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 2695 S Kihei Rd 5-205 1 of 43 Listing Image for 2695 S Kihei Rd 5-205 2 of 43 Listing Image for 2695 S Kihei Rd 5-205 3 of 43 Listing Image for 2695 S Kihei Rd 5-205 4 of 43 Listing Image for 2695 S Kihei Rd 5-205 5 of 43 Listing Image for 2695 S Kihei Rd 5-205 6 of 43 Listing Image for 2695 S Kihei Rd 5-205 7 of 43 Listing Image for 2695 S Kihei Rd 5-205 8 of 43 Listing Image for 2695 S Kihei Rd 5-205 9 of 43 Listing Image for 2695 S Kihei Rd 5-205 10 of 43 Listing Image for 2695 S Kihei Rd 5-205 11 of 43 Listing Image for 2695 S Kihei Rd 5-205 12 of 43 Listing Image for 2695 S Kihei Rd 5-205 13 of 43 Listing Image for 2695 S Kihei Rd 5-205 14 of 43 Listing Image for 2695 S Kihei Rd 5-205 15 of 43 Listing Image for 2695 S Kihei Rd 5-205 16 of 43 Listing Image for 2695 S Kihei Rd 5-205 17 of 43 Listing Image for 2695 S Kihei Rd 5-205 18 of 43 Listing Image for 2695 S Kihei Rd 5-205 19 of 43 Listing Image for 2695 S Kihei Rd 5-205 20 of 43 Listing Image for 2695 S Kihei Rd 5-205 21 of 43 Listing Image for 2695 S Kihei Rd 5-205 22 of 43 Listing Image for 2695 S Kihei Rd 5-205 23 of 43 Listing Image for 2695 S Kihei Rd 5-205 24 of 43 Listing Image for 2695 S Kihei Rd 5-205 25 of 43 Listing Image for 2695 S Kihei Rd 5-205 26 of 43 Listing Image for 2695 S Kihei Rd 5-205 27 of 43 Listing Image for 2695 S Kihei Rd 5-205 28 of 43 Listing Image for 2695 S Kihei Rd 5-205 29 of 43 Listing Image for 2695 S Kihei Rd 5-205 30 of 43 Listing Image for 2695 S Kihei Rd 5-205 31 of 43 Listing Image for 2695 S Kihei Rd 5-205 32 of 43 Listing Image for 2695 S Kihei Rd 5-205 33 of 43 Listing Image for 2695 S Kihei Rd 5-205 34 of 43 Listing Image for 2695 S Kihei Rd 5-205 35 of 43 Listing Image for 2695 S Kihei Rd 5-205 36 of 43 Listing Image for 2695 S Kihei Rd 5-205 37 of 43 Listing Image for 2695 S Kihei Rd 5-205 38 of 43 Listing Image for 2695 S Kihei Rd 5-205 39 of 43 Listing Image for 2695 S Kihei Rd 5-205 40 of 43 Listing Image for 2695 S Kihei Rd 5-205 41 of 43 Listing Image for 2695 S Kihei Rd 5-205 42 of 43 Listing Image for 2695 S Kihei Rd 5-205 43 of 43

