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 191 Laau Loke Loop Lot 7 1 of 7 Listing Image for 191 Laau Loke Loop Lot 7 2 of 7 Listing Image for 191 Laau Loke Loop Lot 7 3 of 7 Listing Image for 191 Laau Loke Loop Lot 7 4 of 7 Listing Image for 191 Laau Loke Loop Lot 7 5 of 7 Listing Image for 191 Laau Loke Loop Lot 7 6 of 7 Listing Image for 191 Laau Loke Loop Lot 7 7 of 7

$1,512,000

Anuhea at Kehalani

191 Laau Loke Loop Lot 7, Wailuku

3 Beds 2 Baths 1,596 SqFt Residential MLS® # 410731

Days on Market: 8

Towne Island Homes, Ltd

Short Term Rental
Listing Image for 2481 Kaanapali Pkwy 1215 1 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 2 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 3 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 4 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 5 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 6 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 7 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 8 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 9 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 10 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 11 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 12 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 13 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 14 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 15 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 16 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 17 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 18 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 19 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 20 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 21 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 22 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 23 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 24 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 25 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 26 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 27 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 28 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 29 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 30 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 31 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 32 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 33 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 34 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 35 of 36 Listing Image for 2481 Kaanapali Pkwy 1215 36 of 36

$995,000

Whaler 1215

2481 Kaanapali Pkwy 1215, Kaanapali

0 Beds 1 Bath 523 SqFt Residential MLS® # 410730

Days on Market: 8

Keller Williams Realty Maui-L Cell: 808-870-2525

Listing Image for 190 Aliiolani St 1 of 50 Listing Image for 190 Aliiolani St 2 of 50 Listing Image for 190 Aliiolani St 3 of 50 Listing Image for 190 Aliiolani St 4 of 50 Listing Image for 190 Aliiolani St 5 of 50 Listing Image for 190 Aliiolani St 6 of 50 Listing Image for 190 Aliiolani St 7 of 50 Listing Image for 190 Aliiolani St 8 of 50 Listing Image for 190 Aliiolani St 9 of 50 Listing Image for 190 Aliiolani St 10 of 50 Listing Image for 190 Aliiolani St 11 of 50 Listing Image for 190 Aliiolani St 12 of 50 Listing Image for 190 Aliiolani St 13 of 50 Listing Image for 190 Aliiolani St 14 of 50 Listing Image for 190 Aliiolani St 15 of 50 Listing Image for 190 Aliiolani St 16 of 50 Listing Image for 190 Aliiolani St 17 of 50 Listing Image for 190 Aliiolani St 18 of 50 Listing Image for 190 Aliiolani St 19 of 50 Listing Image for 190 Aliiolani St 20 of 50 Listing Image for 190 Aliiolani St 21 of 50 Listing Image for 190 Aliiolani St 22 of 50 Listing Image for 190 Aliiolani St 23 of 50 Listing Image for 190 Aliiolani St 24 of 50 Listing Image for 190 Aliiolani St 25 of 50 Listing Image for 190 Aliiolani St 26 of 50 Listing Image for 190 Aliiolani St 27 of 50 Listing Image for 190 Aliiolani St 28 of 50 Listing Image for 190 Aliiolani St 29 of 50 Listing Image for 190 Aliiolani St 30 of 50 Listing Image for 190 Aliiolani St 31 of 50 Listing Image for 190 Aliiolani St 32 of 50 Listing Image for 190 Aliiolani St 33 of 50 Listing Image for 190 Aliiolani St 34 of 50 Listing Image for 190 Aliiolani St 35 of 50 Listing Image for 190 Aliiolani St 36 of 50 Listing Image for 190 Aliiolani St 37 of 50 Listing Image for 190 Aliiolani St 38 of 50 Listing Image for 190 Aliiolani St 39 of 50 Listing Image for 190 Aliiolani St 40 of 50 Listing Image for 190 Aliiolani St 41 of 50 Listing Image for 190 Aliiolani St 42 of 50 Listing Image for 190 Aliiolani St 43 of 50 Listing Image for 190 Aliiolani St 44 of 50 Listing Image for 190 Aliiolani St 45 of 50 Listing Image for 190 Aliiolani St 46 of 50 Listing Image for 190 Aliiolani St 47 of 50 Listing Image for 190 Aliiolani St 48 of 50 Listing Image for 190 Aliiolani St 49 of 50 Listing Image for 190 Aliiolani St 50 of 50

