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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Short Term Rental
Listing Image for 2481 Kaanapali Pkwy 964 1 of 50 Listing Image for 2481 Kaanapali Pkwy 964 2 of 50 Listing Image for 2481 Kaanapali Pkwy 964 3 of 50 Listing Image for 2481 Kaanapali Pkwy 964 4 of 50 Listing Image for 2481 Kaanapali Pkwy 964 5 of 50 Listing Image for 2481 Kaanapali Pkwy 964 6 of 50 Listing Image for 2481 Kaanapali Pkwy 964 7 of 50 Listing Image for 2481 Kaanapali Pkwy 964 8 of 50 Listing Image for 2481 Kaanapali Pkwy 964 9 of 50 Listing Image for 2481 Kaanapali Pkwy 964 10 of 50 Listing Image for 2481 Kaanapali Pkwy 964 11 of 50 Listing Image for 2481 Kaanapali Pkwy 964 12 of 50 Listing Image for 2481 Kaanapali Pkwy 964 13 of 50 Listing Image for 2481 Kaanapali Pkwy 964 14 of 50 Listing Image for 2481 Kaanapali Pkwy 964 15 of 50 Listing Image for 2481 Kaanapali Pkwy 964 16 of 50 Listing Image for 2481 Kaanapali Pkwy 964 17 of 50 Listing Image for 2481 Kaanapali Pkwy 964 18 of 50 Listing Image for 2481 Kaanapali Pkwy 964 19 of 50 Listing Image for 2481 Kaanapali Pkwy 964 20 of 50 Listing Image for 2481 Kaanapali Pkwy 964 21 of 50 Listing Image for 2481 Kaanapali Pkwy 964 22 of 50 Listing Image for 2481 Kaanapali Pkwy 964 23 of 50 Listing Image for 2481 Kaanapali Pkwy 964 24 of 50 Listing Image for 2481 Kaanapali Pkwy 964 25 of 50 Listing Image for 2481 Kaanapali Pkwy 964 26 of 50 Listing Image for 2481 Kaanapali Pkwy 964 27 of 50 Listing Image for 2481 Kaanapali Pkwy 964 28 of 50 Listing Image for 2481 Kaanapali Pkwy 964 29 of 50 Listing Image for 2481 Kaanapali Pkwy 964 30 of 50 Listing Image for 2481 Kaanapali Pkwy 964 31 of 50 Listing Image for 2481 Kaanapali Pkwy 964 32 of 50 Listing Image for 2481 Kaanapali Pkwy 964 33 of 50 Listing Image for 2481 Kaanapali Pkwy 964 34 of 50 Listing Image for 2481 Kaanapali Pkwy 964 35 of 50 Listing Image for 2481 Kaanapali Pkwy 964 36 of 50 Listing Image for 2481 Kaanapali Pkwy 964 37 of 50 Listing Image for 2481 Kaanapali Pkwy 964 38 of 50 Listing Image for 2481 Kaanapali Pkwy 964 39 of 50 Listing Image for 2481 Kaanapali Pkwy 964 40 of 50 Listing Image for 2481 Kaanapali Pkwy 964 41 of 50 Listing Image for 2481 Kaanapali Pkwy 964 42 of 50 Listing Image for 2481 Kaanapali Pkwy 964 43 of 50 Listing Image for 2481 Kaanapali Pkwy 964 44 of 50 Listing Image for 2481 Kaanapali Pkwy 964 45 of 50 Listing Image for 2481 Kaanapali Pkwy 964 46 of 50 Listing Image for 2481 Kaanapali Pkwy 964 47 of 50 Listing Image for 2481 Kaanapali Pkwy 964 48 of 50 Listing Image for 2481 Kaanapali Pkwy 964 49 of 50 Listing Image for 2481 Kaanapali Pkwy 964 50 of 50

$1,100,000

Whaler 964

2481 Kaanapali Pkwy 964, Kaanapali

0 Beds 1 Bath 523 SqFt Residential MLS® # 410672

Days on Market: 13

Hawaii Life (W) Cell: 808-283-2222

Listing Image for 3150 Wailea Alanui Dr 2801 1 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 2 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 3 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 4 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 5 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 6 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 7 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 8 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 9 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 10 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 11 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 12 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 13 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 14 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 15 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 16 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 17 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 18 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 19 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 20 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 21 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 22 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 23 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 24 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 25 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 26 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 27 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 28 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 29 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 30 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 31 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 32 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 33 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 34 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 35 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 36 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 37 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 38 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 39 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 40 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 41 of 42 Listing Image for 3150 Wailea Alanui Dr 2801 42 of 42

