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: 02/18/2026
Listing Image for 81 S Piki Pl 1 of 50 Listing Image for 81 S Piki Pl 2 of 50 Listing Image for 81 S Piki Pl 3 of 50 Listing Image for 81 S Piki Pl 4 of 50 Listing Image for 81 S Piki Pl 5 of 50 Listing Image for 81 S Piki Pl 6 of 50 Listing Image for 81 S Piki Pl 7 of 50 Listing Image for 81 S Piki Pl 8 of 50 Listing Image for 81 S Piki Pl 9 of 50 Listing Image for 81 S Piki Pl 10 of 50 Listing Image for 81 S Piki Pl 11 of 50 Listing Image for 81 S Piki Pl 12 of 50 Listing Image for 81 S Piki Pl 13 of 50 Listing Image for 81 S Piki Pl 14 of 50 Listing Image for 81 S Piki Pl 15 of 50 Listing Image for 81 S Piki Pl 16 of 50 Listing Image for 81 S Piki Pl 17 of 50 Listing Image for 81 S Piki Pl 18 of 50 Listing Image for 81 S Piki Pl 19 of 50 Listing Image for 81 S Piki Pl 20 of 50 Listing Image for 81 S Piki Pl 21 of 50 Listing Image for 81 S Piki Pl 22 of 50 Listing Image for 81 S Piki Pl 23 of 50 Listing Image for 81 S Piki Pl 24 of 50 Listing Image for 81 S Piki Pl 25 of 50 Listing Image for 81 S Piki Pl 26 of 50 Listing Image for 81 S Piki Pl 27 of 50 Listing Image for 81 S Piki Pl 28 of 50 Listing Image for 81 S Piki Pl 29 of 50 Listing Image for 81 S Piki Pl 30 of 50 Listing Image for 81 S Piki Pl 31 of 50 Listing Image for 81 S Piki Pl 32 of 50 Listing Image for 81 S Piki Pl 33 of 50 Listing Image for 81 S Piki Pl 34 of 50 Listing Image for 81 S Piki Pl 35 of 50 Listing Image for 81 S Piki Pl 36 of 50 Listing Image for 81 S Piki Pl 37 of 50 Listing Image for 81 S Piki Pl 38 of 50 Listing Image for 81 S Piki Pl 39 of 50 Listing Image for 81 S Piki Pl 40 of 50 Listing Image for 81 S Piki Pl 41 of 50 Listing Image for 81 S Piki Pl 42 of 50 Listing Image for 81 S Piki Pl 43 of 50 Listing Image for 81 S Piki Pl 44 of 50 Listing Image for 81 S Piki Pl 45 of 50 Listing Image for 81 S Piki Pl 46 of 50 Listing Image for 81 S Piki Pl 47 of 50 Listing Image for 81 S Piki Pl 48 of 50 Listing Image for 81 S Piki Pl 49 of 50 Listing Image for 81 S Piki Pl 50 of 50

$2,200,000

↓ $450,000

Kaanapali Hillside

81 S Piki Pl, Kaanapali

4 Beds 3.5 Baths 2,512 SqFt Residential MLS® # 406618 Date Sold: February 18, 2026
Sold
Closed: 07/31/2025
Listing Image for Lot 3-e Hana Hwy 1 of 24 Listing Image for Lot 3-e Hana Hwy 2 of 24 Listing Image for Lot 3-e Hana Hwy 3 of 24 Listing Image for Lot 3-e Hana Hwy 4 of 24 Listing Image for Lot 3-e Hana Hwy 5 of 24 Listing Image for Lot 3-e Hana Hwy 6 of 24 Listing Image for Lot 3-e Hana Hwy 7 of 24 Listing Image for Lot 3-e Hana Hwy 8 of 24 Listing Image for Lot 3-e Hana Hwy 9 of 24 Listing Image for Lot 3-e Hana Hwy 10 of 24 Listing Image for Lot 3-e Hana Hwy 11 of 24 Listing Image for Lot 3-e Hana Hwy 12 of 24 Listing Image for Lot 3-e Hana Hwy 13 of 24 Listing Image for Lot 3-e Hana Hwy 14 of 24 Listing Image for Lot 3-e Hana Hwy 15 of 24 Listing Image for Lot 3-e Hana Hwy 16 of 24 Listing Image for Lot 3-e Hana Hwy 17 of 24 Listing Image for Lot 3-e Hana Hwy 18 of 24 Listing Image for Lot 3-e Hana Hwy 19 of 24 Listing Image for Lot 3-e Hana Hwy 20 of 24 Listing Image for Lot 3-e Hana Hwy 21 of 24 Listing Image for Lot 3-e Hana Hwy 22 of 24 Listing Image for Lot 3-e Hana Hwy 23 of 24 Listing Image for Lot 3-e Hana Hwy 24 of 24

