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

$2,995,000

↓ $105,000

Alaeloa

20 Hui I Rd, Napili/Kahana/Honokowai

4 Beds 4 Baths 4,000 SqFt Residential MLS® # 408905

Days on Market: 198

Coldwell Banker Island Prop(S) Cell: 808-344-4363

Listing Image for 15 Awela Circle 103 1 of 37 Listing Image for 15 Awela Circle 103 2 of 37 Listing Image for 15 Awela Circle 103 3 of 37 Listing Image for 15 Awela Circle 103 4 of 37 Listing Image for 15 Awela Circle 103 5 of 37 Listing Image for 15 Awela Circle 103 6 of 37 Listing Image for 15 Awela Circle 103 7 of 37 Listing Image for 15 Awela Circle 103 8 of 37 Listing Image for 15 Awela Circle 103 9 of 37 Listing Image for 15 Awela Circle 103 10 of 37 Listing Image for 15 Awela Circle 103 11 of 37 Listing Image for 15 Awela Circle 103 12 of 37 Listing Image for 15 Awela Circle 103 13 of 37 Listing Image for 15 Awela Circle 103 14 of 37 Listing Image for 15 Awela Circle 103 15 of 37 Listing Image for 15 Awela Circle 103 16 of 37 Listing Image for 15 Awela Circle 103 17 of 37 Listing Image for 15 Awela Circle 103 18 of 37 Listing Image for 15 Awela Circle 103 19 of 37 Listing Image for 15 Awela Circle 103 20 of 37 Listing Image for 15 Awela Circle 103 21 of 37 Listing Image for 15 Awela Circle 103 22 of 37 Listing Image for 15 Awela Circle 103 23 of 37 Listing Image for 15 Awela Circle 103 24 of 37 Listing Image for 15 Awela Circle 103 25 of 37 Listing Image for 15 Awela Circle 103 26 of 37 Listing Image for 15 Awela Circle 103 27 of 37 Listing Image for 15 Awela Circle 103 28 of 37 Listing Image for 15 Awela Circle 103 29 of 37 Listing Image for 15 Awela Circle 103 30 of 37 Listing Image for 15 Awela Circle 103 31 of 37 Listing Image for 15 Awela Circle 103 32 of 37 Listing Image for 15 Awela Circle 103 33 of 37 Listing Image for 15 Awela Circle 103 34 of 37 Listing Image for 15 Awela Circle 103 35 of 37 Listing Image for 15 Awela Circle 103 36 of 37 Listing Image for 15 Awela Circle 103 37 of 37

