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 4950 Uakea Rd 1 of 39 Listing Image for 4950 Uakea Rd 2 of 39 Listing Image for 4950 Uakea Rd 3 of 39 Listing Image for 4950 Uakea Rd 4 of 39 Listing Image for 4950 Uakea Rd 5 of 39 Listing Image for 4950 Uakea Rd 6 of 39 Listing Image for 4950 Uakea Rd 7 of 39 Listing Image for 4950 Uakea Rd 8 of 39 Listing Image for 4950 Uakea Rd 9 of 39 Listing Image for 4950 Uakea Rd 10 of 39 Listing Image for 4950 Uakea Rd 11 of 39 Listing Image for 4950 Uakea Rd 12 of 39 Listing Image for 4950 Uakea Rd 13 of 39 Listing Image for 4950 Uakea Rd 14 of 39 Listing Image for 4950 Uakea Rd 15 of 39 Listing Image for 4950 Uakea Rd 16 of 39 Listing Image for 4950 Uakea Rd 17 of 39 Listing Image for 4950 Uakea Rd 18 of 39 Listing Image for 4950 Uakea Rd 19 of 39 Listing Image for 4950 Uakea Rd 20 of 39 Listing Image for 4950 Uakea Rd 21 of 39 Listing Image for 4950 Uakea Rd 22 of 39 Listing Image for 4950 Uakea Rd 23 of 39 Listing Image for 4950 Uakea Rd 24 of 39 Listing Image for 4950 Uakea Rd 25 of 39 Listing Image for 4950 Uakea Rd 26 of 39 Listing Image for 4950 Uakea Rd 27 of 39 Listing Image for 4950 Uakea Rd 28 of 39 Listing Image for 4950 Uakea Rd 29 of 39 Listing Image for 4950 Uakea Rd 30 of 39 Listing Image for 4950 Uakea Rd 31 of 39 Listing Image for 4950 Uakea Rd 32 of 39 Listing Image for 4950 Uakea Rd 33 of 39 Listing Image for 4950 Uakea Rd 34 of 39 Listing Image for 4950 Uakea Rd 35 of 39 Listing Image for 4950 Uakea Rd 36 of 39 Listing Image for 4950 Uakea Rd 37 of 39 Listing Image for 4950 Uakea Rd 38 of 39 Listing Image for 4950 Uakea Rd 39 of 39

$1,999,000

↓ $396,000

Hana

4950 Uakea Rd, Hana

4 Beds 3 Baths 2,332 SqFt Residential MLS® # 405129

Days on Market: 565

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

Listing Image for 200/206 Awawa Rd 1 of 24 Listing Image for 200/206 Awawa Rd 2 of 24 Listing Image for 200/206 Awawa Rd 3 of 24 Listing Image for 200/206 Awawa Rd 4 of 24 Listing Image for 200/206 Awawa Rd 5 of 24 Listing Image for 200/206 Awawa Rd 6 of 24 Listing Image for 200/206 Awawa Rd 7 of 24 Listing Image for 200/206 Awawa Rd 8 of 24 Listing Image for 200/206 Awawa Rd 9 of 24 Listing Image for 200/206 Awawa Rd 10 of 24 Listing Image for 200/206 Awawa Rd 11 of 24 Listing Image for 200/206 Awawa Rd 12 of 24 Listing Image for 200/206 Awawa Rd 13 of 24 Listing Image for 200/206 Awawa Rd 14 of 24 Listing Image for 200/206 Awawa Rd 15 of 24 Listing Image for 200/206 Awawa Rd 16 of 24 Listing Image for 200/206 Awawa Rd 17 of 24 Listing Image for 200/206 Awawa Rd 18 of 24 Listing Image for 200/206 Awawa Rd 19 of 24 Listing Image for 200/206 Awawa Rd 20 of 24 Listing Image for 200/206 Awawa Rd 21 of 24 Listing Image for 200/206 Awawa Rd 22 of 24 Listing Image for 200/206 Awawa Rd 23 of 24 Listing Image for 200/206 Awawa Rd 24 of 24

