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 110 Kaanapali Shores Pl 211 1 of 46 Listing Image for 110 Kaanapali Shores Pl 211 2 of 46 Listing Image for 110 Kaanapali Shores Pl 211 3 of 46 Listing Image for 110 Kaanapali Shores Pl 211 4 of 46 Listing Image for 110 Kaanapali Shores Pl 211 5 of 46 Listing Image for 110 Kaanapali Shores Pl 211 6 of 46 Listing Image for 110 Kaanapali Shores Pl 211 7 of 46 Listing Image for 110 Kaanapali Shores Pl 211 8 of 46 Listing Image for 110 Kaanapali Shores Pl 211 9 of 46 Listing Image for 110 Kaanapali Shores Pl 211 10 of 46 Listing Image for 110 Kaanapali Shores Pl 211 11 of 46 Listing Image for 110 Kaanapali Shores Pl 211 12 of 46 Listing Image for 110 Kaanapali Shores Pl 211 13 of 46 Listing Image for 110 Kaanapali Shores Pl 211 14 of 46 Listing Image for 110 Kaanapali Shores Pl 211 15 of 46 Listing Image for 110 Kaanapali Shores Pl 211 16 of 46 Listing Image for 110 Kaanapali Shores Pl 211 17 of 46 Listing Image for 110 Kaanapali Shores Pl 211 18 of 46 Listing Image for 110 Kaanapali Shores Pl 211 19 of 46 Listing Image for 110 Kaanapali Shores Pl 211 20 of 46 Listing Image for 110 Kaanapali Shores Pl 211 21 of 46 Listing Image for 110 Kaanapali Shores Pl 211 22 of 46 Listing Image for 110 Kaanapali Shores Pl 211 23 of 46 Listing Image for 110 Kaanapali Shores Pl 211 24 of 46 Listing Image for 110 Kaanapali Shores Pl 211 25 of 46 Listing Image for 110 Kaanapali Shores Pl 211 26 of 46 Listing Image for 110 Kaanapali Shores Pl 211 27 of 46 Listing Image for 110 Kaanapali Shores Pl 211 28 of 46 Listing Image for 110 Kaanapali Shores Pl 211 29 of 46 Listing Image for 110 Kaanapali Shores Pl 211 30 of 46 Listing Image for 110 Kaanapali Shores Pl 211 31 of 46 Listing Image for 110 Kaanapali Shores Pl 211 32 of 46 Listing Image for 110 Kaanapali Shores Pl 211 33 of 46 Listing Image for 110 Kaanapali Shores Pl 211 34 of 46 Listing Image for 110 Kaanapali Shores Pl 211 35 of 46 Listing Image for 110 Kaanapali Shores Pl 211 36 of 46 Listing Image for 110 Kaanapali Shores Pl 211 37 of 46 Listing Image for 110 Kaanapali Shores Pl 211 38 of 46 Listing Image for 110 Kaanapali Shores Pl 211 39 of 46 Listing Image for 110 Kaanapali Shores Pl 211 40 of 46 Listing Image for 110 Kaanapali Shores Pl 211 41 of 46 Listing Image for 110 Kaanapali Shores Pl 211 42 of 46 Listing Image for 110 Kaanapali Shores Pl 211 43 of 46 Listing Image for 110 Kaanapali Shores Pl 211 44 of 46 Listing Image for 110 Kaanapali Shores Pl 211 45 of 46 Listing Image for 110 Kaanapali Shores Pl 211 46 of 46

$2,098,000

↑ $1,000,000

Mahana 211

110 Kaanapali Shores Pl 211, Kaanapali

2 Beds 2 Baths 1,178 SqFt Residential MLS® # 408451

Days on Market: 242

Coldwell Banker Island Prop-KP Cell: 808-276-6061

Short Term Rental
Listing Image for 130 Kai Malina Pkwy Nr236 1 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 2 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 3 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 4 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 5 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 6 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 7 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 8 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 9 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 10 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 11 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 12 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 13 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 14 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 15 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 16 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 17 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 18 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 19 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 20 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 21 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 22 of 23 Listing Image for 130 Kai Malina Pkwy Nr236 23 of 23

