Strategies of Buying and Selling Simultaneously

Buying and Selling a Home at the Same Time

You may have found yourself in a position where you would like to buy one property while simultaneously selling another property. While doing this does present some unique challenges, it's completely possible to pull this off with the proper strategy and some degree of flexibility

The reasons and strategies for wanting to buy and sell simultaneously will differ from a primary homeowner looking to relocate to an investor seeking to execute a 1031 exchange to avoid capital gains taxes. In either instance, it's important to have a sound strategy and understand what the undertaking will involve. 

Selling A Primary Residence While Buying Another

There are several different ways to do this and how you do it will depend on your financial philosophies. There isn't necessarily a right and wrong way to approach this, some consider selling their home first the priority and then are willing to rent for a period of 6 months while they find the perfect replacement. This is usually the lowest stress avenue.

Some will be intent on executing the sale and purchase in such a way that both properties close in close succession to remove the extra step of renting. Money is a huge consideration for this move, particularly when financing is involved. In many instances, sellers will need the equity from the sale of their home to fund the down payment on the purchase of the second. 

If Financing is Necessary, Get Prequalified for a New Mortgage First

Before you get serious about selling your home, you should thoroughly research the possibility of buying a new primary residence. The Maui housing market can change rapidly at times, and the lending environment is changing as well. When you get prequalified with a local Maui lender, you can better determine your price range for a new home.

You can get accurate information about the interest rates available for your credit score and other qualifications. In addition, you can confirm that you can afford the loan payment for the size and quality of the home you are interested in.

Discuss Your Plans with a Real Estate Agent

After learning about your prequalification status, consulting with real estate agents in Maui is the next step. An experienced Maui real estate agent can help you determine how long your home may reasonably remain on the market.

In addition, you can get details on a realistic sales price. By analyzing the sales price in combination with closing costs and the current mortgage payoff balance, you can determine the sales proceeds that you have available for a down payment on your new home purchase. 

Newest Maui Properties For Sale

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Short Term Rental
Listing Image for 106 Kaanapali Shores Pl 801 1 of 20 Listing Image for 106 Kaanapali Shores Pl 801 2 of 20 Listing Image for 106 Kaanapali Shores Pl 801 3 of 20 Listing Image for 106 Kaanapali Shores Pl 801 4 of 20 Listing Image for 106 Kaanapali Shores Pl 801 5 of 20 Listing Image for 106 Kaanapali Shores Pl 801 6 of 20 Listing Image for 106 Kaanapali Shores Pl 801 7 of 20 Listing Image for 106 Kaanapali Shores Pl 801 8 of 20 Listing Image for 106 Kaanapali Shores Pl 801 9 of 20 Listing Image for 106 Kaanapali Shores Pl 801 10 of 20 Listing Image for 106 Kaanapali Shores Pl 801 11 of 20 Listing Image for 106 Kaanapali Shores Pl 801 12 of 20 Listing Image for 106 Kaanapali Shores Pl 801 13 of 20 Listing Image for 106 Kaanapali Shores Pl 801 14 of 20 Listing Image for 106 Kaanapali Shores Pl 801 15 of 20 Listing Image for 106 Kaanapali Shores Pl 801 16 of 20 Listing Image for 106 Kaanapali Shores Pl 801 17 of 20 Listing Image for 106 Kaanapali Shores Pl 801 18 of 20 Listing Image for 106 Kaanapali Shores Pl 801 19 of 20 Listing Image for 106 Kaanapali Shores Pl 801 20 of 20

