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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Short Term Rental
Listing Image for 3445 Lower Honoapiilani Rd 435 1 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 2 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 3 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 4 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 5 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 6 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 7 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 8 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 9 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 10 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 11 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 12 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 13 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 14 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 15 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 16 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 17 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 18 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 19 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 20 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 21 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 22 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 23 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 24 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 25 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 26 of 27 Listing Image for 3445 Lower Honoapiilani Rd 435 27 of 27

$1,270,000

Kaanapali Shores 435

3445 Lower Honoapiilani Rd 435, Kaanapali

2 Beds 2 Baths 964 SqFt Residential MLS® # 407283

Days on Market: 351

Coldwell Banker Island Prop-KP Cell: 808-344-2677

Listing Image for 124 Hoolaau St 138 1 of 34 Listing Image for 124 Hoolaau St 138 2 of 34 Listing Image for 124 Hoolaau St 138 3 of 34 Listing Image for 124 Hoolaau St 138 4 of 34 Listing Image for 124 Hoolaau St 138 5 of 34 Listing Image for 124 Hoolaau St 138 6 of 34 Listing Image for 124 Hoolaau St 138 7 of 34 Listing Image for 124 Hoolaau St 138 8 of 34 Listing Image for 124 Hoolaau St 138 9 of 34 Listing Image for 124 Hoolaau St 138 10 of 34 Listing Image for 124 Hoolaau St 138 11 of 34 Listing Image for 124 Hoolaau St 138 12 of 34 Listing Image for 124 Hoolaau St 138 13 of 34 Listing Image for 124 Hoolaau St 138 14 of 34 Listing Image for 124 Hoolaau St 138 15 of 34 Listing Image for 124 Hoolaau St 138 16 of 34 Listing Image for 124 Hoolaau St 138 17 of 34 Listing Image for 124 Hoolaau St 138 18 of 34 Listing Image for 124 Hoolaau St 138 19 of 34 Listing Image for 124 Hoolaau St 138 20 of 34 Listing Image for 124 Hoolaau St 138 21 of 34 Listing Image for 124 Hoolaau St 138 22 of 34 Listing Image for 124 Hoolaau St 138 23 of 34 Listing Image for 124 Hoolaau St 138 24 of 34 Listing Image for 124 Hoolaau St 138 25 of 34 Listing Image for 124 Hoolaau St 138 26 of 34 Listing Image for 124 Hoolaau St 138 27 of 34 Listing Image for 124 Hoolaau St 138 28 of 34 Listing Image for 124 Hoolaau St 138 29 of 34 Listing Image for 124 Hoolaau St 138 30 of 34 Listing Image for 124 Hoolaau St 138 31 of 34 Listing Image for 124 Hoolaau St 138 32 of 34 Listing Image for 124 Hoolaau St 138 33 of 34 Listing Image for 124 Hoolaau St 138 34 of 34

$879,000

↑ $14,000

Kamani at Kehalani 138

124 Hoolaau St 138, Wailuku

3 Beds 2.5 Baths 1,465 SqFt Residential MLS® # 407263

Days on Market: 352

Aesthetic Real Estate LLC

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$3,950,000

Montage Residences Kapalua Bay 2202

1 Bay Dr 2202, Kapalua

3 Beds 3.5 Baths 2,904 SqFt Residential MLS® # 407262

Days on Market: 353

Compass Cell: 808-276-6881

Listing Image for 172 Huahua Pl Unit A 1 of 11 Listing Image for 172 Huahua Pl Unit A 2 of 11 Listing Image for 172 Huahua Pl Unit A 3 of 11 Listing Image for 172 Huahua Pl Unit A 4 of 11 Listing Image for 172 Huahua Pl Unit A 5 of 11 Listing Image for 172 Huahua Pl Unit A 6 of 11 Listing Image for 172 Huahua Pl Unit A 7 of 11 Listing Image for 172 Huahua Pl Unit A 8 of 11 Listing Image for 172 Huahua Pl Unit A 9 of 11 Listing Image for 172 Huahua Pl Unit A 10 of 11 Listing Image for 172 Huahua Pl Unit A 11 of 11

