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

$13,300,000

Spreckelsville/Paia/Kuau

33 Hana Hwy, Spreckelsville/Paia/Kuau

5 Beds 3 Baths 2,260 SqFt Residential MLS® # 410440

Days on Market: 40

The Agency Maui Cell: 808-344-5575

Short Term Rental
Listing Image for 2481 Kaanapali Pkwy 412 1 of 41 Listing Image for 2481 Kaanapali Pkwy 412 2 of 41 Listing Image for 2481 Kaanapali Pkwy 412 3 of 41 Listing Image for 2481 Kaanapali Pkwy 412 4 of 41 Listing Image for 2481 Kaanapali Pkwy 412 5 of 41 Listing Image for 2481 Kaanapali Pkwy 412 6 of 41 Listing Image for 2481 Kaanapali Pkwy 412 7 of 41 Listing Image for 2481 Kaanapali Pkwy 412 8 of 41 Listing Image for 2481 Kaanapali Pkwy 412 9 of 41 Listing Image for 2481 Kaanapali Pkwy 412 10 of 41 Listing Image for 2481 Kaanapali Pkwy 412 11 of 41 Listing Image for 2481 Kaanapali Pkwy 412 12 of 41 Listing Image for 2481 Kaanapali Pkwy 412 13 of 41 Listing Image for 2481 Kaanapali Pkwy 412 14 of 41 Listing Image for 2481 Kaanapali Pkwy 412 15 of 41 Listing Image for 2481 Kaanapali Pkwy 412 16 of 41 Listing Image for 2481 Kaanapali Pkwy 412 17 of 41 Listing Image for 2481 Kaanapali Pkwy 412 18 of 41 Listing Image for 2481 Kaanapali Pkwy 412 19 of 41 Listing Image for 2481 Kaanapali Pkwy 412 20 of 41 Listing Image for 2481 Kaanapali Pkwy 412 21 of 41 Listing Image for 2481 Kaanapali Pkwy 412 22 of 41 Listing Image for 2481 Kaanapali Pkwy 412 23 of 41 Listing Image for 2481 Kaanapali Pkwy 412 24 of 41 Listing Image for 2481 Kaanapali Pkwy 412 25 of 41 Listing Image for 2481 Kaanapali Pkwy 412 26 of 41 Listing Image for 2481 Kaanapali Pkwy 412 27 of 41 Listing Image for 2481 Kaanapali Pkwy 412 28 of 41 Listing Image for 2481 Kaanapali Pkwy 412 29 of 41 Listing Image for 2481 Kaanapali Pkwy 412 30 of 41 Listing Image for 2481 Kaanapali Pkwy 412 31 of 41 Listing Image for 2481 Kaanapali Pkwy 412 32 of 41 Listing Image for 2481 Kaanapali Pkwy 412 33 of 41 Listing Image for 2481 Kaanapali Pkwy 412 34 of 41 Listing Image for 2481 Kaanapali Pkwy 412 35 of 41 Listing Image for 2481 Kaanapali Pkwy 412 36 of 41 Listing Image for 2481 Kaanapali Pkwy 412 37 of 41 Listing Image for 2481 Kaanapali Pkwy 412 38 of 41 Listing Image for 2481 Kaanapali Pkwy 412 39 of 41 Listing Image for 2481 Kaanapali Pkwy 412 40 of 41 Listing Image for 2481 Kaanapali Pkwy 412 41 of 41