$899,000

↓ $76,000

Maui Kai 801

106 Kaanapali Shores Pl 801, Kaanapali

1 Bed 1 Bath 587 SqFt Residential MLS® # 410036

Days on Market: 84

Keller Williams Realty Maui-L Cell: 808-250-5073

Listing Image for 50 Puu Anoano St 1602 1 of 50 Listing Image for 50 Puu Anoano St 1602 2 of 50 Listing Image for 50 Puu Anoano St 1602 3 of 50 Listing Image for 50 Puu Anoano St 1602 4 of 50 Listing Image for 50 Puu Anoano St 1602 5 of 50 Listing Image for 50 Puu Anoano St 1602 6 of 50 Listing Image for 50 Puu Anoano St 1602 7 of 50 Listing Image for 50 Puu Anoano St 1602 8 of 50 Listing Image for 50 Puu Anoano St 1602 9 of 50 Listing Image for 50 Puu Anoano St 1602 10 of 50 Listing Image for 50 Puu Anoano St 1602 11 of 50 Listing Image for 50 Puu Anoano St 1602 12 of 50 Listing Image for 50 Puu Anoano St 1602 13 of 50 Listing Image for 50 Puu Anoano St 1602 14 of 50 Listing Image for 50 Puu Anoano St 1602 15 of 50 Listing Image for 50 Puu Anoano St 1602 16 of 50 Listing Image for 50 Puu Anoano St 1602 17 of 50 Listing Image for 50 Puu Anoano St 1602 18 of 50 Listing Image for 50 Puu Anoano St 1602 19 of 50 Listing Image for 50 Puu Anoano St 1602 20 of 50 Listing Image for 50 Puu Anoano St 1602 21 of 50 Listing Image for 50 Puu Anoano St 1602 22 of 50 Listing Image for 50 Puu Anoano St 1602 23 of 50 Listing Image for 50 Puu Anoano St 1602 24 of 50 Listing Image for 50 Puu Anoano St 1602 25 of 50 Listing Image for 50 Puu Anoano St 1602 26 of 50 Listing Image for 50 Puu Anoano St 1602 27 of 50 Listing Image for 50 Puu Anoano St 1602 28 of 50 Listing Image for 50 Puu Anoano St 1602 29 of 50 Listing Image for 50 Puu Anoano St 1602 30 of 50 Listing Image for 50 Puu Anoano St 1602 31 of 50 Listing Image for 50 Puu Anoano St 1602 32 of 50 Listing Image for 50 Puu Anoano St 1602 33 of 50 Listing Image for 50 Puu Anoano St 1602 34 of 50 Listing Image for 50 Puu Anoano St 1602 35 of 50 Listing Image for 50 Puu Anoano St 1602 36 of 50 Listing Image for 50 Puu Anoano St 1602 37 of 50 Listing Image for 50 Puu Anoano St 1602 38 of 50 Listing Image for 50 Puu Anoano St 1602 39 of 50 Listing Image for 50 Puu Anoano St 1602 40 of 50 Listing Image for 50 Puu Anoano St 1602 41 of 50 Listing Image for 50 Puu Anoano St 1602 42 of 50 Listing Image for 50 Puu Anoano St 1602 43 of 50 Listing Image for 50 Puu Anoano St 1602 44 of 50 Listing Image for 50 Puu Anoano St 1602 45 of 50 Listing Image for 50 Puu Anoano St 1602 46 of 50 Listing Image for 50 Puu Anoano St 1602 47 of 50 Listing Image for 50 Puu Anoano St 1602 48 of 50 Listing Image for 50 Puu Anoano St 1602 49 of 50 Listing Image for 50 Puu Anoano St 1602 50 of 50

$1,895,000

Masters 1602

50 Puu Anoano St 1602, Kaanapali

2 Beds 2 Baths 1,544 SqFt Residential MLS® # 410033

Days on Market: 84

Compass Cell: 808-757-8053

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

$2,690,000

↓ $190,000

Peahi Hui

10 Leleaka Pl, Haiku

4 Beds 2.5 Baths 3,576 SqFt Residential MLS® # 410015

Days on Market: 86

Century 21 Island Homes

In Escrow
Listing Image for 169 Waipalani Rd 1 of 50 Listing Image for 169 Waipalani Rd 2 of 50 Listing Image for 169 Waipalani Rd 3 of 50 Listing Image for 169 Waipalani Rd 4 of 50 Listing Image for 169 Waipalani Rd 5 of 50 Listing Image for 169 Waipalani Rd 6 of 50 Listing Image for 169 Waipalani Rd 7 of 50 Listing Image for 169 Waipalani Rd 8 of 50 Listing Image for 169 Waipalani Rd 9 of 50 Listing Image for 169 Waipalani Rd 10 of 50 Listing Image for 169 Waipalani Rd 11 of 50 Listing Image for 169 Waipalani Rd 12 of 50 Listing Image for 169 Waipalani Rd 13 of 50 Listing Image for 169 Waipalani Rd 14 of 50 Listing Image for 169 Waipalani Rd 15 of 50 Listing Image for 169 Waipalani Rd 16 of 50 Listing Image for 169 Waipalani Rd 17 of 50 Listing Image for 169 Waipalani Rd 18 of 50 Listing Image for 169 Waipalani Rd 19 of 50 Listing Image for 169 Waipalani Rd 20 of 50 Listing Image for 169 Waipalani Rd 21 of 50 Listing Image for 169 Waipalani Rd 22 of 50 Listing Image for 169 Waipalani Rd 23 of 50 Listing Image for 169 Waipalani Rd 24 of 50 Listing Image for 169 Waipalani Rd 25 of 50 Listing Image for 169 Waipalani Rd 26 of 50 Listing Image for 169 Waipalani Rd 27 of 50 Listing Image for 169 Waipalani Rd 28 of 50 Listing Image for 169 Waipalani Rd 29 of 50 Listing Image for 169 Waipalani Rd 30 of 50 Listing Image for 169 Waipalani Rd 31 of 50 Listing Image for 169 Waipalani Rd 32 of 50 Listing Image for 169 Waipalani Rd 33 of 50 Listing Image for 169 Waipalani Rd 34 of 50 Listing Image for 169 Waipalani Rd 35 of 50 Listing Image for 169 Waipalani Rd 36 of 50 Listing Image for 169 Waipalani Rd 37 of 50 Listing Image for 169 Waipalani Rd 38 of 50 Listing Image for 169 Waipalani Rd 39 of 50 Listing Image for 169 Waipalani Rd 40 of 50 Listing Image for 169 Waipalani Rd 41 of 50 Listing Image for 169 Waipalani Rd 42 of 50 Listing Image for 169 Waipalani Rd 43 of 50 Listing Image for 169 Waipalani Rd 44 of 50 Listing Image for 169 Waipalani Rd 45 of 50 Listing Image for 169 Waipalani Rd 46 of 50 Listing Image for 169 Waipalani Rd 47 of 50 Listing Image for 169 Waipalani Rd 48 of 50 Listing Image for 169 Waipalani Rd 49 of 50 Listing Image for 169 Waipalani Rd 50 of 50

