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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Short Term Rental
Listing Image for 130 Kai Malina Pkwy Nr312 1 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 2 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 3 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 4 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 5 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 6 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 7 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 8 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 9 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 10 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 11 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 12 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 13 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 14 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 15 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 16 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 17 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 18 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 19 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 20 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 21 of 22 Listing Image for 130 Kai Malina Pkwy Nr312 22 of 22

$1,499,000

↓ $51,000

Honua Kai - Konea NR312

130 Kai Malina Pkwy Nr312, Kaanapali

2 Beds 1 Bath 915 SqFt Residential MLS® # 404231

Days on Market: 652

Maui Westside Properties

Listing Image for 40685 Hana Hwy 1 of 35 Listing Image for 40685 Hana Hwy 2 of 35 Listing Image for 40685 Hana Hwy 3 of 35 Listing Image for 40685 Hana Hwy 4 of 35 Listing Image for 40685 Hana Hwy 5 of 35 Listing Image for 40685 Hana Hwy 6 of 35 Listing Image for 40685 Hana Hwy 7 of 35 Listing Image for 40685 Hana Hwy 8 of 35 Listing Image for 40685 Hana Hwy 9 of 35 Listing Image for 40685 Hana Hwy 10 of 35 Listing Image for 40685 Hana Hwy 11 of 35 Listing Image for 40685 Hana Hwy 12 of 35 Listing Image for 40685 Hana Hwy 13 of 35 Listing Image for 40685 Hana Hwy 14 of 35 Listing Image for 40685 Hana Hwy 15 of 35 Listing Image for 40685 Hana Hwy 16 of 35 Listing Image for 40685 Hana Hwy 17 of 35 Listing Image for 40685 Hana Hwy 18 of 35 Listing Image for 40685 Hana Hwy 19 of 35 Listing Image for 40685 Hana Hwy 20 of 35 Listing Image for 40685 Hana Hwy 21 of 35 Listing Image for 40685 Hana Hwy 22 of 35 Listing Image for 40685 Hana Hwy 23 of 35 Listing Image for 40685 Hana Hwy 24 of 35 Listing Image for 40685 Hana Hwy 25 of 35 Listing Image for 40685 Hana Hwy 26 of 35 Listing Image for 40685 Hana Hwy 27 of 35 Listing Image for 40685 Hana Hwy 28 of 35 Listing Image for 40685 Hana Hwy 29 of 35 Listing Image for 40685 Hana Hwy 30 of 35 Listing Image for 40685 Hana Hwy 31 of 35 Listing Image for 40685 Hana Hwy 32 of 35 Listing Image for 40685 Hana Hwy 33 of 35 Listing Image for 40685 Hana Hwy 34 of 35 Listing Image for 40685 Hana Hwy 35 of 35

$2,100,000

↓ $295,000

Hana

40685 Hana Hwy, Hana

3 Beds 2 Baths 2,012 SqFt Residential MLS® # 405873

Days on Market: 499

Island Sotheby's International Realty(W) Cell: 808-446-5198

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

$1,525,000

↓ $124,000

Wailea Ekolu 1008

10 Wailea Ekolu Pl 1008, Wailea/Makena

2 Beds 2 Baths 1,071 SqFt Residential MLS® # 405937

Days on Market: 493

Coldwell Banker Island Prop(S) Cell: 808-989-2215

Short Term Rental
Listing Image for 4909 Lower Honoapiilani Rd D3 1 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 2 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 3 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 4 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 5 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 6 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 7 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 8 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 9 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 10 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 11 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 12 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 13 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 14 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 15 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 16 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 17 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 18 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 19 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 20 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 21 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 22 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 23 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 24 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 25 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 26 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 27 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 28 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 29 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 30 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 31 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 32 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 33 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 34 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 35 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 36 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 37 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 38 of 39 Listing Image for 4909 Lower Honoapiilani Rd D3 39 of 39

