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 206 Oluea Cir 1 of 50 Listing Image for 206 Oluea Cir 2 of 50 Listing Image for 206 Oluea Cir 3 of 50 Listing Image for 206 Oluea Cir 4 of 50 Listing Image for 206 Oluea Cir 5 of 50 Listing Image for 206 Oluea Cir 6 of 50 Listing Image for 206 Oluea Cir 7 of 50 Listing Image for 206 Oluea Cir 8 of 50 Listing Image for 206 Oluea Cir 9 of 50 Listing Image for 206 Oluea Cir 10 of 50 Listing Image for 206 Oluea Cir 11 of 50 Listing Image for 206 Oluea Cir 12 of 50 Listing Image for 206 Oluea Cir 13 of 50 Listing Image for 206 Oluea Cir 14 of 50 Listing Image for 206 Oluea Cir 15 of 50 Listing Image for 206 Oluea Cir 16 of 50 Listing Image for 206 Oluea Cir 17 of 50 Listing Image for 206 Oluea Cir 18 of 50 Listing Image for 206 Oluea Cir 19 of 50 Listing Image for 206 Oluea Cir 20 of 50 Listing Image for 206 Oluea Cir 21 of 50 Listing Image for 206 Oluea Cir 22 of 50 Listing Image for 206 Oluea Cir 23 of 50 Listing Image for 206 Oluea Cir 24 of 50 Listing Image for 206 Oluea Cir 25 of 50 Listing Image for 206 Oluea Cir 26 of 50 Listing Image for 206 Oluea Cir 27 of 50 Listing Image for 206 Oluea Cir 28 of 50 Listing Image for 206 Oluea Cir 29 of 50 Listing Image for 206 Oluea Cir 30 of 50 Listing Image for 206 Oluea Cir 31 of 50 Listing Image for 206 Oluea Cir 32 of 50 Listing Image for 206 Oluea Cir 33 of 50 Listing Image for 206 Oluea Cir 34 of 50 Listing Image for 206 Oluea Cir 35 of 50 Listing Image for 206 Oluea Cir 36 of 50 Listing Image for 206 Oluea Cir 37 of 50 Listing Image for 206 Oluea Cir 38 of 50 Listing Image for 206 Oluea Cir 39 of 50 Listing Image for 206 Oluea Cir 40 of 50 Listing Image for 206 Oluea Cir 41 of 50 Listing Image for 206 Oluea Cir 42 of 50 Listing Image for 206 Oluea Cir 43 of 50 Listing Image for 206 Oluea Cir 44 of 50 Listing Image for 206 Oluea Cir 45 of 50 Listing Image for 206 Oluea Cir 46 of 50 Listing Image for 206 Oluea Cir 47 of 50 Listing Image for 206 Oluea Cir 48 of 50 Listing Image for 206 Oluea Cir 49 of 50 Listing Image for 206 Oluea Cir 50 of 50