$1,495,000

↓ $75,000

Whaler 412

2481 Kaanapali Pkwy 412, Kaanapali

1 Bed 2 Baths 905 SqFt Residential MLS® # 410435

Days on Market: 40

Island Sotheby's International Realty(L) Cell: 808-250-0210

Listing Image for 185 Hololani St 1 of 48 Listing Image for 185 Hololani St 2 of 48 Listing Image for 185 Hololani St 3 of 48 Listing Image for 185 Hololani St 4 of 48 Listing Image for 185 Hololani St 5 of 48 Listing Image for 185 Hololani St 6 of 48 Listing Image for 185 Hololani St 7 of 48 Listing Image for 185 Hololani St 8 of 48 Listing Image for 185 Hololani St 9 of 48 Listing Image for 185 Hololani St 10 of 48 Listing Image for 185 Hololani St 11 of 48 Listing Image for 185 Hololani St 12 of 48 Listing Image for 185 Hololani St 13 of 48 Listing Image for 185 Hololani St 14 of 48 Listing Image for 185 Hololani St 15 of 48 Listing Image for 185 Hololani St 16 of 48 Listing Image for 185 Hololani St 17 of 48 Listing Image for 185 Hololani St 18 of 48 Listing Image for 185 Hololani St 19 of 48 Listing Image for 185 Hololani St 20 of 48 Listing Image for 185 Hololani St 21 of 48 Listing Image for 185 Hololani St 22 of 48 Listing Image for 185 Hololani St 23 of 48 Listing Image for 185 Hololani St 24 of 48 Listing Image for 185 Hololani St 25 of 48 Listing Image for 185 Hololani St 26 of 48 Listing Image for 185 Hololani St 27 of 48 Listing Image for 185 Hololani St 28 of 48 Listing Image for 185 Hololani St 29 of 48 Listing Image for 185 Hololani St 30 of 48 Listing Image for 185 Hololani St 31 of 48 Listing Image for 185 Hololani St 32 of 48 Listing Image for 185 Hololani St 33 of 48 Listing Image for 185 Hololani St 34 of 48 Listing Image for 185 Hololani St 35 of 48 Listing Image for 185 Hololani St 36 of 48 Listing Image for 185 Hololani St 37 of 48 Listing Image for 185 Hololani St 38 of 48 Listing Image for 185 Hololani St 39 of 48 Listing Image for 185 Hololani St 40 of 48 Listing Image for 185 Hololani St 41 of 48 Listing Image for 185 Hololani St 42 of 48 Listing Image for 185 Hololani St 43 of 48 Listing Image for 185 Hololani St 44 of 48 Listing Image for 185 Hololani St 45 of 48 Listing Image for 185 Hololani St 46 of 48 Listing Image for 185 Hololani St 47 of 48 Listing Image for 185 Hololani St 48 of 48

$1,239,000

Makawao/Olinda/Haliimaile

185 Hololani St, Makawao/Olinda/Haliimaile

3 Beds 2.5 Baths 1,592 SqFt Residential MLS® # 410434

Days on Market: 40

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

Short Term Rental
Listing Image for 2575 S Kihei Rd G101 1 of 21 Listing Image for 2575 S Kihei Rd G101 2 of 21 Listing Image for 2575 S Kihei Rd G101 3 of 21 Listing Image for 2575 S Kihei Rd G101 4 of 21 Listing Image for 2575 S Kihei Rd G101 5 of 21 Listing Image for 2575 S Kihei Rd G101 6 of 21 Listing Image for 2575 S Kihei Rd G101 7 of 21 Listing Image for 2575 S Kihei Rd G101 8 of 21 Listing Image for 2575 S Kihei Rd G101 9 of 21 Listing Image for 2575 S Kihei Rd G101 10 of 21 Listing Image for 2575 S Kihei Rd G101 11 of 21 Listing Image for 2575 S Kihei Rd G101 12 of 21 Listing Image for 2575 S Kihei Rd G101 13 of 21 Listing Image for 2575 S Kihei Rd G101 14 of 21 Listing Image for 2575 S Kihei Rd G101 15 of 21 Listing Image for 2575 S Kihei Rd G101 16 of 21 Listing Image for 2575 S Kihei Rd G101 17 of 21 Listing Image for 2575 S Kihei Rd G101 18 of 21 Listing Image for 2575 S Kihei Rd G101 19 of 21 Listing Image for 2575 S Kihei Rd G101 20 of 21 Listing Image for 2575 S Kihei Rd G101 21 of 21

$925,000

Maui Banyan G101

2575 S Kihei Rd G101, Kihei

2 Beds 2 Baths 890 SqFt Residential MLS® # 410432

Days on Market: 41

Hawaii Real Estate Executives Inc Cell: 808-298-1973

Short Term Rental
Listing Image for 3543 Lower Honoapiilani Rd A-403 1 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 2 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 3 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 4 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 5 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 6 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 7 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 8 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 9 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 10 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 11 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 12 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 13 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 14 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 15 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 16 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 17 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 18 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 19 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 20 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 21 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 22 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 23 of 24 Listing Image for 3543 Lower Honoapiilani Rd A-403 24 of 24

