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 130 Kai Malina Pkwy Nr104 1 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 2 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 3 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 4 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 5 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 6 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 7 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 8 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 9 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 10 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 11 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 12 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 13 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 14 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 15 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 16 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 17 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 18 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 19 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 20 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 21 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 22 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 23 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 24 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 25 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 26 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 27 of 28 Listing Image for 130 Kai Malina Pkwy Nr104 28 of 28

$2,499,000

Honua Kai - Konea NR104

130 Kai Malina Pkwy Nr104, Kaanapali

2 Beds 2 Baths 1,250 SqFt Residential MLS® # 407710

Days on Market: 309

Susan Jackson Real Estate Cell: 865-206-1234

Short Term Rental
Listing Image for 130 Kai Malina Pkwy Sr 424 1 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 2 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 3 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 4 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 5 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 6 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 7 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 8 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 9 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 10 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 11 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 12 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 13 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 14 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 15 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 16 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 17 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 18 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 19 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 20 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 21 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 22 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 23 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 24 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 25 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 26 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 27 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 28 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 29 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 30 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 31 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 32 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 33 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 34 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 35 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 36 of 37 Listing Image for 130 Kai Malina Pkwy Sr 424 37 of 37

$1,099,000

Honua Kai - Hoku Lani SR 424

130 Kai Malina Pkwy Sr 424, Kaanapali

1 Bed 1 Bath 620 SqFt Residential MLS® # 407703

Days on Market: 310

Hawaii Life (KAP) Cell: 808-205-3995

Listing Image for 2839 Iwalani St 1 of 19 Listing Image for 2839 Iwalani St 2 of 19 Listing Image for 2839 Iwalani St 3 of 19 Listing Image for 2839 Iwalani St 4 of 19 Listing Image for 2839 Iwalani St 5 of 19 Listing Image for 2839 Iwalani St 6 of 19 Listing Image for 2839 Iwalani St 7 of 19 Listing Image for 2839 Iwalani St 8 of 19 Listing Image for 2839 Iwalani St 9 of 19 Listing Image for 2839 Iwalani St 10 of 19 Listing Image for 2839 Iwalani St 11 of 19 Listing Image for 2839 Iwalani St 12 of 19 Listing Image for 2839 Iwalani St 13 of 19 Listing Image for 2839 Iwalani St 14 of 19 Listing Image for 2839 Iwalani St 15 of 19 Listing Image for 2839 Iwalani St 16 of 19 Listing Image for 2839 Iwalani St 17 of 19 Listing Image for 2839 Iwalani St 18 of 19 Listing Image for 2839 Iwalani St 19 of 19

