Strategies of Buying and Selling Simultaneously

Buying and Selling a Home at the Same Time

You may have found yourself in a position where you would like to buy one property while simultaneously selling another property. While doing this does present some unique challenges, it's completely possible to pull this off with the proper strategy and some degree of flexibility

The reasons and strategies for wanting to buy and sell simultaneously will differ from a primary homeowner looking to relocate to an investor seeking to execute a 1031 exchange to avoid capital gains taxes. In either instance, it's important to have a sound strategy and understand what the undertaking will involve. 

Selling A Primary Residence While Buying Another

There are several different ways to do this and how you do it will depend on your financial philosophies. There isn't necessarily a right and wrong way to approach this, some consider selling their home first the priority and then are willing to rent for a period of 6 months while they find the perfect replacement. This is usually the lowest stress avenue.

Some will be intent on executing the sale and purchase in such a way that both properties close in close succession to remove the extra step of renting. Money is a huge consideration for this move, particularly when financing is involved. In many instances, sellers will need the equity from the sale of their home to fund the down payment on the purchase of the second. 

If Financing is Necessary, Get Prequalified for a New Mortgage First

Before you get serious about selling your home, you should thoroughly research the possibility of buying a new primary residence. The Maui housing market can change rapidly at times, and the lending environment is changing as well. When you get prequalified with a local Maui lender, you can better determine your price range for a new home.

You can get accurate information about the interest rates available for your credit score and other qualifications. In addition, you can confirm that you can afford the loan payment for the size and quality of the home you are interested in.

Discuss Your Plans with a Real Estate Agent

After learning about your prequalification status, consulting with real estate agents in Maui is the next step. An experienced Maui real estate agent can help you determine how long your home may reasonably remain on the market.

In addition, you can get details on a realistic sales price. By analyzing the sales price in combination with closing costs and the current mortgage payoff balance, you can determine the sales proceeds that you have available for a down payment on your new home purchase. 

Newest Maui Properties For Sale

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Listing Image for 4685 Uakea Rd 1 of 50 Listing Image for 4685 Uakea Rd 2 of 50 Listing Image for 4685 Uakea Rd 3 of 50 Listing Image for 4685 Uakea Rd 4 of 50 Listing Image for 4685 Uakea Rd 5 of 50 Listing Image for 4685 Uakea Rd 6 of 50 Listing Image for 4685 Uakea Rd 7 of 50 Listing Image for 4685 Uakea Rd 8 of 50 Listing Image for 4685 Uakea Rd 9 of 50 Listing Image for 4685 Uakea Rd 10 of 50 Listing Image for 4685 Uakea Rd 11 of 50 Listing Image for 4685 Uakea Rd 12 of 50 Listing Image for 4685 Uakea Rd 13 of 50 Listing Image for 4685 Uakea Rd 14 of 50 Listing Image for 4685 Uakea Rd 15 of 50 Listing Image for 4685 Uakea Rd 16 of 50 Listing Image for 4685 Uakea Rd 17 of 50 Listing Image for 4685 Uakea Rd 18 of 50 Listing Image for 4685 Uakea Rd 19 of 50 Listing Image for 4685 Uakea Rd 20 of 50 Listing Image for 4685 Uakea Rd 21 of 50 Listing Image for 4685 Uakea Rd 22 of 50 Listing Image for 4685 Uakea Rd 23 of 50 Listing Image for 4685 Uakea Rd 24 of 50 Listing Image for 4685 Uakea Rd 25 of 50 Listing Image for 4685 Uakea Rd 26 of 50 Listing Image for 4685 Uakea Rd 27 of 50 Listing Image for 4685 Uakea Rd 28 of 50 Listing Image for 4685 Uakea Rd 29 of 50 Listing Image for 4685 Uakea Rd 30 of 50 Listing Image for 4685 Uakea Rd 31 of 50 Listing Image for 4685 Uakea Rd 32 of 50 Listing Image for 4685 Uakea Rd 33 of 50 Listing Image for 4685 Uakea Rd 34 of 50 Listing Image for 4685 Uakea Rd 35 of 50 Listing Image for 4685 Uakea Rd 36 of 50 Listing Image for 4685 Uakea Rd 37 of 50 Listing Image for 4685 Uakea Rd 38 of 50 Listing Image for 4685 Uakea Rd 39 of 50 Listing Image for 4685 Uakea Rd 40 of 50 Listing Image for 4685 Uakea Rd 41 of 50 Listing Image for 4685 Uakea Rd 42 of 50 Listing Image for 4685 Uakea Rd 43 of 50 Listing Image for 4685 Uakea Rd 44 of 50 Listing Image for 4685 Uakea Rd 45 of 50 Listing Image for 4685 Uakea Rd 46 of 50 Listing Image for 4685 Uakea Rd 47 of 50 Listing Image for 4685 Uakea Rd 48 of 50 Listing Image for 4685 Uakea Rd 49 of 50 Listing Image for 4685 Uakea Rd 50 of 50

