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 68 Awaiku St B 1 of 36 Listing Image for 68 Awaiku St B 2 of 36 Listing Image for 68 Awaiku St B 3 of 36 Listing Image for 68 Awaiku St B 4 of 36 Listing Image for 68 Awaiku St B 5 of 36 Listing Image for 68 Awaiku St B 6 of 36 Listing Image for 68 Awaiku St B 7 of 36 Listing Image for 68 Awaiku St B 8 of 36 Listing Image for 68 Awaiku St B 9 of 36 Listing Image for 68 Awaiku St B 10 of 36 Listing Image for 68 Awaiku St B 11 of 36 Listing Image for 68 Awaiku St B 12 of 36 Listing Image for 68 Awaiku St B 13 of 36 Listing Image for 68 Awaiku St B 14 of 36 Listing Image for 68 Awaiku St B 15 of 36 Listing Image for 68 Awaiku St B 16 of 36 Listing Image for 68 Awaiku St B 17 of 36 Listing Image for 68 Awaiku St B 18 of 36 Listing Image for 68 Awaiku St B 19 of 36 Listing Image for 68 Awaiku St B 20 of 36 Listing Image for 68 Awaiku St B 21 of 36 Listing Image for 68 Awaiku St B 22 of 36 Listing Image for 68 Awaiku St B 23 of 36 Listing Image for 68 Awaiku St B 24 of 36 Listing Image for 68 Awaiku St B 25 of 36 Listing Image for 68 Awaiku St B 26 of 36 Listing Image for 68 Awaiku St B 27 of 36 Listing Image for 68 Awaiku St B 28 of 36 Listing Image for 68 Awaiku St B 29 of 36 Listing Image for 68 Awaiku St B 30 of 36 Listing Image for 68 Awaiku St B 31 of 36 Listing Image for 68 Awaiku St B 32 of 36 Listing Image for 68 Awaiku St B 33 of 36 Listing Image for 68 Awaiku St B 34 of 36 Listing Image for 68 Awaiku St B 35 of 36 Listing Image for 68 Awaiku St B 36 of 36

$1,399,000

↓ $96,000

Mahanalua Nui

68 Awaiku St B, Lahaina

2 Beds 2 Baths 1,033 SqFt Residential MLS® # 408793

Days on Market: 209

Compass Cell: 808-283-7214

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$11,900,000

Peahi

400 Mehana Rd, Haiku

3 Beds 3.5 Baths 5,403 SqFt Residential MLS® # 408784

Days on Market: 211

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

Listing Image for 104 Anapuni Loop 1 of 45 Listing Image for 104 Anapuni Loop 2 of 45 Listing Image for 104 Anapuni Loop 3 of 45 Listing Image for 104 Anapuni Loop 4 of 45 Listing Image for 104 Anapuni Loop 5 of 45 Listing Image for 104 Anapuni Loop 6 of 45 Listing Image for 104 Anapuni Loop 7 of 45 Listing Image for 104 Anapuni Loop 8 of 45 Listing Image for 104 Anapuni Loop 9 of 45 Listing Image for 104 Anapuni Loop 10 of 45 Listing Image for 104 Anapuni Loop 11 of 45 Listing Image for 104 Anapuni Loop 12 of 45 Listing Image for 104 Anapuni Loop 13 of 45 Listing Image for 104 Anapuni Loop 14 of 45 Listing Image for 104 Anapuni Loop 15 of 45 Listing Image for 104 Anapuni Loop 16 of 45 Listing Image for 104 Anapuni Loop 17 of 45 Listing Image for 104 Anapuni Loop 18 of 45 Listing Image for 104 Anapuni Loop 19 of 45 Listing Image for 104 Anapuni Loop 20 of 45 Listing Image for 104 Anapuni Loop 21 of 45 Listing Image for 104 Anapuni Loop 22 of 45 Listing Image for 104 Anapuni Loop 23 of 45 Listing Image for 104 Anapuni Loop 24 of 45 Listing Image for 104 Anapuni Loop 25 of 45 Listing Image for 104 Anapuni Loop 26 of 45 Listing Image for 104 Anapuni Loop 27 of 45 Listing Image for 104 Anapuni Loop 28 of 45 Listing Image for 104 Anapuni Loop 29 of 45 Listing Image for 104 Anapuni Loop 30 of 45 Listing Image for 104 Anapuni Loop 31 of 45 Listing Image for 104 Anapuni Loop 32 of 45 Listing Image for 104 Anapuni Loop 33 of 45 Listing Image for 104 Anapuni Loop 34 of 45 Listing Image for 104 Anapuni Loop 35 of 45 Listing Image for 104 Anapuni Loop 36 of 45 Listing Image for 104 Anapuni Loop 37 of 45 Listing Image for 104 Anapuni Loop 38 of 45 Listing Image for 104 Anapuni Loop 39 of 45 Listing Image for 104 Anapuni Loop 40 of 45 Listing Image for 104 Anapuni Loop 41 of 45 Listing Image for 104 Anapuni Loop 42 of 45 Listing Image for 104 Anapuni Loop 43 of 45 Listing Image for 104 Anapuni Loop 44 of 45 Listing Image for 104 Anapuni Loop 45 of 45

