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 3100 Wailea Alanui Dr 17 1 of 49 Listing Image for 3100 Wailea Alanui Dr 17 2 of 49 Listing Image for 3100 Wailea Alanui Dr 17 3 of 49 Listing Image for 3100 Wailea Alanui Dr 17 4 of 49 Listing Image for 3100 Wailea Alanui Dr 17 5 of 49 Listing Image for 3100 Wailea Alanui Dr 17 6 of 49 Listing Image for 3100 Wailea Alanui Dr 17 7 of 49 Listing Image for 3100 Wailea Alanui Dr 17 8 of 49 Listing Image for 3100 Wailea Alanui Dr 17 9 of 49 Listing Image for 3100 Wailea Alanui Dr 17 10 of 49 Listing Image for 3100 Wailea Alanui Dr 17 11 of 49 Listing Image for 3100 Wailea Alanui Dr 17 12 of 49 Listing Image for 3100 Wailea Alanui Dr 17 13 of 49 Listing Image for 3100 Wailea Alanui Dr 17 14 of 49 Listing Image for 3100 Wailea Alanui Dr 17 15 of 49 Listing Image for 3100 Wailea Alanui Dr 17 16 of 49 Listing Image for 3100 Wailea Alanui Dr 17 17 of 49 Listing Image for 3100 Wailea Alanui Dr 17 18 of 49 Listing Image for 3100 Wailea Alanui Dr 17 19 of 49 Listing Image for 3100 Wailea Alanui Dr 17 20 of 49 Listing Image for 3100 Wailea Alanui Dr 17 21 of 49 Listing Image for 3100 Wailea Alanui Dr 17 22 of 49 Listing Image for 3100 Wailea Alanui Dr 17 23 of 49 Listing Image for 3100 Wailea Alanui Dr 17 24 of 49 Listing Image for 3100 Wailea Alanui Dr 17 25 of 49 Listing Image for 3100 Wailea Alanui Dr 17 26 of 49 Listing Image for 3100 Wailea Alanui Dr 17 27 of 49 Listing Image for 3100 Wailea Alanui Dr 17 28 of 49 Listing Image for 3100 Wailea Alanui Dr 17 29 of 49 Listing Image for 3100 Wailea Alanui Dr 17 30 of 49 Listing Image for 3100 Wailea Alanui Dr 17 31 of 49 Listing Image for 3100 Wailea Alanui Dr 17 32 of 49 Listing Image for 3100 Wailea Alanui Dr 17 33 of 49 Listing Image for 3100 Wailea Alanui Dr 17 34 of 49 Listing Image for 3100 Wailea Alanui Dr 17 35 of 49 Listing Image for 3100 Wailea Alanui Dr 17 36 of 49 Listing Image for 3100 Wailea Alanui Dr 17 37 of 49 Listing Image for 3100 Wailea Alanui Dr 17 38 of 49 Listing Image for 3100 Wailea Alanui Dr 17 39 of 49 Listing Image for 3100 Wailea Alanui Dr 17 40 of 49 Listing Image for 3100 Wailea Alanui Dr 17 41 of 49 Listing Image for 3100 Wailea Alanui Dr 17 42 of 49 Listing Image for 3100 Wailea Alanui Dr 17 43 of 49 Listing Image for 3100 Wailea Alanui Dr 17 44 of 49 Listing Image for 3100 Wailea Alanui Dr 17 45 of 49 Listing Image for 3100 Wailea Alanui Dr 17 46 of 49 Listing Image for 3100 Wailea Alanui Dr 17 47 of 49 Listing Image for 3100 Wailea Alanui Dr 17 48 of 49 Listing Image for 3100 Wailea Alanui Dr 17 49 of 49

$4,795,000

Papali Wailea 17

3100 Wailea Alanui Dr 17, Wailea/Makena

3 Beds 3.5 Baths 2,386 SqFt Residential MLS® # 410334

Days on Market: 54

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

Listing Image for 850 Kekoa Pl 1 of 16 Listing Image for 850 Kekoa Pl 2 of 16 Listing Image for 850 Kekoa Pl 3 of 16 Listing Image for 850 Kekoa Pl 4 of 16 Listing Image for 850 Kekoa Pl 5 of 16 Listing Image for 850 Kekoa Pl 6 of 16 Listing Image for 850 Kekoa Pl 7 of 16 Listing Image for 850 Kekoa Pl 8 of 16 Listing Image for 850 Kekoa Pl 9 of 16 Listing Image for 850 Kekoa Pl 10 of 16 Listing Image for 850 Kekoa Pl 11 of 16 Listing Image for 850 Kekoa Pl 12 of 16 Listing Image for 850 Kekoa Pl 13 of 16 Listing Image for 850 Kekoa Pl 14 of 16 Listing Image for 850 Kekoa Pl 15 of 16 Listing Image for 850 Kekoa Pl 16 of 16

