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:

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.

Recent Sales on Maui

Sold
Closed: 04/23/2026
Listing Image for 281 Pua Kalaunu Loop 1 of 27 Listing Image for 281 Pua Kalaunu Loop 2 of 27 Listing Image for 281 Pua Kalaunu Loop 3 of 27 Listing Image for 281 Pua Kalaunu Loop 4 of 27 Listing Image for 281 Pua Kalaunu Loop 5 of 27 Listing Image for 281 Pua Kalaunu Loop 6 of 27 Listing Image for 281 Pua Kalaunu Loop 7 of 27 Listing Image for 281 Pua Kalaunu Loop 8 of 27 Listing Image for 281 Pua Kalaunu Loop 9 of 27 Listing Image for 281 Pua Kalaunu Loop 10 of 27 Listing Image for 281 Pua Kalaunu Loop 11 of 27 Listing Image for 281 Pua Kalaunu Loop 12 of 27 Listing Image for 281 Pua Kalaunu Loop 13 of 27 Listing Image for 281 Pua Kalaunu Loop 14 of 27 Listing Image for 281 Pua Kalaunu Loop 15 of 27 Listing Image for 281 Pua Kalaunu Loop 16 of 27 Listing Image for 281 Pua Kalaunu Loop 17 of 27 Listing Image for 281 Pua Kalaunu Loop 18 of 27 Listing Image for 281 Pua Kalaunu Loop 19 of 27 Listing Image for 281 Pua Kalaunu Loop 20 of 27 Listing Image for 281 Pua Kalaunu Loop 21 of 27 Listing Image for 281 Pua Kalaunu Loop 22 of 27 Listing Image for 281 Pua Kalaunu Loop 23 of 27 Listing Image for 281 Pua Kalaunu Loop 24 of 27 Listing Image for 281 Pua Kalaunu Loop 25 of 27 Listing Image for 281 Pua Kalaunu Loop 26 of 27 Listing Image for 281 Pua Kalaunu Loop 27 of 27

$1,187,500

↓ $111,500

Anuhea at Kehalani

281 Pua Kalaunu Loop, Wailuku

3 Beds 2 Baths 1,638 SqFt Residential MLS® # 405865 Date Sold: April 23, 2026
Sold
Closed: 06/18/2025
Listing Image for 566 Hoene St 1 of 50 Listing Image for 566 Hoene St 2 of 50 Listing Image for 566 Hoene St 3 of 50 Listing Image for 566 Hoene St 4 of 50 Listing Image for 566 Hoene St 5 of 50 Listing Image for 566 Hoene St 6 of 50 Listing Image for 566 Hoene St 7 of 50 Listing Image for 566 Hoene St 8 of 50 Listing Image for 566 Hoene St 9 of 50 Listing Image for 566 Hoene St 10 of 50 Listing Image for 566 Hoene St 11 of 50 Listing Image for 566 Hoene St 12 of 50 Listing Image for 566 Hoene St 13 of 50 Listing Image for 566 Hoene St 14 of 50 Listing Image for 566 Hoene St 15 of 50 Listing Image for 566 Hoene St 16 of 50 Listing Image for 566 Hoene St 17 of 50 Listing Image for 566 Hoene St 18 of 50 Listing Image for 566 Hoene St 19 of 50 Listing Image for 566 Hoene St 20 of 50 Listing Image for 566 Hoene St 21 of 50 Listing Image for 566 Hoene St 22 of 50 Listing Image for 566 Hoene St 23 of 50 Listing Image for 566 Hoene St 24 of 50 Listing Image for 566 Hoene St 25 of 50 Listing Image for 566 Hoene St 26 of 50 Listing Image for 566 Hoene St 27 of 50 Listing Image for 566 Hoene St 28 of 50 Listing Image for 566 Hoene St 29 of 50 Listing Image for 566 Hoene St 30 of 50 Listing Image for 566 Hoene St 31 of 50 Listing Image for 566 Hoene St 32 of 50 Listing Image for 566 Hoene St 33 of 50 Listing Image for 566 Hoene St 34 of 50 Listing Image for 566 Hoene St 35 of 50 Listing Image for 566 Hoene St 36 of 50 Listing Image for 566 Hoene St 37 of 50 Listing Image for 566 Hoene St 38 of 50 Listing Image for 566 Hoene St 39 of 50 Listing Image for 566 Hoene St 40 of 50 Listing Image for 566 Hoene St 41 of 50 Listing Image for 566 Hoene St 42 of 50 Listing Image for 566 Hoene St 43 of 50 Listing Image for 566 Hoene St 44 of 50 Listing Image for 566 Hoene St 45 of 50 Listing Image for 566 Hoene St 46 of 50 Listing Image for 566 Hoene St 47 of 50 Listing Image for 566 Hoene St 48 of 50 Listing Image for 566 Hoene St 49 of 50 Listing Image for 566 Hoene St 50 of 50

