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 29 Hua Nui Way 1 of 30 Listing Image for 29 Hua Nui Way 2 of 30 Listing Image for 29 Hua Nui Way 3 of 30 Listing Image for 29 Hua Nui Way 4 of 30 Listing Image for 29 Hua Nui Way 5 of 30 Listing Image for 29 Hua Nui Way 6 of 30 Listing Image for 29 Hua Nui Way 7 of 30 Listing Image for 29 Hua Nui Way 8 of 30 Listing Image for 29 Hua Nui Way 9 of 30 Listing Image for 29 Hua Nui Way 10 of 30 Listing Image for 29 Hua Nui Way 11 of 30 Listing Image for 29 Hua Nui Way 12 of 30 Listing Image for 29 Hua Nui Way 13 of 30 Listing Image for 29 Hua Nui Way 14 of 30 Listing Image for 29 Hua Nui Way 15 of 30 Listing Image for 29 Hua Nui Way 16 of 30 Listing Image for 29 Hua Nui Way 17 of 30 Listing Image for 29 Hua Nui Way 18 of 30 Listing Image for 29 Hua Nui Way 19 of 30 Listing Image for 29 Hua Nui Way 20 of 30 Listing Image for 29 Hua Nui Way 21 of 30 Listing Image for 29 Hua Nui Way 22 of 30 Listing Image for 29 Hua Nui Way 23 of 30 Listing Image for 29 Hua Nui Way 24 of 30 Listing Image for 29 Hua Nui Way 25 of 30 Listing Image for 29 Hua Nui Way 26 of 30 Listing Image for 29 Hua Nui Way 27 of 30 Listing Image for 29 Hua Nui Way 28 of 30 Listing Image for 29 Hua Nui Way 29 of 30 Listing Image for 29 Hua Nui Way 30 of 30

$1,850,000

Napili/Kahana/Honokowai

29 Hua Nui Way, Napili/Kahana/Honokowai

3 Beds 2 Baths 1,600 SqFt Residential MLS® # 410567

Days on Market: 26

Nathalie Mullinix Rlty Universal Inc

Listing Image for 321 Kenolio Rd 1 of 36 Listing Image for 321 Kenolio Rd 2 of 36 Listing Image for 321 Kenolio Rd 3 of 36 Listing Image for 321 Kenolio Rd 4 of 36 Listing Image for 321 Kenolio Rd 5 of 36 Listing Image for 321 Kenolio Rd 6 of 36 Listing Image for 321 Kenolio Rd 7 of 36 Listing Image for 321 Kenolio Rd 8 of 36 Listing Image for 321 Kenolio Rd 9 of 36 Listing Image for 321 Kenolio Rd 10 of 36 Listing Image for 321 Kenolio Rd 11 of 36 Listing Image for 321 Kenolio Rd 12 of 36 Listing Image for 321 Kenolio Rd 13 of 36 Listing Image for 321 Kenolio Rd 14 of 36 Listing Image for 321 Kenolio Rd 15 of 36 Listing Image for 321 Kenolio Rd 16 of 36 Listing Image for 321 Kenolio Rd 17 of 36 Listing Image for 321 Kenolio Rd 18 of 36 Listing Image for 321 Kenolio Rd 19 of 36 Listing Image for 321 Kenolio Rd 20 of 36 Listing Image for 321 Kenolio Rd 21 of 36 Listing Image for 321 Kenolio Rd 22 of 36 Listing Image for 321 Kenolio Rd 23 of 36 Listing Image for 321 Kenolio Rd 24 of 36 Listing Image for 321 Kenolio Rd 25 of 36 Listing Image for 321 Kenolio Rd 26 of 36 Listing Image for 321 Kenolio Rd 27 of 36 Listing Image for 321 Kenolio Rd 28 of 36 Listing Image for 321 Kenolio Rd 29 of 36 Listing Image for 321 Kenolio Rd 30 of 36 Listing Image for 321 Kenolio Rd 31 of 36 Listing Image for 321 Kenolio Rd 32 of 36 Listing Image for 321 Kenolio Rd 33 of 36 Listing Image for 321 Kenolio Rd 34 of 36 Listing Image for 321 Kenolio Rd 35 of 36 Listing Image for 321 Kenolio Rd 36 of 36

