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 4909 Lower Honoapiilani Rd A6 1 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 2 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 3 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 4 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 5 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 6 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 7 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 8 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 9 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 10 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 11 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 12 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 13 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 14 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 15 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 16 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 17 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 18 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 19 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 20 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 21 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 22 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 23 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 24 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 25 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 26 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 27 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 28 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 29 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 30 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 31 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 32 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 33 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 34 of 35 Listing Image for 4909 Lower Honoapiilani Rd A6 35 of 35

$1,000,000

Kahana Sunset A6

4909 Lower Honoapiilani Rd A6, Napili/Kahana/Honokowai

2 Beds 2.5 Baths 1,064 SqFt Residential MLS® # 409790

Days on Market: 106

Coldwell Banker Island Prop-KP Cell: 808-250-1583

Listing Image for 1437 Umeke Cir 100 1 of 49 Listing Image for 1437 Umeke Cir 100 2 of 49 Listing Image for 1437 Umeke Cir 100 3 of 49 Listing Image for 1437 Umeke Cir 100 4 of 49 Listing Image for 1437 Umeke Cir 100 5 of 49 Listing Image for 1437 Umeke Cir 100 6 of 49 Listing Image for 1437 Umeke Cir 100 7 of 49 Listing Image for 1437 Umeke Cir 100 8 of 49 Listing Image for 1437 Umeke Cir 100 9 of 49 Listing Image for 1437 Umeke Cir 100 10 of 49 Listing Image for 1437 Umeke Cir 100 11 of 49 Listing Image for 1437 Umeke Cir 100 12 of 49 Listing Image for 1437 Umeke Cir 100 13 of 49 Listing Image for 1437 Umeke Cir 100 14 of 49 Listing Image for 1437 Umeke Cir 100 15 of 49 Listing Image for 1437 Umeke Cir 100 16 of 49 Listing Image for 1437 Umeke Cir 100 17 of 49 Listing Image for 1437 Umeke Cir 100 18 of 49 Listing Image for 1437 Umeke Cir 100 19 of 49 Listing Image for 1437 Umeke Cir 100 20 of 49 Listing Image for 1437 Umeke Cir 100 21 of 49 Listing Image for 1437 Umeke Cir 100 22 of 49 Listing Image for 1437 Umeke Cir 100 23 of 49 Listing Image for 1437 Umeke Cir 100 24 of 49 Listing Image for 1437 Umeke Cir 100 25 of 49 Listing Image for 1437 Umeke Cir 100 26 of 49 Listing Image for 1437 Umeke Cir 100 27 of 49 Listing Image for 1437 Umeke Cir 100 28 of 49 Listing Image for 1437 Umeke Cir 100 29 of 49 Listing Image for 1437 Umeke Cir 100 30 of 49 Listing Image for 1437 Umeke Cir 100 31 of 49 Listing Image for 1437 Umeke Cir 100 32 of 49 Listing Image for 1437 Umeke Cir 100 33 of 49 Listing Image for 1437 Umeke Cir 100 34 of 49 Listing Image for 1437 Umeke Cir 100 35 of 49 Listing Image for 1437 Umeke Cir 100 36 of 49 Listing Image for 1437 Umeke Cir 100 37 of 49 Listing Image for 1437 Umeke Cir 100 38 of 49 Listing Image for 1437 Umeke Cir 100 39 of 49 Listing Image for 1437 Umeke Cir 100 40 of 49 Listing Image for 1437 Umeke Cir 100 41 of 49 Listing Image for 1437 Umeke Cir 100 42 of 49 Listing Image for 1437 Umeke Cir 100 43 of 49 Listing Image for 1437 Umeke Cir 100 44 of 49 Listing Image for 1437 Umeke Cir 100 45 of 49 Listing Image for 1437 Umeke Cir 100 46 of 49 Listing Image for 1437 Umeke Cir 100 47 of 49 Listing Image for 1437 Umeke Cir 100 48 of 49 Listing Image for 1437 Umeke Cir 100 49 of 49

