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:
In Escrow
Listing Image for 160 Kualapa Pl 60 1 of 49 Listing Image for 160 Kualapa Pl 60 2 of 49 Listing Image for 160 Kualapa Pl 60 3 of 49 Listing Image for 160 Kualapa Pl 60 4 of 49 Listing Image for 160 Kualapa Pl 60 5 of 49 Listing Image for 160 Kualapa Pl 60 6 of 49 Listing Image for 160 Kualapa Pl 60 7 of 49 Listing Image for 160 Kualapa Pl 60 8 of 49 Listing Image for 160 Kualapa Pl 60 9 of 49 Listing Image for 160 Kualapa Pl 60 10 of 49 Listing Image for 160 Kualapa Pl 60 11 of 49 Listing Image for 160 Kualapa Pl 60 12 of 49 Listing Image for 160 Kualapa Pl 60 13 of 49 Listing Image for 160 Kualapa Pl 60 14 of 49 Listing Image for 160 Kualapa Pl 60 15 of 49 Listing Image for 160 Kualapa Pl 60 16 of 49 Listing Image for 160 Kualapa Pl 60 17 of 49 Listing Image for 160 Kualapa Pl 60 18 of 49 Listing Image for 160 Kualapa Pl 60 19 of 49 Listing Image for 160 Kualapa Pl 60 20 of 49 Listing Image for 160 Kualapa Pl 60 21 of 49 Listing Image for 160 Kualapa Pl 60 22 of 49 Listing Image for 160 Kualapa Pl 60 23 of 49 Listing Image for 160 Kualapa Pl 60 24 of 49 Listing Image for 160 Kualapa Pl 60 25 of 49 Listing Image for 160 Kualapa Pl 60 26 of 49 Listing Image for 160 Kualapa Pl 60 27 of 49 Listing Image for 160 Kualapa Pl 60 28 of 49 Listing Image for 160 Kualapa Pl 60 29 of 49 Listing Image for 160 Kualapa Pl 60 30 of 49 Listing Image for 160 Kualapa Pl 60 31 of 49 Listing Image for 160 Kualapa Pl 60 32 of 49 Listing Image for 160 Kualapa Pl 60 33 of 49 Listing Image for 160 Kualapa Pl 60 34 of 49 Listing Image for 160 Kualapa Pl 60 35 of 49 Listing Image for 160 Kualapa Pl 60 36 of 49 Listing Image for 160 Kualapa Pl 60 37 of 49 Listing Image for 160 Kualapa Pl 60 38 of 49 Listing Image for 160 Kualapa Pl 60 39 of 49 Listing Image for 160 Kualapa Pl 60 40 of 49 Listing Image for 160 Kualapa Pl 60 41 of 49 Listing Image for 160 Kualapa Pl 60 42 of 49 Listing Image for 160 Kualapa Pl 60 43 of 49 Listing Image for 160 Kualapa Pl 60 44 of 49 Listing Image for 160 Kualapa Pl 60 45 of 49 Listing Image for 160 Kualapa Pl 60 46 of 49 Listing Image for 160 Kualapa Pl 60 47 of 49 Listing Image for 160 Kualapa Pl 60 48 of 49 Listing Image for 160 Kualapa Pl 60 49 of 49

