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 2840 Koea Pl 1 of 37 Listing Image for 2840 Koea Pl 2 of 37 Listing Image for 2840 Koea Pl 3 of 37 Listing Image for 2840 Koea Pl 4 of 37 Listing Image for 2840 Koea Pl 5 of 37 Listing Image for 2840 Koea Pl 6 of 37 Listing Image for 2840 Koea Pl 7 of 37 Listing Image for 2840 Koea Pl 8 of 37 Listing Image for 2840 Koea Pl 9 of 37 Listing Image for 2840 Koea Pl 10 of 37 Listing Image for 2840 Koea Pl 11 of 37 Listing Image for 2840 Koea Pl 12 of 37 Listing Image for 2840 Koea Pl 13 of 37 Listing Image for 2840 Koea Pl 14 of 37 Listing Image for 2840 Koea Pl 15 of 37 Listing Image for 2840 Koea Pl 16 of 37 Listing Image for 2840 Koea Pl 17 of 37 Listing Image for 2840 Koea Pl 18 of 37 Listing Image for 2840 Koea Pl 19 of 37 Listing Image for 2840 Koea Pl 20 of 37 Listing Image for 2840 Koea Pl 21 of 37 Listing Image for 2840 Koea Pl 22 of 37 Listing Image for 2840 Koea Pl 23 of 37 Listing Image for 2840 Koea Pl 24 of 37 Listing Image for 2840 Koea Pl 25 of 37 Listing Image for 2840 Koea Pl 26 of 37 Listing Image for 2840 Koea Pl 27 of 37 Listing Image for 2840 Koea Pl 28 of 37 Listing Image for 2840 Koea Pl 29 of 37 Listing Image for 2840 Koea Pl 30 of 37 Listing Image for 2840 Koea Pl 31 of 37 Listing Image for 2840 Koea Pl 32 of 37 Listing Image for 2840 Koea Pl 33 of 37 Listing Image for 2840 Koea Pl 34 of 37 Listing Image for 2840 Koea Pl 35 of 37 Listing Image for 2840 Koea Pl 36 of 37 Listing Image for 2840 Koea Pl 37 of 37

$989,000

↓ $50,000

Makawao/Olinda/Haliimaile

2840 Koea Pl, Makawao/Olinda/Haliimaile

3 Beds 1.5 Baths 1,152 SqFt Residential MLS® # 409804

Days on Market: 105

Corcoran Pacific Properties

Listing Image for 648 Kaae Rd 1 of 5 Listing Image for 648 Kaae Rd 2 of 5 Listing Image for 648 Kaae Rd 3 of 5 Listing Image for 648 Kaae Rd 4 of 5 Listing Image for 648 Kaae Rd 5 of 5

