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 A8 1 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 2 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 3 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 4 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 5 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 6 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 7 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 8 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 9 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 10 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 11 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 12 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 13 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 14 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 15 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 16 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 17 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 18 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 19 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 20 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 21 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 22 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 23 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 24 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 25 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 26 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 27 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 28 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 29 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 30 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 31 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 32 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 33 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 34 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 35 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 36 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 37 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 38 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 39 of 40 Listing Image for 4909 Lower Honoapiilani Rd A8 40 of 40

$1,225,000

↓ $124,000

Kahana Sunset A8

4909 Lower Honoapiilani Rd A8, Napili/Kahana/Honokowai

2 Beds 2.5 Baths 1,064 SqFt Residential MLS® # 404094

Days on Market: 664

Lilikoi Realty

Listing Image for 210 Naio Pl 1 of 45 Listing Image for 210 Naio Pl 2 of 45 Listing Image for 210 Naio Pl 3 of 45 Listing Image for 210 Naio Pl 4 of 45 Listing Image for 210 Naio Pl 5 of 45 Listing Image for 210 Naio Pl 6 of 45 Listing Image for 210 Naio Pl 7 of 45 Listing Image for 210 Naio Pl 8 of 45 Listing Image for 210 Naio Pl 9 of 45 Listing Image for 210 Naio Pl 10 of 45 Listing Image for 210 Naio Pl 11 of 45 Listing Image for 210 Naio Pl 12 of 45 Listing Image for 210 Naio Pl 13 of 45 Listing Image for 210 Naio Pl 14 of 45 Listing Image for 210 Naio Pl 15 of 45 Listing Image for 210 Naio Pl 16 of 45 Listing Image for 210 Naio Pl 17 of 45 Listing Image for 210 Naio Pl 18 of 45 Listing Image for 210 Naio Pl 19 of 45 Listing Image for 210 Naio Pl 20 of 45 Listing Image for 210 Naio Pl 21 of 45 Listing Image for 210 Naio Pl 22 of 45 Listing Image for 210 Naio Pl 23 of 45 Listing Image for 210 Naio Pl 24 of 45 Listing Image for 210 Naio Pl 25 of 45 Listing Image for 210 Naio Pl 26 of 45 Listing Image for 210 Naio Pl 27 of 45 Listing Image for 210 Naio Pl 28 of 45 Listing Image for 210 Naio Pl 29 of 45 Listing Image for 210 Naio Pl 30 of 45 Listing Image for 210 Naio Pl 31 of 45 Listing Image for 210 Naio Pl 32 of 45 Listing Image for 210 Naio Pl 33 of 45 Listing Image for 210 Naio Pl 34 of 45 Listing Image for 210 Naio Pl 35 of 45 Listing Image for 210 Naio Pl 36 of 45 Listing Image for 210 Naio Pl 37 of 45 Listing Image for 210 Naio Pl 38 of 45 Listing Image for 210 Naio Pl 39 of 45 Listing Image for 210 Naio Pl 40 of 45 Listing Image for 210 Naio Pl 41 of 45 Listing Image for 210 Naio Pl 42 of 45 Listing Image for 210 Naio Pl 43 of 45 Listing Image for 210 Naio Pl 44 of 45 Listing Image for 210 Naio Pl 45 of 45

