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 5295 Lower Honoapiilani Rd C35 1 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 2 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 3 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 4 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 5 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 6 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 7 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 8 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 9 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 10 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 11 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 12 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 13 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 14 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 15 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 16 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 17 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 18 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 19 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 20 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 21 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 22 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 23 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 24 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 25 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 26 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 27 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 28 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 29 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 30 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 31 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 32 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 33 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 34 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 35 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 36 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 37 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 38 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 39 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 40 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 41 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 42 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 43 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 44 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 45 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 46 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 47 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 48 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 49 of 50 Listing Image for 5295 Lower Honoapiilani Rd C35 50 of 50

$1,495,000

↓ $105,000

Napili Point C35

5295 Lower Honoapiilani Rd C35, Napili/Kahana/Honokowai

2 Beds 2 Baths 955 SqFt Residential MLS® # 409824

Days on Market: 103

Hawaii Life (L) Cell: 808-280-1390

In Escrow
Listing Image for 337 Aalii Way 1 of 50 Listing Image for 337 Aalii Way 2 of 50 Listing Image for 337 Aalii Way 3 of 50 Listing Image for 337 Aalii Way 4 of 50 Listing Image for 337 Aalii Way 5 of 50 Listing Image for 337 Aalii Way 6 of 50 Listing Image for 337 Aalii Way 7 of 50 Listing Image for 337 Aalii Way 8 of 50 Listing Image for 337 Aalii Way 9 of 50 Listing Image for 337 Aalii Way 10 of 50 Listing Image for 337 Aalii Way 11 of 50 Listing Image for 337 Aalii Way 12 of 50 Listing Image for 337 Aalii Way 13 of 50 Listing Image for 337 Aalii Way 14 of 50 Listing Image for 337 Aalii Way 15 of 50 Listing Image for 337 Aalii Way 16 of 50 Listing Image for 337 Aalii Way 17 of 50 Listing Image for 337 Aalii Way 18 of 50 Listing Image for 337 Aalii Way 19 of 50 Listing Image for 337 Aalii Way 20 of 50 Listing Image for 337 Aalii Way 21 of 50 Listing Image for 337 Aalii Way 22 of 50 Listing Image for 337 Aalii Way 23 of 50 Listing Image for 337 Aalii Way 24 of 50 Listing Image for 337 Aalii Way 25 of 50 Listing Image for 337 Aalii Way 26 of 50 Listing Image for 337 Aalii Way 27 of 50 Listing Image for 337 Aalii Way 28 of 50 Listing Image for 337 Aalii Way 29 of 50 Listing Image for 337 Aalii Way 30 of 50 Listing Image for 337 Aalii Way 31 of 50 Listing Image for 337 Aalii Way 32 of 50 Listing Image for 337 Aalii Way 33 of 50 Listing Image for 337 Aalii Way 34 of 50 Listing Image for 337 Aalii Way 35 of 50 Listing Image for 337 Aalii Way 36 of 50 Listing Image for 337 Aalii Way 37 of 50 Listing Image for 337 Aalii Way 38 of 50 Listing Image for 337 Aalii Way 39 of 50 Listing Image for 337 Aalii Way 40 of 50 Listing Image for 337 Aalii Way 41 of 50 Listing Image for 337 Aalii Way 42 of 50 Listing Image for 337 Aalii Way 43 of 50 Listing Image for 337 Aalii Way 44 of 50 Listing Image for 337 Aalii Way 45 of 50 Listing Image for 337 Aalii Way 46 of 50 Listing Image for 337 Aalii Way 47 of 50 Listing Image for 337 Aalii Way 48 of 50 Listing Image for 337 Aalii Way 49 of 50 Listing Image for 337 Aalii Way 50 of 50