$999,900

Kamaole Sands 5-205

2695 S Kihei Rd 5-205, Kihei

2 Beds 2 Baths 1,036 SqFt Residential MLS® # 406856

Days on Market: 395

Coldwell Banker Island Prop(S) Cell: 808-344-0180

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

$15,000,000

Olowalu Makai Komohana

49 Kuahulu Pl Lot 4-c, Olowalu

3 Beds 3.5 Baths 3,477 SqFt Residential MLS® # 410537

Days on Market: 29

Coldwell Banker Island Prop-KP Cell: 808-280-2255

Short Term Rental
Listing Image for 110 Kaanapali Shores Pl 102 1 of 29 Listing Image for 110 Kaanapali Shores Pl 102 2 of 29 Listing Image for 110 Kaanapali Shores Pl 102 3 of 29 Listing Image for 110 Kaanapali Shores Pl 102 4 of 29 Listing Image for 110 Kaanapali Shores Pl 102 5 of 29 Listing Image for 110 Kaanapali Shores Pl 102 6 of 29 Listing Image for 110 Kaanapali Shores Pl 102 7 of 29 Listing Image for 110 Kaanapali Shores Pl 102 8 of 29 Listing Image for 110 Kaanapali Shores Pl 102 9 of 29 Listing Image for 110 Kaanapali Shores Pl 102 10 of 29 Listing Image for 110 Kaanapali Shores Pl 102 11 of 29 Listing Image for 110 Kaanapali Shores Pl 102 12 of 29 Listing Image for 110 Kaanapali Shores Pl 102 13 of 29 Listing Image for 110 Kaanapali Shores Pl 102 14 of 29 Listing Image for 110 Kaanapali Shores Pl 102 15 of 29 Listing Image for 110 Kaanapali Shores Pl 102 16 of 29 Listing Image for 110 Kaanapali Shores Pl 102 17 of 29 Listing Image for 110 Kaanapali Shores Pl 102 18 of 29 Listing Image for 110 Kaanapali Shores Pl 102 19 of 29 Listing Image for 110 Kaanapali Shores Pl 102 20 of 29 Listing Image for 110 Kaanapali Shores Pl 102 21 of 29 Listing Image for 110 Kaanapali Shores Pl 102 22 of 29 Listing Image for 110 Kaanapali Shores Pl 102 23 of 29 Listing Image for 110 Kaanapali Shores Pl 102 24 of 29 Listing Image for 110 Kaanapali Shores Pl 102 25 of 29 Listing Image for 110 Kaanapali Shores Pl 102 26 of 29 Listing Image for 110 Kaanapali Shores Pl 102 27 of 29 Listing Image for 110 Kaanapali Shores Pl 102 28 of 29 Listing Image for 110 Kaanapali Shores Pl 102 29 of 29

$875,000

Mahana 102

110 Kaanapali Shores Pl 102, Kaanapali

0 Beds 1 Bath 456 SqFt Residential MLS® # 410531

Days on Market: 30

Platinum Properties Hawaii,LLC

Listing Image for 832 Mahealani St 1 of 50 Listing Image for 832 Mahealani St 2 of 50 Listing Image for 832 Mahealani St 3 of 50 Listing Image for 832 Mahealani St 4 of 50 Listing Image for 832 Mahealani St 5 of 50 Listing Image for 832 Mahealani St 6 of 50 Listing Image for 832 Mahealani St 7 of 50 Listing Image for 832 Mahealani St 8 of 50 Listing Image for 832 Mahealani St 9 of 50 Listing Image for 832 Mahealani St 10 of 50 Listing Image for 832 Mahealani St 11 of 50 Listing Image for 832 Mahealani St 12 of 50 Listing Image for 832 Mahealani St 13 of 50 Listing Image for 832 Mahealani St 14 of 50 Listing Image for 832 Mahealani St 15 of 50 Listing Image for 832 Mahealani St 16 of 50 Listing Image for 832 Mahealani St 17 of 50 Listing Image for 832 Mahealani St 18 of 50 Listing Image for 832 Mahealani St 19 of 50 Listing Image for 832 Mahealani St 20 of 50 Listing Image for 832 Mahealani St 21 of 50 Listing Image for 832 Mahealani St 22 of 50 Listing Image for 832 Mahealani St 23 of 50 Listing Image for 832 Mahealani St 24 of 50 Listing Image for 832 Mahealani St 25 of 50 Listing Image for 832 Mahealani St 26 of 50 Listing Image for 832 Mahealani St 27 of 50 Listing Image for 832 Mahealani St 28 of 50 Listing Image for 832 Mahealani St 29 of 50 Listing Image for 832 Mahealani St 30 of 50 Listing Image for 832 Mahealani St 31 of 50 Listing Image for 832 Mahealani St 32 of 50 Listing Image for 832 Mahealani St 33 of 50 Listing Image for 832 Mahealani St 34 of 50 Listing Image for 832 Mahealani St 35 of 50 Listing Image for 832 Mahealani St 36 of 50 Listing Image for 832 Mahealani St 37 of 50 Listing Image for 832 Mahealani St 38 of 50 Listing Image for 832 Mahealani St 39 of 50 Listing Image for 832 Mahealani St 40 of 50 Listing Image for 832 Mahealani St 41 of 50 Listing Image for 832 Mahealani St 42 of 50 Listing Image for 832 Mahealani St 43 of 50 Listing Image for 832 Mahealani St 44 of 50 Listing Image for 832 Mahealani St 45 of 50 Listing Image for 832 Mahealani St 46 of 50 Listing Image for 832 Mahealani St 47 of 50 Listing Image for 832 Mahealani St 48 of 50 Listing Image for 832 Mahealani St 49 of 50 Listing Image for 832 Mahealani St 50 of 50

