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 165 Waikoloa Rd 1 of 50 Listing Image for 165 Waikoloa Rd 2 of 50 Listing Image for 165 Waikoloa Rd 3 of 50 Listing Image for 165 Waikoloa Rd 4 of 50 Listing Image for 165 Waikoloa Rd 5 of 50 Listing Image for 165 Waikoloa Rd 6 of 50 Listing Image for 165 Waikoloa Rd 7 of 50 Listing Image for 165 Waikoloa Rd 8 of 50 Listing Image for 165 Waikoloa Rd 9 of 50 Listing Image for 165 Waikoloa Rd 10 of 50 Listing Image for 165 Waikoloa Rd 11 of 50 Listing Image for 165 Waikoloa Rd 12 of 50 Listing Image for 165 Waikoloa Rd 13 of 50 Listing Image for 165 Waikoloa Rd 14 of 50 Listing Image for 165 Waikoloa Rd 15 of 50 Listing Image for 165 Waikoloa Rd 16 of 50 Listing Image for 165 Waikoloa Rd 17 of 50 Listing Image for 165 Waikoloa Rd 18 of 50 Listing Image for 165 Waikoloa Rd 19 of 50 Listing Image for 165 Waikoloa Rd 20 of 50 Listing Image for 165 Waikoloa Rd 21 of 50 Listing Image for 165 Waikoloa Rd 22 of 50 Listing Image for 165 Waikoloa Rd 23 of 50 Listing Image for 165 Waikoloa Rd 24 of 50 Listing Image for 165 Waikoloa Rd 25 of 50 Listing Image for 165 Waikoloa Rd 26 of 50 Listing Image for 165 Waikoloa Rd 27 of 50 Listing Image for 165 Waikoloa Rd 28 of 50 Listing Image for 165 Waikoloa Rd 29 of 50 Listing Image for 165 Waikoloa Rd 30 of 50 Listing Image for 165 Waikoloa Rd 31 of 50 Listing Image for 165 Waikoloa Rd 32 of 50 Listing Image for 165 Waikoloa Rd 33 of 50 Listing Image for 165 Waikoloa Rd 34 of 50 Listing Image for 165 Waikoloa Rd 35 of 50 Listing Image for 165 Waikoloa Rd 36 of 50 Listing Image for 165 Waikoloa Rd 37 of 50 Listing Image for 165 Waikoloa Rd 38 of 50 Listing Image for 165 Waikoloa Rd 39 of 50 Listing Image for 165 Waikoloa Rd 40 of 50 Listing Image for 165 Waikoloa Rd 41 of 50 Listing Image for 165 Waikoloa Rd 42 of 50 Listing Image for 165 Waikoloa Rd 43 of 50 Listing Image for 165 Waikoloa Rd 44 of 50 Listing Image for 165 Waikoloa Rd 45 of 50 Listing Image for 165 Waikoloa Rd 46 of 50 Listing Image for 165 Waikoloa Rd 47 of 50 Listing Image for 165 Waikoloa Rd 48 of 50 Listing Image for 165 Waikoloa Rd 49 of 50 Listing Image for 165 Waikoloa Rd 50 of 50