$1,278,000

Waiehu

648 Kaae Rd, Wailuku

4 Beds 2 Baths 1,216 SqFt Residential MLS® # 409802

Days on Market: 105

Maui & Co Real Estate LLC

Short Term Rental
Listing Image for 2994 S Kihei Rd 106 1 of 50 Listing Image for 2994 S Kihei Rd 106 2 of 50 Listing Image for 2994 S Kihei Rd 106 3 of 50 Listing Image for 2994 S Kihei Rd 106 4 of 50 Listing Image for 2994 S Kihei Rd 106 5 of 50 Listing Image for 2994 S Kihei Rd 106 6 of 50 Listing Image for 2994 S Kihei Rd 106 7 of 50 Listing Image for 2994 S Kihei Rd 106 8 of 50 Listing Image for 2994 S Kihei Rd 106 9 of 50 Listing Image for 2994 S Kihei Rd 106 10 of 50 Listing Image for 2994 S Kihei Rd 106 11 of 50 Listing Image for 2994 S Kihei Rd 106 12 of 50 Listing Image for 2994 S Kihei Rd 106 13 of 50 Listing Image for 2994 S Kihei Rd 106 14 of 50 Listing Image for 2994 S Kihei Rd 106 15 of 50 Listing Image for 2994 S Kihei Rd 106 16 of 50 Listing Image for 2994 S Kihei Rd 106 17 of 50 Listing Image for 2994 S Kihei Rd 106 18 of 50 Listing Image for 2994 S Kihei Rd 106 19 of 50 Listing Image for 2994 S Kihei Rd 106 20 of 50 Listing Image for 2994 S Kihei Rd 106 21 of 50 Listing Image for 2994 S Kihei Rd 106 22 of 50 Listing Image for 2994 S Kihei Rd 106 23 of 50 Listing Image for 2994 S Kihei Rd 106 24 of 50 Listing Image for 2994 S Kihei Rd 106 25 of 50 Listing Image for 2994 S Kihei Rd 106 26 of 50 Listing Image for 2994 S Kihei Rd 106 27 of 50 Listing Image for 2994 S Kihei Rd 106 28 of 50 Listing Image for 2994 S Kihei Rd 106 29 of 50 Listing Image for 2994 S Kihei Rd 106 30 of 50 Listing Image for 2994 S Kihei Rd 106 31 of 50 Listing Image for 2994 S Kihei Rd 106 32 of 50 Listing Image for 2994 S Kihei Rd 106 33 of 50 Listing Image for 2994 S Kihei Rd 106 34 of 50 Listing Image for 2994 S Kihei Rd 106 35 of 50 Listing Image for 2994 S Kihei Rd 106 36 of 50 Listing Image for 2994 S Kihei Rd 106 37 of 50 Listing Image for 2994 S Kihei Rd 106 38 of 50 Listing Image for 2994 S Kihei Rd 106 39 of 50 Listing Image for 2994 S Kihei Rd 106 40 of 50 Listing Image for 2994 S Kihei Rd 106 41 of 50 Listing Image for 2994 S Kihei Rd 106 42 of 50 Listing Image for 2994 S Kihei Rd 106 43 of 50 Listing Image for 2994 S Kihei Rd 106 44 of 50 Listing Image for 2994 S Kihei Rd 106 45 of 50 Listing Image for 2994 S Kihei Rd 106 46 of 50 Listing Image for 2994 S Kihei Rd 106 47 of 50 Listing Image for 2994 S Kihei Rd 106 48 of 50 Listing Image for 2994 S Kihei Rd 106 49 of 50 Listing Image for 2994 S Kihei Rd 106 50 of 50

$1,590,000

Hale Hui Kai 106

2994 S Kihei Rd 106, Kihei

2 Beds 2 Baths 898 SqFt Residential MLS® # 409801

Days on Market: 105

Hawaii Life (W) Cell: 808-283-4688

Listing Image for 1536 Halama St 1 of 44 Listing Image for 1536 Halama St 2 of 44 Listing Image for 1536 Halama St 3 of 44 Listing Image for 1536 Halama St 4 of 44 Listing Image for 1536 Halama St 5 of 44 Listing Image for 1536 Halama St 6 of 44 Listing Image for 1536 Halama St 7 of 44 Listing Image for 1536 Halama St 8 of 44 Listing Image for 1536 Halama St 9 of 44 Listing Image for 1536 Halama St 10 of 44 Listing Image for 1536 Halama St 11 of 44 Listing Image for 1536 Halama St 12 of 44 Listing Image for 1536 Halama St 13 of 44 Listing Image for 1536 Halama St 14 of 44 Listing Image for 1536 Halama St 15 of 44 Listing Image for 1536 Halama St 16 of 44 Listing Image for 1536 Halama St 17 of 44 Listing Image for 1536 Halama St 18 of 44 Listing Image for 1536 Halama St 19 of 44 Listing Image for 1536 Halama St 20 of 44 Listing Image for 1536 Halama St 21 of 44 Listing Image for 1536 Halama St 22 of 44 Listing Image for 1536 Halama St 23 of 44 Listing Image for 1536 Halama St 24 of 44 Listing Image for 1536 Halama St 25 of 44 Listing Image for 1536 Halama St 26 of 44 Listing Image for 1536 Halama St 27 of 44 Listing Image for 1536 Halama St 28 of 44 Listing Image for 1536 Halama St 29 of 44 Listing Image for 1536 Halama St 30 of 44 Listing Image for 1536 Halama St 31 of 44 Listing Image for 1536 Halama St 32 of 44 Listing Image for 1536 Halama St 33 of 44 Listing Image for 1536 Halama St 34 of 44 Listing Image for 1536 Halama St 35 of 44 Listing Image for 1536 Halama St 36 of 44 Listing Image for 1536 Halama St 37 of 44 Listing Image for 1536 Halama St 38 of 44 Listing Image for 1536 Halama St 39 of 44 Listing Image for 1536 Halama St 40 of 44 Listing Image for 1536 Halama St 41 of 44 Listing Image for 1536 Halama St 42 of 44 Listing Image for 1536 Halama St 43 of 44 Listing Image for 1536 Halama St 44 of 44