$1,195,000

↓ $5,000

Kamali'i Alayna

206 Oluea Cir, Kihei

4 Beds 3.5 Baths 2,275 SqFt Residential MLS® # 407417

Days on Market: 337

Keller Williams Realty Maui-Ki Cell: 808-859-2086

Listing Image for 350 Kinaole Cir 1 of 50 Listing Image for 350 Kinaole Cir 2 of 50 Listing Image for 350 Kinaole Cir 3 of 50 Listing Image for 350 Kinaole Cir 4 of 50 Listing Image for 350 Kinaole Cir 5 of 50 Listing Image for 350 Kinaole Cir 6 of 50 Listing Image for 350 Kinaole Cir 7 of 50 Listing Image for 350 Kinaole Cir 8 of 50 Listing Image for 350 Kinaole Cir 9 of 50 Listing Image for 350 Kinaole Cir 10 of 50 Listing Image for 350 Kinaole Cir 11 of 50 Listing Image for 350 Kinaole Cir 12 of 50 Listing Image for 350 Kinaole Cir 13 of 50 Listing Image for 350 Kinaole Cir 14 of 50 Listing Image for 350 Kinaole Cir 15 of 50 Listing Image for 350 Kinaole Cir 16 of 50 Listing Image for 350 Kinaole Cir 17 of 50 Listing Image for 350 Kinaole Cir 18 of 50 Listing Image for 350 Kinaole Cir 19 of 50 Listing Image for 350 Kinaole Cir 20 of 50 Listing Image for 350 Kinaole Cir 21 of 50 Listing Image for 350 Kinaole Cir 22 of 50 Listing Image for 350 Kinaole Cir 23 of 50 Listing Image for 350 Kinaole Cir 24 of 50 Listing Image for 350 Kinaole Cir 25 of 50 Listing Image for 350 Kinaole Cir 26 of 50 Listing Image for 350 Kinaole Cir 27 of 50 Listing Image for 350 Kinaole Cir 28 of 50 Listing Image for 350 Kinaole Cir 29 of 50 Listing Image for 350 Kinaole Cir 30 of 50 Listing Image for 350 Kinaole Cir 31 of 50 Listing Image for 350 Kinaole Cir 32 of 50 Listing Image for 350 Kinaole Cir 33 of 50 Listing Image for 350 Kinaole Cir 34 of 50 Listing Image for 350 Kinaole Cir 35 of 50 Listing Image for 350 Kinaole Cir 36 of 50 Listing Image for 350 Kinaole Cir 37 of 50 Listing Image for 350 Kinaole Cir 38 of 50 Listing Image for 350 Kinaole Cir 39 of 50 Listing Image for 350 Kinaole Cir 40 of 50 Listing Image for 350 Kinaole Cir 41 of 50 Listing Image for 350 Kinaole Cir 42 of 50 Listing Image for 350 Kinaole Cir 43 of 50 Listing Image for 350 Kinaole Cir 44 of 50 Listing Image for 350 Kinaole Cir 45 of 50 Listing Image for 350 Kinaole Cir 46 of 50 Listing Image for 350 Kinaole Cir 47 of 50 Listing Image for 350 Kinaole Cir 48 of 50 Listing Image for 350 Kinaole Cir 49 of 50 Listing Image for 350 Kinaole Cir 50 of 50

$1,248,000

↓ $81,000

La Palma Park

350 Kinaole Cir, Kihei

4 Beds 3 Baths 1,687 SqFt Residential MLS® # 407404

Days on Market: 338

Century 21 Island Homes

Listing Image for 171 Halenani Dr 1 of 50 Listing Image for 171 Halenani Dr 2 of 50 Listing Image for 171 Halenani Dr 3 of 50 Listing Image for 171 Halenani Dr 4 of 50 Listing Image for 171 Halenani Dr 5 of 50 Listing Image for 171 Halenani Dr 6 of 50 Listing Image for 171 Halenani Dr 7 of 50 Listing Image for 171 Halenani Dr 8 of 50 Listing Image for 171 Halenani Dr 9 of 50 Listing Image for 171 Halenani Dr 10 of 50 Listing Image for 171 Halenani Dr 11 of 50 Listing Image for 171 Halenani Dr 12 of 50 Listing Image for 171 Halenani Dr 13 of 50 Listing Image for 171 Halenani Dr 14 of 50 Listing Image for 171 Halenani Dr 15 of 50 Listing Image for 171 Halenani Dr 16 of 50 Listing Image for 171 Halenani Dr 17 of 50 Listing Image for 171 Halenani Dr 18 of 50 Listing Image for 171 Halenani Dr 19 of 50 Listing Image for 171 Halenani Dr 20 of 50 Listing Image for 171 Halenani Dr 21 of 50 Listing Image for 171 Halenani Dr 22 of 50 Listing Image for 171 Halenani Dr 23 of 50 Listing Image for 171 Halenani Dr 24 of 50 Listing Image for 171 Halenani Dr 25 of 50 Listing Image for 171 Halenani Dr 26 of 50 Listing Image for 171 Halenani Dr 27 of 50 Listing Image for 171 Halenani Dr 28 of 50 Listing Image for 171 Halenani Dr 29 of 50 Listing Image for 171 Halenani Dr 30 of 50 Listing Image for 171 Halenani Dr 31 of 50 Listing Image for 171 Halenani Dr 32 of 50 Listing Image for 171 Halenani Dr 33 of 50 Listing Image for 171 Halenani Dr 34 of 50 Listing Image for 171 Halenani Dr 35 of 50 Listing Image for 171 Halenani Dr 36 of 50 Listing Image for 171 Halenani Dr 37 of 50 Listing Image for 171 Halenani Dr 38 of 50 Listing Image for 171 Halenani Dr 39 of 50 Listing Image for 171 Halenani Dr 40 of 50 Listing Image for 171 Halenani Dr 41 of 50 Listing Image for 171 Halenani Dr 42 of 50 Listing Image for 171 Halenani Dr 43 of 50 Listing Image for 171 Halenani Dr 44 of 50 Listing Image for 171 Halenani Dr 45 of 50 Listing Image for 171 Halenani Dr 46 of 50 Listing Image for 171 Halenani Dr 47 of 50 Listing Image for 171 Halenani Dr 48 of 50 Listing Image for 171 Halenani Dr 49 of 50 Listing Image for 171 Halenani Dr 50 of 50

