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 130 Kai Malina Pkwy Nr314 1 of 19 Listing Image for 130 Kai Malina Pkwy Nr314 2 of 19 Listing Image for 130 Kai Malina Pkwy Nr314 3 of 19 Listing Image for 130 Kai Malina Pkwy Nr314 4 of 19 Listing Image for 130 Kai Malina Pkwy Nr314 5 of 19 Listing Image for 130 Kai Malina Pkwy Nr314 6 of 19 Listing Image for 130 Kai Malina Pkwy Nr314 7 of 19 Listing Image for 130 Kai Malina Pkwy Nr314 8 of 19 Listing Image for 130 Kai Malina Pkwy Nr314 9 of 19 Listing Image for 130 Kai Malina Pkwy Nr314 10 of 19 Listing Image for 130 Kai Malina Pkwy Nr314 11 of 19 Listing Image for 130 Kai Malina Pkwy Nr314 12 of 19 Listing Image for 130 Kai Malina Pkwy Nr314 13 of 19 Listing Image for 130 Kai Malina Pkwy Nr314 14 of 19 Listing Image for 130 Kai Malina Pkwy Nr314 15 of 19 Listing Image for 130 Kai Malina Pkwy Nr314 16 of 19 Listing Image for 130 Kai Malina Pkwy Nr314 17 of 19 Listing Image for 130 Kai Malina Pkwy Nr314 18 of 19 Listing Image for 130 Kai Malina Pkwy Nr314 19 of 19

$1,299,000

Honua Kai - Konea NR314

130 Kai Malina Pkwy Nr314, Kaanapali

1 Bed 1 Bath 690 SqFt Residential MLS® # 409343

Days on Market: 149

Maui Westside Properties

Short Term Rental
Listing Image for 25-1 Puakukui Pl 25-1 1 of 24 Listing Image for 25-1 Puakukui Pl 25-1 2 of 24 Listing Image for 25-1 Puakukui Pl 25-1 3 of 24 Listing Image for 25-1 Puakukui Pl 25-1 4 of 24 Listing Image for 25-1 Puakukui Pl 25-1 5 of 24 Listing Image for 25-1 Puakukui Pl 25-1 6 of 24 Listing Image for 25-1 Puakukui Pl 25-1 7 of 24 Listing Image for 25-1 Puakukui Pl 25-1 8 of 24 Listing Image for 25-1 Puakukui Pl 25-1 9 of 24 Listing Image for 25-1 Puakukui Pl 25-1 10 of 24 Listing Image for 25-1 Puakukui Pl 25-1 11 of 24 Listing Image for 25-1 Puakukui Pl 25-1 12 of 24 Listing Image for 25-1 Puakukui Pl 25-1 13 of 24 Listing Image for 25-1 Puakukui Pl 25-1 14 of 24 Listing Image for 25-1 Puakukui Pl 25-1 15 of 24 Listing Image for 25-1 Puakukui Pl 25-1 16 of 24 Listing Image for 25-1 Puakukui Pl 25-1 17 of 24 Listing Image for 25-1 Puakukui Pl 25-1 18 of 24 Listing Image for 25-1 Puakukui Pl 25-1 19 of 24 Listing Image for 25-1 Puakukui Pl 25-1 20 of 24 Listing Image for 25-1 Puakukui Pl 25-1 21 of 24 Listing Image for 25-1 Puakukui Pl 25-1 22 of 24 Listing Image for 25-1 Puakukui Pl 25-1 23 of 24 Listing Image for 25-1 Puakukui Pl 25-1 24 of 24

