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. 

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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: 03/25/2026
Listing Image for 357 Umeke St 144 1 of 50 Listing Image for 357 Umeke St 144 2 of 50 Listing Image for 357 Umeke St 144 3 of 50 Listing Image for 357 Umeke St 144 4 of 50 Listing Image for 357 Umeke St 144 5 of 50 Listing Image for 357 Umeke St 144 6 of 50 Listing Image for 357 Umeke St 144 7 of 50 Listing Image for 357 Umeke St 144 8 of 50 Listing Image for 357 Umeke St 144 9 of 50 Listing Image for 357 Umeke St 144 10 of 50 Listing Image for 357 Umeke St 144 11 of 50 Listing Image for 357 Umeke St 144 12 of 50 Listing Image for 357 Umeke St 144 13 of 50 Listing Image for 357 Umeke St 144 14 of 50 Listing Image for 357 Umeke St 144 15 of 50 Listing Image for 357 Umeke St 144 16 of 50 Listing Image for 357 Umeke St 144 17 of 50 Listing Image for 357 Umeke St 144 18 of 50 Listing Image for 357 Umeke St 144 19 of 50 Listing Image for 357 Umeke St 144 20 of 50 Listing Image for 357 Umeke St 144 21 of 50 Listing Image for 357 Umeke St 144 22 of 50 Listing Image for 357 Umeke St 144 23 of 50 Listing Image for 357 Umeke St 144 24 of 50 Listing Image for 357 Umeke St 144 25 of 50 Listing Image for 357 Umeke St 144 26 of 50 Listing Image for 357 Umeke St 144 27 of 50 Listing Image for 357 Umeke St 144 28 of 50 Listing Image for 357 Umeke St 144 29 of 50 Listing Image for 357 Umeke St 144 30 of 50 Listing Image for 357 Umeke St 144 31 of 50 Listing Image for 357 Umeke St 144 32 of 50 Listing Image for 357 Umeke St 144 33 of 50 Listing Image for 357 Umeke St 144 34 of 50 Listing Image for 357 Umeke St 144 35 of 50 Listing Image for 357 Umeke St 144 36 of 50 Listing Image for 357 Umeke St 144 37 of 50 Listing Image for 357 Umeke St 144 38 of 50 Listing Image for 357 Umeke St 144 39 of 50 Listing Image for 357 Umeke St 144 40 of 50 Listing Image for 357 Umeke St 144 41 of 50 Listing Image for 357 Umeke St 144 42 of 50 Listing Image for 357 Umeke St 144 43 of 50 Listing Image for 357 Umeke St 144 44 of 50 Listing Image for 357 Umeke St 144 45 of 50 Listing Image for 357 Umeke St 144 46 of 50 Listing Image for 357 Umeke St 144 47 of 50 Listing Image for 357 Umeke St 144 48 of 50 Listing Image for 357 Umeke St 144 49 of 50 Listing Image for 357 Umeke St 144 50 of 50

$2,000,000

↓ $250,000

Hokulani Golf Villas 144

357 Umeke St 144, Kihei

4 Beds 3 Baths 2,548 SqFt Residential MLS® # 405817 Date Sold: March 25, 2026
Sold
Closed: 03/27/2026
Listing Image for 69 Pua Kalaunu Loop Lot 36 1 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 2 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 3 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 4 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 5 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 6 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 7 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 8 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 9 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 10 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 11 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 12 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 13 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 14 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 15 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 16 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 17 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 18 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 19 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 20 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 21 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 22 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 23 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 24 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 25 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 26 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 27 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 28 of 29 Listing Image for 69 Pua Kalaunu Loop Lot 36 29 of 29