$7,400,000

Lanikeha

104 Anapuni Loop, Kaanapali

3 Beds 4.5 Baths 5,901 SqFt Residential MLS® # 408779

Days on Market: 211

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

In Escrow Short Term Rental
Listing Image for 4850 Makena Alanui Rd B304 1 of 48 Listing Image for 4850 Makena Alanui Rd B304 2 of 48 Listing Image for 4850 Makena Alanui Rd B304 3 of 48 Listing Image for 4850 Makena Alanui Rd B304 4 of 48 Listing Image for 4850 Makena Alanui Rd B304 5 of 48 Listing Image for 4850 Makena Alanui Rd B304 6 of 48 Listing Image for 4850 Makena Alanui Rd B304 7 of 48 Listing Image for 4850 Makena Alanui Rd B304 8 of 48 Listing Image for 4850 Makena Alanui Rd B304 9 of 48 Listing Image for 4850 Makena Alanui Rd B304 10 of 48 Listing Image for 4850 Makena Alanui Rd B304 11 of 48 Listing Image for 4850 Makena Alanui Rd B304 12 of 48 Listing Image for 4850 Makena Alanui Rd B304 13 of 48 Listing Image for 4850 Makena Alanui Rd B304 14 of 48 Listing Image for 4850 Makena Alanui Rd B304 15 of 48 Listing Image for 4850 Makena Alanui Rd B304 16 of 48 Listing Image for 4850 Makena Alanui Rd B304 17 of 48 Listing Image for 4850 Makena Alanui Rd B304 18 of 48 Listing Image for 4850 Makena Alanui Rd B304 19 of 48 Listing Image for 4850 Makena Alanui Rd B304 20 of 48 Listing Image for 4850 Makena Alanui Rd B304 21 of 48 Listing Image for 4850 Makena Alanui Rd B304 22 of 48 Listing Image for 4850 Makena Alanui Rd B304 23 of 48 Listing Image for 4850 Makena Alanui Rd B304 24 of 48 Listing Image for 4850 Makena Alanui Rd B304 25 of 48 Listing Image for 4850 Makena Alanui Rd B304 26 of 48 Listing Image for 4850 Makena Alanui Rd B304 27 of 48 Listing Image for 4850 Makena Alanui Rd B304 28 of 48 Listing Image for 4850 Makena Alanui Rd B304 29 of 48 Listing Image for 4850 Makena Alanui Rd B304 30 of 48 Listing Image for 4850 Makena Alanui Rd B304 31 of 48 Listing Image for 4850 Makena Alanui Rd B304 32 of 48 Listing Image for 4850 Makena Alanui Rd B304 33 of 48 Listing Image for 4850 Makena Alanui Rd B304 34 of 48 Listing Image for 4850 Makena Alanui Rd B304 35 of 48 Listing Image for 4850 Makena Alanui Rd B304 36 of 48 Listing Image for 4850 Makena Alanui Rd B304 37 of 48 Listing Image for 4850 Makena Alanui Rd B304 38 of 48 Listing Image for 4850 Makena Alanui Rd B304 39 of 48 Listing Image for 4850 Makena Alanui Rd B304 40 of 48 Listing Image for 4850 Makena Alanui Rd B304 41 of 48 Listing Image for 4850 Makena Alanui Rd B304 42 of 48 Listing Image for 4850 Makena Alanui Rd B304 43 of 48 Listing Image for 4850 Makena Alanui Rd B304 44 of 48 Listing Image for 4850 Makena Alanui Rd B304 45 of 48 Listing Image for 4850 Makena Alanui Rd B304 46 of 48 Listing Image for 4850 Makena Alanui Rd B304 47 of 48 Listing Image for 4850 Makena Alanui Rd B304 48 of 48

