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 390 Pualoa Nani Pl 1 of 50 Listing Image for 390 Pualoa Nani Pl 2 of 50 Listing Image for 390 Pualoa Nani Pl 3 of 50 Listing Image for 390 Pualoa Nani Pl 4 of 50 Listing Image for 390 Pualoa Nani Pl 5 of 50 Listing Image for 390 Pualoa Nani Pl 6 of 50 Listing Image for 390 Pualoa Nani Pl 7 of 50 Listing Image for 390 Pualoa Nani Pl 8 of 50 Listing Image for 390 Pualoa Nani Pl 9 of 50 Listing Image for 390 Pualoa Nani Pl 10 of 50 Listing Image for 390 Pualoa Nani Pl 11 of 50 Listing Image for 390 Pualoa Nani Pl 12 of 50 Listing Image for 390 Pualoa Nani Pl 13 of 50 Listing Image for 390 Pualoa Nani Pl 14 of 50 Listing Image for 390 Pualoa Nani Pl 15 of 50 Listing Image for 390 Pualoa Nani Pl 16 of 50 Listing Image for 390 Pualoa Nani Pl 17 of 50 Listing Image for 390 Pualoa Nani Pl 18 of 50 Listing Image for 390 Pualoa Nani Pl 19 of 50 Listing Image for 390 Pualoa Nani Pl 20 of 50 Listing Image for 390 Pualoa Nani Pl 21 of 50 Listing Image for 390 Pualoa Nani Pl 22 of 50 Listing Image for 390 Pualoa Nani Pl 23 of 50 Listing Image for 390 Pualoa Nani Pl 24 of 50 Listing Image for 390 Pualoa Nani Pl 25 of 50 Listing Image for 390 Pualoa Nani Pl 26 of 50 Listing Image for 390 Pualoa Nani Pl 27 of 50 Listing Image for 390 Pualoa Nani Pl 28 of 50 Listing Image for 390 Pualoa Nani Pl 29 of 50 Listing Image for 390 Pualoa Nani Pl 30 of 50 Listing Image for 390 Pualoa Nani Pl 31 of 50 Listing Image for 390 Pualoa Nani Pl 32 of 50 Listing Image for 390 Pualoa Nani Pl 33 of 50 Listing Image for 390 Pualoa Nani Pl 34 of 50 Listing Image for 390 Pualoa Nani Pl 35 of 50 Listing Image for 390 Pualoa Nani Pl 36 of 50 Listing Image for 390 Pualoa Nani Pl 37 of 50 Listing Image for 390 Pualoa Nani Pl 38 of 50 Listing Image for 390 Pualoa Nani Pl 39 of 50 Listing Image for 390 Pualoa Nani Pl 40 of 50 Listing Image for 390 Pualoa Nani Pl 41 of 50 Listing Image for 390 Pualoa Nani Pl 42 of 50 Listing Image for 390 Pualoa Nani Pl 43 of 50 Listing Image for 390 Pualoa Nani Pl 44 of 50 Listing Image for 390 Pualoa Nani Pl 45 of 50 Listing Image for 390 Pualoa Nani Pl 46 of 50 Listing Image for 390 Pualoa Nani Pl 47 of 50 Listing Image for 390 Pualoa Nani Pl 48 of 50 Listing Image for 390 Pualoa Nani Pl 49 of 50 Listing Image for 390 Pualoa Nani Pl 50 of 50