$1,049,000

↓ $101,000

Kihei

321 Kenolio Rd, Kihei

3 Beds 1 Bath 925 SqFt Residential MLS® # 410564

Days on Market: 25

Maui Luxury Real Estate LLC

Short Term Rental
Listing Image for 130 Kai Malina Pkwy Nr 325 1 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 2 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 3 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 4 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 5 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 6 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 7 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 8 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 9 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 10 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 11 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 12 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 13 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 14 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 15 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 16 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 17 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 18 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 19 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 20 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 21 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 22 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 23 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 24 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 25 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 26 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 27 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 28 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 29 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 30 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 31 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 32 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 33 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 34 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 35 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 36 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 37 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 38 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 39 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 40 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 41 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 42 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 43 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 44 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 45 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 46 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 47 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 48 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 49 of 50 Listing Image for 130 Kai Malina Pkwy Nr 325 50 of 50

$3,499,888

Honua Kai - Konea NR 325

130 Kai Malina Pkwy Nr 325, Kaanapali

3 Beds 3 Baths 1,610 SqFt Residential MLS® # 410563

Days on Market: 25

Kaanapali Luxury Vacation Rentals

Listing Image for 264 Kawailani Cir 1 of 36 Listing Image for 264 Kawailani Cir 2 of 36 Listing Image for 264 Kawailani Cir 3 of 36 Listing Image for 264 Kawailani Cir 4 of 36 Listing Image for 264 Kawailani Cir 5 of 36 Listing Image for 264 Kawailani Cir 6 of 36 Listing Image for 264 Kawailani Cir 7 of 36 Listing Image for 264 Kawailani Cir 8 of 36 Listing Image for 264 Kawailani Cir 9 of 36 Listing Image for 264 Kawailani Cir 10 of 36 Listing Image for 264 Kawailani Cir 11 of 36 Listing Image for 264 Kawailani Cir 12 of 36 Listing Image for 264 Kawailani Cir 13 of 36 Listing Image for 264 Kawailani Cir 14 of 36 Listing Image for 264 Kawailani Cir 15 of 36 Listing Image for 264 Kawailani Cir 16 of 36 Listing Image for 264 Kawailani Cir 17 of 36 Listing Image for 264 Kawailani Cir 18 of 36 Listing Image for 264 Kawailani Cir 19 of 36 Listing Image for 264 Kawailani Cir 20 of 36 Listing Image for 264 Kawailani Cir 21 of 36 Listing Image for 264 Kawailani Cir 22 of 36 Listing Image for 264 Kawailani Cir 23 of 36 Listing Image for 264 Kawailani Cir 24 of 36 Listing Image for 264 Kawailani Cir 25 of 36 Listing Image for 264 Kawailani Cir 26 of 36 Listing Image for 264 Kawailani Cir 27 of 36 Listing Image for 264 Kawailani Cir 28 of 36 Listing Image for 264 Kawailani Cir 29 of 36 Listing Image for 264 Kawailani Cir 30 of 36 Listing Image for 264 Kawailani Cir 31 of 36 Listing Image for 264 Kawailani Cir 32 of 36 Listing Image for 264 Kawailani Cir 33 of 36 Listing Image for 264 Kawailani Cir 34 of 36 Listing Image for 264 Kawailani Cir 35 of 36 Listing Image for 264 Kawailani Cir 36 of 36