$3,495,000

↓ $355,000

Makena Surf B304

4850 Makena Alanui Rd B304, Wailea/Makena

2 Beds 2 Baths 1,038 SqFt Residential MLS® # 408777

Days on Market: 212

Keller Williams Realty Maui-Ka Cell: 808-344-8358

Listing Image for 1055 Kaupakalua Rd 1 of 50 Listing Image for 1055 Kaupakalua Rd 2 of 50 Listing Image for 1055 Kaupakalua Rd 3 of 50 Listing Image for 1055 Kaupakalua Rd 4 of 50 Listing Image for 1055 Kaupakalua Rd 5 of 50 Listing Image for 1055 Kaupakalua Rd 6 of 50 Listing Image for 1055 Kaupakalua Rd 7 of 50 Listing Image for 1055 Kaupakalua Rd 8 of 50 Listing Image for 1055 Kaupakalua Rd 9 of 50 Listing Image for 1055 Kaupakalua Rd 10 of 50 Listing Image for 1055 Kaupakalua Rd 11 of 50 Listing Image for 1055 Kaupakalua Rd 12 of 50 Listing Image for 1055 Kaupakalua Rd 13 of 50 Listing Image for 1055 Kaupakalua Rd 14 of 50 Listing Image for 1055 Kaupakalua Rd 15 of 50 Listing Image for 1055 Kaupakalua Rd 16 of 50 Listing Image for 1055 Kaupakalua Rd 17 of 50 Listing Image for 1055 Kaupakalua Rd 18 of 50 Listing Image for 1055 Kaupakalua Rd 19 of 50 Listing Image for 1055 Kaupakalua Rd 20 of 50 Listing Image for 1055 Kaupakalua Rd 21 of 50 Listing Image for 1055 Kaupakalua Rd 22 of 50 Listing Image for 1055 Kaupakalua Rd 23 of 50 Listing Image for 1055 Kaupakalua Rd 24 of 50 Listing Image for 1055 Kaupakalua Rd 25 of 50 Listing Image for 1055 Kaupakalua Rd 26 of 50 Listing Image for 1055 Kaupakalua Rd 27 of 50 Listing Image for 1055 Kaupakalua Rd 28 of 50 Listing Image for 1055 Kaupakalua Rd 29 of 50 Listing Image for 1055 Kaupakalua Rd 30 of 50 Listing Image for 1055 Kaupakalua Rd 31 of 50 Listing Image for 1055 Kaupakalua Rd 32 of 50 Listing Image for 1055 Kaupakalua Rd 33 of 50 Listing Image for 1055 Kaupakalua Rd 34 of 50 Listing Image for 1055 Kaupakalua Rd 35 of 50 Listing Image for 1055 Kaupakalua Rd 36 of 50 Listing Image for 1055 Kaupakalua Rd 37 of 50 Listing Image for 1055 Kaupakalua Rd 38 of 50 Listing Image for 1055 Kaupakalua Rd 39 of 50 Listing Image for 1055 Kaupakalua Rd 40 of 50 Listing Image for 1055 Kaupakalua Rd 41 of 50 Listing Image for 1055 Kaupakalua Rd 42 of 50 Listing Image for 1055 Kaupakalua Rd 43 of 50 Listing Image for 1055 Kaupakalua Rd 44 of 50 Listing Image for 1055 Kaupakalua Rd 45 of 50 Listing Image for 1055 Kaupakalua Rd 46 of 50 Listing Image for 1055 Kaupakalua Rd 47 of 50 Listing Image for 1055 Kaupakalua Rd 48 of 50 Listing Image for 1055 Kaupakalua Rd 49 of 50 Listing Image for 1055 Kaupakalua Rd 50 of 50

