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 3950 Kalai Waa St U202 1 of 26 Listing Image for 3950 Kalai Waa St U202 2 of 26 Listing Image for 3950 Kalai Waa St U202 3 of 26 Listing Image for 3950 Kalai Waa St U202 4 of 26 Listing Image for 3950 Kalai Waa St U202 5 of 26 Listing Image for 3950 Kalai Waa St U202 6 of 26 Listing Image for 3950 Kalai Waa St U202 7 of 26 Listing Image for 3950 Kalai Waa St U202 8 of 26 Listing Image for 3950 Kalai Waa St U202 9 of 26 Listing Image for 3950 Kalai Waa St U202 10 of 26 Listing Image for 3950 Kalai Waa St U202 11 of 26 Listing Image for 3950 Kalai Waa St U202 12 of 26 Listing Image for 3950 Kalai Waa St U202 13 of 26 Listing Image for 3950 Kalai Waa St U202 14 of 26 Listing Image for 3950 Kalai Waa St U202 15 of 26 Listing Image for 3950 Kalai Waa St U202 16 of 26 Listing Image for 3950 Kalai Waa St U202 17 of 26 Listing Image for 3950 Kalai Waa St U202 18 of 26 Listing Image for 3950 Kalai Waa St U202 19 of 26 Listing Image for 3950 Kalai Waa St U202 20 of 26 Listing Image for 3950 Kalai Waa St U202 21 of 26 Listing Image for 3950 Kalai Waa St U202 22 of 26 Listing Image for 3950 Kalai Waa St U202 23 of 26 Listing Image for 3950 Kalai Waa St U202 24 of 26 Listing Image for 3950 Kalai Waa St U202 25 of 26 Listing Image for 3950 Kalai Waa St U202 26 of 26

$999,500

Wailea Fairway Villas U202

3950 Kalai Waa St U202, Wailea/Makena

2 Beds 2 Baths 949 SqFt Residential MLS® # 409449

Days on Market: 139

Berkshire Hathaway Maui Prop-W

Listing Image for 4000 Wailea Alanui Dr 802 & 804 1 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 2 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 3 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 4 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 5 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 6 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 7 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 8 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 9 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 10 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 11 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 12 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 13 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 14 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 15 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 16 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 17 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 18 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 19 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 20 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 21 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 22 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 23 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 24 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 25 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 26 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 27 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 28 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 29 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 30 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 31 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 32 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 33 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 34 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 35 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 36 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 37 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 38 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 39 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 40 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 41 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 42 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 43 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 44 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 45 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 46 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 47 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 48 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 49 of 50 Listing Image for 4000 Wailea Alanui Dr 802 & 804 50 of 50

$8,740,000

Wailea Point 802 & 804

4000 Wailea Alanui Dr 802 & 804, Wailea/Makena

5 Beds 6 Baths 4,913 SqFt Residential MLS® # 409447

Days on Market: 139

Wailea Point Realty, Inc. realty@waileapoint.com

Listing Image for 624 Alihilani St 1 of 39 Listing Image for 624 Alihilani St 2 of 39 Listing Image for 624 Alihilani St 3 of 39 Listing Image for 624 Alihilani St 4 of 39 Listing Image for 624 Alihilani St 5 of 39 Listing Image for 624 Alihilani St 6 of 39 Listing Image for 624 Alihilani St 7 of 39 Listing Image for 624 Alihilani St 8 of 39 Listing Image for 624 Alihilani St 9 of 39 Listing Image for 624 Alihilani St 10 of 39 Listing Image for 624 Alihilani St 11 of 39 Listing Image for 624 Alihilani St 12 of 39 Listing Image for 624 Alihilani St 13 of 39 Listing Image for 624 Alihilani St 14 of 39 Listing Image for 624 Alihilani St 15 of 39 Listing Image for 624 Alihilani St 16 of 39 Listing Image for 624 Alihilani St 17 of 39 Listing Image for 624 Alihilani St 18 of 39 Listing Image for 624 Alihilani St 19 of 39 Listing Image for 624 Alihilani St 20 of 39 Listing Image for 624 Alihilani St 21 of 39 Listing Image for 624 Alihilani St 22 of 39 Listing Image for 624 Alihilani St 23 of 39 Listing Image for 624 Alihilani St 24 of 39 Listing Image for 624 Alihilani St 25 of 39 Listing Image for 624 Alihilani St 26 of 39 Listing Image for 624 Alihilani St 27 of 39 Listing Image for 624 Alihilani St 28 of 39 Listing Image for 624 Alihilani St 29 of 39 Listing Image for 624 Alihilani St 30 of 39 Listing Image for 624 Alihilani St 31 of 39 Listing Image for 624 Alihilani St 32 of 39 Listing Image for 624 Alihilani St 33 of 39 Listing Image for 624 Alihilani St 34 of 39 Listing Image for 624 Alihilani St 35 of 39 Listing Image for 624 Alihilani St 36 of 39 Listing Image for 624 Alihilani St 37 of 39 Listing Image for 624 Alihilani St 38 of 39 Listing Image for 624 Alihilani St 39 of 39