$898,000

Puamana 25-1

25-1 Puakukui Pl 25-1, Lahaina

1 Bed 2 Baths 900 SqFt Residential MLS® # 409340

Days on Market: 150

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

Listing Image for 121 Kapihaa Pl 1 of 22 Listing Image for 121 Kapihaa Pl 2 of 22 Listing Image for 121 Kapihaa Pl 3 of 22 Listing Image for 121 Kapihaa Pl 4 of 22 Listing Image for 121 Kapihaa Pl 5 of 22 Listing Image for 121 Kapihaa Pl 6 of 22 Listing Image for 121 Kapihaa Pl 7 of 22 Listing Image for 121 Kapihaa Pl 8 of 22 Listing Image for 121 Kapihaa Pl 9 of 22 Listing Image for 121 Kapihaa Pl 10 of 22 Listing Image for 121 Kapihaa Pl 11 of 22 Listing Image for 121 Kapihaa Pl 12 of 22 Listing Image for 121 Kapihaa Pl 13 of 22 Listing Image for 121 Kapihaa Pl 14 of 22 Listing Image for 121 Kapihaa Pl 15 of 22 Listing Image for 121 Kapihaa Pl 16 of 22 Listing Image for 121 Kapihaa Pl 17 of 22 Listing Image for 121 Kapihaa Pl 18 of 22 Listing Image for 121 Kapihaa Pl 19 of 22 Listing Image for 121 Kapihaa Pl 20 of 22 Listing Image for 121 Kapihaa Pl 21 of 22 Listing Image for 121 Kapihaa Pl 22 of 22

$17,000,000

Lanai

121 Kapihaa Pl, Lanai

7 Beds 9 Baths 8,495 SqFt Residential MLS® # 404095

Days on Market: 662

Deep Blue HI

Listing Image for 40 Kalihi Pl 1 of 15 Listing Image for 40 Kalihi Pl 2 of 15 Listing Image for 40 Kalihi Pl 3 of 15 Listing Image for 40 Kalihi Pl 4 of 15 Listing Image for 40 Kalihi Pl 5 of 15 Listing Image for 40 Kalihi Pl 6 of 15 Listing Image for 40 Kalihi Pl 7 of 15 Listing Image for 40 Kalihi Pl 8 of 15 Listing Image for 40 Kalihi Pl 9 of 15 Listing Image for 40 Kalihi Pl 10 of 15 Listing Image for 40 Kalihi Pl 11 of 15 Listing Image for 40 Kalihi Pl 12 of 15 Listing Image for 40 Kalihi Pl 13 of 15 Listing Image for 40 Kalihi Pl 14 of 15 Listing Image for 40 Kalihi Pl 15 of 15