$1,100,000

Piilani Villages I

832 Mahealani St, Kihei

3 Beds 2.5 Baths 1,591 SqFt Residential MLS® # 410528

Days on Market: 30

ENRG Realty

Listing Image for 3111 Waiea Pl 1 of 41 Listing Image for 3111 Waiea Pl 2 of 41 Listing Image for 3111 Waiea Pl 3 of 41 Listing Image for 3111 Waiea Pl 4 of 41 Listing Image for 3111 Waiea Pl 5 of 41 Listing Image for 3111 Waiea Pl 6 of 41 Listing Image for 3111 Waiea Pl 7 of 41 Listing Image for 3111 Waiea Pl 8 of 41 Listing Image for 3111 Waiea Pl 9 of 41 Listing Image for 3111 Waiea Pl 10 of 41 Listing Image for 3111 Waiea Pl 11 of 41 Listing Image for 3111 Waiea Pl 12 of 41 Listing Image for 3111 Waiea Pl 13 of 41 Listing Image for 3111 Waiea Pl 14 of 41 Listing Image for 3111 Waiea Pl 15 of 41 Listing Image for 3111 Waiea Pl 16 of 41 Listing Image for 3111 Waiea Pl 17 of 41 Listing Image for 3111 Waiea Pl 18 of 41 Listing Image for 3111 Waiea Pl 19 of 41 Listing Image for 3111 Waiea Pl 20 of 41 Listing Image for 3111 Waiea Pl 21 of 41 Listing Image for 3111 Waiea Pl 22 of 41 Listing Image for 3111 Waiea Pl 23 of 41 Listing Image for 3111 Waiea Pl 24 of 41 Listing Image for 3111 Waiea Pl 25 of 41 Listing Image for 3111 Waiea Pl 26 of 41 Listing Image for 3111 Waiea Pl 27 of 41 Listing Image for 3111 Waiea Pl 28 of 41 Listing Image for 3111 Waiea Pl 29 of 41 Listing Image for 3111 Waiea Pl 30 of 41 Listing Image for 3111 Waiea Pl 31 of 41 Listing Image for 3111 Waiea Pl 32 of 41 Listing Image for 3111 Waiea Pl 33 of 41 Listing Image for 3111 Waiea Pl 34 of 41 Listing Image for 3111 Waiea Pl 35 of 41 Listing Image for 3111 Waiea Pl 36 of 41 Listing Image for 3111 Waiea Pl 37 of 41 Listing Image for 3111 Waiea Pl 38 of 41 Listing Image for 3111 Waiea Pl 39 of 41 Listing Image for 3111 Waiea Pl 40 of 41 Listing Image for 3111 Waiea Pl 41 of 41

