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 161 Wailea Ike Pl C-203 1 of 29 Listing Image for 161 Wailea Ike Pl C-203 2 of 29 Listing Image for 161 Wailea Ike Pl C-203 3 of 29 Listing Image for 161 Wailea Ike Pl C-203 4 of 29 Listing Image for 161 Wailea Ike Pl C-203 5 of 29 Listing Image for 161 Wailea Ike Pl C-203 6 of 29 Listing Image for 161 Wailea Ike Pl C-203 7 of 29 Listing Image for 161 Wailea Ike Pl C-203 8 of 29 Listing Image for 161 Wailea Ike Pl C-203 9 of 29 Listing Image for 161 Wailea Ike Pl C-203 10 of 29 Listing Image for 161 Wailea Ike Pl C-203 11 of 29 Listing Image for 161 Wailea Ike Pl C-203 12 of 29 Listing Image for 161 Wailea Ike Pl C-203 13 of 29 Listing Image for 161 Wailea Ike Pl C-203 14 of 29 Listing Image for 161 Wailea Ike Pl C-203 15 of 29 Listing Image for 161 Wailea Ike Pl C-203 16 of 29 Listing Image for 161 Wailea Ike Pl C-203 17 of 29 Listing Image for 161 Wailea Ike Pl C-203 18 of 29 Listing Image for 161 Wailea Ike Pl C-203 19 of 29 Listing Image for 161 Wailea Ike Pl C-203 20 of 29 Listing Image for 161 Wailea Ike Pl C-203 21 of 29 Listing Image for 161 Wailea Ike Pl C-203 22 of 29 Listing Image for 161 Wailea Ike Pl C-203 23 of 29 Listing Image for 161 Wailea Ike Pl C-203 24 of 29 Listing Image for 161 Wailea Ike Pl C-203 25 of 29 Listing Image for 161 Wailea Ike Pl C-203 26 of 29 Listing Image for 161 Wailea Ike Pl C-203 27 of 29 Listing Image for 161 Wailea Ike Pl C-203 28 of 29 Listing Image for 161 Wailea Ike Pl C-203 29 of 29

$1,675,000

↓ $214,000

Wailea Town Center C-203

161 Wailea Ike Pl C-203, Wailea/Makena

3 Beds 3 Baths 1,910 SqFt Residential MLS® # 407834

Days on Market: 300

Maui Real Estate Advisors LLC 808-875-4444

Listing Image for 4000 Wailea Alanui Dr 1602 1 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 2 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 3 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 4 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 5 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 6 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 7 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 8 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 9 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 10 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 11 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 12 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 13 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 14 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 15 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 16 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 17 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 18 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 19 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 20 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 21 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 22 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 23 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 24 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 25 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 26 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 27 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 28 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 29 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 30 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 31 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 32 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 33 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 34 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 35 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 36 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 37 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 38 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 39 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 40 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 41 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 42 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 43 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 44 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 45 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 46 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 47 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 48 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 49 of 50 Listing Image for 4000 Wailea Alanui Dr 1602 50 of 50

$13,900,000

Wailea Point 1602

4000 Wailea Alanui Dr 1602, Wailea/Makena

3 Beds 3 Baths 3,850 SqFt Residential MLS® # 407829

Days on Market: 300

Wailea Point Realty, Inc. realty@waileapoint.com

Listing Image for 0 Kalua Koi Rd Lot 369 1 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 2 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 3 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 4 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 5 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 6 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 7 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 8 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 9 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 10 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 11 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 12 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 13 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 14 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 15 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 16 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 17 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 18 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 19 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 20 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 21 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 22 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 23 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 24 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 25 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 26 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 27 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 28 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 29 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 30 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 31 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 32 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 33 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 34 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 35 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 36 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 37 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 38 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 39 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 40 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 41 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 42 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 43 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 44 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 45 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 46 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 47 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 48 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 49 of 50 Listing Image for 0 Kalua Koi Rd Lot 369 50 of 50

$2,100,000

Papohaku Ranchland

0 Kalua Koi Rd Lot 369, Molokai

4 Beds 4 Baths 2,478 SqFt Residential MLS® # 407826

Days on Market: 301

Molokai Realty LLC Cell: 808-646-0837

Short Term Rental
Listing Image for 130 Kai Malina Pkwy Sr734 1 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 2 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 3 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 4 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 5 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 6 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 7 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 8 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 9 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 10 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 11 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 12 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 13 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 14 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 15 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 16 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 17 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 18 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 19 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 20 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 21 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 22 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 23 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 24 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 25 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 26 of 27 Listing Image for 130 Kai Malina Pkwy Sr734 27 of 27