$12,400,000

Halama Street

1536 Halama St, Kihei

5 Beds 5.5 Baths 5,070 SqFt Residential MLS® # 409793

Days on Market: 105

Island Sotheby's International Realty(M) Cell: 808-856-6039

Short Term Rental
Listing Image for 500 Kapalua Dr 27v-3 1 of 50 Listing Image for 500 Kapalua Dr 27v-3 2 of 50 Listing Image for 500 Kapalua Dr 27v-3 3 of 50 Listing Image for 500 Kapalua Dr 27v-3 4 of 50 Listing Image for 500 Kapalua Dr 27v-3 5 of 50 Listing Image for 500 Kapalua Dr 27v-3 6 of 50 Listing Image for 500 Kapalua Dr 27v-3 7 of 50 Listing Image for 500 Kapalua Dr 27v-3 8 of 50 Listing Image for 500 Kapalua Dr 27v-3 9 of 50 Listing Image for 500 Kapalua Dr 27v-3 10 of 50 Listing Image for 500 Kapalua Dr 27v-3 11 of 50 Listing Image for 500 Kapalua Dr 27v-3 12 of 50 Listing Image for 500 Kapalua Dr 27v-3 13 of 50 Listing Image for 500 Kapalua Dr 27v-3 14 of 50 Listing Image for 500 Kapalua Dr 27v-3 15 of 50 Listing Image for 500 Kapalua Dr 27v-3 16 of 50 Listing Image for 500 Kapalua Dr 27v-3 17 of 50 Listing Image for 500 Kapalua Dr 27v-3 18 of 50 Listing Image for 500 Kapalua Dr 27v-3 19 of 50 Listing Image for 500 Kapalua Dr 27v-3 20 of 50 Listing Image for 500 Kapalua Dr 27v-3 21 of 50 Listing Image for 500 Kapalua Dr 27v-3 22 of 50 Listing Image for 500 Kapalua Dr 27v-3 23 of 50 Listing Image for 500 Kapalua Dr 27v-3 24 of 50 Listing Image for 500 Kapalua Dr 27v-3 25 of 50 Listing Image for 500 Kapalua Dr 27v-3 26 of 50 Listing Image for 500 Kapalua Dr 27v-3 27 of 50 Listing Image for 500 Kapalua Dr 27v-3 28 of 50 Listing Image for 500 Kapalua Dr 27v-3 29 of 50 Listing Image for 500 Kapalua Dr 27v-3 30 of 50 Listing Image for 500 Kapalua Dr 27v-3 31 of 50 Listing Image for 500 Kapalua Dr 27v-3 32 of 50 Listing Image for 500 Kapalua Dr 27v-3 33 of 50 Listing Image for 500 Kapalua Dr 27v-3 34 of 50 Listing Image for 500 Kapalua Dr 27v-3 35 of 50 Listing Image for 500 Kapalua Dr 27v-3 36 of 50 Listing Image for 500 Kapalua Dr 27v-3 37 of 50 Listing Image for 500 Kapalua Dr 27v-3 38 of 50 Listing Image for 500 Kapalua Dr 27v-3 39 of 50 Listing Image for 500 Kapalua Dr 27v-3 40 of 50 Listing Image for 500 Kapalua Dr 27v-3 41 of 50 Listing Image for 500 Kapalua Dr 27v-3 42 of 50 Listing Image for 500 Kapalua Dr 27v-3 43 of 50 Listing Image for 500 Kapalua Dr 27v-3 44 of 50 Listing Image for 500 Kapalua Dr 27v-3 45 of 50 Listing Image for 500 Kapalua Dr 27v-3 46 of 50 Listing Image for 500 Kapalua Dr 27v-3 47 of 50 Listing Image for 500 Kapalua Dr 27v-3 48 of 50 Listing Image for 500 Kapalua Dr 27v-3 49 of 50 Listing Image for 500 Kapalua Dr 27v-3 50 of 50