$1,850,000

Wailea Palms 2801

3150 Wailea Alanui Dr 2801, Wailea/Makena

2 Beds 3 Baths 1,559 SqFt Residential MLS® # 410669

Days on Market: 13

Coldwell Banker Island Prop(S) Cell: 808-298-7910

In Escrow
Listing Image for 1063 Kauhikoa Rd 1 of 17 Listing Image for 1063 Kauhikoa Rd 2 of 17 Listing Image for 1063 Kauhikoa Rd 3 of 17 Listing Image for 1063 Kauhikoa Rd 4 of 17 Listing Image for 1063 Kauhikoa Rd 5 of 17 Listing Image for 1063 Kauhikoa Rd 6 of 17 Listing Image for 1063 Kauhikoa Rd 7 of 17 Listing Image for 1063 Kauhikoa Rd 8 of 17 Listing Image for 1063 Kauhikoa Rd 9 of 17 Listing Image for 1063 Kauhikoa Rd 10 of 17 Listing Image for 1063 Kauhikoa Rd 11 of 17 Listing Image for 1063 Kauhikoa Rd 12 of 17 Listing Image for 1063 Kauhikoa Rd 13 of 17 Listing Image for 1063 Kauhikoa Rd 14 of 17 Listing Image for 1063 Kauhikoa Rd 15 of 17 Listing Image for 1063 Kauhikoa Rd 16 of 17 Listing Image for 1063 Kauhikoa Rd 17 of 17

$1,395,000

Haiku

1063 Kauhikoa Rd, Haiku

2 Beds 3 Baths 1,674 SqFt Residential MLS® # 410668

Days on Market: 14

Live Maui Real Estate LLC

Short Term Rental
Listing Image for 760 S Kihei Rd 427 1 of 47 Listing Image for 760 S Kihei Rd 427 2 of 47 Listing Image for 760 S Kihei Rd 427 3 of 47 Listing Image for 760 S Kihei Rd 427 4 of 47 Listing Image for 760 S Kihei Rd 427 5 of 47 Listing Image for 760 S Kihei Rd 427 6 of 47 Listing Image for 760 S Kihei Rd 427 7 of 47 Listing Image for 760 S Kihei Rd 427 8 of 47 Listing Image for 760 S Kihei Rd 427 9 of 47 Listing Image for 760 S Kihei Rd 427 10 of 47 Listing Image for 760 S Kihei Rd 427 11 of 47 Listing Image for 760 S Kihei Rd 427 12 of 47 Listing Image for 760 S Kihei Rd 427 13 of 47 Listing Image for 760 S Kihei Rd 427 14 of 47 Listing Image for 760 S Kihei Rd 427 15 of 47 Listing Image for 760 S Kihei Rd 427 16 of 47 Listing Image for 760 S Kihei Rd 427 17 of 47 Listing Image for 760 S Kihei Rd 427 18 of 47 Listing Image for 760 S Kihei Rd 427 19 of 47 Listing Image for 760 S Kihei Rd 427 20 of 47 Listing Image for 760 S Kihei Rd 427 21 of 47 Listing Image for 760 S Kihei Rd 427 22 of 47 Listing Image for 760 S Kihei Rd 427 23 of 47 Listing Image for 760 S Kihei Rd 427 24 of 47 Listing Image for 760 S Kihei Rd 427 25 of 47 Listing Image for 760 S Kihei Rd 427 26 of 47 Listing Image for 760 S Kihei Rd 427 27 of 47 Listing Image for 760 S Kihei Rd 427 28 of 47 Listing Image for 760 S Kihei Rd 427 29 of 47 Listing Image for 760 S Kihei Rd 427 30 of 47 Listing Image for 760 S Kihei Rd 427 31 of 47 Listing Image for 760 S Kihei Rd 427 32 of 47 Listing Image for 760 S Kihei Rd 427 33 of 47 Listing Image for 760 S Kihei Rd 427 34 of 47 Listing Image for 760 S Kihei Rd 427 35 of 47 Listing Image for 760 S Kihei Rd 427 36 of 47 Listing Image for 760 S Kihei Rd 427 37 of 47 Listing Image for 760 S Kihei Rd 427 38 of 47 Listing Image for 760 S Kihei Rd 427 39 of 47 Listing Image for 760 S Kihei Rd 427 40 of 47 Listing Image for 760 S Kihei Rd 427 41 of 47 Listing Image for 760 S Kihei Rd 427 42 of 47 Listing Image for 760 S Kihei Rd 427 43 of 47 Listing Image for 760 S Kihei Rd 427 44 of 47 Listing Image for 760 S Kihei Rd 427 45 of 47 Listing Image for 760 S Kihei Rd 427 46 of 47 Listing Image for 760 S Kihei Rd 427 47 of 47