$1,100,000

Kula/Ulupalakua/Kanaio

40 Kalihi Pl, Kula/Ulupalakua/Kanaio

2 Beds 1 Bath 1,224 SqFt Residential MLS® # 409336

Days on Market: 151

Tri-Isle Rlty & Dev Co Inc

Listing Image for 50 Puu Anoano St 2206 1 of 50 Listing Image for 50 Puu Anoano St 2206 2 of 50 Listing Image for 50 Puu Anoano St 2206 3 of 50 Listing Image for 50 Puu Anoano St 2206 4 of 50 Listing Image for 50 Puu Anoano St 2206 5 of 50 Listing Image for 50 Puu Anoano St 2206 6 of 50 Listing Image for 50 Puu Anoano St 2206 7 of 50 Listing Image for 50 Puu Anoano St 2206 8 of 50 Listing Image for 50 Puu Anoano St 2206 9 of 50 Listing Image for 50 Puu Anoano St 2206 10 of 50 Listing Image for 50 Puu Anoano St 2206 11 of 50 Listing Image for 50 Puu Anoano St 2206 12 of 50 Listing Image for 50 Puu Anoano St 2206 13 of 50 Listing Image for 50 Puu Anoano St 2206 14 of 50 Listing Image for 50 Puu Anoano St 2206 15 of 50 Listing Image for 50 Puu Anoano St 2206 16 of 50 Listing Image for 50 Puu Anoano St 2206 17 of 50 Listing Image for 50 Puu Anoano St 2206 18 of 50 Listing Image for 50 Puu Anoano St 2206 19 of 50 Listing Image for 50 Puu Anoano St 2206 20 of 50 Listing Image for 50 Puu Anoano St 2206 21 of 50 Listing Image for 50 Puu Anoano St 2206 22 of 50 Listing Image for 50 Puu Anoano St 2206 23 of 50 Listing Image for 50 Puu Anoano St 2206 24 of 50 Listing Image for 50 Puu Anoano St 2206 25 of 50 Listing Image for 50 Puu Anoano St 2206 26 of 50 Listing Image for 50 Puu Anoano St 2206 27 of 50 Listing Image for 50 Puu Anoano St 2206 28 of 50 Listing Image for 50 Puu Anoano St 2206 29 of 50 Listing Image for 50 Puu Anoano St 2206 30 of 50 Listing Image for 50 Puu Anoano St 2206 31 of 50 Listing Image for 50 Puu Anoano St 2206 32 of 50 Listing Image for 50 Puu Anoano St 2206 33 of 50 Listing Image for 50 Puu Anoano St 2206 34 of 50 Listing Image for 50 Puu Anoano St 2206 35 of 50 Listing Image for 50 Puu Anoano St 2206 36 of 50 Listing Image for 50 Puu Anoano St 2206 37 of 50 Listing Image for 50 Puu Anoano St 2206 38 of 50 Listing Image for 50 Puu Anoano St 2206 39 of 50 Listing Image for 50 Puu Anoano St 2206 40 of 50 Listing Image for 50 Puu Anoano St 2206 41 of 50 Listing Image for 50 Puu Anoano St 2206 42 of 50 Listing Image for 50 Puu Anoano St 2206 43 of 50 Listing Image for 50 Puu Anoano St 2206 44 of 50 Listing Image for 50 Puu Anoano St 2206 45 of 50 Listing Image for 50 Puu Anoano St 2206 46 of 50 Listing Image for 50 Puu Anoano St 2206 47 of 50 Listing Image for 50 Puu Anoano St 2206 48 of 50 Listing Image for 50 Puu Anoano St 2206 49 of 50 Listing Image for 50 Puu Anoano St 2206 50 of 50

$1,300,000

Masters 2206

50 Puu Anoano St 2206, Kaanapali

2 Beds 2 Baths 1,728 SqFt Residential MLS® # 409327

Days on Market: 152

Coldwell Banker Island Prop-KP Cell: 808-283-3067

Short Term Rental
Listing Image for 3543 Lower Honoapiilani Rd J105 1 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 2 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 3 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 4 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 5 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 6 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 7 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 8 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 9 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 10 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 11 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 12 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 13 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 14 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 15 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 16 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 17 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 18 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 19 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 20 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 21 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 22 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 23 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 24 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 25 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 26 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 27 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 28 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 29 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 30 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 31 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 32 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 33 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 34 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 35 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 36 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 37 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 38 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 39 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 40 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 41 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 42 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 43 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 44 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 45 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 46 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 47 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 48 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 49 of 50 Listing Image for 3543 Lower Honoapiilani Rd J105 50 of 50