$1,659,000

Pukalani

190 Aliiolani St, Pukalani

3 Beds 2 Baths 1,504 SqFt Residential MLS® # 410729

Days on Market: 8

Compass-W

Short Term Rental
Listing Image for 2960 S Kihei Rd 304 1 of 41 Listing Image for 2960 S Kihei Rd 304 2 of 41 Listing Image for 2960 S Kihei Rd 304 3 of 41 Listing Image for 2960 S Kihei Rd 304 4 of 41 Listing Image for 2960 S Kihei Rd 304 5 of 41 Listing Image for 2960 S Kihei Rd 304 6 of 41 Listing Image for 2960 S Kihei Rd 304 7 of 41 Listing Image for 2960 S Kihei Rd 304 8 of 41 Listing Image for 2960 S Kihei Rd 304 9 of 41 Listing Image for 2960 S Kihei Rd 304 10 of 41 Listing Image for 2960 S Kihei Rd 304 11 of 41 Listing Image for 2960 S Kihei Rd 304 12 of 41 Listing Image for 2960 S Kihei Rd 304 13 of 41 Listing Image for 2960 S Kihei Rd 304 14 of 41 Listing Image for 2960 S Kihei Rd 304 15 of 41 Listing Image for 2960 S Kihei Rd 304 16 of 41 Listing Image for 2960 S Kihei Rd 304 17 of 41 Listing Image for 2960 S Kihei Rd 304 18 of 41 Listing Image for 2960 S Kihei Rd 304 19 of 41 Listing Image for 2960 S Kihei Rd 304 20 of 41 Listing Image for 2960 S Kihei Rd 304 21 of 41 Listing Image for 2960 S Kihei Rd 304 22 of 41 Listing Image for 2960 S Kihei Rd 304 23 of 41 Listing Image for 2960 S Kihei Rd 304 24 of 41 Listing Image for 2960 S Kihei Rd 304 25 of 41 Listing Image for 2960 S Kihei Rd 304 26 of 41 Listing Image for 2960 S Kihei Rd 304 27 of 41 Listing Image for 2960 S Kihei Rd 304 28 of 41 Listing Image for 2960 S Kihei Rd 304 29 of 41 Listing Image for 2960 S Kihei Rd 304 30 of 41 Listing Image for 2960 S Kihei Rd 304 31 of 41 Listing Image for 2960 S Kihei Rd 304 32 of 41 Listing Image for 2960 S Kihei Rd 304 33 of 41 Listing Image for 2960 S Kihei Rd 304 34 of 41 Listing Image for 2960 S Kihei Rd 304 35 of 41 Listing Image for 2960 S Kihei Rd 304 36 of 41 Listing Image for 2960 S Kihei Rd 304 37 of 41 Listing Image for 2960 S Kihei Rd 304 38 of 41 Listing Image for 2960 S Kihei Rd 304 39 of 41 Listing Image for 2960 S Kihei Rd 304 40 of 41 Listing Image for 2960 S Kihei Rd 304 41 of 41