$2,995,000

↓ $500,000

Haiku

1055 Kaupakalua Rd, Haiku

5 Beds 3 Baths 4,550 SqFt Residential MLS® # 408773

Days on Market: 212

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

Short Term Rental
Listing Image for 110 Kaanapali Shores Pl 1017 1 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 2 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 3 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 4 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 5 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 6 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 7 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 8 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 9 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 10 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 11 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 12 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 13 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 14 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 15 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 16 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 17 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 18 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 19 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 20 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 21 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 22 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 23 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 24 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 25 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 26 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 27 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 28 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 29 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 30 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 31 of 32 Listing Image for 110 Kaanapali Shores Pl 1017 32 of 32

$1,249,000

Mahana 1017

110 Kaanapali Shores Pl 1017, Kaanapali

1 Bed 1 Bath 820 SqFt Residential MLS® # 408771

Days on Market: 212

Living Maui Real Estate LLC Cell: 808-359-1161

Short Term Rental
Listing Image for 110 Kaanapali Shores Pl 907 1 of 36 Listing Image for 110 Kaanapali Shores Pl 907 2 of 36 Listing Image for 110 Kaanapali Shores Pl 907 3 of 36 Listing Image for 110 Kaanapali Shores Pl 907 4 of 36 Listing Image for 110 Kaanapali Shores Pl 907 5 of 36 Listing Image for 110 Kaanapali Shores Pl 907 6 of 36 Listing Image for 110 Kaanapali Shores Pl 907 7 of 36 Listing Image for 110 Kaanapali Shores Pl 907 8 of 36 Listing Image for 110 Kaanapali Shores Pl 907 9 of 36 Listing Image for 110 Kaanapali Shores Pl 907 10 of 36 Listing Image for 110 Kaanapali Shores Pl 907 11 of 36 Listing Image for 110 Kaanapali Shores Pl 907 12 of 36 Listing Image for 110 Kaanapali Shores Pl 907 13 of 36 Listing Image for 110 Kaanapali Shores Pl 907 14 of 36 Listing Image for 110 Kaanapali Shores Pl 907 15 of 36 Listing Image for 110 Kaanapali Shores Pl 907 16 of 36 Listing Image for 110 Kaanapali Shores Pl 907 17 of 36 Listing Image for 110 Kaanapali Shores Pl 907 18 of 36 Listing Image for 110 Kaanapali Shores Pl 907 19 of 36 Listing Image for 110 Kaanapali Shores Pl 907 20 of 36 Listing Image for 110 Kaanapali Shores Pl 907 21 of 36 Listing Image for 110 Kaanapali Shores Pl 907 22 of 36 Listing Image for 110 Kaanapali Shores Pl 907 23 of 36 Listing Image for 110 Kaanapali Shores Pl 907 24 of 36 Listing Image for 110 Kaanapali Shores Pl 907 25 of 36 Listing Image for 110 Kaanapali Shores Pl 907 26 of 36 Listing Image for 110 Kaanapali Shores Pl 907 27 of 36 Listing Image for 110 Kaanapali Shores Pl 907 28 of 36 Listing Image for 110 Kaanapali Shores Pl 907 29 of 36 Listing Image for 110 Kaanapali Shores Pl 907 30 of 36 Listing Image for 110 Kaanapali Shores Pl 907 31 of 36 Listing Image for 110 Kaanapali Shores Pl 907 32 of 36 Listing Image for 110 Kaanapali Shores Pl 907 33 of 36 Listing Image for 110 Kaanapali Shores Pl 907 34 of 36 Listing Image for 110 Kaanapali Shores Pl 907 35 of 36 Listing Image for 110 Kaanapali Shores Pl 907 36 of 36

