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 50 Puu Anoano St 3903 1 of 39 Listing Image for 50 Puu Anoano St 3903 2 of 39 Listing Image for 50 Puu Anoano St 3903 3 of 39 Listing Image for 50 Puu Anoano St 3903 4 of 39 Listing Image for 50 Puu Anoano St 3903 5 of 39 Listing Image for 50 Puu Anoano St 3903 6 of 39 Listing Image for 50 Puu Anoano St 3903 7 of 39 Listing Image for 50 Puu Anoano St 3903 8 of 39 Listing Image for 50 Puu Anoano St 3903 9 of 39 Listing Image for 50 Puu Anoano St 3903 10 of 39 Listing Image for 50 Puu Anoano St 3903 11 of 39 Listing Image for 50 Puu Anoano St 3903 12 of 39 Listing Image for 50 Puu Anoano St 3903 13 of 39 Listing Image for 50 Puu Anoano St 3903 14 of 39 Listing Image for 50 Puu Anoano St 3903 15 of 39 Listing Image for 50 Puu Anoano St 3903 16 of 39 Listing Image for 50 Puu Anoano St 3903 17 of 39 Listing Image for 50 Puu Anoano St 3903 18 of 39 Listing Image for 50 Puu Anoano St 3903 19 of 39 Listing Image for 50 Puu Anoano St 3903 20 of 39 Listing Image for 50 Puu Anoano St 3903 21 of 39 Listing Image for 50 Puu Anoano St 3903 22 of 39 Listing Image for 50 Puu Anoano St 3903 23 of 39 Listing Image for 50 Puu Anoano St 3903 24 of 39 Listing Image for 50 Puu Anoano St 3903 25 of 39 Listing Image for 50 Puu Anoano St 3903 26 of 39 Listing Image for 50 Puu Anoano St 3903 27 of 39 Listing Image for 50 Puu Anoano St 3903 28 of 39 Listing Image for 50 Puu Anoano St 3903 29 of 39 Listing Image for 50 Puu Anoano St 3903 30 of 39 Listing Image for 50 Puu Anoano St 3903 31 of 39 Listing Image for 50 Puu Anoano St 3903 32 of 39 Listing Image for 50 Puu Anoano St 3903 33 of 39 Listing Image for 50 Puu Anoano St 3903 34 of 39 Listing Image for 50 Puu Anoano St 3903 35 of 39 Listing Image for 50 Puu Anoano St 3903 36 of 39 Listing Image for 50 Puu Anoano St 3903 37 of 39 Listing Image for 50 Puu Anoano St 3903 38 of 39 Listing Image for 50 Puu Anoano St 3903 39 of 39

$860,000

↓ $55,000

Masters 3903

50 Puu Anoano St 3903, Kaanapali

1 Bed 1 Bath 901 SqFt Residential MLS® # 409133

Days on Market: 171

Coldwell Banker Island Prop-KP Cell: 808-276-6061

Short Term Rental
Listing Image for 3445 Lower Honoapiilani Rd 839 1 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 2 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 3 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 4 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 5 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 6 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 7 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 8 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 9 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 10 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 11 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 12 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 13 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 14 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 15 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 16 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 17 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 18 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 19 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 20 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 21 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 22 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 23 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 24 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 25 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 26 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 27 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 28 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 29 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 30 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 31 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 32 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 33 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 34 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 35 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 36 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 37 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 38 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 39 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 40 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 41 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 42 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 43 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 44 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 45 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 46 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 47 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 48 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 49 of 50 Listing Image for 3445 Lower Honoapiilani Rd 839 50 of 50

$850,000

Kaanapali Shores 839

3445 Lower Honoapiilani Rd 839, Kaanapali

1 Bed 1 Bath 717 SqFt Residential MLS® # 409126

Days on Market: 172

Keller Williams Realty Maui-Ka Cell: 808-276-8776

Short Term Rental
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$2,950,000

Wailea Elua 2012

3600 Wailea Alanui Dr 2012, Wailea/Makena

1 Bed 2 Baths 1,031 SqFt Residential MLS® # 409117

Days on Market: 173

Coldwell Banker Island Prop(S) Cell: 808-425-3566

Short Term Rental
Listing Image for 5255 Lower Honoapiilani Rd 207 1 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 2 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 3 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 4 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 5 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 6 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 7 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 8 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 9 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 10 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 11 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 12 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 13 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 14 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 15 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 16 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 17 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 18 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 19 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 20 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 21 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 22 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 23 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 24 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 25 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 26 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 27 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 28 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 29 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 30 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 31 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 32 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 33 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 34 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 35 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 36 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 37 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 38 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 39 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 40 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 41 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 42 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 43 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 44 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 45 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 46 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 47 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 48 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 49 of 50 Listing Image for 5255 Lower Honoapiilani Rd 207 50 of 50

