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 3300 Wailea Alanui Dr 10f 1 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 2 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 3 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 4 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 5 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 6 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 7 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 8 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 9 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 10 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 11 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 12 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 13 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 14 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 15 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 16 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 17 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 18 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 19 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 20 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 21 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 22 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 23 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 24 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 25 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 26 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 27 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 28 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 29 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 30 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 31 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 32 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 33 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 34 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 35 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 36 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 37 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 38 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 39 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 40 of 41 Listing Image for 3300 Wailea Alanui Dr 10f 41 of 41

$1,095,000

Wailea Ekahi 10F

3300 Wailea Alanui Dr 10f, Wailea/Makena

1 Bed 1 Bath 792 SqFt Residential MLS® # 410522

Days on Market: 30

Coldwell Banker Island Prop-Ku Cell: 808-250-6754

In Escrow
Listing Image for 4030 Lower Kula Rd 1 of 40 Listing Image for 4030 Lower Kula Rd 2 of 40 Listing Image for 4030 Lower Kula Rd 3 of 40 Listing Image for 4030 Lower Kula Rd 4 of 40 Listing Image for 4030 Lower Kula Rd 5 of 40 Listing Image for 4030 Lower Kula Rd 6 of 40 Listing Image for 4030 Lower Kula Rd 7 of 40 Listing Image for 4030 Lower Kula Rd 8 of 40 Listing Image for 4030 Lower Kula Rd 9 of 40 Listing Image for 4030 Lower Kula Rd 10 of 40 Listing Image for 4030 Lower Kula Rd 11 of 40 Listing Image for 4030 Lower Kula Rd 12 of 40 Listing Image for 4030 Lower Kula Rd 13 of 40 Listing Image for 4030 Lower Kula Rd 14 of 40 Listing Image for 4030 Lower Kula Rd 15 of 40 Listing Image for 4030 Lower Kula Rd 16 of 40 Listing Image for 4030 Lower Kula Rd 17 of 40 Listing Image for 4030 Lower Kula Rd 18 of 40 Listing Image for 4030 Lower Kula Rd 19 of 40 Listing Image for 4030 Lower Kula Rd 20 of 40 Listing Image for 4030 Lower Kula Rd 21 of 40 Listing Image for 4030 Lower Kula Rd 22 of 40 Listing Image for 4030 Lower Kula Rd 23 of 40 Listing Image for 4030 Lower Kula Rd 24 of 40 Listing Image for 4030 Lower Kula Rd 25 of 40 Listing Image for 4030 Lower Kula Rd 26 of 40 Listing Image for 4030 Lower Kula Rd 27 of 40 Listing Image for 4030 Lower Kula Rd 28 of 40 Listing Image for 4030 Lower Kula Rd 29 of 40 Listing Image for 4030 Lower Kula Rd 30 of 40 Listing Image for 4030 Lower Kula Rd 31 of 40 Listing Image for 4030 Lower Kula Rd 32 of 40 Listing Image for 4030 Lower Kula Rd 33 of 40 Listing Image for 4030 Lower Kula Rd 34 of 40 Listing Image for 4030 Lower Kula Rd 35 of 40 Listing Image for 4030 Lower Kula Rd 36 of 40 Listing Image for 4030 Lower Kula Rd 37 of 40 Listing Image for 4030 Lower Kula Rd 38 of 40 Listing Image for 4030 Lower Kula Rd 39 of 40 Listing Image for 4030 Lower Kula Rd 40 of 40