$1,195,000

Mahana 907

110 Kaanapali Shores Pl 907, Kaanapali

1 Bed 1 Bath 820 SqFt Residential MLS® # 408767

Days on Market: 212

Living Maui Real Estate LLC Cell: 808-359-1161

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: 12/29/2025
Listing Image for 50 Nohea Kai Dr 1-703 1 of 28 Listing Image for 50 Nohea Kai Dr 1-703 2 of 28 Listing Image for 50 Nohea Kai Dr 1-703 3 of 28 Listing Image for 50 Nohea Kai Dr 1-703 4 of 28 Listing Image for 50 Nohea Kai Dr 1-703 5 of 28 Listing Image for 50 Nohea Kai Dr 1-703 6 of 28 Listing Image for 50 Nohea Kai Dr 1-703 7 of 28 Listing Image for 50 Nohea Kai Dr 1-703 8 of 28 Listing Image for 50 Nohea Kai Dr 1-703 9 of 28 Listing Image for 50 Nohea Kai Dr 1-703 10 of 28 Listing Image for 50 Nohea Kai Dr 1-703 11 of 28 Listing Image for 50 Nohea Kai Dr 1-703 12 of 28 Listing Image for 50 Nohea Kai Dr 1-703 13 of 28 Listing Image for 50 Nohea Kai Dr 1-703 14 of 28 Listing Image for 50 Nohea Kai Dr 1-703 15 of 28 Listing Image for 50 Nohea Kai Dr 1-703 16 of 28 Listing Image for 50 Nohea Kai Dr 1-703 17 of 28 Listing Image for 50 Nohea Kai Dr 1-703 18 of 28 Listing Image for 50 Nohea Kai Dr 1-703 19 of 28 Listing Image for 50 Nohea Kai Dr 1-703 20 of 28 Listing Image for 50 Nohea Kai Dr 1-703 21 of 28 Listing Image for 50 Nohea Kai Dr 1-703 22 of 28 Listing Image for 50 Nohea Kai Dr 1-703 23 of 28 Listing Image for 50 Nohea Kai Dr 1-703 24 of 28 Listing Image for 50 Nohea Kai Dr 1-703 25 of 28 Listing Image for 50 Nohea Kai Dr 1-703 26 of 28 Listing Image for 50 Nohea Kai Dr 1-703 27 of 28 Listing Image for 50 Nohea Kai Dr 1-703 28 of 28