$1,995,000

Mana Kai 304

2960 S Kihei Rd 304, Kihei

2 Beds 2 Baths 767 SqFt Residential MLS® # 410724

Days on Market: 9

Coldwell Banker Island Prop(S) Cell: 808-870-4899

Buying Real Estate on Maui

Buying Real Estate on Maui

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

Read the Guide
Listing Image for 296 Kenolio Rd 1 of 50 Listing Image for 296 Kenolio Rd 2 of 50 Listing Image for 296 Kenolio Rd 3 of 50 Listing Image for 296 Kenolio Rd 4 of 50 Listing Image for 296 Kenolio Rd 5 of 50 Listing Image for 296 Kenolio Rd 6 of 50 Listing Image for 296 Kenolio Rd 7 of 50 Listing Image for 296 Kenolio Rd 8 of 50 Listing Image for 296 Kenolio Rd 9 of 50 Listing Image for 296 Kenolio Rd 10 of 50 Listing Image for 296 Kenolio Rd 11 of 50 Listing Image for 296 Kenolio Rd 12 of 50 Listing Image for 296 Kenolio Rd 13 of 50 Listing Image for 296 Kenolio Rd 14 of 50 Listing Image for 296 Kenolio Rd 15 of 50 Listing Image for 296 Kenolio Rd 16 of 50 Listing Image for 296 Kenolio Rd 17 of 50 Listing Image for 296 Kenolio Rd 18 of 50 Listing Image for 296 Kenolio Rd 19 of 50 Listing Image for 296 Kenolio Rd 20 of 50 Listing Image for 296 Kenolio Rd 21 of 50 Listing Image for 296 Kenolio Rd 22 of 50 Listing Image for 296 Kenolio Rd 23 of 50 Listing Image for 296 Kenolio Rd 24 of 50 Listing Image for 296 Kenolio Rd 25 of 50 Listing Image for 296 Kenolio Rd 26 of 50 Listing Image for 296 Kenolio Rd 27 of 50 Listing Image for 296 Kenolio Rd 28 of 50 Listing Image for 296 Kenolio Rd 29 of 50 Listing Image for 296 Kenolio Rd 30 of 50 Listing Image for 296 Kenolio Rd 31 of 50 Listing Image for 296 Kenolio Rd 32 of 50 Listing Image for 296 Kenolio Rd 33 of 50 Listing Image for 296 Kenolio Rd 34 of 50 Listing Image for 296 Kenolio Rd 35 of 50 Listing Image for 296 Kenolio Rd 36 of 50 Listing Image for 296 Kenolio Rd 37 of 50 Listing Image for 296 Kenolio Rd 38 of 50 Listing Image for 296 Kenolio Rd 39 of 50 Listing Image for 296 Kenolio Rd 40 of 50 Listing Image for 296 Kenolio Rd 41 of 50 Listing Image for 296 Kenolio Rd 42 of 50 Listing Image for 296 Kenolio Rd 43 of 50 Listing Image for 296 Kenolio Rd 44 of 50 Listing Image for 296 Kenolio Rd 45 of 50 Listing Image for 296 Kenolio Rd 46 of 50 Listing Image for 296 Kenolio Rd 47 of 50 Listing Image for 296 Kenolio Rd 48 of 50 Listing Image for 296 Kenolio Rd 49 of 50 Listing Image for 296 Kenolio Rd 50 of 50

$1,199,000

Kihei

296 Kenolio Rd, Kihei

4 Beds 3 Baths 1,948 SqFt Residential MLS® # 410723

Days on Market: 9

Whalers Investment Group LLC

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

$1,725,000

Kulamanu

8 Paliuli Pl, Kula/Ulupalakua/Kanaio

4 Beds 3.5 Baths 2,038 SqFt Residential MLS® # 410722

Days on Market: 9

Kulamanu Realty 808-280-1943

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: 08/17/2026
223 Pua Niu Way Unit B, Lahaina