$1,300,000

Kapalua Golf Villas 27V-3

500 Kapalua Dr 27v-3, Kapalua

1 Bed 1.5 Baths 899 SqFt Residential MLS® # 409792

Days on Market: 105

Keller Williams Realty Maui-Ka Cell: 808-276-8776

In Escrow Short Term Rental
Listing Image for 500 Bay Dr 21b-3 1 of 42 Listing Image for 500 Bay Dr 21b-3 2 of 42 Listing Image for 500 Bay Dr 21b-3 3 of 42 Listing Image for 500 Bay Dr 21b-3 4 of 42 Listing Image for 500 Bay Dr 21b-3 5 of 42 Listing Image for 500 Bay Dr 21b-3 6 of 42 Listing Image for 500 Bay Dr 21b-3 7 of 42 Listing Image for 500 Bay Dr 21b-3 8 of 42 Listing Image for 500 Bay Dr 21b-3 9 of 42 Listing Image for 500 Bay Dr 21b-3 10 of 42 Listing Image for 500 Bay Dr 21b-3 11 of 42 Listing Image for 500 Bay Dr 21b-3 12 of 42 Listing Image for 500 Bay Dr 21b-3 13 of 42 Listing Image for 500 Bay Dr 21b-3 14 of 42 Listing Image for 500 Bay Dr 21b-3 15 of 42 Listing Image for 500 Bay Dr 21b-3 16 of 42 Listing Image for 500 Bay Dr 21b-3 17 of 42 Listing Image for 500 Bay Dr 21b-3 18 of 42 Listing Image for 500 Bay Dr 21b-3 19 of 42 Listing Image for 500 Bay Dr 21b-3 20 of 42 Listing Image for 500 Bay Dr 21b-3 21 of 42 Listing Image for 500 Bay Dr 21b-3 22 of 42 Listing Image for 500 Bay Dr 21b-3 23 of 42 Listing Image for 500 Bay Dr 21b-3 24 of 42 Listing Image for 500 Bay Dr 21b-3 25 of 42 Listing Image for 500 Bay Dr 21b-3 26 of 42 Listing Image for 500 Bay Dr 21b-3 27 of 42 Listing Image for 500 Bay Dr 21b-3 28 of 42 Listing Image for 500 Bay Dr 21b-3 29 of 42 Listing Image for 500 Bay Dr 21b-3 30 of 42 Listing Image for 500 Bay Dr 21b-3 31 of 42 Listing Image for 500 Bay Dr 21b-3 32 of 42 Listing Image for 500 Bay Dr 21b-3 33 of 42 Listing Image for 500 Bay Dr 21b-3 34 of 42 Listing Image for 500 Bay Dr 21b-3 35 of 42 Listing Image for 500 Bay Dr 21b-3 36 of 42 Listing Image for 500 Bay Dr 21b-3 37 of 42 Listing Image for 500 Bay Dr 21b-3 38 of 42 Listing Image for 500 Bay Dr 21b-3 39 of 42 Listing Image for 500 Bay Dr 21b-3 40 of 42 Listing Image for 500 Bay Dr 21b-3 41 of 42 Listing Image for 500 Bay Dr 21b-3 42 of 42

$1,525,000

Kapalua Bay Villas 21B-3

500 Bay Dr 21b-3, Kapalua

1 Bed 1.5 Baths 995 SqFt Residential MLS® # 406926

Days on Market: 386

Lowson & Associates laurie@lowson.com

Short Term Rental
Listing Image for 4909 Lower Honoapiilani Rd A10 1 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 2 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 3 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 4 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 5 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 6 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 7 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 8 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 9 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 10 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 11 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 12 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 13 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 14 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 15 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 16 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 17 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 18 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 19 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 20 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 21 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 22 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 23 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 24 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 25 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 26 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 27 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 28 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 29 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 30 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 31 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 32 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 33 of 34 Listing Image for 4909 Lower Honoapiilani Rd A10 34 of 34