$1,290,000

Kula/Ulupalakua/Kanaio

4030 Lower Kula Rd, Kula/Ulupalakua/Kanaio

3 Beds 2 Baths 889 SqFt Residential MLS® # 410519

Days on Market: 30

eXp Realty Cell: 808-707-0504

Listing Image for 101 Elepaio Pl A 1 of 43 Listing Image for 101 Elepaio Pl A 2 of 43 Listing Image for 101 Elepaio Pl A 3 of 43 Listing Image for 101 Elepaio Pl A 4 of 43 Listing Image for 101 Elepaio Pl A 5 of 43 Listing Image for 101 Elepaio Pl A 6 of 43 Listing Image for 101 Elepaio Pl A 7 of 43 Listing Image for 101 Elepaio Pl A 8 of 43 Listing Image for 101 Elepaio Pl A 9 of 43 Listing Image for 101 Elepaio Pl A 10 of 43 Listing Image for 101 Elepaio Pl A 11 of 43 Listing Image for 101 Elepaio Pl A 12 of 43 Listing Image for 101 Elepaio Pl A 13 of 43 Listing Image for 101 Elepaio Pl A 14 of 43 Listing Image for 101 Elepaio Pl A 15 of 43 Listing Image for 101 Elepaio Pl A 16 of 43 Listing Image for 101 Elepaio Pl A 17 of 43 Listing Image for 101 Elepaio Pl A 18 of 43 Listing Image for 101 Elepaio Pl A 19 of 43 Listing Image for 101 Elepaio Pl A 20 of 43 Listing Image for 101 Elepaio Pl A 21 of 43 Listing Image for 101 Elepaio Pl A 22 of 43 Listing Image for 101 Elepaio Pl A 23 of 43 Listing Image for 101 Elepaio Pl A 24 of 43 Listing Image for 101 Elepaio Pl A 25 of 43 Listing Image for 101 Elepaio Pl A 26 of 43 Listing Image for 101 Elepaio Pl A 27 of 43 Listing Image for 101 Elepaio Pl A 28 of 43 Listing Image for 101 Elepaio Pl A 29 of 43 Listing Image for 101 Elepaio Pl A 30 of 43 Listing Image for 101 Elepaio Pl A 31 of 43 Listing Image for 101 Elepaio Pl A 32 of 43 Listing Image for 101 Elepaio Pl A 33 of 43 Listing Image for 101 Elepaio Pl A 34 of 43 Listing Image for 101 Elepaio Pl A 35 of 43 Listing Image for 101 Elepaio Pl A 36 of 43 Listing Image for 101 Elepaio Pl A 37 of 43 Listing Image for 101 Elepaio Pl A 38 of 43 Listing Image for 101 Elepaio Pl A 39 of 43 Listing Image for 101 Elepaio Pl A 40 of 43 Listing Image for 101 Elepaio Pl A 41 of 43 Listing Image for 101 Elepaio Pl A 42 of 43 Listing Image for 101 Elepaio Pl A 43 of 43

$1,999,000

↓ $100,900

Ainakula

101 Elepaio Pl A, Kula/Ulupalakua/Kanaio

5 Beds 3 Baths 3,104 SqFt Residential MLS® # 410515

Days on Market: 31

Equity One Real Estate Inc (M) Cell: 808-283-9918

Listing Image for 250 Heaaula Pl 1 of 50 Listing Image for 250 Heaaula Pl 2 of 50 Listing Image for 250 Heaaula Pl 3 of 50 Listing Image for 250 Heaaula Pl 4 of 50 Listing Image for 250 Heaaula Pl 5 of 50 Listing Image for 250 Heaaula Pl 6 of 50 Listing Image for 250 Heaaula Pl 7 of 50 Listing Image for 250 Heaaula Pl 8 of 50 Listing Image for 250 Heaaula Pl 9 of 50 Listing Image for 250 Heaaula Pl 10 of 50 Listing Image for 250 Heaaula Pl 11 of 50 Listing Image for 250 Heaaula Pl 12 of 50 Listing Image for 250 Heaaula Pl 13 of 50 Listing Image for 250 Heaaula Pl 14 of 50 Listing Image for 250 Heaaula Pl 15 of 50 Listing Image for 250 Heaaula Pl 16 of 50 Listing Image for 250 Heaaula Pl 17 of 50 Listing Image for 250 Heaaula Pl 18 of 50 Listing Image for 250 Heaaula Pl 19 of 50 Listing Image for 250 Heaaula Pl 20 of 50 Listing Image for 250 Heaaula Pl 21 of 50 Listing Image for 250 Heaaula Pl 22 of 50 Listing Image for 250 Heaaula Pl 23 of 50 Listing Image for 250 Heaaula Pl 24 of 50 Listing Image for 250 Heaaula Pl 25 of 50 Listing Image for 250 Heaaula Pl 26 of 50 Listing Image for 250 Heaaula Pl 27 of 50 Listing Image for 250 Heaaula Pl 28 of 50 Listing Image for 250 Heaaula Pl 29 of 50 Listing Image for 250 Heaaula Pl 30 of 50 Listing Image for 250 Heaaula Pl 31 of 50 Listing Image for 250 Heaaula Pl 32 of 50 Listing Image for 250 Heaaula Pl 33 of 50 Listing Image for 250 Heaaula Pl 34 of 50 Listing Image for 250 Heaaula Pl 35 of 50 Listing Image for 250 Heaaula Pl 36 of 50 Listing Image for 250 Heaaula Pl 37 of 50 Listing Image for 250 Heaaula Pl 38 of 50 Listing Image for 250 Heaaula Pl 39 of 50 Listing Image for 250 Heaaula Pl 40 of 50 Listing Image for 250 Heaaula Pl 41 of 50 Listing Image for 250 Heaaula Pl 42 of 50 Listing Image for 250 Heaaula Pl 43 of 50 Listing Image for 250 Heaaula Pl 44 of 50 Listing Image for 250 Heaaula Pl 45 of 50 Listing Image for 250 Heaaula Pl 46 of 50 Listing Image for 250 Heaaula Pl 47 of 50 Listing Image for 250 Heaaula Pl 48 of 50 Listing Image for 250 Heaaula Pl 49 of 50 Listing Image for 250 Heaaula Pl 50 of 50

