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 67 Wailea Gateway Pl 6-103 1 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 2 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 3 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 4 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 5 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 6 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 7 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 8 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 9 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 10 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 11 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 12 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 13 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 14 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 15 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 16 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 17 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 18 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 19 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 20 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 21 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 22 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 23 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 24 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 25 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 26 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 27 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 28 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 29 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 30 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 31 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 32 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 33 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 34 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 35 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 36 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 37 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 38 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 39 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 40 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 41 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 42 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 43 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 44 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 45 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 46 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 47 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 48 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 49 of 50 Listing Image for 67 Wailea Gateway Pl 6-103 50 of 50

$1,670,000

↓ $10,000

Keala O Wailea 6-103

67 Wailea Gateway Pl 6-103, Wailea/Makena

2 Beds 2 Baths 1,238 SqFt Residential MLS® # 410361

Days on Market: 52

Hawaii Life (W) Cell: 808-298-7455

Listing Image for 10 Meakoho Pl 1 of 24 Listing Image for 10 Meakoho Pl 2 of 24 Listing Image for 10 Meakoho Pl 3 of 24 Listing Image for 10 Meakoho Pl 4 of 24 Listing Image for 10 Meakoho Pl 5 of 24 Listing Image for 10 Meakoho Pl 6 of 24 Listing Image for 10 Meakoho Pl 7 of 24 Listing Image for 10 Meakoho Pl 8 of 24 Listing Image for 10 Meakoho Pl 9 of 24 Listing Image for 10 Meakoho Pl 10 of 24 Listing Image for 10 Meakoho Pl 11 of 24 Listing Image for 10 Meakoho Pl 12 of 24 Listing Image for 10 Meakoho Pl 13 of 24 Listing Image for 10 Meakoho Pl 14 of 24 Listing Image for 10 Meakoho Pl 15 of 24 Listing Image for 10 Meakoho Pl 16 of 24 Listing Image for 10 Meakoho Pl 17 of 24 Listing Image for 10 Meakoho Pl 18 of 24 Listing Image for 10 Meakoho Pl 19 of 24 Listing Image for 10 Meakoho Pl 20 of 24 Listing Image for 10 Meakoho Pl 21 of 24 Listing Image for 10 Meakoho Pl 22 of 24 Listing Image for 10 Meakoho Pl 23 of 24 Listing Image for 10 Meakoho Pl 24 of 24