$1,649,000

Peahi

169 Waipalani Rd, Haiku

3 Beds 2 Baths 1,440 SqFt Residential MLS® # 410013

Days on Market: 88

REMAX Hawaii Maui

Listing Image for 147 Moana Ave Unit 39 1 of 45 Listing Image for 147 Moana Ave Unit 39 2 of 45 Listing Image for 147 Moana Ave Unit 39 3 of 45 Listing Image for 147 Moana Ave Unit 39 4 of 45 Listing Image for 147 Moana Ave Unit 39 5 of 45 Listing Image for 147 Moana Ave Unit 39 6 of 45 Listing Image for 147 Moana Ave Unit 39 7 of 45 Listing Image for 147 Moana Ave Unit 39 8 of 45 Listing Image for 147 Moana Ave Unit 39 9 of 45 Listing Image for 147 Moana Ave Unit 39 10 of 45 Listing Image for 147 Moana Ave Unit 39 11 of 45 Listing Image for 147 Moana Ave Unit 39 12 of 45 Listing Image for 147 Moana Ave Unit 39 13 of 45 Listing Image for 147 Moana Ave Unit 39 14 of 45 Listing Image for 147 Moana Ave Unit 39 15 of 45 Listing Image for 147 Moana Ave Unit 39 16 of 45 Listing Image for 147 Moana Ave Unit 39 17 of 45 Listing Image for 147 Moana Ave Unit 39 18 of 45 Listing Image for 147 Moana Ave Unit 39 19 of 45 Listing Image for 147 Moana Ave Unit 39 20 of 45 Listing Image for 147 Moana Ave Unit 39 21 of 45 Listing Image for 147 Moana Ave Unit 39 22 of 45 Listing Image for 147 Moana Ave Unit 39 23 of 45 Listing Image for 147 Moana Ave Unit 39 24 of 45 Listing Image for 147 Moana Ave Unit 39 25 of 45 Listing Image for 147 Moana Ave Unit 39 26 of 45 Listing Image for 147 Moana Ave Unit 39 27 of 45 Listing Image for 147 Moana Ave Unit 39 28 of 45 Listing Image for 147 Moana Ave Unit 39 29 of 45 Listing Image for 147 Moana Ave Unit 39 30 of 45 Listing Image for 147 Moana Ave Unit 39 31 of 45 Listing Image for 147 Moana Ave Unit 39 32 of 45 Listing Image for 147 Moana Ave Unit 39 33 of 45 Listing Image for 147 Moana Ave Unit 39 34 of 45 Listing Image for 147 Moana Ave Unit 39 35 of 45 Listing Image for 147 Moana Ave Unit 39 36 of 45 Listing Image for 147 Moana Ave Unit 39 37 of 45 Listing Image for 147 Moana Ave Unit 39 38 of 45 Listing Image for 147 Moana Ave Unit 39 39 of 45 Listing Image for 147 Moana Ave Unit 39 40 of 45 Listing Image for 147 Moana Ave Unit 39 41 of 45 Listing Image for 147 Moana Ave Unit 39 42 of 45 Listing Image for 147 Moana Ave Unit 39 43 of 45 Listing Image for 147 Moana Ave Unit 39 44 of 45 Listing Image for 147 Moana Ave Unit 39 45 of 45