$16,000,000

Mahana Estates

210 Naio Pl, Kapalua

4 Beds 4.5 Baths 4,720 SqFt Residential MLS® # 403334

Days on Market: 775

Island Sotheby's International Realty(L) Cell: 808-280-1080

Short Term Rental
Listing Image for 130 Kai Malina Pkwy 3c 1 of 39 Listing Image for 130 Kai Malina Pkwy 3c 2 of 39 Listing Image for 130 Kai Malina Pkwy 3c 3 of 39 Listing Image for 130 Kai Malina Pkwy 3c 4 of 39 Listing Image for 130 Kai Malina Pkwy 3c 5 of 39 Listing Image for 130 Kai Malina Pkwy 3c 6 of 39 Listing Image for 130 Kai Malina Pkwy 3c 7 of 39 Listing Image for 130 Kai Malina Pkwy 3c 8 of 39 Listing Image for 130 Kai Malina Pkwy 3c 9 of 39 Listing Image for 130 Kai Malina Pkwy 3c 10 of 39 Listing Image for 130 Kai Malina Pkwy 3c 11 of 39 Listing Image for 130 Kai Malina Pkwy 3c 12 of 39 Listing Image for 130 Kai Malina Pkwy 3c 13 of 39 Listing Image for 130 Kai Malina Pkwy 3c 14 of 39 Listing Image for 130 Kai Malina Pkwy 3c 15 of 39 Listing Image for 130 Kai Malina Pkwy 3c 16 of 39 Listing Image for 130 Kai Malina Pkwy 3c 17 of 39 Listing Image for 130 Kai Malina Pkwy 3c 18 of 39 Listing Image for 130 Kai Malina Pkwy 3c 19 of 39 Listing Image for 130 Kai Malina Pkwy 3c 20 of 39 Listing Image for 130 Kai Malina Pkwy 3c 21 of 39 Listing Image for 130 Kai Malina Pkwy 3c 22 of 39 Listing Image for 130 Kai Malina Pkwy 3c 23 of 39 Listing Image for 130 Kai Malina Pkwy 3c 24 of 39 Listing Image for 130 Kai Malina Pkwy 3c 25 of 39 Listing Image for 130 Kai Malina Pkwy 3c 26 of 39 Listing Image for 130 Kai Malina Pkwy 3c 27 of 39 Listing Image for 130 Kai Malina Pkwy 3c 28 of 39 Listing Image for 130 Kai Malina Pkwy 3c 29 of 39 Listing Image for 130 Kai Malina Pkwy 3c 30 of 39 Listing Image for 130 Kai Malina Pkwy 3c 31 of 39 Listing Image for 130 Kai Malina Pkwy 3c 32 of 39 Listing Image for 130 Kai Malina Pkwy 3c 33 of 39 Listing Image for 130 Kai Malina Pkwy 3c 34 of 39 Listing Image for 130 Kai Malina Pkwy 3c 35 of 39 Listing Image for 130 Kai Malina Pkwy 3c 36 of 39 Listing Image for 130 Kai Malina Pkwy 3c 37 of 39 Listing Image for 130 Kai Malina Pkwy 3c 38 of 39 Listing Image for 130 Kai Malina Pkwy 3c 39 of 39

$3,400,000

↓ $100,000

Honua Kai - Luana Garden Villas 3C

130 Kai Malina Pkwy 3c, Kaanapali

3 Beds 3 Baths 2,047 SqFt Residential MLS® # 404232

Days on Market: 652

Maui Westside Properties

Listing Image for 538 Akahi Pl 1 of 25 Listing Image for 538 Akahi Pl 2 of 25 Listing Image for 538 Akahi Pl 3 of 25 Listing Image for 538 Akahi Pl 4 of 25 Listing Image for 538 Akahi Pl 5 of 25 Listing Image for 538 Akahi Pl 6 of 25 Listing Image for 538 Akahi Pl 7 of 25 Listing Image for 538 Akahi Pl 8 of 25 Listing Image for 538 Akahi Pl 9 of 25 Listing Image for 538 Akahi Pl 10 of 25 Listing Image for 538 Akahi Pl 11 of 25 Listing Image for 538 Akahi Pl 12 of 25 Listing Image for 538 Akahi Pl 13 of 25 Listing Image for 538 Akahi Pl 14 of 25 Listing Image for 538 Akahi Pl 15 of 25 Listing Image for 538 Akahi Pl 16 of 25 Listing Image for 538 Akahi Pl 17 of 25 Listing Image for 538 Akahi Pl 18 of 25 Listing Image for 538 Akahi Pl 19 of 25 Listing Image for 538 Akahi Pl 20 of 25 Listing Image for 538 Akahi Pl 21 of 25 Listing Image for 538 Akahi Pl 22 of 25 Listing Image for 538 Akahi Pl 23 of 25 Listing Image for 538 Akahi Pl 24 of 25 Listing Image for 538 Akahi Pl 25 of 25

$899,000

↓ $251,000

Lanai

538 Akahi Pl, Lanai

4 Beds 2 Baths 1,120 SqFt Residential MLS® # 406064

Days on Market: 482

Hawaii Life (L) Cell: 415-302-9894

Buying Real Estate on Maui

Buying Real Estate on Maui

Read Evan's complete guide to buying a home or condo on Maui.