$1,850,000

↓ $75,000

Hokulani Golf Villas 100

1437 Umeke Cir 100, Kihei

3 Beds 2.5 Baths 2,429 SqFt Residential MLS® # 409786

Days on Market: 106

Hawaii Life (W) Cell: 808-298-7455

Listing Image for 2695 Lia Pl 1 of 37 Listing Image for 2695 Lia Pl 2 of 37 Listing Image for 2695 Lia Pl 3 of 37 Listing Image for 2695 Lia Pl 4 of 37 Listing Image for 2695 Lia Pl 5 of 37 Listing Image for 2695 Lia Pl 6 of 37 Listing Image for 2695 Lia Pl 7 of 37 Listing Image for 2695 Lia Pl 8 of 37 Listing Image for 2695 Lia Pl 9 of 37 Listing Image for 2695 Lia Pl 10 of 37 Listing Image for 2695 Lia Pl 11 of 37 Listing Image for 2695 Lia Pl 12 of 37 Listing Image for 2695 Lia Pl 13 of 37 Listing Image for 2695 Lia Pl 14 of 37 Listing Image for 2695 Lia Pl 15 of 37 Listing Image for 2695 Lia Pl 16 of 37 Listing Image for 2695 Lia Pl 17 of 37 Listing Image for 2695 Lia Pl 18 of 37 Listing Image for 2695 Lia Pl 19 of 37 Listing Image for 2695 Lia Pl 20 of 37 Listing Image for 2695 Lia Pl 21 of 37 Listing Image for 2695 Lia Pl 22 of 37 Listing Image for 2695 Lia Pl 23 of 37 Listing Image for 2695 Lia Pl 24 of 37 Listing Image for 2695 Lia Pl 25 of 37 Listing Image for 2695 Lia Pl 26 of 37 Listing Image for 2695 Lia Pl 27 of 37 Listing Image for 2695 Lia Pl 28 of 37 Listing Image for 2695 Lia Pl 29 of 37 Listing Image for 2695 Lia Pl 30 of 37 Listing Image for 2695 Lia Pl 31 of 37 Listing Image for 2695 Lia Pl 32 of 37 Listing Image for 2695 Lia Pl 33 of 37 Listing Image for 2695 Lia Pl 34 of 37 Listing Image for 2695 Lia Pl 35 of 37 Listing Image for 2695 Lia Pl 36 of 37 Listing Image for 2695 Lia Pl 37 of 37

$2,190,000

↓ $100,000

Haiku Country Estates

2695 Lia Pl, Haiku

3 Beds 3 Baths 2,482 SqFt Residential MLS® # 409783

Days on Market: 106

Kokua Realty LLC

Listing Image for 1015 Anapuni Pl 62 1 of 50 Listing Image for 1015 Anapuni Pl 62 2 of 50 Listing Image for 1015 Anapuni Pl 62 3 of 50 Listing Image for 1015 Anapuni Pl 62 4 of 50 Listing Image for 1015 Anapuni Pl 62 5 of 50 Listing Image for 1015 Anapuni Pl 62 6 of 50 Listing Image for 1015 Anapuni Pl 62 7 of 50 Listing Image for 1015 Anapuni Pl 62 8 of 50 Listing Image for 1015 Anapuni Pl 62 9 of 50 Listing Image for 1015 Anapuni Pl 62 10 of 50 Listing Image for 1015 Anapuni Pl 62 11 of 50 Listing Image for 1015 Anapuni Pl 62 12 of 50 Listing Image for 1015 Anapuni Pl 62 13 of 50 Listing Image for 1015 Anapuni Pl 62 14 of 50 Listing Image for 1015 Anapuni Pl 62 15 of 50 Listing Image for 1015 Anapuni Pl 62 16 of 50 Listing Image for 1015 Anapuni Pl 62 17 of 50 Listing Image for 1015 Anapuni Pl 62 18 of 50 Listing Image for 1015 Anapuni Pl 62 19 of 50 Listing Image for 1015 Anapuni Pl 62 20 of 50 Listing Image for 1015 Anapuni Pl 62 21 of 50 Listing Image for 1015 Anapuni Pl 62 22 of 50 Listing Image for 1015 Anapuni Pl 62 23 of 50 Listing Image for 1015 Anapuni Pl 62 24 of 50 Listing Image for 1015 Anapuni Pl 62 25 of 50 Listing Image for 1015 Anapuni Pl 62 26 of 50 Listing Image for 1015 Anapuni Pl 62 27 of 50 Listing Image for 1015 Anapuni Pl 62 28 of 50 Listing Image for 1015 Anapuni Pl 62 29 of 50 Listing Image for 1015 Anapuni Pl 62 30 of 50 Listing Image for 1015 Anapuni Pl 62 31 of 50 Listing Image for 1015 Anapuni Pl 62 32 of 50 Listing Image for 1015 Anapuni Pl 62 33 of 50 Listing Image for 1015 Anapuni Pl 62 34 of 50 Listing Image for 1015 Anapuni Pl 62 35 of 50 Listing Image for 1015 Anapuni Pl 62 36 of 50 Listing Image for 1015 Anapuni Pl 62 37 of 50 Listing Image for 1015 Anapuni Pl 62 38 of 50 Listing Image for 1015 Anapuni Pl 62 39 of 50 Listing Image for 1015 Anapuni Pl 62 40 of 50 Listing Image for 1015 Anapuni Pl 62 41 of 50 Listing Image for 1015 Anapuni Pl 62 42 of 50 Listing Image for 1015 Anapuni Pl 62 43 of 50 Listing Image for 1015 Anapuni Pl 62 44 of 50 Listing Image for 1015 Anapuni Pl 62 45 of 50 Listing Image for 1015 Anapuni Pl 62 46 of 50 Listing Image for 1015 Anapuni Pl 62 47 of 50 Listing Image for 1015 Anapuni Pl 62 48 of 50 Listing Image for 1015 Anapuni Pl 62 49 of 50 Listing Image for 1015 Anapuni Pl 62 50 of 50