$1,370,000

↓ $15,000

Old Sandhills

171 Halenani Dr, Wailuku

3 Beds 2.5 Baths 2,167 SqFt Residential MLS® # 407356

Days on Market: 344

Compass Cell: 808-870-2866

Listing Image for 2452 Kamehameha V Hwy 1 of 32 Listing Image for 2452 Kamehameha V Hwy 2 of 32 Listing Image for 2452 Kamehameha V Hwy 3 of 32 Listing Image for 2452 Kamehameha V Hwy 4 of 32 Listing Image for 2452 Kamehameha V Hwy 5 of 32 Listing Image for 2452 Kamehameha V Hwy 6 of 32 Listing Image for 2452 Kamehameha V Hwy 7 of 32 Listing Image for 2452 Kamehameha V Hwy 8 of 32 Listing Image for 2452 Kamehameha V Hwy 9 of 32 Listing Image for 2452 Kamehameha V Hwy 10 of 32 Listing Image for 2452 Kamehameha V Hwy 11 of 32 Listing Image for 2452 Kamehameha V Hwy 12 of 32 Listing Image for 2452 Kamehameha V Hwy 13 of 32 Listing Image for 2452 Kamehameha V Hwy 14 of 32 Listing Image for 2452 Kamehameha V Hwy 15 of 32 Listing Image for 2452 Kamehameha V Hwy 16 of 32 Listing Image for 2452 Kamehameha V Hwy 17 of 32 Listing Image for 2452 Kamehameha V Hwy 18 of 32 Listing Image for 2452 Kamehameha V Hwy 19 of 32 Listing Image for 2452 Kamehameha V Hwy 20 of 32 Listing Image for 2452 Kamehameha V Hwy 21 of 32 Listing Image for 2452 Kamehameha V Hwy 22 of 32 Listing Image for 2452 Kamehameha V Hwy 23 of 32 Listing Image for 2452 Kamehameha V Hwy 24 of 32 Listing Image for 2452 Kamehameha V Hwy 25 of 32 Listing Image for 2452 Kamehameha V Hwy 26 of 32 Listing Image for 2452 Kamehameha V Hwy 27 of 32 Listing Image for 2452 Kamehameha V Hwy 28 of 32 Listing Image for 2452 Kamehameha V Hwy 29 of 32 Listing Image for 2452 Kamehameha V Hwy 30 of 32 Listing Image for 2452 Kamehameha V Hwy 31 of 32 Listing Image for 2452 Kamehameha V Hwy 32 of 32