$1,100,000

↓ $245,000

Hana

4685 Uakea Rd, Hana

3 Beds 3 Baths 1,164 SqFt Residential MLS® # 408305

Days on Market: 255

REMAX Hawaii Maui

Listing Image for 614 Kupulau Pl 1 of 48 Listing Image for 614 Kupulau Pl 2 of 48 Listing Image for 614 Kupulau Pl 3 of 48 Listing Image for 614 Kupulau Pl 4 of 48 Listing Image for 614 Kupulau Pl 5 of 48 Listing Image for 614 Kupulau Pl 6 of 48 Listing Image for 614 Kupulau Pl 7 of 48 Listing Image for 614 Kupulau Pl 8 of 48 Listing Image for 614 Kupulau Pl 9 of 48 Listing Image for 614 Kupulau Pl 10 of 48 Listing Image for 614 Kupulau Pl 11 of 48 Listing Image for 614 Kupulau Pl 12 of 48 Listing Image for 614 Kupulau Pl 13 of 48 Listing Image for 614 Kupulau Pl 14 of 48 Listing Image for 614 Kupulau Pl 15 of 48 Listing Image for 614 Kupulau Pl 16 of 48 Listing Image for 614 Kupulau Pl 17 of 48 Listing Image for 614 Kupulau Pl 18 of 48 Listing Image for 614 Kupulau Pl 19 of 48 Listing Image for 614 Kupulau Pl 20 of 48 Listing Image for 614 Kupulau Pl 21 of 48 Listing Image for 614 Kupulau Pl 22 of 48 Listing Image for 614 Kupulau Pl 23 of 48 Listing Image for 614 Kupulau Pl 24 of 48 Listing Image for 614 Kupulau Pl 25 of 48 Listing Image for 614 Kupulau Pl 26 of 48 Listing Image for 614 Kupulau Pl 27 of 48 Listing Image for 614 Kupulau Pl 28 of 48 Listing Image for 614 Kupulau Pl 29 of 48 Listing Image for 614 Kupulau Pl 30 of 48 Listing Image for 614 Kupulau Pl 31 of 48 Listing Image for 614 Kupulau Pl 32 of 48 Listing Image for 614 Kupulau Pl 33 of 48 Listing Image for 614 Kupulau Pl 34 of 48 Listing Image for 614 Kupulau Pl 35 of 48 Listing Image for 614 Kupulau Pl 36 of 48 Listing Image for 614 Kupulau Pl 37 of 48 Listing Image for 614 Kupulau Pl 38 of 48 Listing Image for 614 Kupulau Pl 39 of 48 Listing Image for 614 Kupulau Pl 40 of 48 Listing Image for 614 Kupulau Pl 41 of 48 Listing Image for 614 Kupulau Pl 42 of 48 Listing Image for 614 Kupulau Pl 43 of 48 Listing Image for 614 Kupulau Pl 44 of 48 Listing Image for 614 Kupulau Pl 45 of 48 Listing Image for 614 Kupulau Pl 46 of 48 Listing Image for 614 Kupulau Pl 47 of 48 Listing Image for 614 Kupulau Pl 48 of 48