$7,500,000

Lanikeha

1015 Anapuni Pl 62, Kaanapali

4 Beds 4.5 Baths 4,012 SqFt Residential MLS® # 409785

Days on Market: 106

Coldwell Banker Island Prop-KP Cell: 808-250-1583

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 21 Laukona St 1901 1 of 50 Listing Image for 21 Laukona St 1901 2 of 50 Listing Image for 21 Laukona St 1901 3 of 50 Listing Image for 21 Laukona St 1901 4 of 50 Listing Image for 21 Laukona St 1901 5 of 50 Listing Image for 21 Laukona St 1901 6 of 50 Listing Image for 21 Laukona St 1901 7 of 50 Listing Image for 21 Laukona St 1901 8 of 50 Listing Image for 21 Laukona St 1901 9 of 50 Listing Image for 21 Laukona St 1901 10 of 50 Listing Image for 21 Laukona St 1901 11 of 50 Listing Image for 21 Laukona St 1901 12 of 50 Listing Image for 21 Laukona St 1901 13 of 50 Listing Image for 21 Laukona St 1901 14 of 50 Listing Image for 21 Laukona St 1901 15 of 50 Listing Image for 21 Laukona St 1901 16 of 50 Listing Image for 21 Laukona St 1901 17 of 50 Listing Image for 21 Laukona St 1901 18 of 50 Listing Image for 21 Laukona St 1901 19 of 50 Listing Image for 21 Laukona St 1901 20 of 50 Listing Image for 21 Laukona St 1901 21 of 50 Listing Image for 21 Laukona St 1901 22 of 50 Listing Image for 21 Laukona St 1901 23 of 50 Listing Image for 21 Laukona St 1901 24 of 50 Listing Image for 21 Laukona St 1901 25 of 50 Listing Image for 21 Laukona St 1901 26 of 50 Listing Image for 21 Laukona St 1901 27 of 50 Listing Image for 21 Laukona St 1901 28 of 50 Listing Image for 21 Laukona St 1901 29 of 50 Listing Image for 21 Laukona St 1901 30 of 50 Listing Image for 21 Laukona St 1901 31 of 50 Listing Image for 21 Laukona St 1901 32 of 50 Listing Image for 21 Laukona St 1901 33 of 50 Listing Image for 21 Laukona St 1901 34 of 50 Listing Image for 21 Laukona St 1901 35 of 50 Listing Image for 21 Laukona St 1901 36 of 50 Listing Image for 21 Laukona St 1901 37 of 50 Listing Image for 21 Laukona St 1901 38 of 50 Listing Image for 21 Laukona St 1901 39 of 50 Listing Image for 21 Laukona St 1901 40 of 50 Listing Image for 21 Laukona St 1901 41 of 50 Listing Image for 21 Laukona St 1901 42 of 50 Listing Image for 21 Laukona St 1901 43 of 50 Listing Image for 21 Laukona St 1901 44 of 50 Listing Image for 21 Laukona St 1901 45 of 50 Listing Image for 21 Laukona St 1901 46 of 50 Listing Image for 21 Laukona St 1901 47 of 50 Listing Image for 21 Laukona St 1901 48 of 50 Listing Image for 21 Laukona St 1901 49 of 50 Listing Image for 21 Laukona St 1901 50 of 50