$3,785,000

↓ $110,000

Wailea Pualani

390 Pualoa Nani Pl, Wailea/Makena

4 Beds 3.5 Baths 2,569 SqFt Residential MLS® # 409908

Days on Market: 95

Engel & Volkers Maui

In Escrow
Listing Image for 5177 Hanawai St F 1 of 44 Listing Image for 5177 Hanawai St F 2 of 44 Listing Image for 5177 Hanawai St F 3 of 44 Listing Image for 5177 Hanawai St F 4 of 44 Listing Image for 5177 Hanawai St F 5 of 44 Listing Image for 5177 Hanawai St F 6 of 44 Listing Image for 5177 Hanawai St F 7 of 44 Listing Image for 5177 Hanawai St F 8 of 44 Listing Image for 5177 Hanawai St F 9 of 44 Listing Image for 5177 Hanawai St F 10 of 44 Listing Image for 5177 Hanawai St F 11 of 44 Listing Image for 5177 Hanawai St F 12 of 44 Listing Image for 5177 Hanawai St F 13 of 44 Listing Image for 5177 Hanawai St F 14 of 44 Listing Image for 5177 Hanawai St F 15 of 44 Listing Image for 5177 Hanawai St F 16 of 44 Listing Image for 5177 Hanawai St F 17 of 44 Listing Image for 5177 Hanawai St F 18 of 44 Listing Image for 5177 Hanawai St F 19 of 44 Listing Image for 5177 Hanawai St F 20 of 44 Listing Image for 5177 Hanawai St F 21 of 44 Listing Image for 5177 Hanawai St F 22 of 44 Listing Image for 5177 Hanawai St F 23 of 44 Listing Image for 5177 Hanawai St F 24 of 44 Listing Image for 5177 Hanawai St F 25 of 44 Listing Image for 5177 Hanawai St F 26 of 44 Listing Image for 5177 Hanawai St F 27 of 44 Listing Image for 5177 Hanawai St F 28 of 44 Listing Image for 5177 Hanawai St F 29 of 44 Listing Image for 5177 Hanawai St F 30 of 44 Listing Image for 5177 Hanawai St F 31 of 44 Listing Image for 5177 Hanawai St F 32 of 44 Listing Image for 5177 Hanawai St F 33 of 44 Listing Image for 5177 Hanawai St F 34 of 44 Listing Image for 5177 Hanawai St F 35 of 44 Listing Image for 5177 Hanawai St F 36 of 44 Listing Image for 5177 Hanawai St F 37 of 44 Listing Image for 5177 Hanawai St F 38 of 44 Listing Image for 5177 Hanawai St F 39 of 44 Listing Image for 5177 Hanawai St F 40 of 44 Listing Image for 5177 Hanawai St F 41 of 44 Listing Image for 5177 Hanawai St F 42 of 44 Listing Image for 5177 Hanawai St F 43 of 44 Listing Image for 5177 Hanawai St F 44 of 44

$1,049,000

↓ $26,000

Napili/Kahana/Honokowai

5177 Hanawai St F, Napili/Kahana/Honokowai

3 Beds 2 Baths 1,404 SqFt Residential MLS® # 409906

Days on Market: 95

Keller Williams Realty Maui-Ka Cell: 808-542-8059

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

$2,495,000

Kaonoulu Lots

16 Kekaulike Ave, Kula/Ulupalakua/Kanaio

4 Beds 3.5 Baths 4,127 SqFt Residential MLS® # 409902

Days on Market: 96

Compass-W

Short Term Rental
Listing Image for 2575 S Kihei Rd P 310 1 of 30 Listing Image for 2575 S Kihei Rd P 310 2 of 30 Listing Image for 2575 S Kihei Rd P 310 3 of 30 Listing Image for 2575 S Kihei Rd P 310 4 of 30 Listing Image for 2575 S Kihei Rd P 310 5 of 30 Listing Image for 2575 S Kihei Rd P 310 6 of 30 Listing Image for 2575 S Kihei Rd P 310 7 of 30 Listing Image for 2575 S Kihei Rd P 310 8 of 30 Listing Image for 2575 S Kihei Rd P 310 9 of 30 Listing Image for 2575 S Kihei Rd P 310 10 of 30 Listing Image for 2575 S Kihei Rd P 310 11 of 30 Listing Image for 2575 S Kihei Rd P 310 12 of 30 Listing Image for 2575 S Kihei Rd P 310 13 of 30 Listing Image for 2575 S Kihei Rd P 310 14 of 30 Listing Image for 2575 S Kihei Rd P 310 15 of 30 Listing Image for 2575 S Kihei Rd P 310 16 of 30 Listing Image for 2575 S Kihei Rd P 310 17 of 30 Listing Image for 2575 S Kihei Rd P 310 18 of 30 Listing Image for 2575 S Kihei Rd P 310 19 of 30 Listing Image for 2575 S Kihei Rd P 310 20 of 30 Listing Image for 2575 S Kihei Rd P 310 21 of 30 Listing Image for 2575 S Kihei Rd P 310 22 of 30 Listing Image for 2575 S Kihei Rd P 310 23 of 30 Listing Image for 2575 S Kihei Rd P 310 24 of 30 Listing Image for 2575 S Kihei Rd P 310 25 of 30 Listing Image for 2575 S Kihei Rd P 310 26 of 30 Listing Image for 2575 S Kihei Rd P 310 27 of 30 Listing Image for 2575 S Kihei Rd P 310 28 of 30 Listing Image for 2575 S Kihei Rd P 310 29 of 30 Listing Image for 2575 S Kihei Rd P 310 30 of 30