$2,499,000

↑ $104,000

Kaanapali Golf Estates

337 Aalii Way, Kaanapali

3 Beds 3.5 Baths 2,819 SqFt Residential MLS® # 409822

Days on Market: 106

Berkshire Hathaway Maui Prop-L Cell: 808-280-7061

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

$1,995,000

Puamana 24-4

24 Puamelia Pl 24-4, Lahaina

3 Beds 4 Baths 1,488 SqFt Residential MLS® # 409821

Days on Market: 103

Hawaii Life (L) Cell: 808-280-1390

Listing Image for 549 Honoapiilani Hwy 1 of 36 Listing Image for 549 Honoapiilani Hwy 2 of 36 Listing Image for 549 Honoapiilani Hwy 3 of 36 Listing Image for 549 Honoapiilani Hwy 4 of 36 Listing Image for 549 Honoapiilani Hwy 5 of 36 Listing Image for 549 Honoapiilani Hwy 6 of 36 Listing Image for 549 Honoapiilani Hwy 7 of 36 Listing Image for 549 Honoapiilani Hwy 8 of 36 Listing Image for 549 Honoapiilani Hwy 9 of 36 Listing Image for 549 Honoapiilani Hwy 10 of 36 Listing Image for 549 Honoapiilani Hwy 11 of 36 Listing Image for 549 Honoapiilani Hwy 12 of 36 Listing Image for 549 Honoapiilani Hwy 13 of 36 Listing Image for 549 Honoapiilani Hwy 14 of 36 Listing Image for 549 Honoapiilani Hwy 15 of 36 Listing Image for 549 Honoapiilani Hwy 16 of 36 Listing Image for 549 Honoapiilani Hwy 17 of 36 Listing Image for 549 Honoapiilani Hwy 18 of 36 Listing Image for 549 Honoapiilani Hwy 19 of 36 Listing Image for 549 Honoapiilani Hwy 20 of 36 Listing Image for 549 Honoapiilani Hwy 21 of 36 Listing Image for 549 Honoapiilani Hwy 22 of 36 Listing Image for 549 Honoapiilani Hwy 23 of 36 Listing Image for 549 Honoapiilani Hwy 24 of 36 Listing Image for 549 Honoapiilani Hwy 25 of 36 Listing Image for 549 Honoapiilani Hwy 26 of 36 Listing Image for 549 Honoapiilani Hwy 27 of 36 Listing Image for 549 Honoapiilani Hwy 28 of 36 Listing Image for 549 Honoapiilani Hwy 29 of 36 Listing Image for 549 Honoapiilani Hwy 30 of 36 Listing Image for 549 Honoapiilani Hwy 31 of 36 Listing Image for 549 Honoapiilani Hwy 32 of 36 Listing Image for 549 Honoapiilani Hwy 33 of 36 Listing Image for 549 Honoapiilani Hwy 34 of 36 Listing Image for 549 Honoapiilani Hwy 35 of 36 Listing Image for 549 Honoapiilani Hwy 36 of 36

$1,100,000

↓ $100,000

Wailuku

549 Honoapiilani Hwy, Wailuku

2 Beds 1.5 Baths 1,487 SqFt Residential MLS® # 409817

Days on Market: 103

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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 125 Pualu Loop 1 of 38 Listing Image for 125 Pualu Loop 2 of 38 Listing Image for 125 Pualu Loop 3 of 38 Listing Image for 125 Pualu Loop 4 of 38 Listing Image for 125 Pualu Loop 5 of 38 Listing Image for 125 Pualu Loop 6 of 38 Listing Image for 125 Pualu Loop 7 of 38 Listing Image for 125 Pualu Loop 8 of 38 Listing Image for 125 Pualu Loop 9 of 38 Listing Image for 125 Pualu Loop 10 of 38 Listing Image for 125 Pualu Loop 11 of 38 Listing Image for 125 Pualu Loop 12 of 38 Listing Image for 125 Pualu Loop 13 of 38 Listing Image for 125 Pualu Loop 14 of 38 Listing Image for 125 Pualu Loop 15 of 38 Listing Image for 125 Pualu Loop 16 of 38 Listing Image for 125 Pualu Loop 17 of 38 Listing Image for 125 Pualu Loop 18 of 38 Listing Image for 125 Pualu Loop 19 of 38 Listing Image for 125 Pualu Loop 20 of 38 Listing Image for 125 Pualu Loop 21 of 38 Listing Image for 125 Pualu Loop 22 of 38 Listing Image for 125 Pualu Loop 23 of 38 Listing Image for 125 Pualu Loop 24 of 38 Listing Image for 125 Pualu Loop 25 of 38 Listing Image for 125 Pualu Loop 26 of 38 Listing Image for 125 Pualu Loop 27 of 38 Listing Image for 125 Pualu Loop 28 of 38 Listing Image for 125 Pualu Loop 29 of 38 Listing Image for 125 Pualu Loop 30 of 38 Listing Image for 125 Pualu Loop 31 of 38 Listing Image for 125 Pualu Loop 32 of 38 Listing Image for 125 Pualu Loop 33 of 38 Listing Image for 125 Pualu Loop 34 of 38 Listing Image for 125 Pualu Loop 35 of 38 Listing Image for 125 Pualu Loop 36 of 38 Listing Image for 125 Pualu Loop 37 of 38 Listing Image for 125 Pualu Loop 38 of 38

