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 500 Bay Dr 12b1-2 1 of 50 Listing Image for 500 Bay Dr 12b1-2 2 of 50 Listing Image for 500 Bay Dr 12b1-2 3 of 50 Listing Image for 500 Bay Dr 12b1-2 4 of 50 Listing Image for 500 Bay Dr 12b1-2 5 of 50 Listing Image for 500 Bay Dr 12b1-2 6 of 50 Listing Image for 500 Bay Dr 12b1-2 7 of 50 Listing Image for 500 Bay Dr 12b1-2 8 of 50 Listing Image for 500 Bay Dr 12b1-2 9 of 50 Listing Image for 500 Bay Dr 12b1-2 10 of 50 Listing Image for 500 Bay Dr 12b1-2 11 of 50 Listing Image for 500 Bay Dr 12b1-2 12 of 50 Listing Image for 500 Bay Dr 12b1-2 13 of 50 Listing Image for 500 Bay Dr 12b1-2 14 of 50 Listing Image for 500 Bay Dr 12b1-2 15 of 50 Listing Image for 500 Bay Dr 12b1-2 16 of 50 Listing Image for 500 Bay Dr 12b1-2 17 of 50 Listing Image for 500 Bay Dr 12b1-2 18 of 50 Listing Image for 500 Bay Dr 12b1-2 19 of 50 Listing Image for 500 Bay Dr 12b1-2 20 of 50 Listing Image for 500 Bay Dr 12b1-2 21 of 50 Listing Image for 500 Bay Dr 12b1-2 22 of 50 Listing Image for 500 Bay Dr 12b1-2 23 of 50 Listing Image for 500 Bay Dr 12b1-2 24 of 50 Listing Image for 500 Bay Dr 12b1-2 25 of 50 Listing Image for 500 Bay Dr 12b1-2 26 of 50 Listing Image for 500 Bay Dr 12b1-2 27 of 50 Listing Image for 500 Bay Dr 12b1-2 28 of 50 Listing Image for 500 Bay Dr 12b1-2 29 of 50 Listing Image for 500 Bay Dr 12b1-2 30 of 50 Listing Image for 500 Bay Dr 12b1-2 31 of 50 Listing Image for 500 Bay Dr 12b1-2 32 of 50 Listing Image for 500 Bay Dr 12b1-2 33 of 50 Listing Image for 500 Bay Dr 12b1-2 34 of 50 Listing Image for 500 Bay Dr 12b1-2 35 of 50 Listing Image for 500 Bay Dr 12b1-2 36 of 50 Listing Image for 500 Bay Dr 12b1-2 37 of 50 Listing Image for 500 Bay Dr 12b1-2 38 of 50 Listing Image for 500 Bay Dr 12b1-2 39 of 50 Listing Image for 500 Bay Dr 12b1-2 40 of 50 Listing Image for 500 Bay Dr 12b1-2 41 of 50 Listing Image for 500 Bay Dr 12b1-2 42 of 50 Listing Image for 500 Bay Dr 12b1-2 43 of 50 Listing Image for 500 Bay Dr 12b1-2 44 of 50 Listing Image for 500 Bay Dr 12b1-2 45 of 50 Listing Image for 500 Bay Dr 12b1-2 46 of 50 Listing Image for 500 Bay Dr 12b1-2 47 of 50 Listing Image for 500 Bay Dr 12b1-2 48 of 50 Listing Image for 500 Bay Dr 12b1-2 49 of 50 Listing Image for 500 Bay Dr 12b1-2 50 of 50

$2,600,000

↓ $50,000

Kapalua Bay Villas 12B1-2

500 Bay Dr 12b1-2, Kapalua

2 Beds 3 Baths 1,569 SqFt Residential MLS® # 409427

Days on Market: 141

Keller Williams Realty Maui-L Cell: 808-385-2918

In Escrow
Listing Image for 2130 Kauhikoa Rd Unit B 1 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 2 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 3 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 4 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 5 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 6 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 7 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 8 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 9 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 10 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 11 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 12 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 13 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 14 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 15 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 16 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 17 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 18 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 19 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 20 of 21 Listing Image for 2130 Kauhikoa Rd Unit B 21 of 21