$998,000

Papakea Resort J105

3543 Lower Honoapiilani Rd J105, Napili/Kahana/Honokowai

2 Beds 2 Baths 907 SqFt Residential MLS® # 409328

Days on Market: 152

Coldwell Banker Island Prop-KP Cell: 808-283-3067

Listing Image for 61 Kee Rd 1 of 50 Listing Image for 61 Kee Rd 2 of 50 Listing Image for 61 Kee Rd 3 of 50 Listing Image for 61 Kee Rd 4 of 50 Listing Image for 61 Kee Rd 5 of 50 Listing Image for 61 Kee Rd 6 of 50 Listing Image for 61 Kee Rd 7 of 50 Listing Image for 61 Kee Rd 8 of 50 Listing Image for 61 Kee Rd 9 of 50 Listing Image for 61 Kee Rd 10 of 50 Listing Image for 61 Kee Rd 11 of 50 Listing Image for 61 Kee Rd 12 of 50 Listing Image for 61 Kee Rd 13 of 50 Listing Image for 61 Kee Rd 14 of 50 Listing Image for 61 Kee Rd 15 of 50 Listing Image for 61 Kee Rd 16 of 50 Listing Image for 61 Kee Rd 17 of 50 Listing Image for 61 Kee Rd 18 of 50 Listing Image for 61 Kee Rd 19 of 50 Listing Image for 61 Kee Rd 20 of 50 Listing Image for 61 Kee Rd 21 of 50 Listing Image for 61 Kee Rd 22 of 50 Listing Image for 61 Kee Rd 23 of 50 Listing Image for 61 Kee Rd 24 of 50 Listing Image for 61 Kee Rd 25 of 50 Listing Image for 61 Kee Rd 26 of 50 Listing Image for 61 Kee Rd 27 of 50 Listing Image for 61 Kee Rd 28 of 50 Listing Image for 61 Kee Rd 29 of 50 Listing Image for 61 Kee Rd 30 of 50 Listing Image for 61 Kee Rd 31 of 50 Listing Image for 61 Kee Rd 32 of 50 Listing Image for 61 Kee Rd 33 of 50 Listing Image for 61 Kee Rd 34 of 50 Listing Image for 61 Kee Rd 35 of 50 Listing Image for 61 Kee Rd 36 of 50 Listing Image for 61 Kee Rd 37 of 50 Listing Image for 61 Kee Rd 38 of 50 Listing Image for 61 Kee Rd 39 of 50 Listing Image for 61 Kee Rd 40 of 50 Listing Image for 61 Kee Rd 41 of 50 Listing Image for 61 Kee Rd 42 of 50 Listing Image for 61 Kee Rd 43 of 50 Listing Image for 61 Kee Rd 44 of 50 Listing Image for 61 Kee Rd 45 of 50 Listing Image for 61 Kee Rd 46 of 50 Listing Image for 61 Kee Rd 47 of 50 Listing Image for 61 Kee Rd 48 of 50 Listing Image for 61 Kee Rd 49 of 50 Listing Image for 61 Kee Rd 50 of 50

$3,400,000

Haleakala Ranch Homestead

61 Kee Rd, Makawao/Olinda/Haliimaile

4 Beds 3 Baths 2,914 SqFt Residential MLS® # 409325

Days on Market: 151

Equity One Real Estate Inc (M) Cell: 808-276-3244

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Apply for a Home Equity Loan

While you may ideally want to sell your current house before buying a new one, this may not be an absolute requirement for some sellers. You could tap into your home’s equity by applying for an equity line of credit. Before moving forward with this possibility, be aware that the payment on the new home equity line will affect your debt-to-income ratio.

Mortgage lenders review your debt-to-income ratio as part of their qualification process. Because of this, you should discuss this option in detail with your lender to ensure that it will not impair your ability to qualify for a new mortgage.

Recent Sales on Maui

Sold
Closed: 02/27/2026
Listing Image for 4000 Wailea Alanui Dr 603 1 of 19 Listing Image for 4000 Wailea Alanui Dr 603 2 of 19 Listing Image for 4000 Wailea Alanui Dr 603 3 of 19 Listing Image for 4000 Wailea Alanui Dr 603 4 of 19 Listing Image for 4000 Wailea Alanui Dr 603 5 of 19 Listing Image for 4000 Wailea Alanui Dr 603 6 of 19 Listing Image for 4000 Wailea Alanui Dr 603 7 of 19 Listing Image for 4000 Wailea Alanui Dr 603 8 of 19 Listing Image for 4000 Wailea Alanui Dr 603 9 of 19 Listing Image for 4000 Wailea Alanui Dr 603 10 of 19 Listing Image for 4000 Wailea Alanui Dr 603 11 of 19 Listing Image for 4000 Wailea Alanui Dr 603 12 of 19 Listing Image for 4000 Wailea Alanui Dr 603 13 of 19 Listing Image for 4000 Wailea Alanui Dr 603 14 of 19 Listing Image for 4000 Wailea Alanui Dr 603 15 of 19 Listing Image for 4000 Wailea Alanui Dr 603 16 of 19 Listing Image for 4000 Wailea Alanui Dr 603 17 of 19 Listing Image for 4000 Wailea Alanui Dr 603 18 of 19 Listing Image for 4000 Wailea Alanui Dr 603 19 of 19