$1,295,000

Kula/Ulupalakua/Kanaio

10 Meakoho Pl, Kula/Ulupalakua/Kanaio

3 Beds 2 Baths 1,660 SqFt Residential MLS® # 410360

Days on Market: 51

Nathalie Mullinix Rlty Universal Inc

Listing Image for 34 Hune One Ln 12-102 1 of 50 Listing Image for 34 Hune One Ln 12-102 2 of 50 Listing Image for 34 Hune One Ln 12-102 3 of 50 Listing Image for 34 Hune One Ln 12-102 4 of 50 Listing Image for 34 Hune One Ln 12-102 5 of 50 Listing Image for 34 Hune One Ln 12-102 6 of 50 Listing Image for 34 Hune One Ln 12-102 7 of 50 Listing Image for 34 Hune One Ln 12-102 8 of 50 Listing Image for 34 Hune One Ln 12-102 9 of 50 Listing Image for 34 Hune One Ln 12-102 10 of 50 Listing Image for 34 Hune One Ln 12-102 11 of 50 Listing Image for 34 Hune One Ln 12-102 12 of 50 Listing Image for 34 Hune One Ln 12-102 13 of 50 Listing Image for 34 Hune One Ln 12-102 14 of 50 Listing Image for 34 Hune One Ln 12-102 15 of 50 Listing Image for 34 Hune One Ln 12-102 16 of 50 Listing Image for 34 Hune One Ln 12-102 17 of 50 Listing Image for 34 Hune One Ln 12-102 18 of 50 Listing Image for 34 Hune One Ln 12-102 19 of 50 Listing Image for 34 Hune One Ln 12-102 20 of 50 Listing Image for 34 Hune One Ln 12-102 21 of 50 Listing Image for 34 Hune One Ln 12-102 22 of 50 Listing Image for 34 Hune One Ln 12-102 23 of 50 Listing Image for 34 Hune One Ln 12-102 24 of 50 Listing Image for 34 Hune One Ln 12-102 25 of 50 Listing Image for 34 Hune One Ln 12-102 26 of 50 Listing Image for 34 Hune One Ln 12-102 27 of 50 Listing Image for 34 Hune One Ln 12-102 28 of 50 Listing Image for 34 Hune One Ln 12-102 29 of 50 Listing Image for 34 Hune One Ln 12-102 30 of 50 Listing Image for 34 Hune One Ln 12-102 31 of 50 Listing Image for 34 Hune One Ln 12-102 32 of 50 Listing Image for 34 Hune One Ln 12-102 33 of 50 Listing Image for 34 Hune One Ln 12-102 34 of 50 Listing Image for 34 Hune One Ln 12-102 35 of 50 Listing Image for 34 Hune One Ln 12-102 36 of 50 Listing Image for 34 Hune One Ln 12-102 37 of 50 Listing Image for 34 Hune One Ln 12-102 38 of 50 Listing Image for 34 Hune One Ln 12-102 39 of 50 Listing Image for 34 Hune One Ln 12-102 40 of 50 Listing Image for 34 Hune One Ln 12-102 41 of 50 Listing Image for 34 Hune One Ln 12-102 42 of 50 Listing Image for 34 Hune One Ln 12-102 43 of 50 Listing Image for 34 Hune One Ln 12-102 44 of 50 Listing Image for 34 Hune One Ln 12-102 45 of 50 Listing Image for 34 Hune One Ln 12-102 46 of 50 Listing Image for 34 Hune One Ln 12-102 47 of 50 Listing Image for 34 Hune One Ln 12-102 48 of 50 Listing Image for 34 Hune One Ln 12-102 49 of 50 Listing Image for 34 Hune One Ln 12-102 50 of 50

$859,000

Kai Ani Village 12-102

34 Hune One Ln 12-102, Kihei

2 Beds 2 Baths 1,032 SqFt Residential MLS® # 410359

Days on Market: 51

Coldwell Banker Island Prop-Ku Cell: 808-633-2410

Listing Image for 4851 Lower Honoapiilani Rd 1 of 38 Listing Image for 4851 Lower Honoapiilani Rd 2 of 38 Listing Image for 4851 Lower Honoapiilani Rd 3 of 38 Listing Image for 4851 Lower Honoapiilani Rd 4 of 38 Listing Image for 4851 Lower Honoapiilani Rd 5 of 38 Listing Image for 4851 Lower Honoapiilani Rd 6 of 38 Listing Image for 4851 Lower Honoapiilani Rd 7 of 38 Listing Image for 4851 Lower Honoapiilani Rd 8 of 38 Listing Image for 4851 Lower Honoapiilani Rd 9 of 38 Listing Image for 4851 Lower Honoapiilani Rd 10 of 38 Listing Image for 4851 Lower Honoapiilani Rd 11 of 38 Listing Image for 4851 Lower Honoapiilani Rd 12 of 38 Listing Image for 4851 Lower Honoapiilani Rd 13 of 38 Listing Image for 4851 Lower Honoapiilani Rd 14 of 38 Listing Image for 4851 Lower Honoapiilani Rd 15 of 38 Listing Image for 4851 Lower Honoapiilani Rd 16 of 38 Listing Image for 4851 Lower Honoapiilani Rd 17 of 38 Listing Image for 4851 Lower Honoapiilani Rd 18 of 38 Listing Image for 4851 Lower Honoapiilani Rd 19 of 38 Listing Image for 4851 Lower Honoapiilani Rd 20 of 38 Listing Image for 4851 Lower Honoapiilani Rd 21 of 38 Listing Image for 4851 Lower Honoapiilani Rd 22 of 38 Listing Image for 4851 Lower Honoapiilani Rd 23 of 38 Listing Image for 4851 Lower Honoapiilani Rd 24 of 38 Listing Image for 4851 Lower Honoapiilani Rd 25 of 38 Listing Image for 4851 Lower Honoapiilani Rd 26 of 38 Listing Image for 4851 Lower Honoapiilani Rd 27 of 38 Listing Image for 4851 Lower Honoapiilani Rd 28 of 38 Listing Image for 4851 Lower Honoapiilani Rd 29 of 38 Listing Image for 4851 Lower Honoapiilani Rd 30 of 38 Listing Image for 4851 Lower Honoapiilani Rd 31 of 38 Listing Image for 4851 Lower Honoapiilani Rd 32 of 38 Listing Image for 4851 Lower Honoapiilani Rd 33 of 38 Listing Image for 4851 Lower Honoapiilani Rd 34 of 38 Listing Image for 4851 Lower Honoapiilani Rd 35 of 38 Listing Image for 4851 Lower Honoapiilani Rd 36 of 38 Listing Image for 4851 Lower Honoapiilani Rd 37 of 38 Listing Image for 4851 Lower Honoapiilani Rd 38 of 38