$1,199,000

Waiehu Terrace

624 Alihilani St, Wailuku

3 Beds 2 Baths 1,248 SqFt Residential MLS® # 409446

Days on Market: 140

Real Broker Cell: 808-214-8111

Short Term Rental
Listing Image for 500 Kapalua Dr 14v2 1 of 45 Listing Image for 500 Kapalua Dr 14v2 2 of 45 Listing Image for 500 Kapalua Dr 14v2 3 of 45 Listing Image for 500 Kapalua Dr 14v2 4 of 45 Listing Image for 500 Kapalua Dr 14v2 5 of 45 Listing Image for 500 Kapalua Dr 14v2 6 of 45 Listing Image for 500 Kapalua Dr 14v2 7 of 45 Listing Image for 500 Kapalua Dr 14v2 8 of 45 Listing Image for 500 Kapalua Dr 14v2 9 of 45 Listing Image for 500 Kapalua Dr 14v2 10 of 45 Listing Image for 500 Kapalua Dr 14v2 11 of 45 Listing Image for 500 Kapalua Dr 14v2 12 of 45 Listing Image for 500 Kapalua Dr 14v2 13 of 45 Listing Image for 500 Kapalua Dr 14v2 14 of 45 Listing Image for 500 Kapalua Dr 14v2 15 of 45 Listing Image for 500 Kapalua Dr 14v2 16 of 45 Listing Image for 500 Kapalua Dr 14v2 17 of 45 Listing Image for 500 Kapalua Dr 14v2 18 of 45 Listing Image for 500 Kapalua Dr 14v2 19 of 45 Listing Image for 500 Kapalua Dr 14v2 20 of 45 Listing Image for 500 Kapalua Dr 14v2 21 of 45 Listing Image for 500 Kapalua Dr 14v2 22 of 45 Listing Image for 500 Kapalua Dr 14v2 23 of 45 Listing Image for 500 Kapalua Dr 14v2 24 of 45 Listing Image for 500 Kapalua Dr 14v2 25 of 45 Listing Image for 500 Kapalua Dr 14v2 26 of 45 Listing Image for 500 Kapalua Dr 14v2 27 of 45 Listing Image for 500 Kapalua Dr 14v2 28 of 45 Listing Image for 500 Kapalua Dr 14v2 29 of 45 Listing Image for 500 Kapalua Dr 14v2 30 of 45 Listing Image for 500 Kapalua Dr 14v2 31 of 45 Listing Image for 500 Kapalua Dr 14v2 32 of 45 Listing Image for 500 Kapalua Dr 14v2 33 of 45 Listing Image for 500 Kapalua Dr 14v2 34 of 45 Listing Image for 500 Kapalua Dr 14v2 35 of 45 Listing Image for 500 Kapalua Dr 14v2 36 of 45 Listing Image for 500 Kapalua Dr 14v2 37 of 45 Listing Image for 500 Kapalua Dr 14v2 38 of 45 Listing Image for 500 Kapalua Dr 14v2 39 of 45 Listing Image for 500 Kapalua Dr 14v2 40 of 45 Listing Image for 500 Kapalua Dr 14v2 41 of 45 Listing Image for 500 Kapalua Dr 14v2 42 of 45 Listing Image for 500 Kapalua Dr 14v2 43 of 45 Listing Image for 500 Kapalua Dr 14v2 44 of 45 Listing Image for 500 Kapalua Dr 14v2 45 of 45

$875,000

↓ $20,000

Kapalua Golf Villas 14V2

500 Kapalua Dr 14v2, Kapalua

1 Bed 1.5 Baths 899 SqFt Residential MLS® # 409443

Days on Market: 140

Platinum Properties Hawaii,LLC

Buying Real Estate on Maui

Buying Real Estate on Maui

Read Evan's complete guide to buying a home or condo on Maui.