$1,580,000

↓ $120,000

Peahi

250 Heaaula Pl, Haiku

2 Beds 2 Baths 1,314 SqFt Residential MLS® # 410513

Days on Market: 32

Commercial Prop of Maui LLC

Buying Real Estate on Maui

Buying Real Estate on Maui

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

Read the Guide
Listing Image for 2165 Iliili Rd 1 of 50 Listing Image for 2165 Iliili Rd 2 of 50 Listing Image for 2165 Iliili Rd 3 of 50 Listing Image for 2165 Iliili Rd 4 of 50 Listing Image for 2165 Iliili Rd 5 of 50 Listing Image for 2165 Iliili Rd 6 of 50 Listing Image for 2165 Iliili Rd 7 of 50 Listing Image for 2165 Iliili Rd 8 of 50 Listing Image for 2165 Iliili Rd 9 of 50 Listing Image for 2165 Iliili Rd 10 of 50 Listing Image for 2165 Iliili Rd 11 of 50 Listing Image for 2165 Iliili Rd 12 of 50 Listing Image for 2165 Iliili Rd 13 of 50 Listing Image for 2165 Iliili Rd 14 of 50 Listing Image for 2165 Iliili Rd 15 of 50 Listing Image for 2165 Iliili Rd 16 of 50 Listing Image for 2165 Iliili Rd 17 of 50 Listing Image for 2165 Iliili Rd 18 of 50 Listing Image for 2165 Iliili Rd 19 of 50 Listing Image for 2165 Iliili Rd 20 of 50 Listing Image for 2165 Iliili Rd 21 of 50 Listing Image for 2165 Iliili Rd 22 of 50 Listing Image for 2165 Iliili Rd 23 of 50 Listing Image for 2165 Iliili Rd 24 of 50 Listing Image for 2165 Iliili Rd 25 of 50 Listing Image for 2165 Iliili Rd 26 of 50 Listing Image for 2165 Iliili Rd 27 of 50 Listing Image for 2165 Iliili Rd 28 of 50 Listing Image for 2165 Iliili Rd 29 of 50 Listing Image for 2165 Iliili Rd 30 of 50 Listing Image for 2165 Iliili Rd 31 of 50 Listing Image for 2165 Iliili Rd 32 of 50 Listing Image for 2165 Iliili Rd 33 of 50 Listing Image for 2165 Iliili Rd 34 of 50 Listing Image for 2165 Iliili Rd 35 of 50 Listing Image for 2165 Iliili Rd 36 of 50 Listing Image for 2165 Iliili Rd 37 of 50 Listing Image for 2165 Iliili Rd 38 of 50 Listing Image for 2165 Iliili Rd 39 of 50 Listing Image for 2165 Iliili Rd 40 of 50 Listing Image for 2165 Iliili Rd 41 of 50 Listing Image for 2165 Iliili Rd 42 of 50 Listing Image for 2165 Iliili Rd 43 of 50 Listing Image for 2165 Iliili Rd 44 of 50 Listing Image for 2165 Iliili Rd 45 of 50 Listing Image for 2165 Iliili Rd 46 of 50 Listing Image for 2165 Iliili Rd 47 of 50 Listing Image for 2165 Iliili Rd 48 of 50 Listing Image for 2165 Iliili Rd 49 of 50 Listing Image for 2165 Iliili Rd 50 of 50