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In Escrow
Listing Image for 130 Kai Malina Pkwy Nr230 1 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 2 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 3 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 4 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 5 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 6 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 7 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 8 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 9 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 10 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 11 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 12 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 13 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 14 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 15 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 16 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 17 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 18 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 19 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 20 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 21 of 22 Listing Image for 130 Kai Malina Pkwy Nr230 22 of 22

$999,000

↓ $96,000

Honua Kai - Konea NR230

130 Kai Malina Pkwy Nr230, Kaanapali

1 Bed 1 Bath 615 SqFt Residential MLS® # 402184

Days on Market: 857

Susan Jackson Real Estate Cell: 865-206-1234

Short Term Rental
Listing Image for 130 Kai Malina Pkwy Nr202 1 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 2 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 3 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 4 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 5 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 6 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 7 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 8 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 9 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 10 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 11 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 12 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 13 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 14 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 15 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 16 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 17 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 18 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 19 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 20 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 21 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 22 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 23 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 24 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 25 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 26 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 27 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 28 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 29 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 30 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 31 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 32 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 33 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 34 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 35 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 36 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 37 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 38 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 39 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 40 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 41 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 42 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 43 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 44 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 45 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 46 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 47 of 48 Listing Image for 130 Kai Malina Pkwy Nr202 48 of 48

$4,950,000

↓ $450,000

Honua Kai - Konea NR202

130 Kai Malina Pkwy Nr202, Kaanapali

3 Beds 3 Baths 2,230 SqFt Residential MLS® # 406123

Days on Market: 474

Susan Jackson Real Estate Cell: 865-206-1234

Short Term Rental
Listing Image for 50 Nohea Kai Dr 1-201 1 of 50 Listing Image for 50 Nohea Kai Dr 1-201 2 of 50 Listing Image for 50 Nohea Kai Dr 1-201 3 of 50 Listing Image for 50 Nohea Kai Dr 1-201 4 of 50 Listing Image for 50 Nohea Kai Dr 1-201 5 of 50 Listing Image for 50 Nohea Kai Dr 1-201 6 of 50 Listing Image for 50 Nohea Kai Dr 1-201 7 of 50 Listing Image for 50 Nohea Kai Dr 1-201 8 of 50 Listing Image for 50 Nohea Kai Dr 1-201 9 of 50 Listing Image for 50 Nohea Kai Dr 1-201 10 of 50 Listing Image for 50 Nohea Kai Dr 1-201 11 of 50 Listing Image for 50 Nohea Kai Dr 1-201 12 of 50 Listing Image for 50 Nohea Kai Dr 1-201 13 of 50 Listing Image for 50 Nohea Kai Dr 1-201 14 of 50 Listing Image for 50 Nohea Kai Dr 1-201 15 of 50 Listing Image for 50 Nohea Kai Dr 1-201 16 of 50 Listing Image for 50 Nohea Kai Dr 1-201 17 of 50 Listing Image for 50 Nohea Kai Dr 1-201 18 of 50 Listing Image for 50 Nohea Kai Dr 1-201 19 of 50 Listing Image for 50 Nohea Kai Dr 1-201 20 of 50 Listing Image for 50 Nohea Kai Dr 1-201 21 of 50 Listing Image for 50 Nohea Kai Dr 1-201 22 of 50 Listing Image for 50 Nohea Kai Dr 1-201 23 of 50 Listing Image for 50 Nohea Kai Dr 1-201 24 of 50 Listing Image for 50 Nohea Kai Dr 1-201 25 of 50 Listing Image for 50 Nohea Kai Dr 1-201 26 of 50 Listing Image for 50 Nohea Kai Dr 1-201 27 of 50 Listing Image for 50 Nohea Kai Dr 1-201 28 of 50 Listing Image for 50 Nohea Kai Dr 1-201 29 of 50 Listing Image for 50 Nohea Kai Dr 1-201 30 of 50 Listing Image for 50 Nohea Kai Dr 1-201 31 of 50 Listing Image for 50 Nohea Kai Dr 1-201 32 of 50 Listing Image for 50 Nohea Kai Dr 1-201 33 of 50 Listing Image for 50 Nohea Kai Dr 1-201 34 of 50 Listing Image for 50 Nohea Kai Dr 1-201 35 of 50 Listing Image for 50 Nohea Kai Dr 1-201 36 of 50 Listing Image for 50 Nohea Kai Dr 1-201 37 of 50 Listing Image for 50 Nohea Kai Dr 1-201 38 of 50 Listing Image for 50 Nohea Kai Dr 1-201 39 of 50 Listing Image for 50 Nohea Kai Dr 1-201 40 of 50 Listing Image for 50 Nohea Kai Dr 1-201 41 of 50 Listing Image for 50 Nohea Kai Dr 1-201 42 of 50 Listing Image for 50 Nohea Kai Dr 1-201 43 of 50 Listing Image for 50 Nohea Kai Dr 1-201 44 of 50 Listing Image for 50 Nohea Kai Dr 1-201 45 of 50 Listing Image for 50 Nohea Kai Dr 1-201 46 of 50 Listing Image for 50 Nohea Kai Dr 1-201 47 of 50 Listing Image for 50 Nohea Kai Dr 1-201 48 of 50 Listing Image for 50 Nohea Kai Dr 1-201 49 of 50 Listing Image for 50 Nohea Kai Dr 1-201 50 of 50