$890,000

Haiku

2130 Kauhikoa Rd Unit B, Haiku

2 Beds 1 Bath 500 SqFt Residential MLS® # 409416

Days on Market: 144

Hawaii Life (W) Cell: 808-283-4688

Listing Image for 337 Laniuma Pl 1 of 34 Listing Image for 337 Laniuma Pl 2 of 34 Listing Image for 337 Laniuma Pl 3 of 34 Listing Image for 337 Laniuma Pl 4 of 34 Listing Image for 337 Laniuma Pl 5 of 34 Listing Image for 337 Laniuma Pl 6 of 34 Listing Image for 337 Laniuma Pl 7 of 34 Listing Image for 337 Laniuma Pl 8 of 34 Listing Image for 337 Laniuma Pl 9 of 34 Listing Image for 337 Laniuma Pl 10 of 34 Listing Image for 337 Laniuma Pl 11 of 34 Listing Image for 337 Laniuma Pl 12 of 34 Listing Image for 337 Laniuma Pl 13 of 34 Listing Image for 337 Laniuma Pl 14 of 34 Listing Image for 337 Laniuma Pl 15 of 34 Listing Image for 337 Laniuma Pl 16 of 34 Listing Image for 337 Laniuma Pl 17 of 34 Listing Image for 337 Laniuma Pl 18 of 34 Listing Image for 337 Laniuma Pl 19 of 34 Listing Image for 337 Laniuma Pl 20 of 34 Listing Image for 337 Laniuma Pl 21 of 34 Listing Image for 337 Laniuma Pl 22 of 34 Listing Image for 337 Laniuma Pl 23 of 34 Listing Image for 337 Laniuma Pl 24 of 34 Listing Image for 337 Laniuma Pl 25 of 34 Listing Image for 337 Laniuma Pl 26 of 34 Listing Image for 337 Laniuma Pl 27 of 34 Listing Image for 337 Laniuma Pl 28 of 34 Listing Image for 337 Laniuma Pl 29 of 34 Listing Image for 337 Laniuma Pl 30 of 34 Listing Image for 337 Laniuma Pl 31 of 34 Listing Image for 337 Laniuma Pl 32 of 34 Listing Image for 337 Laniuma Pl 33 of 34 Listing Image for 337 Laniuma Pl 34 of 34

$1,385,000

↓ $14,500

Anuhea

337 Laniuma Pl, Wailuku

3 Beds 2 Baths 1,524 SqFt Residential MLS® # 409408

Days on Market: 144

Hawaiian Style Realty LLC

Listing Image for 654 Kaupakalua Rd 1 of 41 Listing Image for 654 Kaupakalua Rd 2 of 41 Listing Image for 654 Kaupakalua Rd 3 of 41 Listing Image for 654 Kaupakalua Rd 4 of 41 Listing Image for 654 Kaupakalua Rd 5 of 41 Listing Image for 654 Kaupakalua Rd 6 of 41 Listing Image for 654 Kaupakalua Rd 7 of 41 Listing Image for 654 Kaupakalua Rd 8 of 41 Listing Image for 654 Kaupakalua Rd 9 of 41 Listing Image for 654 Kaupakalua Rd 10 of 41 Listing Image for 654 Kaupakalua Rd 11 of 41 Listing Image for 654 Kaupakalua Rd 12 of 41 Listing Image for 654 Kaupakalua Rd 13 of 41 Listing Image for 654 Kaupakalua Rd 14 of 41 Listing Image for 654 Kaupakalua Rd 15 of 41 Listing Image for 654 Kaupakalua Rd 16 of 41 Listing Image for 654 Kaupakalua Rd 17 of 41 Listing Image for 654 Kaupakalua Rd 18 of 41 Listing Image for 654 Kaupakalua Rd 19 of 41 Listing Image for 654 Kaupakalua Rd 20 of 41 Listing Image for 654 Kaupakalua Rd 21 of 41 Listing Image for 654 Kaupakalua Rd 22 of 41 Listing Image for 654 Kaupakalua Rd 23 of 41 Listing Image for 654 Kaupakalua Rd 24 of 41 Listing Image for 654 Kaupakalua Rd 25 of 41 Listing Image for 654 Kaupakalua Rd 26 of 41 Listing Image for 654 Kaupakalua Rd 27 of 41 Listing Image for 654 Kaupakalua Rd 28 of 41 Listing Image for 654 Kaupakalua Rd 29 of 41 Listing Image for 654 Kaupakalua Rd 30 of 41 Listing Image for 654 Kaupakalua Rd 31 of 41 Listing Image for 654 Kaupakalua Rd 32 of 41 Listing Image for 654 Kaupakalua Rd 33 of 41 Listing Image for 654 Kaupakalua Rd 34 of 41 Listing Image for 654 Kaupakalua Rd 35 of 41 Listing Image for 654 Kaupakalua Rd 36 of 41 Listing Image for 654 Kaupakalua Rd 37 of 41 Listing Image for 654 Kaupakalua Rd 38 of 41 Listing Image for 654 Kaupakalua Rd 39 of 41 Listing Image for 654 Kaupakalua Rd 40 of 41 Listing Image for 654 Kaupakalua Rd 41 of 41