Read the Guide
Listing Image for 45 Hoku Puhipaka St 1 of 29 Listing Image for 45 Hoku Puhipaka St 2 of 29 Listing Image for 45 Hoku Puhipaka St 3 of 29 Listing Image for 45 Hoku Puhipaka St 4 of 29 Listing Image for 45 Hoku Puhipaka St 5 of 29 Listing Image for 45 Hoku Puhipaka St 6 of 29 Listing Image for 45 Hoku Puhipaka St 7 of 29 Listing Image for 45 Hoku Puhipaka St 8 of 29 Listing Image for 45 Hoku Puhipaka St 9 of 29 Listing Image for 45 Hoku Puhipaka St 10 of 29 Listing Image for 45 Hoku Puhipaka St 11 of 29 Listing Image for 45 Hoku Puhipaka St 12 of 29 Listing Image for 45 Hoku Puhipaka St 13 of 29 Listing Image for 45 Hoku Puhipaka St 14 of 29 Listing Image for 45 Hoku Puhipaka St 15 of 29 Listing Image for 45 Hoku Puhipaka St 16 of 29 Listing Image for 45 Hoku Puhipaka St 17 of 29 Listing Image for 45 Hoku Puhipaka St 18 of 29 Listing Image for 45 Hoku Puhipaka St 19 of 29 Listing Image for 45 Hoku Puhipaka St 20 of 29 Listing Image for 45 Hoku Puhipaka St 21 of 29 Listing Image for 45 Hoku Puhipaka St 22 of 29 Listing Image for 45 Hoku Puhipaka St 23 of 29 Listing Image for 45 Hoku Puhipaka St 24 of 29 Listing Image for 45 Hoku Puhipaka St 25 of 29 Listing Image for 45 Hoku Puhipaka St 26 of 29 Listing Image for 45 Hoku Puhipaka St 27 of 29 Listing Image for 45 Hoku Puhipaka St 28 of 29 Listing Image for 45 Hoku Puhipaka St 29 of 29

$1,150,000

Maui Lani

45 Hoku Puhipaka St, Kahului

3 Beds 2 Baths 1,732 SqFt Residential MLS® # 409436

Days on Market: 140

Coldwell Banker Island Prop-Ku Cell: 808-269-2507

Listing Image for 859 Kai Hele Ku #a St 1 of 25 Listing Image for 859 Kai Hele Ku #a St 2 of 25 Listing Image for 859 Kai Hele Ku #a St 3 of 25 Listing Image for 859 Kai Hele Ku #a St 4 of 25 Listing Image for 859 Kai Hele Ku #a St 5 of 25 Listing Image for 859 Kai Hele Ku #a St 6 of 25 Listing Image for 859 Kai Hele Ku #a St 7 of 25 Listing Image for 859 Kai Hele Ku #a St 8 of 25 Listing Image for 859 Kai Hele Ku #a St 9 of 25 Listing Image for 859 Kai Hele Ku #a St 10 of 25 Listing Image for 859 Kai Hele Ku #a St 11 of 25 Listing Image for 859 Kai Hele Ku #a St 12 of 25 Listing Image for 859 Kai Hele Ku #a St 13 of 25 Listing Image for 859 Kai Hele Ku #a St 14 of 25 Listing Image for 859 Kai Hele Ku #a St 15 of 25 Listing Image for 859 Kai Hele Ku #a St 16 of 25 Listing Image for 859 Kai Hele Ku #a St 17 of 25 Listing Image for 859 Kai Hele Ku #a St 18 of 25 Listing Image for 859 Kai Hele Ku #a St 19 of 25 Listing Image for 859 Kai Hele Ku #a St 20 of 25 Listing Image for 859 Kai Hele Ku #a St 21 of 25 Listing Image for 859 Kai Hele Ku #a St 22 of 25 Listing Image for 859 Kai Hele Ku #a St 23 of 25 Listing Image for 859 Kai Hele Ku #a St 24 of 25 Listing Image for 859 Kai Hele Ku #a St 25 of 25

$3,915,000

↓ $5,000

Lahaina

859 Kai Hele Ku #a St, Lahaina

4 Beds 4 Baths 2,900 SqFt Residential MLS® # 409430

Days on Market: 147

Berkshire Hathaway Maui Prop-L Cell: 808-280-7061

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

$12,900,000

↑ $400,000

Kapalua

8 Kapalua Pl, Kapalua

5 Beds 7.5 Baths 10,152 SqFt Residential MLS® # 409428

Days on Market: 141

Keller Williams Realty Maui-L Cell: 808-385-2918

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Apply for a Home Equity Loan

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

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

Recent Sales on Maui

Sold
Closed: 06/01/2026
Listing Image for 120 Unahe Pl Lot 3-a 1 of 5 Listing Image for 120 Unahe Pl Lot 3-a 2 of 5 Listing Image for 120 Unahe Pl Lot 3-a 3 of 5 Listing Image for 120 Unahe Pl Lot 3-a 4 of 5 Listing Image for 120 Unahe Pl Lot 3-a 5 of 5

$1,530,000

The Parkways at Maui Lani

120 Unahe Pl Lot 3-a, Kahului

5 Beds 3.5 Baths 2,429 SqFt Residential MLS® # 408157 Date Sold: June 1, 2026
Sold
Closed: 12/17/2025
24 One Hali Ln 7-201, Kihei