$2,180,000

↓ $10,000

Maui Meadows

614 Kupulau Pl, Maui Meadows

4 Beds 3 Baths 2,215 SqFt Residential MLS® # 408295

Days on Market: 257

Bello Realty Inc Cell: 808-357-2837

Short Term Rental
Listing Image for 3800 Wailea Alanui Dr Ph-303 1 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 2 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 3 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 4 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 5 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 6 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 7 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 8 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 9 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 10 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 11 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 12 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 13 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 14 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 15 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 16 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 17 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 18 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 19 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 20 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 21 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 22 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 23 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 24 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 25 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 26 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 27 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 28 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 29 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 30 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 31 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 32 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 33 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 34 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 35 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 36 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 37 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 38 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 39 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 40 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 41 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 42 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 43 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 44 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 45 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 46 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 47 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 48 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 49 of 50 Listing Image for 3800 Wailea Alanui Dr Ph-303 50 of 50

$5,500,000

Wailea Beach Villas PH-303

3800 Wailea Alanui Dr Ph-303, Wailea/Makena

3 Beds 3 Baths 1,961 SqFt Residential MLS® # 408288

Days on Market: 257

Compass-W

In Escrow
Listing Image for 100 Auhana Rd 301 1 of 50 Listing Image for 100 Auhana Rd 301 2 of 50 Listing Image for 100 Auhana Rd 301 3 of 50 Listing Image for 100 Auhana Rd 301 4 of 50 Listing Image for 100 Auhana Rd 301 5 of 50 Listing Image for 100 Auhana Rd 301 6 of 50 Listing Image for 100 Auhana Rd 301 7 of 50 Listing Image for 100 Auhana Rd 301 8 of 50 Listing Image for 100 Auhana Rd 301 9 of 50 Listing Image for 100 Auhana Rd 301 10 of 50 Listing Image for 100 Auhana Rd 301 11 of 50 Listing Image for 100 Auhana Rd 301 12 of 50 Listing Image for 100 Auhana Rd 301 13 of 50 Listing Image for 100 Auhana Rd 301 14 of 50 Listing Image for 100 Auhana Rd 301 15 of 50 Listing Image for 100 Auhana Rd 301 16 of 50 Listing Image for 100 Auhana Rd 301 17 of 50 Listing Image for 100 Auhana Rd 301 18 of 50 Listing Image for 100 Auhana Rd 301 19 of 50 Listing Image for 100 Auhana Rd 301 20 of 50 Listing Image for 100 Auhana Rd 301 21 of 50 Listing Image for 100 Auhana Rd 301 22 of 50 Listing Image for 100 Auhana Rd 301 23 of 50 Listing Image for 100 Auhana Rd 301 24 of 50 Listing Image for 100 Auhana Rd 301 25 of 50 Listing Image for 100 Auhana Rd 301 26 of 50 Listing Image for 100 Auhana Rd 301 27 of 50 Listing Image for 100 Auhana Rd 301 28 of 50 Listing Image for 100 Auhana Rd 301 29 of 50 Listing Image for 100 Auhana Rd 301 30 of 50 Listing Image for 100 Auhana Rd 301 31 of 50 Listing Image for 100 Auhana Rd 301 32 of 50 Listing Image for 100 Auhana Rd 301 33 of 50 Listing Image for 100 Auhana Rd 301 34 of 50 Listing Image for 100 Auhana Rd 301 35 of 50 Listing Image for 100 Auhana Rd 301 36 of 50 Listing Image for 100 Auhana Rd 301 37 of 50 Listing Image for 100 Auhana Rd 301 38 of 50 Listing Image for 100 Auhana Rd 301 39 of 50 Listing Image for 100 Auhana Rd 301 40 of 50 Listing Image for 100 Auhana Rd 301 41 of 50 Listing Image for 100 Auhana Rd 301 42 of 50 Listing Image for 100 Auhana Rd 301 43 of 50 Listing Image for 100 Auhana Rd 301 44 of 50 Listing Image for 100 Auhana Rd 301 45 of 50 Listing Image for 100 Auhana Rd 301 46 of 50 Listing Image for 100 Auhana Rd 301 47 of 50 Listing Image for 100 Auhana Rd 301 48 of 50 Listing Image for 100 Auhana Rd 301 49 of 50 Listing Image for 100 Auhana Rd 301 50 of 50