$2,500,000

Wailea Kai

3111 Waiea Pl, Wailea/Makena

3 Beds 3 Baths 1,797 SqFt Residential MLS® # 410525

Days on Market: 30

Maui Luxury Real Estate LLC

Listing Image for 2757 S Kihei Rd 502 1 of 44 Listing Image for 2757 S Kihei Rd 502 2 of 44 Listing Image for 2757 S Kihei Rd 502 3 of 44 Listing Image for 2757 S Kihei Rd 502 4 of 44 Listing Image for 2757 S Kihei Rd 502 5 of 44 Listing Image for 2757 S Kihei Rd 502 6 of 44 Listing Image for 2757 S Kihei Rd 502 7 of 44 Listing Image for 2757 S Kihei Rd 502 8 of 44 Listing Image for 2757 S Kihei Rd 502 9 of 44 Listing Image for 2757 S Kihei Rd 502 10 of 44 Listing Image for 2757 S Kihei Rd 502 11 of 44 Listing Image for 2757 S Kihei Rd 502 12 of 44 Listing Image for 2757 S Kihei Rd 502 13 of 44 Listing Image for 2757 S Kihei Rd 502 14 of 44 Listing Image for 2757 S Kihei Rd 502 15 of 44 Listing Image for 2757 S Kihei Rd 502 16 of 44 Listing Image for 2757 S Kihei Rd 502 17 of 44 Listing Image for 2757 S Kihei Rd 502 18 of 44 Listing Image for 2757 S Kihei Rd 502 19 of 44 Listing Image for 2757 S Kihei Rd 502 20 of 44 Listing Image for 2757 S Kihei Rd 502 21 of 44 Listing Image for 2757 S Kihei Rd 502 22 of 44 Listing Image for 2757 S Kihei Rd 502 23 of 44 Listing Image for 2757 S Kihei Rd 502 24 of 44 Listing Image for 2757 S Kihei Rd 502 25 of 44 Listing Image for 2757 S Kihei Rd 502 26 of 44 Listing Image for 2757 S Kihei Rd 502 27 of 44 Listing Image for 2757 S Kihei Rd 502 28 of 44 Listing Image for 2757 S Kihei Rd 502 29 of 44 Listing Image for 2757 S Kihei Rd 502 30 of 44 Listing Image for 2757 S Kihei Rd 502 31 of 44 Listing Image for 2757 S Kihei Rd 502 32 of 44 Listing Image for 2757 S Kihei Rd 502 33 of 44 Listing Image for 2757 S Kihei Rd 502 34 of 44 Listing Image for 2757 S Kihei Rd 502 35 of 44 Listing Image for 2757 S Kihei Rd 502 36 of 44 Listing Image for 2757 S Kihei Rd 502 37 of 44 Listing Image for 2757 S Kihei Rd 502 38 of 44 Listing Image for 2757 S Kihei Rd 502 39 of 44 Listing Image for 2757 S Kihei Rd 502 40 of 44 Listing Image for 2757 S Kihei Rd 502 41 of 44 Listing Image for 2757 S Kihei Rd 502 42 of 44 Listing Image for 2757 S Kihei Rd 502 43 of 44 Listing Image for 2757 S Kihei Rd 502 44 of 44