$949,000

↓ $40,000

Hana

165 Waikoloa Rd, Hana

2 Beds 2 Baths 1,318 SqFt Residential MLS® # 407458

Days on Market: 335

Maui Lifestyle Realty LLC Cell: 808-280-8167

Short Term Rental
Listing Image for 155 Wailea Ike Pl 111 1 of 37 Listing Image for 155 Wailea Ike Pl 111 2 of 37 Listing Image for 155 Wailea Ike Pl 111 3 of 37 Listing Image for 155 Wailea Ike Pl 111 4 of 37 Listing Image for 155 Wailea Ike Pl 111 5 of 37 Listing Image for 155 Wailea Ike Pl 111 6 of 37 Listing Image for 155 Wailea Ike Pl 111 7 of 37 Listing Image for 155 Wailea Ike Pl 111 8 of 37 Listing Image for 155 Wailea Ike Pl 111 9 of 37 Listing Image for 155 Wailea Ike Pl 111 10 of 37 Listing Image for 155 Wailea Ike Pl 111 11 of 37 Listing Image for 155 Wailea Ike Pl 111 12 of 37 Listing Image for 155 Wailea Ike Pl 111 13 of 37 Listing Image for 155 Wailea Ike Pl 111 14 of 37 Listing Image for 155 Wailea Ike Pl 111 15 of 37 Listing Image for 155 Wailea Ike Pl 111 16 of 37 Listing Image for 155 Wailea Ike Pl 111 17 of 37 Listing Image for 155 Wailea Ike Pl 111 18 of 37 Listing Image for 155 Wailea Ike Pl 111 19 of 37 Listing Image for 155 Wailea Ike Pl 111 20 of 37 Listing Image for 155 Wailea Ike Pl 111 21 of 37 Listing Image for 155 Wailea Ike Pl 111 22 of 37 Listing Image for 155 Wailea Ike Pl 111 23 of 37 Listing Image for 155 Wailea Ike Pl 111 24 of 37 Listing Image for 155 Wailea Ike Pl 111 25 of 37 Listing Image for 155 Wailea Ike Pl 111 26 of 37 Listing Image for 155 Wailea Ike Pl 111 27 of 37 Listing Image for 155 Wailea Ike Pl 111 28 of 37 Listing Image for 155 Wailea Ike Pl 111 29 of 37 Listing Image for 155 Wailea Ike Pl 111 30 of 37 Listing Image for 155 Wailea Ike Pl 111 31 of 37 Listing Image for 155 Wailea Ike Pl 111 32 of 37 Listing Image for 155 Wailea Ike Pl 111 33 of 37 Listing Image for 155 Wailea Ike Pl 111 34 of 37 Listing Image for 155 Wailea Ike Pl 111 35 of 37 Listing Image for 155 Wailea Ike Pl 111 36 of 37 Listing Image for 155 Wailea Ike Pl 111 37 of 37

$949,900

↓ $50,099

Grand Champions 111

155 Wailea Ike Pl 111, Wailea/Makena

2 Beds 2 Baths 1,056 SqFt Residential MLS® # 407428

Days on Market: 336

Hawaii Life (W) Cell: 808-280-2055

Listing Image for 53 Waikai St 1 of 49 Listing Image for 53 Waikai St 2 of 49 Listing Image for 53 Waikai St 3 of 49 Listing Image for 53 Waikai St 4 of 49 Listing Image for 53 Waikai St 5 of 49 Listing Image for 53 Waikai St 6 of 49 Listing Image for 53 Waikai St 7 of 49 Listing Image for 53 Waikai St 8 of 49 Listing Image for 53 Waikai St 9 of 49 Listing Image for 53 Waikai St 10 of 49 Listing Image for 53 Waikai St 11 of 49 Listing Image for 53 Waikai St 12 of 49 Listing Image for 53 Waikai St 13 of 49 Listing Image for 53 Waikai St 14 of 49 Listing Image for 53 Waikai St 15 of 49 Listing Image for 53 Waikai St 16 of 49 Listing Image for 53 Waikai St 17 of 49 Listing Image for 53 Waikai St 18 of 49 Listing Image for 53 Waikai St 19 of 49 Listing Image for 53 Waikai St 20 of 49 Listing Image for 53 Waikai St 21 of 49 Listing Image for 53 Waikai St 22 of 49 Listing Image for 53 Waikai St 23 of 49 Listing Image for 53 Waikai St 24 of 49 Listing Image for 53 Waikai St 25 of 49 Listing Image for 53 Waikai St 26 of 49 Listing Image for 53 Waikai St 27 of 49 Listing Image for 53 Waikai St 28 of 49 Listing Image for 53 Waikai St 29 of 49 Listing Image for 53 Waikai St 30 of 49 Listing Image for 53 Waikai St 31 of 49 Listing Image for 53 Waikai St 32 of 49 Listing Image for 53 Waikai St 33 of 49 Listing Image for 53 Waikai St 34 of 49 Listing Image for 53 Waikai St 35 of 49 Listing Image for 53 Waikai St 36 of 49 Listing Image for 53 Waikai St 37 of 49 Listing Image for 53 Waikai St 38 of 49 Listing Image for 53 Waikai St 39 of 49 Listing Image for 53 Waikai St 40 of 49 Listing Image for 53 Waikai St 41 of 49 Listing Image for 53 Waikai St 42 of 49 Listing Image for 53 Waikai St 43 of 49 Listing Image for 53 Waikai St 44 of 49 Listing Image for 53 Waikai St 45 of 49 Listing Image for 53 Waikai St 46 of 49 Listing Image for 53 Waikai St 47 of 49 Listing Image for 53 Waikai St 48 of 49 Listing Image for 53 Waikai St 49 of 49