$990,000

Waiehu Heights

850 Kekoa Pl, Wailuku

3 Beds 2 Baths 2,075 SqFt Residential MLS® # 410332

Days on Market: 54

Ihu Properties LLC

Listing Image for 56 Lopaka Pl 1 of 50 Listing Image for 56 Lopaka Pl 2 of 50 Listing Image for 56 Lopaka Pl 3 of 50 Listing Image for 56 Lopaka Pl 4 of 50 Listing Image for 56 Lopaka Pl 5 of 50 Listing Image for 56 Lopaka Pl 6 of 50 Listing Image for 56 Lopaka Pl 7 of 50 Listing Image for 56 Lopaka Pl 8 of 50 Listing Image for 56 Lopaka Pl 9 of 50 Listing Image for 56 Lopaka Pl 10 of 50 Listing Image for 56 Lopaka Pl 11 of 50 Listing Image for 56 Lopaka Pl 12 of 50 Listing Image for 56 Lopaka Pl 13 of 50 Listing Image for 56 Lopaka Pl 14 of 50 Listing Image for 56 Lopaka Pl 15 of 50 Listing Image for 56 Lopaka Pl 16 of 50 Listing Image for 56 Lopaka Pl 17 of 50 Listing Image for 56 Lopaka Pl 18 of 50 Listing Image for 56 Lopaka Pl 19 of 50 Listing Image for 56 Lopaka Pl 20 of 50 Listing Image for 56 Lopaka Pl 21 of 50 Listing Image for 56 Lopaka Pl 22 of 50 Listing Image for 56 Lopaka Pl 23 of 50 Listing Image for 56 Lopaka Pl 24 of 50 Listing Image for 56 Lopaka Pl 25 of 50 Listing Image for 56 Lopaka Pl 26 of 50 Listing Image for 56 Lopaka Pl 27 of 50 Listing Image for 56 Lopaka Pl 28 of 50 Listing Image for 56 Lopaka Pl 29 of 50 Listing Image for 56 Lopaka Pl 30 of 50 Listing Image for 56 Lopaka Pl 31 of 50 Listing Image for 56 Lopaka Pl 32 of 50 Listing Image for 56 Lopaka Pl 33 of 50 Listing Image for 56 Lopaka Pl 34 of 50 Listing Image for 56 Lopaka Pl 35 of 50 Listing Image for 56 Lopaka Pl 36 of 50 Listing Image for 56 Lopaka Pl 37 of 50 Listing Image for 56 Lopaka Pl 38 of 50 Listing Image for 56 Lopaka Pl 39 of 50 Listing Image for 56 Lopaka Pl 40 of 50 Listing Image for 56 Lopaka Pl 41 of 50 Listing Image for 56 Lopaka Pl 42 of 50 Listing Image for 56 Lopaka Pl 43 of 50 Listing Image for 56 Lopaka Pl 44 of 50 Listing Image for 56 Lopaka Pl 45 of 50 Listing Image for 56 Lopaka Pl 46 of 50 Listing Image for 56 Lopaka Pl 47 of 50 Listing Image for 56 Lopaka Pl 48 of 50 Listing Image for 56 Lopaka Pl 49 of 50 Listing Image for 56 Lopaka Pl 50 of 50

$2,222,222

↓ $172,778

Kula Mala

56 Lopaka Pl, Kula/Ulupalakua/Kanaio

3 Beds 2 Baths 2,674 SqFt Residential MLS® # 410327

Days on Market: 54

Haleakala Realty, LLC

Listing Image for 450 Laulea Pl 1 of 48 Listing Image for 450 Laulea Pl 2 of 48 Listing Image for 450 Laulea Pl 3 of 48 Listing Image for 450 Laulea Pl 4 of 48 Listing Image for 450 Laulea Pl 5 of 48 Listing Image for 450 Laulea Pl 6 of 48 Listing Image for 450 Laulea Pl 7 of 48 Listing Image for 450 Laulea Pl 8 of 48 Listing Image for 450 Laulea Pl 9 of 48 Listing Image for 450 Laulea Pl 10 of 48 Listing Image for 450 Laulea Pl 11 of 48 Listing Image for 450 Laulea Pl 12 of 48 Listing Image for 450 Laulea Pl 13 of 48 Listing Image for 450 Laulea Pl 14 of 48 Listing Image for 450 Laulea Pl 15 of 48 Listing Image for 450 Laulea Pl 16 of 48 Listing Image for 450 Laulea Pl 17 of 48 Listing Image for 450 Laulea Pl 18 of 48 Listing Image for 450 Laulea Pl 19 of 48 Listing Image for 450 Laulea Pl 20 of 48 Listing Image for 450 Laulea Pl 21 of 48 Listing Image for 450 Laulea Pl 22 of 48 Listing Image for 450 Laulea Pl 23 of 48 Listing Image for 450 Laulea Pl 24 of 48 Listing Image for 450 Laulea Pl 25 of 48 Listing Image for 450 Laulea Pl 26 of 48 Listing Image for 450 Laulea Pl 27 of 48 Listing Image for 450 Laulea Pl 28 of 48 Listing Image for 450 Laulea Pl 29 of 48 Listing Image for 450 Laulea Pl 30 of 48 Listing Image for 450 Laulea Pl 31 of 48 Listing Image for 450 Laulea Pl 32 of 48 Listing Image for 450 Laulea Pl 33 of 48 Listing Image for 450 Laulea Pl 34 of 48 Listing Image for 450 Laulea Pl 35 of 48 Listing Image for 450 Laulea Pl 36 of 48 Listing Image for 450 Laulea Pl 37 of 48 Listing Image for 450 Laulea Pl 38 of 48 Listing Image for 450 Laulea Pl 39 of 48 Listing Image for 450 Laulea Pl 40 of 48 Listing Image for 450 Laulea Pl 41 of 48 Listing Image for 450 Laulea Pl 42 of 48 Listing Image for 450 Laulea Pl 43 of 48 Listing Image for 450 Laulea Pl 44 of 48 Listing Image for 450 Laulea Pl 45 of 48 Listing Image for 450 Laulea Pl 46 of 48 Listing Image for 450 Laulea Pl 47 of 48 Listing Image for 450 Laulea Pl 48 of 48