$1,025,000

Auhana Kuleana 301

100 Auhana Rd 301, Kihei

3 Beds 2.5 Baths 1,569 SqFt Residential MLS® # 405048

Days on Market: 571

Kumulani Vacations&Realty

Listing Image for 3615 Lower Honoapiilani Rd 222 1 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 2 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 3 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 4 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 5 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 6 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 7 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 8 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 9 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 10 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 11 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 12 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 13 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 14 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 15 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 16 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 17 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 18 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 19 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 20 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 21 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 22 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 23 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 24 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 25 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 26 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 27 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 28 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 29 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 30 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 31 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 32 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 33 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 34 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 35 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 36 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 37 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 38 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 39 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 40 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 41 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 42 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 43 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 44 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 45 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 46 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 47 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 48 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 49 of 50 Listing Image for 3615 Lower Honoapiilani Rd 222 50 of 50

$1,022,000

↓ $128,000

Paki Maui 222

3615 Lower Honoapiilani Rd 222, Napili/Kahana/Honokowai

2 Beds 2 Baths 1,082 SqFt Residential MLS® # 408275

Days on Market: 259

Keller Williams Realty Maui-L Cell: 808-385-2918

Listing Image for 4955 Uakea Rd 1 of 36 Listing Image for 4955 Uakea Rd 2 of 36 Listing Image for 4955 Uakea Rd 3 of 36 Listing Image for 4955 Uakea Rd 4 of 36 Listing Image for 4955 Uakea Rd 5 of 36 Listing Image for 4955 Uakea Rd 6 of 36 Listing Image for 4955 Uakea Rd 7 of 36 Listing Image for 4955 Uakea Rd 8 of 36 Listing Image for 4955 Uakea Rd 9 of 36 Listing Image for 4955 Uakea Rd 10 of 36 Listing Image for 4955 Uakea Rd 11 of 36 Listing Image for 4955 Uakea Rd 12 of 36 Listing Image for 4955 Uakea Rd 13 of 36 Listing Image for 4955 Uakea Rd 14 of 36 Listing Image for 4955 Uakea Rd 15 of 36 Listing Image for 4955 Uakea Rd 16 of 36 Listing Image for 4955 Uakea Rd 17 of 36 Listing Image for 4955 Uakea Rd 18 of 36 Listing Image for 4955 Uakea Rd 19 of 36 Listing Image for 4955 Uakea Rd 20 of 36 Listing Image for 4955 Uakea Rd 21 of 36 Listing Image for 4955 Uakea Rd 22 of 36 Listing Image for 4955 Uakea Rd 23 of 36 Listing Image for 4955 Uakea Rd 24 of 36 Listing Image for 4955 Uakea Rd 25 of 36 Listing Image for 4955 Uakea Rd 26 of 36 Listing Image for 4955 Uakea Rd 27 of 36 Listing Image for 4955 Uakea Rd 28 of 36 Listing Image for 4955 Uakea Rd 29 of 36 Listing Image for 4955 Uakea Rd 30 of 36 Listing Image for 4955 Uakea Rd 31 of 36 Listing Image for 4955 Uakea Rd 32 of 36 Listing Image for 4955 Uakea Rd 33 of 36 Listing Image for 4955 Uakea Rd 34 of 36 Listing Image for 4955 Uakea Rd 35 of 36 Listing Image for 4955 Uakea Rd 36 of 36