$1,300,000

Kahana Sunset A10

4909 Lower Honoapiilani Rd A10, Napili/Kahana/Honokowai

2 Beds 2.5 Baths 1,064 SqFt Residential MLS® # 409789

Days on Market: 106

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

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: 06/01/2026
Listing Image for 263 Kahoma Village Loop 12-105 1 of 48 Listing Image for 263 Kahoma Village Loop 12-105 2 of 48 Listing Image for 263 Kahoma Village Loop 12-105 3 of 48 Listing Image for 263 Kahoma Village Loop 12-105 4 of 48 Listing Image for 263 Kahoma Village Loop 12-105 5 of 48 Listing Image for 263 Kahoma Village Loop 12-105 6 of 48 Listing Image for 263 Kahoma Village Loop 12-105 7 of 48 Listing Image for 263 Kahoma Village Loop 12-105 8 of 48 Listing Image for 263 Kahoma Village Loop 12-105 9 of 48 Listing Image for 263 Kahoma Village Loop 12-105 10 of 48 Listing Image for 263 Kahoma Village Loop 12-105 11 of 48 Listing Image for 263 Kahoma Village Loop 12-105 12 of 48 Listing Image for 263 Kahoma Village Loop 12-105 13 of 48 Listing Image for 263 Kahoma Village Loop 12-105 14 of 48 Listing Image for 263 Kahoma Village Loop 12-105 15 of 48 Listing Image for 263 Kahoma Village Loop 12-105 16 of 48 Listing Image for 263 Kahoma Village Loop 12-105 17 of 48 Listing Image for 263 Kahoma Village Loop 12-105 18 of 48 Listing Image for 263 Kahoma Village Loop 12-105 19 of 48 Listing Image for 263 Kahoma Village Loop 12-105 20 of 48 Listing Image for 263 Kahoma Village Loop 12-105 21 of 48 Listing Image for 263 Kahoma Village Loop 12-105 22 of 48 Listing Image for 263 Kahoma Village Loop 12-105 23 of 48 Listing Image for 263 Kahoma Village Loop 12-105 24 of 48 Listing Image for 263 Kahoma Village Loop 12-105 25 of 48 Listing Image for 263 Kahoma Village Loop 12-105 26 of 48 Listing Image for 263 Kahoma Village Loop 12-105 27 of 48 Listing Image for 263 Kahoma Village Loop 12-105 28 of 48 Listing Image for 263 Kahoma Village Loop 12-105 29 of 48 Listing Image for 263 Kahoma Village Loop 12-105 30 of 48 Listing Image for 263 Kahoma Village Loop 12-105 31 of 48 Listing Image for 263 Kahoma Village Loop 12-105 32 of 48 Listing Image for 263 Kahoma Village Loop 12-105 33 of 48 Listing Image for 263 Kahoma Village Loop 12-105 34 of 48 Listing Image for 263 Kahoma Village Loop 12-105 35 of 48 Listing Image for 263 Kahoma Village Loop 12-105 36 of 48 Listing Image for 263 Kahoma Village Loop 12-105 37 of 48 Listing Image for 263 Kahoma Village Loop 12-105 38 of 48 Listing Image for 263 Kahoma Village Loop 12-105 39 of 48 Listing Image for 263 Kahoma Village Loop 12-105 40 of 48 Listing Image for 263 Kahoma Village Loop 12-105 41 of 48 Listing Image for 263 Kahoma Village Loop 12-105 42 of 48 Listing Image for 263 Kahoma Village Loop 12-105 43 of 48 Listing Image for 263 Kahoma Village Loop 12-105 44 of 48 Listing Image for 263 Kahoma Village Loop 12-105 45 of 48 Listing Image for 263 Kahoma Village Loop 12-105 46 of 48 Listing Image for 263 Kahoma Village Loop 12-105 47 of 48 Listing Image for 263 Kahoma Village Loop 12-105 48 of 48

$890,000

Kahoma Village 12-105

263 Kahoma Village Loop 12-105, Lahaina

3 Beds 2.5 Baths 1,226 SqFt Residential MLS® # 408525 Date Sold: June 1, 2026
Sold
Closed: 07/17/2026
Listing Image for 118 Waiapo St 1 of 32 Listing Image for 118 Waiapo St 2 of 32 Listing Image for 118 Waiapo St 3 of 32 Listing Image for 118 Waiapo St 4 of 32 Listing Image for 118 Waiapo St 5 of 32 Listing Image for 118 Waiapo St 6 of 32 Listing Image for 118 Waiapo St 7 of 32 Listing Image for 118 Waiapo St 8 of 32 Listing Image for 118 Waiapo St 9 of 32 Listing Image for 118 Waiapo St 10 of 32 Listing Image for 118 Waiapo St 11 of 32 Listing Image for 118 Waiapo St 12 of 32 Listing Image for 118 Waiapo St 13 of 32 Listing Image for 118 Waiapo St 14 of 32 Listing Image for 118 Waiapo St 15 of 32 Listing Image for 118 Waiapo St 16 of 32 Listing Image for 118 Waiapo St 17 of 32 Listing Image for 118 Waiapo St 18 of 32 Listing Image for 118 Waiapo St 19 of 32 Listing Image for 118 Waiapo St 20 of 32 Listing Image for 118 Waiapo St 21 of 32 Listing Image for 118 Waiapo St 22 of 32 Listing Image for 118 Waiapo St 23 of 32 Listing Image for 118 Waiapo St 24 of 32 Listing Image for 118 Waiapo St 25 of 32 Listing Image for 118 Waiapo St 26 of 32 Listing Image for 118 Waiapo St 27 of 32 Listing Image for 118 Waiapo St 28 of 32 Listing Image for 118 Waiapo St 29 of 32 Listing Image for 118 Waiapo St 30 of 32 Listing Image for 118 Waiapo St 31 of 32 Listing Image for 118 Waiapo St 32 of 32