$2,150,000

The Vintage at Kaanapali

160 Kualapa Pl 60, Kaanapali

3 Beds 2.5 Baths 2,200 SqFt Residential MLS® # 410510

Days on Market: 31

Island Sotheby's International Realty(L) Cell: 808-283-4922

Listing Image for 1887 Kaahele Pl 1 of 43 Listing Image for 1887 Kaahele Pl 2 of 43 Listing Image for 1887 Kaahele Pl 3 of 43 Listing Image for 1887 Kaahele Pl 4 of 43 Listing Image for 1887 Kaahele Pl 5 of 43 Listing Image for 1887 Kaahele Pl 6 of 43 Listing Image for 1887 Kaahele Pl 7 of 43 Listing Image for 1887 Kaahele Pl 8 of 43 Listing Image for 1887 Kaahele Pl 9 of 43 Listing Image for 1887 Kaahele Pl 10 of 43 Listing Image for 1887 Kaahele Pl 11 of 43 Listing Image for 1887 Kaahele Pl 12 of 43 Listing Image for 1887 Kaahele Pl 13 of 43 Listing Image for 1887 Kaahele Pl 14 of 43 Listing Image for 1887 Kaahele Pl 15 of 43 Listing Image for 1887 Kaahele Pl 16 of 43 Listing Image for 1887 Kaahele Pl 17 of 43 Listing Image for 1887 Kaahele Pl 18 of 43 Listing Image for 1887 Kaahele Pl 19 of 43 Listing Image for 1887 Kaahele Pl 20 of 43 Listing Image for 1887 Kaahele Pl 21 of 43 Listing Image for 1887 Kaahele Pl 22 of 43 Listing Image for 1887 Kaahele Pl 23 of 43 Listing Image for 1887 Kaahele Pl 24 of 43 Listing Image for 1887 Kaahele Pl 25 of 43 Listing Image for 1887 Kaahele Pl 26 of 43 Listing Image for 1887 Kaahele Pl 27 of 43 Listing Image for 1887 Kaahele Pl 28 of 43 Listing Image for 1887 Kaahele Pl 29 of 43 Listing Image for 1887 Kaahele Pl 30 of 43 Listing Image for 1887 Kaahele Pl 31 of 43 Listing Image for 1887 Kaahele Pl 32 of 43 Listing Image for 1887 Kaahele Pl 33 of 43 Listing Image for 1887 Kaahele Pl 34 of 43 Listing Image for 1887 Kaahele Pl 35 of 43 Listing Image for 1887 Kaahele Pl 36 of 43 Listing Image for 1887 Kaahele Pl 37 of 43 Listing Image for 1887 Kaahele Pl 38 of 43 Listing Image for 1887 Kaahele Pl 39 of 43 Listing Image for 1887 Kaahele Pl 40 of 43 Listing Image for 1887 Kaahele Pl 41 of 43 Listing Image for 1887 Kaahele Pl 42 of 43 Listing Image for 1887 Kaahele Pl 43 of 43

$1,620,000

Kihei

1887 Kaahele Pl, Kihei

5 Beds 3 Baths 2,838 SqFt Residential MLS® # 410506

Days on Market: 32

Coldwell Banker Island Prop(S) Cell: 808-269-7415

Listing Image for 279 Ohaa St 1 of 49 Listing Image for 279 Ohaa St 2 of 49 Listing Image for 279 Ohaa St 3 of 49 Listing Image for 279 Ohaa St 4 of 49 Listing Image for 279 Ohaa St 5 of 49 Listing Image for 279 Ohaa St 6 of 49 Listing Image for 279 Ohaa St 7 of 49 Listing Image for 279 Ohaa St 8 of 49 Listing Image for 279 Ohaa St 9 of 49 Listing Image for 279 Ohaa St 10 of 49 Listing Image for 279 Ohaa St 11 of 49 Listing Image for 279 Ohaa St 12 of 49 Listing Image for 279 Ohaa St 13 of 49 Listing Image for 279 Ohaa St 14 of 49 Listing Image for 279 Ohaa St 15 of 49 Listing Image for 279 Ohaa St 16 of 49 Listing Image for 279 Ohaa St 17 of 49 Listing Image for 279 Ohaa St 18 of 49 Listing Image for 279 Ohaa St 19 of 49 Listing Image for 279 Ohaa St 20 of 49 Listing Image for 279 Ohaa St 21 of 49 Listing Image for 279 Ohaa St 22 of 49 Listing Image for 279 Ohaa St 23 of 49 Listing Image for 279 Ohaa St 24 of 49 Listing Image for 279 Ohaa St 25 of 49 Listing Image for 279 Ohaa St 26 of 49 Listing Image for 279 Ohaa St 27 of 49 Listing Image for 279 Ohaa St 28 of 49 Listing Image for 279 Ohaa St 29 of 49 Listing Image for 279 Ohaa St 30 of 49 Listing Image for 279 Ohaa St 31 of 49 Listing Image for 279 Ohaa St 32 of 49 Listing Image for 279 Ohaa St 33 of 49 Listing Image for 279 Ohaa St 34 of 49 Listing Image for 279 Ohaa St 35 of 49 Listing Image for 279 Ohaa St 36 of 49 Listing Image for 279 Ohaa St 37 of 49 Listing Image for 279 Ohaa St 38 of 49 Listing Image for 279 Ohaa St 39 of 49 Listing Image for 279 Ohaa St 40 of 49 Listing Image for 279 Ohaa St 41 of 49 Listing Image for 279 Ohaa St 42 of 49 Listing Image for 279 Ohaa St 43 of 49 Listing Image for 279 Ohaa St 44 of 49 Listing Image for 279 Ohaa St 45 of 49 Listing Image for 279 Ohaa St 46 of 49 Listing Image for 279 Ohaa St 47 of 49 Listing Image for 279 Ohaa St 48 of 49 Listing Image for 279 Ohaa St 49 of 49