$850,000

↓ $50,000

Kahana Sunset D3

4909 Lower Honoapiilani Rd D3, Napili/Kahana/Honokowai

2 Beds 2.5 Baths 1,050 SqFt Residential MLS® # 399736

Days on Market: 1104

Hawaiian Islands Mgmt LLC

Short Term Rental
Listing Image for 110 Kaanapali Shores Pl 501 1 of 48 Listing Image for 110 Kaanapali Shores Pl 501 2 of 48 Listing Image for 110 Kaanapali Shores Pl 501 3 of 48 Listing Image for 110 Kaanapali Shores Pl 501 4 of 48 Listing Image for 110 Kaanapali Shores Pl 501 5 of 48 Listing Image for 110 Kaanapali Shores Pl 501 6 of 48 Listing Image for 110 Kaanapali Shores Pl 501 7 of 48 Listing Image for 110 Kaanapali Shores Pl 501 8 of 48 Listing Image for 110 Kaanapali Shores Pl 501 9 of 48 Listing Image for 110 Kaanapali Shores Pl 501 10 of 48 Listing Image for 110 Kaanapali Shores Pl 501 11 of 48 Listing Image for 110 Kaanapali Shores Pl 501 12 of 48 Listing Image for 110 Kaanapali Shores Pl 501 13 of 48 Listing Image for 110 Kaanapali Shores Pl 501 14 of 48 Listing Image for 110 Kaanapali Shores Pl 501 15 of 48 Listing Image for 110 Kaanapali Shores Pl 501 16 of 48 Listing Image for 110 Kaanapali Shores Pl 501 17 of 48 Listing Image for 110 Kaanapali Shores Pl 501 18 of 48 Listing Image for 110 Kaanapali Shores Pl 501 19 of 48 Listing Image for 110 Kaanapali Shores Pl 501 20 of 48 Listing Image for 110 Kaanapali Shores Pl 501 21 of 48 Listing Image for 110 Kaanapali Shores Pl 501 22 of 48 Listing Image for 110 Kaanapali Shores Pl 501 23 of 48 Listing Image for 110 Kaanapali Shores Pl 501 24 of 48 Listing Image for 110 Kaanapali Shores Pl 501 25 of 48 Listing Image for 110 Kaanapali Shores Pl 501 26 of 48 Listing Image for 110 Kaanapali Shores Pl 501 27 of 48 Listing Image for 110 Kaanapali Shores Pl 501 28 of 48 Listing Image for 110 Kaanapali Shores Pl 501 29 of 48 Listing Image for 110 Kaanapali Shores Pl 501 30 of 48 Listing Image for 110 Kaanapali Shores Pl 501 31 of 48 Listing Image for 110 Kaanapali Shores Pl 501 32 of 48 Listing Image for 110 Kaanapali Shores Pl 501 33 of 48 Listing Image for 110 Kaanapali Shores Pl 501 34 of 48 Listing Image for 110 Kaanapali Shores Pl 501 35 of 48 Listing Image for 110 Kaanapali Shores Pl 501 36 of 48 Listing Image for 110 Kaanapali Shores Pl 501 37 of 48 Listing Image for 110 Kaanapali Shores Pl 501 38 of 48 Listing Image for 110 Kaanapali Shores Pl 501 39 of 48 Listing Image for 110 Kaanapali Shores Pl 501 40 of 48 Listing Image for 110 Kaanapali Shores Pl 501 41 of 48 Listing Image for 110 Kaanapali Shores Pl 501 42 of 48 Listing Image for 110 Kaanapali Shores Pl 501 43 of 48 Listing Image for 110 Kaanapali Shores Pl 501 44 of 48 Listing Image for 110 Kaanapali Shores Pl 501 45 of 48 Listing Image for 110 Kaanapali Shores Pl 501 46 of 48 Listing Image for 110 Kaanapali Shores Pl 501 47 of 48 Listing Image for 110 Kaanapali Shores Pl 501 48 of 48