$1,188,000

↓ $91,000

Molokai

200/206 Awawa Rd, Molokai

3 Beds 3 Baths 1,920 SqFt Residential MLS® # 403418

Days on Market: 738

Jeffrey Samuels Realty

Short Term Rental
Listing Image for 155 Wailea Ike Pl 140 1 of 43 Listing Image for 155 Wailea Ike Pl 140 2 of 43 Listing Image for 155 Wailea Ike Pl 140 3 of 43 Listing Image for 155 Wailea Ike Pl 140 4 of 43 Listing Image for 155 Wailea Ike Pl 140 5 of 43 Listing Image for 155 Wailea Ike Pl 140 6 of 43 Listing Image for 155 Wailea Ike Pl 140 7 of 43 Listing Image for 155 Wailea Ike Pl 140 8 of 43 Listing Image for 155 Wailea Ike Pl 140 9 of 43 Listing Image for 155 Wailea Ike Pl 140 10 of 43 Listing Image for 155 Wailea Ike Pl 140 11 of 43 Listing Image for 155 Wailea Ike Pl 140 12 of 43 Listing Image for 155 Wailea Ike Pl 140 13 of 43 Listing Image for 155 Wailea Ike Pl 140 14 of 43 Listing Image for 155 Wailea Ike Pl 140 15 of 43 Listing Image for 155 Wailea Ike Pl 140 16 of 43 Listing Image for 155 Wailea Ike Pl 140 17 of 43 Listing Image for 155 Wailea Ike Pl 140 18 of 43 Listing Image for 155 Wailea Ike Pl 140 19 of 43 Listing Image for 155 Wailea Ike Pl 140 20 of 43 Listing Image for 155 Wailea Ike Pl 140 21 of 43 Listing Image for 155 Wailea Ike Pl 140 22 of 43 Listing Image for 155 Wailea Ike Pl 140 23 of 43 Listing Image for 155 Wailea Ike Pl 140 24 of 43 Listing Image for 155 Wailea Ike Pl 140 25 of 43 Listing Image for 155 Wailea Ike Pl 140 26 of 43 Listing Image for 155 Wailea Ike Pl 140 27 of 43 Listing Image for 155 Wailea Ike Pl 140 28 of 43 Listing Image for 155 Wailea Ike Pl 140 29 of 43 Listing Image for 155 Wailea Ike Pl 140 30 of 43 Listing Image for 155 Wailea Ike Pl 140 31 of 43 Listing Image for 155 Wailea Ike Pl 140 32 of 43 Listing Image for 155 Wailea Ike Pl 140 33 of 43 Listing Image for 155 Wailea Ike Pl 140 34 of 43 Listing Image for 155 Wailea Ike Pl 140 35 of 43 Listing Image for 155 Wailea Ike Pl 140 36 of 43 Listing Image for 155 Wailea Ike Pl 140 37 of 43 Listing Image for 155 Wailea Ike Pl 140 38 of 43 Listing Image for 155 Wailea Ike Pl 140 39 of 43 Listing Image for 155 Wailea Ike Pl 140 40 of 43 Listing Image for 155 Wailea Ike Pl 140 41 of 43 Listing Image for 155 Wailea Ike Pl 140 42 of 43 Listing Image for 155 Wailea Ike Pl 140 43 of 43