$1,000,000

Lahaina

223 Pua Niu Way Unit B, Lahaina

0 Beds 0 Baths 0 SqFt Land MLS® # 410272 Date Sold: August 17, 2026
Sold
Closed: 08/27/2026
Listing Image for 610 Polipoli Rd 1 of 48 Listing Image for 610 Polipoli Rd 2 of 48 Listing Image for 610 Polipoli Rd 3 of 48 Listing Image for 610 Polipoli Rd 4 of 48 Listing Image for 610 Polipoli Rd 5 of 48 Listing Image for 610 Polipoli Rd 6 of 48 Listing Image for 610 Polipoli Rd 7 of 48 Listing Image for 610 Polipoli Rd 8 of 48 Listing Image for 610 Polipoli Rd 9 of 48 Listing Image for 610 Polipoli Rd 10 of 48 Listing Image for 610 Polipoli Rd 11 of 48 Listing Image for 610 Polipoli Rd 12 of 48 Listing Image for 610 Polipoli Rd 13 of 48 Listing Image for 610 Polipoli Rd 14 of 48 Listing Image for 610 Polipoli Rd 15 of 48 Listing Image for 610 Polipoli Rd 16 of 48 Listing Image for 610 Polipoli Rd 17 of 48 Listing Image for 610 Polipoli Rd 18 of 48 Listing Image for 610 Polipoli Rd 19 of 48 Listing Image for 610 Polipoli Rd 20 of 48 Listing Image for 610 Polipoli Rd 21 of 48 Listing Image for 610 Polipoli Rd 22 of 48 Listing Image for 610 Polipoli Rd 23 of 48 Listing Image for 610 Polipoli Rd 24 of 48 Listing Image for 610 Polipoli Rd 25 of 48 Listing Image for 610 Polipoli Rd 26 of 48 Listing Image for 610 Polipoli Rd 27 of 48 Listing Image for 610 Polipoli Rd 28 of 48 Listing Image for 610 Polipoli Rd 29 of 48 Listing Image for 610 Polipoli Rd 30 of 48 Listing Image for 610 Polipoli Rd 31 of 48 Listing Image for 610 Polipoli Rd 32 of 48 Listing Image for 610 Polipoli Rd 33 of 48 Listing Image for 610 Polipoli Rd 34 of 48 Listing Image for 610 Polipoli Rd 35 of 48 Listing Image for 610 Polipoli Rd 36 of 48 Listing Image for 610 Polipoli Rd 37 of 48 Listing Image for 610 Polipoli Rd 38 of 48 Listing Image for 610 Polipoli Rd 39 of 48 Listing Image for 610 Polipoli Rd 40 of 48 Listing Image for 610 Polipoli Rd 41 of 48 Listing Image for 610 Polipoli Rd 42 of 48 Listing Image for 610 Polipoli Rd 43 of 48 Listing Image for 610 Polipoli Rd 44 of 48 Listing Image for 610 Polipoli Rd 45 of 48 Listing Image for 610 Polipoli Rd 46 of 48 Listing Image for 610 Polipoli Rd 47 of 48 Listing Image for 610 Polipoli Rd 48 of 48