$2,200,000

Hana Bay

4955 Uakea Rd, Hana

2 Beds 2.5 Baths 1,476 SqFt Residential MLS® # 408273

Days on Market: 258

Keller Williams Realty Maui-Ka Cell: 808-268-0499

Listing Image for 1008 Sunset Pl 1 of 50 Listing Image for 1008 Sunset Pl 2 of 50 Listing Image for 1008 Sunset Pl 3 of 50 Listing Image for 1008 Sunset Pl 4 of 50 Listing Image for 1008 Sunset Pl 5 of 50 Listing Image for 1008 Sunset Pl 6 of 50 Listing Image for 1008 Sunset Pl 7 of 50 Listing Image for 1008 Sunset Pl 8 of 50 Listing Image for 1008 Sunset Pl 9 of 50 Listing Image for 1008 Sunset Pl 10 of 50 Listing Image for 1008 Sunset Pl 11 of 50 Listing Image for 1008 Sunset Pl 12 of 50 Listing Image for 1008 Sunset Pl 13 of 50 Listing Image for 1008 Sunset Pl 14 of 50 Listing Image for 1008 Sunset Pl 15 of 50 Listing Image for 1008 Sunset Pl 16 of 50 Listing Image for 1008 Sunset Pl 17 of 50 Listing Image for 1008 Sunset Pl 18 of 50 Listing Image for 1008 Sunset Pl 19 of 50 Listing Image for 1008 Sunset Pl 20 of 50 Listing Image for 1008 Sunset Pl 21 of 50 Listing Image for 1008 Sunset Pl 22 of 50 Listing Image for 1008 Sunset Pl 23 of 50 Listing Image for 1008 Sunset Pl 24 of 50 Listing Image for 1008 Sunset Pl 25 of 50 Listing Image for 1008 Sunset Pl 26 of 50 Listing Image for 1008 Sunset Pl 27 of 50 Listing Image for 1008 Sunset Pl 28 of 50 Listing Image for 1008 Sunset Pl 29 of 50 Listing Image for 1008 Sunset Pl 30 of 50 Listing Image for 1008 Sunset Pl 31 of 50 Listing Image for 1008 Sunset Pl 32 of 50 Listing Image for 1008 Sunset Pl 33 of 50 Listing Image for 1008 Sunset Pl 34 of 50 Listing Image for 1008 Sunset Pl 35 of 50 Listing Image for 1008 Sunset Pl 36 of 50 Listing Image for 1008 Sunset Pl 37 of 50 Listing Image for 1008 Sunset Pl 38 of 50 Listing Image for 1008 Sunset Pl 39 of 50 Listing Image for 1008 Sunset Pl 40 of 50 Listing Image for 1008 Sunset Pl 41 of 50 Listing Image for 1008 Sunset Pl 42 of 50 Listing Image for 1008 Sunset Pl 43 of 50 Listing Image for 1008 Sunset Pl 44 of 50 Listing Image for 1008 Sunset Pl 45 of 50 Listing Image for 1008 Sunset Pl 46 of 50 Listing Image for 1008 Sunset Pl 47 of 50 Listing Image for 1008 Sunset Pl 48 of 50 Listing Image for 1008 Sunset Pl 49 of 50 Listing Image for 1008 Sunset Pl 50 of 50

$5,195,000

↓ $100,000

Pineapple Hill

1008 Sunset Pl, Kapalua

3 Beds 3.5 Baths 4,574 SqFt Residential MLS® # 408268

Days on Market: 259

Island Sotheby's International Realty(L) Cell: 808-250-0210

View 7 More Listings

Apply for a Home Equity Loan

While you may ideally want to sell your current house before buying a new one, this may not be an absolute requirement for some sellers. You could tap into your home’s equity by applying for an equity line of credit. Before moving forward with this possibility, be aware that the payment on the new home equity line will affect your debt-to-income ratio.

Mortgage lenders review your debt-to-income ratio as part of their qualification process. Because of this, you should discuss this option in detail with your lender to ensure that it will not impair your ability to qualify for a new mortgage.