$1,299,000

Paradise Ridge Estates 502

2757 S Kihei Rd 502, Kihei

2 Beds 2 Baths 1,251 SqFt Residential MLS® # 410523

Days on Market: 30

Coldwell Banker Island Prop(S) Cell: 808-870-4899

View 6 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: 09/09/2026
Listing Image for 110 Kaanapali Shores Pl 214 1 of 30 Listing Image for 110 Kaanapali Shores Pl 214 2 of 30 Listing Image for 110 Kaanapali Shores Pl 214 3 of 30 Listing Image for 110 Kaanapali Shores Pl 214 4 of 30 Listing Image for 110 Kaanapali Shores Pl 214 5 of 30 Listing Image for 110 Kaanapali Shores Pl 214 6 of 30 Listing Image for 110 Kaanapali Shores Pl 214 7 of 30 Listing Image for 110 Kaanapali Shores Pl 214 8 of 30 Listing Image for 110 Kaanapali Shores Pl 214 9 of 30 Listing Image for 110 Kaanapali Shores Pl 214 10 of 30 Listing Image for 110 Kaanapali Shores Pl 214 11 of 30 Listing Image for 110 Kaanapali Shores Pl 214 12 of 30 Listing Image for 110 Kaanapali Shores Pl 214 13 of 30 Listing Image for 110 Kaanapali Shores Pl 214 14 of 30 Listing Image for 110 Kaanapali Shores Pl 214 15 of 30 Listing Image for 110 Kaanapali Shores Pl 214 16 of 30 Listing Image for 110 Kaanapali Shores Pl 214 17 of 30 Listing Image for 110 Kaanapali Shores Pl 214 18 of 30 Listing Image for 110 Kaanapali Shores Pl 214 19 of 30 Listing Image for 110 Kaanapali Shores Pl 214 20 of 30 Listing Image for 110 Kaanapali Shores Pl 214 21 of 30 Listing Image for 110 Kaanapali Shores Pl 214 22 of 30 Listing Image for 110 Kaanapali Shores Pl 214 23 of 30 Listing Image for 110 Kaanapali Shores Pl 214 24 of 30 Listing Image for 110 Kaanapali Shores Pl 214 25 of 30 Listing Image for 110 Kaanapali Shores Pl 214 26 of 30 Listing Image for 110 Kaanapali Shores Pl 214 27 of 30 Listing Image for 110 Kaanapali Shores Pl 214 28 of 30 Listing Image for 110 Kaanapali Shores Pl 214 29 of 30 Listing Image for 110 Kaanapali Shores Pl 214 30 of 30

$934,250

Mahana 214

110 Kaanapali Shores Pl 214, Napili/Kahana/Honokowai

1 Bed 1 Bath 820 SqFt Residential MLS® # 409658 Date Sold: September 9, 2026
Sold
Closed: 07/17/2026
Listing Image for 107 E Makaukau Loop 1 of 36 Listing Image for 107 E Makaukau Loop 2 of 36 Listing Image for 107 E Makaukau Loop 3 of 36 Listing Image for 107 E Makaukau Loop 4 of 36 Listing Image for 107 E Makaukau Loop 5 of 36 Listing Image for 107 E Makaukau Loop 6 of 36 Listing Image for 107 E Makaukau Loop 7 of 36 Listing Image for 107 E Makaukau Loop 8 of 36 Listing Image for 107 E Makaukau Loop 9 of 36 Listing Image for 107 E Makaukau Loop 10 of 36 Listing Image for 107 E Makaukau Loop 11 of 36 Listing Image for 107 E Makaukau Loop 12 of 36 Listing Image for 107 E Makaukau Loop 13 of 36 Listing Image for 107 E Makaukau Loop 14 of 36 Listing Image for 107 E Makaukau Loop 15 of 36 Listing Image for 107 E Makaukau Loop 16 of 36 Listing Image for 107 E Makaukau Loop 17 of 36 Listing Image for 107 E Makaukau Loop 18 of 36 Listing Image for 107 E Makaukau Loop 19 of 36 Listing Image for 107 E Makaukau Loop 20 of 36 Listing Image for 107 E Makaukau Loop 21 of 36 Listing Image for 107 E Makaukau Loop 22 of 36 Listing Image for 107 E Makaukau Loop 23 of 36 Listing Image for 107 E Makaukau Loop 24 of 36 Listing Image for 107 E Makaukau Loop 25 of 36 Listing Image for 107 E Makaukau Loop 26 of 36 Listing Image for 107 E Makaukau Loop 27 of 36 Listing Image for 107 E Makaukau Loop 28 of 36 Listing Image for 107 E Makaukau Loop 29 of 36 Listing Image for 107 E Makaukau Loop 30 of 36 Listing Image for 107 E Makaukau Loop 31 of 36 Listing Image for 107 E Makaukau Loop 32 of 36 Listing Image for 107 E Makaukau Loop 33 of 36 Listing Image for 107 E Makaukau Loop 34 of 36 Listing Image for 107 E Makaukau Loop 35 of 36 Listing Image for 107 E Makaukau Loop 36 of 36