$3,650,000

↓ $700,000

Kula I'o

172 Huahua Pl Unit A, Kula/Ulupalakua/Kanaio

4 Beds 4 Baths 3,893 SqFt Residential MLS® # 407233

Days on Market: 357

Big Wave Realty LLC

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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Short Term Rental
Listing Image for 106 Kaanapali Shores Pl 804 1 of 31 Listing Image for 106 Kaanapali Shores Pl 804 2 of 31 Listing Image for 106 Kaanapali Shores Pl 804 3 of 31 Listing Image for 106 Kaanapali Shores Pl 804 4 of 31 Listing Image for 106 Kaanapali Shores Pl 804 5 of 31 Listing Image for 106 Kaanapali Shores Pl 804 6 of 31 Listing Image for 106 Kaanapali Shores Pl 804 7 of 31 Listing Image for 106 Kaanapali Shores Pl 804 8 of 31 Listing Image for 106 Kaanapali Shores Pl 804 9 of 31 Listing Image for 106 Kaanapali Shores Pl 804 10 of 31 Listing Image for 106 Kaanapali Shores Pl 804 11 of 31 Listing Image for 106 Kaanapali Shores Pl 804 12 of 31 Listing Image for 106 Kaanapali Shores Pl 804 13 of 31 Listing Image for 106 Kaanapali Shores Pl 804 14 of 31 Listing Image for 106 Kaanapali Shores Pl 804 15 of 31 Listing Image for 106 Kaanapali Shores Pl 804 16 of 31 Listing Image for 106 Kaanapali Shores Pl 804 17 of 31 Listing Image for 106 Kaanapali Shores Pl 804 18 of 31 Listing Image for 106 Kaanapali Shores Pl 804 19 of 31 Listing Image for 106 Kaanapali Shores Pl 804 20 of 31 Listing Image for 106 Kaanapali Shores Pl 804 21 of 31 Listing Image for 106 Kaanapali Shores Pl 804 22 of 31 Listing Image for 106 Kaanapali Shores Pl 804 23 of 31 Listing Image for 106 Kaanapali Shores Pl 804 24 of 31 Listing Image for 106 Kaanapali Shores Pl 804 25 of 31 Listing Image for 106 Kaanapali Shores Pl 804 26 of 31 Listing Image for 106 Kaanapali Shores Pl 804 27 of 31 Listing Image for 106 Kaanapali Shores Pl 804 28 of 31 Listing Image for 106 Kaanapali Shores Pl 804 29 of 31 Listing Image for 106 Kaanapali Shores Pl 804 30 of 31 Listing Image for 106 Kaanapali Shores Pl 804 31 of 31

$925,000

Maui Kai 804

106 Kaanapali Shores Pl 804, Kaanapali

1 Bed 1 Bath 587 SqFt Residential MLS® # 407225

Days on Market: 358

Epic Realty LLC

Short Term Rental
Listing Image for 2385 S Kihei Rd 604 1 of 37 Listing Image for 2385 S Kihei Rd 604 2 of 37 Listing Image for 2385 S Kihei Rd 604 3 of 37 Listing Image for 2385 S Kihei Rd 604 4 of 37 Listing Image for 2385 S Kihei Rd 604 5 of 37 Listing Image for 2385 S Kihei Rd 604 6 of 37 Listing Image for 2385 S Kihei Rd 604 7 of 37 Listing Image for 2385 S Kihei Rd 604 8 of 37 Listing Image for 2385 S Kihei Rd 604 9 of 37 Listing Image for 2385 S Kihei Rd 604 10 of 37 Listing Image for 2385 S Kihei Rd 604 11 of 37 Listing Image for 2385 S Kihei Rd 604 12 of 37 Listing Image for 2385 S Kihei Rd 604 13 of 37 Listing Image for 2385 S Kihei Rd 604 14 of 37 Listing Image for 2385 S Kihei Rd 604 15 of 37 Listing Image for 2385 S Kihei Rd 604 16 of 37 Listing Image for 2385 S Kihei Rd 604 17 of 37 Listing Image for 2385 S Kihei Rd 604 18 of 37 Listing Image for 2385 S Kihei Rd 604 19 of 37 Listing Image for 2385 S Kihei Rd 604 20 of 37 Listing Image for 2385 S Kihei Rd 604 21 of 37 Listing Image for 2385 S Kihei Rd 604 22 of 37 Listing Image for 2385 S Kihei Rd 604 23 of 37 Listing Image for 2385 S Kihei Rd 604 24 of 37 Listing Image for 2385 S Kihei Rd 604 25 of 37 Listing Image for 2385 S Kihei Rd 604 26 of 37 Listing Image for 2385 S Kihei Rd 604 27 of 37 Listing Image for 2385 S Kihei Rd 604 28 of 37 Listing Image for 2385 S Kihei Rd 604 29 of 37 Listing Image for 2385 S Kihei Rd 604 30 of 37 Listing Image for 2385 S Kihei Rd 604 31 of 37 Listing Image for 2385 S Kihei Rd 604 32 of 37 Listing Image for 2385 S Kihei Rd 604 33 of 37 Listing Image for 2385 S Kihei Rd 604 34 of 37 Listing Image for 2385 S Kihei Rd 604 35 of 37 Listing Image for 2385 S Kihei Rd 604 36 of 37 Listing Image for 2385 S Kihei Rd 604 37 of 37