$1,188,888

↓ $91,112

Pukalani

2839 Iwalani St, Pukalani

4 Beds 3 Baths 1,732 SqFt Residential MLS® # 407702

Days on Market: 310

HomeSmart Island Homes

In Escrow
Listing Image for 81 Kumano Dr 1 of 48 Listing Image for 81 Kumano Dr 2 of 48 Listing Image for 81 Kumano Dr 3 of 48 Listing Image for 81 Kumano Dr 4 of 48 Listing Image for 81 Kumano Dr 5 of 48 Listing Image for 81 Kumano Dr 6 of 48 Listing Image for 81 Kumano Dr 7 of 48 Listing Image for 81 Kumano Dr 8 of 48 Listing Image for 81 Kumano Dr 9 of 48 Listing Image for 81 Kumano Dr 10 of 48 Listing Image for 81 Kumano Dr 11 of 48 Listing Image for 81 Kumano Dr 12 of 48 Listing Image for 81 Kumano Dr 13 of 48 Listing Image for 81 Kumano Dr 14 of 48 Listing Image for 81 Kumano Dr 15 of 48 Listing Image for 81 Kumano Dr 16 of 48 Listing Image for 81 Kumano Dr 17 of 48 Listing Image for 81 Kumano Dr 18 of 48 Listing Image for 81 Kumano Dr 19 of 48 Listing Image for 81 Kumano Dr 20 of 48 Listing Image for 81 Kumano Dr 21 of 48 Listing Image for 81 Kumano Dr 22 of 48 Listing Image for 81 Kumano Dr 23 of 48 Listing Image for 81 Kumano Dr 24 of 48 Listing Image for 81 Kumano Dr 25 of 48 Listing Image for 81 Kumano Dr 26 of 48 Listing Image for 81 Kumano Dr 27 of 48 Listing Image for 81 Kumano Dr 28 of 48 Listing Image for 81 Kumano Dr 29 of 48 Listing Image for 81 Kumano Dr 30 of 48 Listing Image for 81 Kumano Dr 31 of 48 Listing Image for 81 Kumano Dr 32 of 48 Listing Image for 81 Kumano Dr 33 of 48 Listing Image for 81 Kumano Dr 34 of 48 Listing Image for 81 Kumano Dr 35 of 48 Listing Image for 81 Kumano Dr 36 of 48 Listing Image for 81 Kumano Dr 37 of 48 Listing Image for 81 Kumano Dr 38 of 48 Listing Image for 81 Kumano Dr 39 of 48 Listing Image for 81 Kumano Dr 40 of 48 Listing Image for 81 Kumano Dr 41 of 48 Listing Image for 81 Kumano Dr 42 of 48 Listing Image for 81 Kumano Dr 43 of 48 Listing Image for 81 Kumano Dr 44 of 48 Listing Image for 81 Kumano Dr 45 of 48 Listing Image for 81 Kumano Dr 46 of 48 Listing Image for 81 Kumano Dr 47 of 48 Listing Image for 81 Kumano Dr 48 of 48

$1,199,000

↓ $51,000

Pukalani

81 Kumano Dr, Pukalani

5 Beds 3 Baths 1,493 SqFt Residential MLS® # 407699

Days on Market: 310

Berkshire Hathaway Maui Prop-L Cell: 808-757-1079

Short Term Rental
Listing Image for 4000 Wailea Alanui Dr 1202/1204 1 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 2 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 3 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 4 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 5 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 6 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 7 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 8 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 9 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 10 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 11 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 12 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 13 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 14 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 15 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 16 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 17 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 18 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 19 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 20 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 21 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 22 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 23 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 24 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 25 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 26 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 27 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 28 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 29 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 30 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 31 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 32 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 33 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 34 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 35 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 36 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 37 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 38 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 39 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 40 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 41 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 42 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 43 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 44 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 45 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 46 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 47 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 48 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 49 of 50 Listing Image for 4000 Wailea Alanui Dr 1202/1204 50 of 50

$12,995,000

↓ $500,000

Wailea Point 1202/1204

4000 Wailea Alanui Dr 1202/1204, Wailea/Makena

4 Beds 6 Baths 4,273 SqFt Residential MLS® # 407692

Days on Market: 310

Maui Real Estate Advisors LLC 808-875-4444

Short Term Rental
Listing Image for 3543 Lower Honoapiilani Rd G-103 1 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 2 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 3 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 4 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 5 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 6 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 7 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 8 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 9 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 10 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 11 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 12 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 13 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 14 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 15 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 16 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 17 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 18 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 19 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 20 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 21 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 22 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 23 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 24 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 25 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 26 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 27 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 28 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 29 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 30 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 31 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 32 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 33 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 34 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 35 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 36 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 37 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 38 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 39 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 40 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 41 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 42 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 43 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 44 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 45 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 46 of 47 Listing Image for 3543 Lower Honoapiilani Rd G-103 47 of 47