$2,250,000

↓ $50,000

Mahana 501

110 Kaanapali Shores Pl 501, Kaanapali

2 Beds 2 Baths 1,178 SqFt Residential MLS® # 405779

Days on Market: 507

Maui Paradise Properties LLC 808-661-1535

Short Term Rental
Listing Image for 2481 Kaanapali Pkwy 415 1 of 24 Listing Image for 2481 Kaanapali Pkwy 415 2 of 24 Listing Image for 2481 Kaanapali Pkwy 415 3 of 24 Listing Image for 2481 Kaanapali Pkwy 415 4 of 24 Listing Image for 2481 Kaanapali Pkwy 415 5 of 24 Listing Image for 2481 Kaanapali Pkwy 415 6 of 24 Listing Image for 2481 Kaanapali Pkwy 415 7 of 24 Listing Image for 2481 Kaanapali Pkwy 415 8 of 24 Listing Image for 2481 Kaanapali Pkwy 415 9 of 24 Listing Image for 2481 Kaanapali Pkwy 415 10 of 24 Listing Image for 2481 Kaanapali Pkwy 415 11 of 24 Listing Image for 2481 Kaanapali Pkwy 415 12 of 24 Listing Image for 2481 Kaanapali Pkwy 415 13 of 24 Listing Image for 2481 Kaanapali Pkwy 415 14 of 24 Listing Image for 2481 Kaanapali Pkwy 415 15 of 24 Listing Image for 2481 Kaanapali Pkwy 415 16 of 24 Listing Image for 2481 Kaanapali Pkwy 415 17 of 24 Listing Image for 2481 Kaanapali Pkwy 415 18 of 24 Listing Image for 2481 Kaanapali Pkwy 415 19 of 24 Listing Image for 2481 Kaanapali Pkwy 415 20 of 24 Listing Image for 2481 Kaanapali Pkwy 415 21 of 24 Listing Image for 2481 Kaanapali Pkwy 415 22 of 24 Listing Image for 2481 Kaanapali Pkwy 415 23 of 24 Listing Image for 2481 Kaanapali Pkwy 415 24 of 24

$999,000

↓ $96,000

Whaler 415

2481 Kaanapali Pkwy 415, Kaanapali

0 Beds 1 Bath 523 SqFt Residential MLS® # 405710

Days on Market: 528

Berkshire Hathaway Maui Prop-L

Short Term Rental
Listing Image for 2777 S Kihei Rd I219 1 of 39 Listing Image for 2777 S Kihei Rd I219 2 of 39 Listing Image for 2777 S Kihei Rd I219 3 of 39 Listing Image for 2777 S Kihei Rd I219 4 of 39 Listing Image for 2777 S Kihei Rd I219 5 of 39 Listing Image for 2777 S Kihei Rd I219 6 of 39 Listing Image for 2777 S Kihei Rd I219 7 of 39 Listing Image for 2777 S Kihei Rd I219 8 of 39 Listing Image for 2777 S Kihei Rd I219 9 of 39 Listing Image for 2777 S Kihei Rd I219 10 of 39 Listing Image for 2777 S Kihei Rd I219 11 of 39 Listing Image for 2777 S Kihei Rd I219 12 of 39 Listing Image for 2777 S Kihei Rd I219 13 of 39 Listing Image for 2777 S Kihei Rd I219 14 of 39 Listing Image for 2777 S Kihei Rd I219 15 of 39 Listing Image for 2777 S Kihei Rd I219 16 of 39 Listing Image for 2777 S Kihei Rd I219 17 of 39 Listing Image for 2777 S Kihei Rd I219 18 of 39 Listing Image for 2777 S Kihei Rd I219 19 of 39 Listing Image for 2777 S Kihei Rd I219 20 of 39 Listing Image for 2777 S Kihei Rd I219 21 of 39 Listing Image for 2777 S Kihei Rd I219 22 of 39 Listing Image for 2777 S Kihei Rd I219 23 of 39 Listing Image for 2777 S Kihei Rd I219 24 of 39 Listing Image for 2777 S Kihei Rd I219 25 of 39 Listing Image for 2777 S Kihei Rd I219 26 of 39 Listing Image for 2777 S Kihei Rd I219 27 of 39 Listing Image for 2777 S Kihei Rd I219 28 of 39 Listing Image for 2777 S Kihei Rd I219 29 of 39 Listing Image for 2777 S Kihei Rd I219 30 of 39 Listing Image for 2777 S Kihei Rd I219 31 of 39 Listing Image for 2777 S Kihei Rd I219 32 of 39 Listing Image for 2777 S Kihei Rd I219 33 of 39 Listing Image for 2777 S Kihei Rd I219 34 of 39 Listing Image for 2777 S Kihei Rd I219 35 of 39 Listing Image for 2777 S Kihei Rd I219 36 of 39 Listing Image for 2777 S Kihei Rd I219 37 of 39 Listing Image for 2777 S Kihei Rd I219 38 of 39 Listing Image for 2777 S Kihei Rd I219 39 of 39