$1,150,000

↓ $25,000

Honokeana Cove 207

5255 Lower Honoapiilani Rd 207, Napili/Kahana/Honokowai

1 Bed 1 Bath 517 SqFt Residential MLS® # 409107

Days on Market: 174

Coldwell Banker Island Prop(S) Cell: 808-298-5296

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
Listing Image for 3950 Kalai Waa St Y-202 1 of 44 Listing Image for 3950 Kalai Waa St Y-202 2 of 44 Listing Image for 3950 Kalai Waa St Y-202 3 of 44 Listing Image for 3950 Kalai Waa St Y-202 4 of 44 Listing Image for 3950 Kalai Waa St Y-202 5 of 44 Listing Image for 3950 Kalai Waa St Y-202 6 of 44 Listing Image for 3950 Kalai Waa St Y-202 7 of 44 Listing Image for 3950 Kalai Waa St Y-202 8 of 44 Listing Image for 3950 Kalai Waa St Y-202 9 of 44 Listing Image for 3950 Kalai Waa St Y-202 10 of 44 Listing Image for 3950 Kalai Waa St Y-202 11 of 44 Listing Image for 3950 Kalai Waa St Y-202 12 of 44 Listing Image for 3950 Kalai Waa St Y-202 13 of 44 Listing Image for 3950 Kalai Waa St Y-202 14 of 44 Listing Image for 3950 Kalai Waa St Y-202 15 of 44 Listing Image for 3950 Kalai Waa St Y-202 16 of 44 Listing Image for 3950 Kalai Waa St Y-202 17 of 44 Listing Image for 3950 Kalai Waa St Y-202 18 of 44 Listing Image for 3950 Kalai Waa St Y-202 19 of 44 Listing Image for 3950 Kalai Waa St Y-202 20 of 44 Listing Image for 3950 Kalai Waa St Y-202 21 of 44 Listing Image for 3950 Kalai Waa St Y-202 22 of 44 Listing Image for 3950 Kalai Waa St Y-202 23 of 44 Listing Image for 3950 Kalai Waa St Y-202 24 of 44 Listing Image for 3950 Kalai Waa St Y-202 25 of 44 Listing Image for 3950 Kalai Waa St Y-202 26 of 44 Listing Image for 3950 Kalai Waa St Y-202 27 of 44 Listing Image for 3950 Kalai Waa St Y-202 28 of 44 Listing Image for 3950 Kalai Waa St Y-202 29 of 44 Listing Image for 3950 Kalai Waa St Y-202 30 of 44 Listing Image for 3950 Kalai Waa St Y-202 31 of 44 Listing Image for 3950 Kalai Waa St Y-202 32 of 44 Listing Image for 3950 Kalai Waa St Y-202 33 of 44 Listing Image for 3950 Kalai Waa St Y-202 34 of 44 Listing Image for 3950 Kalai Waa St Y-202 35 of 44 Listing Image for 3950 Kalai Waa St Y-202 36 of 44 Listing Image for 3950 Kalai Waa St Y-202 37 of 44 Listing Image for 3950 Kalai Waa St Y-202 38 of 44 Listing Image for 3950 Kalai Waa St Y-202 39 of 44 Listing Image for 3950 Kalai Waa St Y-202 40 of 44 Listing Image for 3950 Kalai Waa St Y-202 41 of 44 Listing Image for 3950 Kalai Waa St Y-202 42 of 44 Listing Image for 3950 Kalai Waa St Y-202 43 of 44 Listing Image for 3950 Kalai Waa St Y-202 44 of 44