$3,999,000

Haiku

654 Kaupakalua Rd, Haiku

2 Beds 1 Bath 998 SqFt Residential MLS® # 409398

Days on Market: 144

Compass-W

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 500 Kapalua Dr 23v1 1 of 50 Listing Image for 500 Kapalua Dr 23v1 2 of 50 Listing Image for 500 Kapalua Dr 23v1 3 of 50 Listing Image for 500 Kapalua Dr 23v1 4 of 50 Listing Image for 500 Kapalua Dr 23v1 5 of 50 Listing Image for 500 Kapalua Dr 23v1 6 of 50 Listing Image for 500 Kapalua Dr 23v1 7 of 50 Listing Image for 500 Kapalua Dr 23v1 8 of 50 Listing Image for 500 Kapalua Dr 23v1 9 of 50 Listing Image for 500 Kapalua Dr 23v1 10 of 50 Listing Image for 500 Kapalua Dr 23v1 11 of 50 Listing Image for 500 Kapalua Dr 23v1 12 of 50 Listing Image for 500 Kapalua Dr 23v1 13 of 50 Listing Image for 500 Kapalua Dr 23v1 14 of 50 Listing Image for 500 Kapalua Dr 23v1 15 of 50 Listing Image for 500 Kapalua Dr 23v1 16 of 50 Listing Image for 500 Kapalua Dr 23v1 17 of 50 Listing Image for 500 Kapalua Dr 23v1 18 of 50 Listing Image for 500 Kapalua Dr 23v1 19 of 50 Listing Image for 500 Kapalua Dr 23v1 20 of 50 Listing Image for 500 Kapalua Dr 23v1 21 of 50 Listing Image for 500 Kapalua Dr 23v1 22 of 50 Listing Image for 500 Kapalua Dr 23v1 23 of 50 Listing Image for 500 Kapalua Dr 23v1 24 of 50 Listing Image for 500 Kapalua Dr 23v1 25 of 50 Listing Image for 500 Kapalua Dr 23v1 26 of 50 Listing Image for 500 Kapalua Dr 23v1 27 of 50 Listing Image for 500 Kapalua Dr 23v1 28 of 50 Listing Image for 500 Kapalua Dr 23v1 29 of 50 Listing Image for 500 Kapalua Dr 23v1 30 of 50 Listing Image for 500 Kapalua Dr 23v1 31 of 50 Listing Image for 500 Kapalua Dr 23v1 32 of 50 Listing Image for 500 Kapalua Dr 23v1 33 of 50 Listing Image for 500 Kapalua Dr 23v1 34 of 50 Listing Image for 500 Kapalua Dr 23v1 35 of 50 Listing Image for 500 Kapalua Dr 23v1 36 of 50 Listing Image for 500 Kapalua Dr 23v1 37 of 50 Listing Image for 500 Kapalua Dr 23v1 38 of 50 Listing Image for 500 Kapalua Dr 23v1 39 of 50 Listing Image for 500 Kapalua Dr 23v1 40 of 50 Listing Image for 500 Kapalua Dr 23v1 41 of 50 Listing Image for 500 Kapalua Dr 23v1 42 of 50 Listing Image for 500 Kapalua Dr 23v1 43 of 50 Listing Image for 500 Kapalua Dr 23v1 44 of 50 Listing Image for 500 Kapalua Dr 23v1 45 of 50 Listing Image for 500 Kapalua Dr 23v1 46 of 50 Listing Image for 500 Kapalua Dr 23v1 47 of 50 Listing Image for 500 Kapalua Dr 23v1 48 of 50 Listing Image for 500 Kapalua Dr 23v1 49 of 50 Listing Image for 500 Kapalua Dr 23v1 50 of 50