$2,500,000

Kula/Ulupalakua/Kanaio

610 Polipoli Rd, Kula/Ulupalakua/Kanaio

3 Beds 3 Baths 1,950 SqFt Residential MLS® # 410268 Date Sold: August 27, 2026
Sold
Closed: 08/25/2026
Listing Image for 32 Kinohi Loa St 1 of 50 Listing Image for 32 Kinohi Loa St 2 of 50 Listing Image for 32 Kinohi Loa St 3 of 50 Listing Image for 32 Kinohi Loa St 4 of 50 Listing Image for 32 Kinohi Loa St 5 of 50 Listing Image for 32 Kinohi Loa St 6 of 50 Listing Image for 32 Kinohi Loa St 7 of 50 Listing Image for 32 Kinohi Loa St 8 of 50 Listing Image for 32 Kinohi Loa St 9 of 50 Listing Image for 32 Kinohi Loa St 10 of 50 Listing Image for 32 Kinohi Loa St 11 of 50 Listing Image for 32 Kinohi Loa St 12 of 50 Listing Image for 32 Kinohi Loa St 13 of 50 Listing Image for 32 Kinohi Loa St 14 of 50 Listing Image for 32 Kinohi Loa St 15 of 50 Listing Image for 32 Kinohi Loa St 16 of 50 Listing Image for 32 Kinohi Loa St 17 of 50 Listing Image for 32 Kinohi Loa St 18 of 50 Listing Image for 32 Kinohi Loa St 19 of 50 Listing Image for 32 Kinohi Loa St 20 of 50 Listing Image for 32 Kinohi Loa St 21 of 50 Listing Image for 32 Kinohi Loa St 22 of 50 Listing Image for 32 Kinohi Loa St 23 of 50 Listing Image for 32 Kinohi Loa St 24 of 50 Listing Image for 32 Kinohi Loa St 25 of 50 Listing Image for 32 Kinohi Loa St 26 of 50 Listing Image for 32 Kinohi Loa St 27 of 50 Listing Image for 32 Kinohi Loa St 28 of 50 Listing Image for 32 Kinohi Loa St 29 of 50 Listing Image for 32 Kinohi Loa St 30 of 50 Listing Image for 32 Kinohi Loa St 31 of 50 Listing Image for 32 Kinohi Loa St 32 of 50 Listing Image for 32 Kinohi Loa St 33 of 50 Listing Image for 32 Kinohi Loa St 34 of 50 Listing Image for 32 Kinohi Loa St 35 of 50 Listing Image for 32 Kinohi Loa St 36 of 50 Listing Image for 32 Kinohi Loa St 37 of 50 Listing Image for 32 Kinohi Loa St 38 of 50 Listing Image for 32 Kinohi Loa St 39 of 50 Listing Image for 32 Kinohi Loa St 40 of 50 Listing Image for 32 Kinohi Loa St 41 of 50 Listing Image for 32 Kinohi Loa St 42 of 50 Listing Image for 32 Kinohi Loa St 43 of 50 Listing Image for 32 Kinohi Loa St 44 of 50 Listing Image for 32 Kinohi Loa St 45 of 50 Listing Image for 32 Kinohi Loa St 46 of 50 Listing Image for 32 Kinohi Loa St 47 of 50 Listing Image for 32 Kinohi Loa St 48 of 50 Listing Image for 32 Kinohi Loa St 49 of 50 Listing Image for 32 Kinohi Loa St 50 of 50

$1,111,000

Kehalani

32 Kinohi Loa St, Wailuku

3 Beds 3 Baths 1,288 SqFt Residential MLS® # 410239 Date Sold: August 25, 2026
Sold
Closed: 07/10/2026
270 Ainakula Rd, Kula/Ulupalakua/Kanaio

$899,000

Kula/Ulupalakua/Kanaio

270 Ainakula Rd, Kula/Ulupalakua/Kanaio

2 Beds 1 Bath 1,000 SqFt Residential MLS® # 410219 Date Sold: July 10, 2026
Sold
Closed: 08/12/2026
Listing Image for 254 Alalani St 1 of 26 Listing Image for 254 Alalani St 2 of 26 Listing Image for 254 Alalani St 3 of 26 Listing Image for 254 Alalani St 4 of 26 Listing Image for 254 Alalani St 5 of 26 Listing Image for 254 Alalani St 6 of 26 Listing Image for 254 Alalani St 7 of 26 Listing Image for 254 Alalani St 8 of 26 Listing Image for 254 Alalani St 9 of 26 Listing Image for 254 Alalani St 10 of 26 Listing Image for 254 Alalani St 11 of 26 Listing Image for 254 Alalani St 12 of 26 Listing Image for 254 Alalani St 13 of 26 Listing Image for 254 Alalani St 14 of 26 Listing Image for 254 Alalani St 15 of 26 Listing Image for 254 Alalani St 16 of 26 Listing Image for 254 Alalani St 17 of 26 Listing Image for 254 Alalani St 18 of 26 Listing Image for 254 Alalani St 19 of 26 Listing Image for 254 Alalani St 20 of 26 Listing Image for 254 Alalani St 21 of 26 Listing Image for 254 Alalani St 22 of 26 Listing Image for 254 Alalani St 23 of 26 Listing Image for 254 Alalani St 24 of 26 Listing Image for 254 Alalani St 25 of 26 Listing Image for 254 Alalani St 26 of 26