$1,045,000

↓ $154,000

Grand Champions 140

155 Wailea Ike Pl 140, Wailea/Makena

2 Beds 2 Baths 1,056 SqFt Residential MLS® # 403638

Days on Market: 713

Maui Real Estate Advisors LLC 808-875-4444

Short Term Rental
Listing Image for 1 Bay Dr 3503 1 of 44 Listing Image for 1 Bay Dr 3503 2 of 44 Listing Image for 1 Bay Dr 3503 3 of 44 Listing Image for 1 Bay Dr 3503 4 of 44 Listing Image for 1 Bay Dr 3503 5 of 44 Listing Image for 1 Bay Dr 3503 6 of 44 Listing Image for 1 Bay Dr 3503 7 of 44 Listing Image for 1 Bay Dr 3503 8 of 44 Listing Image for 1 Bay Dr 3503 9 of 44 Listing Image for 1 Bay Dr 3503 10 of 44 Listing Image for 1 Bay Dr 3503 11 of 44 Listing Image for 1 Bay Dr 3503 12 of 44 Listing Image for 1 Bay Dr 3503 13 of 44 Listing Image for 1 Bay Dr 3503 14 of 44 Listing Image for 1 Bay Dr 3503 15 of 44 Listing Image for 1 Bay Dr 3503 16 of 44 Listing Image for 1 Bay Dr 3503 17 of 44 Listing Image for 1 Bay Dr 3503 18 of 44 Listing Image for 1 Bay Dr 3503 19 of 44 Listing Image for 1 Bay Dr 3503 20 of 44 Listing Image for 1 Bay Dr 3503 21 of 44 Listing Image for 1 Bay Dr 3503 22 of 44 Listing Image for 1 Bay Dr 3503 23 of 44 Listing Image for 1 Bay Dr 3503 24 of 44 Listing Image for 1 Bay Dr 3503 25 of 44 Listing Image for 1 Bay Dr 3503 26 of 44 Listing Image for 1 Bay Dr 3503 27 of 44 Listing Image for 1 Bay Dr 3503 28 of 44 Listing Image for 1 Bay Dr 3503 29 of 44 Listing Image for 1 Bay Dr 3503 30 of 44 Listing Image for 1 Bay Dr 3503 31 of 44 Listing Image for 1 Bay Dr 3503 32 of 44 Listing Image for 1 Bay Dr 3503 33 of 44 Listing Image for 1 Bay Dr 3503 34 of 44 Listing Image for 1 Bay Dr 3503 35 of 44 Listing Image for 1 Bay Dr 3503 36 of 44 Listing Image for 1 Bay Dr 3503 37 of 44 Listing Image for 1 Bay Dr 3503 38 of 44 Listing Image for 1 Bay Dr 3503 39 of 44 Listing Image for 1 Bay Dr 3503 40 of 44 Listing Image for 1 Bay Dr 3503 41 of 44 Listing Image for 1 Bay Dr 3503 42 of 44 Listing Image for 1 Bay Dr 3503 43 of 44 Listing Image for 1 Bay Dr 3503 44 of 44

$5,460,000

↑ $961,000

Montage Residences Kapalua Bay 3503

1 Bay Dr 3503, Kapalua

3 Beds 3.5 Baths 2,065 SqFt Residential MLS® # 405113

Days on Market: 566

Keller Williams Realty Maui-Ki Cell: 808-371-6475

Listing Image for 1756 Halama St 1 of 6 Listing Image for 1756 Halama St 2 of 6 Listing Image for 1756 Halama St 3 of 6 Listing Image for 1756 Halama St 4 of 6 Listing Image for 1756 Halama St 5 of 6 Listing Image for 1756 Halama St 6 of 6

$5,999,000

Waiohuli Keokea Beach Lt

1756 Halama St, Kihei

3 Beds 2 Baths 1,412 SqFt Residential MLS® # 404090

Days on Market: 728

Five Star Realty Inc.

