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

Sort by:
Listing Image for 7505 Makena Rd 1 of 50 Listing Image for 7505 Makena Rd 2 of 50 Listing Image for 7505 Makena Rd 3 of 50 Listing Image for 7505 Makena Rd 4 of 50 Listing Image for 7505 Makena Rd 5 of 50 Listing Image for 7505 Makena Rd 6 of 50 Listing Image for 7505 Makena Rd 7 of 50 Listing Image for 7505 Makena Rd 8 of 50 Listing Image for 7505 Makena Rd 9 of 50 Listing Image for 7505 Makena Rd 10 of 50 Listing Image for 7505 Makena Rd 11 of 50 Listing Image for 7505 Makena Rd 12 of 50 Listing Image for 7505 Makena Rd 13 of 50 Listing Image for 7505 Makena Rd 14 of 50 Listing Image for 7505 Makena Rd 15 of 50 Listing Image for 7505 Makena Rd 16 of 50 Listing Image for 7505 Makena Rd 17 of 50 Listing Image for 7505 Makena Rd 18 of 50 Listing Image for 7505 Makena Rd 19 of 50 Listing Image for 7505 Makena Rd 20 of 50 Listing Image for 7505 Makena Rd 21 of 50 Listing Image for 7505 Makena Rd 22 of 50 Listing Image for 7505 Makena Rd 23 of 50 Listing Image for 7505 Makena Rd 24 of 50 Listing Image for 7505 Makena Rd 25 of 50 Listing Image for 7505 Makena Rd 26 of 50 Listing Image for 7505 Makena Rd 27 of 50 Listing Image for 7505 Makena Rd 28 of 50 Listing Image for 7505 Makena Rd 29 of 50 Listing Image for 7505 Makena Rd 30 of 50 Listing Image for 7505 Makena Rd 31 of 50 Listing Image for 7505 Makena Rd 32 of 50 Listing Image for 7505 Makena Rd 33 of 50 Listing Image for 7505 Makena Rd 34 of 50 Listing Image for 7505 Makena Rd 35 of 50 Listing Image for 7505 Makena Rd 36 of 50 Listing Image for 7505 Makena Rd 37 of 50 Listing Image for 7505 Makena Rd 38 of 50 Listing Image for 7505 Makena Rd 39 of 50 Listing Image for 7505 Makena Rd 40 of 50 Listing Image for 7505 Makena Rd 41 of 50 Listing Image for 7505 Makena Rd 42 of 50 Listing Image for 7505 Makena Rd 43 of 50 Listing Image for 7505 Makena Rd 44 of 50 Listing Image for 7505 Makena Rd 45 of 50 Listing Image for 7505 Makena Rd 46 of 50 Listing Image for 7505 Makena Rd 47 of 50 Listing Image for 7505 Makena Rd 48 of 50 Listing Image for 7505 Makena Rd 49 of 50 Listing Image for 7505 Makena Rd 50 of 50