$990,000

↓ $10,000

Honua Kai - Konea NR236

130 Kai Malina Pkwy Nr236, Kaanapali

1 Bed 1 Bath 690 SqFt Residential MLS® # 408449

Days on Market: 242

Susan Jackson Real Estate Cell: 865-206-1234

Short Term Rental
Listing Image for 272 Pualei Dr 272-3 1 of 45 Listing Image for 272 Pualei Dr 272-3 2 of 45 Listing Image for 272 Pualei Dr 272-3 3 of 45 Listing Image for 272 Pualei Dr 272-3 4 of 45 Listing Image for 272 Pualei Dr 272-3 5 of 45 Listing Image for 272 Pualei Dr 272-3 6 of 45 Listing Image for 272 Pualei Dr 272-3 7 of 45 Listing Image for 272 Pualei Dr 272-3 8 of 45 Listing Image for 272 Pualei Dr 272-3 9 of 45 Listing Image for 272 Pualei Dr 272-3 10 of 45 Listing Image for 272 Pualei Dr 272-3 11 of 45 Listing Image for 272 Pualei Dr 272-3 12 of 45 Listing Image for 272 Pualei Dr 272-3 13 of 45 Listing Image for 272 Pualei Dr 272-3 14 of 45 Listing Image for 272 Pualei Dr 272-3 15 of 45 Listing Image for 272 Pualei Dr 272-3 16 of 45 Listing Image for 272 Pualei Dr 272-3 17 of 45 Listing Image for 272 Pualei Dr 272-3 18 of 45 Listing Image for 272 Pualei Dr 272-3 19 of 45 Listing Image for 272 Pualei Dr 272-3 20 of 45 Listing Image for 272 Pualei Dr 272-3 21 of 45 Listing Image for 272 Pualei Dr 272-3 22 of 45 Listing Image for 272 Pualei Dr 272-3 23 of 45 Listing Image for 272 Pualei Dr 272-3 24 of 45 Listing Image for 272 Pualei Dr 272-3 25 of 45 Listing Image for 272 Pualei Dr 272-3 26 of 45 Listing Image for 272 Pualei Dr 272-3 27 of 45 Listing Image for 272 Pualei Dr 272-3 28 of 45 Listing Image for 272 Pualei Dr 272-3 29 of 45 Listing Image for 272 Pualei Dr 272-3 30 of 45 Listing Image for 272 Pualei Dr 272-3 31 of 45 Listing Image for 272 Pualei Dr 272-3 32 of 45 Listing Image for 272 Pualei Dr 272-3 33 of 45 Listing Image for 272 Pualei Dr 272-3 34 of 45 Listing Image for 272 Pualei Dr 272-3 35 of 45 Listing Image for 272 Pualei Dr 272-3 36 of 45 Listing Image for 272 Pualei Dr 272-3 37 of 45 Listing Image for 272 Pualei Dr 272-3 38 of 45 Listing Image for 272 Pualei Dr 272-3 39 of 45 Listing Image for 272 Pualei Dr 272-3 40 of 45 Listing Image for 272 Pualei Dr 272-3 41 of 45 Listing Image for 272 Pualei Dr 272-3 42 of 45 Listing Image for 272 Pualei Dr 272-3 43 of 45 Listing Image for 272 Pualei Dr 272-3 44 of 45 Listing Image for 272 Pualei Dr 272-3 45 of 45