$1,200,000

Menehune Shores 427

760 S Kihei Rd 427, Kihei

2 Beds 2 Baths 885 SqFt Residential MLS® # 410666

Days on Market: 14

Keller Williams Realty Maui-Ki Cell: 808-481-9748

Short Term Rental
Listing Image for 130 Kai Malina Pkwy Sr236 1 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 2 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 3 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 4 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 5 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 6 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 7 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 8 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 9 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 10 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 11 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 12 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 13 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 14 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 15 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 16 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 17 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 18 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 19 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 20 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 21 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 22 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 23 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 24 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 25 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 26 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 27 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 28 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 29 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 30 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 31 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 32 of 33 Listing Image for 130 Kai Malina Pkwy Sr236 33 of 33

$2,195,000

Honua Kai - Hoku Lani SR236

130 Kai Malina Pkwy Sr236, Kaanapali

2 Beds 2 Baths 1,240 SqFt Residential MLS® # 410661

Days on Market: 15

KBM Hawaii

Short Term Rental
Listing Image for 130 Kai Malina Pkwy Nr540 1 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 2 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 3 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 4 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 5 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 6 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 7 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 8 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 9 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 10 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 11 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 12 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 13 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 14 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 15 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 16 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 17 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 18 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 19 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 20 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 21 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 22 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 23 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 24 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 25 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 26 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 27 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 28 of 29 Listing Image for 130 Kai Malina Pkwy Nr540 29 of 29

$1,350,000

Honua Kai - Konea NR540

130 Kai Malina Pkwy Nr540, Kaanapali

2 Beds 1 Bath 915 SqFt Residential MLS® # 410659

Days on Market: 15

Coldwell Banker Island Prop-KP Cell: 808-446-5841

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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: 09/04/2026
Listing Image for 155 Wailea Ike Pl 30 1 of 42 Listing Image for 155 Wailea Ike Pl 30 2 of 42 Listing Image for 155 Wailea Ike Pl 30 3 of 42 Listing Image for 155 Wailea Ike Pl 30 4 of 42 Listing Image for 155 Wailea Ike Pl 30 5 of 42 Listing Image for 155 Wailea Ike Pl 30 6 of 42 Listing Image for 155 Wailea Ike Pl 30 7 of 42 Listing Image for 155 Wailea Ike Pl 30 8 of 42 Listing Image for 155 Wailea Ike Pl 30 9 of 42 Listing Image for 155 Wailea Ike Pl 30 10 of 42 Listing Image for 155 Wailea Ike Pl 30 11 of 42 Listing Image for 155 Wailea Ike Pl 30 12 of 42 Listing Image for 155 Wailea Ike Pl 30 13 of 42 Listing Image for 155 Wailea Ike Pl 30 14 of 42 Listing Image for 155 Wailea Ike Pl 30 15 of 42 Listing Image for 155 Wailea Ike Pl 30 16 of 42 Listing Image for 155 Wailea Ike Pl 30 17 of 42 Listing Image for 155 Wailea Ike Pl 30 18 of 42 Listing Image for 155 Wailea Ike Pl 30 19 of 42 Listing Image for 155 Wailea Ike Pl 30 20 of 42 Listing Image for 155 Wailea Ike Pl 30 21 of 42 Listing Image for 155 Wailea Ike Pl 30 22 of 42 Listing Image for 155 Wailea Ike Pl 30 23 of 42 Listing Image for 155 Wailea Ike Pl 30 24 of 42 Listing Image for 155 Wailea Ike Pl 30 25 of 42 Listing Image for 155 Wailea Ike Pl 30 26 of 42 Listing Image for 155 Wailea Ike Pl 30 27 of 42 Listing Image for 155 Wailea Ike Pl 30 28 of 42 Listing Image for 155 Wailea Ike Pl 30 29 of 42 Listing Image for 155 Wailea Ike Pl 30 30 of 42 Listing Image for 155 Wailea Ike Pl 30 31 of 42 Listing Image for 155 Wailea Ike Pl 30 32 of 42 Listing Image for 155 Wailea Ike Pl 30 33 of 42 Listing Image for 155 Wailea Ike Pl 30 34 of 42 Listing Image for 155 Wailea Ike Pl 30 35 of 42 Listing Image for 155 Wailea Ike Pl 30 36 of 42 Listing Image for 155 Wailea Ike Pl 30 37 of 42 Listing Image for 155 Wailea Ike Pl 30 38 of 42 Listing Image for 155 Wailea Ike Pl 30 39 of 42 Listing Image for 155 Wailea Ike Pl 30 40 of 42 Listing Image for 155 Wailea Ike Pl 30 41 of 42 Listing Image for 155 Wailea Ike Pl 30 42 of 42