$1,495,000

↓ $180,000

Honua Kai - Hoku Lani SR734

130 Kai Malina Pkwy Sr734, Kaanapali

2 Beds 2 Baths 1,080 SqFt Residential MLS® # 407798

Days on Market: 302

Island Sotheby's International Realty(M) Cell: 808-283-0049

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

$1,950,000

↓ $250,000

Haiku

44 Kaupakalua Rd, Haiku

4 Beds 2 Baths 1,920 SqFt Residential MLS® # 407795

Days on Market: 306

Five Star Realty Inc.

Listing Image for 206 Awawa Rd 1 of 29 Listing Image for 206 Awawa Rd 2 of 29 Listing Image for 206 Awawa Rd 3 of 29 Listing Image for 206 Awawa Rd 4 of 29 Listing Image for 206 Awawa Rd 5 of 29 Listing Image for 206 Awawa Rd 6 of 29 Listing Image for 206 Awawa Rd 7 of 29 Listing Image for 206 Awawa Rd 8 of 29 Listing Image for 206 Awawa Rd 9 of 29 Listing Image for 206 Awawa Rd 10 of 29 Listing Image for 206 Awawa Rd 11 of 29 Listing Image for 206 Awawa Rd 12 of 29 Listing Image for 206 Awawa Rd 13 of 29 Listing Image for 206 Awawa Rd 14 of 29 Listing Image for 206 Awawa Rd 15 of 29 Listing Image for 206 Awawa Rd 16 of 29 Listing Image for 206 Awawa Rd 17 of 29 Listing Image for 206 Awawa Rd 18 of 29 Listing Image for 206 Awawa Rd 19 of 29 Listing Image for 206 Awawa Rd 20 of 29 Listing Image for 206 Awawa Rd 21 of 29 Listing Image for 206 Awawa Rd 22 of 29 Listing Image for 206 Awawa Rd 23 of 29 Listing Image for 206 Awawa Rd 24 of 29 Listing Image for 206 Awawa Rd 25 of 29 Listing Image for 206 Awawa Rd 26 of 29 Listing Image for 206 Awawa Rd 27 of 29 Listing Image for 206 Awawa Rd 28 of 29 Listing Image for 206 Awawa Rd 29 of 29

$1,188,000

Molokai

206 Awawa Rd, Molokai

3 Beds 3 Baths 1,920 SqFt Residential MLS® # 400126

Days on Market: 1051

Jeffrey Samuels Realty

Listing Image for 124 Unahe Pl Lot 2-a 1 of 24 Listing Image for 124 Unahe Pl Lot 2-a 2 of 24 Listing Image for 124 Unahe Pl Lot 2-a 3 of 24 Listing Image for 124 Unahe Pl Lot 2-a 4 of 24 Listing Image for 124 Unahe Pl Lot 2-a 5 of 24 Listing Image for 124 Unahe Pl Lot 2-a 6 of 24 Listing Image for 124 Unahe Pl Lot 2-a 7 of 24 Listing Image for 124 Unahe Pl Lot 2-a 8 of 24 Listing Image for 124 Unahe Pl Lot 2-a 9 of 24 Listing Image for 124 Unahe Pl Lot 2-a 10 of 24 Listing Image for 124 Unahe Pl Lot 2-a 11 of 24 Listing Image for 124 Unahe Pl Lot 2-a 12 of 24 Listing Image for 124 Unahe Pl Lot 2-a 13 of 24 Listing Image for 124 Unahe Pl Lot 2-a 14 of 24 Listing Image for 124 Unahe Pl Lot 2-a 15 of 24 Listing Image for 124 Unahe Pl Lot 2-a 16 of 24 Listing Image for 124 Unahe Pl Lot 2-a 17 of 24 Listing Image for 124 Unahe Pl Lot 2-a 18 of 24 Listing Image for 124 Unahe Pl Lot 2-a 19 of 24 Listing Image for 124 Unahe Pl Lot 2-a 20 of 24 Listing Image for 124 Unahe Pl Lot 2-a 21 of 24 Listing Image for 124 Unahe Pl Lot 2-a 22 of 24 Listing Image for 124 Unahe Pl Lot 2-a 23 of 24 Listing Image for 124 Unahe Pl Lot 2-a 24 of 24