$2,295,000

↓ $100,000

Puamana 272-3

272 Pualei Dr 272-3, Lahaina

3 Beds 2.5 Baths 1,560 SqFt Residential MLS® # 408444

Days on Market: 243

Mark A Marchello Inc

Short Term Rental
Listing Image for 500 Kapalua Dr 19t6-7 1 of 46 Listing Image for 500 Kapalua Dr 19t6-7 2 of 46 Listing Image for 500 Kapalua Dr 19t6-7 3 of 46 Listing Image for 500 Kapalua Dr 19t6-7 4 of 46 Listing Image for 500 Kapalua Dr 19t6-7 5 of 46 Listing Image for 500 Kapalua Dr 19t6-7 6 of 46 Listing Image for 500 Kapalua Dr 19t6-7 7 of 46 Listing Image for 500 Kapalua Dr 19t6-7 8 of 46 Listing Image for 500 Kapalua Dr 19t6-7 9 of 46 Listing Image for 500 Kapalua Dr 19t6-7 10 of 46 Listing Image for 500 Kapalua Dr 19t6-7 11 of 46 Listing Image for 500 Kapalua Dr 19t6-7 12 of 46 Listing Image for 500 Kapalua Dr 19t6-7 13 of 46 Listing Image for 500 Kapalua Dr 19t6-7 14 of 46 Listing Image for 500 Kapalua Dr 19t6-7 15 of 46 Listing Image for 500 Kapalua Dr 19t6-7 16 of 46 Listing Image for 500 Kapalua Dr 19t6-7 17 of 46 Listing Image for 500 Kapalua Dr 19t6-7 18 of 46 Listing Image for 500 Kapalua Dr 19t6-7 19 of 46 Listing Image for 500 Kapalua Dr 19t6-7 20 of 46 Listing Image for 500 Kapalua Dr 19t6-7 21 of 46 Listing Image for 500 Kapalua Dr 19t6-7 22 of 46 Listing Image for 500 Kapalua Dr 19t6-7 23 of 46 Listing Image for 500 Kapalua Dr 19t6-7 24 of 46 Listing Image for 500 Kapalua Dr 19t6-7 25 of 46 Listing Image for 500 Kapalua Dr 19t6-7 26 of 46 Listing Image for 500 Kapalua Dr 19t6-7 27 of 46 Listing Image for 500 Kapalua Dr 19t6-7 28 of 46 Listing Image for 500 Kapalua Dr 19t6-7 29 of 46 Listing Image for 500 Kapalua Dr 19t6-7 30 of 46 Listing Image for 500 Kapalua Dr 19t6-7 31 of 46 Listing Image for 500 Kapalua Dr 19t6-7 32 of 46 Listing Image for 500 Kapalua Dr 19t6-7 33 of 46 Listing Image for 500 Kapalua Dr 19t6-7 34 of 46 Listing Image for 500 Kapalua Dr 19t6-7 35 of 46 Listing Image for 500 Kapalua Dr 19t6-7 36 of 46 Listing Image for 500 Kapalua Dr 19t6-7 37 of 46 Listing Image for 500 Kapalua Dr 19t6-7 38 of 46 Listing Image for 500 Kapalua Dr 19t6-7 39 of 46 Listing Image for 500 Kapalua Dr 19t6-7 40 of 46 Listing Image for 500 Kapalua Dr 19t6-7 41 of 46 Listing Image for 500 Kapalua Dr 19t6-7 42 of 46 Listing Image for 500 Kapalua Dr 19t6-7 43 of 46 Listing Image for 500 Kapalua Dr 19t6-7 44 of 46 Listing Image for 500 Kapalua Dr 19t6-7 45 of 46 Listing Image for 500 Kapalua Dr 19t6-7 46 of 46