$3,295,000

Kaanapali Alii 1-703

50 Nohea Kai Dr 1-703, Kaanapali

2 Beds 2 Baths 1,675 SqFt Residential MLS® # 407653 Date Sold: December 29, 2025
Sold
Closed: 02/12/2026
Listing Image for 104 Kamahao Cir Lot #49 1 of 38 Listing Image for 104 Kamahao Cir Lot #49 2 of 38 Listing Image for 104 Kamahao Cir Lot #49 3 of 38 Listing Image for 104 Kamahao Cir Lot #49 4 of 38 Listing Image for 104 Kamahao Cir Lot #49 5 of 38 Listing Image for 104 Kamahao Cir Lot #49 6 of 38 Listing Image for 104 Kamahao Cir Lot #49 7 of 38 Listing Image for 104 Kamahao Cir Lot #49 8 of 38 Listing Image for 104 Kamahao Cir Lot #49 9 of 38 Listing Image for 104 Kamahao Cir Lot #49 10 of 38 Listing Image for 104 Kamahao Cir Lot #49 11 of 38 Listing Image for 104 Kamahao Cir Lot #49 12 of 38 Listing Image for 104 Kamahao Cir Lot #49 13 of 38 Listing Image for 104 Kamahao Cir Lot #49 14 of 38 Listing Image for 104 Kamahao Cir Lot #49 15 of 38 Listing Image for 104 Kamahao Cir Lot #49 16 of 38 Listing Image for 104 Kamahao Cir Lot #49 17 of 38 Listing Image for 104 Kamahao Cir Lot #49 18 of 38 Listing Image for 104 Kamahao Cir Lot #49 19 of 38 Listing Image for 104 Kamahao Cir Lot #49 20 of 38 Listing Image for 104 Kamahao Cir Lot #49 21 of 38 Listing Image for 104 Kamahao Cir Lot #49 22 of 38 Listing Image for 104 Kamahao Cir Lot #49 23 of 38 Listing Image for 104 Kamahao Cir Lot #49 24 of 38 Listing Image for 104 Kamahao Cir Lot #49 25 of 38 Listing Image for 104 Kamahao Cir Lot #49 26 of 38 Listing Image for 104 Kamahao Cir Lot #49 27 of 38 Listing Image for 104 Kamahao Cir Lot #49 28 of 38 Listing Image for 104 Kamahao Cir Lot #49 29 of 38 Listing Image for 104 Kamahao Cir Lot #49 30 of 38 Listing Image for 104 Kamahao Cir Lot #49 31 of 38 Listing Image for 104 Kamahao Cir Lot #49 32 of 38 Listing Image for 104 Kamahao Cir Lot #49 33 of 38 Listing Image for 104 Kamahao Cir Lot #49 34 of 38 Listing Image for 104 Kamahao Cir Lot #49 35 of 38 Listing Image for 104 Kamahao Cir Lot #49 36 of 38 Listing Image for 104 Kamahao Cir Lot #49 37 of 38 Listing Image for 104 Kamahao Cir Lot #49 38 of 38

$1,050,000

↓ $110,000

Waikapu Gardens

104 Kamahao Cir Lot #49, Wailuku

4 Beds 3 Baths 1,584 SqFt Residential MLS® # 407649 Date Sold: February 12, 2026
Sold
Closed: 12/24/2025
Listing Image for 105 Honuhula Pl 1 of 34 Listing Image for 105 Honuhula Pl 2 of 34 Listing Image for 105 Honuhula Pl 3 of 34 Listing Image for 105 Honuhula Pl 4 of 34 Listing Image for 105 Honuhula Pl 5 of 34 Listing Image for 105 Honuhula Pl 6 of 34 Listing Image for 105 Honuhula Pl 7 of 34 Listing Image for 105 Honuhula Pl 8 of 34 Listing Image for 105 Honuhula Pl 9 of 34 Listing Image for 105 Honuhula Pl 10 of 34 Listing Image for 105 Honuhula Pl 11 of 34 Listing Image for 105 Honuhula Pl 12 of 34 Listing Image for 105 Honuhula Pl 13 of 34 Listing Image for 105 Honuhula Pl 14 of 34 Listing Image for 105 Honuhula Pl 15 of 34 Listing Image for 105 Honuhula Pl 16 of 34 Listing Image for 105 Honuhula Pl 17 of 34 Listing Image for 105 Honuhula Pl 18 of 34 Listing Image for 105 Honuhula Pl 19 of 34 Listing Image for 105 Honuhula Pl 20 of 34 Listing Image for 105 Honuhula Pl 21 of 34 Listing Image for 105 Honuhula Pl 22 of 34 Listing Image for 105 Honuhula Pl 23 of 34 Listing Image for 105 Honuhula Pl 24 of 34 Listing Image for 105 Honuhula Pl 25 of 34 Listing Image for 105 Honuhula Pl 26 of 34 Listing Image for 105 Honuhula Pl 27 of 34 Listing Image for 105 Honuhula Pl 28 of 34 Listing Image for 105 Honuhula Pl 29 of 34 Listing Image for 105 Honuhula Pl 30 of 34 Listing Image for 105 Honuhula Pl 31 of 34 Listing Image for 105 Honuhula Pl 32 of 34 Listing Image for 105 Honuhula Pl 33 of 34 Listing Image for 105 Honuhula Pl 34 of 34