$1,595,000

Papakea Resort A-403

3543 Lower Honoapiilani Rd A-403, Napili/Kahana/Honokowai

2 Beds 2 Baths 1,145 SqFt Residential MLS® # 410431

Days on Market: 42

Hawaii Life (W) Cell: 808-870-0966

Listing Image for 54 Hakui Loop 1 of 48 Listing Image for 54 Hakui Loop 2 of 48 Listing Image for 54 Hakui Loop 3 of 48 Listing Image for 54 Hakui Loop 4 of 48 Listing Image for 54 Hakui Loop 5 of 48 Listing Image for 54 Hakui Loop 6 of 48 Listing Image for 54 Hakui Loop 7 of 48 Listing Image for 54 Hakui Loop 8 of 48 Listing Image for 54 Hakui Loop 9 of 48 Listing Image for 54 Hakui Loop 10 of 48 Listing Image for 54 Hakui Loop 11 of 48 Listing Image for 54 Hakui Loop 12 of 48 Listing Image for 54 Hakui Loop 13 of 48 Listing Image for 54 Hakui Loop 14 of 48 Listing Image for 54 Hakui Loop 15 of 48 Listing Image for 54 Hakui Loop 16 of 48 Listing Image for 54 Hakui Loop 17 of 48 Listing Image for 54 Hakui Loop 18 of 48 Listing Image for 54 Hakui Loop 19 of 48 Listing Image for 54 Hakui Loop 20 of 48 Listing Image for 54 Hakui Loop 21 of 48 Listing Image for 54 Hakui Loop 22 of 48 Listing Image for 54 Hakui Loop 23 of 48 Listing Image for 54 Hakui Loop 24 of 48 Listing Image for 54 Hakui Loop 25 of 48 Listing Image for 54 Hakui Loop 26 of 48 Listing Image for 54 Hakui Loop 27 of 48 Listing Image for 54 Hakui Loop 28 of 48 Listing Image for 54 Hakui Loop 29 of 48 Listing Image for 54 Hakui Loop 30 of 48 Listing Image for 54 Hakui Loop 31 of 48 Listing Image for 54 Hakui Loop 32 of 48 Listing Image for 54 Hakui Loop 33 of 48 Listing Image for 54 Hakui Loop 34 of 48 Listing Image for 54 Hakui Loop 35 of 48 Listing Image for 54 Hakui Loop 36 of 48 Listing Image for 54 Hakui Loop 37 of 48 Listing Image for 54 Hakui Loop 38 of 48 Listing Image for 54 Hakui Loop 39 of 48 Listing Image for 54 Hakui Loop 40 of 48 Listing Image for 54 Hakui Loop 41 of 48 Listing Image for 54 Hakui Loop 42 of 48 Listing Image for 54 Hakui Loop 43 of 48 Listing Image for 54 Hakui Loop 44 of 48 Listing Image for 54 Hakui Loop 45 of 48 Listing Image for 54 Hakui Loop 46 of 48 Listing Image for 54 Hakui Loop 47 of 48 Listing Image for 54 Hakui Loop 48 of 48

$3,399,000

Kaanapali Hillside

54 Hakui Loop, Kaanapali

6 Beds 6 Baths 6,089 SqFt Residential MLS® # 410430

Days on Market: 41

Coldwell Banker Island Prop-KP Cell: 808-868-8673

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: 05/22/2026
Listing Image for 36 S Kihei Rd 108 1 of 35 Listing Image for 36 S Kihei Rd 108 2 of 35 Listing Image for 36 S Kihei Rd 108 3 of 35 Listing Image for 36 S Kihei Rd 108 4 of 35 Listing Image for 36 S Kihei Rd 108 5 of 35 Listing Image for 36 S Kihei Rd 108 6 of 35 Listing Image for 36 S Kihei Rd 108 7 of 35 Listing Image for 36 S Kihei Rd 108 8 of 35 Listing Image for 36 S Kihei Rd 108 9 of 35 Listing Image for 36 S Kihei Rd 108 10 of 35 Listing Image for 36 S Kihei Rd 108 11 of 35 Listing Image for 36 S Kihei Rd 108 12 of 35 Listing Image for 36 S Kihei Rd 108 13 of 35 Listing Image for 36 S Kihei Rd 108 14 of 35 Listing Image for 36 S Kihei Rd 108 15 of 35 Listing Image for 36 S Kihei Rd 108 16 of 35 Listing Image for 36 S Kihei Rd 108 17 of 35 Listing Image for 36 S Kihei Rd 108 18 of 35 Listing Image for 36 S Kihei Rd 108 19 of 35 Listing Image for 36 S Kihei Rd 108 20 of 35 Listing Image for 36 S Kihei Rd 108 21 of 35 Listing Image for 36 S Kihei Rd 108 22 of 35 Listing Image for 36 S Kihei Rd 108 23 of 35 Listing Image for 36 S Kihei Rd 108 24 of 35 Listing Image for 36 S Kihei Rd 108 25 of 35 Listing Image for 36 S Kihei Rd 108 26 of 35 Listing Image for 36 S Kihei Rd 108 27 of 35 Listing Image for 36 S Kihei Rd 108 28 of 35 Listing Image for 36 S Kihei Rd 108 29 of 35 Listing Image for 36 S Kihei Rd 108 30 of 35 Listing Image for 36 S Kihei Rd 108 31 of 35 Listing Image for 36 S Kihei Rd 108 32 of 35 Listing Image for 36 S Kihei Rd 108 33 of 35 Listing Image for 36 S Kihei Rd 108 34 of 35 Listing Image for 36 S Kihei Rd 108 35 of 35