$26,500,000

Makena

7505 Makena Rd, Wailea/Makena

6 Beds 6 Baths 8,664 SqFt Residential MLS® # 409734

Days on Market: 112

Compass-W

Listing Image for 50 Puu Anoano St 3404 1 of 47 Listing Image for 50 Puu Anoano St 3404 2 of 47 Listing Image for 50 Puu Anoano St 3404 3 of 47 Listing Image for 50 Puu Anoano St 3404 4 of 47 Listing Image for 50 Puu Anoano St 3404 5 of 47 Listing Image for 50 Puu Anoano St 3404 6 of 47 Listing Image for 50 Puu Anoano St 3404 7 of 47 Listing Image for 50 Puu Anoano St 3404 8 of 47 Listing Image for 50 Puu Anoano St 3404 9 of 47 Listing Image for 50 Puu Anoano St 3404 10 of 47 Listing Image for 50 Puu Anoano St 3404 11 of 47 Listing Image for 50 Puu Anoano St 3404 12 of 47 Listing Image for 50 Puu Anoano St 3404 13 of 47 Listing Image for 50 Puu Anoano St 3404 14 of 47 Listing Image for 50 Puu Anoano St 3404 15 of 47 Listing Image for 50 Puu Anoano St 3404 16 of 47 Listing Image for 50 Puu Anoano St 3404 17 of 47 Listing Image for 50 Puu Anoano St 3404 18 of 47 Listing Image for 50 Puu Anoano St 3404 19 of 47 Listing Image for 50 Puu Anoano St 3404 20 of 47 Listing Image for 50 Puu Anoano St 3404 21 of 47 Listing Image for 50 Puu Anoano St 3404 22 of 47 Listing Image for 50 Puu Anoano St 3404 23 of 47 Listing Image for 50 Puu Anoano St 3404 24 of 47 Listing Image for 50 Puu Anoano St 3404 25 of 47 Listing Image for 50 Puu Anoano St 3404 26 of 47 Listing Image for 50 Puu Anoano St 3404 27 of 47 Listing Image for 50 Puu Anoano St 3404 28 of 47 Listing Image for 50 Puu Anoano St 3404 29 of 47 Listing Image for 50 Puu Anoano St 3404 30 of 47 Listing Image for 50 Puu Anoano St 3404 31 of 47 Listing Image for 50 Puu Anoano St 3404 32 of 47 Listing Image for 50 Puu Anoano St 3404 33 of 47 Listing Image for 50 Puu Anoano St 3404 34 of 47 Listing Image for 50 Puu Anoano St 3404 35 of 47 Listing Image for 50 Puu Anoano St 3404 36 of 47 Listing Image for 50 Puu Anoano St 3404 37 of 47 Listing Image for 50 Puu Anoano St 3404 38 of 47 Listing Image for 50 Puu Anoano St 3404 39 of 47 Listing Image for 50 Puu Anoano St 3404 40 of 47 Listing Image for 50 Puu Anoano St 3404 41 of 47 Listing Image for 50 Puu Anoano St 3404 42 of 47 Listing Image for 50 Puu Anoano St 3404 43 of 47 Listing Image for 50 Puu Anoano St 3404 44 of 47 Listing Image for 50 Puu Anoano St 3404 45 of 47 Listing Image for 50 Puu Anoano St 3404 46 of 47 Listing Image for 50 Puu Anoano St 3404 47 of 47

$1,999,000

Masters 3404

50 Puu Anoano St 3404, Kaanapali

2 Beds 2.5 Baths 1,850 SqFt Residential MLS® # 409731

Days on Market: 113

Berkshire Hathaway Maui Prop-L

Short Term Rental
Listing Image for 145 N Kihei Rd Ph23 1 of 50 Listing Image for 145 N Kihei Rd Ph23 2 of 50 Listing Image for 145 N Kihei Rd Ph23 3 of 50 Listing Image for 145 N Kihei Rd Ph23 4 of 50 Listing Image for 145 N Kihei Rd Ph23 5 of 50 Listing Image for 145 N Kihei Rd Ph23 6 of 50 Listing Image for 145 N Kihei Rd Ph23 7 of 50 Listing Image for 145 N Kihei Rd Ph23 8 of 50 Listing Image for 145 N Kihei Rd Ph23 9 of 50 Listing Image for 145 N Kihei Rd Ph23 10 of 50 Listing Image for 145 N Kihei Rd Ph23 11 of 50 Listing Image for 145 N Kihei Rd Ph23 12 of 50 Listing Image for 145 N Kihei Rd Ph23 13 of 50 Listing Image for 145 N Kihei Rd Ph23 14 of 50 Listing Image for 145 N Kihei Rd Ph23 15 of 50 Listing Image for 145 N Kihei Rd Ph23 16 of 50 Listing Image for 145 N Kihei Rd Ph23 17 of 50 Listing Image for 145 N Kihei Rd Ph23 18 of 50 Listing Image for 145 N Kihei Rd Ph23 19 of 50 Listing Image for 145 N Kihei Rd Ph23 20 of 50 Listing Image for 145 N Kihei Rd Ph23 21 of 50 Listing Image for 145 N Kihei Rd Ph23 22 of 50 Listing Image for 145 N Kihei Rd Ph23 23 of 50 Listing Image for 145 N Kihei Rd Ph23 24 of 50 Listing Image for 145 N Kihei Rd Ph23 25 of 50 Listing Image for 145 N Kihei Rd Ph23 26 of 50 Listing Image for 145 N Kihei Rd Ph23 27 of 50 Listing Image for 145 N Kihei Rd Ph23 28 of 50 Listing Image for 145 N Kihei Rd Ph23 29 of 50 Listing Image for 145 N Kihei Rd Ph23 30 of 50 Listing Image for 145 N Kihei Rd Ph23 31 of 50 Listing Image for 145 N Kihei Rd Ph23 32 of 50 Listing Image for 145 N Kihei Rd Ph23 33 of 50 Listing Image for 145 N Kihei Rd Ph23 34 of 50 Listing Image for 145 N Kihei Rd Ph23 35 of 50 Listing Image for 145 N Kihei Rd Ph23 36 of 50 Listing Image for 145 N Kihei Rd Ph23 37 of 50 Listing Image for 145 N Kihei Rd Ph23 38 of 50 Listing Image for 145 N Kihei Rd Ph23 39 of 50 Listing Image for 145 N Kihei Rd Ph23 40 of 50 Listing Image for 145 N Kihei Rd Ph23 41 of 50 Listing Image for 145 N Kihei Rd Ph23 42 of 50 Listing Image for 145 N Kihei Rd Ph23 43 of 50 Listing Image for 145 N Kihei Rd Ph23 44 of 50 Listing Image for 145 N Kihei Rd Ph23 45 of 50 Listing Image for 145 N Kihei Rd Ph23 46 of 50 Listing Image for 145 N Kihei Rd Ph23 47 of 50 Listing Image for 145 N Kihei Rd Ph23 48 of 50 Listing Image for 145 N Kihei Rd Ph23 49 of 50 Listing Image for 145 N Kihei Rd Ph23 50 of 50