$1,358,835

↓ $50,000

The Parkways at Maui Lani

124 Unahe Pl Lot 2-a, Kahului

3 Beds 2 Baths 1,596 SqFt Residential MLS® # 407751

Days on Market: 306

Towne Island Homes, Ltd

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: 05/14/2026
Listing Image for 229 Kili'o'opu St 1 of 42 Listing Image for 229 Kili'o'opu St 2 of 42 Listing Image for 229 Kili'o'opu St 3 of 42 Listing Image for 229 Kili'o'opu St 4 of 42 Listing Image for 229 Kili'o'opu St 5 of 42 Listing Image for 229 Kili'o'opu St 6 of 42 Listing Image for 229 Kili'o'opu St 7 of 42 Listing Image for 229 Kili'o'opu St 8 of 42 Listing Image for 229 Kili'o'opu St 9 of 42 Listing Image for 229 Kili'o'opu St 10 of 42 Listing Image for 229 Kili'o'opu St 11 of 42 Listing Image for 229 Kili'o'opu St 12 of 42 Listing Image for 229 Kili'o'opu St 13 of 42 Listing Image for 229 Kili'o'opu St 14 of 42 Listing Image for 229 Kili'o'opu St 15 of 42 Listing Image for 229 Kili'o'opu St 16 of 42 Listing Image for 229 Kili'o'opu St 17 of 42 Listing Image for 229 Kili'o'opu St 18 of 42 Listing Image for 229 Kili'o'opu St 19 of 42 Listing Image for 229 Kili'o'opu St 20 of 42 Listing Image for 229 Kili'o'opu St 21 of 42 Listing Image for 229 Kili'o'opu St 22 of 42 Listing Image for 229 Kili'o'opu St 23 of 42 Listing Image for 229 Kili'o'opu St 24 of 42 Listing Image for 229 Kili'o'opu St 25 of 42 Listing Image for 229 Kili'o'opu St 26 of 42 Listing Image for 229 Kili'o'opu St 27 of 42 Listing Image for 229 Kili'o'opu St 28 of 42 Listing Image for 229 Kili'o'opu St 29 of 42 Listing Image for 229 Kili'o'opu St 30 of 42 Listing Image for 229 Kili'o'opu St 31 of 42 Listing Image for 229 Kili'o'opu St 32 of 42 Listing Image for 229 Kili'o'opu St 33 of 42 Listing Image for 229 Kili'o'opu St 34 of 42 Listing Image for 229 Kili'o'opu St 35 of 42 Listing Image for 229 Kili'o'opu St 36 of 42 Listing Image for 229 Kili'o'opu St 37 of 42 Listing Image for 229 Kili'o'opu St 38 of 42 Listing Image for 229 Kili'o'opu St 39 of 42 Listing Image for 229 Kili'o'opu St 40 of 42 Listing Image for 229 Kili'o'opu St 41 of 42 Listing Image for 229 Kili'o'opu St 42 of 42