$880,000

Kihei Beach 108

36 S Kihei Rd 108, Kihei

1 Bed 1 Bath 732 SqFt Residential MLS® # 409347 Date Sold: May 22, 2026
Sold
Closed: 06/04/2026
Listing Image for 80 Koani Loop 1 of 17 Listing Image for 80 Koani Loop 2 of 17 Listing Image for 80 Koani Loop 3 of 17 Listing Image for 80 Koani Loop 4 of 17 Listing Image for 80 Koani Loop 5 of 17 Listing Image for 80 Koani Loop 6 of 17 Listing Image for 80 Koani Loop 7 of 17 Listing Image for 80 Koani Loop 8 of 17 Listing Image for 80 Koani Loop 9 of 17 Listing Image for 80 Koani Loop 10 of 17 Listing Image for 80 Koani Loop 11 of 17 Listing Image for 80 Koani Loop 12 of 17 Listing Image for 80 Koani Loop 13 of 17 Listing Image for 80 Koani Loop 14 of 17 Listing Image for 80 Koani Loop 15 of 17 Listing Image for 80 Koani Loop 16 of 17 Listing Image for 80 Koani Loop 17 of 17

$1,175,000

Waiolani Mauka

80 Koani Loop, Wailuku

3 Beds 2 Baths 1,947 SqFt Residential MLS® # 408914 Date Sold: June 4, 2026
Sold
Closed: 06/12/2026
Listing Image for 475 Front St 601 1 of 24 Listing Image for 475 Front St 601 2 of 24 Listing Image for 475 Front St 601 3 of 24 Listing Image for 475 Front St 601 4 of 24 Listing Image for 475 Front St 601 5 of 24 Listing Image for 475 Front St 601 6 of 24 Listing Image for 475 Front St 601 7 of 24 Listing Image for 475 Front St 601 8 of 24 Listing Image for 475 Front St 601 9 of 24 Listing Image for 475 Front St 601 10 of 24 Listing Image for 475 Front St 601 11 of 24 Listing Image for 475 Front St 601 12 of 24 Listing Image for 475 Front St 601 13 of 24 Listing Image for 475 Front St 601 14 of 24 Listing Image for 475 Front St 601 15 of 24 Listing Image for 475 Front St 601 16 of 24 Listing Image for 475 Front St 601 17 of 24 Listing Image for 475 Front St 601 18 of 24 Listing Image for 475 Front St 601 19 of 24 Listing Image for 475 Front St 601 20 of 24 Listing Image for 475 Front St 601 21 of 24 Listing Image for 475 Front St 601 22 of 24 Listing Image for 475 Front St 601 23 of 24 Listing Image for 475 Front St 601 24 of 24