$1,049,000

Papakea Resort G-103

3543 Lower Honoapiilani Rd G-103, Napili/Kahana/Honokowai

2 Beds 2 Baths 861 SqFt Residential MLS® # 407686

Days on Market: 310

Hawaii Life (W) Cell: 808-269-7841

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

$11,000,000

↓ $2,800,000

Spreckelsville/Paia/Kuau

43 Nonohe Pl, Spreckelsville/Paia/Kuau

5 Beds 5 Baths 4,493 SqFt Residential MLS® # 407684

Days on Market: 310

The Maui Real Estate Team Inc Cell: 808-283-6377

View 7 More Listings

Apply for a Home Equity Loan

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

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

Recent Sales on Maui

Sold
Closed: 11/03/2025
Listing Image for 203 Anamuli St 1 of 26 Listing Image for 203 Anamuli St 2 of 26 Listing Image for 203 Anamuli St 3 of 26 Listing Image for 203 Anamuli St 4 of 26 Listing Image for 203 Anamuli St 5 of 26 Listing Image for 203 Anamuli St 6 of 26 Listing Image for 203 Anamuli St 7 of 26 Listing Image for 203 Anamuli St 8 of 26 Listing Image for 203 Anamuli St 9 of 26 Listing Image for 203 Anamuli St 10 of 26 Listing Image for 203 Anamuli St 11 of 26 Listing Image for 203 Anamuli St 12 of 26 Listing Image for 203 Anamuli St 13 of 26 Listing Image for 203 Anamuli St 14 of 26 Listing Image for 203 Anamuli St 15 of 26 Listing Image for 203 Anamuli St 16 of 26 Listing Image for 203 Anamuli St 17 of 26 Listing Image for 203 Anamuli St 18 of 26 Listing Image for 203 Anamuli St 19 of 26 Listing Image for 203 Anamuli St 20 of 26 Listing Image for 203 Anamuli St 21 of 26 Listing Image for 203 Anamuli St 22 of 26 Listing Image for 203 Anamuli St 23 of 26 Listing Image for 203 Anamuli St 24 of 26 Listing Image for 203 Anamuli St 25 of 26 Listing Image for 203 Anamuli St 26 of 26

$1,015,000

Legends at Maui Lani

203 Anamuli St, Kahului

3 Beds 2 Baths 1,405 SqFt Residential MLS® # 407221 Date Sold: November 3, 2025
Sold
Closed: 06/18/2026
Listing Image for 2757 S Kihei Rd 804 1 of 47 Listing Image for 2757 S Kihei Rd 804 2 of 47 Listing Image for 2757 S Kihei Rd 804 3 of 47 Listing Image for 2757 S Kihei Rd 804 4 of 47 Listing Image for 2757 S Kihei Rd 804 5 of 47 Listing Image for 2757 S Kihei Rd 804 6 of 47 Listing Image for 2757 S Kihei Rd 804 7 of 47 Listing Image for 2757 S Kihei Rd 804 8 of 47 Listing Image for 2757 S Kihei Rd 804 9 of 47 Listing Image for 2757 S Kihei Rd 804 10 of 47 Listing Image for 2757 S Kihei Rd 804 11 of 47 Listing Image for 2757 S Kihei Rd 804 12 of 47 Listing Image for 2757 S Kihei Rd 804 13 of 47 Listing Image for 2757 S Kihei Rd 804 14 of 47 Listing Image for 2757 S Kihei Rd 804 15 of 47 Listing Image for 2757 S Kihei Rd 804 16 of 47 Listing Image for 2757 S Kihei Rd 804 17 of 47 Listing Image for 2757 S Kihei Rd 804 18 of 47 Listing Image for 2757 S Kihei Rd 804 19 of 47 Listing Image for 2757 S Kihei Rd 804 20 of 47 Listing Image for 2757 S Kihei Rd 804 21 of 47 Listing Image for 2757 S Kihei Rd 804 22 of 47 Listing Image for 2757 S Kihei Rd 804 23 of 47 Listing Image for 2757 S Kihei Rd 804 24 of 47 Listing Image for 2757 S Kihei Rd 804 25 of 47 Listing Image for 2757 S Kihei Rd 804 26 of 47 Listing Image for 2757 S Kihei Rd 804 27 of 47 Listing Image for 2757 S Kihei Rd 804 28 of 47 Listing Image for 2757 S Kihei Rd 804 29 of 47 Listing Image for 2757 S Kihei Rd 804 30 of 47 Listing Image for 2757 S Kihei Rd 804 31 of 47 Listing Image for 2757 S Kihei Rd 804 32 of 47 Listing Image for 2757 S Kihei Rd 804 33 of 47 Listing Image for 2757 S Kihei Rd 804 34 of 47 Listing Image for 2757 S Kihei Rd 804 35 of 47 Listing Image for 2757 S Kihei Rd 804 36 of 47 Listing Image for 2757 S Kihei Rd 804 37 of 47 Listing Image for 2757 S Kihei Rd 804 38 of 47 Listing Image for 2757 S Kihei Rd 804 39 of 47 Listing Image for 2757 S Kihei Rd 804 40 of 47 Listing Image for 2757 S Kihei Rd 804 41 of 47 Listing Image for 2757 S Kihei Rd 804 42 of 47 Listing Image for 2757 S Kihei Rd 804 43 of 47 Listing Image for 2757 S Kihei Rd 804 44 of 47 Listing Image for 2757 S Kihei Rd 804 45 of 47 Listing Image for 2757 S Kihei Rd 804 46 of 47 Listing Image for 2757 S Kihei Rd 804 47 of 47