$1,075,000

Grand Champions 30

155 Wailea Ike Pl 30, Wailea/Makena

2 Beds 2 Baths 1,148 SqFt Residential MLS® # 410048 Date Sold: September 4, 2026
Sold
Closed: 07/27/2026
Listing Image for 100 Malapua Pl 1 of 36 Listing Image for 100 Malapua Pl 2 of 36 Listing Image for 100 Malapua Pl 3 of 36 Listing Image for 100 Malapua Pl 4 of 36 Listing Image for 100 Malapua Pl 5 of 36 Listing Image for 100 Malapua Pl 6 of 36 Listing Image for 100 Malapua Pl 7 of 36 Listing Image for 100 Malapua Pl 8 of 36 Listing Image for 100 Malapua Pl 9 of 36 Listing Image for 100 Malapua Pl 10 of 36 Listing Image for 100 Malapua Pl 11 of 36 Listing Image for 100 Malapua Pl 12 of 36 Listing Image for 100 Malapua Pl 13 of 36 Listing Image for 100 Malapua Pl 14 of 36 Listing Image for 100 Malapua Pl 15 of 36 Listing Image for 100 Malapua Pl 16 of 36 Listing Image for 100 Malapua Pl 17 of 36 Listing Image for 100 Malapua Pl 18 of 36 Listing Image for 100 Malapua Pl 19 of 36 Listing Image for 100 Malapua Pl 20 of 36 Listing Image for 100 Malapua Pl 21 of 36 Listing Image for 100 Malapua Pl 22 of 36 Listing Image for 100 Malapua Pl 23 of 36 Listing Image for 100 Malapua Pl 24 of 36 Listing Image for 100 Malapua Pl 25 of 36 Listing Image for 100 Malapua Pl 26 of 36 Listing Image for 100 Malapua Pl 27 of 36 Listing Image for 100 Malapua Pl 28 of 36 Listing Image for 100 Malapua Pl 29 of 36 Listing Image for 100 Malapua Pl 30 of 36 Listing Image for 100 Malapua Pl 31 of 36 Listing Image for 100 Malapua Pl 32 of 36 Listing Image for 100 Malapua Pl 33 of 36 Listing Image for 100 Malapua Pl 34 of 36 Listing Image for 100 Malapua Pl 35 of 36 Listing Image for 100 Malapua Pl 36 of 36