$1,198,000

↓ $21,000

Kahului

279 Ohaa St, Kahului

3 Beds 2 Baths 1,440 SqFt Residential MLS® # 410504

Days on Market: 32

Compass-W

Listing Image for 4996 Lower Honoapiilani Rd 1 of 37 Listing Image for 4996 Lower Honoapiilani Rd 2 of 37 Listing Image for 4996 Lower Honoapiilani Rd 3 of 37 Listing Image for 4996 Lower Honoapiilani Rd 4 of 37 Listing Image for 4996 Lower Honoapiilani Rd 5 of 37 Listing Image for 4996 Lower Honoapiilani Rd 6 of 37 Listing Image for 4996 Lower Honoapiilani Rd 7 of 37 Listing Image for 4996 Lower Honoapiilani Rd 8 of 37 Listing Image for 4996 Lower Honoapiilani Rd 9 of 37 Listing Image for 4996 Lower Honoapiilani Rd 10 of 37 Listing Image for 4996 Lower Honoapiilani Rd 11 of 37 Listing Image for 4996 Lower Honoapiilani Rd 12 of 37 Listing Image for 4996 Lower Honoapiilani Rd 13 of 37 Listing Image for 4996 Lower Honoapiilani Rd 14 of 37 Listing Image for 4996 Lower Honoapiilani Rd 15 of 37 Listing Image for 4996 Lower Honoapiilani Rd 16 of 37 Listing Image for 4996 Lower Honoapiilani Rd 17 of 37 Listing Image for 4996 Lower Honoapiilani Rd 18 of 37 Listing Image for 4996 Lower Honoapiilani Rd 19 of 37 Listing Image for 4996 Lower Honoapiilani Rd 20 of 37 Listing Image for 4996 Lower Honoapiilani Rd 21 of 37 Listing Image for 4996 Lower Honoapiilani Rd 22 of 37 Listing Image for 4996 Lower Honoapiilani Rd 23 of 37 Listing Image for 4996 Lower Honoapiilani Rd 24 of 37 Listing Image for 4996 Lower Honoapiilani Rd 25 of 37 Listing Image for 4996 Lower Honoapiilani Rd 26 of 37 Listing Image for 4996 Lower Honoapiilani Rd 27 of 37 Listing Image for 4996 Lower Honoapiilani Rd 28 of 37 Listing Image for 4996 Lower Honoapiilani Rd 29 of 37 Listing Image for 4996 Lower Honoapiilani Rd 30 of 37 Listing Image for 4996 Lower Honoapiilani Rd 31 of 37 Listing Image for 4996 Lower Honoapiilani Rd 32 of 37 Listing Image for 4996 Lower Honoapiilani Rd 33 of 37 Listing Image for 4996 Lower Honoapiilani Rd 34 of 37 Listing Image for 4996 Lower Honoapiilani Rd 35 of 37 Listing Image for 4996 Lower Honoapiilani Rd 36 of 37 Listing Image for 4996 Lower Honoapiilani Rd 37 of 37