$775,000

Hana

Lot 3-e Hana Hwy, Hana

0 Beds 0 Baths 0 SqFt Land MLS® # 404778 Date Sold: July 31, 2025
Sold
Closed: 01/09/2026
Listing Image for 800 S Kihei Rd 504 1 of 50 Listing Image for 800 S Kihei Rd 504 2 of 50 Listing Image for 800 S Kihei Rd 504 3 of 50 Listing Image for 800 S Kihei Rd 504 4 of 50 Listing Image for 800 S Kihei Rd 504 5 of 50 Listing Image for 800 S Kihei Rd 504 6 of 50 Listing Image for 800 S Kihei Rd 504 7 of 50 Listing Image for 800 S Kihei Rd 504 8 of 50 Listing Image for 800 S Kihei Rd 504 9 of 50 Listing Image for 800 S Kihei Rd 504 10 of 50 Listing Image for 800 S Kihei Rd 504 11 of 50 Listing Image for 800 S Kihei Rd 504 12 of 50 Listing Image for 800 S Kihei Rd 504 13 of 50 Listing Image for 800 S Kihei Rd 504 14 of 50 Listing Image for 800 S Kihei Rd 504 15 of 50 Listing Image for 800 S Kihei Rd 504 16 of 50 Listing Image for 800 S Kihei Rd 504 17 of 50 Listing Image for 800 S Kihei Rd 504 18 of 50 Listing Image for 800 S Kihei Rd 504 19 of 50 Listing Image for 800 S Kihei Rd 504 20 of 50 Listing Image for 800 S Kihei Rd 504 21 of 50 Listing Image for 800 S Kihei Rd 504 22 of 50 Listing Image for 800 S Kihei Rd 504 23 of 50 Listing Image for 800 S Kihei Rd 504 24 of 50 Listing Image for 800 S Kihei Rd 504 25 of 50 Listing Image for 800 S Kihei Rd 504 26 of 50 Listing Image for 800 S Kihei Rd 504 27 of 50 Listing Image for 800 S Kihei Rd 504 28 of 50 Listing Image for 800 S Kihei Rd 504 29 of 50 Listing Image for 800 S Kihei Rd 504 30 of 50 Listing Image for 800 S Kihei Rd 504 31 of 50 Listing Image for 800 S Kihei Rd 504 32 of 50 Listing Image for 800 S Kihei Rd 504 33 of 50 Listing Image for 800 S Kihei Rd 504 34 of 50 Listing Image for 800 S Kihei Rd 504 35 of 50 Listing Image for 800 S Kihei Rd 504 36 of 50 Listing Image for 800 S Kihei Rd 504 37 of 50 Listing Image for 800 S Kihei Rd 504 38 of 50 Listing Image for 800 S Kihei Rd 504 39 of 50 Listing Image for 800 S Kihei Rd 504 40 of 50 Listing Image for 800 S Kihei Rd 504 41 of 50 Listing Image for 800 S Kihei Rd 504 42 of 50 Listing Image for 800 S Kihei Rd 504 43 of 50 Listing Image for 800 S Kihei Rd 504 44 of 50 Listing Image for 800 S Kihei Rd 504 45 of 50 Listing Image for 800 S Kihei Rd 504 46 of 50 Listing Image for 800 S Kihei Rd 504 47 of 50 Listing Image for 800 S Kihei Rd 504 48 of 50 Listing Image for 800 S Kihei Rd 504 49 of 50 Listing Image for 800 S Kihei Rd 504 50 of 50