$5,750,000

Wailea Point 603

4000 Wailea Alanui Dr 603, Wailea/Makena

2 Beds 2 Baths 1,900 SqFt Residential MLS® # 408065 Date Sold: February 27, 2026
Sold
Closed: 02/18/2026
Listing Image for 1139 Kauhikoa Rd A 1 of 42 Listing Image for 1139 Kauhikoa Rd A 2 of 42 Listing Image for 1139 Kauhikoa Rd A 3 of 42 Listing Image for 1139 Kauhikoa Rd A 4 of 42 Listing Image for 1139 Kauhikoa Rd A 5 of 42 Listing Image for 1139 Kauhikoa Rd A 6 of 42 Listing Image for 1139 Kauhikoa Rd A 7 of 42 Listing Image for 1139 Kauhikoa Rd A 8 of 42 Listing Image for 1139 Kauhikoa Rd A 9 of 42 Listing Image for 1139 Kauhikoa Rd A 10 of 42 Listing Image for 1139 Kauhikoa Rd A 11 of 42 Listing Image for 1139 Kauhikoa Rd A 12 of 42 Listing Image for 1139 Kauhikoa Rd A 13 of 42 Listing Image for 1139 Kauhikoa Rd A 14 of 42 Listing Image for 1139 Kauhikoa Rd A 15 of 42 Listing Image for 1139 Kauhikoa Rd A 16 of 42 Listing Image for 1139 Kauhikoa Rd A 17 of 42 Listing Image for 1139 Kauhikoa Rd A 18 of 42 Listing Image for 1139 Kauhikoa Rd A 19 of 42 Listing Image for 1139 Kauhikoa Rd A 20 of 42 Listing Image for 1139 Kauhikoa Rd A 21 of 42 Listing Image for 1139 Kauhikoa Rd A 22 of 42 Listing Image for 1139 Kauhikoa Rd A 23 of 42 Listing Image for 1139 Kauhikoa Rd A 24 of 42 Listing Image for 1139 Kauhikoa Rd A 25 of 42 Listing Image for 1139 Kauhikoa Rd A 26 of 42 Listing Image for 1139 Kauhikoa Rd A 27 of 42 Listing Image for 1139 Kauhikoa Rd A 28 of 42 Listing Image for 1139 Kauhikoa Rd A 29 of 42 Listing Image for 1139 Kauhikoa Rd A 30 of 42 Listing Image for 1139 Kauhikoa Rd A 31 of 42 Listing Image for 1139 Kauhikoa Rd A 32 of 42 Listing Image for 1139 Kauhikoa Rd A 33 of 42 Listing Image for 1139 Kauhikoa Rd A 34 of 42 Listing Image for 1139 Kauhikoa Rd A 35 of 42 Listing Image for 1139 Kauhikoa Rd A 36 of 42 Listing Image for 1139 Kauhikoa Rd A 37 of 42 Listing Image for 1139 Kauhikoa Rd A 38 of 42 Listing Image for 1139 Kauhikoa Rd A 39 of 42 Listing Image for 1139 Kauhikoa Rd A 40 of 42 Listing Image for 1139 Kauhikoa Rd A 41 of 42 Listing Image for 1139 Kauhikoa Rd A 42 of 42