$1,690,000

Kapalua Golf Villas 23V1

500 Kapalua Dr 23v1, Kapalua

1 Bed 2 Baths 899 SqFt Residential MLS® # 409397

Days on Market: 144

Platinum Properties Hawaii,LLC

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

$3,950,000

↓ $345,000

Kapalua Ironwoods 81

81 Ironwood Ln 81, Kapalua

3 Beds 4 Baths 2,400 SqFt Residential MLS® # 409395

Days on Market: 144

Keller Williams Realty Maui-L Cell: 808-870-7736

Listing Image for 4000 Wailea Alanui Dr 2101 1 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 2 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 3 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 4 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 5 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 6 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 7 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 8 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 9 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 10 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 11 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 12 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 13 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 14 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 15 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 16 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 17 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 18 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 19 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 20 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 21 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 22 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 23 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 24 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 25 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 26 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 27 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 28 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 29 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 30 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 31 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 32 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 33 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 34 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 35 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 36 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 37 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 38 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 39 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 40 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 41 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 42 of 43 Listing Image for 4000 Wailea Alanui Dr 2101 43 of 43

$3,300,000

Wailea Point 2101

4000 Wailea Alanui Dr 2101, Wailea/Makena

2 Beds 3 Baths 1,584 SqFt Residential MLS® # 409393

Days on Market: 144

Wailea Point Realty, Inc. realty@waileapoint.com

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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: 06/03/2026
Listing Image for 500 Bay Dr 23b3 1 of 50 Listing Image for 500 Bay Dr 23b3 2 of 50 Listing Image for 500 Bay Dr 23b3 3 of 50 Listing Image for 500 Bay Dr 23b3 4 of 50 Listing Image for 500 Bay Dr 23b3 5 of 50 Listing Image for 500 Bay Dr 23b3 6 of 50 Listing Image for 500 Bay Dr 23b3 7 of 50 Listing Image for 500 Bay Dr 23b3 8 of 50 Listing Image for 500 Bay Dr 23b3 9 of 50 Listing Image for 500 Bay Dr 23b3 10 of 50 Listing Image for 500 Bay Dr 23b3 11 of 50 Listing Image for 500 Bay Dr 23b3 12 of 50 Listing Image for 500 Bay Dr 23b3 13 of 50 Listing Image for 500 Bay Dr 23b3 14 of 50 Listing Image for 500 Bay Dr 23b3 15 of 50 Listing Image for 500 Bay Dr 23b3 16 of 50 Listing Image for 500 Bay Dr 23b3 17 of 50 Listing Image for 500 Bay Dr 23b3 18 of 50 Listing Image for 500 Bay Dr 23b3 19 of 50 Listing Image for 500 Bay Dr 23b3 20 of 50 Listing Image for 500 Bay Dr 23b3 21 of 50 Listing Image for 500 Bay Dr 23b3 22 of 50 Listing Image for 500 Bay Dr 23b3 23 of 50 Listing Image for 500 Bay Dr 23b3 24 of 50 Listing Image for 500 Bay Dr 23b3 25 of 50 Listing Image for 500 Bay Dr 23b3 26 of 50 Listing Image for 500 Bay Dr 23b3 27 of 50 Listing Image for 500 Bay Dr 23b3 28 of 50 Listing Image for 500 Bay Dr 23b3 29 of 50 Listing Image for 500 Bay Dr 23b3 30 of 50 Listing Image for 500 Bay Dr 23b3 31 of 50 Listing Image for 500 Bay Dr 23b3 32 of 50 Listing Image for 500 Bay Dr 23b3 33 of 50 Listing Image for 500 Bay Dr 23b3 34 of 50 Listing Image for 500 Bay Dr 23b3 35 of 50 Listing Image for 500 Bay Dr 23b3 36 of 50 Listing Image for 500 Bay Dr 23b3 37 of 50 Listing Image for 500 Bay Dr 23b3 38 of 50 Listing Image for 500 Bay Dr 23b3 39 of 50 Listing Image for 500 Bay Dr 23b3 40 of 50 Listing Image for 500 Bay Dr 23b3 41 of 50 Listing Image for 500 Bay Dr 23b3 42 of 50 Listing Image for 500 Bay Dr 23b3 43 of 50 Listing Image for 500 Bay Dr 23b3 44 of 50 Listing Image for 500 Bay Dr 23b3 45 of 50 Listing Image for 500 Bay Dr 23b3 46 of 50 Listing Image for 500 Bay Dr 23b3 47 of 50 Listing Image for 500 Bay Dr 23b3 48 of 50 Listing Image for 500 Bay Dr 23b3 49 of 50 Listing Image for 500 Bay Dr 23b3 50 of 50