$1,750,000

↓ $125,000

Wailea Kai

53 Waikai St, Wailea/Makena

4 Beds 2.5 Baths 2,400 SqFt Residential MLS® # 407427

Days on Market: 336

Compass-W

Listing Image for 7850 Kula Hwy 1 of 35 Listing Image for 7850 Kula Hwy 2 of 35 Listing Image for 7850 Kula Hwy 3 of 35 Listing Image for 7850 Kula Hwy 4 of 35 Listing Image for 7850 Kula Hwy 5 of 35 Listing Image for 7850 Kula Hwy 6 of 35 Listing Image for 7850 Kula Hwy 7 of 35 Listing Image for 7850 Kula Hwy 8 of 35 Listing Image for 7850 Kula Hwy 9 of 35 Listing Image for 7850 Kula Hwy 10 of 35 Listing Image for 7850 Kula Hwy 11 of 35 Listing Image for 7850 Kula Hwy 12 of 35 Listing Image for 7850 Kula Hwy 13 of 35 Listing Image for 7850 Kula Hwy 14 of 35 Listing Image for 7850 Kula Hwy 15 of 35 Listing Image for 7850 Kula Hwy 16 of 35 Listing Image for 7850 Kula Hwy 17 of 35 Listing Image for 7850 Kula Hwy 18 of 35 Listing Image for 7850 Kula Hwy 19 of 35 Listing Image for 7850 Kula Hwy 20 of 35 Listing Image for 7850 Kula Hwy 21 of 35 Listing Image for 7850 Kula Hwy 22 of 35 Listing Image for 7850 Kula Hwy 23 of 35 Listing Image for 7850 Kula Hwy 24 of 35 Listing Image for 7850 Kula Hwy 25 of 35 Listing Image for 7850 Kula Hwy 26 of 35 Listing Image for 7850 Kula Hwy 27 of 35 Listing Image for 7850 Kula Hwy 28 of 35 Listing Image for 7850 Kula Hwy 29 of 35 Listing Image for 7850 Kula Hwy 30 of 35 Listing Image for 7850 Kula Hwy 31 of 35 Listing Image for 7850 Kula Hwy 32 of 35 Listing Image for 7850 Kula Hwy 33 of 35 Listing Image for 7850 Kula Hwy 34 of 35 Listing Image for 7850 Kula Hwy 35 of 35

$6,499,000

↓ $496,000

Kula/Ulupalakua/Kanaio

7850 Kula Hwy, Kula/Ulupalakua/Kanaio

3 Beds 2.5 Baths 3,832 SqFt Residential MLS® # 407426

Days on Market: 336

Hawaii Life (W) Cell: 808-283-2222

Short Term Rental
Listing Image for 3445 Lower Honoapiilani Rd 457 1 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 2 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 3 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 4 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 5 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 6 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 7 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 8 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 9 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 10 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 11 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 12 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 13 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 14 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 15 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 16 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 17 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 18 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 19 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 20 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 21 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 22 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 23 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 24 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 25 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 26 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 27 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 28 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 29 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 30 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 31 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 32 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 33 of 34 Listing Image for 3445 Lower Honoapiilani Rd 457 34 of 34

$1,850,000

↓ $500,000

Kaanapali Shores 457

3445 Lower Honoapiilani Rd 457, Kaanapali

3 Beds 2 Baths 1,364 SqFt Residential MLS® # 407422

Days on Market: 337

Keller Williams Realty Maui-L Cell: 808-870-2525

Short Term Rental
Listing Image for 3445 Lower Honoapiilani Rd 456 1 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 2 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 3 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 4 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 5 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 6 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 7 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 8 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 9 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 10 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 11 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 12 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 13 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 14 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 15 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 16 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 17 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 18 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 19 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 20 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 21 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 22 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 23 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 24 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 25 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 26 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 27 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 28 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 29 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 30 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 31 of 32 Listing Image for 3445 Lower Honoapiilani Rd 456 32 of 32