$879,000

Sugar Beach Resort PH23

145 N Kihei Rd Ph23, Kihei

1 Bed 1 Bath 613 SqFt Residential MLS® # 409726

Days on Market: 112

Coldwell Banker Island Prop-Ku Cell: 808-850-1662

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

$2,350,000

↓ $45,000

Maluhia Country Ranches

18 Lahaole Pl, Wailuku

3 Beds 2 Baths 2,591 SqFt Residential MLS® # 409716

Days on Market: 112

Coldwell Banker Island Prop(S) Cell: 808-891-8989

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
Short Term Rental
Listing Image for 4365 Lower Honoapiilani Rd 610 1 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 2 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 3 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 4 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 5 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 6 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 7 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 8 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 9 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 10 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 11 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 12 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 13 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 14 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 15 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 16 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 17 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 18 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 19 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 20 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 21 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 22 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 23 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 24 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 25 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 26 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 27 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 28 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 29 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 30 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 31 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 32 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 33 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 34 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 35 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 36 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 37 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 38 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 39 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 40 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 41 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 42 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 43 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 44 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 45 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 46 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 47 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 48 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 49 of 50 Listing Image for 4365 Lower Honoapiilani Rd 610 50 of 50

$1,495,000

↓ $155,000

Royal Kahana 610

4365 Lower Honoapiilani Rd 610, Napili/Kahana/Honokowai

2 Beds 2.5 Baths 1,287 SqFt Residential MLS® # 409707

Days on Market: 113

Compass Cell: 808-281-2178

Listing Image for 51 Kapohue Rd 1 of 50 Listing Image for 51 Kapohue Rd 2 of 50 Listing Image for 51 Kapohue Rd 3 of 50 Listing Image for 51 Kapohue Rd 4 of 50 Listing Image for 51 Kapohue Rd 5 of 50 Listing Image for 51 Kapohue Rd 6 of 50 Listing Image for 51 Kapohue Rd 7 of 50 Listing Image for 51 Kapohue Rd 8 of 50 Listing Image for 51 Kapohue Rd 9 of 50 Listing Image for 51 Kapohue Rd 10 of 50 Listing Image for 51 Kapohue Rd 11 of 50 Listing Image for 51 Kapohue Rd 12 of 50 Listing Image for 51 Kapohue Rd 13 of 50 Listing Image for 51 Kapohue Rd 14 of 50 Listing Image for 51 Kapohue Rd 15 of 50 Listing Image for 51 Kapohue Rd 16 of 50 Listing Image for 51 Kapohue Rd 17 of 50 Listing Image for 51 Kapohue Rd 18 of 50 Listing Image for 51 Kapohue Rd 19 of 50 Listing Image for 51 Kapohue Rd 20 of 50 Listing Image for 51 Kapohue Rd 21 of 50 Listing Image for 51 Kapohue Rd 22 of 50 Listing Image for 51 Kapohue Rd 23 of 50 Listing Image for 51 Kapohue Rd 24 of 50 Listing Image for 51 Kapohue Rd 25 of 50 Listing Image for 51 Kapohue Rd 26 of 50 Listing Image for 51 Kapohue Rd 27 of 50 Listing Image for 51 Kapohue Rd 28 of 50 Listing Image for 51 Kapohue Rd 29 of 50 Listing Image for 51 Kapohue Rd 30 of 50 Listing Image for 51 Kapohue Rd 31 of 50 Listing Image for 51 Kapohue Rd 32 of 50 Listing Image for 51 Kapohue Rd 33 of 50 Listing Image for 51 Kapohue Rd 34 of 50 Listing Image for 51 Kapohue Rd 35 of 50 Listing Image for 51 Kapohue Rd 36 of 50 Listing Image for 51 Kapohue Rd 37 of 50 Listing Image for 51 Kapohue Rd 38 of 50 Listing Image for 51 Kapohue Rd 39 of 50 Listing Image for 51 Kapohue Rd 40 of 50 Listing Image for 51 Kapohue Rd 41 of 50 Listing Image for 51 Kapohue Rd 42 of 50 Listing Image for 51 Kapohue Rd 43 of 50 Listing Image for 51 Kapohue Rd 44 of 50 Listing Image for 51 Kapohue Rd 45 of 50 Listing Image for 51 Kapohue Rd 46 of 50 Listing Image for 51 Kapohue Rd 47 of 50 Listing Image for 51 Kapohue Rd 48 of 50 Listing Image for 51 Kapohue Rd 49 of 50 Listing Image for 51 Kapohue Rd 50 of 50