$12,000,000

Napili/Kahana/Honokowai

4851 Lower Honoapiilani Rd, Napili/Kahana/Honokowai

4 Beds 3.5 Baths 5,294 SqFt Residential MLS® # 410353

Days on Market: 52

Coldwell Banker Island Prop-KP Cell: 808-250-1583

In Escrow Short Term Rental
Listing Image for 3300 Wailea Alanui Dr 40e 1 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 2 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 3 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 4 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 5 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 6 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 7 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 8 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 9 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 10 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 11 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 12 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 13 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 14 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 15 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 16 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 17 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 18 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 19 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 20 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 21 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 22 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 23 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 24 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 25 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 26 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 27 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 28 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 29 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 30 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 31 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 32 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 33 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 34 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 35 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 36 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 37 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 38 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 39 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 40 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 41 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 42 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 43 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 44 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 45 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 46 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 47 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 48 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 49 of 50 Listing Image for 3300 Wailea Alanui Dr 40e 50 of 50

$1,399,000

Wailea Ekahi 40E

3300 Wailea Alanui Dr 40e, Wailea/Makena

1 Bed 2 Baths 952 SqFt Residential MLS® # 410343

Days on Market: 53

Romvari Realty Ltd

Listing Image for 63 Papahi Loop 1 of 20 Listing Image for 63 Papahi Loop 2 of 20 Listing Image for 63 Papahi Loop 3 of 20 Listing Image for 63 Papahi Loop 4 of 20 Listing Image for 63 Papahi Loop 5 of 20 Listing Image for 63 Papahi Loop 6 of 20 Listing Image for 63 Papahi Loop 7 of 20 Listing Image for 63 Papahi Loop 8 of 20 Listing Image for 63 Papahi Loop 9 of 20 Listing Image for 63 Papahi Loop 10 of 20 Listing Image for 63 Papahi Loop 11 of 20 Listing Image for 63 Papahi Loop 12 of 20 Listing Image for 63 Papahi Loop 13 of 20 Listing Image for 63 Papahi Loop 14 of 20 Listing Image for 63 Papahi Loop 15 of 20 Listing Image for 63 Papahi Loop 16 of 20 Listing Image for 63 Papahi Loop 17 of 20 Listing Image for 63 Papahi Loop 18 of 20 Listing Image for 63 Papahi Loop 19 of 20 Listing Image for 63 Papahi Loop 20 of 20