$899,000

↓ $26,000

Molokai

2452 Kamehameha V Hwy, Molokai

4 Beds 2 Baths 2,040 SqFt Residential MLS® # 407351

Days on Market: 344

Molokai Vacation Properties Cell: 808-658-1717

Listing Image for 139 Kai La Pl 35b 1 of 34 Listing Image for 139 Kai La Pl 35b 2 of 34 Listing Image for 139 Kai La Pl 35b 3 of 34 Listing Image for 139 Kai La Pl 35b 4 of 34 Listing Image for 139 Kai La Pl 35b 5 of 34 Listing Image for 139 Kai La Pl 35b 6 of 34 Listing Image for 139 Kai La Pl 35b 7 of 34 Listing Image for 139 Kai La Pl 35b 8 of 34 Listing Image for 139 Kai La Pl 35b 9 of 34 Listing Image for 139 Kai La Pl 35b 10 of 34 Listing Image for 139 Kai La Pl 35b 11 of 34 Listing Image for 139 Kai La Pl 35b 12 of 34 Listing Image for 139 Kai La Pl 35b 13 of 34 Listing Image for 139 Kai La Pl 35b 14 of 34 Listing Image for 139 Kai La Pl 35b 15 of 34 Listing Image for 139 Kai La Pl 35b 16 of 34 Listing Image for 139 Kai La Pl 35b 17 of 34 Listing Image for 139 Kai La Pl 35b 18 of 34 Listing Image for 139 Kai La Pl 35b 19 of 34 Listing Image for 139 Kai La Pl 35b 20 of 34 Listing Image for 139 Kai La Pl 35b 21 of 34 Listing Image for 139 Kai La Pl 35b 22 of 34 Listing Image for 139 Kai La Pl 35b 23 of 34 Listing Image for 139 Kai La Pl 35b 24 of 34 Listing Image for 139 Kai La Pl 35b 25 of 34 Listing Image for 139 Kai La Pl 35b 26 of 34 Listing Image for 139 Kai La Pl 35b 27 of 34 Listing Image for 139 Kai La Pl 35b 28 of 34 Listing Image for 139 Kai La Pl 35b 29 of 34 Listing Image for 139 Kai La Pl 35b 30 of 34 Listing Image for 139 Kai La Pl 35b 31 of 34 Listing Image for 139 Kai La Pl 35b 32 of 34 Listing Image for 139 Kai La Pl 35b 33 of 34 Listing Image for 139 Kai La Pl 35b 34 of 34

$1,885,000

↓ $210,000

Kai Malu 35B

139 Kai La Pl 35b, Wailea/Makena

3 Beds 2.5 Baths 1,796 SqFt Residential MLS® # 407317

Days on Market: 349

Hawaii Life (W) Cell: 808-283-6791

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

$3,890,000

Kaanapali

250 Akia Pl, Kaanapali

6 Beds 4.5 Baths 4,086 SqFt Residential MLS® # 407287

Days on Market: 351

Coldwell Banker Island Prop-KP Cell: 808-344-2677

Listing Image for 3291 Waileia Pl 1 of 44 Listing Image for 3291 Waileia Pl 2 of 44 Listing Image for 3291 Waileia Pl 3 of 44 Listing Image for 3291 Waileia Pl 4 of 44 Listing Image for 3291 Waileia Pl 5 of 44 Listing Image for 3291 Waileia Pl 6 of 44 Listing Image for 3291 Waileia Pl 7 of 44 Listing Image for 3291 Waileia Pl 8 of 44 Listing Image for 3291 Waileia Pl 9 of 44 Listing Image for 3291 Waileia Pl 10 of 44 Listing Image for 3291 Waileia Pl 11 of 44 Listing Image for 3291 Waileia Pl 12 of 44 Listing Image for 3291 Waileia Pl 13 of 44 Listing Image for 3291 Waileia Pl 14 of 44 Listing Image for 3291 Waileia Pl 15 of 44 Listing Image for 3291 Waileia Pl 16 of 44 Listing Image for 3291 Waileia Pl 17 of 44 Listing Image for 3291 Waileia Pl 18 of 44 Listing Image for 3291 Waileia Pl 19 of 44 Listing Image for 3291 Waileia Pl 20 of 44 Listing Image for 3291 Waileia Pl 21 of 44 Listing Image for 3291 Waileia Pl 22 of 44 Listing Image for 3291 Waileia Pl 23 of 44 Listing Image for 3291 Waileia Pl 24 of 44 Listing Image for 3291 Waileia Pl 25 of 44 Listing Image for 3291 Waileia Pl 26 of 44 Listing Image for 3291 Waileia Pl 27 of 44 Listing Image for 3291 Waileia Pl 28 of 44 Listing Image for 3291 Waileia Pl 29 of 44 Listing Image for 3291 Waileia Pl 30 of 44 Listing Image for 3291 Waileia Pl 31 of 44 Listing Image for 3291 Waileia Pl 32 of 44 Listing Image for 3291 Waileia Pl 33 of 44 Listing Image for 3291 Waileia Pl 34 of 44 Listing Image for 3291 Waileia Pl 35 of 44 Listing Image for 3291 Waileia Pl 36 of 44 Listing Image for 3291 Waileia Pl 37 of 44 Listing Image for 3291 Waileia Pl 38 of 44 Listing Image for 3291 Waileia Pl 39 of 44 Listing Image for 3291 Waileia Pl 40 of 44 Listing Image for 3291 Waileia Pl 41 of 44 Listing Image for 3291 Waileia Pl 42 of 44 Listing Image for 3291 Waileia Pl 43 of 44 Listing Image for 3291 Waileia Pl 44 of 44