$1,742,500

Napili/Kahana/Honokowai

4996 Lower Honoapiilani Rd, Napili/Kahana/Honokowai

4 Beds 2 Baths 2,022 SqFt Residential MLS® # 410500

Days on Market: 32

Island Sotheby's International Realty(L) Cell: 808-799-6922

Short Term Rental
Listing Image for 130 Kai Malina Pkwy Sr732 1 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 2 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 3 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 4 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 5 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 6 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 7 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 8 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 9 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 10 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 11 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 12 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 13 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 14 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 15 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 16 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 17 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 18 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 19 of 20 Listing Image for 130 Kai Malina Pkwy Sr732 20 of 20

$1,199,000

Honua Kai - Hoku Lani SR732

130 Kai Malina Pkwy Sr732, Kaanapali

1 Bed 1 Bath 620 SqFt Residential MLS® # 410496

Days on Market: 33

Coldwell Banker Island Prop-KP Cell: 808-214-4492

Listing Image for 10898 Kula Hwy 1 of 50 Listing Image for 10898 Kula Hwy 2 of 50 Listing Image for 10898 Kula Hwy 3 of 50 Listing Image for 10898 Kula Hwy 4 of 50 Listing Image for 10898 Kula Hwy 5 of 50 Listing Image for 10898 Kula Hwy 6 of 50 Listing Image for 10898 Kula Hwy 7 of 50 Listing Image for 10898 Kula Hwy 8 of 50 Listing Image for 10898 Kula Hwy 9 of 50 Listing Image for 10898 Kula Hwy 10 of 50 Listing Image for 10898 Kula Hwy 11 of 50 Listing Image for 10898 Kula Hwy 12 of 50 Listing Image for 10898 Kula Hwy 13 of 50 Listing Image for 10898 Kula Hwy 14 of 50 Listing Image for 10898 Kula Hwy 15 of 50 Listing Image for 10898 Kula Hwy 16 of 50 Listing Image for 10898 Kula Hwy 17 of 50 Listing Image for 10898 Kula Hwy 18 of 50 Listing Image for 10898 Kula Hwy 19 of 50 Listing Image for 10898 Kula Hwy 20 of 50 Listing Image for 10898 Kula Hwy 21 of 50 Listing Image for 10898 Kula Hwy 22 of 50 Listing Image for 10898 Kula Hwy 23 of 50 Listing Image for 10898 Kula Hwy 24 of 50 Listing Image for 10898 Kula Hwy 25 of 50 Listing Image for 10898 Kula Hwy 26 of 50 Listing Image for 10898 Kula Hwy 27 of 50 Listing Image for 10898 Kula Hwy 28 of 50 Listing Image for 10898 Kula Hwy 29 of 50 Listing Image for 10898 Kula Hwy 30 of 50 Listing Image for 10898 Kula Hwy 31 of 50 Listing Image for 10898 Kula Hwy 32 of 50 Listing Image for 10898 Kula Hwy 33 of 50 Listing Image for 10898 Kula Hwy 34 of 50 Listing Image for 10898 Kula Hwy 35 of 50 Listing Image for 10898 Kula Hwy 36 of 50 Listing Image for 10898 Kula Hwy 37 of 50 Listing Image for 10898 Kula Hwy 38 of 50 Listing Image for 10898 Kula Hwy 39 of 50 Listing Image for 10898 Kula Hwy 40 of 50 Listing Image for 10898 Kula Hwy 41 of 50 Listing Image for 10898 Kula Hwy 42 of 50 Listing Image for 10898 Kula Hwy 43 of 50 Listing Image for 10898 Kula Hwy 44 of 50 Listing Image for 10898 Kula Hwy 45 of 50 Listing Image for 10898 Kula Hwy 46 of 50 Listing Image for 10898 Kula Hwy 47 of 50 Listing Image for 10898 Kula Hwy 48 of 50 Listing Image for 10898 Kula Hwy 49 of 50 Listing Image for 10898 Kula Hwy 50 of 50