$1,250,000

Maui Banyan P 310

2575 S Kihei Rd P 310, Kihei

2 Beds 2 Baths 890 SqFt Residential MLS® # 409895

Days on Market: 96

AOK Properties LLC Cell: 808-280-7929

Short Term Rental
Listing Image for 3200 Wailea Alanui Dr 1605 1 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 2 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 3 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 4 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 5 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 6 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 7 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 8 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 9 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 10 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 11 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 12 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 13 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 14 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 15 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 16 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 17 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 18 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 19 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 20 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 21 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 22 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 23 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 24 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 25 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 26 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 27 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 28 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 29 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 30 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 31 of 32 Listing Image for 3200 Wailea Alanui Dr 1605 32 of 32

$1,275,000

Palms at Wailea 1605

3200 Wailea Alanui Dr 1605, Wailea/Makena

2 Beds 2 Baths 1,242 SqFt Residential MLS® # 407528

Days on Market: 325

Island Sotheby's International Realty(W) Cell: 808-385-6564

Listing Image for 162 Koheo Rd 1 of 50 Listing Image for 162 Koheo Rd 2 of 50 Listing Image for 162 Koheo Rd 3 of 50 Listing Image for 162 Koheo Rd 4 of 50 Listing Image for 162 Koheo Rd 5 of 50 Listing Image for 162 Koheo Rd 6 of 50 Listing Image for 162 Koheo Rd 7 of 50 Listing Image for 162 Koheo Rd 8 of 50 Listing Image for 162 Koheo Rd 9 of 50 Listing Image for 162 Koheo Rd 10 of 50 Listing Image for 162 Koheo Rd 11 of 50 Listing Image for 162 Koheo Rd 12 of 50 Listing Image for 162 Koheo Rd 13 of 50 Listing Image for 162 Koheo Rd 14 of 50 Listing Image for 162 Koheo Rd 15 of 50 Listing Image for 162 Koheo Rd 16 of 50 Listing Image for 162 Koheo Rd 17 of 50 Listing Image for 162 Koheo Rd 18 of 50 Listing Image for 162 Koheo Rd 19 of 50 Listing Image for 162 Koheo Rd 20 of 50 Listing Image for 162 Koheo Rd 21 of 50 Listing Image for 162 Koheo Rd 22 of 50 Listing Image for 162 Koheo Rd 23 of 50 Listing Image for 162 Koheo Rd 24 of 50 Listing Image for 162 Koheo Rd 25 of 50 Listing Image for 162 Koheo Rd 26 of 50 Listing Image for 162 Koheo Rd 27 of 50 Listing Image for 162 Koheo Rd 28 of 50 Listing Image for 162 Koheo Rd 29 of 50 Listing Image for 162 Koheo Rd 30 of 50 Listing Image for 162 Koheo Rd 31 of 50 Listing Image for 162 Koheo Rd 32 of 50 Listing Image for 162 Koheo Rd 33 of 50 Listing Image for 162 Koheo Rd 34 of 50 Listing Image for 162 Koheo Rd 35 of 50 Listing Image for 162 Koheo Rd 36 of 50 Listing Image for 162 Koheo Rd 37 of 50 Listing Image for 162 Koheo Rd 38 of 50 Listing Image for 162 Koheo Rd 39 of 50 Listing Image for 162 Koheo Rd 40 of 50 Listing Image for 162 Koheo Rd 41 of 50 Listing Image for 162 Koheo Rd 42 of 50 Listing Image for 162 Koheo Rd 43 of 50 Listing Image for 162 Koheo Rd 44 of 50 Listing Image for 162 Koheo Rd 45 of 50 Listing Image for 162 Koheo Rd 46 of 50 Listing Image for 162 Koheo Rd 47 of 50 Listing Image for 162 Koheo Rd 48 of 50 Listing Image for 162 Koheo Rd 49 of 50 Listing Image for 162 Koheo Rd 50 of 50