$1,650,000

Honu Alahele

105 Honuhula Pl, Kihei

4 Beds 2.5 Baths 1,822 SqFt Residential MLS® # 407648 Date Sold: December 24, 2025
Sold
Closed: 03/20/2026
Listing Image for 54 Hua Nui Way 1 of 42 Listing Image for 54 Hua Nui Way 2 of 42 Listing Image for 54 Hua Nui Way 3 of 42 Listing Image for 54 Hua Nui Way 4 of 42 Listing Image for 54 Hua Nui Way 5 of 42 Listing Image for 54 Hua Nui Way 6 of 42 Listing Image for 54 Hua Nui Way 7 of 42 Listing Image for 54 Hua Nui Way 8 of 42 Listing Image for 54 Hua Nui Way 9 of 42 Listing Image for 54 Hua Nui Way 10 of 42 Listing Image for 54 Hua Nui Way 11 of 42 Listing Image for 54 Hua Nui Way 12 of 42 Listing Image for 54 Hua Nui Way 13 of 42 Listing Image for 54 Hua Nui Way 14 of 42 Listing Image for 54 Hua Nui Way 15 of 42 Listing Image for 54 Hua Nui Way 16 of 42 Listing Image for 54 Hua Nui Way 17 of 42 Listing Image for 54 Hua Nui Way 18 of 42 Listing Image for 54 Hua Nui Way 19 of 42 Listing Image for 54 Hua Nui Way 20 of 42 Listing Image for 54 Hua Nui Way 21 of 42 Listing Image for 54 Hua Nui Way 22 of 42 Listing Image for 54 Hua Nui Way 23 of 42 Listing Image for 54 Hua Nui Way 24 of 42 Listing Image for 54 Hua Nui Way 25 of 42 Listing Image for 54 Hua Nui Way 26 of 42 Listing Image for 54 Hua Nui Way 27 of 42 Listing Image for 54 Hua Nui Way 28 of 42 Listing Image for 54 Hua Nui Way 29 of 42 Listing Image for 54 Hua Nui Way 30 of 42 Listing Image for 54 Hua Nui Way 31 of 42 Listing Image for 54 Hua Nui Way 32 of 42 Listing Image for 54 Hua Nui Way 33 of 42 Listing Image for 54 Hua Nui Way 34 of 42 Listing Image for 54 Hua Nui Way 35 of 42 Listing Image for 54 Hua Nui Way 36 of 42 Listing Image for 54 Hua Nui Way 37 of 42 Listing Image for 54 Hua Nui Way 38 of 42 Listing Image for 54 Hua Nui Way 39 of 42 Listing Image for 54 Hua Nui Way 40 of 42 Listing Image for 54 Hua Nui Way 41 of 42 Listing Image for 54 Hua Nui Way 42 of 42