$1,000,000

Koa Lagoon 504

800 S Kihei Rd 504, Kihei

2 Beds 2 Baths 965 SqFt Residential MLS® # 406182 Date Sold: January 9, 2026
Sold
Closed: 06/18/2026
1980 Main St, Wailuku

$1,514,300

↓ $3,685,700

Wailuku

1980 Main St, Wailuku

0 Beds 0 Baths 0 SqFt Commercial Sale MLS® # 401870 Date Sold: June 18, 2026
Sold
Closed: 04/02/2026
Listing Image for 179 Lolowaa Pl 2 1 of 50 Listing Image for 179 Lolowaa Pl 2 2 of 50 Listing Image for 179 Lolowaa Pl 2 3 of 50 Listing Image for 179 Lolowaa Pl 2 4 of 50 Listing Image for 179 Lolowaa Pl 2 5 of 50 Listing Image for 179 Lolowaa Pl 2 6 of 50 Listing Image for 179 Lolowaa Pl 2 7 of 50 Listing Image for 179 Lolowaa Pl 2 8 of 50 Listing Image for 179 Lolowaa Pl 2 9 of 50 Listing Image for 179 Lolowaa Pl 2 10 of 50 Listing Image for 179 Lolowaa Pl 2 11 of 50 Listing Image for 179 Lolowaa Pl 2 12 of 50 Listing Image for 179 Lolowaa Pl 2 13 of 50 Listing Image for 179 Lolowaa Pl 2 14 of 50 Listing Image for 179 Lolowaa Pl 2 15 of 50 Listing Image for 179 Lolowaa Pl 2 16 of 50 Listing Image for 179 Lolowaa Pl 2 17 of 50 Listing Image for 179 Lolowaa Pl 2 18 of 50 Listing Image for 179 Lolowaa Pl 2 19 of 50 Listing Image for 179 Lolowaa Pl 2 20 of 50 Listing Image for 179 Lolowaa Pl 2 21 of 50 Listing Image for 179 Lolowaa Pl 2 22 of 50 Listing Image for 179 Lolowaa Pl 2 23 of 50 Listing Image for 179 Lolowaa Pl 2 24 of 50 Listing Image for 179 Lolowaa Pl 2 25 of 50 Listing Image for 179 Lolowaa Pl 2 26 of 50 Listing Image for 179 Lolowaa Pl 2 27 of 50 Listing Image for 179 Lolowaa Pl 2 28 of 50 Listing Image for 179 Lolowaa Pl 2 29 of 50 Listing Image for 179 Lolowaa Pl 2 30 of 50 Listing Image for 179 Lolowaa Pl 2 31 of 50 Listing Image for 179 Lolowaa Pl 2 32 of 50 Listing Image for 179 Lolowaa Pl 2 33 of 50 Listing Image for 179 Lolowaa Pl 2 34 of 50 Listing Image for 179 Lolowaa Pl 2 35 of 50 Listing Image for 179 Lolowaa Pl 2 36 of 50 Listing Image for 179 Lolowaa Pl 2 37 of 50 Listing Image for 179 Lolowaa Pl 2 38 of 50 Listing Image for 179 Lolowaa Pl 2 39 of 50 Listing Image for 179 Lolowaa Pl 2 40 of 50 Listing Image for 179 Lolowaa Pl 2 41 of 50 Listing Image for 179 Lolowaa Pl 2 42 of 50 Listing Image for 179 Lolowaa Pl 2 43 of 50 Listing Image for 179 Lolowaa Pl 2 44 of 50 Listing Image for 179 Lolowaa Pl 2 45 of 50 Listing Image for 179 Lolowaa Pl 2 46 of 50 Listing Image for 179 Lolowaa Pl 2 47 of 50 Listing Image for 179 Lolowaa Pl 2 48 of 50 Listing Image for 179 Lolowaa Pl 2 49 of 50 Listing Image for 179 Lolowaa Pl 2 50 of 50