$1,228,000

Waikapu Gardens

107 E Makaukau Loop, Wailuku

4 Beds 3 Baths 1,774 SqFt Residential MLS® # 409649 Date Sold: July 17, 2026
Sold
Closed: 06/22/2026
Listing Image for 2481 Kaanapali Pkwy 905 1 of 46 Listing Image for 2481 Kaanapali Pkwy 905 2 of 46 Listing Image for 2481 Kaanapali Pkwy 905 3 of 46 Listing Image for 2481 Kaanapali Pkwy 905 4 of 46 Listing Image for 2481 Kaanapali Pkwy 905 5 of 46 Listing Image for 2481 Kaanapali Pkwy 905 6 of 46 Listing Image for 2481 Kaanapali Pkwy 905 7 of 46 Listing Image for 2481 Kaanapali Pkwy 905 8 of 46 Listing Image for 2481 Kaanapali Pkwy 905 9 of 46 Listing Image for 2481 Kaanapali Pkwy 905 10 of 46 Listing Image for 2481 Kaanapali Pkwy 905 11 of 46 Listing Image for 2481 Kaanapali Pkwy 905 12 of 46 Listing Image for 2481 Kaanapali Pkwy 905 13 of 46 Listing Image for 2481 Kaanapali Pkwy 905 14 of 46 Listing Image for 2481 Kaanapali Pkwy 905 15 of 46 Listing Image for 2481 Kaanapali Pkwy 905 16 of 46 Listing Image for 2481 Kaanapali Pkwy 905 17 of 46 Listing Image for 2481 Kaanapali Pkwy 905 18 of 46 Listing Image for 2481 Kaanapali Pkwy 905 19 of 46 Listing Image for 2481 Kaanapali Pkwy 905 20 of 46 Listing Image for 2481 Kaanapali Pkwy 905 21 of 46 Listing Image for 2481 Kaanapali Pkwy 905 22 of 46 Listing Image for 2481 Kaanapali Pkwy 905 23 of 46 Listing Image for 2481 Kaanapali Pkwy 905 24 of 46 Listing Image for 2481 Kaanapali Pkwy 905 25 of 46 Listing Image for 2481 Kaanapali Pkwy 905 26 of 46 Listing Image for 2481 Kaanapali Pkwy 905 27 of 46 Listing Image for 2481 Kaanapali Pkwy 905 28 of 46 Listing Image for 2481 Kaanapali Pkwy 905 29 of 46 Listing Image for 2481 Kaanapali Pkwy 905 30 of 46 Listing Image for 2481 Kaanapali Pkwy 905 31 of 46 Listing Image for 2481 Kaanapali Pkwy 905 32 of 46 Listing Image for 2481 Kaanapali Pkwy 905 33 of 46 Listing Image for 2481 Kaanapali Pkwy 905 34 of 46 Listing Image for 2481 Kaanapali Pkwy 905 35 of 46 Listing Image for 2481 Kaanapali Pkwy 905 36 of 46 Listing Image for 2481 Kaanapali Pkwy 905 37 of 46 Listing Image for 2481 Kaanapali Pkwy 905 38 of 46 Listing Image for 2481 Kaanapali Pkwy 905 39 of 46 Listing Image for 2481 Kaanapali Pkwy 905 40 of 46 Listing Image for 2481 Kaanapali Pkwy 905 41 of 46 Listing Image for 2481 Kaanapali Pkwy 905 42 of 46 Listing Image for 2481 Kaanapali Pkwy 905 43 of 46 Listing Image for 2481 Kaanapali Pkwy 905 44 of 46 Listing Image for 2481 Kaanapali Pkwy 905 45 of 46 Listing Image for 2481 Kaanapali Pkwy 905 46 of 46