$1,300,000

Piilani Village II

264 Kawailani Cir, Kihei

4 Beds 3 Baths 1,780 SqFt Residential MLS® # 410562

Days on Market: 25

Keller Williams Realty Maui-Ki Cell: 808-371-6475

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

$3,850,000

Hoolei T-1

24 Hoolei Cir T-1, Wailea/Makena

3 Beds 3.5 Baths 3,076 SqFt Residential MLS® # 410561

Days on Market: 25

Keller Williams Realty Maui-Ka Cell: 808-385-0882

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

$1,570,000

Parkways at Maui Lani

48 Lalaha Pl, Kahului

4 Beds 2.5 Baths 2,461 SqFt Residential MLS® # 410560

Days on Market: 26

Pacific Image Properties MannyMila808@gmail.com

View 6 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: 09/08/2026
Listing Image for 66 Kai La Pl 22a 1 of 50 Listing Image for 66 Kai La Pl 22a 2 of 50 Listing Image for 66 Kai La Pl 22a 3 of 50 Listing Image for 66 Kai La Pl 22a 4 of 50 Listing Image for 66 Kai La Pl 22a 5 of 50 Listing Image for 66 Kai La Pl 22a 6 of 50 Listing Image for 66 Kai La Pl 22a 7 of 50 Listing Image for 66 Kai La Pl 22a 8 of 50 Listing Image for 66 Kai La Pl 22a 9 of 50 Listing Image for 66 Kai La Pl 22a 10 of 50 Listing Image for 66 Kai La Pl 22a 11 of 50 Listing Image for 66 Kai La Pl 22a 12 of 50 Listing Image for 66 Kai La Pl 22a 13 of 50 Listing Image for 66 Kai La Pl 22a 14 of 50 Listing Image for 66 Kai La Pl 22a 15 of 50 Listing Image for 66 Kai La Pl 22a 16 of 50 Listing Image for 66 Kai La Pl 22a 17 of 50 Listing Image for 66 Kai La Pl 22a 18 of 50 Listing Image for 66 Kai La Pl 22a 19 of 50 Listing Image for 66 Kai La Pl 22a 20 of 50 Listing Image for 66 Kai La Pl 22a 21 of 50 Listing Image for 66 Kai La Pl 22a 22 of 50 Listing Image for 66 Kai La Pl 22a 23 of 50 Listing Image for 66 Kai La Pl 22a 24 of 50 Listing Image for 66 Kai La Pl 22a 25 of 50 Listing Image for 66 Kai La Pl 22a 26 of 50 Listing Image for 66 Kai La Pl 22a 27 of 50 Listing Image for 66 Kai La Pl 22a 28 of 50 Listing Image for 66 Kai La Pl 22a 29 of 50 Listing Image for 66 Kai La Pl 22a 30 of 50 Listing Image for 66 Kai La Pl 22a 31 of 50 Listing Image for 66 Kai La Pl 22a 32 of 50 Listing Image for 66 Kai La Pl 22a 33 of 50 Listing Image for 66 Kai La Pl 22a 34 of 50 Listing Image for 66 Kai La Pl 22a 35 of 50 Listing Image for 66 Kai La Pl 22a 36 of 50 Listing Image for 66 Kai La Pl 22a 37 of 50 Listing Image for 66 Kai La Pl 22a 38 of 50 Listing Image for 66 Kai La Pl 22a 39 of 50 Listing Image for 66 Kai La Pl 22a 40 of 50 Listing Image for 66 Kai La Pl 22a 41 of 50 Listing Image for 66 Kai La Pl 22a 42 of 50 Listing Image for 66 Kai La Pl 22a 43 of 50 Listing Image for 66 Kai La Pl 22a 44 of 50 Listing Image for 66 Kai La Pl 22a 45 of 50 Listing Image for 66 Kai La Pl 22a 46 of 50 Listing Image for 66 Kai La Pl 22a 47 of 50 Listing Image for 66 Kai La Pl 22a 48 of 50 Listing Image for 66 Kai La Pl 22a 49 of 50 Listing Image for 66 Kai La Pl 22a 50 of 50