$1,190,000

↓ $40,000

Kehalani

229 Kili'o'opu St, Wailuku

3 Beds 2 Baths 1,508 SqFt Residential MLS® # 407238 Date Sold: May 14, 2026
Sold
Closed: 12/12/2025
Listing Image for 67 Kinohi Loa Loop 1 of 46 Listing Image for 67 Kinohi Loa Loop 2 of 46 Listing Image for 67 Kinohi Loa Loop 3 of 46 Listing Image for 67 Kinohi Loa Loop 4 of 46 Listing Image for 67 Kinohi Loa Loop 5 of 46 Listing Image for 67 Kinohi Loa Loop 6 of 46 Listing Image for 67 Kinohi Loa Loop 7 of 46 Listing Image for 67 Kinohi Loa Loop 8 of 46 Listing Image for 67 Kinohi Loa Loop 9 of 46 Listing Image for 67 Kinohi Loa Loop 10 of 46 Listing Image for 67 Kinohi Loa Loop 11 of 46 Listing Image for 67 Kinohi Loa Loop 12 of 46 Listing Image for 67 Kinohi Loa Loop 13 of 46 Listing Image for 67 Kinohi Loa Loop 14 of 46 Listing Image for 67 Kinohi Loa Loop 15 of 46 Listing Image for 67 Kinohi Loa Loop 16 of 46 Listing Image for 67 Kinohi Loa Loop 17 of 46 Listing Image for 67 Kinohi Loa Loop 18 of 46 Listing Image for 67 Kinohi Loa Loop 19 of 46 Listing Image for 67 Kinohi Loa Loop 20 of 46 Listing Image for 67 Kinohi Loa Loop 21 of 46 Listing Image for 67 Kinohi Loa Loop 22 of 46 Listing Image for 67 Kinohi Loa Loop 23 of 46 Listing Image for 67 Kinohi Loa Loop 24 of 46 Listing Image for 67 Kinohi Loa Loop 25 of 46 Listing Image for 67 Kinohi Loa Loop 26 of 46 Listing Image for 67 Kinohi Loa Loop 27 of 46 Listing Image for 67 Kinohi Loa Loop 28 of 46 Listing Image for 67 Kinohi Loa Loop 29 of 46 Listing Image for 67 Kinohi Loa Loop 30 of 46 Listing Image for 67 Kinohi Loa Loop 31 of 46 Listing Image for 67 Kinohi Loa Loop 32 of 46 Listing Image for 67 Kinohi Loa Loop 33 of 46 Listing Image for 67 Kinohi Loa Loop 34 of 46 Listing Image for 67 Kinohi Loa Loop 35 of 46 Listing Image for 67 Kinohi Loa Loop 36 of 46 Listing Image for 67 Kinohi Loa Loop 37 of 46 Listing Image for 67 Kinohi Loa Loop 38 of 46 Listing Image for 67 Kinohi Loa Loop 39 of 46 Listing Image for 67 Kinohi Loa Loop 40 of 46 Listing Image for 67 Kinohi Loa Loop 41 of 46 Listing Image for 67 Kinohi Loa Loop 42 of 46 Listing Image for 67 Kinohi Loa Loop 43 of 46 Listing Image for 67 Kinohi Loa Loop 44 of 46 Listing Image for 67 Kinohi Loa Loop 45 of 46 Listing Image for 67 Kinohi Loa Loop 46 of 46

$1,215,000

↓ $50,000

Akolea at Kehalani

67 Kinohi Loa Loop, Wailuku

3 Beds 2 Baths 1,676 SqFt Residential MLS® # 407237 Date Sold: December 12, 2025
Sold
Closed: 07/14/2026
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$1,800,000

↓ $195,000

Kanani Wailea 14

71 Poailani Pl 14, Wailea/Makena

3 Beds 2.5 Baths 2,229 SqFt Residential MLS® # 407235 Date Sold: July 14, 2026
Sold
Closed: 12/18/2025
Listing Image for 1500 Limahana Cir E101 1 of 21 Listing Image for 1500 Limahana Cir E101 2 of 21 Listing Image for 1500 Limahana Cir E101 3 of 21 Listing Image for 1500 Limahana Cir E101 4 of 21 Listing Image for 1500 Limahana Cir E101 5 of 21 Listing Image for 1500 Limahana Cir E101 6 of 21 Listing Image for 1500 Limahana Cir E101 7 of 21 Listing Image for 1500 Limahana Cir E101 8 of 21 Listing Image for 1500 Limahana Cir E101 9 of 21 Listing Image for 1500 Limahana Cir E101 10 of 21 Listing Image for 1500 Limahana Cir E101 11 of 21 Listing Image for 1500 Limahana Cir E101 12 of 21 Listing Image for 1500 Limahana Cir E101 13 of 21 Listing Image for 1500 Limahana Cir E101 14 of 21 Listing Image for 1500 Limahana Cir E101 15 of 21 Listing Image for 1500 Limahana Cir E101 16 of 21 Listing Image for 1500 Limahana Cir E101 17 of 21 Listing Image for 1500 Limahana Cir E101 18 of 21 Listing Image for 1500 Limahana Cir E101 19 of 21 Listing Image for 1500 Limahana Cir E101 20 of 21 Listing Image for 1500 Limahana Cir E101 21 of 21

$874,500

Opukea at Lahaina E101

1500 Limahana Cir E101, Lahaina

3 Beds 2 Baths 1,332 SqFt Residential MLS® # 407229 Date Sold: December 18, 2025
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
Sold
Closed: 09/24/2025
Listing Image for 216 Door Of Faith Rd 1 of 3 Listing Image for 216 Door Of Faith Rd 2 of 3 Listing Image for 216 Door Of Faith Rd 3 of 3

$900,000

Haiku

216 Door Of Faith Rd, Haiku

3 Beds 2 Baths 2,161 SqFt Residential MLS® # 407226 Date Sold: September 24, 2025
Sold
Closed: 01/26/2026
400 Palama Dr, Kahului

$1,000,000

Eighth Increment

400 Palama Dr, Kahului

4 Beds 3 Baths 1,808 SqFt Residential MLS® # 407223 Date Sold: January 26, 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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