$3,250,000

Kihei

2165 Iliili Rd, Kihei

3 Beds 2 Baths 1,460 SqFt Residential MLS® # 410512

Days on Market: 31

Coldwell Banker Island Prop(S) Cell: 808-344-0180

In Escrow
Listing Image for 160 Kualapa Pl 60 1 of 49 Listing Image for 160 Kualapa Pl 60 2 of 49 Listing Image for 160 Kualapa Pl 60 3 of 49 Listing Image for 160 Kualapa Pl 60 4 of 49 Listing Image for 160 Kualapa Pl 60 5 of 49 Listing Image for 160 Kualapa Pl 60 6 of 49 Listing Image for 160 Kualapa Pl 60 7 of 49 Listing Image for 160 Kualapa Pl 60 8 of 49 Listing Image for 160 Kualapa Pl 60 9 of 49 Listing Image for 160 Kualapa Pl 60 10 of 49 Listing Image for 160 Kualapa Pl 60 11 of 49 Listing Image for 160 Kualapa Pl 60 12 of 49 Listing Image for 160 Kualapa Pl 60 13 of 49 Listing Image for 160 Kualapa Pl 60 14 of 49 Listing Image for 160 Kualapa Pl 60 15 of 49 Listing Image for 160 Kualapa Pl 60 16 of 49 Listing Image for 160 Kualapa Pl 60 17 of 49 Listing Image for 160 Kualapa Pl 60 18 of 49 Listing Image for 160 Kualapa Pl 60 19 of 49 Listing Image for 160 Kualapa Pl 60 20 of 49 Listing Image for 160 Kualapa Pl 60 21 of 49 Listing Image for 160 Kualapa Pl 60 22 of 49 Listing Image for 160 Kualapa Pl 60 23 of 49 Listing Image for 160 Kualapa Pl 60 24 of 49 Listing Image for 160 Kualapa Pl 60 25 of 49 Listing Image for 160 Kualapa Pl 60 26 of 49 Listing Image for 160 Kualapa Pl 60 27 of 49 Listing Image for 160 Kualapa Pl 60 28 of 49 Listing Image for 160 Kualapa Pl 60 29 of 49 Listing Image for 160 Kualapa Pl 60 30 of 49 Listing Image for 160 Kualapa Pl 60 31 of 49 Listing Image for 160 Kualapa Pl 60 32 of 49 Listing Image for 160 Kualapa Pl 60 33 of 49 Listing Image for 160 Kualapa Pl 60 34 of 49 Listing Image for 160 Kualapa Pl 60 35 of 49 Listing Image for 160 Kualapa Pl 60 36 of 49 Listing Image for 160 Kualapa Pl 60 37 of 49 Listing Image for 160 Kualapa Pl 60 38 of 49 Listing Image for 160 Kualapa Pl 60 39 of 49 Listing Image for 160 Kualapa Pl 60 40 of 49 Listing Image for 160 Kualapa Pl 60 41 of 49 Listing Image for 160 Kualapa Pl 60 42 of 49 Listing Image for 160 Kualapa Pl 60 43 of 49 Listing Image for 160 Kualapa Pl 60 44 of 49 Listing Image for 160 Kualapa Pl 60 45 of 49 Listing Image for 160 Kualapa Pl 60 46 of 49 Listing Image for 160 Kualapa Pl 60 47 of 49 Listing Image for 160 Kualapa Pl 60 48 of 49 Listing Image for 160 Kualapa Pl 60 49 of 49