$1,094,000

Villas at Kehalani 103

15 Awela Circle 103, Wailuku

2 Beds 2.5 Baths 1,446 SqFt Residential MLS® # 408902

Days on Market: 198

Maui Real Estate Advisors LLC 808-875-4444

Listing Image for 14 Leanihi Ln B204 1 of 38 Listing Image for 14 Leanihi Ln B204 2 of 38 Listing Image for 14 Leanihi Ln B204 3 of 38 Listing Image for 14 Leanihi Ln B204 4 of 38 Listing Image for 14 Leanihi Ln B204 5 of 38 Listing Image for 14 Leanihi Ln B204 6 of 38 Listing Image for 14 Leanihi Ln B204 7 of 38 Listing Image for 14 Leanihi Ln B204 8 of 38 Listing Image for 14 Leanihi Ln B204 9 of 38 Listing Image for 14 Leanihi Ln B204 10 of 38 Listing Image for 14 Leanihi Ln B204 11 of 38 Listing Image for 14 Leanihi Ln B204 12 of 38 Listing Image for 14 Leanihi Ln B204 13 of 38 Listing Image for 14 Leanihi Ln B204 14 of 38 Listing Image for 14 Leanihi Ln B204 15 of 38 Listing Image for 14 Leanihi Ln B204 16 of 38 Listing Image for 14 Leanihi Ln B204 17 of 38 Listing Image for 14 Leanihi Ln B204 18 of 38 Listing Image for 14 Leanihi Ln B204 19 of 38 Listing Image for 14 Leanihi Ln B204 20 of 38 Listing Image for 14 Leanihi Ln B204 21 of 38 Listing Image for 14 Leanihi Ln B204 22 of 38 Listing Image for 14 Leanihi Ln B204 23 of 38 Listing Image for 14 Leanihi Ln B204 24 of 38 Listing Image for 14 Leanihi Ln B204 25 of 38 Listing Image for 14 Leanihi Ln B204 26 of 38 Listing Image for 14 Leanihi Ln B204 27 of 38 Listing Image for 14 Leanihi Ln B204 28 of 38 Listing Image for 14 Leanihi Ln B204 29 of 38 Listing Image for 14 Leanihi Ln B204 30 of 38 Listing Image for 14 Leanihi Ln B204 31 of 38 Listing Image for 14 Leanihi Ln B204 32 of 38 Listing Image for 14 Leanihi Ln B204 33 of 38 Listing Image for 14 Leanihi Ln B204 34 of 38 Listing Image for 14 Leanihi Ln B204 35 of 38 Listing Image for 14 Leanihi Ln B204 36 of 38 Listing Image for 14 Leanihi Ln B204 37 of 38 Listing Image for 14 Leanihi Ln B204 38 of 38

$1,299,900

↓ $99,100

Ke Alii Ocean Villas B204

14 Leanihi Ln B204, Kihei

2 Beds 2 Baths 1,233 SqFt Residential MLS® # 408886

Days on Market: 201

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

Listing Image for 453 N Honokala Rd 1 of 33 Listing Image for 453 N Honokala Rd 2 of 33 Listing Image for 453 N Honokala Rd 3 of 33 Listing Image for 453 N Honokala Rd 4 of 33 Listing Image for 453 N Honokala Rd 5 of 33 Listing Image for 453 N Honokala Rd 6 of 33 Listing Image for 453 N Honokala Rd 7 of 33 Listing Image for 453 N Honokala Rd 8 of 33 Listing Image for 453 N Honokala Rd 9 of 33 Listing Image for 453 N Honokala Rd 10 of 33 Listing Image for 453 N Honokala Rd 11 of 33 Listing Image for 453 N Honokala Rd 12 of 33 Listing Image for 453 N Honokala Rd 13 of 33 Listing Image for 453 N Honokala Rd 14 of 33 Listing Image for 453 N Honokala Rd 15 of 33 Listing Image for 453 N Honokala Rd 16 of 33 Listing Image for 453 N Honokala Rd 17 of 33 Listing Image for 453 N Honokala Rd 18 of 33 Listing Image for 453 N Honokala Rd 19 of 33 Listing Image for 453 N Honokala Rd 20 of 33 Listing Image for 453 N Honokala Rd 21 of 33 Listing Image for 453 N Honokala Rd 22 of 33 Listing Image for 453 N Honokala Rd 23 of 33 Listing Image for 453 N Honokala Rd 24 of 33 Listing Image for 453 N Honokala Rd 25 of 33 Listing Image for 453 N Honokala Rd 26 of 33 Listing Image for 453 N Honokala Rd 27 of 33 Listing Image for 453 N Honokala Rd 28 of 33 Listing Image for 453 N Honokala Rd 29 of 33 Listing Image for 453 N Honokala Rd 30 of 33 Listing Image for 453 N Honokala Rd 31 of 33 Listing Image for 453 N Honokala Rd 32 of 33 Listing Image for 453 N Honokala Rd 33 of 33