$2,549,000

↓ $146,000

Maui Meadows

3291 Waileia Pl, Maui Meadows

3 Beds 3 Baths 3,028 SqFt Residential MLS® # 407284

Days on Market: 351

Berkshire Hathaway Maui Prop-L

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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: 03/31/2026
Listing Image for 47 Nano St 1 of 2 Listing Image for 47 Nano St 2 of 2

$1,200,000

↓ $98,000

Kahului

47 Nano St, Kahului

8 Beds 4 Baths 2,979 SqFt Residential MLS® # 407182 Date Sold: March 31, 2026
Sold
Closed: 10/13/2025
Listing Image for 85 Pukolu Way 1 of 50 Listing Image for 85 Pukolu Way 2 of 50 Listing Image for 85 Pukolu Way 3 of 50 Listing Image for 85 Pukolu Way 4 of 50 Listing Image for 85 Pukolu Way 5 of 50 Listing Image for 85 Pukolu Way 6 of 50 Listing Image for 85 Pukolu Way 7 of 50 Listing Image for 85 Pukolu Way 8 of 50 Listing Image for 85 Pukolu Way 9 of 50 Listing Image for 85 Pukolu Way 10 of 50 Listing Image for 85 Pukolu Way 11 of 50 Listing Image for 85 Pukolu Way 12 of 50 Listing Image for 85 Pukolu Way 13 of 50 Listing Image for 85 Pukolu Way 14 of 50 Listing Image for 85 Pukolu Way 15 of 50 Listing Image for 85 Pukolu Way 16 of 50 Listing Image for 85 Pukolu Way 17 of 50 Listing Image for 85 Pukolu Way 18 of 50 Listing Image for 85 Pukolu Way 19 of 50 Listing Image for 85 Pukolu Way 20 of 50 Listing Image for 85 Pukolu Way 21 of 50 Listing Image for 85 Pukolu Way 22 of 50 Listing Image for 85 Pukolu Way 23 of 50 Listing Image for 85 Pukolu Way 24 of 50 Listing Image for 85 Pukolu Way 25 of 50 Listing Image for 85 Pukolu Way 26 of 50 Listing Image for 85 Pukolu Way 27 of 50 Listing Image for 85 Pukolu Way 28 of 50 Listing Image for 85 Pukolu Way 29 of 50 Listing Image for 85 Pukolu Way 30 of 50 Listing Image for 85 Pukolu Way 31 of 50 Listing Image for 85 Pukolu Way 32 of 50 Listing Image for 85 Pukolu Way 33 of 50 Listing Image for 85 Pukolu Way 34 of 50 Listing Image for 85 Pukolu Way 35 of 50 Listing Image for 85 Pukolu Way 36 of 50 Listing Image for 85 Pukolu Way 37 of 50 Listing Image for 85 Pukolu Way 38 of 50 Listing Image for 85 Pukolu Way 39 of 50 Listing Image for 85 Pukolu Way 40 of 50 Listing Image for 85 Pukolu Way 41 of 50 Listing Image for 85 Pukolu Way 42 of 50 Listing Image for 85 Pukolu Way 43 of 50 Listing Image for 85 Pukolu Way 44 of 50 Listing Image for 85 Pukolu Way 45 of 50 Listing Image for 85 Pukolu Way 46 of 50 Listing Image for 85 Pukolu Way 47 of 50 Listing Image for 85 Pukolu Way 48 of 50 Listing Image for 85 Pukolu Way 49 of 50 Listing Image for 85 Pukolu Way 50 of 50