$1,699,000

↓ $501,000

Kaanapali Shores 456

3445 Lower Honoapiilani Rd 456, Kaanapali

3 Beds 2 Baths 1,364 SqFt Residential MLS® # 407421

Days on Market: 337

Keller Williams Realty Maui-L Cell: 808-870-2525

In Escrow
Listing Image for 7421 Makena Rd 1 of 50 Listing Image for 7421 Makena Rd 2 of 50 Listing Image for 7421 Makena Rd 3 of 50 Listing Image for 7421 Makena Rd 4 of 50 Listing Image for 7421 Makena Rd 5 of 50 Listing Image for 7421 Makena Rd 6 of 50 Listing Image for 7421 Makena Rd 7 of 50 Listing Image for 7421 Makena Rd 8 of 50 Listing Image for 7421 Makena Rd 9 of 50 Listing Image for 7421 Makena Rd 10 of 50 Listing Image for 7421 Makena Rd 11 of 50 Listing Image for 7421 Makena Rd 12 of 50 Listing Image for 7421 Makena Rd 13 of 50 Listing Image for 7421 Makena Rd 14 of 50 Listing Image for 7421 Makena Rd 15 of 50 Listing Image for 7421 Makena Rd 16 of 50 Listing Image for 7421 Makena Rd 17 of 50 Listing Image for 7421 Makena Rd 18 of 50 Listing Image for 7421 Makena Rd 19 of 50 Listing Image for 7421 Makena Rd 20 of 50 Listing Image for 7421 Makena Rd 21 of 50 Listing Image for 7421 Makena Rd 22 of 50 Listing Image for 7421 Makena Rd 23 of 50 Listing Image for 7421 Makena Rd 24 of 50 Listing Image for 7421 Makena Rd 25 of 50 Listing Image for 7421 Makena Rd 26 of 50 Listing Image for 7421 Makena Rd 27 of 50 Listing Image for 7421 Makena Rd 28 of 50 Listing Image for 7421 Makena Rd 29 of 50 Listing Image for 7421 Makena Rd 30 of 50 Listing Image for 7421 Makena Rd 31 of 50 Listing Image for 7421 Makena Rd 32 of 50 Listing Image for 7421 Makena Rd 33 of 50 Listing Image for 7421 Makena Rd 34 of 50 Listing Image for 7421 Makena Rd 35 of 50 Listing Image for 7421 Makena Rd 36 of 50 Listing Image for 7421 Makena Rd 37 of 50 Listing Image for 7421 Makena Rd 38 of 50 Listing Image for 7421 Makena Rd 39 of 50 Listing Image for 7421 Makena Rd 40 of 50 Listing Image for 7421 Makena Rd 41 of 50 Listing Image for 7421 Makena Rd 42 of 50 Listing Image for 7421 Makena Rd 43 of 50 Listing Image for 7421 Makena Rd 44 of 50 Listing Image for 7421 Makena Rd 45 of 50 Listing Image for 7421 Makena Rd 46 of 50 Listing Image for 7421 Makena Rd 47 of 50 Listing Image for 7421 Makena Rd 48 of 50 Listing Image for 7421 Makena Rd 49 of 50 Listing Image for 7421 Makena Rd 50 of 50