$975,000

Paradise Ridge Estates 804

2757 S Kihei Rd 804, Kihei

2 Beds 2 Baths 1,251 SqFt Residential MLS® # 407214 Date Sold: June 18, 2026
Sold
Closed: 06/18/2026
Listing Image for 50 Puu Anoano St 2804 1 of 49 Listing Image for 50 Puu Anoano St 2804 2 of 49 Listing Image for 50 Puu Anoano St 2804 3 of 49 Listing Image for 50 Puu Anoano St 2804 4 of 49 Listing Image for 50 Puu Anoano St 2804 5 of 49 Listing Image for 50 Puu Anoano St 2804 6 of 49 Listing Image for 50 Puu Anoano St 2804 7 of 49 Listing Image for 50 Puu Anoano St 2804 8 of 49 Listing Image for 50 Puu Anoano St 2804 9 of 49 Listing Image for 50 Puu Anoano St 2804 10 of 49 Listing Image for 50 Puu Anoano St 2804 11 of 49 Listing Image for 50 Puu Anoano St 2804 12 of 49 Listing Image for 50 Puu Anoano St 2804 13 of 49 Listing Image for 50 Puu Anoano St 2804 14 of 49 Listing Image for 50 Puu Anoano St 2804 15 of 49 Listing Image for 50 Puu Anoano St 2804 16 of 49 Listing Image for 50 Puu Anoano St 2804 17 of 49 Listing Image for 50 Puu Anoano St 2804 18 of 49 Listing Image for 50 Puu Anoano St 2804 19 of 49 Listing Image for 50 Puu Anoano St 2804 20 of 49 Listing Image for 50 Puu Anoano St 2804 21 of 49 Listing Image for 50 Puu Anoano St 2804 22 of 49 Listing Image for 50 Puu Anoano St 2804 23 of 49 Listing Image for 50 Puu Anoano St 2804 24 of 49 Listing Image for 50 Puu Anoano St 2804 25 of 49 Listing Image for 50 Puu Anoano St 2804 26 of 49 Listing Image for 50 Puu Anoano St 2804 27 of 49 Listing Image for 50 Puu Anoano St 2804 28 of 49 Listing Image for 50 Puu Anoano St 2804 29 of 49 Listing Image for 50 Puu Anoano St 2804 30 of 49 Listing Image for 50 Puu Anoano St 2804 31 of 49 Listing Image for 50 Puu Anoano St 2804 32 of 49 Listing Image for 50 Puu Anoano St 2804 33 of 49 Listing Image for 50 Puu Anoano St 2804 34 of 49 Listing Image for 50 Puu Anoano St 2804 35 of 49 Listing Image for 50 Puu Anoano St 2804 36 of 49 Listing Image for 50 Puu Anoano St 2804 37 of 49 Listing Image for 50 Puu Anoano St 2804 38 of 49 Listing Image for 50 Puu Anoano St 2804 39 of 49 Listing Image for 50 Puu Anoano St 2804 40 of 49 Listing Image for 50 Puu Anoano St 2804 41 of 49 Listing Image for 50 Puu Anoano St 2804 42 of 49 Listing Image for 50 Puu Anoano St 2804 43 of 49 Listing Image for 50 Puu Anoano St 2804 44 of 49 Listing Image for 50 Puu Anoano St 2804 45 of 49 Listing Image for 50 Puu Anoano St 2804 46 of 49 Listing Image for 50 Puu Anoano St 2804 47 of 49 Listing Image for 50 Puu Anoano St 2804 48 of 49 Listing Image for 50 Puu Anoano St 2804 49 of 49