$1,149,000

↓ $150,000

Maui Kamaole i219

2777 S Kihei Rd I219, Kihei

2 Beds 2 Baths 1,052 SqFt Residential MLS® # 405529

Days on Market: 528

Hawaii Life (W) Cell: 808-264-4123

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: 08/14/2025
137 Oliona St 134, Makawao/Olinda/Haliimaile

$1,325,000

Hokuula

137 Oliona St 134, Makawao/Olinda/Haliimaile

4 Beds 2.5 Baths 2,280 SqFt Residential MLS® # 406841 Date Sold: August 14, 2025
Sold
Closed: 11/05/2025
Listing Image for 109 Kulolio St 1 of 46 Listing Image for 109 Kulolio St 2 of 46 Listing Image for 109 Kulolio St 3 of 46 Listing Image for 109 Kulolio St 4 of 46 Listing Image for 109 Kulolio St 5 of 46 Listing Image for 109 Kulolio St 6 of 46 Listing Image for 109 Kulolio St 7 of 46 Listing Image for 109 Kulolio St 8 of 46 Listing Image for 109 Kulolio St 9 of 46 Listing Image for 109 Kulolio St 10 of 46 Listing Image for 109 Kulolio St 11 of 46 Listing Image for 109 Kulolio St 12 of 46 Listing Image for 109 Kulolio St 13 of 46 Listing Image for 109 Kulolio St 14 of 46 Listing Image for 109 Kulolio St 15 of 46 Listing Image for 109 Kulolio St 16 of 46 Listing Image for 109 Kulolio St 17 of 46 Listing Image for 109 Kulolio St 18 of 46 Listing Image for 109 Kulolio St 19 of 46 Listing Image for 109 Kulolio St 20 of 46 Listing Image for 109 Kulolio St 21 of 46 Listing Image for 109 Kulolio St 22 of 46 Listing Image for 109 Kulolio St 23 of 46 Listing Image for 109 Kulolio St 24 of 46 Listing Image for 109 Kulolio St 25 of 46 Listing Image for 109 Kulolio St 26 of 46 Listing Image for 109 Kulolio St 27 of 46 Listing Image for 109 Kulolio St 28 of 46 Listing Image for 109 Kulolio St 29 of 46 Listing Image for 109 Kulolio St 30 of 46 Listing Image for 109 Kulolio St 31 of 46 Listing Image for 109 Kulolio St 32 of 46 Listing Image for 109 Kulolio St 33 of 46 Listing Image for 109 Kulolio St 34 of 46 Listing Image for 109 Kulolio St 35 of 46 Listing Image for 109 Kulolio St 36 of 46 Listing Image for 109 Kulolio St 37 of 46 Listing Image for 109 Kulolio St 38 of 46 Listing Image for 109 Kulolio St 39 of 46 Listing Image for 109 Kulolio St 40 of 46 Listing Image for 109 Kulolio St 41 of 46 Listing Image for 109 Kulolio St 42 of 46 Listing Image for 109 Kulolio St 43 of 46 Listing Image for 109 Kulolio St 44 of 46 Listing Image for 109 Kulolio St 45 of 46 Listing Image for 109 Kulolio St 46 of 46