$3,075,000

Wailea Kai

85 Pukolu Way, Wailea/Makena

5 Beds 3.5 Baths 4,232 SqFt Residential MLS® # 407080 Date Sold: October 13, 2025
Sold
Closed: 10/31/2025
Listing Image for 3200 Wailea Alanui Dr 207 1 of 36 Listing Image for 3200 Wailea Alanui Dr 207 2 of 36 Listing Image for 3200 Wailea Alanui Dr 207 3 of 36 Listing Image for 3200 Wailea Alanui Dr 207 4 of 36 Listing Image for 3200 Wailea Alanui Dr 207 5 of 36 Listing Image for 3200 Wailea Alanui Dr 207 6 of 36 Listing Image for 3200 Wailea Alanui Dr 207 7 of 36 Listing Image for 3200 Wailea Alanui Dr 207 8 of 36 Listing Image for 3200 Wailea Alanui Dr 207 9 of 36 Listing Image for 3200 Wailea Alanui Dr 207 10 of 36 Listing Image for 3200 Wailea Alanui Dr 207 11 of 36 Listing Image for 3200 Wailea Alanui Dr 207 12 of 36 Listing Image for 3200 Wailea Alanui Dr 207 13 of 36 Listing Image for 3200 Wailea Alanui Dr 207 14 of 36 Listing Image for 3200 Wailea Alanui Dr 207 15 of 36 Listing Image for 3200 Wailea Alanui Dr 207 16 of 36 Listing Image for 3200 Wailea Alanui Dr 207 17 of 36 Listing Image for 3200 Wailea Alanui Dr 207 18 of 36 Listing Image for 3200 Wailea Alanui Dr 207 19 of 36 Listing Image for 3200 Wailea Alanui Dr 207 20 of 36 Listing Image for 3200 Wailea Alanui Dr 207 21 of 36 Listing Image for 3200 Wailea Alanui Dr 207 22 of 36 Listing Image for 3200 Wailea Alanui Dr 207 23 of 36 Listing Image for 3200 Wailea Alanui Dr 207 24 of 36 Listing Image for 3200 Wailea Alanui Dr 207 25 of 36 Listing Image for 3200 Wailea Alanui Dr 207 26 of 36 Listing Image for 3200 Wailea Alanui Dr 207 27 of 36 Listing Image for 3200 Wailea Alanui Dr 207 28 of 36 Listing Image for 3200 Wailea Alanui Dr 207 29 of 36 Listing Image for 3200 Wailea Alanui Dr 207 30 of 36 Listing Image for 3200 Wailea Alanui Dr 207 31 of 36 Listing Image for 3200 Wailea Alanui Dr 207 32 of 36 Listing Image for 3200 Wailea Alanui Dr 207 33 of 36 Listing Image for 3200 Wailea Alanui Dr 207 34 of 36 Listing Image for 3200 Wailea Alanui Dr 207 35 of 36 Listing Image for 3200 Wailea Alanui Dr 207 36 of 36

$999,000

Palms at Wailea 207

3200 Wailea Alanui Dr 207, Wailea/Makena

1 Bed 2 Baths 1,022 SqFt Residential MLS® # 407069 Date Sold: October 31, 2025
Sold
Closed: 05/11/2026
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$1,200,000

Wailuku

1886 Loke St, Wailuku

5 Beds 1 Bath 4,973 SqFt Residential Income MLS® # 406977 Date Sold: May 11, 2026
Sold
Closed: 11/07/2025
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$915,000

Aina Olu Terrace

3576 Pahala St, Makawao/Olinda/Haliimaile

3 Beds 1 Bath 1,300 SqFt Residential MLS® # 407005 Date Sold: November 7, 2025
Sold
Closed: 08/06/2026
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$920,000

↓ $255,000

Pukalani

129 Kumano Dr, Pukalani

3 Beds 1 Bath 904 SqFt Residential MLS® # 407006 Date Sold: August 6, 2026
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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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