$1,050,000

↓ $240,000

Kamalii Alayna

118 Waiapo St, Kihei

3 Beds 2.5 Baths 1,560 SqFt Residential MLS® # 408522 Date Sold: July 17, 2026
Sold
Closed: 06/09/2026
Listing Image for 70 Wailau Pl 1 of 36 Listing Image for 70 Wailau Pl 2 of 36 Listing Image for 70 Wailau Pl 3 of 36 Listing Image for 70 Wailau Pl 4 of 36 Listing Image for 70 Wailau Pl 5 of 36 Listing Image for 70 Wailau Pl 6 of 36 Listing Image for 70 Wailau Pl 7 of 36 Listing Image for 70 Wailau Pl 8 of 36 Listing Image for 70 Wailau Pl 9 of 36 Listing Image for 70 Wailau Pl 10 of 36 Listing Image for 70 Wailau Pl 11 of 36 Listing Image for 70 Wailau Pl 12 of 36 Listing Image for 70 Wailau Pl 13 of 36 Listing Image for 70 Wailau Pl 14 of 36 Listing Image for 70 Wailau Pl 15 of 36 Listing Image for 70 Wailau Pl 16 of 36 Listing Image for 70 Wailau Pl 17 of 36 Listing Image for 70 Wailau Pl 18 of 36 Listing Image for 70 Wailau Pl 19 of 36 Listing Image for 70 Wailau Pl 20 of 36 Listing Image for 70 Wailau Pl 21 of 36 Listing Image for 70 Wailau Pl 22 of 36 Listing Image for 70 Wailau Pl 23 of 36 Listing Image for 70 Wailau Pl 24 of 36 Listing Image for 70 Wailau Pl 25 of 36 Listing Image for 70 Wailau Pl 26 of 36 Listing Image for 70 Wailau Pl 27 of 36 Listing Image for 70 Wailau Pl 28 of 36 Listing Image for 70 Wailau Pl 29 of 36 Listing Image for 70 Wailau Pl 30 of 36 Listing Image for 70 Wailau Pl 31 of 36 Listing Image for 70 Wailau Pl 32 of 36 Listing Image for 70 Wailau Pl 33 of 36 Listing Image for 70 Wailau Pl 34 of 36 Listing Image for 70 Wailau Pl 35 of 36 Listing Image for 70 Wailau Pl 36 of 36

$1,950,000

↓ $140,000

Mahanalua Nui IV

70 Wailau Pl, Lahaina

3 Beds 2 Baths 1,294 SqFt Residential MLS® # 408521 Date Sold: June 9, 2026
Sold
Closed: 03/27/2026
Listing Image for 44 Polale St 1 of 28 Listing Image for 44 Polale St 2 of 28 Listing Image for 44 Polale St 3 of 28 Listing Image for 44 Polale St 4 of 28 Listing Image for 44 Polale St 5 of 28 Listing Image for 44 Polale St 6 of 28 Listing Image for 44 Polale St 7 of 28 Listing Image for 44 Polale St 8 of 28 Listing Image for 44 Polale St 9 of 28 Listing Image for 44 Polale St 10 of 28 Listing Image for 44 Polale St 11 of 28 Listing Image for 44 Polale St 12 of 28 Listing Image for 44 Polale St 13 of 28 Listing Image for 44 Polale St 14 of 28 Listing Image for 44 Polale St 15 of 28 Listing Image for 44 Polale St 16 of 28 Listing Image for 44 Polale St 17 of 28 Listing Image for 44 Polale St 18 of 28 Listing Image for 44 Polale St 19 of 28 Listing Image for 44 Polale St 20 of 28 Listing Image for 44 Polale St 21 of 28 Listing Image for 44 Polale St 22 of 28 Listing Image for 44 Polale St 23 of 28 Listing Image for 44 Polale St 24 of 28 Listing Image for 44 Polale St 25 of 28 Listing Image for 44 Polale St 26 of 28 Listing Image for 44 Polale St 27 of 28 Listing Image for 44 Polale St 28 of 28