$1,065,000

↓ $160,000

Maui Lani

63 Papahi Loop, Kahului

3 Beds 3.5 Baths 1,601 SqFt Residential MLS® # 410340

Days on Market: 53

Realty 1st Inc kwee@realty-1st.com

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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: 06/18/2026
Listing Image for 24 Kahoea Pl 1 of 50 Listing Image for 24 Kahoea Pl 2 of 50 Listing Image for 24 Kahoea Pl 3 of 50 Listing Image for 24 Kahoea Pl 4 of 50 Listing Image for 24 Kahoea Pl 5 of 50 Listing Image for 24 Kahoea Pl 6 of 50 Listing Image for 24 Kahoea Pl 7 of 50 Listing Image for 24 Kahoea Pl 8 of 50 Listing Image for 24 Kahoea Pl 9 of 50 Listing Image for 24 Kahoea Pl 10 of 50 Listing Image for 24 Kahoea Pl 11 of 50 Listing Image for 24 Kahoea Pl 12 of 50 Listing Image for 24 Kahoea Pl 13 of 50 Listing Image for 24 Kahoea Pl 14 of 50 Listing Image for 24 Kahoea Pl 15 of 50 Listing Image for 24 Kahoea Pl 16 of 50 Listing Image for 24 Kahoea Pl 17 of 50 Listing Image for 24 Kahoea Pl 18 of 50 Listing Image for 24 Kahoea Pl 19 of 50 Listing Image for 24 Kahoea Pl 20 of 50 Listing Image for 24 Kahoea Pl 21 of 50 Listing Image for 24 Kahoea Pl 22 of 50 Listing Image for 24 Kahoea Pl 23 of 50 Listing Image for 24 Kahoea Pl 24 of 50 Listing Image for 24 Kahoea Pl 25 of 50 Listing Image for 24 Kahoea Pl 26 of 50 Listing Image for 24 Kahoea Pl 27 of 50 Listing Image for 24 Kahoea Pl 28 of 50 Listing Image for 24 Kahoea Pl 29 of 50 Listing Image for 24 Kahoea Pl 30 of 50 Listing Image for 24 Kahoea Pl 31 of 50 Listing Image for 24 Kahoea Pl 32 of 50 Listing Image for 24 Kahoea Pl 33 of 50 Listing Image for 24 Kahoea Pl 34 of 50 Listing Image for 24 Kahoea Pl 35 of 50 Listing Image for 24 Kahoea Pl 36 of 50 Listing Image for 24 Kahoea Pl 37 of 50 Listing Image for 24 Kahoea Pl 38 of 50 Listing Image for 24 Kahoea Pl 39 of 50 Listing Image for 24 Kahoea Pl 40 of 50 Listing Image for 24 Kahoea Pl 41 of 50 Listing Image for 24 Kahoea Pl 42 of 50 Listing Image for 24 Kahoea Pl 43 of 50 Listing Image for 24 Kahoea Pl 44 of 50 Listing Image for 24 Kahoea Pl 45 of 50 Listing Image for 24 Kahoea Pl 46 of 50 Listing Image for 24 Kahoea Pl 47 of 50 Listing Image for 24 Kahoea Pl 48 of 50 Listing Image for 24 Kahoea Pl 49 of 50 Listing Image for 24 Kahoea Pl 50 of 50

$1,250,000

Kula Highlands

24 Kahoea Pl, Kula/Ulupalakua/Kanaio

3 Beds 3 Baths 1,792 SqFt Residential MLS® # 409184 Date Sold: June 18, 2026
Sold
Closed: 05/28/2026
Listing Image for 1987 Kahekili Hwy 1 of 44 Listing Image for 1987 Kahekili Hwy 2 of 44 Listing Image for 1987 Kahekili Hwy 3 of 44 Listing Image for 1987 Kahekili Hwy 4 of 44 Listing Image for 1987 Kahekili Hwy 5 of 44 Listing Image for 1987 Kahekili Hwy 6 of 44 Listing Image for 1987 Kahekili Hwy 7 of 44 Listing Image for 1987 Kahekili Hwy 8 of 44 Listing Image for 1987 Kahekili Hwy 9 of 44 Listing Image for 1987 Kahekili Hwy 10 of 44 Listing Image for 1987 Kahekili Hwy 11 of 44 Listing Image for 1987 Kahekili Hwy 12 of 44 Listing Image for 1987 Kahekili Hwy 13 of 44 Listing Image for 1987 Kahekili Hwy 14 of 44 Listing Image for 1987 Kahekili Hwy 15 of 44 Listing Image for 1987 Kahekili Hwy 16 of 44 Listing Image for 1987 Kahekili Hwy 17 of 44 Listing Image for 1987 Kahekili Hwy 18 of 44 Listing Image for 1987 Kahekili Hwy 19 of 44 Listing Image for 1987 Kahekili Hwy 20 of 44 Listing Image for 1987 Kahekili Hwy 21 of 44 Listing Image for 1987 Kahekili Hwy 22 of 44 Listing Image for 1987 Kahekili Hwy 23 of 44 Listing Image for 1987 Kahekili Hwy 24 of 44 Listing Image for 1987 Kahekili Hwy 25 of 44 Listing Image for 1987 Kahekili Hwy 26 of 44 Listing Image for 1987 Kahekili Hwy 27 of 44 Listing Image for 1987 Kahekili Hwy 28 of 44 Listing Image for 1987 Kahekili Hwy 29 of 44 Listing Image for 1987 Kahekili Hwy 30 of 44 Listing Image for 1987 Kahekili Hwy 31 of 44 Listing Image for 1987 Kahekili Hwy 32 of 44 Listing Image for 1987 Kahekili Hwy 33 of 44 Listing Image for 1987 Kahekili Hwy 34 of 44 Listing Image for 1987 Kahekili Hwy 35 of 44 Listing Image for 1987 Kahekili Hwy 36 of 44 Listing Image for 1987 Kahekili Hwy 37 of 44 Listing Image for 1987 Kahekili Hwy 38 of 44 Listing Image for 1987 Kahekili Hwy 39 of 44 Listing Image for 1987 Kahekili Hwy 40 of 44 Listing Image for 1987 Kahekili Hwy 41 of 44 Listing Image for 1987 Kahekili Hwy 42 of 44 Listing Image for 1987 Kahekili Hwy 43 of 44 Listing Image for 1987 Kahekili Hwy 44 of 44