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

$14,750,000

↓ $1,250,000

Maluhia at Wailea

19 Malukai Ln 4, Wailea/Makena

4 Beds 4.5 Baths 4,803 SqFt Residential MLS® # 405257

Days on Market: 553

Hawaii Life (W) Cell: 808-283-2222

Short Term Rental
Listing Image for 3823 Lower Honoapiilani Rd 208 1 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 2 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 3 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 4 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 5 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 6 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 7 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 8 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 9 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 10 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 11 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 12 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 13 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 14 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 15 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 16 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 17 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 18 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 19 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 20 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 21 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 22 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 23 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 24 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 25 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 26 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 27 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 28 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 29 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 30 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 31 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 32 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 33 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 34 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 35 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 36 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 37 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 38 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 39 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 40 of 41 Listing Image for 3823 Lower Honoapiilani Rd 208 41 of 41

$874,000

Hale Ono Loa 208

3823 Lower Honoapiilani Rd 208, Napili/Kahana/Honokowai

1 Bed 1 Bath 558 SqFt Residential MLS® # 404772

Days on Market: 600

Coldwell Banker Island Prop-KP Cell: 808-281-7313

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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: 07/28/2025
Listing Image for 2709 Puu Hoolai St 1 of 50 Listing Image for 2709 Puu Hoolai St 2 of 50 Listing Image for 2709 Puu Hoolai St 3 of 50 Listing Image for 2709 Puu Hoolai St 4 of 50 Listing Image for 2709 Puu Hoolai St 5 of 50 Listing Image for 2709 Puu Hoolai St 6 of 50 Listing Image for 2709 Puu Hoolai St 7 of 50 Listing Image for 2709 Puu Hoolai St 8 of 50 Listing Image for 2709 Puu Hoolai St 9 of 50 Listing Image for 2709 Puu Hoolai St 10 of 50 Listing Image for 2709 Puu Hoolai St 11 of 50 Listing Image for 2709 Puu Hoolai St 12 of 50 Listing Image for 2709 Puu Hoolai St 13 of 50 Listing Image for 2709 Puu Hoolai St 14 of 50 Listing Image for 2709 Puu Hoolai St 15 of 50 Listing Image for 2709 Puu Hoolai St 16 of 50 Listing Image for 2709 Puu Hoolai St 17 of 50 Listing Image for 2709 Puu Hoolai St 18 of 50 Listing Image for 2709 Puu Hoolai St 19 of 50 Listing Image for 2709 Puu Hoolai St 20 of 50 Listing Image for 2709 Puu Hoolai St 21 of 50 Listing Image for 2709 Puu Hoolai St 22 of 50 Listing Image for 2709 Puu Hoolai St 23 of 50 Listing Image for 2709 Puu Hoolai St 24 of 50 Listing Image for 2709 Puu Hoolai St 25 of 50 Listing Image for 2709 Puu Hoolai St 26 of 50 Listing Image for 2709 Puu Hoolai St 27 of 50 Listing Image for 2709 Puu Hoolai St 28 of 50 Listing Image for 2709 Puu Hoolai St 29 of 50 Listing Image for 2709 Puu Hoolai St 30 of 50 Listing Image for 2709 Puu Hoolai St 31 of 50 Listing Image for 2709 Puu Hoolai St 32 of 50 Listing Image for 2709 Puu Hoolai St 33 of 50 Listing Image for 2709 Puu Hoolai St 34 of 50 Listing Image for 2709 Puu Hoolai St 35 of 50 Listing Image for 2709 Puu Hoolai St 36 of 50 Listing Image for 2709 Puu Hoolai St 37 of 50 Listing Image for 2709 Puu Hoolai St 38 of 50 Listing Image for 2709 Puu Hoolai St 39 of 50 Listing Image for 2709 Puu Hoolai St 40 of 50 Listing Image for 2709 Puu Hoolai St 41 of 50 Listing Image for 2709 Puu Hoolai St 42 of 50 Listing Image for 2709 Puu Hoolai St 43 of 50 Listing Image for 2709 Puu Hoolai St 44 of 50 Listing Image for 2709 Puu Hoolai St 45 of 50 Listing Image for 2709 Puu Hoolai St 46 of 50 Listing Image for 2709 Puu Hoolai St 47 of 50 Listing Image for 2709 Puu Hoolai St 48 of 50 Listing Image for 2709 Puu Hoolai St 49 of 50 Listing Image for 2709 Puu Hoolai St 50 of 50