$4,400,000

Kula/Ulupalakua/Kanaio

10898 Kula Hwy, Kula/Ulupalakua/Kanaio

4 Beds 2.5 Baths 2,816 SqFt Residential MLS® # 410494

Days on Market: 33

Compass-W

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: 08/14/2026
Listing Image for 245 N Honokala Rd A 1 of 36 Listing Image for 245 N Honokala Rd A 2 of 36 Listing Image for 245 N Honokala Rd A 3 of 36 Listing Image for 245 N Honokala Rd A 4 of 36 Listing Image for 245 N Honokala Rd A 5 of 36 Listing Image for 245 N Honokala Rd A 6 of 36 Listing Image for 245 N Honokala Rd A 7 of 36 Listing Image for 245 N Honokala Rd A 8 of 36 Listing Image for 245 N Honokala Rd A 9 of 36 Listing Image for 245 N Honokala Rd A 10 of 36 Listing Image for 245 N Honokala Rd A 11 of 36 Listing Image for 245 N Honokala Rd A 12 of 36 Listing Image for 245 N Honokala Rd A 13 of 36 Listing Image for 245 N Honokala Rd A 14 of 36 Listing Image for 245 N Honokala Rd A 15 of 36 Listing Image for 245 N Honokala Rd A 16 of 36 Listing Image for 245 N Honokala Rd A 17 of 36 Listing Image for 245 N Honokala Rd A 18 of 36 Listing Image for 245 N Honokala Rd A 19 of 36 Listing Image for 245 N Honokala Rd A 20 of 36 Listing Image for 245 N Honokala Rd A 21 of 36 Listing Image for 245 N Honokala Rd A 22 of 36 Listing Image for 245 N Honokala Rd A 23 of 36 Listing Image for 245 N Honokala Rd A 24 of 36 Listing Image for 245 N Honokala Rd A 25 of 36 Listing Image for 245 N Honokala Rd A 26 of 36 Listing Image for 245 N Honokala Rd A 27 of 36 Listing Image for 245 N Honokala Rd A 28 of 36 Listing Image for 245 N Honokala Rd A 29 of 36 Listing Image for 245 N Honokala Rd A 30 of 36 Listing Image for 245 N Honokala Rd A 31 of 36 Listing Image for 245 N Honokala Rd A 32 of 36 Listing Image for 245 N Honokala Rd A 33 of 36 Listing Image for 245 N Honokala Rd A 34 of 36 Listing Image for 245 N Honokala Rd A 35 of 36 Listing Image for 245 N Honokala Rd A 36 of 36

$1,900,000

↓ $499,000

Honokala

245 N Honokala Rd A, Haiku

5 Beds 6.5 Baths 2,362 SqFt Residential MLS® # 409569 Date Sold: August 14, 2026
Sold
Closed: 07/08/2026
Listing Image for 35 Pakau Pl 1 of 38 Listing Image for 35 Pakau Pl 2 of 38 Listing Image for 35 Pakau Pl 3 of 38 Listing Image for 35 Pakau Pl 4 of 38 Listing Image for 35 Pakau Pl 5 of 38 Listing Image for 35 Pakau Pl 6 of 38 Listing Image for 35 Pakau Pl 7 of 38 Listing Image for 35 Pakau Pl 8 of 38 Listing Image for 35 Pakau Pl 9 of 38 Listing Image for 35 Pakau Pl 10 of 38 Listing Image for 35 Pakau Pl 11 of 38 Listing Image for 35 Pakau Pl 12 of 38 Listing Image for 35 Pakau Pl 13 of 38 Listing Image for 35 Pakau Pl 14 of 38 Listing Image for 35 Pakau Pl 15 of 38 Listing Image for 35 Pakau Pl 16 of 38 Listing Image for 35 Pakau Pl 17 of 38 Listing Image for 35 Pakau Pl 18 of 38 Listing Image for 35 Pakau Pl 19 of 38 Listing Image for 35 Pakau Pl 20 of 38 Listing Image for 35 Pakau Pl 21 of 38 Listing Image for 35 Pakau Pl 22 of 38 Listing Image for 35 Pakau Pl 23 of 38 Listing Image for 35 Pakau Pl 24 of 38 Listing Image for 35 Pakau Pl 25 of 38 Listing Image for 35 Pakau Pl 26 of 38 Listing Image for 35 Pakau Pl 27 of 38 Listing Image for 35 Pakau Pl 28 of 38 Listing Image for 35 Pakau Pl 29 of 38 Listing Image for 35 Pakau Pl 30 of 38 Listing Image for 35 Pakau Pl 31 of 38 Listing Image for 35 Pakau Pl 32 of 38 Listing Image for 35 Pakau Pl 33 of 38 Listing Image for 35 Pakau Pl 34 of 38 Listing Image for 35 Pakau Pl 35 of 38 Listing Image for 35 Pakau Pl 36 of 38 Listing Image for 35 Pakau Pl 37 of 38 Listing Image for 35 Pakau Pl 38 of 38