$4,700,000

Hana

51 Kapohue Rd, Hana

3 Beds 3.5 Baths 3,295 SqFt Residential MLS® # 409698

Days on Market: 114

Compass-W

Listing Image for 130 Kai Malina Pkwy Sr409 1 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 2 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 3 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 4 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 5 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 6 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 7 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 8 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 9 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 10 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 11 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 12 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 13 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 14 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 15 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 16 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 17 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 18 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 19 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 20 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 21 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 22 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 23 of 24 Listing Image for 130 Kai Malina Pkwy Sr409 24 of 24

$3,200,000

Honua Kai - Hoku Lani SR409

130 Kai Malina Pkwy Sr409, Kaanapali

2 Beds 2 Baths 1,300 SqFt Residential MLS® # 409696

Days on Market: 115

Susan Jackson Real Estate Cell: 865-206-1234

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: 01/16/2026
277 Pule Pl, Wailuku

$770,000

Wailuku

277 Pule Pl, Wailuku

2 Beds 2 Baths 881 SqFt Residential MLS® # 408446 Date Sold: January 16, 2026
Sold
Closed: 04/07/2026
Listing Image for 64 Door Of Faith Rd 1 of 31 Listing Image for 64 Door Of Faith Rd 2 of 31 Listing Image for 64 Door Of Faith Rd 3 of 31 Listing Image for 64 Door Of Faith Rd 4 of 31 Listing Image for 64 Door Of Faith Rd 5 of 31 Listing Image for 64 Door Of Faith Rd 6 of 31 Listing Image for 64 Door Of Faith Rd 7 of 31 Listing Image for 64 Door Of Faith Rd 8 of 31 Listing Image for 64 Door Of Faith Rd 9 of 31 Listing Image for 64 Door Of Faith Rd 10 of 31 Listing Image for 64 Door Of Faith Rd 11 of 31 Listing Image for 64 Door Of Faith Rd 12 of 31 Listing Image for 64 Door Of Faith Rd 13 of 31 Listing Image for 64 Door Of Faith Rd 14 of 31 Listing Image for 64 Door Of Faith Rd 15 of 31 Listing Image for 64 Door Of Faith Rd 16 of 31 Listing Image for 64 Door Of Faith Rd 17 of 31 Listing Image for 64 Door Of Faith Rd 18 of 31 Listing Image for 64 Door Of Faith Rd 19 of 31 Listing Image for 64 Door Of Faith Rd 20 of 31 Listing Image for 64 Door Of Faith Rd 21 of 31 Listing Image for 64 Door Of Faith Rd 22 of 31 Listing Image for 64 Door Of Faith Rd 23 of 31 Listing Image for 64 Door Of Faith Rd 24 of 31 Listing Image for 64 Door Of Faith Rd 25 of 31 Listing Image for 64 Door Of Faith Rd 26 of 31 Listing Image for 64 Door Of Faith Rd 27 of 31 Listing Image for 64 Door Of Faith Rd 28 of 31 Listing Image for 64 Door Of Faith Rd 29 of 31 Listing Image for 64 Door Of Faith Rd 30 of 31 Listing Image for 64 Door Of Faith Rd 31 of 31

$1,180,000

Huelo

64 Door Of Faith Rd, Haiku

4 Beds 2 Baths 1,830 SqFt Residential MLS® # 408443 Date Sold: April 7, 2026
Sold
Closed: 01/16/2026
91 Maiaku St 172, Makawao/Olinda/Haliimaile

