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

Sort by:
Listing Image for 110 Awaiku St 1 of 47 Listing Image for 110 Awaiku St 2 of 47 Listing Image for 110 Awaiku St 3 of 47 Listing Image for 110 Awaiku St 4 of 47 Listing Image for 110 Awaiku St 5 of 47 Listing Image for 110 Awaiku St 6 of 47 Listing Image for 110 Awaiku St 7 of 47 Listing Image for 110 Awaiku St 8 of 47 Listing Image for 110 Awaiku St 9 of 47 Listing Image for 110 Awaiku St 10 of 47 Listing Image for 110 Awaiku St 11 of 47 Listing Image for 110 Awaiku St 12 of 47 Listing Image for 110 Awaiku St 13 of 47 Listing Image for 110 Awaiku St 14 of 47 Listing Image for 110 Awaiku St 15 of 47 Listing Image for 110 Awaiku St 16 of 47 Listing Image for 110 Awaiku St 17 of 47 Listing Image for 110 Awaiku St 18 of 47 Listing Image for 110 Awaiku St 19 of 47 Listing Image for 110 Awaiku St 20 of 47 Listing Image for 110 Awaiku St 21 of 47 Listing Image for 110 Awaiku St 22 of 47 Listing Image for 110 Awaiku St 23 of 47 Listing Image for 110 Awaiku St 24 of 47 Listing Image for 110 Awaiku St 25 of 47 Listing Image for 110 Awaiku St 26 of 47 Listing Image for 110 Awaiku St 27 of 47 Listing Image for 110 Awaiku St 28 of 47 Listing Image for 110 Awaiku St 29 of 47 Listing Image for 110 Awaiku St 30 of 47 Listing Image for 110 Awaiku St 31 of 47 Listing Image for 110 Awaiku St 32 of 47 Listing Image for 110 Awaiku St 33 of 47 Listing Image for 110 Awaiku St 34 of 47 Listing Image for 110 Awaiku St 35 of 47 Listing Image for 110 Awaiku St 36 of 47 Listing Image for 110 Awaiku St 37 of 47 Listing Image for 110 Awaiku St 38 of 47 Listing Image for 110 Awaiku St 39 of 47 Listing Image for 110 Awaiku St 40 of 47 Listing Image for 110 Awaiku St 41 of 47 Listing Image for 110 Awaiku St 42 of 47 Listing Image for 110 Awaiku St 43 of 47 Listing Image for 110 Awaiku St 44 of 47 Listing Image for 110 Awaiku St 45 of 47 Listing Image for 110 Awaiku St 46 of 47 Listing Image for 110 Awaiku St 47 of 47