$2,150,000

Vintage at Kaanapali 60

160 Kualapa Pl 60, Kaanapali

3 Beds 2.5 Baths 2,200 SqFt Residential MLS® # 410509

Days on Market: 31

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

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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: 09/04/2026
Listing Image for 41 Iliwai Loop 1 of 48 Listing Image for 41 Iliwai Loop 2 of 48 Listing Image for 41 Iliwai Loop 3 of 48 Listing Image for 41 Iliwai Loop 4 of 48 Listing Image for 41 Iliwai Loop 5 of 48 Listing Image for 41 Iliwai Loop 6 of 48 Listing Image for 41 Iliwai Loop 7 of 48 Listing Image for 41 Iliwai Loop 8 of 48 Listing Image for 41 Iliwai Loop 9 of 48 Listing Image for 41 Iliwai Loop 10 of 48 Listing Image for 41 Iliwai Loop 11 of 48 Listing Image for 41 Iliwai Loop 12 of 48 Listing Image for 41 Iliwai Loop 13 of 48 Listing Image for 41 Iliwai Loop 14 of 48 Listing Image for 41 Iliwai Loop 15 of 48 Listing Image for 41 Iliwai Loop 16 of 48 Listing Image for 41 Iliwai Loop 17 of 48 Listing Image for 41 Iliwai Loop 18 of 48 Listing Image for 41 Iliwai Loop 19 of 48 Listing Image for 41 Iliwai Loop 20 of 48 Listing Image for 41 Iliwai Loop 21 of 48 Listing Image for 41 Iliwai Loop 22 of 48 Listing Image for 41 Iliwai Loop 23 of 48 Listing Image for 41 Iliwai Loop 24 of 48 Listing Image for 41 Iliwai Loop 25 of 48 Listing Image for 41 Iliwai Loop 26 of 48 Listing Image for 41 Iliwai Loop 27 of 48 Listing Image for 41 Iliwai Loop 28 of 48 Listing Image for 41 Iliwai Loop 29 of 48 Listing Image for 41 Iliwai Loop 30 of 48 Listing Image for 41 Iliwai Loop 31 of 48 Listing Image for 41 Iliwai Loop 32 of 48 Listing Image for 41 Iliwai Loop 33 of 48 Listing Image for 41 Iliwai Loop 34 of 48 Listing Image for 41 Iliwai Loop 35 of 48 Listing Image for 41 Iliwai Loop 36 of 48 Listing Image for 41 Iliwai Loop 37 of 48 Listing Image for 41 Iliwai Loop 38 of 48 Listing Image for 41 Iliwai Loop 39 of 48 Listing Image for 41 Iliwai Loop 40 of 48 Listing Image for 41 Iliwai Loop 41 of 48 Listing Image for 41 Iliwai Loop 42 of 48 Listing Image for 41 Iliwai Loop 43 of 48 Listing Image for 41 Iliwai Loop 44 of 48 Listing Image for 41 Iliwai Loop 45 of 48 Listing Image for 41 Iliwai Loop 46 of 48 Listing Image for 41 Iliwai Loop 47 of 48 Listing Image for 41 Iliwai Loop 48 of 48