$1,525,000

Kihei

2709 Puu Hoolai St, Kihei

3 Beds 2.5 Baths 2,180 SqFt Residential MLS® # 405236 Date Sold: July 28, 2025
Sold
Closed: 11/05/2025
Listing Image for 2737 S Kihei Rd 3-251 1 of 43 Listing Image for 2737 S Kihei Rd 3-251 2 of 43 Listing Image for 2737 S Kihei Rd 3-251 3 of 43 Listing Image for 2737 S Kihei Rd 3-251 4 of 43 Listing Image for 2737 S Kihei Rd 3-251 5 of 43 Listing Image for 2737 S Kihei Rd 3-251 6 of 43 Listing Image for 2737 S Kihei Rd 3-251 7 of 43 Listing Image for 2737 S Kihei Rd 3-251 8 of 43 Listing Image for 2737 S Kihei Rd 3-251 9 of 43 Listing Image for 2737 S Kihei Rd 3-251 10 of 43 Listing Image for 2737 S Kihei Rd 3-251 11 of 43 Listing Image for 2737 S Kihei Rd 3-251 12 of 43 Listing Image for 2737 S Kihei Rd 3-251 13 of 43 Listing Image for 2737 S Kihei Rd 3-251 14 of 43 Listing Image for 2737 S Kihei Rd 3-251 15 of 43 Listing Image for 2737 S Kihei Rd 3-251 16 of 43 Listing Image for 2737 S Kihei Rd 3-251 17 of 43 Listing Image for 2737 S Kihei Rd 3-251 18 of 43 Listing Image for 2737 S Kihei Rd 3-251 19 of 43 Listing Image for 2737 S Kihei Rd 3-251 20 of 43 Listing Image for 2737 S Kihei Rd 3-251 21 of 43 Listing Image for 2737 S Kihei Rd 3-251 22 of 43 Listing Image for 2737 S Kihei Rd 3-251 23 of 43 Listing Image for 2737 S Kihei Rd 3-251 24 of 43 Listing Image for 2737 S Kihei Rd 3-251 25 of 43 Listing Image for 2737 S Kihei Rd 3-251 26 of 43 Listing Image for 2737 S Kihei Rd 3-251 27 of 43 Listing Image for 2737 S Kihei Rd 3-251 28 of 43 Listing Image for 2737 S Kihei Rd 3-251 29 of 43 Listing Image for 2737 S Kihei Rd 3-251 30 of 43 Listing Image for 2737 S Kihei Rd 3-251 31 of 43 Listing Image for 2737 S Kihei Rd 3-251 32 of 43 Listing Image for 2737 S Kihei Rd 3-251 33 of 43 Listing Image for 2737 S Kihei Rd 3-251 34 of 43 Listing Image for 2737 S Kihei Rd 3-251 35 of 43 Listing Image for 2737 S Kihei Rd 3-251 36 of 43 Listing Image for 2737 S Kihei Rd 3-251 37 of 43 Listing Image for 2737 S Kihei Rd 3-251 38 of 43 Listing Image for 2737 S Kihei Rd 3-251 39 of 43 Listing Image for 2737 S Kihei Rd 3-251 40 of 43 Listing Image for 2737 S Kihei Rd 3-251 41 of 43 Listing Image for 2737 S Kihei Rd 3-251 42 of 43 Listing Image for 2737 S Kihei Rd 3-251 43 of 43