$1,400,000

Kulamanu

100 Malapua Pl, Kula/Ulupalakua/Kanaio

3 Beds 2 Baths 1,465 SqFt Residential MLS® # 410045 Date Sold: July 27, 2026
Sold
Closed: 09/01/2026
Listing Image for 145 Lanakila Pl 1 of 49 Listing Image for 145 Lanakila Pl 2 of 49 Listing Image for 145 Lanakila Pl 3 of 49 Listing Image for 145 Lanakila Pl 4 of 49 Listing Image for 145 Lanakila Pl 5 of 49 Listing Image for 145 Lanakila Pl 6 of 49 Listing Image for 145 Lanakila Pl 7 of 49 Listing Image for 145 Lanakila Pl 8 of 49 Listing Image for 145 Lanakila Pl 9 of 49 Listing Image for 145 Lanakila Pl 10 of 49 Listing Image for 145 Lanakila Pl 11 of 49 Listing Image for 145 Lanakila Pl 12 of 49 Listing Image for 145 Lanakila Pl 13 of 49 Listing Image for 145 Lanakila Pl 14 of 49 Listing Image for 145 Lanakila Pl 15 of 49 Listing Image for 145 Lanakila Pl 16 of 49 Listing Image for 145 Lanakila Pl 17 of 49 Listing Image for 145 Lanakila Pl 18 of 49 Listing Image for 145 Lanakila Pl 19 of 49 Listing Image for 145 Lanakila Pl 20 of 49 Listing Image for 145 Lanakila Pl 21 of 49 Listing Image for 145 Lanakila Pl 22 of 49 Listing Image for 145 Lanakila Pl 23 of 49 Listing Image for 145 Lanakila Pl 24 of 49 Listing Image for 145 Lanakila Pl 25 of 49 Listing Image for 145 Lanakila Pl 26 of 49 Listing Image for 145 Lanakila Pl 27 of 49 Listing Image for 145 Lanakila Pl 28 of 49 Listing Image for 145 Lanakila Pl 29 of 49 Listing Image for 145 Lanakila Pl 30 of 49 Listing Image for 145 Lanakila Pl 31 of 49 Listing Image for 145 Lanakila Pl 32 of 49 Listing Image for 145 Lanakila Pl 33 of 49 Listing Image for 145 Lanakila Pl 34 of 49 Listing Image for 145 Lanakila Pl 35 of 49 Listing Image for 145 Lanakila Pl 36 of 49 Listing Image for 145 Lanakila Pl 37 of 49 Listing Image for 145 Lanakila Pl 38 of 49 Listing Image for 145 Lanakila Pl 39 of 49 Listing Image for 145 Lanakila Pl 40 of 49 Listing Image for 145 Lanakila Pl 41 of 49 Listing Image for 145 Lanakila Pl 42 of 49 Listing Image for 145 Lanakila Pl 43 of 49 Listing Image for 145 Lanakila Pl 44 of 49 Listing Image for 145 Lanakila Pl 45 of 49 Listing Image for 145 Lanakila Pl 46 of 49 Listing Image for 145 Lanakila Pl 47 of 49 Listing Image for 145 Lanakila Pl 48 of 49 Listing Image for 145 Lanakila Pl 49 of 49

$989,000

Kenolio

145 Lanakila Pl, Kihei

3 Beds 2 Baths 1,056 SqFt Residential MLS® # 410032 Date Sold: September 1, 2026
Sold
Closed: 07/29/2026
Listing Image for 2777 S Kihei Rd F203 1 of 37 Listing Image for 2777 S Kihei Rd F203 2 of 37 Listing Image for 2777 S Kihei Rd F203 3 of 37 Listing Image for 2777 S Kihei Rd F203 4 of 37 Listing Image for 2777 S Kihei Rd F203 5 of 37 Listing Image for 2777 S Kihei Rd F203 6 of 37 Listing Image for 2777 S Kihei Rd F203 7 of 37 Listing Image for 2777 S Kihei Rd F203 8 of 37 Listing Image for 2777 S Kihei Rd F203 9 of 37 Listing Image for 2777 S Kihei Rd F203 10 of 37 Listing Image for 2777 S Kihei Rd F203 11 of 37 Listing Image for 2777 S Kihei Rd F203 12 of 37 Listing Image for 2777 S Kihei Rd F203 13 of 37 Listing Image for 2777 S Kihei Rd F203 14 of 37 Listing Image for 2777 S Kihei Rd F203 15 of 37 Listing Image for 2777 S Kihei Rd F203 16 of 37 Listing Image for 2777 S Kihei Rd F203 17 of 37 Listing Image for 2777 S Kihei Rd F203 18 of 37 Listing Image for 2777 S Kihei Rd F203 19 of 37 Listing Image for 2777 S Kihei Rd F203 20 of 37 Listing Image for 2777 S Kihei Rd F203 21 of 37 Listing Image for 2777 S Kihei Rd F203 22 of 37 Listing Image for 2777 S Kihei Rd F203 23 of 37 Listing Image for 2777 S Kihei Rd F203 24 of 37 Listing Image for 2777 S Kihei Rd F203 25 of 37 Listing Image for 2777 S Kihei Rd F203 26 of 37 Listing Image for 2777 S Kihei Rd F203 27 of 37 Listing Image for 2777 S Kihei Rd F203 28 of 37 Listing Image for 2777 S Kihei Rd F203 29 of 37 Listing Image for 2777 S Kihei Rd F203 30 of 37 Listing Image for 2777 S Kihei Rd F203 31 of 37 Listing Image for 2777 S Kihei Rd F203 32 of 37 Listing Image for 2777 S Kihei Rd F203 33 of 37 Listing Image for 2777 S Kihei Rd F203 34 of 37 Listing Image for 2777 S Kihei Rd F203 35 of 37 Listing Image for 2777 S Kihei Rd F203 36 of 37 Listing Image for 2777 S Kihei Rd F203 37 of 37