$995,000

Villas at Kehalani 1901

21 Laukona St 1901, Wailuku

2 Beds 2.5 Baths 1,446 SqFt Residential MLS® # 409781

Days on Market: 106

Welcome Hawaii Properties Cell: 808-268-0826

In Escrow Short Term Rental
Listing Image for 130 Kai Malina Pkwy 719 1 of 33 Listing Image for 130 Kai Malina Pkwy 719 2 of 33 Listing Image for 130 Kai Malina Pkwy 719 3 of 33 Listing Image for 130 Kai Malina Pkwy 719 4 of 33 Listing Image for 130 Kai Malina Pkwy 719 5 of 33 Listing Image for 130 Kai Malina Pkwy 719 6 of 33 Listing Image for 130 Kai Malina Pkwy 719 7 of 33 Listing Image for 130 Kai Malina Pkwy 719 8 of 33 Listing Image for 130 Kai Malina Pkwy 719 9 of 33 Listing Image for 130 Kai Malina Pkwy 719 10 of 33 Listing Image for 130 Kai Malina Pkwy 719 11 of 33 Listing Image for 130 Kai Malina Pkwy 719 12 of 33 Listing Image for 130 Kai Malina Pkwy 719 13 of 33 Listing Image for 130 Kai Malina Pkwy 719 14 of 33 Listing Image for 130 Kai Malina Pkwy 719 15 of 33 Listing Image for 130 Kai Malina Pkwy 719 16 of 33 Listing Image for 130 Kai Malina Pkwy 719 17 of 33 Listing Image for 130 Kai Malina Pkwy 719 18 of 33 Listing Image for 130 Kai Malina Pkwy 719 19 of 33 Listing Image for 130 Kai Malina Pkwy 719 20 of 33 Listing Image for 130 Kai Malina Pkwy 719 21 of 33 Listing Image for 130 Kai Malina Pkwy 719 22 of 33 Listing Image for 130 Kai Malina Pkwy 719 23 of 33 Listing Image for 130 Kai Malina Pkwy 719 24 of 33 Listing Image for 130 Kai Malina Pkwy 719 25 of 33 Listing Image for 130 Kai Malina Pkwy 719 26 of 33 Listing Image for 130 Kai Malina Pkwy 719 27 of 33 Listing Image for 130 Kai Malina Pkwy 719 28 of 33 Listing Image for 130 Kai Malina Pkwy 719 29 of 33 Listing Image for 130 Kai Malina Pkwy 719 30 of 33 Listing Image for 130 Kai Malina Pkwy 719 31 of 33 Listing Image for 130 Kai Malina Pkwy 719 32 of 33 Listing Image for 130 Kai Malina Pkwy 719 33 of 33

$1,125,000

↓ $63,000

Honua Kai - Hoku Lani 719

130 Kai Malina Pkwy 719, Kaanapali

0 Beds 1 Bath 595 SqFt Residential MLS® # 409778

Days on Market: 106

Maui Real Estate Advisors LLC 808-875-4444

Short Term Rental
Listing Image for 10 Wailea Ekolu Pl 1204 1 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 2 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 3 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 4 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 5 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 6 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 7 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 8 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 9 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 10 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 11 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 12 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 13 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 14 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 15 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 16 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 17 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 18 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 19 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 20 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 21 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 22 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 23 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 24 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 25 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 26 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 27 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 28 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 29 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 30 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 31 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 32 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 33 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 34 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 35 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 36 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 37 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 38 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 39 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 40 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 41 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 42 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 43 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 44 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 45 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 46 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 47 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 48 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 49 of 50 Listing Image for 10 Wailea Ekolu Pl 1204 50 of 50