$1,525,000

↓ $150,000

Kapalua Golf Villas 19T6-7

500 Kapalua Dr 19t6-7, Kapalua

2 Beds 2 Baths 1,344 SqFt Residential MLS® # 408441

Days on Market: 243

Island Sotheby's International Realty(L) Cell: 808-283-4922

Buying Real Estate on Maui

Buying Real Estate on Maui

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

Read the Guide
Listing Image for 2475 Kaupakalua Rd 1 of 28 Listing Image for 2475 Kaupakalua Rd 2 of 28 Listing Image for 2475 Kaupakalua Rd 3 of 28 Listing Image for 2475 Kaupakalua Rd 4 of 28 Listing Image for 2475 Kaupakalua Rd 5 of 28 Listing Image for 2475 Kaupakalua Rd 6 of 28 Listing Image for 2475 Kaupakalua Rd 7 of 28 Listing Image for 2475 Kaupakalua Rd 8 of 28 Listing Image for 2475 Kaupakalua Rd 9 of 28 Listing Image for 2475 Kaupakalua Rd 10 of 28 Listing Image for 2475 Kaupakalua Rd 11 of 28 Listing Image for 2475 Kaupakalua Rd 12 of 28 Listing Image for 2475 Kaupakalua Rd 13 of 28 Listing Image for 2475 Kaupakalua Rd 14 of 28 Listing Image for 2475 Kaupakalua Rd 15 of 28 Listing Image for 2475 Kaupakalua Rd 16 of 28 Listing Image for 2475 Kaupakalua Rd 17 of 28 Listing Image for 2475 Kaupakalua Rd 18 of 28 Listing Image for 2475 Kaupakalua Rd 19 of 28 Listing Image for 2475 Kaupakalua Rd 20 of 28 Listing Image for 2475 Kaupakalua Rd 21 of 28 Listing Image for 2475 Kaupakalua Rd 22 of 28 Listing Image for 2475 Kaupakalua Rd 23 of 28 Listing Image for 2475 Kaupakalua Rd 24 of 28 Listing Image for 2475 Kaupakalua Rd 25 of 28 Listing Image for 2475 Kaupakalua Rd 26 of 28 Listing Image for 2475 Kaupakalua Rd 27 of 28 Listing Image for 2475 Kaupakalua Rd 28 of 28

$1,375,000

↓ $321,000

Haiku

2475 Kaupakalua Rd, Haiku

3 Beds 2 Baths 1,608 SqFt Residential MLS® # 408424

Days on Market: 244

Island Sotheby's Int'l Rlty(W) Cell: 808-385-6564

Listing Image for 103 Ka Ikena Loop 1 of 20 Listing Image for 103 Ka Ikena Loop 2 of 20 Listing Image for 103 Ka Ikena Loop 3 of 20 Listing Image for 103 Ka Ikena Loop 4 of 20 Listing Image for 103 Ka Ikena Loop 5 of 20 Listing Image for 103 Ka Ikena Loop 6 of 20 Listing Image for 103 Ka Ikena Loop 7 of 20 Listing Image for 103 Ka Ikena Loop 8 of 20 Listing Image for 103 Ka Ikena Loop 9 of 20 Listing Image for 103 Ka Ikena Loop 10 of 20 Listing Image for 103 Ka Ikena Loop 11 of 20 Listing Image for 103 Ka Ikena Loop 12 of 20 Listing Image for 103 Ka Ikena Loop 13 of 20 Listing Image for 103 Ka Ikena Loop 14 of 20 Listing Image for 103 Ka Ikena Loop 15 of 20 Listing Image for 103 Ka Ikena Loop 16 of 20 Listing Image for 103 Ka Ikena Loop 17 of 20 Listing Image for 103 Ka Ikena Loop 18 of 20 Listing Image for 103 Ka Ikena Loop 19 of 20 Listing Image for 103 Ka Ikena Loop 20 of 20

$1,479,000

↓ $21,000

Ke'alohilani at Kehalani

103 Ka Ikena Loop, Wailuku

4 Beds 3.5 Baths 1,907 SqFt Residential MLS® # 408421

Days on Market: 244

Keller Williams Realty Maui-Ka Cell: 808-870-0674

Short Term Rental
Listing Image for 500 Kapalua Dr 20p 5-6 1 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 2 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 3 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 4 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 5 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 6 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 7 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 8 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 9 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 10 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 11 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 12 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 13 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 14 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 15 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 16 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 17 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 18 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 19 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 20 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 21 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 22 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 23 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 24 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 25 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 26 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 27 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 28 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 29 of 30 Listing Image for 500 Kapalua Dr 20p 5-6 30 of 30