$2,100,000

Moana Estates Subd

147 Moana Ave Unit 39, Kihei

4 Beds 3.5 Baths 2,168 SqFt Residential MLS® # 410011

Days on Market: 87

Coldwell Banker Island Prop-Ku Cell: 808-283-6696

Listing Image for 180 Door Of Faith Rd 1 of 50 Listing Image for 180 Door Of Faith Rd 2 of 50 Listing Image for 180 Door Of Faith Rd 3 of 50 Listing Image for 180 Door Of Faith Rd 4 of 50 Listing Image for 180 Door Of Faith Rd 5 of 50 Listing Image for 180 Door Of Faith Rd 6 of 50 Listing Image for 180 Door Of Faith Rd 7 of 50 Listing Image for 180 Door Of Faith Rd 8 of 50 Listing Image for 180 Door Of Faith Rd 9 of 50 Listing Image for 180 Door Of Faith Rd 10 of 50 Listing Image for 180 Door Of Faith Rd 11 of 50 Listing Image for 180 Door Of Faith Rd 12 of 50 Listing Image for 180 Door Of Faith Rd 13 of 50 Listing Image for 180 Door Of Faith Rd 14 of 50 Listing Image for 180 Door Of Faith Rd 15 of 50 Listing Image for 180 Door Of Faith Rd 16 of 50 Listing Image for 180 Door Of Faith Rd 17 of 50 Listing Image for 180 Door Of Faith Rd 18 of 50 Listing Image for 180 Door Of Faith Rd 19 of 50 Listing Image for 180 Door Of Faith Rd 20 of 50 Listing Image for 180 Door Of Faith Rd 21 of 50 Listing Image for 180 Door Of Faith Rd 22 of 50 Listing Image for 180 Door Of Faith Rd 23 of 50 Listing Image for 180 Door Of Faith Rd 24 of 50 Listing Image for 180 Door Of Faith Rd 25 of 50 Listing Image for 180 Door Of Faith Rd 26 of 50 Listing Image for 180 Door Of Faith Rd 27 of 50 Listing Image for 180 Door Of Faith Rd 28 of 50 Listing Image for 180 Door Of Faith Rd 29 of 50 Listing Image for 180 Door Of Faith Rd 30 of 50 Listing Image for 180 Door Of Faith Rd 31 of 50 Listing Image for 180 Door Of Faith Rd 32 of 50 Listing Image for 180 Door Of Faith Rd 33 of 50 Listing Image for 180 Door Of Faith Rd 34 of 50 Listing Image for 180 Door Of Faith Rd 35 of 50 Listing Image for 180 Door Of Faith Rd 36 of 50 Listing Image for 180 Door Of Faith Rd 37 of 50 Listing Image for 180 Door Of Faith Rd 38 of 50 Listing Image for 180 Door Of Faith Rd 39 of 50 Listing Image for 180 Door Of Faith Rd 40 of 50 Listing Image for 180 Door Of Faith Rd 41 of 50 Listing Image for 180 Door Of Faith Rd 42 of 50 Listing Image for 180 Door Of Faith Rd 43 of 50 Listing Image for 180 Door Of Faith Rd 44 of 50 Listing Image for 180 Door Of Faith Rd 45 of 50 Listing Image for 180 Door Of Faith Rd 46 of 50 Listing Image for 180 Door Of Faith Rd 47 of 50 Listing Image for 180 Door Of Faith Rd 48 of 50 Listing Image for 180 Door Of Faith Rd 49 of 50 Listing Image for 180 Door Of Faith Rd 50 of 50

$7,450,000

↓ $250,000

Haiku

180 Door Of Faith Rd, Haiku

3 Beds 2 Baths 3,609 SqFt Residential MLS® # 408161

Days on Market: 270

eXp Realty Cell: 808-222-0478

Short Term Rental
Listing Image for 130 Kai Malina Pkwy Sr613 1 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 2 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 3 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 4 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 5 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 6 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 7 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 8 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 9 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 10 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 11 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 12 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 13 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 14 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 15 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 16 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 17 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 18 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 19 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 20 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 21 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 22 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 23 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 24 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 25 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 26 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 27 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 28 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 29 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 30 of 31 Listing Image for 130 Kai Malina Pkwy Sr613 31 of 31