$920,000

Pukalani

254 Alalani St, Pukalani

1 Bed 1 Bath 984 SqFt Residential MLS® # 410205 Date Sold: August 12, 2026
Sold
Closed: 08/26/2026
Listing Image for 363 Kai Malu Pl 56b 1 of 50 Listing Image for 363 Kai Malu Pl 56b 2 of 50 Listing Image for 363 Kai Malu Pl 56b 3 of 50 Listing Image for 363 Kai Malu Pl 56b 4 of 50 Listing Image for 363 Kai Malu Pl 56b 5 of 50 Listing Image for 363 Kai Malu Pl 56b 6 of 50 Listing Image for 363 Kai Malu Pl 56b 7 of 50 Listing Image for 363 Kai Malu Pl 56b 8 of 50 Listing Image for 363 Kai Malu Pl 56b 9 of 50 Listing Image for 363 Kai Malu Pl 56b 10 of 50 Listing Image for 363 Kai Malu Pl 56b 11 of 50 Listing Image for 363 Kai Malu Pl 56b 12 of 50 Listing Image for 363 Kai Malu Pl 56b 13 of 50 Listing Image for 363 Kai Malu Pl 56b 14 of 50 Listing Image for 363 Kai Malu Pl 56b 15 of 50 Listing Image for 363 Kai Malu Pl 56b 16 of 50 Listing Image for 363 Kai Malu Pl 56b 17 of 50 Listing Image for 363 Kai Malu Pl 56b 18 of 50 Listing Image for 363 Kai Malu Pl 56b 19 of 50 Listing Image for 363 Kai Malu Pl 56b 20 of 50 Listing Image for 363 Kai Malu Pl 56b 21 of 50 Listing Image for 363 Kai Malu Pl 56b 22 of 50 Listing Image for 363 Kai Malu Pl 56b 23 of 50 Listing Image for 363 Kai Malu Pl 56b 24 of 50 Listing Image for 363 Kai Malu Pl 56b 25 of 50 Listing Image for 363 Kai Malu Pl 56b 26 of 50 Listing Image for 363 Kai Malu Pl 56b 27 of 50 Listing Image for 363 Kai Malu Pl 56b 28 of 50 Listing Image for 363 Kai Malu Pl 56b 29 of 50 Listing Image for 363 Kai Malu Pl 56b 30 of 50 Listing Image for 363 Kai Malu Pl 56b 31 of 50 Listing Image for 363 Kai Malu Pl 56b 32 of 50 Listing Image for 363 Kai Malu Pl 56b 33 of 50 Listing Image for 363 Kai Malu Pl 56b 34 of 50 Listing Image for 363 Kai Malu Pl 56b 35 of 50 Listing Image for 363 Kai Malu Pl 56b 36 of 50 Listing Image for 363 Kai Malu Pl 56b 37 of 50 Listing Image for 363 Kai Malu Pl 56b 38 of 50 Listing Image for 363 Kai Malu Pl 56b 39 of 50 Listing Image for 363 Kai Malu Pl 56b 40 of 50 Listing Image for 363 Kai Malu Pl 56b 41 of 50 Listing Image for 363 Kai Malu Pl 56b 42 of 50 Listing Image for 363 Kai Malu Pl 56b 43 of 50 Listing Image for 363 Kai Malu Pl 56b 44 of 50 Listing Image for 363 Kai Malu Pl 56b 45 of 50 Listing Image for 363 Kai Malu Pl 56b 46 of 50 Listing Image for 363 Kai Malu Pl 56b 47 of 50 Listing Image for 363 Kai Malu Pl 56b 48 of 50 Listing Image for 363 Kai Malu Pl 56b 49 of 50 Listing Image for 363 Kai Malu Pl 56b 50 of 50

$2,075,000

↓ $675,000

Kai Malu 56B

363 Kai Malu Pl 56b, Wailea/Makena

3 Beds 2.5 Baths 1,796 SqFt Residential MLS® # 410198 Date Sold: August 26, 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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