$1,199,000

Wailea Ekolu 1204

10 Wailea Ekolu Pl 1204, Wailea/Makena

1 Bed 2 Baths 866 SqFt Residential MLS® # 409776

Days on Market: 106

Coldwell Banker Island Prop(S) Cell: 808-891-8989

View 7 More Listings

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: 04/16/2026
Listing Image for 52 Leipapa Pl 1 of 26 Listing Image for 52 Leipapa Pl 2 of 26 Listing Image for 52 Leipapa Pl 3 of 26 Listing Image for 52 Leipapa Pl 4 of 26 Listing Image for 52 Leipapa Pl 5 of 26 Listing Image for 52 Leipapa Pl 6 of 26 Listing Image for 52 Leipapa Pl 7 of 26 Listing Image for 52 Leipapa Pl 8 of 26 Listing Image for 52 Leipapa Pl 9 of 26 Listing Image for 52 Leipapa Pl 10 of 26 Listing Image for 52 Leipapa Pl 11 of 26 Listing Image for 52 Leipapa Pl 12 of 26 Listing Image for 52 Leipapa Pl 13 of 26 Listing Image for 52 Leipapa Pl 14 of 26 Listing Image for 52 Leipapa Pl 15 of 26 Listing Image for 52 Leipapa Pl 16 of 26 Listing Image for 52 Leipapa Pl 17 of 26 Listing Image for 52 Leipapa Pl 18 of 26 Listing Image for 52 Leipapa Pl 19 of 26 Listing Image for 52 Leipapa Pl 20 of 26 Listing Image for 52 Leipapa Pl 21 of 26 Listing Image for 52 Leipapa Pl 22 of 26 Listing Image for 52 Leipapa Pl 23 of 26 Listing Image for 52 Leipapa Pl 24 of 26 Listing Image for 52 Leipapa Pl 25 of 26 Listing Image for 52 Leipapa Pl 26 of 26

$1,010,000

Kahului

52 Leipapa Pl, Kahului

3 Beds 2 Baths 1,224 SqFt Residential MLS® # 408507 Date Sold: April 16, 2026
Sold
Closed: 03/16/2026
Listing Image for 19 Pa'alae Pl 1 of 50 Listing Image for 19 Pa'alae Pl 2 of 50 Listing Image for 19 Pa'alae Pl 3 of 50 Listing Image for 19 Pa'alae Pl 4 of 50 Listing Image for 19 Pa'alae Pl 5 of 50 Listing Image for 19 Pa'alae Pl 6 of 50 Listing Image for 19 Pa'alae Pl 7 of 50 Listing Image for 19 Pa'alae Pl 8 of 50 Listing Image for 19 Pa'alae Pl 9 of 50 Listing Image for 19 Pa'alae Pl 10 of 50 Listing Image for 19 Pa'alae Pl 11 of 50 Listing Image for 19 Pa'alae Pl 12 of 50 Listing Image for 19 Pa'alae Pl 13 of 50 Listing Image for 19 Pa'alae Pl 14 of 50 Listing Image for 19 Pa'alae Pl 15 of 50 Listing Image for 19 Pa'alae Pl 16 of 50 Listing Image for 19 Pa'alae Pl 17 of 50 Listing Image for 19 Pa'alae Pl 18 of 50 Listing Image for 19 Pa'alae Pl 19 of 50 Listing Image for 19 Pa'alae Pl 20 of 50 Listing Image for 19 Pa'alae Pl 21 of 50 Listing Image for 19 Pa'alae Pl 22 of 50 Listing Image for 19 Pa'alae Pl 23 of 50 Listing Image for 19 Pa'alae Pl 24 of 50 Listing Image for 19 Pa'alae Pl 25 of 50 Listing Image for 19 Pa'alae Pl 26 of 50 Listing Image for 19 Pa'alae Pl 27 of 50 Listing Image for 19 Pa'alae Pl 28 of 50 Listing Image for 19 Pa'alae Pl 29 of 50 Listing Image for 19 Pa'alae Pl 30 of 50 Listing Image for 19 Pa'alae Pl 31 of 50 Listing Image for 19 Pa'alae Pl 32 of 50 Listing Image for 19 Pa'alae Pl 33 of 50 Listing Image for 19 Pa'alae Pl 34 of 50 Listing Image for 19 Pa'alae Pl 35 of 50 Listing Image for 19 Pa'alae Pl 36 of 50 Listing Image for 19 Pa'alae Pl 37 of 50 Listing Image for 19 Pa'alae Pl 38 of 50 Listing Image for 19 Pa'alae Pl 39 of 50 Listing Image for 19 Pa'alae Pl 40 of 50 Listing Image for 19 Pa'alae Pl 41 of 50 Listing Image for 19 Pa'alae Pl 42 of 50 Listing Image for 19 Pa'alae Pl 43 of 50 Listing Image for 19 Pa'alae Pl 44 of 50 Listing Image for 19 Pa'alae Pl 45 of 50 Listing Image for 19 Pa'alae Pl 46 of 50 Listing Image for 19 Pa'alae Pl 47 of 50 Listing Image for 19 Pa'alae Pl 48 of 50 Listing Image for 19 Pa'alae Pl 49 of 50 Listing Image for 19 Pa'alae Pl 50 of 50