$925,000

↓ $125,000

Hale Kamaole 3-251

2737 S Kihei Rd 3-251, Kihei

2 Beds 2 Baths 1,112 SqFt Residential MLS® # 406803 Date Sold: November 5, 2025
Sold
Closed: 09/12/2025
Listing Image for 115 Luluka Pl 1 of 46 Listing Image for 115 Luluka Pl 2 of 46 Listing Image for 115 Luluka Pl 3 of 46 Listing Image for 115 Luluka Pl 4 of 46 Listing Image for 115 Luluka Pl 5 of 46 Listing Image for 115 Luluka Pl 6 of 46 Listing Image for 115 Luluka Pl 7 of 46 Listing Image for 115 Luluka Pl 8 of 46 Listing Image for 115 Luluka Pl 9 of 46 Listing Image for 115 Luluka Pl 10 of 46 Listing Image for 115 Luluka Pl 11 of 46 Listing Image for 115 Luluka Pl 12 of 46 Listing Image for 115 Luluka Pl 13 of 46 Listing Image for 115 Luluka Pl 14 of 46 Listing Image for 115 Luluka Pl 15 of 46 Listing Image for 115 Luluka Pl 16 of 46 Listing Image for 115 Luluka Pl 17 of 46 Listing Image for 115 Luluka Pl 18 of 46 Listing Image for 115 Luluka Pl 19 of 46 Listing Image for 115 Luluka Pl 20 of 46 Listing Image for 115 Luluka Pl 21 of 46 Listing Image for 115 Luluka Pl 22 of 46 Listing Image for 115 Luluka Pl 23 of 46 Listing Image for 115 Luluka Pl 24 of 46 Listing Image for 115 Luluka Pl 25 of 46 Listing Image for 115 Luluka Pl 26 of 46 Listing Image for 115 Luluka Pl 27 of 46 Listing Image for 115 Luluka Pl 28 of 46 Listing Image for 115 Luluka Pl 29 of 46 Listing Image for 115 Luluka Pl 30 of 46 Listing Image for 115 Luluka Pl 31 of 46 Listing Image for 115 Luluka Pl 32 of 46 Listing Image for 115 Luluka Pl 33 of 46 Listing Image for 115 Luluka Pl 34 of 46 Listing Image for 115 Luluka Pl 35 of 46 Listing Image for 115 Luluka Pl 36 of 46 Listing Image for 115 Luluka Pl 37 of 46 Listing Image for 115 Luluka Pl 38 of 46 Listing Image for 115 Luluka Pl 39 of 46 Listing Image for 115 Luluka Pl 40 of 46 Listing Image for 115 Luluka Pl 41 of 46 Listing Image for 115 Luluka Pl 42 of 46 Listing Image for 115 Luluka Pl 43 of 46 Listing Image for 115 Luluka Pl 44 of 46 Listing Image for 115 Luluka Pl 45 of 46 Listing Image for 115 Luluka Pl 46 of 46

$960,000

Kihei

115 Luluka Pl, Kihei

3 Beds 3 Baths 1,440 SqFt Residential MLS® # 406696 Date Sold: September 12, 2025
Sold
Closed: 10/20/2025
Listing Image for 2630 Kanakanui Rd 1 of 33 Listing Image for 2630 Kanakanui Rd 2 of 33 Listing Image for 2630 Kanakanui Rd 3 of 33 Listing Image for 2630 Kanakanui Rd 4 of 33 Listing Image for 2630 Kanakanui Rd 5 of 33 Listing Image for 2630 Kanakanui Rd 6 of 33 Listing Image for 2630 Kanakanui Rd 7 of 33 Listing Image for 2630 Kanakanui Rd 8 of 33 Listing Image for 2630 Kanakanui Rd 9 of 33 Listing Image for 2630 Kanakanui Rd 10 of 33 Listing Image for 2630 Kanakanui Rd 11 of 33 Listing Image for 2630 Kanakanui Rd 12 of 33 Listing Image for 2630 Kanakanui Rd 13 of 33 Listing Image for 2630 Kanakanui Rd 14 of 33 Listing Image for 2630 Kanakanui Rd 15 of 33 Listing Image for 2630 Kanakanui Rd 16 of 33 Listing Image for 2630 Kanakanui Rd 17 of 33 Listing Image for 2630 Kanakanui Rd 18 of 33 Listing Image for 2630 Kanakanui Rd 19 of 33 Listing Image for 2630 Kanakanui Rd 20 of 33 Listing Image for 2630 Kanakanui Rd 21 of 33 Listing Image for 2630 Kanakanui Rd 22 of 33 Listing Image for 2630 Kanakanui Rd 23 of 33 Listing Image for 2630 Kanakanui Rd 24 of 33 Listing Image for 2630 Kanakanui Rd 25 of 33 Listing Image for 2630 Kanakanui Rd 26 of 33 Listing Image for 2630 Kanakanui Rd 27 of 33 Listing Image for 2630 Kanakanui Rd 28 of 33 Listing Image for 2630 Kanakanui Rd 29 of 33 Listing Image for 2630 Kanakanui Rd 30 of 33 Listing Image for 2630 Kanakanui Rd 31 of 33 Listing Image for 2630 Kanakanui Rd 32 of 33 Listing Image for 2630 Kanakanui Rd 33 of 33