$1,395,000

Hokuula

91 Maiaku St 172, Makawao/Olinda/Haliimaile

4 Beds 3 Baths 1,456 SqFt Residential MLS® # 408440 Date Sold: January 16, 2026
Sold
Closed: 03/25/2026
Listing Image for 2575 S Kihei Rd P202 1 of 34 Listing Image for 2575 S Kihei Rd P202 2 of 34 Listing Image for 2575 S Kihei Rd P202 3 of 34 Listing Image for 2575 S Kihei Rd P202 4 of 34 Listing Image for 2575 S Kihei Rd P202 5 of 34 Listing Image for 2575 S Kihei Rd P202 6 of 34 Listing Image for 2575 S Kihei Rd P202 7 of 34 Listing Image for 2575 S Kihei Rd P202 8 of 34 Listing Image for 2575 S Kihei Rd P202 9 of 34 Listing Image for 2575 S Kihei Rd P202 10 of 34 Listing Image for 2575 S Kihei Rd P202 11 of 34 Listing Image for 2575 S Kihei Rd P202 12 of 34 Listing Image for 2575 S Kihei Rd P202 13 of 34 Listing Image for 2575 S Kihei Rd P202 14 of 34 Listing Image for 2575 S Kihei Rd P202 15 of 34 Listing Image for 2575 S Kihei Rd P202 16 of 34 Listing Image for 2575 S Kihei Rd P202 17 of 34 Listing Image for 2575 S Kihei Rd P202 18 of 34 Listing Image for 2575 S Kihei Rd P202 19 of 34 Listing Image for 2575 S Kihei Rd P202 20 of 34 Listing Image for 2575 S Kihei Rd P202 21 of 34 Listing Image for 2575 S Kihei Rd P202 22 of 34 Listing Image for 2575 S Kihei Rd P202 23 of 34 Listing Image for 2575 S Kihei Rd P202 24 of 34 Listing Image for 2575 S Kihei Rd P202 25 of 34 Listing Image for 2575 S Kihei Rd P202 26 of 34 Listing Image for 2575 S Kihei Rd P202 27 of 34 Listing Image for 2575 S Kihei Rd P202 28 of 34 Listing Image for 2575 S Kihei Rd P202 29 of 34 Listing Image for 2575 S Kihei Rd P202 30 of 34 Listing Image for 2575 S Kihei Rd P202 31 of 34 Listing Image for 2575 S Kihei Rd P202 32 of 34 Listing Image for 2575 S Kihei Rd P202 33 of 34 Listing Image for 2575 S Kihei Rd P202 34 of 34

$975,000

Maui Banyan P202

2575 S Kihei Rd P202, Kihei

2 Beds 2 Baths 900 SqFt Residential MLS® # 408435 Date Sold: March 25, 2026
Sold
Closed: 03/30/2026
Listing Image for 50 Nohea Kai Dr 1-304 1 of 40 Listing Image for 50 Nohea Kai Dr 1-304 2 of 40 Listing Image for 50 Nohea Kai Dr 1-304 3 of 40 Listing Image for 50 Nohea Kai Dr 1-304 4 of 40 Listing Image for 50 Nohea Kai Dr 1-304 5 of 40 Listing Image for 50 Nohea Kai Dr 1-304 6 of 40 Listing Image for 50 Nohea Kai Dr 1-304 7 of 40 Listing Image for 50 Nohea Kai Dr 1-304 8 of 40 Listing Image for 50 Nohea Kai Dr 1-304 9 of 40 Listing Image for 50 Nohea Kai Dr 1-304 10 of 40 Listing Image for 50 Nohea Kai Dr 1-304 11 of 40 Listing Image for 50 Nohea Kai Dr 1-304 12 of 40 Listing Image for 50 Nohea Kai Dr 1-304 13 of 40 Listing Image for 50 Nohea Kai Dr 1-304 14 of 40 Listing Image for 50 Nohea Kai Dr 1-304 15 of 40 Listing Image for 50 Nohea Kai Dr 1-304 16 of 40 Listing Image for 50 Nohea Kai Dr 1-304 17 of 40 Listing Image for 50 Nohea Kai Dr 1-304 18 of 40 Listing Image for 50 Nohea Kai Dr 1-304 19 of 40 Listing Image for 50 Nohea Kai Dr 1-304 20 of 40 Listing Image for 50 Nohea Kai Dr 1-304 21 of 40 Listing Image for 50 Nohea Kai Dr 1-304 22 of 40 Listing Image for 50 Nohea Kai Dr 1-304 23 of 40 Listing Image for 50 Nohea Kai Dr 1-304 24 of 40 Listing Image for 50 Nohea Kai Dr 1-304 25 of 40 Listing Image for 50 Nohea Kai Dr 1-304 26 of 40 Listing Image for 50 Nohea Kai Dr 1-304 27 of 40 Listing Image for 50 Nohea Kai Dr 1-304 28 of 40 Listing Image for 50 Nohea Kai Dr 1-304 29 of 40 Listing Image for 50 Nohea Kai Dr 1-304 30 of 40 Listing Image for 50 Nohea Kai Dr 1-304 31 of 40 Listing Image for 50 Nohea Kai Dr 1-304 32 of 40 Listing Image for 50 Nohea Kai Dr 1-304 33 of 40 Listing Image for 50 Nohea Kai Dr 1-304 34 of 40 Listing Image for 50 Nohea Kai Dr 1-304 35 of 40 Listing Image for 50 Nohea Kai Dr 1-304 36 of 40 Listing Image for 50 Nohea Kai Dr 1-304 37 of 40 Listing Image for 50 Nohea Kai Dr 1-304 38 of 40 Listing Image for 50 Nohea Kai Dr 1-304 39 of 40 Listing Image for 50 Nohea Kai Dr 1-304 40 of 40