$19,950,000

↓ $1,900,000

Wailea/Makena

7421 Makena Rd, Wailea/Makena

4 Beds 5 Baths 4,544 SqFt Residential MLS® # 407419

Days on Market: 337

Compass-W

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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: 02/26/2026
Listing Image for 128 Hoopalua Dr 1 of 50 Listing Image for 128 Hoopalua Dr 2 of 50 Listing Image for 128 Hoopalua Dr 3 of 50 Listing Image for 128 Hoopalua Dr 4 of 50 Listing Image for 128 Hoopalua Dr 5 of 50 Listing Image for 128 Hoopalua Dr 6 of 50 Listing Image for 128 Hoopalua Dr 7 of 50 Listing Image for 128 Hoopalua Dr 8 of 50 Listing Image for 128 Hoopalua Dr 9 of 50 Listing Image for 128 Hoopalua Dr 10 of 50 Listing Image for 128 Hoopalua Dr 11 of 50 Listing Image for 128 Hoopalua Dr 12 of 50 Listing Image for 128 Hoopalua Dr 13 of 50 Listing Image for 128 Hoopalua Dr 14 of 50 Listing Image for 128 Hoopalua Dr 15 of 50 Listing Image for 128 Hoopalua Dr 16 of 50 Listing Image for 128 Hoopalua Dr 17 of 50 Listing Image for 128 Hoopalua Dr 18 of 50 Listing Image for 128 Hoopalua Dr 19 of 50 Listing Image for 128 Hoopalua Dr 20 of 50 Listing Image for 128 Hoopalua Dr 21 of 50 Listing Image for 128 Hoopalua Dr 22 of 50 Listing Image for 128 Hoopalua Dr 23 of 50 Listing Image for 128 Hoopalua Dr 24 of 50 Listing Image for 128 Hoopalua Dr 25 of 50 Listing Image for 128 Hoopalua Dr 26 of 50 Listing Image for 128 Hoopalua Dr 27 of 50 Listing Image for 128 Hoopalua Dr 28 of 50 Listing Image for 128 Hoopalua Dr 29 of 50 Listing Image for 128 Hoopalua Dr 30 of 50 Listing Image for 128 Hoopalua Dr 31 of 50 Listing Image for 128 Hoopalua Dr 32 of 50 Listing Image for 128 Hoopalua Dr 33 of 50 Listing Image for 128 Hoopalua Dr 34 of 50 Listing Image for 128 Hoopalua Dr 35 of 50 Listing Image for 128 Hoopalua Dr 36 of 50 Listing Image for 128 Hoopalua Dr 37 of 50 Listing Image for 128 Hoopalua Dr 38 of 50 Listing Image for 128 Hoopalua Dr 39 of 50 Listing Image for 128 Hoopalua Dr 40 of 50 Listing Image for 128 Hoopalua Dr 41 of 50 Listing Image for 128 Hoopalua Dr 42 of 50 Listing Image for 128 Hoopalua Dr 43 of 50 Listing Image for 128 Hoopalua Dr 44 of 50 Listing Image for 128 Hoopalua Dr 45 of 50 Listing Image for 128 Hoopalua Dr 46 of 50 Listing Image for 128 Hoopalua Dr 47 of 50 Listing Image for 128 Hoopalua Dr 48 of 50 Listing Image for 128 Hoopalua Dr 49 of 50 Listing Image for 128 Hoopalua Dr 50 of 50

$1,900,000

↓ $225,000

Kula 200

128 Hoopalua Dr, Makawao/Olinda/Haliimaile

3 Beds 2 Baths 2,560 SqFt Residential MLS® # 407152 Date Sold: February 26, 2026
Sold
Closed: 03/05/2026
Listing Image for 18 Puuaina Pl 1 of 49 Listing Image for 18 Puuaina Pl 2 of 49 Listing Image for 18 Puuaina Pl 3 of 49 Listing Image for 18 Puuaina Pl 4 of 49 Listing Image for 18 Puuaina Pl 5 of 49 Listing Image for 18 Puuaina Pl 6 of 49 Listing Image for 18 Puuaina Pl 7 of 49 Listing Image for 18 Puuaina Pl 8 of 49 Listing Image for 18 Puuaina Pl 9 of 49 Listing Image for 18 Puuaina Pl 10 of 49 Listing Image for 18 Puuaina Pl 11 of 49 Listing Image for 18 Puuaina Pl 12 of 49 Listing Image for 18 Puuaina Pl 13 of 49 Listing Image for 18 Puuaina Pl 14 of 49 Listing Image for 18 Puuaina Pl 15 of 49 Listing Image for 18 Puuaina Pl 16 of 49 Listing Image for 18 Puuaina Pl 17 of 49 Listing Image for 18 Puuaina Pl 18 of 49 Listing Image for 18 Puuaina Pl 19 of 49 Listing Image for 18 Puuaina Pl 20 of 49 Listing Image for 18 Puuaina Pl 21 of 49 Listing Image for 18 Puuaina Pl 22 of 49 Listing Image for 18 Puuaina Pl 23 of 49 Listing Image for 18 Puuaina Pl 24 of 49 Listing Image for 18 Puuaina Pl 25 of 49 Listing Image for 18 Puuaina Pl 26 of 49 Listing Image for 18 Puuaina Pl 27 of 49 Listing Image for 18 Puuaina Pl 28 of 49 Listing Image for 18 Puuaina Pl 29 of 49 Listing Image for 18 Puuaina Pl 30 of 49 Listing Image for 18 Puuaina Pl 31 of 49 Listing Image for 18 Puuaina Pl 32 of 49 Listing Image for 18 Puuaina Pl 33 of 49 Listing Image for 18 Puuaina Pl 34 of 49 Listing Image for 18 Puuaina Pl 35 of 49 Listing Image for 18 Puuaina Pl 36 of 49 Listing Image for 18 Puuaina Pl 37 of 49 Listing Image for 18 Puuaina Pl 38 of 49 Listing Image for 18 Puuaina Pl 39 of 49 Listing Image for 18 Puuaina Pl 40 of 49 Listing Image for 18 Puuaina Pl 41 of 49 Listing Image for 18 Puuaina Pl 42 of 49 Listing Image for 18 Puuaina Pl 43 of 49 Listing Image for 18 Puuaina Pl 44 of 49 Listing Image for 18 Puuaina Pl 45 of 49 Listing Image for 18 Puuaina Pl 46 of 49 Listing Image for 18 Puuaina Pl 47 of 49 Listing Image for 18 Puuaina Pl 48 of 49 Listing Image for 18 Puuaina Pl 49 of 49