$1,388,000

↓ $107,000

Napili/Kahana/Honokowai

125 Pualu Loop, Napili/Kahana/Honokowai

3 Beds 2 Baths 1,376 SqFt Residential MLS® # 409810

Days on Market: 104

Moffett Properties LLC Cell: 808-870-6794

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

$1,999,000

↓ $151,000

Olinda Farm Lots

25 Lumahai Pl, Makawao/Olinda/Haliimaile

4 Beds 3 Baths 2,732 SqFt Residential MLS® # 409809

Days on Market: 104

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In Escrow
Listing Image for 311 Awalau Rd 1 of 41 Listing Image for 311 Awalau Rd 2 of 41 Listing Image for 311 Awalau Rd 3 of 41 Listing Image for 311 Awalau Rd 4 of 41 Listing Image for 311 Awalau Rd 5 of 41 Listing Image for 311 Awalau Rd 6 of 41 Listing Image for 311 Awalau Rd 7 of 41 Listing Image for 311 Awalau Rd 8 of 41 Listing Image for 311 Awalau Rd 9 of 41 Listing Image for 311 Awalau Rd 10 of 41 Listing Image for 311 Awalau Rd 11 of 41 Listing Image for 311 Awalau Rd 12 of 41 Listing Image for 311 Awalau Rd 13 of 41 Listing Image for 311 Awalau Rd 14 of 41 Listing Image for 311 Awalau Rd 15 of 41 Listing Image for 311 Awalau Rd 16 of 41 Listing Image for 311 Awalau Rd 17 of 41 Listing Image for 311 Awalau Rd 18 of 41 Listing Image for 311 Awalau Rd 19 of 41 Listing Image for 311 Awalau Rd 20 of 41 Listing Image for 311 Awalau Rd 21 of 41 Listing Image for 311 Awalau Rd 22 of 41 Listing Image for 311 Awalau Rd 23 of 41 Listing Image for 311 Awalau Rd 24 of 41 Listing Image for 311 Awalau Rd 25 of 41 Listing Image for 311 Awalau Rd 26 of 41 Listing Image for 311 Awalau Rd 27 of 41 Listing Image for 311 Awalau Rd 28 of 41 Listing Image for 311 Awalau Rd 29 of 41 Listing Image for 311 Awalau Rd 30 of 41 Listing Image for 311 Awalau Rd 31 of 41 Listing Image for 311 Awalau Rd 32 of 41 Listing Image for 311 Awalau Rd 33 of 41 Listing Image for 311 Awalau Rd 34 of 41 Listing Image for 311 Awalau Rd 35 of 41 Listing Image for 311 Awalau Rd 36 of 41 Listing Image for 311 Awalau Rd 37 of 41 Listing Image for 311 Awalau Rd 38 of 41 Listing Image for 311 Awalau Rd 39 of 41 Listing Image for 311 Awalau Rd 40 of 41 Listing Image for 311 Awalau Rd 41 of 41

$1,500,000

↓ $250,000

Haiku

311 Awalau Rd, Haiku

4 Beds 3.5 Baths 4,118 SqFt Residential MLS® # 409808

Days on Market: 104

Island Sotheby's International Realty(W) Cell: 808-283-7965

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: 02/10/2026
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$1,575,000

Kamaole One 11

2230 S Kihei Rd 11, Kihei

2 Beds 2 Baths 977 SqFt Residential MLS® # 408544 Date Sold: February 10, 2026
Sold
Closed: 02/11/2026
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$1,320,000

