image for 505 Hoohalahala St 19 of 50 Listing Image for 505 Hoohalahala St 20 of 50 Listing Image for 505 Hoohalahala St 21 of 50 Listing Image for 505 Hoohalahala St 22 of 50 Listing Image for 505 Hoohalahala St 23 of 50 Listing Image for 505 Hoohalahala St 24 of 50 Listing Image for 505 Hoohalahala St 25 of 50 Listing Image for 505 Hoohalahala St 26 of 50 Listing Image for 505 Hoohalahala St 27 of 50 Listing Image for 505 Hoohalahala St 28 of 50 Listing Image for 505 Hoohalahala St 29 of 50 Listing Image for 505 Hoohalahala St 30 of 50 Listing Image for 505 Hoohalahala St 31 of 50 Listing Image for 505 Hoohalahala St 32 of 50 Listing Image for 505 Hoohalahala St 33 of 50 Listing Image for 505 Hoohalahala St 34 of 50 Listing Image for 505 Hoohalahala St 35 of 50 Listing Image for 505 Hoohalahala St 36 of 50 Listing Image for 505 Hoohalahala St 37 of 50 Listing Image for 505 Hoohalahala St 38 of 50 Listing Image for 505 Hoohalahala St 39 of 50 Listing Image for 505 Hoohalahala St 40 of 50 Listing Image for 505 Hoohalahala St 41 of 50 Listing Image for 505 Hoohalahala St 42 of 50 Listing Image for 505 Hoohalahala St 43 of 50 Listing Image for 505 Hoohalahala St 44 of 50 Listing Image for 505 Hoohalahala St 45 of 50 Listing Image for 505 Hoohalahala St 46 of 50 Listing Image for 505 Hoohalahala St 47 of 50 Listing Image for 505 Hoohalahala St 48 of 50 Listing Image for 505 Hoohalahala St 49 of 50 Listing Image for 505 Hoohalahala St 50 of 50

$1,999,000

Maui Meadows

505 Hoohalahala St, Maui Meadows

3 Beds 2 Baths 1,585 SqFt Residential MLS® # 409237

Days on Market: 160

Coldwell Banker Island Prop(S) Cell: 808-870-4899

View 7 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.

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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