$2,325,000

Huelo Hui

453 N Honokala Rd, Haiku

3 Beds 2 Baths 1,564 SqFt Residential MLS® # 408878

Days on Market: 202

Compass-W

Listing Image for 41 Kokea 1003 1 of 33 Listing Image for 41 Kokea 1003 2 of 33 Listing Image for 41 Kokea 1003 3 of 33 Listing Image for 41 Kokea 1003 4 of 33 Listing Image for 41 Kokea 1003 5 of 33 Listing Image for 41 Kokea 1003 6 of 33 Listing Image for 41 Kokea 1003 7 of 33 Listing Image for 41 Kokea 1003 8 of 33 Listing Image for 41 Kokea 1003 9 of 33 Listing Image for 41 Kokea 1003 10 of 33 Listing Image for 41 Kokea 1003 11 of 33 Listing Image for 41 Kokea 1003 12 of 33 Listing Image for 41 Kokea 1003 13 of 33 Listing Image for 41 Kokea 1003 14 of 33 Listing Image for 41 Kokea 1003 15 of 33 Listing Image for 41 Kokea 1003 16 of 33 Listing Image for 41 Kokea 1003 17 of 33 Listing Image for 41 Kokea 1003 18 of 33 Listing Image for 41 Kokea 1003 19 of 33 Listing Image for 41 Kokea 1003 20 of 33 Listing Image for 41 Kokea 1003 21 of 33 Listing Image for 41 Kokea 1003 22 of 33 Listing Image for 41 Kokea 1003 23 of 33 Listing Image for 41 Kokea 1003 24 of 33 Listing Image for 41 Kokea 1003 25 of 33 Listing Image for 41 Kokea 1003 26 of 33 Listing Image for 41 Kokea 1003 27 of 33 Listing Image for 41 Kokea 1003 28 of 33 Listing Image for 41 Kokea 1003 29 of 33 Listing Image for 41 Kokea 1003 30 of 33 Listing Image for 41 Kokea 1003 31 of 33 Listing Image for 41 Kokea 1003 32 of 33 Listing Image for 41 Kokea 1003 33 of 33

$1,099,000

Villas at Kehalani 1003

41 Kokea 1003, Wailuku

2 Beds 2.5 Baths 1,446 SqFt Residential MLS® # 408877

Days on Market: 202

Keller Williams Realty Maui-Ki Cell: 808-371-6475

In Escrow
Listing Image for 4584 Makena Rd 1 of 30 Listing Image for 4584 Makena Rd 2 of 30 Listing Image for 4584 Makena Rd 3 of 30 Listing Image for 4584 Makena Rd 4 of 30 Listing Image for 4584 Makena Rd 5 of 30 Listing Image for 4584 Makena Rd 6 of 30 Listing Image for 4584 Makena Rd 7 of 30 Listing Image for 4584 Makena Rd 8 of 30 Listing Image for 4584 Makena Rd 9 of 30 Listing Image for 4584 Makena Rd 10 of 30 Listing Image for 4584 Makena Rd 11 of 30 Listing Image for 4584 Makena Rd 12 of 30 Listing Image for 4584 Makena Rd 13 of 30 Listing Image for 4584 Makena Rd 14 of 30 Listing Image for 4584 Makena Rd 15 of 30 Listing Image for 4584 Makena Rd 16 of 30 Listing Image for 4584 Makena Rd 17 of 30 Listing Image for 4584 Makena Rd 18 of 30 Listing Image for 4584 Makena Rd 19 of 30 Listing Image for 4584 Makena Rd 20 of 30 Listing Image for 4584 Makena Rd 21 of 30 Listing Image for 4584 Makena Rd 22 of 30 Listing Image for 4584 Makena Rd 23 of 30 Listing Image for 4584 Makena Rd 24 of 30 Listing Image for 4584 Makena Rd 25 of 30 Listing Image for 4584 Makena Rd 26 of 30 Listing Image for 4584 Makena Rd 27 of 30 Listing Image for 4584 Makena Rd 28 of 30 Listing Image for 4584 Makena Rd 29 of 30 Listing Image for 4584 Makena Rd 30 of 30