$1,165,000

The Island at Maui Lani

18 Puuaina Pl, Kahului

3 Beds 3 Baths 2,198 SqFt Residential MLS® # 407124 Date Sold: March 5, 2026
Sold
Closed: 10/29/2025
Listing Image for 2724 Panepoo St St 1 of 32 Listing Image for 2724 Panepoo St St 2 of 32 Listing Image for 2724 Panepoo St St 3 of 32 Listing Image for 2724 Panepoo St St 4 of 32 Listing Image for 2724 Panepoo St St 5 of 32 Listing Image for 2724 Panepoo St St 6 of 32 Listing Image for 2724 Panepoo St St 7 of 32 Listing Image for 2724 Panepoo St St 8 of 32 Listing Image for 2724 Panepoo St St 9 of 32 Listing Image for 2724 Panepoo St St 10 of 32 Listing Image for 2724 Panepoo St St 11 of 32 Listing Image for 2724 Panepoo St St 12 of 32 Listing Image for 2724 Panepoo St St 13 of 32 Listing Image for 2724 Panepoo St St 14 of 32 Listing Image for 2724 Panepoo St St 15 of 32 Listing Image for 2724 Panepoo St St 16 of 32 Listing Image for 2724 Panepoo St St 17 of 32 Listing Image for 2724 Panepoo St St 18 of 32 Listing Image for 2724 Panepoo St St 19 of 32 Listing Image for 2724 Panepoo St St 20 of 32 Listing Image for 2724 Panepoo St St 21 of 32 Listing Image for 2724 Panepoo St St 22 of 32 Listing Image for 2724 Panepoo St St 23 of 32 Listing Image for 2724 Panepoo St St 24 of 32 Listing Image for 2724 Panepoo St St 25 of 32 Listing Image for 2724 Panepoo St St 26 of 32 Listing Image for 2724 Panepoo St St 27 of 32 Listing Image for 2724 Panepoo St St 28 of 32 Listing Image for 2724 Panepoo St St 29 of 32 Listing Image for 2724 Panepoo St St 30 of 32 Listing Image for 2724 Panepoo St St 31 of 32 Listing Image for 2724 Panepoo St St 32 of 32