$1,190,000

↓ $125,000

Anuhea at Kehalani

69 Pua Kalaunu Loop Lot 36, Wailuku

3 Beds 2 Baths 1,744 SqFt Residential MLS® # 402527 Date Sold: March 27, 2026
Sold
Closed: 01/14/2026
Listing Image for 85 Lau Awa Pl 1 of 50 Listing Image for 85 Lau Awa Pl 2 of 50 Listing Image for 85 Lau Awa Pl 3 of 50 Listing Image for 85 Lau Awa Pl 4 of 50 Listing Image for 85 Lau Awa Pl 5 of 50 Listing Image for 85 Lau Awa Pl 6 of 50 Listing Image for 85 Lau Awa Pl 7 of 50 Listing Image for 85 Lau Awa Pl 8 of 50 Listing Image for 85 Lau Awa Pl 9 of 50 Listing Image for 85 Lau Awa Pl 10 of 50 Listing Image for 85 Lau Awa Pl 11 of 50 Listing Image for 85 Lau Awa Pl 12 of 50 Listing Image for 85 Lau Awa Pl 13 of 50 Listing Image for 85 Lau Awa Pl 14 of 50 Listing Image for 85 Lau Awa Pl 15 of 50 Listing Image for 85 Lau Awa Pl 16 of 50 Listing Image for 85 Lau Awa Pl 17 of 50 Listing Image for 85 Lau Awa Pl 18 of 50 Listing Image for 85 Lau Awa Pl 19 of 50 Listing Image for 85 Lau Awa Pl 20 of 50 Listing Image for 85 Lau Awa Pl 21 of 50 Listing Image for 85 Lau Awa Pl 22 of 50 Listing Image for 85 Lau Awa Pl 23 of 50 Listing Image for 85 Lau Awa Pl 24 of 50 Listing Image for 85 Lau Awa Pl 25 of 50 Listing Image for 85 Lau Awa Pl 26 of 50 Listing Image for 85 Lau Awa Pl 27 of 50 Listing Image for 85 Lau Awa Pl 28 of 50 Listing Image for 85 Lau Awa Pl 29 of 50 Listing Image for 85 Lau Awa Pl 30 of 50 Listing Image for 85 Lau Awa Pl 31 of 50 Listing Image for 85 Lau Awa Pl 32 of 50 Listing Image for 85 Lau Awa Pl 33 of 50 Listing Image for 85 Lau Awa Pl 34 of 50 Listing Image for 85 Lau Awa Pl 35 of 50 Listing Image for 85 Lau Awa Pl 36 of 50 Listing Image for 85 Lau Awa Pl 37 of 50 Listing Image for 85 Lau Awa Pl 38 of 50 Listing Image for 85 Lau Awa Pl 39 of 50 Listing Image for 85 Lau Awa Pl 40 of 50 Listing Image for 85 Lau Awa Pl 41 of 50 Listing Image for 85 Lau Awa Pl 42 of 50 Listing Image for 85 Lau Awa Pl 43 of 50 Listing Image for 85 Lau Awa Pl 44 of 50 Listing Image for 85 Lau Awa Pl 45 of 50 Listing Image for 85 Lau Awa Pl 46 of 50 Listing Image for 85 Lau Awa Pl 47 of 50 Listing Image for 85 Lau Awa Pl 48 of 50 Listing Image for 85 Lau Awa Pl 49 of 50 Listing Image for 85 Lau Awa Pl 50 of 50

$5,250,000

Makila Plantation II

85 Lau Awa Pl, Lahaina

4 Beds 4 Baths 3,197 SqFt Residential MLS® # 403884 Date Sold: January 14, 2026
Sold
Closed: 12/26/2025
Listing Image for 450 Hoopalua Dr 1 of 43 Listing Image for 450 Hoopalua Dr 2 of 43 Listing Image for 450 Hoopalua Dr 3 of 43 Listing Image for 450 Hoopalua Dr 4 of 43 Listing Image for 450 Hoopalua Dr 5 of 43 Listing Image for 450 Hoopalua Dr 6 of 43 Listing Image for 450 Hoopalua Dr 7 of 43 Listing Image for 450 Hoopalua Dr 8 of 43 Listing Image for 450 Hoopalua Dr 9 of 43 Listing Image for 450 Hoopalua Dr 10 of 43 Listing Image for 450 Hoopalua Dr 11 of 43 Listing Image for 450 Hoopalua Dr 12 of 43 Listing Image for 450 Hoopalua Dr 13 of 43 Listing Image for 450 Hoopalua Dr 14 of 43 Listing Image for 450 Hoopalua Dr 15 of 43 Listing Image for 450 Hoopalua Dr 16 of 43 Listing Image for 450 Hoopalua Dr 17 of 43 Listing Image for 450 Hoopalua Dr 18 of 43 Listing Image for 450 Hoopalua Dr 19 of 43 Listing Image for 450 Hoopalua Dr 20 of 43 Listing Image for 450 Hoopalua Dr 21 of 43 Listing Image for 450 Hoopalua Dr 22 of 43 Listing Image for 450 Hoopalua Dr 23 of 43 Listing Image for 450 Hoopalua Dr 24 of 43 Listing Image for 450 Hoopalua Dr 25 of 43 Listing Image for 450 Hoopalua Dr 26 of 43 Listing Image for 450 Hoopalua Dr 27 of 43 Listing Image for 450 Hoopalua Dr 28 of 43 Listing Image for 450 Hoopalua Dr 29 of 43 Listing Image for 450 Hoopalua Dr 30 of 43 Listing Image for 450 Hoopalua Dr 31 of 43 Listing Image for 450 Hoopalua Dr 32 of 43 Listing Image for 450 Hoopalua Dr 33 of 43 Listing Image for 450 Hoopalua Dr 34 of 43 Listing Image for 450 Hoopalua Dr 35 of 43 Listing Image for 450 Hoopalua Dr 36 of 43 Listing Image for 450 Hoopalua Dr 37 of 43 Listing Image for 450 Hoopalua Dr 38 of 43 Listing Image for 450 Hoopalua Dr 39 of 43 Listing Image for 450 Hoopalua Dr 40 of 43 Listing Image for 450 Hoopalua Dr 41 of 43 Listing Image for 450 Hoopalua Dr 42 of 43 Listing Image for 450 Hoopalua Dr 43 of 43