Recent Sales on Maui

Sold
Closed: 10/13/2025
5295 Lower Honoapiilani Rd B-25, Napili/Kahana/Honokowai

$835,000

Napili Point B-25

5295 Lower Honoapiilani Rd B-25, Napili/Kahana/Honokowai

1 Bed 1 Bath 720 SqFt Residential MLS® # 407406 Date Sold: October 13, 2025
Sold
Closed: 01/29/2026
Listing Image for 124 Waaula Pl 1 of 50 Listing Image for 124 Waaula Pl 2 of 50 Listing Image for 124 Waaula Pl 3 of 50 Listing Image for 124 Waaula Pl 4 of 50 Listing Image for 124 Waaula Pl 5 of 50 Listing Image for 124 Waaula Pl 6 of 50 Listing Image for 124 Waaula Pl 7 of 50 Listing Image for 124 Waaula Pl 8 of 50 Listing Image for 124 Waaula Pl 9 of 50 Listing Image for 124 Waaula Pl 10 of 50 Listing Image for 124 Waaula Pl 11 of 50 Listing Image for 124 Waaula Pl 12 of 50 Listing Image for 124 Waaula Pl 13 of 50 Listing Image for 124 Waaula Pl 14 of 50 Listing Image for 124 Waaula Pl 15 of 50 Listing Image for 124 Waaula Pl 16 of 50 Listing Image for 124 Waaula Pl 17 of 50 Listing Image for 124 Waaula Pl 18 of 50 Listing Image for 124 Waaula Pl 19 of 50 Listing Image for 124 Waaula Pl 20 of 50 Listing Image for 124 Waaula Pl 21 of 50 Listing Image for 124 Waaula Pl 22 of 50 Listing Image for 124 Waaula Pl 23 of 50 Listing Image for 124 Waaula Pl 24 of 50 Listing Image for 124 Waaula Pl 25 of 50 Listing Image for 124 Waaula Pl 26 of 50 Listing Image for 124 Waaula Pl 27 of 50 Listing Image for 124 Waaula Pl 28 of 50 Listing Image for 124 Waaula Pl 29 of 50 Listing Image for 124 Waaula Pl 30 of 50 Listing Image for 124 Waaula Pl 31 of 50 Listing Image for 124 Waaula Pl 32 of 50 Listing Image for 124 Waaula Pl 33 of 50 Listing Image for 124 Waaula Pl 34 of 50 Listing Image for 124 Waaula Pl 35 of 50 Listing Image for 124 Waaula Pl 36 of 50 Listing Image for 124 Waaula Pl 37 of 50 Listing Image for 124 Waaula Pl 38 of 50 Listing Image for 124 Waaula Pl 39 of 50 Listing Image for 124 Waaula Pl 40 of 50 Listing Image for 124 Waaula Pl 41 of 50 Listing Image for 124 Waaula Pl 42 of 50 Listing Image for 124 Waaula Pl 43 of 50 Listing Image for 124 Waaula Pl 44 of 50 Listing Image for 124 Waaula Pl 45 of 50 Listing Image for 124 Waaula Pl 46 of 50 Listing Image for 124 Waaula Pl 47 of 50 Listing Image for 124 Waaula Pl 48 of 50 Listing Image for 124 Waaula Pl 49 of 50 Listing Image for 124 Waaula Pl 50 of 50

$2,375,000

↓ $300,000

Wailea Kai

124 Waaula Pl, Wailea/Makena

3 Beds 3.5 Baths 2,526 SqFt Residential MLS® # 407403 Date Sold: January 29, 2026
Sold
Closed: 11/21/2025
Listing Image for 26 Luanaiki Pl 1 of 32 Listing Image for 26 Luanaiki Pl 2 of 32 Listing Image for 26 Luanaiki Pl 3 of 32 Listing Image for 26 Luanaiki Pl 4 of 32 Listing Image for 26 Luanaiki Pl 5 of 32 Listing Image for 26 Luanaiki Pl 6 of 32 Listing Image for 26 Luanaiki Pl 7 of 32 Listing Image for 26 Luanaiki Pl 8 of 32 Listing Image for 26 Luanaiki Pl 9 of 32 Listing Image for 26 Luanaiki Pl 10 of 32 Listing Image for 26 Luanaiki Pl 11 of 32 Listing Image for 26 Luanaiki Pl 12 of 32 Listing Image for 26 Luanaiki Pl 13 of 32 Listing Image for 26 Luanaiki Pl 14 of 32 Listing Image for 26 Luanaiki Pl 15 of 32 Listing Image for 26 Luanaiki Pl 16 of 32 Listing Image for 26 Luanaiki Pl 17 of 32 Listing Image for 26 Luanaiki Pl 18 of 32 Listing Image for 26 Luanaiki Pl 19 of 32 Listing Image for 26 Luanaiki Pl 20 of 32 Listing Image for 26 Luanaiki Pl 21 of 32 Listing Image for 26 Luanaiki Pl 22 of 32 Listing Image for 26 Luanaiki Pl 23 of 32 Listing Image for 26 Luanaiki Pl 24 of 32 Listing Image for 26 Luanaiki Pl 25 of 32 Listing Image for 26 Luanaiki Pl 26 of 32 Listing Image for 26 Luanaiki Pl 27 of 32 Listing Image for 26 Luanaiki Pl 28 of 32 Listing Image for 26 Luanaiki Pl 29 of 32 Listing Image for 26 Luanaiki Pl 30 of 32 Listing Image for 26 Luanaiki Pl 31 of 32 Listing Image for 26 Luanaiki Pl 32 of 32