$1,219,000

↓ $80,000

The Parkways at Maui Lani

35 Pakau Pl, Kahului

3 Beds 2.5 Baths 1,992 SqFt Residential MLS® # 409280 Date Sold: July 8, 2026
Sold
Closed: 09/02/2026
Listing Image for 1648 Ainakea Rd 1 of 49 Listing Image for 1648 Ainakea Rd 2 of 49 Listing Image for 1648 Ainakea Rd 3 of 49 Listing Image for 1648 Ainakea Rd 4 of 49 Listing Image for 1648 Ainakea Rd 5 of 49 Listing Image for 1648 Ainakea Rd 6 of 49 Listing Image for 1648 Ainakea Rd 7 of 49 Listing Image for 1648 Ainakea Rd 8 of 49 Listing Image for 1648 Ainakea Rd 9 of 49 Listing Image for 1648 Ainakea Rd 10 of 49 Listing Image for 1648 Ainakea Rd 11 of 49 Listing Image for 1648 Ainakea Rd 12 of 49 Listing Image for 1648 Ainakea Rd 13 of 49 Listing Image for 1648 Ainakea Rd 14 of 49 Listing Image for 1648 Ainakea Rd 15 of 49 Listing Image for 1648 Ainakea Rd 16 of 49 Listing Image for 1648 Ainakea Rd 17 of 49 Listing Image for 1648 Ainakea Rd 18 of 49 Listing Image for 1648 Ainakea Rd 19 of 49 Listing Image for 1648 Ainakea Rd 20 of 49 Listing Image for 1648 Ainakea Rd 21 of 49 Listing Image for 1648 Ainakea Rd 22 of 49 Listing Image for 1648 Ainakea Rd 23 of 49 Listing Image for 1648 Ainakea Rd 24 of 49 Listing Image for 1648 Ainakea Rd 25 of 49 Listing Image for 1648 Ainakea Rd 26 of 49 Listing Image for 1648 Ainakea Rd 27 of 49 Listing Image for 1648 Ainakea Rd 28 of 49 Listing Image for 1648 Ainakea Rd 29 of 49 Listing Image for 1648 Ainakea Rd 30 of 49 Listing Image for 1648 Ainakea Rd 31 of 49 Listing Image for 1648 Ainakea Rd 32 of 49 Listing Image for 1648 Ainakea Rd 33 of 49 Listing Image for 1648 Ainakea Rd 34 of 49 Listing Image for 1648 Ainakea Rd 35 of 49 Listing Image for 1648 Ainakea Rd 36 of 49 Listing Image for 1648 Ainakea Rd 37 of 49 Listing Image for 1648 Ainakea Rd 38 of 49 Listing Image for 1648 Ainakea Rd 39 of 49 Listing Image for 1648 Ainakea Rd 40 of 49 Listing Image for 1648 Ainakea Rd 41 of 49 Listing Image for 1648 Ainakea Rd 42 of 49 Listing Image for 1648 Ainakea Rd 43 of 49 Listing Image for 1648 Ainakea Rd 44 of 49 Listing Image for 1648 Ainakea Rd 45 of 49 Listing Image for 1648 Ainakea Rd 46 of 49 Listing Image for 1648 Ainakea Rd 47 of 49 Listing Image for 1648 Ainakea Rd 48 of 49 Listing Image for 1648 Ainakea Rd 49 of 49