$959,000

Kihei Village Sub

2724 Panepoo St St, Kihei

3 Beds 2 Baths 1,684 SqFt Residential MLS® # 407153 Date Sold: October 29, 2025
Sold
Closed: 02/02/2026
Listing Image for 516 Hihimanu St 34 1 of 47 Listing Image for 516 Hihimanu St 34 2 of 47 Listing Image for 516 Hihimanu St 34 3 of 47 Listing Image for 516 Hihimanu St 34 4 of 47 Listing Image for 516 Hihimanu St 34 5 of 47 Listing Image for 516 Hihimanu St 34 6 of 47 Listing Image for 516 Hihimanu St 34 7 of 47 Listing Image for 516 Hihimanu St 34 8 of 47 Listing Image for 516 Hihimanu St 34 9 of 47 Listing Image for 516 Hihimanu St 34 10 of 47 Listing Image for 516 Hihimanu St 34 11 of 47 Listing Image for 516 Hihimanu St 34 12 of 47 Listing Image for 516 Hihimanu St 34 13 of 47 Listing Image for 516 Hihimanu St 34 14 of 47 Listing Image for 516 Hihimanu St 34 15 of 47 Listing Image for 516 Hihimanu St 34 16 of 47 Listing Image for 516 Hihimanu St 34 17 of 47 Listing Image for 516 Hihimanu St 34 18 of 47 Listing Image for 516 Hihimanu St 34 19 of 47 Listing Image for 516 Hihimanu St 34 20 of 47 Listing Image for 516 Hihimanu St 34 21 of 47 Listing Image for 516 Hihimanu St 34 22 of 47 Listing Image for 516 Hihimanu St 34 23 of 47 Listing Image for 516 Hihimanu St 34 24 of 47 Listing Image for 516 Hihimanu St 34 25 of 47 Listing Image for 516 Hihimanu St 34 26 of 47 Listing Image for 516 Hihimanu St 34 27 of 47 Listing Image for 516 Hihimanu St 34 28 of 47 Listing Image for 516 Hihimanu St 34 29 of 47 Listing Image for 516 Hihimanu St 34 30 of 47 Listing Image for 516 Hihimanu St 34 31 of 47 Listing Image for 516 Hihimanu St 34 32 of 47 Listing Image for 516 Hihimanu St 34 33 of 47 Listing Image for 516 Hihimanu St 34 34 of 47 Listing Image for 516 Hihimanu St 34 35 of 47 Listing Image for 516 Hihimanu St 34 36 of 47 Listing Image for 516 Hihimanu St 34 37 of 47 Listing Image for 516 Hihimanu St 34 38 of 47 Listing Image for 516 Hihimanu St 34 39 of 47 Listing Image for 516 Hihimanu St 34 40 of 47 Listing Image for 516 Hihimanu St 34 41 of 47 Listing Image for 516 Hihimanu St 34 42 of 47 Listing Image for 516 Hihimanu St 34 43 of 47 Listing Image for 516 Hihimanu St 34 44 of 47 Listing Image for 516 Hihimanu St 34 45 of 47 Listing Image for 516 Hihimanu St 34 46 of 47 Listing Image for 516 Hihimanu St 34 47 of 47

$1,450,000

↓ $245,000

Hokulani Golf Villas 34

516 Hihimanu St 34, Kihei

2 Beds 2 Baths 1,902 SqFt Residential MLS® # 407082 Date Sold: February 2, 2026
Buying Real Estate on Maui

Buying Real Estate on Maui

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

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Sold
Closed: 03/25/2026
Listing Image for 117 Kawailani Cir 1 of 43 Listing Image for 117 Kawailani Cir 2 of 43 Listing Image for 117 Kawailani Cir 3 of 43 Listing Image for 117 Kawailani Cir 4 of 43 Listing Image for 117 Kawailani Cir 5 of 43 Listing Image for 117 Kawailani Cir 6 of 43 Listing Image for 117 Kawailani Cir 7 of 43 Listing Image for 117 Kawailani Cir 8 of 43 Listing Image for 117 Kawailani Cir 9 of 43 Listing Image for 117 Kawailani Cir 10 of 43 Listing Image for 117 Kawailani Cir 11 of 43 Listing Image for 117 Kawailani Cir 12 of 43 Listing Image for 117 Kawailani Cir 13 of 43 Listing Image for 117 Kawailani Cir 14 of 43 Listing Image for 117 Kawailani Cir 15 of 43 Listing Image for 117 Kawailani Cir 16 of 43 Listing Image for 117 Kawailani Cir 17 of 43 Listing Image for 117 Kawailani Cir 18 of 43 Listing Image for 117 Kawailani Cir 19 of 43 Listing Image for 117 Kawailani Cir 20 of 43 Listing Image for 117 Kawailani Cir 21 of 43 Listing Image for 117 Kawailani Cir 22 of 43 Listing Image for 117 Kawailani Cir 23 of 43 Listing Image for 117 Kawailani Cir 24 of 43 Listing Image for 117 Kawailani Cir 25 of 43 Listing Image for 117 Kawailani Cir 26 of 43 Listing Image for 117 Kawailani Cir 27 of 43 Listing Image for 117 Kawailani Cir 28 of 43 Listing Image for 117 Kawailani Cir 29 of 43 Listing Image for 117 Kawailani Cir 30 of 43 Listing Image for 117 Kawailani Cir 31 of 43 Listing Image for 117 Kawailani Cir 32 of 43 Listing Image for 117 Kawailani Cir 33 of 43 Listing Image for 117 Kawailani Cir 34 of 43 Listing Image for 117 Kawailani Cir 35 of 43 Listing Image for 117 Kawailani Cir 36 of 43 Listing Image for 117 Kawailani Cir 37 of 43 Listing Image for 117 Kawailani Cir 38 of 43 Listing Image for 117 Kawailani Cir 39 of 43 Listing Image for 117 Kawailani Cir 40 of 43 Listing Image for 117 Kawailani Cir 41 of 43 Listing Image for 117 Kawailani Cir 42 of 43 Listing Image for 117 Kawailani Cir 43 of 43