$899,000

↓ $48,000

Kamaole Beach Royale 604

2385 S Kihei Rd 604, Kihei

1 Bed 1 Bath 580 SqFt Residential MLS® # 407218

Days on Market: 360

Coldwell Banker Island Prop(S) Cell: 808-283-7426

Listing Image for 10 Heather Ln 231 1 of 44 Listing Image for 10 Heather Ln 231 2 of 44 Listing Image for 10 Heather Ln 231 3 of 44 Listing Image for 10 Heather Ln 231 4 of 44 Listing Image for 10 Heather Ln 231 5 of 44 Listing Image for 10 Heather Ln 231 6 of 44 Listing Image for 10 Heather Ln 231 7 of 44 Listing Image for 10 Heather Ln 231 8 of 44 Listing Image for 10 Heather Ln 231 9 of 44 Listing Image for 10 Heather Ln 231 10 of 44 Listing Image for 10 Heather Ln 231 11 of 44 Listing Image for 10 Heather Ln 231 12 of 44 Listing Image for 10 Heather Ln 231 13 of 44 Listing Image for 10 Heather Ln 231 14 of 44 Listing Image for 10 Heather Ln 231 15 of 44 Listing Image for 10 Heather Ln 231 16 of 44 Listing Image for 10 Heather Ln 231 17 of 44 Listing Image for 10 Heather Ln 231 18 of 44 Listing Image for 10 Heather Ln 231 19 of 44 Listing Image for 10 Heather Ln 231 20 of 44 Listing Image for 10 Heather Ln 231 21 of 44 Listing Image for 10 Heather Ln 231 22 of 44 Listing Image for 10 Heather Ln 231 23 of 44 Listing Image for 10 Heather Ln 231 24 of 44 Listing Image for 10 Heather Ln 231 25 of 44 Listing Image for 10 Heather Ln 231 26 of 44 Listing Image for 10 Heather Ln 231 27 of 44 Listing Image for 10 Heather Ln 231 28 of 44 Listing Image for 10 Heather Ln 231 29 of 44 Listing Image for 10 Heather Ln 231 30 of 44 Listing Image for 10 Heather Ln 231 31 of 44 Listing Image for 10 Heather Ln 231 32 of 44 Listing Image for 10 Heather Ln 231 33 of 44 Listing Image for 10 Heather Ln 231 34 of 44 Listing Image for 10 Heather Ln 231 35 of 44 Listing Image for 10 Heather Ln 231 36 of 44 Listing Image for 10 Heather Ln 231 37 of 44 Listing Image for 10 Heather Ln 231 38 of 44 Listing Image for 10 Heather Ln 231 39 of 44 Listing Image for 10 Heather Ln 231 40 of 44 Listing Image for 10 Heather Ln 231 41 of 44 Listing Image for 10 Heather Ln 231 42 of 44 Listing Image for 10 Heather Ln 231 43 of 44 Listing Image for 10 Heather Ln 231 44 of 44

$950,000

Villas at Kahana Ridge 231

10 Heather Ln 231, Napili/Kahana/Honokowai

3 Beds 2 Baths 1,174 SqFt Residential MLS® # 407209

Days on Market: 360

Compass Cell: 808-357-8398

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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