$950,000

Wahikuli

1648 Ainakea Rd, Lahaina

3 Beds 2.5 Baths 2,000 SqFt Residential MLS® # 409537 Date Sold: September 2, 2026
Sold
Closed: 07/24/2026
Listing Image for 2387 S Kihei Rd A403 1 of 19 Listing Image for 2387 S Kihei Rd A403 2 of 19 Listing Image for 2387 S Kihei Rd A403 3 of 19 Listing Image for 2387 S Kihei Rd A403 4 of 19 Listing Image for 2387 S Kihei Rd A403 5 of 19 Listing Image for 2387 S Kihei Rd A403 6 of 19 Listing Image for 2387 S Kihei Rd A403 7 of 19 Listing Image for 2387 S Kihei Rd A403 8 of 19 Listing Image for 2387 S Kihei Rd A403 9 of 19 Listing Image for 2387 S Kihei Rd A403 10 of 19 Listing Image for 2387 S Kihei Rd A403 11 of 19 Listing Image for 2387 S Kihei Rd A403 12 of 19 Listing Image for 2387 S Kihei Rd A403 13 of 19 Listing Image for 2387 S Kihei Rd A403 14 of 19 Listing Image for 2387 S Kihei Rd A403 15 of 19 Listing Image for 2387 S Kihei Rd A403 16 of 19 Listing Image for 2387 S Kihei Rd A403 17 of 19 Listing Image for 2387 S Kihei Rd A403 18 of 19 Listing Image for 2387 S Kihei Rd A403 19 of 19

$795,000

Kihei Alii Kai A403

2387 S Kihei Rd A403, Kihei

2 Beds 1 Bath 850 SqFt Residential MLS® # 409526 Date Sold: July 24, 2026
Sold
Closed: 06/17/2026
Listing Image for 270 Pau Hana Rd B 1 of 50 Listing Image for 270 Pau Hana Rd B 2 of 50 Listing Image for 270 Pau Hana Rd B 3 of 50 Listing Image for 270 Pau Hana Rd B 4 of 50 Listing Image for 270 Pau Hana Rd B 5 of 50 Listing Image for 270 Pau Hana Rd B 6 of 50 Listing Image for 270 Pau Hana Rd B 7 of 50 Listing Image for 270 Pau Hana Rd B 8 of 50 Listing Image for 270 Pau Hana Rd B 9 of 50 Listing Image for 270 Pau Hana Rd B 10 of 50 Listing Image for 270 Pau Hana Rd B 11 of 50 Listing Image for 270 Pau Hana Rd B 12 of 50 Listing Image for 270 Pau Hana Rd B 13 of 50 Listing Image for 270 Pau Hana Rd B 14 of 50 Listing Image for 270 Pau Hana Rd B 15 of 50 Listing Image for 270 Pau Hana Rd B 16 of 50 Listing Image for 270 Pau Hana Rd B 17 of 50 Listing Image for 270 Pau Hana Rd B 18 of 50 Listing Image for 270 Pau Hana Rd B 19 of 50 Listing Image for 270 Pau Hana Rd B 20 of 50 Listing Image for 270 Pau Hana Rd B 21 of 50 Listing Image for 270 Pau Hana Rd B 22 of 50 Listing Image for 270 Pau Hana Rd B 23 of 50 Listing Image for 270 Pau Hana Rd B 24 of 50 Listing Image for 270 Pau Hana Rd B 25 of 50 Listing Image for 270 Pau Hana Rd B 26 of 50 Listing Image for 270 Pau Hana Rd B 27 of 50 Listing Image for 270 Pau Hana Rd B 28 of 50 Listing Image for 270 Pau Hana Rd B 29 of 50 Listing Image for 270 Pau Hana Rd B 30 of 50 Listing Image for 270 Pau Hana Rd B 31 of 50 Listing Image for 270 Pau Hana Rd B 32 of 50 Listing Image for 270 Pau Hana Rd B 33 of 50 Listing Image for 270 Pau Hana Rd B 34 of 50 Listing Image for 270 Pau Hana Rd B 35 of 50 Listing Image for 270 Pau Hana Rd B 36 of 50 Listing Image for 270 Pau Hana Rd B 37 of 50 Listing Image for 270 Pau Hana Rd B 38 of 50 Listing Image for 270 Pau Hana Rd B 39 of 50 Listing Image for 270 Pau Hana Rd B 40 of 50 Listing Image for 270 Pau Hana Rd B 41 of 50 Listing Image for 270 Pau Hana Rd B 42 of 50 Listing Image for 270 Pau Hana Rd B 43 of 50 Listing Image for 270 Pau Hana Rd B 44 of 50 Listing Image for 270 Pau Hana Rd B 45 of 50 Listing Image for 270 Pau Hana Rd B 46 of 50 Listing Image for 270 Pau Hana Rd B 47 of 50 Listing Image for 270 Pau Hana Rd B 48 of 50 Listing Image for 270 Pau Hana Rd B 49 of 50 Listing Image for 270 Pau Hana Rd B 50 of 50