$1,250,000

Pauwela Homes

109 Kulolio St, Haiku

3 Beds 2 Baths 1,132 SqFt Residential MLS® # 406861 Date Sold: November 5, 2025
Sold
Closed: 06/01/2026
Listing Image for 150 Puukolii Rd 41 1 of 34 Listing Image for 150 Puukolii Rd 41 2 of 34 Listing Image for 150 Puukolii Rd 41 3 of 34 Listing Image for 150 Puukolii Rd 41 4 of 34 Listing Image for 150 Puukolii Rd 41 5 of 34 Listing Image for 150 Puukolii Rd 41 6 of 34 Listing Image for 150 Puukolii Rd 41 7 of 34 Listing Image for 150 Puukolii Rd 41 8 of 34 Listing Image for 150 Puukolii Rd 41 9 of 34 Listing Image for 150 Puukolii Rd 41 10 of 34 Listing Image for 150 Puukolii Rd 41 11 of 34 Listing Image for 150 Puukolii Rd 41 12 of 34 Listing Image for 150 Puukolii Rd 41 13 of 34 Listing Image for 150 Puukolii Rd 41 14 of 34 Listing Image for 150 Puukolii Rd 41 15 of 34 Listing Image for 150 Puukolii Rd 41 16 of 34 Listing Image for 150 Puukolii Rd 41 17 of 34 Listing Image for 150 Puukolii Rd 41 18 of 34 Listing Image for 150 Puukolii Rd 41 19 of 34 Listing Image for 150 Puukolii Rd 41 20 of 34 Listing Image for 150 Puukolii Rd 41 21 of 34 Listing Image for 150 Puukolii Rd 41 22 of 34 Listing Image for 150 Puukolii Rd 41 23 of 34 Listing Image for 150 Puukolii Rd 41 24 of 34 Listing Image for 150 Puukolii Rd 41 25 of 34 Listing Image for 150 Puukolii Rd 41 26 of 34 Listing Image for 150 Puukolii Rd 41 27 of 34 Listing Image for 150 Puukolii Rd 41 28 of 34 Listing Image for 150 Puukolii Rd 41 29 of 34 Listing Image for 150 Puukolii Rd 41 30 of 34 Listing Image for 150 Puukolii Rd 41 31 of 34 Listing Image for 150 Puukolii Rd 41 32 of 34 Listing Image for 150 Puukolii Rd 41 33 of 34 Listing Image for 150 Puukolii Rd 41 34 of 34

$1,065,000

↓ $80,000

Kaanapali Plantation 41

150 Puukolii Rd 41, Kaanapali

3 Beds 2.5 Baths 1,545 SqFt Residential MLS® # 406829 Date Sold: June 1, 2026
Sold
Closed: 10/10/2025
Listing Image for 44 Kanani Rd 3-205 1 of 41 Listing Image for 44 Kanani Rd 3-205 2 of 41 Listing Image for 44 Kanani Rd 3-205 3 of 41 Listing Image for 44 Kanani Rd 3-205 4 of 41 Listing Image for 44 Kanani Rd 3-205 5 of 41 Listing Image for 44 Kanani Rd 3-205 6 of 41 Listing Image for 44 Kanani Rd 3-205 7 of 41 Listing Image for 44 Kanani Rd 3-205 8 of 41 Listing Image for 44 Kanani Rd 3-205 9 of 41 Listing Image for 44 Kanani Rd 3-205 10 of 41 Listing Image for 44 Kanani Rd 3-205 11 of 41 Listing Image for 44 Kanani Rd 3-205 12 of 41 Listing Image for 44 Kanani Rd 3-205 13 of 41 Listing Image for 44 Kanani Rd 3-205 14 of 41 Listing Image for 44 Kanani Rd 3-205 15 of 41 Listing Image for 44 Kanani Rd 3-205 16 of 41 Listing Image for 44 Kanani Rd 3-205 17 of 41 Listing Image for 44 Kanani Rd 3-205 18 of 41 Listing Image for 44 Kanani Rd 3-205 19 of 41 Listing Image for 44 Kanani Rd 3-205 20 of 41 Listing Image for 44 Kanani Rd 3-205 21 of 41 Listing Image for 44 Kanani Rd 3-205 22 of 41 Listing Image for 44 Kanani Rd 3-205 23 of 41 Listing Image for 44 Kanani Rd 3-205 24 of 41 Listing Image for 44 Kanani Rd 3-205 25 of 41 Listing Image for 44 Kanani Rd 3-205 26 of 41 Listing Image for 44 Kanani Rd 3-205 27 of 41 Listing Image for 44 Kanani Rd 3-205 28 of 41 Listing Image for 44 Kanani Rd 3-205 29 of 41 Listing Image for 44 Kanani Rd 3-205 30 of 41 Listing Image for 44 Kanani Rd 3-205 31 of 41 Listing Image for 44 Kanani Rd 3-205 32 of 41 Listing Image for 44 Kanani Rd 3-205 33 of 41 Listing Image for 44 Kanani Rd 3-205 34 of 41 Listing Image for 44 Kanani Rd 3-205 35 of 41 Listing Image for 44 Kanani Rd 3-205 36 of 41 Listing Image for 44 Kanani Rd 3-205 37 of 41 Listing Image for 44 Kanani Rd 3-205 38 of 41 Listing Image for 44 Kanani Rd 3-205 39 of 41 Listing Image for 44 Kanani Rd 3-205 40 of 41 Listing Image for 44 Kanani Rd 3-205 41 of 41