$2,925,000

Kapalua Bay Villas 23B3

500 Bay Dr 23b3, Kapalua

2 Beds 3 Baths 1,503 SqFt Residential MLS® # 408142 Date Sold: June 3, 2026
Sold
Closed: 02/06/2026
Listing Image for 300 Mehana Rd Unit B 1 of 49 Listing Image for 300 Mehana Rd Unit B 2 of 49 Listing Image for 300 Mehana Rd Unit B 3 of 49 Listing Image for 300 Mehana Rd Unit B 4 of 49 Listing Image for 300 Mehana Rd Unit B 5 of 49 Listing Image for 300 Mehana Rd Unit B 6 of 49 Listing Image for 300 Mehana Rd Unit B 7 of 49 Listing Image for 300 Mehana Rd Unit B 8 of 49 Listing Image for 300 Mehana Rd Unit B 9 of 49 Listing Image for 300 Mehana Rd Unit B 10 of 49 Listing Image for 300 Mehana Rd Unit B 11 of 49 Listing Image for 300 Mehana Rd Unit B 12 of 49 Listing Image for 300 Mehana Rd Unit B 13 of 49 Listing Image for 300 Mehana Rd Unit B 14 of 49 Listing Image for 300 Mehana Rd Unit B 15 of 49 Listing Image for 300 Mehana Rd Unit B 16 of 49 Listing Image for 300 Mehana Rd Unit B 17 of 49 Listing Image for 300 Mehana Rd Unit B 18 of 49 Listing Image for 300 Mehana Rd Unit B 19 of 49 Listing Image for 300 Mehana Rd Unit B 20 of 49 Listing Image for 300 Mehana Rd Unit B 21 of 49 Listing Image for 300 Mehana Rd Unit B 22 of 49 Listing Image for 300 Mehana Rd Unit B 23 of 49 Listing Image for 300 Mehana Rd Unit B 24 of 49 Listing Image for 300 Mehana Rd Unit B 25 of 49 Listing Image for 300 Mehana Rd Unit B 26 of 49 Listing Image for 300 Mehana Rd Unit B 27 of 49 Listing Image for 300 Mehana Rd Unit B 28 of 49 Listing Image for 300 Mehana Rd Unit B 29 of 49 Listing Image for 300 Mehana Rd Unit B 30 of 49 Listing Image for 300 Mehana Rd Unit B 31 of 49 Listing Image for 300 Mehana Rd Unit B 32 of 49 Listing Image for 300 Mehana Rd Unit B 33 of 49 Listing Image for 300 Mehana Rd Unit B 34 of 49 Listing Image for 300 Mehana Rd Unit B 35 of 49 Listing Image for 300 Mehana Rd Unit B 36 of 49 Listing Image for 300 Mehana Rd Unit B 37 of 49 Listing Image for 300 Mehana Rd Unit B 38 of 49 Listing Image for 300 Mehana Rd Unit B 39 of 49 Listing Image for 300 Mehana Rd Unit B 40 of 49 Listing Image for 300 Mehana Rd Unit B 41 of 49 Listing Image for 300 Mehana Rd Unit B 42 of 49 Listing Image for 300 Mehana Rd Unit B 43 of 49 Listing Image for 300 Mehana Rd Unit B 44 of 49 Listing Image for 300 Mehana Rd Unit B 45 of 49 Listing Image for 300 Mehana Rd Unit B 46 of 49 Listing Image for 300 Mehana Rd Unit B 47 of 49 Listing Image for 300 Mehana Rd Unit B 48 of 49 Listing Image for 300 Mehana Rd Unit B 49 of 49