$1,500,000

Kahana Wai

54 Hua Nui Way, Napili/Kahana/Honokowai

3 Beds 2.5 Baths 1,926 SqFt Residential MLS® # 407647 Date Sold: March 20, 2026
Sold
Closed: 03/17/2026
Listing Image for 2180 Auina Pl 1 of 50 Listing Image for 2180 Auina Pl 2 of 50 Listing Image for 2180 Auina Pl 3 of 50 Listing Image for 2180 Auina Pl 4 of 50 Listing Image for 2180 Auina Pl 5 of 50 Listing Image for 2180 Auina Pl 6 of 50 Listing Image for 2180 Auina Pl 7 of 50 Listing Image for 2180 Auina Pl 8 of 50 Listing Image for 2180 Auina Pl 9 of 50 Listing Image for 2180 Auina Pl 10 of 50 Listing Image for 2180 Auina Pl 11 of 50 Listing Image for 2180 Auina Pl 12 of 50 Listing Image for 2180 Auina Pl 13 of 50 Listing Image for 2180 Auina Pl 14 of 50 Listing Image for 2180 Auina Pl 15 of 50 Listing Image for 2180 Auina Pl 16 of 50 Listing Image for 2180 Auina Pl 17 of 50 Listing Image for 2180 Auina Pl 18 of 50 Listing Image for 2180 Auina Pl 19 of 50 Listing Image for 2180 Auina Pl 20 of 50 Listing Image for 2180 Auina Pl 21 of 50 Listing Image for 2180 Auina Pl 22 of 50 Listing Image for 2180 Auina Pl 23 of 50 Listing Image for 2180 Auina Pl 24 of 50 Listing Image for 2180 Auina Pl 25 of 50 Listing Image for 2180 Auina Pl 26 of 50 Listing Image for 2180 Auina Pl 27 of 50 Listing Image for 2180 Auina Pl 28 of 50 Listing Image for 2180 Auina Pl 29 of 50 Listing Image for 2180 Auina Pl 30 of 50 Listing Image for 2180 Auina Pl 31 of 50 Listing Image for 2180 Auina Pl 32 of 50 Listing Image for 2180 Auina Pl 33 of 50 Listing Image for 2180 Auina Pl 34 of 50 Listing Image for 2180 Auina Pl 35 of 50 Listing Image for 2180 Auina Pl 36 of 50 Listing Image for 2180 Auina Pl 37 of 50 Listing Image for 2180 Auina Pl 38 of 50 Listing Image for 2180 Auina Pl 39 of 50 Listing Image for 2180 Auina Pl 40 of 50 Listing Image for 2180 Auina Pl 41 of 50 Listing Image for 2180 Auina Pl 42 of 50 Listing Image for 2180 Auina Pl 43 of 50 Listing Image for 2180 Auina Pl 44 of 50 Listing Image for 2180 Auina Pl 45 of 50 Listing Image for 2180 Auina Pl 46 of 50 Listing Image for 2180 Auina Pl 47 of 50 Listing Image for 2180 Auina Pl 48 of 50 Listing Image for 2180 Auina Pl 49 of 50 Listing Image for 2180 Auina Pl 50 of 50

$1,410,000

↓ $40,000

Kihei

2180 Auina Pl, Kihei

3 Beds 2 Baths 1,716 SqFt Residential MLS® # 407645 Date Sold: March 17, 2026
Sold
Closed: 06/25/2026
Listing Image for 161 Wailea Ike Pl C204 1 of 25 Listing Image for 161 Wailea Ike Pl C204 2 of 25 Listing Image for 161 Wailea Ike Pl C204 3 of 25 Listing Image for 161 Wailea Ike Pl C204 4 of 25 Listing Image for 161 Wailea Ike Pl C204 5 of 25 Listing Image for 161 Wailea Ike Pl C204 6 of 25 Listing Image for 161 Wailea Ike Pl C204 7 of 25 Listing Image for 161 Wailea Ike Pl C204 8 of 25 Listing Image for 161 Wailea Ike Pl C204 9 of 25 Listing Image for 161 Wailea Ike Pl C204 10 of 25 Listing Image for 161 Wailea Ike Pl C204 11 of 25 Listing Image for 161 Wailea Ike Pl C204 12 of 25 Listing Image for 161 Wailea Ike Pl C204 13 of 25 Listing Image for 161 Wailea Ike Pl C204 14 of 25 Listing Image for 161 Wailea Ike Pl C204 15 of 25 Listing Image for 161 Wailea Ike Pl C204 16 of 25 Listing Image for 161 Wailea Ike Pl C204 17 of 25 Listing Image for 161 Wailea Ike Pl C204 18 of 25 Listing Image for 161 Wailea Ike Pl C204 19 of 25 Listing Image for 161 Wailea Ike Pl C204 20 of 25 Listing Image for 161 Wailea Ike Pl C204 21 of 25 Listing Image for 161 Wailea Ike Pl C204 22 of 25 Listing Image for 161 Wailea Ike Pl C204 23 of 25 Listing Image for 161 Wailea Ike Pl C204 24 of 25 Listing Image for 161 Wailea Ike Pl C204 25 of 25

$1,765,000

↓ $485,000

Wailea Town Center C204

161 Wailea Ike Pl C204, Wailea/Makena

3 Beds 3 Baths 1,910 SqFt Residential MLS® # 407643 Date Sold: June 25, 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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