$1,599,000

↓ $26,000

Honua Kai - Hoku Lani SR613

130 Kai Malina Pkwy Sr613, Kaanapali

1 Bed 1 Bath 700 SqFt Residential MLS® # 410006

Days on Market: 87

Coldwell Banker Island Prop-KP Cell: 808-446-5841

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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: 04/30/2026
Listing Image for 2174 Aluna Pl 1 of 50 Listing Image for 2174 Aluna Pl 2 of 50 Listing Image for 2174 Aluna Pl 3 of 50 Listing Image for 2174 Aluna Pl 4 of 50 Listing Image for 2174 Aluna Pl 5 of 50 Listing Image for 2174 Aluna Pl 6 of 50 Listing Image for 2174 Aluna Pl 7 of 50 Listing Image for 2174 Aluna Pl 8 of 50 Listing Image for 2174 Aluna Pl 9 of 50 Listing Image for 2174 Aluna Pl 10 of 50 Listing Image for 2174 Aluna Pl 11 of 50 Listing Image for 2174 Aluna Pl 12 of 50 Listing Image for 2174 Aluna Pl 13 of 50 Listing Image for 2174 Aluna Pl 14 of 50 Listing Image for 2174 Aluna Pl 15 of 50 Listing Image for 2174 Aluna Pl 16 of 50 Listing Image for 2174 Aluna Pl 17 of 50 Listing Image for 2174 Aluna Pl 18 of 50 Listing Image for 2174 Aluna Pl 19 of 50 Listing Image for 2174 Aluna Pl 20 of 50 Listing Image for 2174 Aluna Pl 21 of 50 Listing Image for 2174 Aluna Pl 22 of 50 Listing Image for 2174 Aluna Pl 23 of 50 Listing Image for 2174 Aluna Pl 24 of 50 Listing Image for 2174 Aluna Pl 25 of 50 Listing Image for 2174 Aluna Pl 26 of 50 Listing Image for 2174 Aluna Pl 27 of 50 Listing Image for 2174 Aluna Pl 28 of 50 Listing Image for 2174 Aluna Pl 29 of 50 Listing Image for 2174 Aluna Pl 30 of 50 Listing Image for 2174 Aluna Pl 31 of 50 Listing Image for 2174 Aluna Pl 32 of 50 Listing Image for 2174 Aluna Pl 33 of 50 Listing Image for 2174 Aluna Pl 34 of 50 Listing Image for 2174 Aluna Pl 35 of 50 Listing Image for 2174 Aluna Pl 36 of 50 Listing Image for 2174 Aluna Pl 37 of 50 Listing Image for 2174 Aluna Pl 38 of 50 Listing Image for 2174 Aluna Pl 39 of 50 Listing Image for 2174 Aluna Pl 40 of 50 Listing Image for 2174 Aluna Pl 41 of 50 Listing Image for 2174 Aluna Pl 42 of 50 Listing Image for 2174 Aluna Pl 43 of 50 Listing Image for 2174 Aluna Pl 44 of 50 Listing Image for 2174 Aluna Pl 45 of 50 Listing Image for 2174 Aluna Pl 46 of 50 Listing Image for 2174 Aluna Pl 47 of 50 Listing Image for 2174 Aluna Pl 48 of 50 Listing Image for 2174 Aluna Pl 49 of 50 Listing Image for 2174 Aluna Pl 50 of 50

$1,530,000

Hale Lakau

2174 Aluna Pl, Kihei

4 Beds 3 Baths 2,324 SqFt Residential MLS® # 408733 Date Sold: April 30, 2026
Sold
Closed: 03/27/2026
Listing Image for 39 & 33 Hakui Loop 1 of 50 Listing Image for 39 & 33 Hakui Loop 2 of 50 Listing Image for 39 & 33 Hakui Loop 3 of 50 Listing Image for 39 & 33 Hakui Loop 4 of 50 Listing Image for 39 & 33 Hakui Loop 5 of 50 Listing Image for 39 & 33 Hakui Loop 6 of 50 Listing Image for 39 & 33 Hakui Loop 7 of 50 Listing Image for 39 & 33 Hakui Loop 8 of 50 Listing Image for 39 & 33 Hakui Loop 9 of 50 Listing Image for 39 & 33 Hakui Loop 10 of 50 Listing Image for 39 & 33 Hakui Loop 11 of 50 Listing Image for 39 & 33 Hakui Loop 12 of 50 Listing Image for 39 & 33 Hakui Loop 13 of 50 Listing Image for 39 & 33 Hakui Loop 14 of 50 Listing Image for 39 & 33 Hakui Loop 15 of 50 Listing Image for 39 & 33 Hakui Loop 16 of 50 Listing Image for 39 & 33 Hakui Loop 17 of 50 Listing Image for 39 & 33 Hakui Loop 18 of 50 Listing Image for 39 & 33 Hakui Loop 19 of 50 Listing Image for 39 & 33 Hakui Loop 20 of 50 Listing Image for 39 & 33 Hakui Loop 21 of 50 Listing Image for 39 & 33 Hakui Loop 22 of 50 Listing Image for 39 & 33 Hakui Loop 23 of 50 Listing Image for 39 & 33 Hakui Loop 24 of 50 Listing Image for 39 & 33 Hakui Loop 25 of 50 Listing Image for 39 & 33 Hakui Loop 26 of 50 Listing Image for 39 & 33 Hakui Loop 27 of 50 Listing Image for 39 & 33 Hakui Loop 28 of 50 Listing Image for 39 & 33 Hakui Loop 29 of 50 Listing Image for 39 & 33 Hakui Loop 30 of 50 Listing Image for 39 & 33 Hakui Loop 31 of 50 Listing Image for 39 & 33 Hakui Loop 32 of 50 Listing Image for 39 & 33 Hakui Loop 33 of 50 Listing Image for 39 & 33 Hakui Loop 34 of 50 Listing Image for 39 & 33 Hakui Loop 35 of 50 Listing Image for 39 & 33 Hakui Loop 36 of 50 Listing Image for 39 & 33 Hakui Loop 37 of 50 Listing Image for 39 & 33 Hakui Loop 38 of 50 Listing Image for 39 & 33 Hakui Loop 39 of 50 Listing Image for 39 & 33 Hakui Loop 40 of 50 Listing Image for 39 & 33 Hakui Loop 41 of 50 Listing Image for 39 & 33 Hakui Loop 42 of 50 Listing Image for 39 & 33 Hakui Loop 43 of 50 Listing Image for 39 & 33 Hakui Loop 44 of 50 Listing Image for 39 & 33 Hakui Loop 45 of 50 Listing Image for 39 & 33 Hakui Loop 46 of 50 Listing Image for 39 & 33 Hakui Loop 47 of 50 Listing Image for 39 & 33 Hakui Loop 48 of 50 Listing Image for 39 & 33 Hakui Loop 49 of 50 Listing Image for 39 & 33 Hakui Loop 50 of 50