$2,800,000

↓ $485,000

Kula 200

450 Hoopalua Dr, Pukalani

4 Beds 4 Baths 4,620 SqFt Residential MLS® # 406297 Date Sold: December 26, 2025
Sold
Closed: 08/18/2025
Listing Image for 142 Keoawa Pl 25 1 of 24 Listing Image for 142 Keoawa Pl 25 2 of 24 Listing Image for 142 Keoawa Pl 25 3 of 24 Listing Image for 142 Keoawa Pl 25 4 of 24 Listing Image for 142 Keoawa Pl 25 5 of 24 Listing Image for 142 Keoawa Pl 25 6 of 24 Listing Image for 142 Keoawa Pl 25 7 of 24 Listing Image for 142 Keoawa Pl 25 8 of 24 Listing Image for 142 Keoawa Pl 25 9 of 24 Listing Image for 142 Keoawa Pl 25 10 of 24 Listing Image for 142 Keoawa Pl 25 11 of 24 Listing Image for 142 Keoawa Pl 25 12 of 24 Listing Image for 142 Keoawa Pl 25 13 of 24 Listing Image for 142 Keoawa Pl 25 14 of 24 Listing Image for 142 Keoawa Pl 25 15 of 24 Listing Image for 142 Keoawa Pl 25 16 of 24 Listing Image for 142 Keoawa Pl 25 17 of 24 Listing Image for 142 Keoawa Pl 25 18 of 24 Listing Image for 142 Keoawa Pl 25 19 of 24 Listing Image for 142 Keoawa Pl 25 20 of 24 Listing Image for 142 Keoawa Pl 25 21 of 24 Listing Image for 142 Keoawa Pl 25 22 of 24 Listing Image for 142 Keoawa Pl 25 23 of 24 Listing Image for 142 Keoawa Pl 25 24 of 24

$3,100,000

Kapalua

142 Keoawa Pl 25, Kapalua

0 Beds 0 Baths 0 SqFt Land MLS® # 402870 Date Sold: August 18, 2025
Sold
Closed: 08/07/2026
Listing Image for 4299 Lower Honoapiilani Rd 171 1 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 2 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 3 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 4 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 5 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 6 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 7 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 8 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 9 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 10 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 11 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 12 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 13 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 14 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 15 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 16 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 17 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 18 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 19 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 20 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 21 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 22 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 23 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 24 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 25 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 26 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 27 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 28 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 29 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 30 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 31 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 32 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 33 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 34 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 35 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 36 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 37 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 38 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 39 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 40 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 41 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 42 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 43 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 44 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 45 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 46 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 47 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 48 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 49 of 50 Listing Image for 4299 Lower Honoapiilani Rd 171 50 of 50

$2,200,000

↓ $299,000

Sands of Kahana 171

4299 Lower Honoapiilani Rd 171, Napili/Kahana/Honokowai

3 Beds 3 Baths 2,085 SqFt Residential MLS® # 405702 Date Sold: August 7, 2026
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.

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