$765,000

↓ $59,000

Hale Kanani 3-205

44 Kanani Rd 3-205, Kihei

2 Beds 2 Baths 890 SqFt Residential MLS® # 406844 Date Sold: October 10, 2025
Buying Real Estate on Maui

Buying Real Estate on Maui

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Sold
Closed: 10/21/2025
Listing Image for 323 W Kuiaha Rd 1 of 30 Listing Image for 323 W Kuiaha Rd 2 of 30 Listing Image for 323 W Kuiaha Rd 3 of 30 Listing Image for 323 W Kuiaha Rd 4 of 30 Listing Image for 323 W Kuiaha Rd 5 of 30 Listing Image for 323 W Kuiaha Rd 6 of 30 Listing Image for 323 W Kuiaha Rd 7 of 30 Listing Image for 323 W Kuiaha Rd 8 of 30 Listing Image for 323 W Kuiaha Rd 9 of 30 Listing Image for 323 W Kuiaha Rd 10 of 30 Listing Image for 323 W Kuiaha Rd 11 of 30 Listing Image for 323 W Kuiaha Rd 12 of 30 Listing Image for 323 W Kuiaha Rd 13 of 30 Listing Image for 323 W Kuiaha Rd 14 of 30 Listing Image for 323 W Kuiaha Rd 15 of 30 Listing Image for 323 W Kuiaha Rd 16 of 30 Listing Image for 323 W Kuiaha Rd 17 of 30 Listing Image for 323 W Kuiaha Rd 18 of 30 Listing Image for 323 W Kuiaha Rd 19 of 30 Listing Image for 323 W Kuiaha Rd 20 of 30 Listing Image for 323 W Kuiaha Rd 21 of 30 Listing Image for 323 W Kuiaha Rd 22 of 30 Listing Image for 323 W Kuiaha Rd 23 of 30 Listing Image for 323 W Kuiaha Rd 24 of 30 Listing Image for 323 W Kuiaha Rd 25 of 30 Listing Image for 323 W Kuiaha Rd 26 of 30 Listing Image for 323 W Kuiaha Rd 27 of 30 Listing Image for 323 W Kuiaha Rd 28 of 30 Listing Image for 323 W Kuiaha Rd 29 of 30 Listing Image for 323 W Kuiaha Rd 30 of 30

$1,075,000

Haiku

323 W Kuiaha Rd, Haiku

2 Beds 2 Baths 1,166 SqFt Residential MLS® # 406837 Date Sold: October 21, 2025
Sold
Closed: 01/27/2026
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$1,475,000

↓ $220,000

Kihei

2635 Lioholo Pl, Kihei

4 Beds 4 Baths 2,464 SqFt Residential MLS® # 406862 Date Sold: January 27, 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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