$2,850,000

Kaanapali Alii 1-304

50 Nohea Kai Dr 1-304, Kaanapali

2 Beds 2 Baths 1,523 SqFt Residential MLS® # 408436 Date Sold: March 30, 2026
Sold
Closed: 06/30/2026
Listing Image for 245 Kamahao Cir 1 of 37 Listing Image for 245 Kamahao Cir 2 of 37 Listing Image for 245 Kamahao Cir 3 of 37 Listing Image for 245 Kamahao Cir 4 of 37 Listing Image for 245 Kamahao Cir 5 of 37 Listing Image for 245 Kamahao Cir 6 of 37 Listing Image for 245 Kamahao Cir 7 of 37 Listing Image for 245 Kamahao Cir 8 of 37 Listing Image for 245 Kamahao Cir 9 of 37 Listing Image for 245 Kamahao Cir 10 of 37 Listing Image for 245 Kamahao Cir 11 of 37 Listing Image for 245 Kamahao Cir 12 of 37 Listing Image for 245 Kamahao Cir 13 of 37 Listing Image for 245 Kamahao Cir 14 of 37 Listing Image for 245 Kamahao Cir 15 of 37 Listing Image for 245 Kamahao Cir 16 of 37 Listing Image for 245 Kamahao Cir 17 of 37 Listing Image for 245 Kamahao Cir 18 of 37 Listing Image for 245 Kamahao Cir 19 of 37 Listing Image for 245 Kamahao Cir 20 of 37 Listing Image for 245 Kamahao Cir 21 of 37 Listing Image for 245 Kamahao Cir 22 of 37 Listing Image for 245 Kamahao Cir 23 of 37 Listing Image for 245 Kamahao Cir 24 of 37 Listing Image for 245 Kamahao Cir 25 of 37 Listing Image for 245 Kamahao Cir 26 of 37 Listing Image for 245 Kamahao Cir 27 of 37 Listing Image for 245 Kamahao Cir 28 of 37 Listing Image for 245 Kamahao Cir 29 of 37 Listing Image for 245 Kamahao Cir 30 of 37 Listing Image for 245 Kamahao Cir 31 of 37 Listing Image for 245 Kamahao Cir 32 of 37 Listing Image for 245 Kamahao Cir 33 of 37 Listing Image for 245 Kamahao Cir 34 of 37 Listing Image for 245 Kamahao Cir 35 of 37 Listing Image for 245 Kamahao Cir 36 of 37 Listing Image for 245 Kamahao Cir 37 of 37

$1,070,000

↓ $80,000

Waikapu Gardens

245 Kamahao Cir, Wailuku

3 Beds 2.5 Baths 1,452 SqFt Residential MLS® # 408433 Date Sold: June 30, 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.

Provide a valid email address.
Newsletter consent

Posted by Evan Harlow R(S) on

Enjoy this blog post? Click here to subscribe for updates

Tags

Email Send a link to post via Email

Leave A Comment

e.g. yourwebsitename.com
Please note that your email address is kept private upon posting.