$1,800,000

Whaler 905

2481 Kaanapali Pkwy 905, Kaanapali

1 Bed 2 Baths 905 SqFt Residential MLS® # 407633 Date Sold: June 22, 2026
Sold
Closed: 05/15/2026
3600 Wailea Alanui Dr 1603, Wailea/Makena

$5,990,000

Wailea Elua 1603

3600 Wailea Alanui Dr 1603, Wailea/Makena

2 Beds 2 Baths 1,363 SqFt Residential MLS® # 409620 Date Sold: May 15, 2026
Sold
Closed: 07/06/2026
Listing Image for 3217 Luahine Pl 1 of 50 Listing Image for 3217 Luahine Pl 2 of 50 Listing Image for 3217 Luahine Pl 3 of 50 Listing Image for 3217 Luahine Pl 4 of 50 Listing Image for 3217 Luahine Pl 5 of 50 Listing Image for 3217 Luahine Pl 6 of 50 Listing Image for 3217 Luahine Pl 7 of 50 Listing Image for 3217 Luahine Pl 8 of 50 Listing Image for 3217 Luahine Pl 9 of 50 Listing Image for 3217 Luahine Pl 10 of 50 Listing Image for 3217 Luahine Pl 11 of 50 Listing Image for 3217 Luahine Pl 12 of 50 Listing Image for 3217 Luahine Pl 13 of 50 Listing Image for 3217 Luahine Pl 14 of 50 Listing Image for 3217 Luahine Pl 15 of 50 Listing Image for 3217 Luahine Pl 16 of 50 Listing Image for 3217 Luahine Pl 17 of 50 Listing Image for 3217 Luahine Pl 18 of 50 Listing Image for 3217 Luahine Pl 19 of 50 Listing Image for 3217 Luahine Pl 20 of 50 Listing Image for 3217 Luahine Pl 21 of 50 Listing Image for 3217 Luahine Pl 22 of 50 Listing Image for 3217 Luahine Pl 23 of 50 Listing Image for 3217 Luahine Pl 24 of 50 Listing Image for 3217 Luahine Pl 25 of 50 Listing Image for 3217 Luahine Pl 26 of 50 Listing Image for 3217 Luahine Pl 27 of 50 Listing Image for 3217 Luahine Pl 28 of 50 Listing Image for 3217 Luahine Pl 29 of 50 Listing Image for 3217 Luahine Pl 30 of 50 Listing Image for 3217 Luahine Pl 31 of 50 Listing Image for 3217 Luahine Pl 32 of 50 Listing Image for 3217 Luahine Pl 33 of 50 Listing Image for 3217 Luahine Pl 34 of 50 Listing Image for 3217 Luahine Pl 35 of 50 Listing Image for 3217 Luahine Pl 36 of 50 Listing Image for 3217 Luahine Pl 37 of 50 Listing Image for 3217 Luahine Pl 38 of 50 Listing Image for 3217 Luahine Pl 39 of 50 Listing Image for 3217 Luahine Pl 40 of 50 Listing Image for 3217 Luahine Pl 41 of 50 Listing Image for 3217 Luahine Pl 42 of 50 Listing Image for 3217 Luahine Pl 43 of 50 Listing Image for 3217 Luahine Pl 44 of 50 Listing Image for 3217 Luahine Pl 45 of 50 Listing Image for 3217 Luahine Pl 46 of 50 Listing Image for 3217 Luahine Pl 47 of 50 Listing Image for 3217 Luahine Pl 48 of 50 Listing Image for 3217 Luahine Pl 49 of 50 Listing Image for 3217 Luahine Pl 50 of 50

$1,185,800

Haiku Circle

3217 Luahine Pl, Haiku

3 Beds 1.5 Baths 1,120 SqFt Residential MLS® # 409618 Date Sold: July 6, 2026
Sold
Closed: 07/30/2026
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$1,132,000

Napili

35 Hui F Rd B, Napili/Kahana/Honokowai

3 Beds 1.5 Baths 1,416 SqFt Residential MLS® # 409617 Date Sold: July 30, 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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