$1,949,000

↓ $50,000

Kaanapali Alii 1-201

50 Nohea Kai Dr 1-201, Kaanapali

2 Beds 2 Baths 1,460 SqFt Residential MLS® # 403743

Days on Market: 701

Keller Williams Realty Maui-Ki Cell: 808-859-2086

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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: 10/30/2025
Listing Image for 2095 Lilikoi Rd 1 of 17 Listing Image for 2095 Lilikoi Rd 2 of 17 Listing Image for 2095 Lilikoi Rd 3 of 17 Listing Image for 2095 Lilikoi Rd 4 of 17 Listing Image for 2095 Lilikoi Rd 5 of 17 Listing Image for 2095 Lilikoi Rd 6 of 17 Listing Image for 2095 Lilikoi Rd 7 of 17 Listing Image for 2095 Lilikoi Rd 8 of 17 Listing Image for 2095 Lilikoi Rd 9 of 17 Listing Image for 2095 Lilikoi Rd 10 of 17 Listing Image for 2095 Lilikoi Rd 11 of 17 Listing Image for 2095 Lilikoi Rd 12 of 17 Listing Image for 2095 Lilikoi Rd 13 of 17 Listing Image for 2095 Lilikoi Rd 14 of 17 Listing Image for 2095 Lilikoi Rd 15 of 17 Listing Image for 2095 Lilikoi Rd 16 of 17 Listing Image for 2095 Lilikoi Rd 17 of 17

$1,200,000

Haiku

2095 Lilikoi Rd, Haiku

3 Beds 2 Baths 1,104 SqFt Residential MLS® # 406833 Date Sold: October 30, 2025
Sold
Closed: 01/26/2026
Listing Image for 3445 Lower Honoapiilani Rd 255 1 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 2 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 3 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 4 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 5 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 6 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 7 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 8 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 9 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 10 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 11 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 12 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 13 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 14 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 15 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 16 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 17 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 18 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 19 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 20 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 21 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 22 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 23 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 24 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 25 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 26 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 27 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 28 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 29 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 30 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 31 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 32 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 33 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 34 of 35 Listing Image for 3445 Lower Honoapiilani Rd 255 35 of 35