$1,130,000

Piilani Villages II

44 Polale St, Kihei

3 Beds 2 Baths 1,478 SqFt Residential MLS® # 408515 Date Sold: March 27, 2026
Buying Real Estate on Maui

Buying Real Estate on Maui

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Sold
Closed: 02/20/2026
Listing Image for 2450 S Kihei Rd 305 1 of 45 Listing Image for 2450 S Kihei Rd 305 2 of 45 Listing Image for 2450 S Kihei Rd 305 3 of 45 Listing Image for 2450 S Kihei Rd 305 4 of 45 Listing Image for 2450 S Kihei Rd 305 5 of 45 Listing Image for 2450 S Kihei Rd 305 6 of 45 Listing Image for 2450 S Kihei Rd 305 7 of 45 Listing Image for 2450 S Kihei Rd 305 8 of 45 Listing Image for 2450 S Kihei Rd 305 9 of 45 Listing Image for 2450 S Kihei Rd 305 10 of 45 Listing Image for 2450 S Kihei Rd 305 11 of 45 Listing Image for 2450 S Kihei Rd 305 12 of 45 Listing Image for 2450 S Kihei Rd 305 13 of 45 Listing Image for 2450 S Kihei Rd 305 14 of 45 Listing Image for 2450 S Kihei Rd 305 15 of 45 Listing Image for 2450 S Kihei Rd 305 16 of 45 Listing Image for 2450 S Kihei Rd 305 17 of 45 Listing Image for 2450 S Kihei Rd 305 18 of 45 Listing Image for 2450 S Kihei Rd 305 19 of 45 Listing Image for 2450 S Kihei Rd 305 20 of 45 Listing Image for 2450 S Kihei Rd 305 21 of 45 Listing Image for 2450 S Kihei Rd 305 22 of 45 Listing Image for 2450 S Kihei Rd 305 23 of 45 Listing Image for 2450 S Kihei Rd 305 24 of 45 Listing Image for 2450 S Kihei Rd 305 25 of 45 Listing Image for 2450 S Kihei Rd 305 26 of 45 Listing Image for 2450 S Kihei Rd 305 27 of 45 Listing Image for 2450 S Kihei Rd 305 28 of 45 Listing Image for 2450 S Kihei Rd 305 29 of 45 Listing Image for 2450 S Kihei Rd 305 30 of 45 Listing Image for 2450 S Kihei Rd 305 31 of 45 Listing Image for 2450 S Kihei Rd 305 32 of 45 Listing Image for 2450 S Kihei Rd 305 33 of 45 Listing Image for 2450 S Kihei Rd 305 34 of 45 Listing Image for 2450 S Kihei Rd 305 35 of 45 Listing Image for 2450 S Kihei Rd 305 36 of 45 Listing Image for 2450 S Kihei Rd 305 37 of 45 Listing Image for 2450 S Kihei Rd 305 38 of 45 Listing Image for 2450 S Kihei Rd 305 39 of 45 Listing Image for 2450 S Kihei Rd 305 40 of 45 Listing Image for 2450 S Kihei Rd 305 41 of 45 Listing Image for 2450 S Kihei Rd 305 42 of 45 Listing Image for 2450 S Kihei Rd 305 43 of 45 Listing Image for 2450 S Kihei Rd 305 44 of 45 Listing Image for 2450 S Kihei Rd 305 45 of 45

$1,260,000

Kamaole Nalu 305

2450 S Kihei Rd 305, Kihei

2 Beds 2 Baths 774 SqFt Residential MLS® # 408514 Date Sold: February 20, 2026
Sold
Closed: 03/02/2026
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$1,200,000

Waimahaihai

107 Mehani Pl, Kihei

4 Beds 2 Baths 1,840 SqFt Residential MLS® # 408513 Date Sold: March 2, 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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