$1,399,000

Haiku

1139 Kauhikoa Rd A, Haiku

3 Beds 2 Baths 1,400 SqFt Residential MLS® # 408063 Date Sold: February 18, 2026
Sold
Closed: 01/23/2026
Listing Image for 123 Punakea Loop Unit A 1 of 29 Listing Image for 123 Punakea Loop Unit A 2 of 29 Listing Image for 123 Punakea Loop Unit A 3 of 29 Listing Image for 123 Punakea Loop Unit A 4 of 29 Listing Image for 123 Punakea Loop Unit A 5 of 29 Listing Image for 123 Punakea Loop Unit A 6 of 29 Listing Image for 123 Punakea Loop Unit A 7 of 29 Listing Image for 123 Punakea Loop Unit A 8 of 29 Listing Image for 123 Punakea Loop Unit A 9 of 29 Listing Image for 123 Punakea Loop Unit A 10 of 29 Listing Image for 123 Punakea Loop Unit A 11 of 29 Listing Image for 123 Punakea Loop Unit A 12 of 29 Listing Image for 123 Punakea Loop Unit A 13 of 29 Listing Image for 123 Punakea Loop Unit A 14 of 29 Listing Image for 123 Punakea Loop Unit A 15 of 29 Listing Image for 123 Punakea Loop Unit A 16 of 29 Listing Image for 123 Punakea Loop Unit A 17 of 29 Listing Image for 123 Punakea Loop Unit A 18 of 29 Listing Image for 123 Punakea Loop Unit A 19 of 29 Listing Image for 123 Punakea Loop Unit A 20 of 29 Listing Image for 123 Punakea Loop Unit A 21 of 29 Listing Image for 123 Punakea Loop Unit A 22 of 29 Listing Image for 123 Punakea Loop Unit A 23 of 29 Listing Image for 123 Punakea Loop Unit A 24 of 29 Listing Image for 123 Punakea Loop Unit A 25 of 29 Listing Image for 123 Punakea Loop Unit A 26 of 29 Listing Image for 123 Punakea Loop Unit A 27 of 29 Listing Image for 123 Punakea Loop Unit A 28 of 29 Listing Image for 123 Punakea Loop Unit A 29 of 29

$3,549,000

Makila Plantation

123 Punakea Loop Unit A, Lahaina

2 Beds 3 Baths 1,000 SqFt Residential MLS® # 408061 Date Sold: January 23, 2026
Sold
Closed: 01/28/2026
Listing Image for 467 Anapuni Loop 1 of 50 Listing Image for 467 Anapuni Loop 2 of 50 Listing Image for 467 Anapuni Loop 3 of 50 Listing Image for 467 Anapuni Loop 4 of 50 Listing Image for 467 Anapuni Loop 5 of 50 Listing Image for 467 Anapuni Loop 6 of 50 Listing Image for 467 Anapuni Loop 7 of 50 Listing Image for 467 Anapuni Loop 8 of 50 Listing Image for 467 Anapuni Loop 9 of 50 Listing Image for 467 Anapuni Loop 10 of 50 Listing Image for 467 Anapuni Loop 11 of 50 Listing Image for 467 Anapuni Loop 12 of 50 Listing Image for 467 Anapuni Loop 13 of 50 Listing Image for 467 Anapuni Loop 14 of 50 Listing Image for 467 Anapuni Loop 15 of 50 Listing Image for 467 Anapuni Loop 16 of 50 Listing Image for 467 Anapuni Loop 17 of 50 Listing Image for 467 Anapuni Loop 18 of 50 Listing Image for 467 Anapuni Loop 19 of 50 Listing Image for 467 Anapuni Loop 20 of 50 Listing Image for 467 Anapuni Loop 21 of 50 Listing Image for 467 Anapuni Loop 22 of 50 Listing Image for 467 Anapuni Loop 23 of 50 Listing Image for 467 Anapuni Loop 24 of 50 Listing Image for 467 Anapuni Loop 25 of 50 Listing Image for 467 Anapuni Loop 26 of 50 Listing Image for 467 Anapuni Loop 27 of 50 Listing Image for 467 Anapuni Loop 28 of 50 Listing Image for 467 Anapuni Loop 29 of 50 Listing Image for 467 Anapuni Loop 30 of 50 Listing Image for 467 Anapuni Loop 31 of 50 Listing Image for 467 Anapuni Loop 32 of 50 Listing Image for 467 Anapuni Loop 33 of 50 Listing Image for 467 Anapuni Loop 34 of 50 Listing Image for 467 Anapuni Loop 35 of 50 Listing Image for 467 Anapuni Loop 36 of 50 Listing Image for 467 Anapuni Loop 37 of 50 Listing Image for 467 Anapuni Loop 38 of 50 Listing Image for 467 Anapuni Loop 39 of 50 Listing Image for 467 Anapuni Loop 40 of 50 Listing Image for 467 Anapuni Loop 41 of 50 Listing Image for 467 Anapuni Loop 42 of 50 Listing Image for 467 Anapuni Loop 43 of 50 Listing Image for 467 Anapuni Loop 44 of 50 Listing Image for 467 Anapuni Loop 45 of 50 Listing Image for 467 Anapuni Loop 46 of 50 Listing Image for 467 Anapuni Loop 47 of 50 Listing Image for 467 Anapuni Loop 48 of 50 Listing Image for 467 Anapuni Loop 49 of 50 Listing Image for 467 Anapuni Loop 50 of 50