$975,000

↓ $124,000

Piilani Village II

117 Kawailani Cir, Kihei

3 Beds 2 Baths 1,256 SqFt Residential MLS® # 407200 Date Sold: March 25, 2026
Sold
Closed: 11/10/2025
Listing Image for 2661 Kekaa Dr H-202 1 of 50 Listing Image for 2661 Kekaa Dr H-202 2 of 50 Listing Image for 2661 Kekaa Dr H-202 3 of 50 Listing Image for 2661 Kekaa Dr H-202 4 of 50 Listing Image for 2661 Kekaa Dr H-202 5 of 50 Listing Image for 2661 Kekaa Dr H-202 6 of 50 Listing Image for 2661 Kekaa Dr H-202 7 of 50 Listing Image for 2661 Kekaa Dr H-202 8 of 50 Listing Image for 2661 Kekaa Dr H-202 9 of 50 Listing Image for 2661 Kekaa Dr H-202 10 of 50 Listing Image for 2661 Kekaa Dr H-202 11 of 50 Listing Image for 2661 Kekaa Dr H-202 12 of 50 Listing Image for 2661 Kekaa Dr H-202 13 of 50 Listing Image for 2661 Kekaa Dr H-202 14 of 50 Listing Image for 2661 Kekaa Dr H-202 15 of 50 Listing Image for 2661 Kekaa Dr H-202 16 of 50 Listing Image for 2661 Kekaa Dr H-202 17 of 50 Listing Image for 2661 Kekaa Dr H-202 18 of 50 Listing Image for 2661 Kekaa Dr H-202 19 of 50 Listing Image for 2661 Kekaa Dr H-202 20 of 50 Listing Image for 2661 Kekaa Dr H-202 21 of 50 Listing Image for 2661 Kekaa Dr H-202 22 of 50 Listing Image for 2661 Kekaa Dr H-202 23 of 50 Listing Image for 2661 Kekaa Dr H-202 24 of 50 Listing Image for 2661 Kekaa Dr H-202 25 of 50 Listing Image for 2661 Kekaa Dr H-202 26 of 50 Listing Image for 2661 Kekaa Dr H-202 27 of 50 Listing Image for 2661 Kekaa Dr H-202 28 of 50 Listing Image for 2661 Kekaa Dr H-202 29 of 50 Listing Image for 2661 Kekaa Dr H-202 30 of 50 Listing Image for 2661 Kekaa Dr H-202 31 of 50 Listing Image for 2661 Kekaa Dr H-202 32 of 50 Listing Image for 2661 Kekaa Dr H-202 33 of 50 Listing Image for 2661 Kekaa Dr H-202 34 of 50 Listing Image for 2661 Kekaa Dr H-202 35 of 50 Listing Image for 2661 Kekaa Dr H-202 36 of 50 Listing Image for 2661 Kekaa Dr H-202 37 of 50 Listing Image for 2661 Kekaa Dr H-202 38 of 50 Listing Image for 2661 Kekaa Dr H-202 39 of 50 Listing Image for 2661 Kekaa Dr H-202 40 of 50 Listing Image for 2661 Kekaa Dr H-202 41 of 50 Listing Image for 2661 Kekaa Dr H-202 42 of 50 Listing Image for 2661 Kekaa Dr H-202 43 of 50 Listing Image for 2661 Kekaa Dr H-202 44 of 50 Listing Image for 2661 Kekaa Dr H-202 45 of 50 Listing Image for 2661 Kekaa Dr H-202 46 of 50 Listing Image for 2661 Kekaa Dr H-202 47 of 50 Listing Image for 2661 Kekaa Dr H-202 48 of 50 Listing Image for 2661 Kekaa Dr H-202 49 of 50 Listing Image for 2661 Kekaa Dr H-202 50 of 50

$1,325,000

Maui Eldorado H-202

2661 Kekaa Dr H-202, Kaanapali

2 Beds 2 Baths 1,440 SqFt Residential MLS® # 407197 Date Sold: November 10, 2025
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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