$1,000,000

Maui Kamaole F203

2777 S Kihei Rd F203, Kihei

2 Beds 2 Baths 1,214 SqFt Residential MLS® # 407322 Date Sold: July 29, 2026
Sold
Closed: 08/14/2026
Listing Image for 125 Mehani Pl 1 of 48 Listing Image for 125 Mehani Pl 2 of 48 Listing Image for 125 Mehani Pl 3 of 48 Listing Image for 125 Mehani Pl 4 of 48 Listing Image for 125 Mehani Pl 5 of 48 Listing Image for 125 Mehani Pl 6 of 48 Listing Image for 125 Mehani Pl 7 of 48 Listing Image for 125 Mehani Pl 8 of 48 Listing Image for 125 Mehani Pl 9 of 48 Listing Image for 125 Mehani Pl 10 of 48 Listing Image for 125 Mehani Pl 11 of 48 Listing Image for 125 Mehani Pl 12 of 48 Listing Image for 125 Mehani Pl 13 of 48 Listing Image for 125 Mehani Pl 14 of 48 Listing Image for 125 Mehani Pl 15 of 48 Listing Image for 125 Mehani Pl 16 of 48 Listing Image for 125 Mehani Pl 17 of 48 Listing Image for 125 Mehani Pl 18 of 48 Listing Image for 125 Mehani Pl 19 of 48 Listing Image for 125 Mehani Pl 20 of 48 Listing Image for 125 Mehani Pl 21 of 48 Listing Image for 125 Mehani Pl 22 of 48 Listing Image for 125 Mehani Pl 23 of 48 Listing Image for 125 Mehani Pl 24 of 48 Listing Image for 125 Mehani Pl 25 of 48 Listing Image for 125 Mehani Pl 26 of 48 Listing Image for 125 Mehani Pl 27 of 48 Listing Image for 125 Mehani Pl 28 of 48 Listing Image for 125 Mehani Pl 29 of 48 Listing Image for 125 Mehani Pl 30 of 48 Listing Image for 125 Mehani Pl 31 of 48 Listing Image for 125 Mehani Pl 32 of 48 Listing Image for 125 Mehani Pl 33 of 48 Listing Image for 125 Mehani Pl 34 of 48 Listing Image for 125 Mehani Pl 35 of 48 Listing Image for 125 Mehani Pl 36 of 48 Listing Image for 125 Mehani Pl 37 of 48 Listing Image for 125 Mehani Pl 38 of 48 Listing Image for 125 Mehani Pl 39 of 48 Listing Image for 125 Mehani Pl 40 of 48 Listing Image for 125 Mehani Pl 41 of 48 Listing Image for 125 Mehani Pl 42 of 48 Listing Image for 125 Mehani Pl 43 of 48 Listing Image for 125 Mehani Pl 44 of 48 Listing Image for 125 Mehani Pl 45 of 48 Listing Image for 125 Mehani Pl 46 of 48 Listing Image for 125 Mehani Pl 47 of 48 Listing Image for 125 Mehani Pl 48 of 48

$1,100,000

↓ $155,000

Kihei

125 Mehani Pl, Kihei

3 Beds 2 Baths 1,236 SqFt Residential MLS® # 410014 Date Sold: August 14, 2026
Sold
Closed: 09/01/2026
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$2,500,000

Makawao/Olinda/Haliimaile

1423 Olinda Rd, Makawao/Olinda/Haliimaile

3 Beds 2 Baths 1,632 SqFt Residential MLS® # 409998 Date Sold: September 1, 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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