$885,000

Waihee Village

1987 Kahekili Hwy, Wailuku

3 Beds 2.5 Baths 1,100 SqFt Residential MLS® # 409180 Date Sold: May 28, 2026
Sold
Closed: 07/30/2026
Listing Image for 34 Kulalani Cir 1 of 49 Listing Image for 34 Kulalani Cir 2 of 49 Listing Image for 34 Kulalani Cir 3 of 49 Listing Image for 34 Kulalani Cir 4 of 49 Listing Image for 34 Kulalani Cir 5 of 49 Listing Image for 34 Kulalani Cir 6 of 49 Listing Image for 34 Kulalani Cir 7 of 49 Listing Image for 34 Kulalani Cir 8 of 49 Listing Image for 34 Kulalani Cir 9 of 49 Listing Image for 34 Kulalani Cir 10 of 49 Listing Image for 34 Kulalani Cir 11 of 49 Listing Image for 34 Kulalani Cir 12 of 49 Listing Image for 34 Kulalani Cir 13 of 49 Listing Image for 34 Kulalani Cir 14 of 49 Listing Image for 34 Kulalani Cir 15 of 49 Listing Image for 34 Kulalani Cir 16 of 49 Listing Image for 34 Kulalani Cir 17 of 49 Listing Image for 34 Kulalani Cir 18 of 49 Listing Image for 34 Kulalani Cir 19 of 49 Listing Image for 34 Kulalani Cir 20 of 49 Listing Image for 34 Kulalani Cir 21 of 49 Listing Image for 34 Kulalani Cir 22 of 49 Listing Image for 34 Kulalani Cir 23 of 49 Listing Image for 34 Kulalani Cir 24 of 49 Listing Image for 34 Kulalani Cir 25 of 49 Listing Image for 34 Kulalani Cir 26 of 49 Listing Image for 34 Kulalani Cir 27 of 49 Listing Image for 34 Kulalani Cir 28 of 49 Listing Image for 34 Kulalani Cir 29 of 49 Listing Image for 34 Kulalani Cir 30 of 49 Listing Image for 34 Kulalani Cir 31 of 49 Listing Image for 34 Kulalani Cir 32 of 49 Listing Image for 34 Kulalani Cir 33 of 49 Listing Image for 34 Kulalani Cir 34 of 49 Listing Image for 34 Kulalani Cir 35 of 49 Listing Image for 34 Kulalani Cir 36 of 49 Listing Image for 34 Kulalani Cir 37 of 49 Listing Image for 34 Kulalani Cir 38 of 49 Listing Image for 34 Kulalani Cir 39 of 49 Listing Image for 34 Kulalani Cir 40 of 49 Listing Image for 34 Kulalani Cir 41 of 49 Listing Image for 34 Kulalani Cir 42 of 49 Listing Image for 34 Kulalani Cir 43 of 49 Listing Image for 34 Kulalani Cir 44 of 49 Listing Image for 34 Kulalani Cir 45 of 49 Listing Image for 34 Kulalani Cir 46 of 49 Listing Image for 34 Kulalani Cir 47 of 49 Listing Image for 34 Kulalani Cir 48 of 49 Listing Image for 34 Kulalani Cir 49 of 49

$1,280,000

↓ $119,000

Kula Orchards

34 Kulalani Cir, Kula/Ulupalakua/Kanaio

4 Beds 3 Baths 2,054 SqFt Residential MLS® # 409179 Date Sold: July 30, 2026
Sold
Closed: 04/07/2026
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$850,000