$3,050,000

Kaanapali Hillside

39 & 33 Hakui Loop, Kaanapali

4 Beds 3.5 Baths 3,785 SqFt Residential MLS® # 408731 Date Sold: March 27, 2026
Sold
Closed: 02/11/2026
Listing Image for 3100 Wailea Alanui Dr 12 1 of 50 Listing Image for 3100 Wailea Alanui Dr 12 2 of 50 Listing Image for 3100 Wailea Alanui Dr 12 3 of 50 Listing Image for 3100 Wailea Alanui Dr 12 4 of 50 Listing Image for 3100 Wailea Alanui Dr 12 5 of 50 Listing Image for 3100 Wailea Alanui Dr 12 6 of 50 Listing Image for 3100 Wailea Alanui Dr 12 7 of 50 Listing Image for 3100 Wailea Alanui Dr 12 8 of 50 Listing Image for 3100 Wailea Alanui Dr 12 9 of 50 Listing Image for 3100 Wailea Alanui Dr 12 10 of 50 Listing Image for 3100 Wailea Alanui Dr 12 11 of 50 Listing Image for 3100 Wailea Alanui Dr 12 12 of 50 Listing Image for 3100 Wailea Alanui Dr 12 13 of 50 Listing Image for 3100 Wailea Alanui Dr 12 14 of 50 Listing Image for 3100 Wailea Alanui Dr 12 15 of 50 Listing Image for 3100 Wailea Alanui Dr 12 16 of 50 Listing Image for 3100 Wailea Alanui Dr 12 17 of 50 Listing Image for 3100 Wailea Alanui Dr 12 18 of 50 Listing Image for 3100 Wailea Alanui Dr 12 19 of 50 Listing Image for 3100 Wailea Alanui Dr 12 20 of 50 Listing Image for 3100 Wailea Alanui Dr 12 21 of 50 Listing Image for 3100 Wailea Alanui Dr 12 22 of 50 Listing Image for 3100 Wailea Alanui Dr 12 23 of 50 Listing Image for 3100 Wailea Alanui Dr 12 24 of 50 Listing Image for 3100 Wailea Alanui Dr 12 25 of 50 Listing Image for 3100 Wailea Alanui Dr 12 26 of 50 Listing Image for 3100 Wailea Alanui Dr 12 27 of 50 Listing Image for 3100 Wailea Alanui Dr 12 28 of 50 Listing Image for 3100 Wailea Alanui Dr 12 29 of 50 Listing Image for 3100 Wailea Alanui Dr 12 30 of 50 Listing Image for 3100 Wailea Alanui Dr 12 31 of 50 Listing Image for 3100 Wailea Alanui Dr 12 32 of 50 Listing Image for 3100 Wailea Alanui Dr 12 33 of 50 Listing Image for 3100 Wailea Alanui Dr 12 34 of 50 Listing Image for 3100 Wailea Alanui Dr 12 35 of 50 Listing Image for 3100 Wailea Alanui Dr 12 36 of 50 Listing Image for 3100 Wailea Alanui Dr 12 37 of 50 Listing Image for 3100 Wailea Alanui Dr 12 38 of 50 Listing Image for 3100 Wailea Alanui Dr 12 39 of 50 Listing Image for 3100 Wailea Alanui Dr 12 40 of 50 Listing Image for 3100 Wailea Alanui Dr 12 41 of 50 Listing Image for 3100 Wailea Alanui Dr 12 42 of 50 Listing Image for 3100 Wailea Alanui Dr 12 43 of 50 Listing Image for 3100 Wailea Alanui Dr 12 44 of 50 Listing Image for 3100 Wailea Alanui Dr 12 45 of 50 Listing Image for 3100 Wailea Alanui Dr 12 46 of 50 Listing Image for 3100 Wailea Alanui Dr 12 47 of 50 Listing Image for 3100 Wailea Alanui Dr 12 48 of 50 Listing Image for 3100 Wailea Alanui Dr 12 49 of 50 Listing Image for 3100 Wailea Alanui Dr 12 50 of 50