$900,000

↓ $219,000

Kaanapali Shores 255

3445 Lower Honoapiilani Rd 255, Kaanapali

2 Beds 2 Baths 1,078 SqFt Residential MLS® # 406863 Date Sold: January 26, 2026
Sold
Closed: 09/26/2025
Listing Image for 129 Molehulehu Loop 1 of 49 Listing Image for 129 Molehulehu Loop 2 of 49 Listing Image for 129 Molehulehu Loop 3 of 49 Listing Image for 129 Molehulehu Loop 4 of 49 Listing Image for 129 Molehulehu Loop 5 of 49 Listing Image for 129 Molehulehu Loop 6 of 49 Listing Image for 129 Molehulehu Loop 7 of 49 Listing Image for 129 Molehulehu Loop 8 of 49 Listing Image for 129 Molehulehu Loop 9 of 49 Listing Image for 129 Molehulehu Loop 10 of 49 Listing Image for 129 Molehulehu Loop 11 of 49 Listing Image for 129 Molehulehu Loop 12 of 49 Listing Image for 129 Molehulehu Loop 13 of 49 Listing Image for 129 Molehulehu Loop 14 of 49 Listing Image for 129 Molehulehu Loop 15 of 49 Listing Image for 129 Molehulehu Loop 16 of 49 Listing Image for 129 Molehulehu Loop 17 of 49 Listing Image for 129 Molehulehu Loop 18 of 49 Listing Image for 129 Molehulehu Loop 19 of 49 Listing Image for 129 Molehulehu Loop 20 of 49 Listing Image for 129 Molehulehu Loop 21 of 49 Listing Image for 129 Molehulehu Loop 22 of 49 Listing Image for 129 Molehulehu Loop 23 of 49 Listing Image for 129 Molehulehu Loop 24 of 49 Listing Image for 129 Molehulehu Loop 25 of 49 Listing Image for 129 Molehulehu Loop 26 of 49 Listing Image for 129 Molehulehu Loop 27 of 49 Listing Image for 129 Molehulehu Loop 28 of 49 Listing Image for 129 Molehulehu Loop 29 of 49 Listing Image for 129 Molehulehu Loop 30 of 49 Listing Image for 129 Molehulehu Loop 31 of 49 Listing Image for 129 Molehulehu Loop 32 of 49 Listing Image for 129 Molehulehu Loop 33 of 49 Listing Image for 129 Molehulehu Loop 34 of 49 Listing Image for 129 Molehulehu Loop 35 of 49 Listing Image for 129 Molehulehu Loop 36 of 49 Listing Image for 129 Molehulehu Loop 37 of 49 Listing Image for 129 Molehulehu Loop 38 of 49 Listing Image for 129 Molehulehu Loop 39 of 49 Listing Image for 129 Molehulehu Loop 40 of 49 Listing Image for 129 Molehulehu Loop 41 of 49 Listing Image for 129 Molehulehu Loop 42 of 49 Listing Image for 129 Molehulehu Loop 43 of 49 Listing Image for 129 Molehulehu Loop 44 of 49 Listing Image for 129 Molehulehu Loop 45 of 49 Listing Image for 129 Molehulehu Loop 46 of 49 Listing Image for 129 Molehulehu Loop 47 of 49 Listing Image for 129 Molehulehu Loop 48 of 49 Listing Image for 129 Molehulehu Loop 49 of 49

$1,260,000

The Legends at Maui Lani

129 Molehulehu Loop, Kahului

3 Beds 2.5 Baths 1,873 SqFt Residential MLS® # 406828 Date Sold: September 26, 2025
Sold
Closed: 05/28/2026
Listing Image for 155 Uwala Rd 1 of 46 Listing Image for 155 Uwala Rd 2 of 46 Listing Image for 155 Uwala Rd 3 of 46 Listing Image for 155 Uwala Rd 4 of 46 Listing Image for 155 Uwala Rd 5 of 46 Listing Image for 155 Uwala Rd 6 of 46 Listing Image for 155 Uwala Rd 7 of 46 Listing Image for 155 Uwala Rd 8 of 46 Listing Image for 155 Uwala Rd 9 of 46 Listing Image for 155 Uwala Rd 10 of 46 Listing Image for 155 Uwala Rd 11 of 46 Listing Image for 155 Uwala Rd 12 of 46 Listing Image for 155 Uwala Rd 13 of 46 Listing Image for 155 Uwala Rd 14 of 46 Listing Image for 155 Uwala Rd 15 of 46 Listing Image for 155 Uwala Rd 16 of 46 Listing Image for 155 Uwala Rd 17 of 46 Listing Image for 155 Uwala Rd 18 of 46 Listing Image for 155 Uwala Rd 19 of 46 Listing Image for 155 Uwala Rd 20 of 46 Listing Image for 155 Uwala Rd 21 of 46 Listing Image for 155 Uwala Rd 22 of 46 Listing Image for 155 Uwala Rd 23 of 46 Listing Image for 155 Uwala Rd 24 of 46 Listing Image for 155 Uwala Rd 25 of 46 Listing Image for 155 Uwala Rd 26 of 46 Listing Image for 155 Uwala Rd 27 of 46 Listing Image for 155 Uwala Rd 28 of 46 Listing Image for 155 Uwala Rd 29 of 46 Listing Image for 155 Uwala Rd 30 of 46 Listing Image for 155 Uwala Rd 31 of 46 Listing Image for 155 Uwala Rd 32 of 46 Listing Image for 155 Uwala Rd 33 of 46 Listing Image for 155 Uwala Rd 34 of 46 Listing Image for 155 Uwala Rd 35 of 46 Listing Image for 155 Uwala Rd 36 of 46 Listing Image for 155 Uwala Rd 37 of 46 Listing Image for 155 Uwala Rd 38 of 46 Listing Image for 155 Uwala Rd 39 of 46 Listing Image for 155 Uwala Rd 40 of 46 Listing Image for 155 Uwala Rd 41 of 46 Listing Image for 155 Uwala Rd 42 of 46 Listing Image for 155 Uwala Rd 43 of 46 Listing Image for 155 Uwala Rd 44 of 46 Listing Image for 155 Uwala Rd 45 of 46 Listing Image for 155 Uwala Rd 46 of 46