$1,207,750

Keonekai Heights

26 Luanaiki Pl, Kihei

3 Beds 2 Baths 1,200 SqFt Residential MLS® # 407394 Date Sold: November 21, 2025
Sold
Closed: 07/16/2025
255 Prison St, Lahaina

$750,000

Lahaina

255 Prison St, Lahaina

0 Beds 0 Baths 0 SqFt Land MLS® # 407396 Date Sold: July 16, 2025
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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Sold
Closed: 01/07/2026
Listing Image for 17 Door Of Faith Rd 1 of 50 Listing Image for 17 Door Of Faith Rd 2 of 50 Listing Image for 17 Door Of Faith Rd 3 of 50 Listing Image for 17 Door Of Faith Rd 4 of 50 Listing Image for 17 Door Of Faith Rd 5 of 50 Listing Image for 17 Door Of Faith Rd 6 of 50 Listing Image for 17 Door Of Faith Rd 7 of 50 Listing Image for 17 Door Of Faith Rd 8 of 50 Listing Image for 17 Door Of Faith Rd 9 of 50 Listing Image for 17 Door Of Faith Rd 10 of 50 Listing Image for 17 Door Of Faith Rd 11 of 50 Listing Image for 17 Door Of Faith Rd 12 of 50 Listing Image for 17 Door Of Faith Rd 13 of 50 Listing Image for 17 Door Of Faith Rd 14 of 50 Listing Image for 17 Door Of Faith Rd 15 of 50 Listing Image for 17 Door Of Faith Rd 16 of 50 Listing Image for 17 Door Of Faith Rd 17 of 50 Listing Image for 17 Door Of Faith Rd 18 of 50 Listing Image for 17 Door Of Faith Rd 19 of 50 Listing Image for 17 Door Of Faith Rd 20 of 50 Listing Image for 17 Door Of Faith Rd 21 of 50 Listing Image for 17 Door Of Faith Rd 22 of 50 Listing Image for 17 Door Of Faith Rd 23 of 50 Listing Image for 17 Door Of Faith Rd 24 of 50 Listing Image for 17 Door Of Faith Rd 25 of 50 Listing Image for 17 Door Of Faith Rd 26 of 50 Listing Image for 17 Door Of Faith Rd 27 of 50 Listing Image for 17 Door Of Faith Rd 28 of 50 Listing Image for 17 Door Of Faith Rd 29 of 50 Listing Image for 17 Door Of Faith Rd 30 of 50 Listing Image for 17 Door Of Faith Rd 31 of 50 Listing Image for 17 Door Of Faith Rd 32 of 50 Listing Image for 17 Door Of Faith Rd 33 of 50 Listing Image for 17 Door Of Faith Rd 34 of 50 Listing Image for 17 Door Of Faith Rd 35 of 50 Listing Image for 17 Door Of Faith Rd 36 of 50 Listing Image for 17 Door Of Faith Rd 37 of 50 Listing Image for 17 Door Of Faith Rd 38 of 50 Listing Image for 17 Door Of Faith Rd 39 of 50 Listing Image for 17 Door Of Faith Rd 40 of 50 Listing Image for 17 Door Of Faith Rd 41 of 50 Listing Image for 17 Door Of Faith Rd 42 of 50 Listing Image for 17 Door Of Faith Rd 43 of 50 Listing Image for 17 Door Of Faith Rd 44 of 50 Listing Image for 17 Door Of Faith Rd 45 of 50 Listing Image for 17 Door Of Faith Rd 46 of 50 Listing Image for 17 Door Of Faith Rd 47 of 50 Listing Image for 17 Door Of Faith Rd 48 of 50 Listing Image for 17 Door Of Faith Rd 49 of 50 Listing Image for 17 Door Of Faith Rd 50 of 50

$1,350,000

Door of Faith

17 Door Of Faith Rd, Haiku

3 Beds 3 Baths 1,886 SqFt Residential MLS® # 407391 Date Sold: January 7, 2026
Sold
Closed: 09/03/2026
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$750,000

Mahana 612

110 Kaanapali Shores Pl 612, Kaanapali

0 Beds 1 Bath 456 SqFt Residential MLS® # 407387 Date Sold: September 3, 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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