$1,650,000

Makawao/Olinda/Haliimaile

566 Hoene St, Makawao/Olinda/Haliimaile

5 Beds 3 Baths 2,512 SqFt Residential MLS® # 405253 Date Sold: June 18, 2025
Sold
Closed: 06/12/2025
Listing Image for 155 Wailea Ike Pl 92 1 of 43 Listing Image for 155 Wailea Ike Pl 92 2 of 43 Listing Image for 155 Wailea Ike Pl 92 3 of 43 Listing Image for 155 Wailea Ike Pl 92 4 of 43 Listing Image for 155 Wailea Ike Pl 92 5 of 43 Listing Image for 155 Wailea Ike Pl 92 6 of 43 Listing Image for 155 Wailea Ike Pl 92 7 of 43 Listing Image for 155 Wailea Ike Pl 92 8 of 43 Listing Image for 155 Wailea Ike Pl 92 9 of 43 Listing Image for 155 Wailea Ike Pl 92 10 of 43 Listing Image for 155 Wailea Ike Pl 92 11 of 43 Listing Image for 155 Wailea Ike Pl 92 12 of 43 Listing Image for 155 Wailea Ike Pl 92 13 of 43 Listing Image for 155 Wailea Ike Pl 92 14 of 43 Listing Image for 155 Wailea Ike Pl 92 15 of 43 Listing Image for 155 Wailea Ike Pl 92 16 of 43 Listing Image for 155 Wailea Ike Pl 92 17 of 43 Listing Image for 155 Wailea Ike Pl 92 18 of 43 Listing Image for 155 Wailea Ike Pl 92 19 of 43 Listing Image for 155 Wailea Ike Pl 92 20 of 43 Listing Image for 155 Wailea Ike Pl 92 21 of 43 Listing Image for 155 Wailea Ike Pl 92 22 of 43 Listing Image for 155 Wailea Ike Pl 92 23 of 43 Listing Image for 155 Wailea Ike Pl 92 24 of 43 Listing Image for 155 Wailea Ike Pl 92 25 of 43 Listing Image for 155 Wailea Ike Pl 92 26 of 43 Listing Image for 155 Wailea Ike Pl 92 27 of 43 Listing Image for 155 Wailea Ike Pl 92 28 of 43 Listing Image for 155 Wailea Ike Pl 92 29 of 43 Listing Image for 155 Wailea Ike Pl 92 30 of 43 Listing Image for 155 Wailea Ike Pl 92 31 of 43 Listing Image for 155 Wailea Ike Pl 92 32 of 43 Listing Image for 155 Wailea Ike Pl 92 33 of 43 Listing Image for 155 Wailea Ike Pl 92 34 of 43 Listing Image for 155 Wailea Ike Pl 92 35 of 43 Listing Image for 155 Wailea Ike Pl 92 36 of 43 Listing Image for 155 Wailea Ike Pl 92 37 of 43 Listing Image for 155 Wailea Ike Pl 92 38 of 43 Listing Image for 155 Wailea Ike Pl 92 39 of 43 Listing Image for 155 Wailea Ike Pl 92 40 of 43 Listing Image for 155 Wailea Ike Pl 92 41 of 43 Listing Image for 155 Wailea Ike Pl 92 42 of 43 Listing Image for 155 Wailea Ike Pl 92 43 of 43

$865,804

Grand Champions 92

155 Wailea Ike Pl 92, Wailea/Makena

1 Bed 2 Baths 908 SqFt Residential MLS® # 405379 Date Sold: June 12, 2025
Sold
Closed: 02/27/2026
Listing Image for 63 Pua Kalaunu Loop Lot 37 1 of 18 Listing Image for 63 Pua Kalaunu Loop Lot 37 2 of 18 Listing Image for 63 Pua Kalaunu Loop Lot 37 3 of 18 Listing Image for 63 Pua Kalaunu Loop Lot 37 4 of 18 Listing Image for 63 Pua Kalaunu Loop Lot 37 5 of 18 Listing Image for 63 Pua Kalaunu Loop Lot 37 6 of 18 Listing Image for 63 Pua Kalaunu Loop Lot 37 7 of 18 Listing Image for 63 Pua Kalaunu Loop Lot 37 8 of 18 Listing Image for 63 Pua Kalaunu Loop Lot 37 9 of 18 Listing Image for 63 Pua Kalaunu Loop Lot 37 10 of 18 Listing Image for 63 Pua Kalaunu Loop Lot 37 11 of 18 Listing Image for 63 Pua Kalaunu Loop Lot 37 12 of 18 Listing Image for 63 Pua Kalaunu Loop Lot 37 13 of 18 Listing Image for 63 Pua Kalaunu Loop Lot 37 14 of 18 Listing Image for 63 Pua Kalaunu Loop Lot 37 15 of 18 Listing Image for 63 Pua Kalaunu Loop Lot 37 16 of 18 Listing Image for 63 Pua Kalaunu Loop Lot 37 17 of 18 Listing Image for 63 Pua Kalaunu Loop Lot 37 18 of 18