$1,710,000

↓ $115,000

Keonekai Heights

41 Iliwai Loop, Kihei

4 Beds 3 Baths 2,011 SqFt Residential MLS® # 409616 Date Sold: September 4, 2026
Sold
Closed: 06/15/2026
Listing Image for 87 Hoolaau St 12 1 of 42 Listing Image for 87 Hoolaau St 12 2 of 42 Listing Image for 87 Hoolaau St 12 3 of 42 Listing Image for 87 Hoolaau St 12 4 of 42 Listing Image for 87 Hoolaau St 12 5 of 42 Listing Image for 87 Hoolaau St 12 6 of 42 Listing Image for 87 Hoolaau St 12 7 of 42 Listing Image for 87 Hoolaau St 12 8 of 42 Listing Image for 87 Hoolaau St 12 9 of 42 Listing Image for 87 Hoolaau St 12 10 of 42 Listing Image for 87 Hoolaau St 12 11 of 42 Listing Image for 87 Hoolaau St 12 12 of 42 Listing Image for 87 Hoolaau St 12 13 of 42 Listing Image for 87 Hoolaau St 12 14 of 42 Listing Image for 87 Hoolaau St 12 15 of 42 Listing Image for 87 Hoolaau St 12 16 of 42 Listing Image for 87 Hoolaau St 12 17 of 42 Listing Image for 87 Hoolaau St 12 18 of 42 Listing Image for 87 Hoolaau St 12 19 of 42 Listing Image for 87 Hoolaau St 12 20 of 42 Listing Image for 87 Hoolaau St 12 21 of 42 Listing Image for 87 Hoolaau St 12 22 of 42 Listing Image for 87 Hoolaau St 12 23 of 42 Listing Image for 87 Hoolaau St 12 24 of 42 Listing Image for 87 Hoolaau St 12 25 of 42 Listing Image for 87 Hoolaau St 12 26 of 42 Listing Image for 87 Hoolaau St 12 27 of 42 Listing Image for 87 Hoolaau St 12 28 of 42 Listing Image for 87 Hoolaau St 12 29 of 42 Listing Image for 87 Hoolaau St 12 30 of 42 Listing Image for 87 Hoolaau St 12 31 of 42 Listing Image for 87 Hoolaau St 12 32 of 42 Listing Image for 87 Hoolaau St 12 33 of 42 Listing Image for 87 Hoolaau St 12 34 of 42 Listing Image for 87 Hoolaau St 12 35 of 42 Listing Image for 87 Hoolaau St 12 36 of 42 Listing Image for 87 Hoolaau St 12 37 of 42 Listing Image for 87 Hoolaau St 12 38 of 42 Listing Image for 87 Hoolaau St 12 39 of 42 Listing Image for 87 Hoolaau St 12 40 of 42 Listing Image for 87 Hoolaau St 12 41 of 42 Listing Image for 87 Hoolaau St 12 42 of 42

$929,000

Kamani at Kehalani 12

87 Hoolaau St 12, Wailuku

3 Beds 2.5 Baths 1,457 SqFt Residential MLS® # 409607 Date Sold: June 15, 2026
Sold
Closed: 08/18/2026
Listing Image for 1367 S Kihei Rd 3-106 1 of 47 Listing Image for 1367 S Kihei Rd 3-106 2 of 47 Listing Image for 1367 S Kihei Rd 3-106 3 of 47 Listing Image for 1367 S Kihei Rd 3-106 4 of 47 Listing Image for 1367 S Kihei Rd 3-106 5 of 47 Listing Image for 1367 S Kihei Rd 3-106 6 of 47 Listing Image for 1367 S Kihei Rd 3-106 7 of 47 Listing Image for 1367 S Kihei Rd 3-106 8 of 47 Listing Image for 1367 S Kihei Rd 3-106 9 of 47 Listing Image for 1367 S Kihei Rd 3-106 10 of 47 Listing Image for 1367 S Kihei Rd 3-106 11 of 47 Listing Image for 1367 S Kihei Rd 3-106 12 of 47 Listing Image for 1367 S Kihei Rd 3-106 13 of 47 Listing Image for 1367 S Kihei Rd 3-106 14 of 47 Listing Image for 1367 S Kihei Rd 3-106 15 of 47 Listing Image for 1367 S Kihei Rd 3-106 16 of 47 Listing Image for 1367 S Kihei Rd 3-106 17 of 47 Listing Image for 1367 S Kihei Rd 3-106 18 of 47 Listing Image for 1367 S Kihei Rd 3-106 19 of 47 Listing Image for 1367 S Kihei Rd 3-106 20 of 47 Listing Image for 1367 S Kihei Rd 3-106 21 of 47 Listing Image for 1367 S Kihei Rd 3-106 22 of 47 Listing Image for 1367 S Kihei Rd 3-106 23 of 47 Listing Image for 1367 S Kihei Rd 3-106 24 of 47 Listing Image for 1367 S Kihei Rd 3-106 25 of 47 Listing Image for 1367 S Kihei Rd 3-106 26 of 47 Listing Image for 1367 S Kihei Rd 3-106 27 of 47 Listing Image for 1367 S Kihei Rd 3-106 28 of 47 Listing Image for 1367 S Kihei Rd 3-106 29 of 47 Listing Image for 1367 S Kihei Rd 3-106 30 of 47 Listing Image for 1367 S Kihei Rd 3-106 31 of 47 Listing Image for 1367 S Kihei Rd 3-106 32 of 47 Listing Image for 1367 S Kihei Rd 3-106 33 of 47 Listing Image for 1367 S Kihei Rd 3-106 34 of 47 Listing Image for 1367 S Kihei Rd 3-106 35 of 47 Listing Image for 1367 S Kihei Rd 3-106 36 of 47 Listing Image for 1367 S Kihei Rd 3-106 37 of 47 Listing Image for 1367 S Kihei Rd 3-106 38 of 47 Listing Image for 1367 S Kihei Rd 3-106 39 of 47 Listing Image for 1367 S Kihei Rd 3-106 40 of 47 Listing Image for 1367 S Kihei Rd 3-106 41 of 47 Listing Image for 1367 S Kihei Rd 3-106 42 of 47 Listing Image for 1367 S Kihei Rd 3-106 43 of 47 Listing Image for 1367 S Kihei Rd 3-106 44 of 47 Listing Image for 1367 S Kihei Rd 3-106 45 of 47 Listing Image for 1367 S Kihei Rd 3-106 46 of 47 Listing Image for 1367 S Kihei Rd 3-106 47 of 47