$1,189,000

Wailea Fairway Villas Y-202

3950 Kalai Waa St Y-202, Wailea/Makena

2 Beds 2 Baths 949 SqFt Residential MLS® # 409105

Days on Market: 175

Hawaii Life (W) Cell: 808-870-8668

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

$2,350,000

Kapua Village

32 Piina Pl, Napili/Kahana/Honokowai

3 Beds 3 Baths 1,807 SqFt Residential MLS® # 409097

Days on Market: 176

Corcoran Pacific Properties

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

$4,395,000

↓ $104,995

Kulamalu Hilltop

35 Ohia Lehua Pl, Pukalani

4 Beds 4 Baths 3,192 SqFt Residential MLS® # 409092

Days on Market: 176

Maui Real Estate Advisors LLC 808-875-4444

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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: 06/12/2026
Listing Image for 2560 Kekaa Dr K201 1 of 36 Listing Image for 2560 Kekaa Dr K201 2 of 36 Listing Image for 2560 Kekaa Dr K201 3 of 36 Listing Image for 2560 Kekaa Dr K201 4 of 36 Listing Image for 2560 Kekaa Dr K201 5 of 36 Listing Image for 2560 Kekaa Dr K201 6 of 36 Listing Image for 2560 Kekaa Dr K201 7 of 36 Listing Image for 2560 Kekaa Dr K201 8 of 36 Listing Image for 2560 Kekaa Dr K201 9 of 36 Listing Image for 2560 Kekaa Dr K201 10 of 36 Listing Image for 2560 Kekaa Dr K201 11 of 36 Listing Image for 2560 Kekaa Dr K201 12 of 36 Listing Image for 2560 Kekaa Dr K201 13 of 36 Listing Image for 2560 Kekaa Dr K201 14 of 36 Listing Image for 2560 Kekaa Dr K201 15 of 36 Listing Image for 2560 Kekaa Dr K201 16 of 36 Listing Image for 2560 Kekaa Dr K201 17 of 36 Listing Image for 2560 Kekaa Dr K201 18 of 36 Listing Image for 2560 Kekaa Dr K201 19 of 36 Listing Image for 2560 Kekaa Dr K201 20 of 36 Listing Image for 2560 Kekaa Dr K201 21 of 36 Listing Image for 2560 Kekaa Dr K201 22 of 36 Listing Image for 2560 Kekaa Dr K201 23 of 36 Listing Image for 2560 Kekaa Dr K201 24 of 36 Listing Image for 2560 Kekaa Dr K201 25 of 36 Listing Image for 2560 Kekaa Dr K201 26 of 36 Listing Image for 2560 Kekaa Dr K201 27 of 36 Listing Image for 2560 Kekaa Dr K201 28 of 36 Listing Image for 2560 Kekaa Dr K201 29 of 36 Listing Image for 2560 Kekaa Dr K201 30 of 36 Listing Image for 2560 Kekaa Dr K201 31 of 36 Listing Image for 2560 Kekaa Dr K201 32 of 36 Listing Image for 2560 Kekaa Dr K201 33 of 36 Listing Image for 2560 Kekaa Dr K201 34 of 36 Listing Image for 2560 Kekaa Dr K201 35 of 36 Listing Image for 2560 Kekaa Dr K201 36 of 36

$925,000

↓ $150,000

Kaanapali Royal K201

2560 Kekaa Dr K201, Kaanapali

2 Beds 2 Baths 1,534 SqFt Residential MLS® # 407920 Date Sold: June 12, 2026
Sold
Closed: 04/23/2026
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$875,000