Paradise Ridge Estates 403

2757 S Kihei Rd 403, Kihei

3 Beds 2 Baths 1,389 SqFt Residential MLS® # 404693 Date Sold: February 11, 2026
Sold
Closed: 04/20/2026
Listing Image for 79 Kapihaa Pl 2b 1 of 23 Listing Image for 79 Kapihaa Pl 2b 2 of 23 Listing Image for 79 Kapihaa Pl 2b 3 of 23 Listing Image for 79 Kapihaa Pl 2b 4 of 23 Listing Image for 79 Kapihaa Pl 2b 5 of 23 Listing Image for 79 Kapihaa Pl 2b 6 of 23 Listing Image for 79 Kapihaa Pl 2b 7 of 23 Listing Image for 79 Kapihaa Pl 2b 8 of 23 Listing Image for 79 Kapihaa Pl 2b 9 of 23 Listing Image for 79 Kapihaa Pl 2b 10 of 23 Listing Image for 79 Kapihaa Pl 2b 11 of 23 Listing Image for 79 Kapihaa Pl 2b 12 of 23 Listing Image for 79 Kapihaa Pl 2b 13 of 23 Listing Image for 79 Kapihaa Pl 2b 14 of 23 Listing Image for 79 Kapihaa Pl 2b 15 of 23 Listing Image for 79 Kapihaa Pl 2b 16 of 23 Listing Image for 79 Kapihaa Pl 2b 17 of 23 Listing Image for 79 Kapihaa Pl 2b 18 of 23 Listing Image for 79 Kapihaa Pl 2b 19 of 23 Listing Image for 79 Kapihaa Pl 2b 20 of 23 Listing Image for 79 Kapihaa Pl 2b 21 of 23 Listing Image for 79 Kapihaa Pl 2b 22 of 23 Listing Image for 79 Kapihaa Pl 2b 23 of 23

$2,575,000

Terraces Manele Bay 2B

79 Kapihaa Pl 2b, Lanai

2 Beds 2.5 Baths 1,972 SqFt Residential MLS® # 408537 Date Sold: April 20, 2026
Sold
Closed: 04/10/2026
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$1,030,000

↓ $170,000

Waiakoa Kai Estates

264 Palanehe St, Kihei

3 Beds 2 Baths 1,405 SqFt Residential MLS® # 408536 Date Sold: April 10, 2026
Sold
Closed: 05/22/2026
Listing Image for 555 Halalai St 1 of 48 Listing Image for 555 Halalai St 2 of 48 Listing Image for 555 Halalai St 3 of 48 Listing Image for 555 Halalai St 4 of 48 Listing Image for 555 Halalai St 5 of 48 Listing Image for 555 Halalai St 6 of 48 Listing Image for 555 Halalai St 7 of 48 Listing Image for 555 Halalai St 8 of 48 Listing Image for 555 Halalai St 9 of 48 Listing Image for 555 Halalai St 10 of 48 Listing Image for 555 Halalai St 11 of 48 Listing Image for 555 Halalai St 12 of 48 Listing Image for 555 Halalai St 13 of 48 Listing Image for 555 Halalai St 14 of 48 Listing Image for 555 Halalai St 15 of 48 Listing Image for 555 Halalai St 16 of 48 Listing Image for 555 Halalai St 17 of 48 Listing Image for 555 Halalai St 18 of 48 Listing Image for 555 Halalai St 19 of 48 Listing Image for 555 Halalai St 20 of 48 Listing Image for 555 Halalai St 21 of 48 Listing Image for 555 Halalai St 22 of 48 Listing Image for 555 Halalai St 23 of 48 Listing Image for 555 Halalai St 24 of 48 Listing Image for 555 Halalai St 25 of 48 Listing Image for 555 Halalai St 26 of 48 Listing Image for 555 Halalai St 27 of 48 Listing Image for 555 Halalai St 28 of 48 Listing Image for 555 Halalai St 29 of 48 Listing Image for 555 Halalai St 30 of 48 Listing Image for 555 Halalai St 31 of 48 Listing Image for 555 Halalai St 32 of 48 Listing Image for 555 Halalai St 33 of 48 Listing Image for 555 Halalai St 34 of 48 Listing Image for 555 Halalai St 35 of 48 Listing Image for 555 Halalai St 36 of 48 Listing Image for 555 Halalai St 37 of 48 Listing Image for 555 Halalai St 38 of 48 Listing Image for 555 Halalai St 39 of 48 Listing Image for 555 Halalai St 40 of 48 Listing Image for 555 Halalai St 41 of 48 Listing Image for 555 Halalai St 42 of 48 Listing Image for 555 Halalai St 43 of 48 Listing Image for 555 Halalai St 44 of 48 Listing Image for 555 Halalai St 45 of 48 Listing Image for 555 Halalai St 46 of 48 Listing Image for 555 Halalai St 47 of 48 Listing Image for 555 Halalai St 48 of 48