$4,500,000

Papali Wailea 12

3100 Wailea Alanui Dr 12, Wailea/Makena

3 Beds 3.5 Baths 2,386 SqFt Residential MLS® # 408715 Date Sold: February 11, 2026
Sold
Closed: 08/20/2026
Listing Image for 11 Halapa Pl 1 of 50 Listing Image for 11 Halapa Pl 2 of 50 Listing Image for 11 Halapa Pl 3 of 50 Listing Image for 11 Halapa Pl 4 of 50 Listing Image for 11 Halapa Pl 5 of 50 Listing Image for 11 Halapa Pl 6 of 50 Listing Image for 11 Halapa Pl 7 of 50 Listing Image for 11 Halapa Pl 8 of 50 Listing Image for 11 Halapa Pl 9 of 50 Listing Image for 11 Halapa Pl 10 of 50 Listing Image for 11 Halapa Pl 11 of 50 Listing Image for 11 Halapa Pl 12 of 50 Listing Image for 11 Halapa Pl 13 of 50 Listing Image for 11 Halapa Pl 14 of 50 Listing Image for 11 Halapa Pl 15 of 50 Listing Image for 11 Halapa Pl 16 of 50 Listing Image for 11 Halapa Pl 17 of 50 Listing Image for 11 Halapa Pl 18 of 50 Listing Image for 11 Halapa Pl 19 of 50 Listing Image for 11 Halapa Pl 20 of 50 Listing Image for 11 Halapa Pl 21 of 50 Listing Image for 11 Halapa Pl 22 of 50 Listing Image for 11 Halapa Pl 23 of 50 Listing Image for 11 Halapa Pl 24 of 50 Listing Image for 11 Halapa Pl 25 of 50 Listing Image for 11 Halapa Pl 26 of 50 Listing Image for 11 Halapa Pl 27 of 50 Listing Image for 11 Halapa Pl 28 of 50 Listing Image for 11 Halapa Pl 29 of 50 Listing Image for 11 Halapa Pl 30 of 50 Listing Image for 11 Halapa Pl 31 of 50 Listing Image for 11 Halapa Pl 32 of 50 Listing Image for 11 Halapa Pl 33 of 50 Listing Image for 11 Halapa Pl 34 of 50 Listing Image for 11 Halapa Pl 35 of 50 Listing Image for 11 Halapa Pl 36 of 50 Listing Image for 11 Halapa Pl 37 of 50 Listing Image for 11 Halapa Pl 38 of 50 Listing Image for 11 Halapa Pl 39 of 50 Listing Image for 11 Halapa Pl 40 of 50 Listing Image for 11 Halapa Pl 41 of 50 Listing Image for 11 Halapa Pl 42 of 50 Listing Image for 11 Halapa Pl 43 of 50 Listing Image for 11 Halapa Pl 44 of 50 Listing Image for 11 Halapa Pl 45 of 50 Listing Image for 11 Halapa Pl 46 of 50 Listing Image for 11 Halapa Pl 47 of 50 Listing Image for 11 Halapa Pl 48 of 50 Listing Image for 11 Halapa Pl 49 of 50 Listing Image for 11 Halapa Pl 50 of 50

$8,300,000

↓ $1,680,000

The Ridge at Wailea

11 Halapa Pl, Wailea/Makena

5 Beds 4.5 Baths 5,708 SqFt Residential MLS® # 408708 Date Sold: August 20, 2026
Sold
Closed: 03/30/2026
Listing Image for 50 Puu Anoano St 3408 1 of 45 Listing Image for 50 Puu Anoano St 3408 2 of 45 Listing Image for 50 Puu Anoano St 3408 3 of 45 Listing Image for 50 Puu Anoano St 3408 4 of 45 Listing Image for 50 Puu Anoano St 3408 5 of 45 Listing Image for 50 Puu Anoano St 3408 6 of 45 Listing Image for 50 Puu Anoano St 3408 7 of 45 Listing Image for 50 Puu Anoano St 3408 8 of 45 Listing Image for 50 Puu Anoano St 3408 9 of 45 Listing Image for 50 Puu Anoano St 3408 10 of 45 Listing Image for 50 Puu Anoano St 3408 11 of 45 Listing Image for 50 Puu Anoano St 3408 12 of 45 Listing Image for 50 Puu Anoano St 3408 13 of 45 Listing Image for 50 Puu Anoano St 3408 14 of 45 Listing Image for 50 Puu Anoano St 3408 15 of 45 Listing Image for 50 Puu Anoano St 3408 16 of 45 Listing Image for 50 Puu Anoano St 3408 17 of 45 Listing Image for 50 Puu Anoano St 3408 18 of 45 Listing Image for 50 Puu Anoano St 3408 19 of 45 Listing Image for 50 Puu Anoano St 3408 20 of 45 Listing Image for 50 Puu Anoano St 3408 21 of 45 Listing Image for 50 Puu Anoano St 3408 22 of 45 Listing Image for 50 Puu Anoano St 3408 23 of 45 Listing Image for 50 Puu Anoano St 3408 24 of 45 Listing Image for 50 Puu Anoano St 3408 25 of 45 Listing Image for 50 Puu Anoano St 3408 26 of 45 Listing Image for 50 Puu Anoano St 3408 27 of 45 Listing Image for 50 Puu Anoano St 3408 28 of 45 Listing Image for 50 Puu Anoano St 3408 29 of 45 Listing Image for 50 Puu Anoano St 3408 30 of 45 Listing Image for 50 Puu Anoano St 3408 31 of 45 Listing Image for 50 Puu Anoano St 3408 32 of 45 Listing Image for 50 Puu Anoano St 3408 33 of 45 Listing Image for 50 Puu Anoano St 3408 34 of 45 Listing Image for 50 Puu Anoano St 3408 35 of 45 Listing Image for 50 Puu Anoano St 3408 36 of 45 Listing Image for 50 Puu Anoano St 3408 37 of 45 Listing Image for 50 Puu Anoano St 3408 38 of 45 Listing Image for 50 Puu Anoano St 3408 39 of 45 Listing Image for 50 Puu Anoano St 3408 40 of 45 Listing Image for 50 Puu Anoano St 3408 41 of 45 Listing Image for 50 Puu Anoano St 3408 42 of 45 Listing Image for 50 Puu Anoano St 3408 43 of 45 Listing Image for 50 Puu Anoano St 3408 44 of 45 Listing Image for 50 Puu Anoano St 3408 45 of 45