$3,195,000

Mahanalua Nui

110 Awaiku St, Lahaina

3 Beds 2.5 Baths 2,703 SqFt Residential MLS® # 410603

Days on Market: 23

Compass Cell: 808-283-7214

Listing Image for 1102 Mailuna Pl 1 of 50 Listing Image for 1102 Mailuna Pl 2 of 50 Listing Image for 1102 Mailuna Pl 3 of 50 Listing Image for 1102 Mailuna Pl 4 of 50 Listing Image for 1102 Mailuna Pl 5 of 50 Listing Image for 1102 Mailuna Pl 6 of 50 Listing Image for 1102 Mailuna Pl 7 of 50 Listing Image for 1102 Mailuna Pl 8 of 50 Listing Image for 1102 Mailuna Pl 9 of 50 Listing Image for 1102 Mailuna Pl 10 of 50 Listing Image for 1102 Mailuna Pl 11 of 50 Listing Image for 1102 Mailuna Pl 12 of 50 Listing Image for 1102 Mailuna Pl 13 of 50 Listing Image for 1102 Mailuna Pl 14 of 50 Listing Image for 1102 Mailuna Pl 15 of 50 Listing Image for 1102 Mailuna Pl 16 of 50 Listing Image for 1102 Mailuna Pl 17 of 50 Listing Image for 1102 Mailuna Pl 18 of 50 Listing Image for 1102 Mailuna Pl 19 of 50 Listing Image for 1102 Mailuna Pl 20 of 50 Listing Image for 1102 Mailuna Pl 21 of 50 Listing Image for 1102 Mailuna Pl 22 of 50 Listing Image for 1102 Mailuna Pl 23 of 50 Listing Image for 1102 Mailuna Pl 24 of 50 Listing Image for 1102 Mailuna Pl 25 of 50 Listing Image for 1102 Mailuna Pl 26 of 50 Listing Image for 1102 Mailuna Pl 27 of 50 Listing Image for 1102 Mailuna Pl 28 of 50 Listing Image for 1102 Mailuna Pl 29 of 50 Listing Image for 1102 Mailuna Pl 30 of 50 Listing Image for 1102 Mailuna Pl 31 of 50 Listing Image for 1102 Mailuna Pl 32 of 50 Listing Image for 1102 Mailuna Pl 33 of 50 Listing Image for 1102 Mailuna Pl 34 of 50 Listing Image for 1102 Mailuna Pl 35 of 50 Listing Image for 1102 Mailuna Pl 36 of 50 Listing Image for 1102 Mailuna Pl 37 of 50 Listing Image for 1102 Mailuna Pl 38 of 50 Listing Image for 1102 Mailuna Pl 39 of 50 Listing Image for 1102 Mailuna Pl 40 of 50 Listing Image for 1102 Mailuna Pl 41 of 50 Listing Image for 1102 Mailuna Pl 42 of 50 Listing Image for 1102 Mailuna Pl 43 of 50 Listing Image for 1102 Mailuna Pl 44 of 50 Listing Image for 1102 Mailuna Pl 45 of 50 Listing Image for 1102 Mailuna Pl 46 of 50 Listing Image for 1102 Mailuna Pl 47 of 50 Listing Image for 1102 Mailuna Pl 48 of 50 Listing Image for 1102 Mailuna Pl 49 of 50 Listing Image for 1102 Mailuna Pl 50 of 50

$1,569,500

Meadows at Makawao

1102 Mailuna Pl, Makawao/Olinda/Haliimaile

3 Beds 3 Baths 2,323 SqFt Residential MLS® # 410602

Days on Market: 20

Equity One Real Estate Inc (P) Cell: 808-283-1775

In Escrow
Listing Image for 343 Noe St 1 of 29 Listing Image for 343 Noe St 2 of 29 Listing Image for 343 Noe St 3 of 29 Listing Image for 343 Noe St 4 of 29 Listing Image for 343 Noe St 5 of 29 Listing Image for 343 Noe St 6 of 29 Listing Image for 343 Noe St 7 of 29 Listing Image for 343 Noe St 8 of 29 Listing Image for 343 Noe St 9 of 29 Listing Image for 343 Noe St 10 of 29 Listing Image for 343 Noe St 11 of 29 Listing Image for 343 Noe St 12 of 29 Listing Image for 343 Noe St 13 of 29 Listing Image for 343 Noe St 14 of 29 Listing Image for 343 Noe St 15 of 29 Listing Image for 343 Noe St 16 of 29 Listing Image for 343 Noe St 17 of 29 Listing Image for 343 Noe St 18 of 29 Listing Image for 343 Noe St 19 of 29 Listing Image for 343 Noe St 20 of 29 Listing Image for 343 Noe St 21 of 29 Listing Image for 343 Noe St 22 of 29 Listing Image for 343 Noe St 23 of 29 Listing Image for 343 Noe St 24 of 29 Listing Image for 343 Noe St 25 of 29 Listing Image for 343 Noe St 26 of 29 Listing Image for 343 Noe St 27 of 29 Listing Image for 343 Noe St 28 of 29 Listing Image for 343 Noe St 29 of 29

$1,350,000

Kihei

343 Noe St, Kihei

3 Beds 3 Baths 1,508 SqFt Residential MLS® # 410600

Days on Market: 20

Big Wave Realty LLC

Short Term Rental
Listing Image for 130 Kai Malina Pkwy Sr530 1 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 2 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 3 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 4 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 5 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 6 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 7 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 8 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 9 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 10 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 11 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 12 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 13 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 14 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 15 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 16 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 17 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 18 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 19 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 20 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 21 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 22 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 23 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 24 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 25 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 26 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 27 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 28 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 29 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 30 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 31 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 32 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 33 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 34 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 35 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 36 of 37 Listing Image for 130 Kai Malina Pkwy Sr530 37 of 37