$9,000,000

Wailea/Makena

4584 Makena Rd, Wailea/Makena

2 Beds 3.5 Baths 2,760 SqFt Residential MLS® # 408876

Days on Market: 202

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

Short Term Rental
Listing Image for 10 Wailea Ekolu Pl 203 1 of 49 Listing Image for 10 Wailea Ekolu Pl 203 2 of 49 Listing Image for 10 Wailea Ekolu Pl 203 3 of 49 Listing Image for 10 Wailea Ekolu Pl 203 4 of 49 Listing Image for 10 Wailea Ekolu Pl 203 5 of 49 Listing Image for 10 Wailea Ekolu Pl 203 6 of 49 Listing Image for 10 Wailea Ekolu Pl 203 7 of 49 Listing Image for 10 Wailea Ekolu Pl 203 8 of 49 Listing Image for 10 Wailea Ekolu Pl 203 9 of 49 Listing Image for 10 Wailea Ekolu Pl 203 10 of 49 Listing Image for 10 Wailea Ekolu Pl 203 11 of 49 Listing Image for 10 Wailea Ekolu Pl 203 12 of 49 Listing Image for 10 Wailea Ekolu Pl 203 13 of 49 Listing Image for 10 Wailea Ekolu Pl 203 14 of 49 Listing Image for 10 Wailea Ekolu Pl 203 15 of 49 Listing Image for 10 Wailea Ekolu Pl 203 16 of 49 Listing Image for 10 Wailea Ekolu Pl 203 17 of 49 Listing Image for 10 Wailea Ekolu Pl 203 18 of 49 Listing Image for 10 Wailea Ekolu Pl 203 19 of 49 Listing Image for 10 Wailea Ekolu Pl 203 20 of 49 Listing Image for 10 Wailea Ekolu Pl 203 21 of 49 Listing Image for 10 Wailea Ekolu Pl 203 22 of 49 Listing Image for 10 Wailea Ekolu Pl 203 23 of 49 Listing Image for 10 Wailea Ekolu Pl 203 24 of 49 Listing Image for 10 Wailea Ekolu Pl 203 25 of 49 Listing Image for 10 Wailea Ekolu Pl 203 26 of 49 Listing Image for 10 Wailea Ekolu Pl 203 27 of 49 Listing Image for 10 Wailea Ekolu Pl 203 28 of 49 Listing Image for 10 Wailea Ekolu Pl 203 29 of 49 Listing Image for 10 Wailea Ekolu Pl 203 30 of 49 Listing Image for 10 Wailea Ekolu Pl 203 31 of 49 Listing Image for 10 Wailea Ekolu Pl 203 32 of 49 Listing Image for 10 Wailea Ekolu Pl 203 33 of 49 Listing Image for 10 Wailea Ekolu Pl 203 34 of 49 Listing Image for 10 Wailea Ekolu Pl 203 35 of 49 Listing Image for 10 Wailea Ekolu Pl 203 36 of 49 Listing Image for 10 Wailea Ekolu Pl 203 37 of 49 Listing Image for 10 Wailea Ekolu Pl 203 38 of 49 Listing Image for 10 Wailea Ekolu Pl 203 39 of 49 Listing Image for 10 Wailea Ekolu Pl 203 40 of 49 Listing Image for 10 Wailea Ekolu Pl 203 41 of 49 Listing Image for 10 Wailea Ekolu Pl 203 42 of 49 Listing Image for 10 Wailea Ekolu Pl 203 43 of 49 Listing Image for 10 Wailea Ekolu Pl 203 44 of 49 Listing Image for 10 Wailea Ekolu Pl 203 45 of 49 Listing Image for 10 Wailea Ekolu Pl 203 46 of 49 Listing Image for 10 Wailea Ekolu Pl 203 47 of 49 Listing Image for 10 Wailea Ekolu Pl 203 48 of 49 Listing Image for 10 Wailea Ekolu Pl 203 49 of 49

$1,335,000

↓ $100,000

Wailea Ekolu 203

10 Wailea Ekolu Pl 203, Wailea/Makena

2 Beds 2 Baths 1,071 SqFt Residential MLS® # 408874

Days on Market: 202

Hawaii Life (W) Cell: 808-208-1385

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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