$1,600,000

Koa at Kehalani

19 Pa'alae Pl, Wailuku

4 Beds 3 Baths 2,576 SqFt Residential MLS® # 408504 Date Sold: March 16, 2026
Sold
Closed: 07/16/2026
Listing Image for 91 Lunalilo St 1 of 22 Listing Image for 91 Lunalilo St 2 of 22 Listing Image for 91 Lunalilo St 3 of 22 Listing Image for 91 Lunalilo St 4 of 22 Listing Image for 91 Lunalilo St 5 of 22 Listing Image for 91 Lunalilo St 6 of 22 Listing Image for 91 Lunalilo St 7 of 22 Listing Image for 91 Lunalilo St 8 of 22 Listing Image for 91 Lunalilo St 9 of 22 Listing Image for 91 Lunalilo St 10 of 22 Listing Image for 91 Lunalilo St 11 of 22 Listing Image for 91 Lunalilo St 12 of 22 Listing Image for 91 Lunalilo St 13 of 22 Listing Image for 91 Lunalilo St 14 of 22 Listing Image for 91 Lunalilo St 15 of 22 Listing Image for 91 Lunalilo St 16 of 22 Listing Image for 91 Lunalilo St 17 of 22 Listing Image for 91 Lunalilo St 18 of 22 Listing Image for 91 Lunalilo St 19 of 22 Listing Image for 91 Lunalilo St 20 of 22 Listing Image for 91 Lunalilo St 21 of 22 Listing Image for 91 Lunalilo St 22 of 22

$1,200,000

↓ $149,000

Sandhills

91 Lunalilo St, Wailuku

3 Beds 2 Baths 2,446 SqFt Residential MLS® # 404611 Date Sold: July 16, 2026
Sold
Closed: 03/31/2026
Listing Image for 15 Awikiwiki Pl 1 of 30 Listing Image for 15 Awikiwiki Pl 2 of 30 Listing Image for 15 Awikiwiki Pl 3 of 30 Listing Image for 15 Awikiwiki Pl 4 of 30 Listing Image for 15 Awikiwiki Pl 5 of 30 Listing Image for 15 Awikiwiki Pl 6 of 30 Listing Image for 15 Awikiwiki Pl 7 of 30 Listing Image for 15 Awikiwiki Pl 8 of 30 Listing Image for 15 Awikiwiki Pl 9 of 30 Listing Image for 15 Awikiwiki Pl 10 of 30 Listing Image for 15 Awikiwiki Pl 11 of 30 Listing Image for 15 Awikiwiki Pl 12 of 30 Listing Image for 15 Awikiwiki Pl 13 of 30 Listing Image for 15 Awikiwiki Pl 14 of 30 Listing Image for 15 Awikiwiki Pl 15 of 30 Listing Image for 15 Awikiwiki Pl 16 of 30 Listing Image for 15 Awikiwiki Pl 17 of 30 Listing Image for 15 Awikiwiki Pl 18 of 30 Listing Image for 15 Awikiwiki Pl 19 of 30 Listing Image for 15 Awikiwiki Pl 20 of 30 Listing Image for 15 Awikiwiki Pl 21 of 30 Listing Image for 15 Awikiwiki Pl 22 of 30 Listing Image for 15 Awikiwiki Pl 23 of 30 Listing Image for 15 Awikiwiki Pl 24 of 30 Listing Image for 15 Awikiwiki Pl 25 of 30 Listing Image for 15 Awikiwiki Pl 26 of 30 Listing Image for 15 Awikiwiki Pl 27 of 30 Listing Image for 15 Awikiwiki Pl 28 of 30 Listing Image for 15 Awikiwiki Pl 29 of 30 Listing Image for 15 Awikiwiki Pl 30 of 30

$1,145,000

↑ $20,000

Ohia at Kehalani

15 Awikiwiki Pl, Wailuku

3 Beds 2.5 Baths 1,766 SqFt Residential MLS® # 408499 Date Sold: March 31, 2026
Sold
Closed: 04/30/2026
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$1,429,000

↓ $266,000

Kihei

95 Ohukai Rd, Kihei

8 Beds 2 Baths 3,856 SqFt Residential Income MLS® # 408498 Date Sold: April 30, 2026
Sold
Closed: 01/21/2026
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$1,225,000

Kahului

122 E Papa Ave, Kahului

3 Beds 2 Baths 1,165 SqFt Residential MLS® # 408497 Date Sold: January 21, 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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