$1,250,000

Lahaina Shores 601

475 Front St 601, Lahaina

1 Bed 1 Bath 923 SqFt Residential MLS® # 409344 Date Sold: June 12, 2026
Sold
Closed: 06/18/2026
Listing Image for 250 Halewili Dr 1 of 46 Listing Image for 250 Halewili Dr 2 of 46 Listing Image for 250 Halewili Dr 3 of 46 Listing Image for 250 Halewili Dr 4 of 46 Listing Image for 250 Halewili Dr 5 of 46 Listing Image for 250 Halewili Dr 6 of 46 Listing Image for 250 Halewili Dr 7 of 46 Listing Image for 250 Halewili Dr 8 of 46 Listing Image for 250 Halewili Dr 9 of 46 Listing Image for 250 Halewili Dr 10 of 46 Listing Image for 250 Halewili Dr 11 of 46 Listing Image for 250 Halewili Dr 12 of 46 Listing Image for 250 Halewili Dr 13 of 46 Listing Image for 250 Halewili Dr 14 of 46 Listing Image for 250 Halewili Dr 15 of 46 Listing Image for 250 Halewili Dr 16 of 46 Listing Image for 250 Halewili Dr 17 of 46 Listing Image for 250 Halewili Dr 18 of 46 Listing Image for 250 Halewili Dr 19 of 46 Listing Image for 250 Halewili Dr 20 of 46 Listing Image for 250 Halewili Dr 21 of 46 Listing Image for 250 Halewili Dr 22 of 46 Listing Image for 250 Halewili Dr 23 of 46 Listing Image for 250 Halewili Dr 24 of 46 Listing Image for 250 Halewili Dr 25 of 46 Listing Image for 250 Halewili Dr 26 of 46 Listing Image for 250 Halewili Dr 27 of 46 Listing Image for 250 Halewili Dr 28 of 46 Listing Image for 250 Halewili Dr 29 of 46 Listing Image for 250 Halewili Dr 30 of 46 Listing Image for 250 Halewili Dr 31 of 46 Listing Image for 250 Halewili Dr 32 of 46 Listing Image for 250 Halewili Dr 33 of 46 Listing Image for 250 Halewili Dr 34 of 46 Listing Image for 250 Halewili Dr 35 of 46 Listing Image for 250 Halewili Dr 36 of 46 Listing Image for 250 Halewili Dr 37 of 46 Listing Image for 250 Halewili Dr 38 of 46 Listing Image for 250 Halewili Dr 39 of 46 Listing Image for 250 Halewili Dr 40 of 46 Listing Image for 250 Halewili Dr 41 of 46 Listing Image for 250 Halewili Dr 42 of 46 Listing Image for 250 Halewili Dr 43 of 46 Listing Image for 250 Halewili Dr 44 of 46 Listing Image for 250 Halewili Dr 45 of 46 Listing Image for 250 Halewili Dr 46 of 46

$1,000,000

↓ $50,000

Mill Village

250 Halewili Dr, Wailuku

5 Beds 2.5 Baths 2,097 SqFt Residential MLS® # 409337 Date Sold: June 18, 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: 08/25/2026
Listing Image for 60 Anamuli St 1 of 46 Listing Image for 60 Anamuli St 2 of 46 Listing Image for 60 Anamuli St 3 of 46 Listing Image for 60 Anamuli St 4 of 46 Listing Image for 60 Anamuli St 5 of 46 Listing Image for 60 Anamuli St 6 of 46 Listing Image for 60 Anamuli St 7 of 46 Listing Image for 60 Anamuli St 8 of 46 Listing Image for 60 Anamuli St 9 of 46 Listing Image for 60 Anamuli St 10 of 46 Listing Image for 60 Anamuli St 11 of 46 Listing Image for 60 Anamuli St 12 of 46 Listing Image for 60 Anamuli St 13 of 46 Listing Image for 60 Anamuli St 14 of 46 Listing Image for 60 Anamuli St 15 of 46 Listing Image for 60 Anamuli St 16 of 46 Listing Image for 60 Anamuli St 17 of 46 Listing Image for 60 Anamuli St 18 of 46 Listing Image for 60 Anamuli St 19 of 46 Listing Image for 60 Anamuli St 20 of 46 Listing Image for 60 Anamuli St 21 of 46 Listing Image for 60 Anamuli St 22 of 46 Listing Image for 60 Anamuli St 23 of 46 Listing Image for 60 Anamuli St 24 of 46 Listing Image for 60 Anamuli St 25 of 46 Listing Image for 60 Anamuli St 26 of 46 Listing Image for 60 Anamuli St 27 of 46 Listing Image for 60 Anamuli St 28 of 46 Listing Image for 60 Anamuli St 29 of 46 Listing Image for 60 Anamuli St 30 of 46 Listing Image for 60 Anamuli St 31 of 46 Listing Image for 60 Anamuli St 32 of 46 Listing Image for 60 Anamuli St 33 of 46 Listing Image for 60 Anamuli St 34 of 46 Listing Image for 60 Anamuli St 35 of 46 Listing Image for 60 Anamuli St 36 of 46 Listing Image for 60 Anamuli St 37 of 46 Listing Image for 60 Anamuli St 38 of 46 Listing Image for 60 Anamuli St 39 of 46 Listing Image for 60 Anamuli St 40 of 46 Listing Image for 60 Anamuli St 41 of 46 Listing Image for 60 Anamuli St 42 of 46 Listing Image for 60 Anamuli St 43 of 46 Listing Image for 60 Anamuli St 44 of 46 Listing Image for 60 Anamuli St 45 of 46 Listing Image for 60 Anamuli St 46 of 46