$2,350,000

Kai Malu 22A

66 Kai La Pl 22a, Wailea/Makena

3 Beds 2.5 Baths 1,796 SqFt Residential MLS® # 409708 Date Sold: September 8, 2026
Sold
Closed: 06/26/2026
Listing Image for 7 Hoolai St 1 of 43 Listing Image for 7 Hoolai St 2 of 43 Listing Image for 7 Hoolai St 3 of 43 Listing Image for 7 Hoolai St 4 of 43 Listing Image for 7 Hoolai St 5 of 43 Listing Image for 7 Hoolai St 6 of 43 Listing Image for 7 Hoolai St 7 of 43 Listing Image for 7 Hoolai St 8 of 43 Listing Image for 7 Hoolai St 9 of 43 Listing Image for 7 Hoolai St 10 of 43 Listing Image for 7 Hoolai St 11 of 43 Listing Image for 7 Hoolai St 12 of 43 Listing Image for 7 Hoolai St 13 of 43 Listing Image for 7 Hoolai St 14 of 43 Listing Image for 7 Hoolai St 15 of 43 Listing Image for 7 Hoolai St 16 of 43 Listing Image for 7 Hoolai St 17 of 43 Listing Image for 7 Hoolai St 18 of 43 Listing Image for 7 Hoolai St 19 of 43 Listing Image for 7 Hoolai St 20 of 43 Listing Image for 7 Hoolai St 21 of 43 Listing Image for 7 Hoolai St 22 of 43 Listing Image for 7 Hoolai St 23 of 43 Listing Image for 7 Hoolai St 24 of 43 Listing Image for 7 Hoolai St 25 of 43 Listing Image for 7 Hoolai St 26 of 43 Listing Image for 7 Hoolai St 27 of 43 Listing Image for 7 Hoolai St 28 of 43 Listing Image for 7 Hoolai St 29 of 43 Listing Image for 7 Hoolai St 30 of 43 Listing Image for 7 Hoolai St 31 of 43 Listing Image for 7 Hoolai St 32 of 43 Listing Image for 7 Hoolai St 33 of 43 Listing Image for 7 Hoolai St 34 of 43 Listing Image for 7 Hoolai St 35 of 43 Listing Image for 7 Hoolai St 36 of 43 Listing Image for 7 Hoolai St 37 of 43 Listing Image for 7 Hoolai St 38 of 43 Listing Image for 7 Hoolai St 39 of 43 Listing Image for 7 Hoolai St 40 of 43 Listing Image for 7 Hoolai St 41 of 43 Listing Image for 7 Hoolai St 42 of 43 Listing Image for 7 Hoolai St 43 of 43

$999,999

Makawao Ranch Acres

7 Hoolai St, Makawao/Olinda/Haliimaile

3 Beds 2 Baths 1,356 SqFt Residential MLS® # 409706 Date Sold: June 26, 2026
Sold
Closed: 05/22/2026
83 Hoolawa Rd Unit A, Haiku

$1,375,000

Haiku

83 Hoolawa Rd Unit A, Haiku

0 Beds 0 Baths 0 SqFt Land MLS® # 409704 Date Sold: May 22, 2026
Sold
Closed: 08/03/2026
Listing Image for 137 Niihau St 1 of 11 Listing Image for 137 Niihau St 2 of 11 Listing Image for 137 Niihau St 3 of 11 Listing Image for 137 Niihau St 4 of 11 Listing Image for 137 Niihau St 5 of 11 Listing Image for 137 Niihau St 6 of 11 Listing Image for 137 Niihau St 7 of 11 Listing Image for 137 Niihau St 8 of 11 Listing Image for 137 Niihau St 9 of 11 Listing Image for 137 Niihau St 10 of 11 Listing Image for 137 Niihau St 11 of 11