$1,620,000

↓ $130,000

Masters 2804

50 Puu Anoano St 2804, Kaanapali

2 Beds 2 Baths 1,512 SqFt Residential MLS® # 407127 Date Sold: June 18, 2026
Sold
Closed: 12/16/2025
Listing Image for 106 Kaanapali Shores Pl 805 1 of 40 Listing Image for 106 Kaanapali Shores Pl 805 2 of 40 Listing Image for 106 Kaanapali Shores Pl 805 3 of 40 Listing Image for 106 Kaanapali Shores Pl 805 4 of 40 Listing Image for 106 Kaanapali Shores Pl 805 5 of 40 Listing Image for 106 Kaanapali Shores Pl 805 6 of 40 Listing Image for 106 Kaanapali Shores Pl 805 7 of 40 Listing Image for 106 Kaanapali Shores Pl 805 8 of 40 Listing Image for 106 Kaanapali Shores Pl 805 9 of 40 Listing Image for 106 Kaanapali Shores Pl 805 10 of 40 Listing Image for 106 Kaanapali Shores Pl 805 11 of 40 Listing Image for 106 Kaanapali Shores Pl 805 12 of 40 Listing Image for 106 Kaanapali Shores Pl 805 13 of 40 Listing Image for 106 Kaanapali Shores Pl 805 14 of 40 Listing Image for 106 Kaanapali Shores Pl 805 15 of 40 Listing Image for 106 Kaanapali Shores Pl 805 16 of 40 Listing Image for 106 Kaanapali Shores Pl 805 17 of 40 Listing Image for 106 Kaanapali Shores Pl 805 18 of 40 Listing Image for 106 Kaanapali Shores Pl 805 19 of 40 Listing Image for 106 Kaanapali Shores Pl 805 20 of 40 Listing Image for 106 Kaanapali Shores Pl 805 21 of 40 Listing Image for 106 Kaanapali Shores Pl 805 22 of 40 Listing Image for 106 Kaanapali Shores Pl 805 23 of 40 Listing Image for 106 Kaanapali Shores Pl 805 24 of 40 Listing Image for 106 Kaanapali Shores Pl 805 25 of 40 Listing Image for 106 Kaanapali Shores Pl 805 26 of 40 Listing Image for 106 Kaanapali Shores Pl 805 27 of 40 Listing Image for 106 Kaanapali Shores Pl 805 28 of 40 Listing Image for 106 Kaanapali Shores Pl 805 29 of 40 Listing Image for 106 Kaanapali Shores Pl 805 30 of 40 Listing Image for 106 Kaanapali Shores Pl 805 31 of 40 Listing Image for 106 Kaanapali Shores Pl 805 32 of 40 Listing Image for 106 Kaanapali Shores Pl 805 33 of 40 Listing Image for 106 Kaanapali Shores Pl 805 34 of 40 Listing Image for 106 Kaanapali Shores Pl 805 35 of 40 Listing Image for 106 Kaanapali Shores Pl 805 36 of 40 Listing Image for 106 Kaanapali Shores Pl 805 37 of 40 Listing Image for 106 Kaanapali Shores Pl 805 38 of 40 Listing Image for 106 Kaanapali Shores Pl 805 39 of 40 Listing Image for 106 Kaanapali Shores Pl 805 40 of 40