$1,185,000

↓ $114,900

Anuhea at Kehalani

63 Pua Kalaunu Loop Lot 37, Wailuku

3 Beds 2 Baths 1,744 SqFt Residential MLS® # 402528 Date Sold: February 27, 2026
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
Sold
Closed: 01/09/2026
Listing Image for 3150 Wailea Alanui Dr 3007 1 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 2 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 3 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 4 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 5 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 6 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 7 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 8 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 9 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 10 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 11 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 12 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 13 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 14 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 15 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 16 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 17 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 18 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 19 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 20 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 21 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 22 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 23 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 24 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 25 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 26 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 27 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 28 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 29 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 30 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 31 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 32 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 33 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 34 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 35 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 36 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 37 of 38 Listing Image for 3150 Wailea Alanui Dr 3007 38 of 38

$1,250,000

Wailea Palms 3007

3150 Wailea Alanui Dr 3007, Wailea/Makena

1 Bed 2 Baths 1,022 SqFt Residential MLS® # 406232 Date Sold: January 9, 2026
Sold
Closed: 06/12/2025
Listing Image for 172 Holomoana Way 11b 1 of 48 Listing Image for 172 Holomoana Way 11b 2 of 48 Listing Image for 172 Holomoana Way 11b 3 of 48 Listing Image for 172 Holomoana Way 11b 4 of 48 Listing Image for 172 Holomoana Way 11b 5 of 48 Listing Image for 172 Holomoana Way 11b 6 of 48 Listing Image for 172 Holomoana Way 11b 7 of 48 Listing Image for 172 Holomoana Way 11b 8 of 48 Listing Image for 172 Holomoana Way 11b 9 of 48 Listing Image for 172 Holomoana Way 11b 10 of 48 Listing Image for 172 Holomoana Way 11b 11 of 48 Listing Image for 172 Holomoana Way 11b 12 of 48 Listing Image for 172 Holomoana Way 11b 13 of 48 Listing Image for 172 Holomoana Way 11b 14 of 48 Listing Image for 172 Holomoana Way 11b 15 of 48 Listing Image for 172 Holomoana Way 11b 16 of 48 Listing Image for 172 Holomoana Way 11b 17 of 48 Listing Image for 172 Holomoana Way 11b 18 of 48 Listing Image for 172 Holomoana Way 11b 19 of 48 Listing Image for 172 Holomoana Way 11b 20 of 48 Listing Image for 172 Holomoana Way 11b 21 of 48 Listing Image for 172 Holomoana Way 11b 22 of 48 Listing Image for 172 Holomoana Way 11b 23 of 48 Listing Image for 172 Holomoana Way 11b 24 of 48 Listing Image for 172 Holomoana Way 11b 25 of 48 Listing Image for 172 Holomoana Way 11b 26 of 48 Listing Image for 172 Holomoana Way 11b 27 of 48 Listing Image for 172 Holomoana Way 11b 28 of 48 Listing Image for 172 Holomoana Way 11b 29 of 48 Listing Image for 172 Holomoana Way 11b 30 of 48 Listing Image for 172 Holomoana Way 11b 31 of 48 Listing Image for 172 Holomoana Way 11b 32 of 48 Listing Image for 172 Holomoana Way 11b 33 of 48 Listing Image for 172 Holomoana Way 11b 34 of 48 Listing Image for 172 Holomoana Way 11b 35 of 48 Listing Image for 172 Holomoana Way 11b 36 of 48 Listing Image for 172 Holomoana Way 11b 37 of 48 Listing Image for 172 Holomoana Way 11b 38 of 48 Listing Image for 172 Holomoana Way 11b 39 of 48 Listing Image for 172 Holomoana Way 11b 40 of 48 Listing Image for 172 Holomoana Way 11b 41 of 48 Listing Image for 172 Holomoana Way 11b 42 of 48 Listing Image for 172 Holomoana Way 11b 43 of 48 Listing Image for 172 Holomoana Way 11b 44 of 48 Listing Image for 172 Holomoana Way 11b 45 of 48 Listing Image for 172 Holomoana Way 11b 46 of 48 Listing Image for 172 Holomoana Way 11b 47 of 48 Listing Image for 172 Holomoana Way 11b 48 of 48

$2,570,000

Makalii at Wailea 11B

172 Holomoana Way 11b, Wailea/Makena

2 Beds 2 Baths 1,574 SqFt Residential MLS® # 404595 Date Sold: June 12, 2025
View 6 More Listings

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.