$1,825,000

↓ $75,000

Kula/Ulupalakua/Kanaio

162 Koheo Rd, Kula/Ulupalakua/Kanaio

3 Beds 2 Baths 2,172 SqFt Residential MLS® # 409893

Days on Market: 96

ENRG Realty

In Escrow
Listing Image for 80 Nano St 1 of 35 Listing Image for 80 Nano St 2 of 35 Listing Image for 80 Nano St 3 of 35 Listing Image for 80 Nano St 4 of 35 Listing Image for 80 Nano St 5 of 35 Listing Image for 80 Nano St 6 of 35 Listing Image for 80 Nano St 7 of 35 Listing Image for 80 Nano St 8 of 35 Listing Image for 80 Nano St 9 of 35 Listing Image for 80 Nano St 10 of 35 Listing Image for 80 Nano St 11 of 35 Listing Image for 80 Nano St 12 of 35 Listing Image for 80 Nano St 13 of 35 Listing Image for 80 Nano St 14 of 35 Listing Image for 80 Nano St 15 of 35 Listing Image for 80 Nano St 16 of 35 Listing Image for 80 Nano St 17 of 35 Listing Image for 80 Nano St 18 of 35 Listing Image for 80 Nano St 19 of 35 Listing Image for 80 Nano St 20 of 35 Listing Image for 80 Nano St 21 of 35 Listing Image for 80 Nano St 22 of 35 Listing Image for 80 Nano St 23 of 35 Listing Image for 80 Nano St 24 of 35 Listing Image for 80 Nano St 25 of 35 Listing Image for 80 Nano St 26 of 35 Listing Image for 80 Nano St 27 of 35 Listing Image for 80 Nano St 28 of 35 Listing Image for 80 Nano St 29 of 35 Listing Image for 80 Nano St 30 of 35 Listing Image for 80 Nano St 31 of 35 Listing Image for 80 Nano St 32 of 35 Listing Image for 80 Nano St 33 of 35 Listing Image for 80 Nano St 34 of 35 Listing Image for 80 Nano St 35 of 35