$1,282,000

Haiku

300 Mehana Rd Unit B, Haiku

0 Beds 0 Baths 0 SqFt Land MLS® # 408141 Date Sold: February 6, 2026
Sold
Closed: 03/31/2026
Listing Image for 3445 Lower Honoapiilani Rd 304 1 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 2 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 3 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 4 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 5 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 6 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 7 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 8 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 9 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 10 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 11 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 12 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 13 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 14 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 15 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 16 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 17 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 18 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 19 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 20 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 21 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 22 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 23 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 24 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 25 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 26 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 27 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 28 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 29 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 30 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 31 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 32 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 33 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 34 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 35 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 36 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 37 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 38 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 39 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 40 of 41 Listing Image for 3445 Lower Honoapiilani Rd 304 41 of 41

$1,053,750

Kaanapali Shores 304

3445 Lower Honoapiilani Rd 304, Kaanapali

2 Beds 2 Baths 988 SqFt Residential MLS® # 408139 Date Sold: March 31, 2026
Sold
Closed: 12/16/2025
938 S Kihei Rd 334, Kihei

$950,000

Kauhale Makai 334

938 S Kihei Rd 334, Kihei

2 Beds 2 Baths 975 SqFt Residential MLS® # 408137 Date Sold: December 16, 2025
Sold
Closed: 04/27/2026
Listing Image for 3387 Kuaua Pl 1 of 50 Listing Image for 3387 Kuaua Pl 2 of 50 Listing Image for 3387 Kuaua Pl 3 of 50 Listing Image for 3387 Kuaua Pl 4 of 50 Listing Image for 3387 Kuaua Pl 5 of 50 Listing Image for 3387 Kuaua Pl 6 of 50 Listing Image for 3387 Kuaua Pl 7 of 50 Listing Image for 3387 Kuaua Pl 8 of 50 Listing Image for 3387 Kuaua Pl 9 of 50 Listing Image for 3387 Kuaua Pl 10 of 50 Listing Image for 3387 Kuaua Pl 11 of 50 Listing Image for 3387 Kuaua Pl 12 of 50 Listing Image for 3387 Kuaua Pl 13 of 50 Listing Image for 3387 Kuaua Pl 14 of 50 Listing Image for 3387 Kuaua Pl 15 of 50 Listing Image for 3387 Kuaua Pl 16 of 50 Listing Image for 3387 Kuaua Pl 17 of 50 Listing Image for 3387 Kuaua Pl 18 of 50 Listing Image for 3387 Kuaua Pl 19 of 50 Listing Image for 3387 Kuaua Pl 20 of 50 Listing Image for 3387 Kuaua Pl 21 of 50 Listing Image for 3387 Kuaua Pl 22 of 50 Listing Image for 3387 Kuaua Pl 23 of 50 Listing Image for 3387 Kuaua Pl 24 of 50 Listing Image for 3387 Kuaua Pl 25 of 50 Listing Image for 3387 Kuaua Pl 26 of 50 Listing Image for 3387 Kuaua Pl 27 of 50 Listing Image for 3387 Kuaua Pl 28 of 50 Listing Image for 3387 Kuaua Pl 29 of 50 Listing Image for 3387 Kuaua Pl 30 of 50 Listing Image for 3387 Kuaua Pl 31 of 50 Listing Image for 3387 Kuaua Pl 32 of 50 Listing Image for 3387 Kuaua Pl 33 of 50 Listing Image for 3387 Kuaua Pl 34 of 50 Listing Image for 3387 Kuaua Pl 35 of 50 Listing Image for 3387 Kuaua Pl 36 of 50 Listing Image for 3387 Kuaua Pl 37 of 50 Listing Image for 3387 Kuaua Pl 38 of 50 Listing Image for 3387 Kuaua Pl 39 of 50 Listing Image for 3387 Kuaua Pl 40 of 50 Listing Image for 3387 Kuaua Pl 41 of 50 Listing Image for 3387 Kuaua Pl 42 of 50 Listing Image for 3387 Kuaua Pl 43 of 50 Listing Image for 3387 Kuaua Pl 44 of 50 Listing Image for 3387 Kuaua Pl 45 of 50 Listing Image for 3387 Kuaua Pl 46 of 50 Listing Image for 3387 Kuaua Pl 47 of 50 Listing Image for 3387 Kuaua Pl 48 of 50 Listing Image for 3387 Kuaua Pl 49 of 50 Listing Image for 3387 Kuaua Pl 50 of 50