$1,200,000

Honua Kai - Hoku Lani SR530

130 Kai Malina Pkwy Sr530, Kaanapali

1 Bed 1 Bath 765 SqFt Residential MLS® # 410599

Days on Market: 21

Keller Williams Realty Maui-L Cell: 808-870-2525

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
Short Term Rental
Listing Image for 2575 S Kihei Rd T210 1 of 33 Listing Image for 2575 S Kihei Rd T210 2 of 33 Listing Image for 2575 S Kihei Rd T210 3 of 33 Listing Image for 2575 S Kihei Rd T210 4 of 33 Listing Image for 2575 S Kihei Rd T210 5 of 33 Listing Image for 2575 S Kihei Rd T210 6 of 33 Listing Image for 2575 S Kihei Rd T210 7 of 33 Listing Image for 2575 S Kihei Rd T210 8 of 33 Listing Image for 2575 S Kihei Rd T210 9 of 33 Listing Image for 2575 S Kihei Rd T210 10 of 33 Listing Image for 2575 S Kihei Rd T210 11 of 33 Listing Image for 2575 S Kihei Rd T210 12 of 33 Listing Image for 2575 S Kihei Rd T210 13 of 33 Listing Image for 2575 S Kihei Rd T210 14 of 33 Listing Image for 2575 S Kihei Rd T210 15 of 33 Listing Image for 2575 S Kihei Rd T210 16 of 33 Listing Image for 2575 S Kihei Rd T210 17 of 33 Listing Image for 2575 S Kihei Rd T210 18 of 33 Listing Image for 2575 S Kihei Rd T210 19 of 33 Listing Image for 2575 S Kihei Rd T210 20 of 33 Listing Image for 2575 S Kihei Rd T210 21 of 33 Listing Image for 2575 S Kihei Rd T210 22 of 33 Listing Image for 2575 S Kihei Rd T210 23 of 33 Listing Image for 2575 S Kihei Rd T210 24 of 33 Listing Image for 2575 S Kihei Rd T210 25 of 33 Listing Image for 2575 S Kihei Rd T210 26 of 33 Listing Image for 2575 S Kihei Rd T210 27 of 33 Listing Image for 2575 S Kihei Rd T210 28 of 33 Listing Image for 2575 S Kihei Rd T210 29 of 33 Listing Image for 2575 S Kihei Rd T210 30 of 33 Listing Image for 2575 S Kihei Rd T210 31 of 33 Listing Image for 2575 S Kihei Rd T210 32 of 33 Listing Image for 2575 S Kihei Rd T210 33 of 33

$879,000

Maui Banyan T210

2575 S Kihei Rd T210, Kihei

2 Beds 2 Baths 890 SqFt Residential MLS® # 410598

Days on Market: 21

Compass Cell: 808-283-0079

Short Term Rental
Listing Image for 4521 Lower Honoapiilani Rd 2a2 1 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 2 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 3 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 4 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 5 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 6 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 7 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 8 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 9 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 10 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 11 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 12 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 13 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 14 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 15 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 16 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 17 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 18 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 19 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 20 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 21 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 22 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 23 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 24 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 25 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 26 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 27 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 28 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 29 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 30 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 31 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 32 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 33 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 34 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 35 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 36 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 37 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 38 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 39 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 40 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 41 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 42 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 43 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 44 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 45 of 46 Listing Image for 4521 Lower Honoapiilani Rd 2a2 46 of 46

$1,199,000

Kahana Outrigger 2A2

4521 Lower Honoapiilani Rd 2a2, Napili/Kahana/Honokowai

3 Beds 3 Baths 1,448 SqFt Residential MLS® # 410597

Days on Market: 21

Compass-W

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.

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.

Provide a valid email address.
Newsletter consent

Posted by Evan Harlow R(S) on

Enjoy this blog post? Click here to subscribe for updates

Tags

Email Send a link to post via Email

Leave A Comment

e.g. yourwebsitename.com
Please note that your email address is kept private upon posting.