Kapalua Ridge 723

100 Ridge Rd 723, Kapalua

1 Bed 2 Baths 1,150 SqFt Residential MLS® # 403548 Date Sold: April 7, 2026
Sold
Closed: 07/02/2026
Listing Image for 126 Kulalani Dr 1 of 50 Listing Image for 126 Kulalani Dr 2 of 50 Listing Image for 126 Kulalani Dr 3 of 50 Listing Image for 126 Kulalani Dr 4 of 50 Listing Image for 126 Kulalani Dr 5 of 50 Listing Image for 126 Kulalani Dr 6 of 50 Listing Image for 126 Kulalani Dr 7 of 50 Listing Image for 126 Kulalani Dr 8 of 50 Listing Image for 126 Kulalani Dr 9 of 50 Listing Image for 126 Kulalani Dr 10 of 50 Listing Image for 126 Kulalani Dr 11 of 50 Listing Image for 126 Kulalani Dr 12 of 50 Listing Image for 126 Kulalani Dr 13 of 50 Listing Image for 126 Kulalani Dr 14 of 50 Listing Image for 126 Kulalani Dr 15 of 50 Listing Image for 126 Kulalani Dr 16 of 50 Listing Image for 126 Kulalani Dr 17 of 50 Listing Image for 126 Kulalani Dr 18 of 50 Listing Image for 126 Kulalani Dr 19 of 50 Listing Image for 126 Kulalani Dr 20 of 50 Listing Image for 126 Kulalani Dr 21 of 50 Listing Image for 126 Kulalani Dr 22 of 50 Listing Image for 126 Kulalani Dr 23 of 50 Listing Image for 126 Kulalani Dr 24 of 50 Listing Image for 126 Kulalani Dr 25 of 50 Listing Image for 126 Kulalani Dr 26 of 50 Listing Image for 126 Kulalani Dr 27 of 50 Listing Image for 126 Kulalani Dr 28 of 50 Listing Image for 126 Kulalani Dr 29 of 50 Listing Image for 126 Kulalani Dr 30 of 50 Listing Image for 126 Kulalani Dr 31 of 50 Listing Image for 126 Kulalani Dr 32 of 50 Listing Image for 126 Kulalani Dr 33 of 50 Listing Image for 126 Kulalani Dr 34 of 50 Listing Image for 126 Kulalani Dr 35 of 50 Listing Image for 126 Kulalani Dr 36 of 50 Listing Image for 126 Kulalani Dr 37 of 50 Listing Image for 126 Kulalani Dr 38 of 50 Listing Image for 126 Kulalani Dr 39 of 50 Listing Image for 126 Kulalani Dr 40 of 50 Listing Image for 126 Kulalani Dr 41 of 50 Listing Image for 126 Kulalani Dr 42 of 50 Listing Image for 126 Kulalani Dr 43 of 50 Listing Image for 126 Kulalani Dr 44 of 50 Listing Image for 126 Kulalani Dr 45 of 50 Listing Image for 126 Kulalani Dr 46 of 50 Listing Image for 126 Kulalani Dr 47 of 50 Listing Image for 126 Kulalani Dr 48 of 50 Listing Image for 126 Kulalani Dr 49 of 50 Listing Image for 126 Kulalani Dr 50 of 50

$1,350,000

↓ $238,000

Kula Ekahi

126 Kulalani Dr, Kula/Ulupalakua/Kanaio

4 Beds 3 Baths 2,304 SqFt Residential MLS® # 409169 Date Sold: July 2, 2026
Sold
Closed: 07/29/2026
Listing Image for 50 Nohea Kai Dr Iv-205 1 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 2 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 3 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 4 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 5 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 6 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 7 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 8 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 9 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 10 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 11 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 12 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 13 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 14 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 15 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 16 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 17 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 18 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 19 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 20 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 21 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 22 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 23 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 24 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 25 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 26 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 27 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 28 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 29 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 30 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 31 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 32 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 33 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 34 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 35 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 36 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 37 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 38 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 39 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 40 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 41 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 42 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 43 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 44 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 45 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 46 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 47 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 48 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 49 of 50 Listing Image for 50 Nohea Kai Dr Iv-205 50 of 50

$1,905,000

↓ $394,000

Kaanapali Alii IV-205

50 Nohea Kai Dr Iv-205, Kaanapali

2 Beds 2 Baths 1,669 SqFt Residential MLS® # 409162 Date Sold: July 29, 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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