$3,850,000

Maui Meadows

3387 Kuaua Pl, Maui Meadows

3 Beds 2.5 Baths 3,146 SqFt Residential MLS® # 408127 Date Sold: April 27, 2026
Sold
Closed: 04/20/2026
Listing Image for 235 Keonekai Rd 1 of 50 Listing Image for 235 Keonekai Rd 2 of 50 Listing Image for 235 Keonekai Rd 3 of 50 Listing Image for 235 Keonekai Rd 4 of 50 Listing Image for 235 Keonekai Rd 5 of 50 Listing Image for 235 Keonekai Rd 6 of 50 Listing Image for 235 Keonekai Rd 7 of 50 Listing Image for 235 Keonekai Rd 8 of 50 Listing Image for 235 Keonekai Rd 9 of 50 Listing Image for 235 Keonekai Rd 10 of 50 Listing Image for 235 Keonekai Rd 11 of 50 Listing Image for 235 Keonekai Rd 12 of 50 Listing Image for 235 Keonekai Rd 13 of 50 Listing Image for 235 Keonekai Rd 14 of 50 Listing Image for 235 Keonekai Rd 15 of 50 Listing Image for 235 Keonekai Rd 16 of 50 Listing Image for 235 Keonekai Rd 17 of 50 Listing Image for 235 Keonekai Rd 18 of 50 Listing Image for 235 Keonekai Rd 19 of 50 Listing Image for 235 Keonekai Rd 20 of 50 Listing Image for 235 Keonekai Rd 21 of 50 Listing Image for 235 Keonekai Rd 22 of 50 Listing Image for 235 Keonekai Rd 23 of 50 Listing Image for 235 Keonekai Rd 24 of 50 Listing Image for 235 Keonekai Rd 25 of 50 Listing Image for 235 Keonekai Rd 26 of 50 Listing Image for 235 Keonekai Rd 27 of 50 Listing Image for 235 Keonekai Rd 28 of 50 Listing Image for 235 Keonekai Rd 29 of 50 Listing Image for 235 Keonekai Rd 30 of 50 Listing Image for 235 Keonekai Rd 31 of 50 Listing Image for 235 Keonekai Rd 32 of 50 Listing Image for 235 Keonekai Rd 33 of 50 Listing Image for 235 Keonekai Rd 34 of 50 Listing Image for 235 Keonekai Rd 35 of 50 Listing Image for 235 Keonekai Rd 36 of 50 Listing Image for 235 Keonekai Rd 37 of 50 Listing Image for 235 Keonekai Rd 38 of 50 Listing Image for 235 Keonekai Rd 39 of 50 Listing Image for 235 Keonekai Rd 40 of 50 Listing Image for 235 Keonekai Rd 41 of 50 Listing Image for 235 Keonekai Rd 42 of 50 Listing Image for 235 Keonekai Rd 43 of 50 Listing Image for 235 Keonekai Rd 44 of 50 Listing Image for 235 Keonekai Rd 45 of 50 Listing Image for 235 Keonekai Rd 46 of 50 Listing Image for 235 Keonekai Rd 47 of 50 Listing Image for 235 Keonekai Rd 48 of 50 Listing Image for 235 Keonekai Rd 49 of 50 Listing Image for 235 Keonekai Rd 50 of 50

$1,440,000

Kihei

235 Keonekai Rd, Kihei

3 Beds 3 Baths 1,832 SqFt Residential MLS® # 408126 Date Sold: April 20, 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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