$1,495,000

Masters 3408

50 Puu Anoano St 3408, Kaanapali

3 Beds 2 Baths 1,269 SqFt Residential MLS® # 408702 Date Sold: March 30, 2026
Sold
Closed: 09/03/2026
Listing Image for 244 Holomoana Way 17b 1 of 48 Listing Image for 244 Holomoana Way 17b 2 of 48 Listing Image for 244 Holomoana Way 17b 3 of 48 Listing Image for 244 Holomoana Way 17b 4 of 48 Listing Image for 244 Holomoana Way 17b 5 of 48 Listing Image for 244 Holomoana Way 17b 6 of 48 Listing Image for 244 Holomoana Way 17b 7 of 48 Listing Image for 244 Holomoana Way 17b 8 of 48 Listing Image for 244 Holomoana Way 17b 9 of 48 Listing Image for 244 Holomoana Way 17b 10 of 48 Listing Image for 244 Holomoana Way 17b 11 of 48 Listing Image for 244 Holomoana Way 17b 12 of 48 Listing Image for 244 Holomoana Way 17b 13 of 48 Listing Image for 244 Holomoana Way 17b 14 of 48 Listing Image for 244 Holomoana Way 17b 15 of 48 Listing Image for 244 Holomoana Way 17b 16 of 48 Listing Image for 244 Holomoana Way 17b 17 of 48 Listing Image for 244 Holomoana Way 17b 18 of 48 Listing Image for 244 Holomoana Way 17b 19 of 48 Listing Image for 244 Holomoana Way 17b 20 of 48 Listing Image for 244 Holomoana Way 17b 21 of 48 Listing Image for 244 Holomoana Way 17b 22 of 48 Listing Image for 244 Holomoana Way 17b 23 of 48 Listing Image for 244 Holomoana Way 17b 24 of 48 Listing Image for 244 Holomoana Way 17b 25 of 48 Listing Image for 244 Holomoana Way 17b 26 of 48 Listing Image for 244 Holomoana Way 17b 27 of 48 Listing Image for 244 Holomoana Way 17b 28 of 48 Listing Image for 244 Holomoana Way 17b 29 of 48 Listing Image for 244 Holomoana Way 17b 30 of 48 Listing Image for 244 Holomoana Way 17b 31 of 48 Listing Image for 244 Holomoana Way 17b 32 of 48 Listing Image for 244 Holomoana Way 17b 33 of 48 Listing Image for 244 Holomoana Way 17b 34 of 48 Listing Image for 244 Holomoana Way 17b 35 of 48 Listing Image for 244 Holomoana Way 17b 36 of 48 Listing Image for 244 Holomoana Way 17b 37 of 48 Listing Image for 244 Holomoana Way 17b 38 of 48 Listing Image for 244 Holomoana Way 17b 39 of 48 Listing Image for 244 Holomoana Way 17b 40 of 48 Listing Image for 244 Holomoana Way 17b 41 of 48 Listing Image for 244 Holomoana Way 17b 42 of 48 Listing Image for 244 Holomoana Way 17b 43 of 48 Listing Image for 244 Holomoana Way 17b 44 of 48 Listing Image for 244 Holomoana Way 17b 45 of 48 Listing Image for 244 Holomoana Way 17b 46 of 48 Listing Image for 244 Holomoana Way 17b 47 of 48 Listing Image for 244 Holomoana Way 17b 48 of 48

$3,050,000

↓ $445,000

Makalii at Wailea 17B

244 Holomoana Way 17b, Wailea/Makena

3 Beds 3 Baths 1,802 SqFt Residential MLS® # 408701 Date Sold: September 3, 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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