↓ $35,000

Milo Court at Kehalani 91

120 Eulu St 91, Wailuku

3 Beds 2.5 Baths 1,465 SqFt Residential MLS® # 407918 Date Sold: April 23, 2026
Sold
Closed: 03/12/2026
Listing Image for 2481 Kaanapali Pkwy 565 1 of 38 Listing Image for 2481 Kaanapali Pkwy 565 2 of 38 Listing Image for 2481 Kaanapali Pkwy 565 3 of 38 Listing Image for 2481 Kaanapali Pkwy 565 4 of 38 Listing Image for 2481 Kaanapali Pkwy 565 5 of 38 Listing Image for 2481 Kaanapali Pkwy 565 6 of 38 Listing Image for 2481 Kaanapali Pkwy 565 7 of 38 Listing Image for 2481 Kaanapali Pkwy 565 8 of 38 Listing Image for 2481 Kaanapali Pkwy 565 9 of 38 Listing Image for 2481 Kaanapali Pkwy 565 10 of 38 Listing Image for 2481 Kaanapali Pkwy 565 11 of 38 Listing Image for 2481 Kaanapali Pkwy 565 12 of 38 Listing Image for 2481 Kaanapali Pkwy 565 13 of 38 Listing Image for 2481 Kaanapali Pkwy 565 14 of 38 Listing Image for 2481 Kaanapali Pkwy 565 15 of 38 Listing Image for 2481 Kaanapali Pkwy 565 16 of 38 Listing Image for 2481 Kaanapali Pkwy 565 17 of 38 Listing Image for 2481 Kaanapali Pkwy 565 18 of 38 Listing Image for 2481 Kaanapali Pkwy 565 19 of 38 Listing Image for 2481 Kaanapali Pkwy 565 20 of 38 Listing Image for 2481 Kaanapali Pkwy 565 21 of 38 Listing Image for 2481 Kaanapali Pkwy 565 22 of 38 Listing Image for 2481 Kaanapali Pkwy 565 23 of 38 Listing Image for 2481 Kaanapali Pkwy 565 24 of 38 Listing Image for 2481 Kaanapali Pkwy 565 25 of 38 Listing Image for 2481 Kaanapali Pkwy 565 26 of 38 Listing Image for 2481 Kaanapali Pkwy 565 27 of 38 Listing Image for 2481 Kaanapali Pkwy 565 28 of 38 Listing Image for 2481 Kaanapali Pkwy 565 29 of 38 Listing Image for 2481 Kaanapali Pkwy 565 30 of 38 Listing Image for 2481 Kaanapali Pkwy 565 31 of 38 Listing Image for 2481 Kaanapali Pkwy 565 32 of 38 Listing Image for 2481 Kaanapali Pkwy 565 33 of 38 Listing Image for 2481 Kaanapali Pkwy 565 34 of 38 Listing Image for 2481 Kaanapali Pkwy 565 35 of 38 Listing Image for 2481 Kaanapali Pkwy 565 36 of 38 Listing Image for 2481 Kaanapali Pkwy 565 37 of 38 Listing Image for 2481 Kaanapali Pkwy 565 38 of 38

$940,000

↓ $59,000

Whaler 565

2481 Kaanapali Pkwy 565, Kaanapali

0 Beds 1 Bath 542 SqFt Residential MLS® # 407913 Date Sold: March 12, 2026
Sold
Closed: 02/23/2026
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$3,276,000

Wailea Point 2003

4000 Wailea Alanui Dr 2003, Wailea/Makena

2 Beds 3 Baths 1,584 SqFt Residential MLS® # 407909 Date Sold: February 23, 2026
Sold
Closed: 05/05/2026
Listing Image for 79 Lauie Dr 1 of 25 Listing Image for 79 Lauie Dr 2 of 25 Listing Image for 79 Lauie Dr 3 of 25 Listing Image for 79 Lauie Dr 4 of 25 Listing Image for 79 Lauie Dr 5 of 25 Listing Image for 79 Lauie Dr 6 of 25 Listing Image for 79 Lauie Dr 7 of 25 Listing Image for 79 Lauie Dr 8 of 25 Listing Image for 79 Lauie Dr 9 of 25 Listing Image for 79 Lauie Dr 10 of 25 Listing Image for 79 Lauie Dr 11 of 25 Listing Image for 79 Lauie Dr 12 of 25 Listing Image for 79 Lauie Dr 13 of 25 Listing Image for 79 Lauie Dr 14 of 25 Listing Image for 79 Lauie Dr 15 of 25 Listing Image for 79 Lauie Dr 16 of 25 Listing Image for 79 Lauie Dr 17 of 25 Listing Image for 79 Lauie Dr 18 of 25 Listing Image for 79 Lauie Dr 19 of 25 Listing Image for 79 Lauie Dr 20 of 25 Listing Image for 79 Lauie Dr 21 of 25 Listing Image for 79 Lauie Dr 22 of 25 Listing Image for 79 Lauie Dr 23 of 25 Listing Image for 79 Lauie Dr 24 of 25 Listing Image for 79 Lauie Dr 25 of 25

$836,276

Hawaiian Homelands

79 Lauie Dr, Kula/Ulupalakua/Kanaio

4 Beds 2 Baths 1,248 SqFt Residential MLS® # 407906 Date Sold: May 5, 2026
Sold
Closed: 11/26/2025
22 Maiaku St 145, Makawao/Olinda/Haliimaile

$1,515,000

Hokuula

22 Maiaku St 145, Makawao/Olinda/Haliimaile

4 Beds 3 Baths 1,960 SqFt Residential MLS® # 407904 Date Sold: November 26, 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.

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