$750,000

↓ $100,000

Maui Kai 805

106 Kaanapali Shores Pl 805, Kaanapali

1 Bed 1 Bath 647 SqFt Residential MLS® # 407134 Date Sold: December 16, 2025
Sold
Closed: 09/12/2025
1421 Nuna Pl, Wailuku

$1,130,000

Wailuku

1421 Nuna Pl, Wailuku

1 Bed 2 Baths 1,277 SqFt Residential MLS® # 407110 Date Sold: September 12, 2025
Sold
Closed: 11/07/2025
Listing Image for 50 Puu Anoano St 1501 1 of 41 Listing Image for 50 Puu Anoano St 1501 2 of 41 Listing Image for 50 Puu Anoano St 1501 3 of 41 Listing Image for 50 Puu Anoano St 1501 4 of 41 Listing Image for 50 Puu Anoano St 1501 5 of 41 Listing Image for 50 Puu Anoano St 1501 6 of 41 Listing Image for 50 Puu Anoano St 1501 7 of 41 Listing Image for 50 Puu Anoano St 1501 8 of 41 Listing Image for 50 Puu Anoano St 1501 9 of 41 Listing Image for 50 Puu Anoano St 1501 10 of 41 Listing Image for 50 Puu Anoano St 1501 11 of 41 Listing Image for 50 Puu Anoano St 1501 12 of 41 Listing Image for 50 Puu Anoano St 1501 13 of 41 Listing Image for 50 Puu Anoano St 1501 14 of 41 Listing Image for 50 Puu Anoano St 1501 15 of 41 Listing Image for 50 Puu Anoano St 1501 16 of 41 Listing Image for 50 Puu Anoano St 1501 17 of 41 Listing Image for 50 Puu Anoano St 1501 18 of 41 Listing Image for 50 Puu Anoano St 1501 19 of 41 Listing Image for 50 Puu Anoano St 1501 20 of 41 Listing Image for 50 Puu Anoano St 1501 21 of 41 Listing Image for 50 Puu Anoano St 1501 22 of 41 Listing Image for 50 Puu Anoano St 1501 23 of 41 Listing Image for 50 Puu Anoano St 1501 24 of 41 Listing Image for 50 Puu Anoano St 1501 25 of 41 Listing Image for 50 Puu Anoano St 1501 26 of 41 Listing Image for 50 Puu Anoano St 1501 27 of 41 Listing Image for 50 Puu Anoano St 1501 28 of 41 Listing Image for 50 Puu Anoano St 1501 29 of 41 Listing Image for 50 Puu Anoano St 1501 30 of 41 Listing Image for 50 Puu Anoano St 1501 31 of 41 Listing Image for 50 Puu Anoano St 1501 32 of 41 Listing Image for 50 Puu Anoano St 1501 33 of 41 Listing Image for 50 Puu Anoano St 1501 34 of 41 Listing Image for 50 Puu Anoano St 1501 35 of 41 Listing Image for 50 Puu Anoano St 1501 36 of 41 Listing Image for 50 Puu Anoano St 1501 37 of 41 Listing Image for 50 Puu Anoano St 1501 38 of 41 Listing Image for 50 Puu Anoano St 1501 39 of 41 Listing Image for 50 Puu Anoano St 1501 40 of 41 Listing Image for 50 Puu Anoano St 1501 41 of 41

$1,050,000

↓ $208,000

Masters 1501

50 Puu Anoano St 1501, Kaanapali

2 Beds 2 Baths 1,544 SqFt Residential MLS® # 407086 Date Sold: November 7, 2025
View 6 More Listings

Consider a Bridge Loan

When looking at how to buy a house before selling yours, a bridge loan may be a great solution. A bridge loan, a short-term loan with a higher interest rate, can be used to refinance your current home mortgage or pull equity out as a second lien.