$5,500,000

Lanikeha

467 Anapuni Loop, Kaanapali

4 Beds 5 Baths 3,846 SqFt Residential MLS® # 408049 Date Sold: January 28, 2026
Sold
Closed: 02/25/2026
Listing Image for 137 Hoohale St 1 of 42 Listing Image for 137 Hoohale St 2 of 42 Listing Image for 137 Hoohale St 3 of 42 Listing Image for 137 Hoohale St 4 of 42 Listing Image for 137 Hoohale St 5 of 42 Listing Image for 137 Hoohale St 6 of 42 Listing Image for 137 Hoohale St 7 of 42 Listing Image for 137 Hoohale St 8 of 42 Listing Image for 137 Hoohale St 9 of 42 Listing Image for 137 Hoohale St 10 of 42 Listing Image for 137 Hoohale St 11 of 42 Listing Image for 137 Hoohale St 12 of 42 Listing Image for 137 Hoohale St 13 of 42 Listing Image for 137 Hoohale St 14 of 42 Listing Image for 137 Hoohale St 15 of 42 Listing Image for 137 Hoohale St 16 of 42 Listing Image for 137 Hoohale St 17 of 42 Listing Image for 137 Hoohale St 18 of 42 Listing Image for 137 Hoohale St 19 of 42 Listing Image for 137 Hoohale St 20 of 42 Listing Image for 137 Hoohale St 21 of 42 Listing Image for 137 Hoohale St 22 of 42 Listing Image for 137 Hoohale St 23 of 42 Listing Image for 137 Hoohale St 24 of 42 Listing Image for 137 Hoohale St 25 of 42 Listing Image for 137 Hoohale St 26 of 42 Listing Image for 137 Hoohale St 27 of 42 Listing Image for 137 Hoohale St 28 of 42 Listing Image for 137 Hoohale St 29 of 42 Listing Image for 137 Hoohale St 30 of 42 Listing Image for 137 Hoohale St 31 of 42 Listing Image for 137 Hoohale St 32 of 42 Listing Image for 137 Hoohale St 33 of 42 Listing Image for 137 Hoohale St 34 of 42 Listing Image for 137 Hoohale St 35 of 42 Listing Image for 137 Hoohale St 36 of 42 Listing Image for 137 Hoohale St 37 of 42 Listing Image for 137 Hoohale St 38 of 42 Listing Image for 137 Hoohale St 39 of 42 Listing Image for 137 Hoohale St 40 of 42 Listing Image for 137 Hoohale St 41 of 42 Listing Image for 137 Hoohale St 42 of 42

$2,400,000

Kilohana Mauka

137 Hoohale St, Kihei

4 Beds 4 Baths 2,490 SqFt Residential MLS® # 408044 Date Sold: February 25, 2026
Sold
Closed: 02/11/2026
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$1,530,000

Omaopio Homesteads

2846 Omaopio Rd, Kula/Ulupalakua/Kanaio

2 Beds 2 Baths 1,270 SqFt Residential MLS® # 408043 Date Sold: February 11, 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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