$4,150,000

↓ $545,000

Wailea Golf Estates II

179 Lolowaa Pl 2, Wailea/Makena

3 Beds 3.5 Baths 3,330 SqFt Residential MLS® # 406747 Date Sold: April 2, 2026
Sold
Closed: 08/14/2026
Listing Image for 2553 Hihimanu St 113 1 of 45 Listing Image for 2553 Hihimanu St 113 2 of 45 Listing Image for 2553 Hihimanu St 113 3 of 45 Listing Image for 2553 Hihimanu St 113 4 of 45 Listing Image for 2553 Hihimanu St 113 5 of 45 Listing Image for 2553 Hihimanu St 113 6 of 45 Listing Image for 2553 Hihimanu St 113 7 of 45 Listing Image for 2553 Hihimanu St 113 8 of 45 Listing Image for 2553 Hihimanu St 113 9 of 45 Listing Image for 2553 Hihimanu St 113 10 of 45 Listing Image for 2553 Hihimanu St 113 11 of 45 Listing Image for 2553 Hihimanu St 113 12 of 45 Listing Image for 2553 Hihimanu St 113 13 of 45 Listing Image for 2553 Hihimanu St 113 14 of 45 Listing Image for 2553 Hihimanu St 113 15 of 45 Listing Image for 2553 Hihimanu St 113 16 of 45 Listing Image for 2553 Hihimanu St 113 17 of 45 Listing Image for 2553 Hihimanu St 113 18 of 45 Listing Image for 2553 Hihimanu St 113 19 of 45 Listing Image for 2553 Hihimanu St 113 20 of 45 Listing Image for 2553 Hihimanu St 113 21 of 45 Listing Image for 2553 Hihimanu St 113 22 of 45 Listing Image for 2553 Hihimanu St 113 23 of 45 Listing Image for 2553 Hihimanu St 113 24 of 45 Listing Image for 2553 Hihimanu St 113 25 of 45 Listing Image for 2553 Hihimanu St 113 26 of 45 Listing Image for 2553 Hihimanu St 113 27 of 45 Listing Image for 2553 Hihimanu St 113 28 of 45 Listing Image for 2553 Hihimanu St 113 29 of 45 Listing Image for 2553 Hihimanu St 113 30 of 45 Listing Image for 2553 Hihimanu St 113 31 of 45 Listing Image for 2553 Hihimanu St 113 32 of 45 Listing Image for 2553 Hihimanu St 113 33 of 45 Listing Image for 2553 Hihimanu St 113 34 of 45 Listing Image for 2553 Hihimanu St 113 35 of 45 Listing Image for 2553 Hihimanu St 113 36 of 45 Listing Image for 2553 Hihimanu St 113 37 of 45 Listing Image for 2553 Hihimanu St 113 38 of 45 Listing Image for 2553 Hihimanu St 113 39 of 45 Listing Image for 2553 Hihimanu St 113 40 of 45 Listing Image for 2553 Hihimanu St 113 41 of 45 Listing Image for 2553 Hihimanu St 113 42 of 45 Listing Image for 2553 Hihimanu St 113 43 of 45 Listing Image for 2553 Hihimanu St 113 44 of 45 Listing Image for 2553 Hihimanu St 113 45 of 45

$1,675,000

↓ $298,000

Hokulani Golf Villas 113

2553 Hihimanu St 113, Kihei

3 Beds 3 Baths 2,548 SqFt Residential MLS® # 405519 Date Sold: August 14, 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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