$1,199,000

Kai Ani Village 3-106

1367 S Kihei Rd 3-106, Kihei

2 Beds 2.5 Baths 1,901 SqFt Residential MLS® # 409606 Date Sold: August 18, 2026
Sold
Closed: 06/12/2026
Listing Image for 0 Anuhea Pl 1 of 26 Listing Image for 0 Anuhea Pl 2 of 26 Listing Image for 0 Anuhea Pl 3 of 26 Listing Image for 0 Anuhea Pl 4 of 26 Listing Image for 0 Anuhea Pl 5 of 26 Listing Image for 0 Anuhea Pl 6 of 26 Listing Image for 0 Anuhea Pl 7 of 26 Listing Image for 0 Anuhea Pl 8 of 26 Listing Image for 0 Anuhea Pl 9 of 26 Listing Image for 0 Anuhea Pl 10 of 26 Listing Image for 0 Anuhea Pl 11 of 26 Listing Image for 0 Anuhea Pl 12 of 26 Listing Image for 0 Anuhea Pl 13 of 26 Listing Image for 0 Anuhea Pl 14 of 26 Listing Image for 0 Anuhea Pl 15 of 26 Listing Image for 0 Anuhea Pl 16 of 26 Listing Image for 0 Anuhea Pl 17 of 26 Listing Image for 0 Anuhea Pl 18 of 26 Listing Image for 0 Anuhea Pl 19 of 26 Listing Image for 0 Anuhea Pl 20 of 26 Listing Image for 0 Anuhea Pl 21 of 26 Listing Image for 0 Anuhea Pl 22 of 26 Listing Image for 0 Anuhea Pl 23 of 26 Listing Image for 0 Anuhea Pl 24 of 26 Listing Image for 0 Anuhea Pl 25 of 26 Listing Image for 0 Anuhea Pl 26 of 26

$1,650,000

Kula/Ulupalakua/Kanaio

0 Anuhea Pl, Kula/Ulupalakua/Kanaio

0 Beds 0 Baths 0 SqFt Land MLS® # 409589 Date Sold: June 12, 2026
Sold
Closed: 06/18/2026
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$2,895,000

Kula/Ulupalakua/Kanaio

1304 Naalae Rd, Kula/Ulupalakua/Kanaio

4 Beds 2 Baths 3,361 SqFt Residential MLS® # 409587 Date Sold: June 18, 2026
Sold
Closed: 09/09/2026
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$1,490,000

Spreckelsville/Paia/Kuau

168 Hana Hwy, Spreckelsville/Paia/Kuau

3 Beds 1.5 Baths 1,008 SqFt Residential MLS® # 409583 Date Sold: September 9, 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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