With interest-only payments, you can tap into your equity to use as a down payment to purchase a second home. You can also potentially decrease your first home’s mortgage payments, which will be beneficial if the closing dates do not align perfectly.

Choose a Low Down Payment Loan Program

While many mortgage lenders will require you to make a sizable down payment when you buy a house, there are lending solutions available that allow you to put down 5% or less. A Fannie Mae loan, for example, only requires 3% down. While the interest rates on these loans are competitive, you may be responsible for Mortgage Payment Insurance (MPI).

MPI could add hundreds of dollars to your monthly mortgage payment. With a low down payment loan, however, you may not need to access your current home’s equity to complete your purchase.

Borrow Against Your Retirement Account

Generally, your retirement account’s funds are inaccessible to you until you reach the age of 59.5 years old. Most withdrawals taken before you reach this age can trigger a penalty and will be taxable. However, the IRS allows you to withdraw funds without penalty to buy a house.

There are specific rules and requirements that you should research thoroughly before pursuing this option. Your retirement account funds can be used for a down payment as well as closing costs, and this could eliminate the need to sell your house before buying a new one.

Add a Contingency to the Sales Contract

If you have determined that the other options available are not suitable for your unique situation, another possibility is available. When considering how to buy a second home without selling the first, a sales contingency could be written into the new sales contract. A sales contingency can be worded so that your purchase is dependent on the sale of the current house. 

While this can seem like the perfect solution, be aware that many sellers may not accept this contingency. Like you, other sellers may be trying to sell their house to buy another property. If they delay their sale because of a sales contingency, they may not be able to structure their own timeline to suit their needs. Your real estate agent can work with you to structure a sales contingency with an agreeable seller.

Turn Your Home Into an Investment Property

If you are concerned about the possibility of having two mortgage payments at the same time, you could consider renting out your first home. The monthly rent from your rental property could cover its mortgage payment, property taxes, and other expenses. The remaining rental income is a profit that can be used as desired.

If you are unable to qualify for a new home loan for your purchase with the old mortgage in place, renting the property can help. Once you have a signed lease in place on your first home, your mortgage lender can apply that income to your debt-to-income ratio. 

Before turning your home into a rental, consult with your realtor. Your real estate agent can provide you with a fair market rental rate for the property. This information is required to determine if its monthly rent will cover its expenses. The IRS allows you to write off many property expenses, including upkeep costs, management fees, property taxes, etc. Depending on the situation, a property owner could possibly turn a profit on a rental house while enjoying a tax loss.

Consider Buying a Second Home

Buying a second home has advantages to consider as well. If you buy a second home, you can enjoy traveling back and forth between the locations as desired. When you are not using a home for personal use, you could rent it out as a rental property. A second home also has tax benefits

Even if you do not use the second home to produce rental income, you may qualify for the same homeowner tax deductions as you benefit from with your first home. Before buying a second home or turning your current home into a rental property, consider speaking to a tax advisor and a management company to explore all of the financial ramifications in detail.

Executing a 1031 Exchange

1031 Exchange Maui

When doing a 1031 exchange, you'll typically be selling the property you are going to exchange first and then immedietley seeking a replacement property. Read my full rundown on how to successfully navigate the process here

Explore Your Options Today

Keep in mind that you can combine multiple solutions presented here as you walk through the real estate process. For example, you could take out a home equity loan on your current home to access down payment funds to purchase your second home. At the same time, you could turn your first home into a rental property to generate monthly income.

This example is only one of many ways to combine these solutions and set up a scenario that suits your needs. Contact a local real estate agent to learn more about the housing and rental market.

Get In Touch With Evan!

Evan Harlow Maui

Evan Harlow ranks among the best real estate agents on Maui annually and is in the top 1% of Coldwell Banker agents worldwide in production. Evan has the expertise, experience, and work ethic to help you achieve your real estate buying and selling goals. We promise exceptional service and support from the beginning of the process through closing and beyond. See what Evan's clients are saying on Google.

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