$1,285,000

↓ $56,000

Kapalua Golf Villas 20P 5-6

500 Kapalua Dr 20p 5-6, Kapalua

2 Beds 2 Baths 1,344 SqFt Residential MLS® # 408414

Days on Market: 245

Coldwell Banker Island Prop-KP Cell: 808-457-0604

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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: 02/06/2026
Listing Image for 61 Kainehe Pl 61 1 of 50 Listing Image for 61 Kainehe Pl 61 2 of 50 Listing Image for 61 Kainehe Pl 61 3 of 50 Listing Image for 61 Kainehe Pl 61 4 of 50 Listing Image for 61 Kainehe Pl 61 5 of 50 Listing Image for 61 Kainehe Pl 61 6 of 50 Listing Image for 61 Kainehe Pl 61 7 of 50 Listing Image for 61 Kainehe Pl 61 8 of 50 Listing Image for 61 Kainehe Pl 61 9 of 50 Listing Image for 61 Kainehe Pl 61 10 of 50 Listing Image for 61 Kainehe Pl 61 11 of 50 Listing Image for 61 Kainehe Pl 61 12 of 50 Listing Image for 61 Kainehe Pl 61 13 of 50 Listing Image for 61 Kainehe Pl 61 14 of 50 Listing Image for 61 Kainehe Pl 61 15 of 50 Listing Image for 61 Kainehe Pl 61 16 of 50 Listing Image for 61 Kainehe Pl 61 17 of 50 Listing Image for 61 Kainehe Pl 61 18 of 50 Listing Image for 61 Kainehe Pl 61 19 of 50 Listing Image for 61 Kainehe Pl 61 20 of 50 Listing Image for 61 Kainehe Pl 61 21 of 50 Listing Image for 61 Kainehe Pl 61 22 of 50 Listing Image for 61 Kainehe Pl 61 23 of 50 Listing Image for 61 Kainehe Pl 61 24 of 50 Listing Image for 61 Kainehe Pl 61 25 of 50 Listing Image for 61 Kainehe Pl 61 26 of 50 Listing Image for 61 Kainehe Pl 61 27 of 50 Listing Image for 61 Kainehe Pl 61 28 of 50 Listing Image for 61 Kainehe Pl 61 29 of 50 Listing Image for 61 Kainehe Pl 61 30 of 50 Listing Image for 61 Kainehe Pl 61 31 of 50 Listing Image for 61 Kainehe Pl 61 32 of 50 Listing Image for 61 Kainehe Pl 61 33 of 50 Listing Image for 61 Kainehe Pl 61 34 of 50 Listing Image for 61 Kainehe Pl 61 35 of 50 Listing Image for 61 Kainehe Pl 61 36 of 50 Listing Image for 61 Kainehe Pl 61 37 of 50 Listing Image for 61 Kainehe Pl 61 38 of 50 Listing Image for 61 Kainehe Pl 61 39 of 50 Listing Image for 61 Kainehe Pl 61 40 of 50 Listing Image for 61 Kainehe Pl 61 41 of 50 Listing Image for 61 Kainehe Pl 61 42 of 50 Listing Image for 61 Kainehe Pl 61 43 of 50 Listing Image for 61 Kainehe Pl 61 44 of 50 Listing Image for 61 Kainehe Pl 61 45 of 50 Listing Image for 61 Kainehe Pl 61 46 of 50 Listing Image for 61 Kainehe Pl 61 47 of 50 Listing Image for 61 Kainehe Pl 61 48 of 50 Listing Image for 61 Kainehe Pl 61 49 of 50 Listing Image for 61 Kainehe Pl 61 50 of 50