$830,000

Kai Ani Village 7-201

24 One Hali Ln 7-201, Kihei

2 Beds 2 Baths 1,032 SqFt Residential MLS® # 408151 Date Sold: December 17, 2025
Sold
Closed: 04/23/2026
Listing Image for 2481 Kaanapali Pkwy 821/823 1 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 2 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 3 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 4 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 5 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 6 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 7 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 8 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 9 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 10 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 11 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 12 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 13 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 14 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 15 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 16 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 17 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 18 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 19 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 20 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 21 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 22 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 23 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 24 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 25 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 26 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 27 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 28 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 29 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 30 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 31 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 32 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 33 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 34 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 35 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 36 of 37 Listing Image for 2481 Kaanapali Pkwy 821/823 37 of 37

$2,400,000

↓ $295,000

Whaler 821/823

2481 Kaanapali Pkwy 821/823, Kaanapali

2 Beds 2 Baths 1,444 SqFt Residential MLS® # 408148 Date Sold: April 23, 2026
Sold
Closed: 06/08/2026
Listing Image for 4365 Lower Honoapiilani Rd 520 1 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 2 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 3 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 4 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 5 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 6 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 7 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 8 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 9 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 10 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 11 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 12 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 13 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 14 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 15 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 16 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 17 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 18 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 19 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 20 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 21 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 22 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 23 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 24 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 25 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 26 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 27 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 28 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 29 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 30 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 31 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 32 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 33 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 34 of 35 Listing Image for 4365 Lower Honoapiilani Rd 520 35 of 35

$800,000

↓ $95,000

Royal Kahana 520

4365 Lower Honoapiilani Rd 520, Napili/Kahana/Honokowai

2 Beds 2 Baths 1,141 SqFt Residential MLS® # 408147 Date Sold: June 8, 2026
Buying Real Estate on Maui

Buying Real Estate on Maui

Read Evan's complete guide to buying a home or condo on Maui.

Read the Guide
Sold
Closed: 06/12/2026
Listing Image for 1065 Umeke St 106 1 of 36 Listing Image for 1065 Umeke St 106 2 of 36 Listing Image for 1065 Umeke St 106 3 of 36 Listing Image for 1065 Umeke St 106 4 of 36 Listing Image for 1065 Umeke St 106 5 of 36 Listing Image for 1065 Umeke St 106 6 of 36 Listing Image for 1065 Umeke St 106 7 of 36 Listing Image for 1065 Umeke St 106 8 of 36 Listing Image for 1065 Umeke St 106 9 of 36 Listing Image for 1065 Umeke St 106 10 of 36 Listing Image for 1065 Umeke St 106 11 of 36 Listing Image for 1065 Umeke St 106 12 of 36 Listing Image for 1065 Umeke St 106 13 of 36 Listing Image for 1065 Umeke St 106 14 of 36 Listing Image for 1065 Umeke St 106 15 of 36 Listing Image for 1065 Umeke St 106 16 of 36 Listing Image for 1065 Umeke St 106 17 of 36 Listing Image for 1065 Umeke St 106 18 of 36 Listing Image for 1065 Umeke St 106 19 of 36 Listing Image for 1065 Umeke St 106 20 of 36 Listing Image for 1065 Umeke St 106 21 of 36 Listing Image for 1065 Umeke St 106 22 of 36 Listing Image for 1065 Umeke St 106 23 of 36 Listing Image for 1065 Umeke St 106 24 of 36 Listing Image for 1065 Umeke St 106 25 of 36 Listing Image for 1065 Umeke St 106 26 of 36 Listing Image for 1065 Umeke St 106 27 of 36 Listing Image for 1065 Umeke St 106 28 of 36 Listing Image for 1065 Umeke St 106 29 of 36 Listing Image for 1065 Umeke St 106 30 of 36 Listing Image for 1065 Umeke St 106 31 of 36 Listing Image for 1065 Umeke St 106 32 of 36 Listing Image for 1065 Umeke St 106 33 of 36 Listing Image for 1065 Umeke St 106 34 of 36 Listing Image for 1065 Umeke St 106 35 of 36 Listing Image for 1065 Umeke St 106 36 of 36

$1,985,000

Hokulani Golf Villas 106

1065 Umeke St 106, Kihei

2 Beds 2 Baths 1,902 SqFt Residential MLS® # 407240 Date Sold: June 12, 2026
Sold
Closed: 07/20/2026
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$950,000

↓ $10,000

Milo Court at Kehalani 38

223 Lau Oliwa Loop 38, Wailuku

3 Beds 2.5 Baths 1,457 SqFt Residential MLS® # 408145 Date Sold: July 20, 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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