$1,100,000

Kihei

2630 Kanakanui Rd, Kihei

4 Beds 4 Baths 3,291 SqFt Residential MLS® # 405374 Date Sold: October 20, 2025
Buying Real Estate on Maui

Buying Real Estate on Maui

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Sold
Closed: 07/29/2025
Listing Image for 610 Kailana St 1 of 46 Listing Image for 610 Kailana St 2 of 46 Listing Image for 610 Kailana St 3 of 46 Listing Image for 610 Kailana St 4 of 46 Listing Image for 610 Kailana St 5 of 46 Listing Image for 610 Kailana St 6 of 46 Listing Image for 610 Kailana St 7 of 46 Listing Image for 610 Kailana St 8 of 46 Listing Image for 610 Kailana St 9 of 46 Listing Image for 610 Kailana St 10 of 46 Listing Image for 610 Kailana St 11 of 46 Listing Image for 610 Kailana St 12 of 46 Listing Image for 610 Kailana St 13 of 46 Listing Image for 610 Kailana St 14 of 46 Listing Image for 610 Kailana St 15 of 46 Listing Image for 610 Kailana St 16 of 46 Listing Image for 610 Kailana St 17 of 46 Listing Image for 610 Kailana St 18 of 46 Listing Image for 610 Kailana St 19 of 46 Listing Image for 610 Kailana St 20 of 46 Listing Image for 610 Kailana St 21 of 46 Listing Image for 610 Kailana St 22 of 46 Listing Image for 610 Kailana St 23 of 46 Listing Image for 610 Kailana St 24 of 46 Listing Image for 610 Kailana St 25 of 46 Listing Image for 610 Kailana St 26 of 46 Listing Image for 610 Kailana St 27 of 46 Listing Image for 610 Kailana St 28 of 46 Listing Image for 610 Kailana St 29 of 46 Listing Image for 610 Kailana St 30 of 46 Listing Image for 610 Kailana St 31 of 46 Listing Image for 610 Kailana St 32 of 46 Listing Image for 610 Kailana St 33 of 46 Listing Image for 610 Kailana St 34 of 46 Listing Image for 610 Kailana St 35 of 46 Listing Image for 610 Kailana St 36 of 46 Listing Image for 610 Kailana St 37 of 46 Listing Image for 610 Kailana St 38 of 46 Listing Image for 610 Kailana St 39 of 46 Listing Image for 610 Kailana St 40 of 46 Listing Image for 610 Kailana St 41 of 46 Listing Image for 610 Kailana St 42 of 46 Listing Image for 610 Kailana St 43 of 46 Listing Image for 610 Kailana St 44 of 46 Listing Image for 610 Kailana St 45 of 46 Listing Image for 610 Kailana St 46 of 46

$855,000

Wailuku

610 Kailana St, Wailuku

2 Beds 2 Baths 1,116 SqFt Residential MLS® # 405898 Date Sold: July 29, 2025
Sold
Closed: 09/05/2025
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$6,485,000

Wailea Golf Estates

3885 Wailea Ekolu Pl, Wailea/Makena

4 Beds 3.5 Baths 4,588 SqFt Residential MLS® # 404575 Date Sold: September 5, 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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