$1,362,500

Ka Ono Ulu Estates

555 Halalai St, Kihei

3 Beds 2 Baths 1,830 SqFt Residential MLS® # 408531 Date Sold: May 22, 2026
Sold
Closed: 06/22/2026
Listing Image for 114 Mano Dr B 1 of 50 Listing Image for 114 Mano Dr B 2 of 50 Listing Image for 114 Mano Dr B 3 of 50 Listing Image for 114 Mano Dr B 4 of 50 Listing Image for 114 Mano Dr B 5 of 50 Listing Image for 114 Mano Dr B 6 of 50 Listing Image for 114 Mano Dr B 7 of 50 Listing Image for 114 Mano Dr B 8 of 50 Listing Image for 114 Mano Dr B 9 of 50 Listing Image for 114 Mano Dr B 10 of 50 Listing Image for 114 Mano Dr B 11 of 50 Listing Image for 114 Mano Dr B 12 of 50 Listing Image for 114 Mano Dr B 13 of 50 Listing Image for 114 Mano Dr B 14 of 50 Listing Image for 114 Mano Dr B 15 of 50 Listing Image for 114 Mano Dr B 16 of 50 Listing Image for 114 Mano Dr B 17 of 50 Listing Image for 114 Mano Dr B 18 of 50 Listing Image for 114 Mano Dr B 19 of 50 Listing Image for 114 Mano Dr B 20 of 50 Listing Image for 114 Mano Dr B 21 of 50 Listing Image for 114 Mano Dr B 22 of 50 Listing Image for 114 Mano Dr B 23 of 50 Listing Image for 114 Mano Dr B 24 of 50 Listing Image for 114 Mano Dr B 25 of 50 Listing Image for 114 Mano Dr B 26 of 50 Listing Image for 114 Mano Dr B 27 of 50 Listing Image for 114 Mano Dr B 28 of 50 Listing Image for 114 Mano Dr B 29 of 50 Listing Image for 114 Mano Dr B 30 of 50 Listing Image for 114 Mano Dr B 31 of 50 Listing Image for 114 Mano Dr B 32 of 50 Listing Image for 114 Mano Dr B 33 of 50 Listing Image for 114 Mano Dr B 34 of 50 Listing Image for 114 Mano Dr B 35 of 50 Listing Image for 114 Mano Dr B 36 of 50 Listing Image for 114 Mano Dr B 37 of 50 Listing Image for 114 Mano Dr B 38 of 50 Listing Image for 114 Mano Dr B 39 of 50 Listing Image for 114 Mano Dr B 40 of 50 Listing Image for 114 Mano Dr B 41 of 50 Listing Image for 114 Mano Dr B 42 of 50 Listing Image for 114 Mano Dr B 43 of 50 Listing Image for 114 Mano Dr B 44 of 50 Listing Image for 114 Mano Dr B 45 of 50 Listing Image for 114 Mano Dr B 46 of 50 Listing Image for 114 Mano Dr B 47 of 50 Listing Image for 114 Mano Dr B 48 of 50 Listing Image for 114 Mano Dr B 49 of 50 Listing Image for 114 Mano Dr B 50 of 50

$979,500

↓ $170,500

Kula Kai

114 Mano Dr B, Kula/Ulupalakua/Kanaio

2 Beds 1.5 Baths 859 SqFt Residential MLS® # 408528 Date Sold: June 22, 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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