$1,750,000

Kahului

80 Nano St, Kahului

7 Beds 5.5 Baths 4,987 SqFt Residential MLS® # 409892

Days on Market: 99

Realty 1st Inc kwee@realty-1st.com

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: 06/17/2026
Listing Image for 145 N Market St 1 of 50 Listing Image for 145 N Market St 2 of 50 Listing Image for 145 N Market St 3 of 50 Listing Image for 145 N Market St 4 of 50 Listing Image for 145 N Market St 5 of 50 Listing Image for 145 N Market St 6 of 50 Listing Image for 145 N Market St 7 of 50 Listing Image for 145 N Market St 8 of 50 Listing Image for 145 N Market St 9 of 50 Listing Image for 145 N Market St 10 of 50 Listing Image for 145 N Market St 11 of 50 Listing Image for 145 N Market St 12 of 50 Listing Image for 145 N Market St 13 of 50 Listing Image for 145 N Market St 14 of 50 Listing Image for 145 N Market St 15 of 50 Listing Image for 145 N Market St 16 of 50 Listing Image for 145 N Market St 17 of 50 Listing Image for 145 N Market St 18 of 50 Listing Image for 145 N Market St 19 of 50 Listing Image for 145 N Market St 20 of 50 Listing Image for 145 N Market St 21 of 50 Listing Image for 145 N Market St 22 of 50 Listing Image for 145 N Market St 23 of 50 Listing Image for 145 N Market St 24 of 50 Listing Image for 145 N Market St 25 of 50 Listing Image for 145 N Market St 26 of 50 Listing Image for 145 N Market St 27 of 50 Listing Image for 145 N Market St 28 of 50 Listing Image for 145 N Market St 29 of 50 Listing Image for 145 N Market St 30 of 50 Listing Image for 145 N Market St 31 of 50 Listing Image for 145 N Market St 32 of 50 Listing Image for 145 N Market St 33 of 50 Listing Image for 145 N Market St 34 of 50 Listing Image for 145 N Market St 35 of 50 Listing Image for 145 N Market St 36 of 50 Listing Image for 145 N Market St 37 of 50 Listing Image for 145 N Market St 38 of 50 Listing Image for 145 N Market St 39 of 50 Listing Image for 145 N Market St 40 of 50 Listing Image for 145 N Market St 41 of 50 Listing Image for 145 N Market St 42 of 50 Listing Image for 145 N Market St 43 of 50 Listing Image for 145 N Market St 44 of 50 Listing Image for 145 N Market St 45 of 50 Listing Image for 145 N Market St 46 of 50 Listing Image for 145 N Market St 47 of 50 Listing Image for 145 N Market St 48 of 50 Listing Image for 145 N Market St 49 of 50 Listing Image for 145 N Market St 50 of 50

$810,000

Wailuku

145 N Market St, Wailuku

0 Beds 0 Baths 0 SqFt Commercial Sale MLS® # 408650 Date Sold: June 17, 2026
Sold
Closed: 09/11/2026
Listing Image for 3150 Wailea Alanui Dr 3507 1 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 2 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 3 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 4 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 5 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 6 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 7 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 8 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 9 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 10 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 11 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 12 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 13 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 14 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 15 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 16 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 17 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 18 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 19 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 20 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 21 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 22 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 23 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 24 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 25 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 26 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 27 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 28 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 29 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 30 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 31 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 32 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 33 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 34 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 35 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 36 of 37 Listing Image for 3150 Wailea Alanui Dr 3507 37 of 37

$1,275,000

↓ $224,000

Wailea Palms 3507

3150 Wailea Alanui Dr 3507, Wailea/Makena

2 Beds 2 Baths 1,194 SqFt Residential MLS® # 408641 Date Sold: September 11, 2026
Sold
Closed: 03/20/2026
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$1,240,000

Parkways

75 Olina St, Kahului

3 Beds 2.5 Baths 1,941 SqFt Residential MLS® # 408627 Date Sold: March 20, 2026
Sold
Closed: 05/22/2026
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$1,720,000

Masters 2902

50 Puu Anoano St 2902, Kaanapali

2 Beds 2 Baths 1,728 SqFt Residential MLS® # 408624 Date Sold: May 22, 2026
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
Sold
Closed: 03/18/2026
Listing Image for 2175 Kauhikoa Rd 1 of 12 Listing Image for 2175 Kauhikoa Rd 2 of 12 Listing Image for 2175 Kauhikoa Rd 3 of 12 Listing Image for 2175 Kauhikoa Rd 4 of 12 Listing Image for 2175 Kauhikoa Rd 5 of 12 Listing Image for 2175 Kauhikoa Rd 6 of 12 Listing Image for 2175 Kauhikoa Rd 7 of 12 Listing Image for 2175 Kauhikoa Rd 8 of 12 Listing Image for 2175 Kauhikoa Rd 9 of 12 Listing Image for 2175 Kauhikoa Rd 10 of 12 Listing Image for 2175 Kauhikoa Rd 11 of 12 Listing Image for 2175 Kauhikoa Rd 12 of 12

$775,000

Haiku

2175 Kauhikoa Rd, Haiku

5 Beds 3 Baths 1,625 SqFt Residential MLS® # 408618 Date Sold: March 18, 2026
Sold
Closed: 07/07/2026
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$820,000

↓ $29,000

Kihei Surfside 109

2936 S Kihei Rd 109, Kihei

1 Bed 1 Bath 504 SqFt Residential MLS® # 408611 Date Sold: July 7, 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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