$2,685,000

↓ $164,500

Kai Malu 61

61 Kainehe Pl 61, Wailea/Makena

3 Beds 2.5 Baths 1,796 SqFt Residential MLS® # 407486 Date Sold: February 6, 2026
Sold
Closed: 04/17/2026
Listing Image for 3543 Lower Honoapiilani Rd J302 1 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 2 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 3 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 4 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 5 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 6 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 7 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 8 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 9 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 10 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 11 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 12 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 13 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 14 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 15 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 16 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 17 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 18 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 19 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 20 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 21 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 22 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 23 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 24 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 25 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 26 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 27 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 28 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 29 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 30 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 31 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 32 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 33 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 34 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 35 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 36 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 37 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 38 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 39 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 40 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 41 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 42 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 43 of 44 Listing Image for 3543 Lower Honoapiilani Rd J302 44 of 44

$950,000

Papakea Resort J302

3543 Lower Honoapiilani Rd J302, Napili/Kahana/Honokowai

2 Beds 2 Baths 861 SqFt Residential MLS® # 407484 Date Sold: April 17, 2026
Sold
Closed: 12/11/2025
Listing Image for 1991 Kahekili Hwy 1 of 23 Listing Image for 1991 Kahekili Hwy 2 of 23 Listing Image for 1991 Kahekili Hwy 3 of 23 Listing Image for 1991 Kahekili Hwy 4 of 23 Listing Image for 1991 Kahekili Hwy 5 of 23 Listing Image for 1991 Kahekili Hwy 6 of 23 Listing Image for 1991 Kahekili Hwy 7 of 23 Listing Image for 1991 Kahekili Hwy 8 of 23 Listing Image for 1991 Kahekili Hwy 9 of 23 Listing Image for 1991 Kahekili Hwy 10 of 23 Listing Image for 1991 Kahekili Hwy 11 of 23 Listing Image for 1991 Kahekili Hwy 12 of 23 Listing Image for 1991 Kahekili Hwy 13 of 23 Listing Image for 1991 Kahekili Hwy 14 of 23 Listing Image for 1991 Kahekili Hwy 15 of 23 Listing Image for 1991 Kahekili Hwy 16 of 23 Listing Image for 1991 Kahekili Hwy 17 of 23 Listing Image for 1991 Kahekili Hwy 18 of 23 Listing Image for 1991 Kahekili Hwy 19 of 23 Listing Image for 1991 Kahekili Hwy 20 of 23 Listing Image for 1991 Kahekili Hwy 21 of 23 Listing Image for 1991 Kahekili Hwy 22 of 23 Listing Image for 1991 Kahekili Hwy 23 of 23

$825,000

Waihee Village

1991 Kahekili Hwy, Wailuku

3 Beds 1.5 Baths 960 SqFt Residential MLS® # 407478 Date Sold: December 11, 2025
Sold
Closed: 01/07/2026
206 Heleuma Pl, Wailea/Makena

$3,300,000

Wailea Kialoa

206 Heleuma Pl, Wailea/Makena

3 Beds 2.5 Baths 3,169 SqFt Residential MLS® # 407476 Date Sold: January 7, 2026
Sold
Closed: 06/17/2026
Listing Image for 130 Kai Malina Pkwy Sr-746 1 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 2 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 3 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 4 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 5 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 6 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 7 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 8 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 9 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 10 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 11 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 12 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 13 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 14 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 15 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 16 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 17 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 18 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 19 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 20 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 21 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 22 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 23 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 24 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 25 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 26 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 27 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 28 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 29 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 30 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 31 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 32 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 33 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 34 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 35 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 36 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 37 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 38 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 39 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 40 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 41 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 42 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 43 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 44 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 45 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 46 of 47 Listing Image for 130 Kai Malina Pkwy Sr-746 47 of 47

$2,100,000

↓ $299,000

Honua Kai - Hoku Lani SR-746

130 Kai Malina Pkwy Sr-746, Kaanapali

2 Beds 2 Baths 1,100 SqFt Residential MLS® # 407468 Date Sold: June 17, 2026
Sold
Closed: 03/23/2026
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$1,900,000

↓ $395,000

Wailea Palms 2902

3150 Wailea Alanui Dr 2902, Wailea/Makena

2 Beds 2.5 Baths 1,559 SqFt Residential MLS® # 407465 Date Sold: March 23, 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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