$990,000

↓ $210,000

Kaeleku

155 Uwala Rd, Hana

2 Beds 2 Baths 1,966 SqFt Residential MLS® # 406838 Date Sold: May 28, 2026
Sold
Closed: 11/17/2025
Listing Image for 54 Kupaloke St 1 of 33 Listing Image for 54 Kupaloke St 2 of 33 Listing Image for 54 Kupaloke St 3 of 33 Listing Image for 54 Kupaloke St 4 of 33 Listing Image for 54 Kupaloke St 5 of 33 Listing Image for 54 Kupaloke St 6 of 33 Listing Image for 54 Kupaloke St 7 of 33 Listing Image for 54 Kupaloke St 8 of 33 Listing Image for 54 Kupaloke St 9 of 33 Listing Image for 54 Kupaloke St 10 of 33 Listing Image for 54 Kupaloke St 11 of 33 Listing Image for 54 Kupaloke St 12 of 33 Listing Image for 54 Kupaloke St 13 of 33 Listing Image for 54 Kupaloke St 14 of 33 Listing Image for 54 Kupaloke St 15 of 33 Listing Image for 54 Kupaloke St 16 of 33 Listing Image for 54 Kupaloke St 17 of 33 Listing Image for 54 Kupaloke St 18 of 33 Listing Image for 54 Kupaloke St 19 of 33 Listing Image for 54 Kupaloke St 20 of 33 Listing Image for 54 Kupaloke St 21 of 33 Listing Image for 54 Kupaloke St 22 of 33 Listing Image for 54 Kupaloke St 23 of 33 Listing Image for 54 Kupaloke St 24 of 33 Listing Image for 54 Kupaloke St 25 of 33 Listing Image for 54 Kupaloke St 26 of 33 Listing Image for 54 Kupaloke St 27 of 33 Listing Image for 54 Kupaloke St 28 of 33 Listing Image for 54 Kupaloke St 29 of 33 Listing Image for 54 Kupaloke St 30 of 33 Listing Image for 54 Kupaloke St 31 of 33 Listing Image for 54 Kupaloke St 32 of 33 Listing Image for 54 Kupaloke St 33 of 33

$1,255,000

↓ $70,000

Anuhea

54 Kupaloke St, Wailuku

3 Beds 2.5 Baths 1,998 SqFt Residential MLS® # 406848 Date Sold: November 17, 2025
Sold
Closed: 12/09/2025
Listing Image for Lot F Hana Hwy 3-f 1 of 18 Listing Image for Lot F Hana Hwy 3-f 2 of 18 Listing Image for Lot F Hana Hwy 3-f 3 of 18 Listing Image for Lot F Hana Hwy 3-f 4 of 18 Listing Image for Lot F Hana Hwy 3-f 5 of 18 Listing Image for Lot F Hana Hwy 3-f 6 of 18 Listing Image for Lot F Hana Hwy 3-f 7 of 18 Listing Image for Lot F Hana Hwy 3-f 8 of 18 Listing Image for Lot F Hana Hwy 3-f 9 of 18 Listing Image for Lot F Hana Hwy 3-f 10 of 18 Listing Image for Lot F Hana Hwy 3-f 11 of 18 Listing Image for Lot F Hana Hwy 3-f 12 of 18 Listing Image for Lot F Hana Hwy 3-f 13 of 18 Listing Image for Lot F Hana Hwy 3-f 14 of 18 Listing Image for Lot F Hana Hwy 3-f 15 of 18 Listing Image for Lot F Hana Hwy 3-f 16 of 18 Listing Image for Lot F Hana Hwy 3-f 17 of 18 Listing Image for Lot F Hana Hwy 3-f 18 of 18

$750,000

↓ $100,000

Hana

Lot F Hana Hwy 3-f, Hana

0 Beds 0 Baths 0 SqFt Land MLS® # 404774 Date Sold: December 9, 2025
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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