$1,125,000

↑ $25,000

Maui Lani

60 Anamuli St, Kahului

4 Beds 2.5 Baths 1,485 SqFt Residential MLS® # 409335 Date Sold: August 25, 2026
Sold
Closed: 07/24/2026
Listing Image for 2881 S Kihei Rd 8 1 of 48 Listing Image for 2881 S Kihei Rd 8 2 of 48 Listing Image for 2881 S Kihei Rd 8 3 of 48 Listing Image for 2881 S Kihei Rd 8 4 of 48 Listing Image for 2881 S Kihei Rd 8 5 of 48 Listing Image for 2881 S Kihei Rd 8 6 of 48 Listing Image for 2881 S Kihei Rd 8 7 of 48 Listing Image for 2881 S Kihei Rd 8 8 of 48 Listing Image for 2881 S Kihei Rd 8 9 of 48 Listing Image for 2881 S Kihei Rd 8 10 of 48 Listing Image for 2881 S Kihei Rd 8 11 of 48 Listing Image for 2881 S Kihei Rd 8 12 of 48 Listing Image for 2881 S Kihei Rd 8 13 of 48 Listing Image for 2881 S Kihei Rd 8 14 of 48 Listing Image for 2881 S Kihei Rd 8 15 of 48 Listing Image for 2881 S Kihei Rd 8 16 of 48 Listing Image for 2881 S Kihei Rd 8 17 of 48 Listing Image for 2881 S Kihei Rd 8 18 of 48 Listing Image for 2881 S Kihei Rd 8 19 of 48 Listing Image for 2881 S Kihei Rd 8 20 of 48 Listing Image for 2881 S Kihei Rd 8 21 of 48 Listing Image for 2881 S Kihei Rd 8 22 of 48 Listing Image for 2881 S Kihei Rd 8 23 of 48 Listing Image for 2881 S Kihei Rd 8 24 of 48 Listing Image for 2881 S Kihei Rd 8 25 of 48 Listing Image for 2881 S Kihei Rd 8 26 of 48 Listing Image for 2881 S Kihei Rd 8 27 of 48 Listing Image for 2881 S Kihei Rd 8 28 of 48 Listing Image for 2881 S Kihei Rd 8 29 of 48 Listing Image for 2881 S Kihei Rd 8 30 of 48 Listing Image for 2881 S Kihei Rd 8 31 of 48 Listing Image for 2881 S Kihei Rd 8 32 of 48 Listing Image for 2881 S Kihei Rd 8 33 of 48 Listing Image for 2881 S Kihei Rd 8 34 of 48 Listing Image for 2881 S Kihei Rd 8 35 of 48 Listing Image for 2881 S Kihei Rd 8 36 of 48 Listing Image for 2881 S Kihei Rd 8 37 of 48 Listing Image for 2881 S Kihei Rd 8 38 of 48 Listing Image for 2881 S Kihei Rd 8 39 of 48 Listing Image for 2881 S Kihei Rd 8 40 of 48 Listing Image for 2881 S Kihei Rd 8 41 of 48 Listing Image for 2881 S Kihei Rd 8 42 of 48 Listing Image for 2881 S Kihei Rd 8 43 of 48 Listing Image for 2881 S Kihei Rd 8 44 of 48 Listing Image for 2881 S Kihei Rd 8 45 of 48 Listing Image for 2881 S Kihei Rd 8 46 of 48 Listing Image for 2881 S Kihei Rd 8 47 of 48 Listing Image for 2881 S Kihei Rd 8 48 of 48

$895,000

Maui Hill 8

2881 S Kihei Rd 8, Kihei

3 Beds 3 Baths 1,395 SqFt Residential MLS® # 409329 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.

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.