$1,160,000

Kahului

137 Niihau St, Kahului

3 Beds 2 Baths 1,785 SqFt Residential MLS® # 409701 Date Sold: August 3, 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: 07/14/2026
Listing Image for 256 Lau Oliwa Loop 58 1 of 45 Listing Image for 256 Lau Oliwa Loop 58 2 of 45 Listing Image for 256 Lau Oliwa Loop 58 3 of 45 Listing Image for 256 Lau Oliwa Loop 58 4 of 45 Listing Image for 256 Lau Oliwa Loop 58 5 of 45 Listing Image for 256 Lau Oliwa Loop 58 6 of 45 Listing Image for 256 Lau Oliwa Loop 58 7 of 45 Listing Image for 256 Lau Oliwa Loop 58 8 of 45 Listing Image for 256 Lau Oliwa Loop 58 9 of 45 Listing Image for 256 Lau Oliwa Loop 58 10 of 45 Listing Image for 256 Lau Oliwa Loop 58 11 of 45 Listing Image for 256 Lau Oliwa Loop 58 12 of 45 Listing Image for 256 Lau Oliwa Loop 58 13 of 45 Listing Image for 256 Lau Oliwa Loop 58 14 of 45 Listing Image for 256 Lau Oliwa Loop 58 15 of 45 Listing Image for 256 Lau Oliwa Loop 58 16 of 45 Listing Image for 256 Lau Oliwa Loop 58 17 of 45 Listing Image for 256 Lau Oliwa Loop 58 18 of 45 Listing Image for 256 Lau Oliwa Loop 58 19 of 45 Listing Image for 256 Lau Oliwa Loop 58 20 of 45 Listing Image for 256 Lau Oliwa Loop 58 21 of 45 Listing Image for 256 Lau Oliwa Loop 58 22 of 45 Listing Image for 256 Lau Oliwa Loop 58 23 of 45 Listing Image for 256 Lau Oliwa Loop 58 24 of 45 Listing Image for 256 Lau Oliwa Loop 58 25 of 45 Listing Image for 256 Lau Oliwa Loop 58 26 of 45 Listing Image for 256 Lau Oliwa Loop 58 27 of 45 Listing Image for 256 Lau Oliwa Loop 58 28 of 45 Listing Image for 256 Lau Oliwa Loop 58 29 of 45 Listing Image for 256 Lau Oliwa Loop 58 30 of 45 Listing Image for 256 Lau Oliwa Loop 58 31 of 45 Listing Image for 256 Lau Oliwa Loop 58 32 of 45 Listing Image for 256 Lau Oliwa Loop 58 33 of 45 Listing Image for 256 Lau Oliwa Loop 58 34 of 45 Listing Image for 256 Lau Oliwa Loop 58 35 of 45 Listing Image for 256 Lau Oliwa Loop 58 36 of 45 Listing Image for 256 Lau Oliwa Loop 58 37 of 45 Listing Image for 256 Lau Oliwa Loop 58 38 of 45 Listing Image for 256 Lau Oliwa Loop 58 39 of 45 Listing Image for 256 Lau Oliwa Loop 58 40 of 45 Listing Image for 256 Lau Oliwa Loop 58 41 of 45 Listing Image for 256 Lau Oliwa Loop 58 42 of 45 Listing Image for 256 Lau Oliwa Loop 58 43 of 45 Listing Image for 256 Lau Oliwa Loop 58 44 of 45 Listing Image for 256 Lau Oliwa Loop 58 45 of 45

$949,000

Milo Court at Kehalani 58

256 Lau Oliwa Loop 58, Wailuku

3 Beds 2.5 Baths 1,457 SqFt Residential MLS® # 409700 Date Sold: July 14, 2026
Sold
Closed: 07/24/2026
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$6,950,000

Wailea Point 1103

4000 Wailea Alanui Dr 1103, Wailea/Makena

3 Beds 3 Baths 2,163 SqFt Residential MLS® # 409699 Date Sold: July 24, 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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