$1,010,000

Pau Hana Estates

270 Pau Hana Rd B, Makawao/Olinda/Haliimaile

2 Beds 1 Bath 744 SqFt Residential MLS® # 409525 Date Sold: June 17, 2026
Sold
Closed: 06/03/2026
Listing Image for 205 Pua Niu Way Unit A 1 of 45 Listing Image for 205 Pua Niu Way Unit A 2 of 45 Listing Image for 205 Pua Niu Way Unit A 3 of 45 Listing Image for 205 Pua Niu Way Unit A 4 of 45 Listing Image for 205 Pua Niu Way Unit A 5 of 45 Listing Image for 205 Pua Niu Way Unit A 6 of 45 Listing Image for 205 Pua Niu Way Unit A 7 of 45 Listing Image for 205 Pua Niu Way Unit A 8 of 45 Listing Image for 205 Pua Niu Way Unit A 9 of 45 Listing Image for 205 Pua Niu Way Unit A 10 of 45 Listing Image for 205 Pua Niu Way Unit A 11 of 45 Listing Image for 205 Pua Niu Way Unit A 12 of 45 Listing Image for 205 Pua Niu Way Unit A 13 of 45 Listing Image for 205 Pua Niu Way Unit A 14 of 45 Listing Image for 205 Pua Niu Way Unit A 15 of 45 Listing Image for 205 Pua Niu Way Unit A 16 of 45 Listing Image for 205 Pua Niu Way Unit A 17 of 45 Listing Image for 205 Pua Niu Way Unit A 18 of 45 Listing Image for 205 Pua Niu Way Unit A 19 of 45 Listing Image for 205 Pua Niu Way Unit A 20 of 45 Listing Image for 205 Pua Niu Way Unit A 21 of 45 Listing Image for 205 Pua Niu Way Unit A 22 of 45 Listing Image for 205 Pua Niu Way Unit A 23 of 45 Listing Image for 205 Pua Niu Way Unit A 24 of 45 Listing Image for 205 Pua Niu Way Unit A 25 of 45 Listing Image for 205 Pua Niu Way Unit A 26 of 45 Listing Image for 205 Pua Niu Way Unit A 27 of 45 Listing Image for 205 Pua Niu Way Unit A 28 of 45 Listing Image for 205 Pua Niu Way Unit A 29 of 45 Listing Image for 205 Pua Niu Way Unit A 30 of 45 Listing Image for 205 Pua Niu Way Unit A 31 of 45 Listing Image for 205 Pua Niu Way Unit A 32 of 45 Listing Image for 205 Pua Niu Way Unit A 33 of 45 Listing Image for 205 Pua Niu Way Unit A 34 of 45 Listing Image for 205 Pua Niu Way Unit A 35 of 45 Listing Image for 205 Pua Niu Way Unit A 36 of 45 Listing Image for 205 Pua Niu Way Unit A 37 of 45 Listing Image for 205 Pua Niu Way Unit A 38 of 45 Listing Image for 205 Pua Niu Way Unit A 39 of 45 Listing Image for 205 Pua Niu Way Unit A 40 of 45 Listing Image for 205 Pua Niu Way Unit A 41 of 45 Listing Image for 205 Pua Niu Way Unit A 42 of 45 Listing Image for 205 Pua Niu Way Unit A 43 of 45 Listing Image for 205 Pua Niu Way Unit A 44 of 45 Listing Image for 205 Pua Niu Way Unit A 45 of 45

$5,950,000

Mahanalua Nui IV

205 Pua Niu Way Unit A, Lahaina

5 Beds 4.5 Baths 3,697 SqFt Residential MLS® # 409523 Date Sold: June 3, 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.