$4,500,000

Spreckelsville/Paia/Kuau

450 Laulea Pl, Spreckelsville/Paia/Kuau

2 Beds 2 Baths 1,286 SqFt Residential MLS® # 410325

Days on Market: 54

The Maui Real Estate Team Inc Cell: 808-283-6377

Listing Image for 420 Haumana Rd 1 of 33 Listing Image for 420 Haumana Rd 2 of 33 Listing Image for 420 Haumana Rd 3 of 33 Listing Image for 420 Haumana Rd 4 of 33 Listing Image for 420 Haumana Rd 5 of 33 Listing Image for 420 Haumana Rd 6 of 33 Listing Image for 420 Haumana Rd 7 of 33 Listing Image for 420 Haumana Rd 8 of 33 Listing Image for 420 Haumana Rd 9 of 33 Listing Image for 420 Haumana Rd 10 of 33 Listing Image for 420 Haumana Rd 11 of 33 Listing Image for 420 Haumana Rd 12 of 33 Listing Image for 420 Haumana Rd 13 of 33 Listing Image for 420 Haumana Rd 14 of 33 Listing Image for 420 Haumana Rd 15 of 33 Listing Image for 420 Haumana Rd 16 of 33 Listing Image for 420 Haumana Rd 17 of 33 Listing Image for 420 Haumana Rd 18 of 33 Listing Image for 420 Haumana Rd 19 of 33 Listing Image for 420 Haumana Rd 20 of 33 Listing Image for 420 Haumana Rd 21 of 33 Listing Image for 420 Haumana Rd 22 of 33 Listing Image for 420 Haumana Rd 23 of 33 Listing Image for 420 Haumana Rd 24 of 33 Listing Image for 420 Haumana Rd 25 of 33 Listing Image for 420 Haumana Rd 26 of 33 Listing Image for 420 Haumana Rd 27 of 33 Listing Image for 420 Haumana Rd 28 of 33 Listing Image for 420 Haumana Rd 29 of 33 Listing Image for 420 Haumana Rd 30 of 33 Listing Image for 420 Haumana Rd 31 of 33 Listing Image for 420 Haumana Rd 32 of 33 Listing Image for 420 Haumana Rd 33 of 33

$945,000

Haiku

420 Haumana Rd, Haiku

2 Beds 1 Bath 860 SqFt Residential MLS® # 410324

Days on Market: 54

Compass-W

Listing Image for 5412 Makena Alanui Rd 102/kv-3b 1 of 2 Listing Image for 5412 Makena Alanui Rd 102/kv-3b 2 of 2

$12,500,000

Makena Beach Club & Residences 102/KV-3B

5412 Makena Alanui Rd 102/kv-3b, Wailea/Makena

4 Beds 4.5 Baths 3,834 SqFt Residential MLS® # 407694

Days on Market: 308

Discovery Makena Realty LLC

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: 07/24/2026
Listing Image for 886 Mahealani St 1 of 50 Listing Image for 886 Mahealani St 2 of 50 Listing Image for 886 Mahealani St 3 of 50 Listing Image for 886 Mahealani St 4 of 50 Listing Image for 886 Mahealani St 5 of 50 Listing Image for 886 Mahealani St 6 of 50 Listing Image for 886 Mahealani St 7 of 50 Listing Image for 886 Mahealani St 8 of 50 Listing Image for 886 Mahealani St 9 of 50 Listing Image for 886 Mahealani St 10 of 50 Listing Image for 886 Mahealani St 11 of 50 Listing Image for 886 Mahealani St 12 of 50 Listing Image for 886 Mahealani St 13 of 50 Listing Image for 886 Mahealani St 14 of 50 Listing Image for 886 Mahealani St 15 of 50 Listing Image for 886 Mahealani St 16 of 50 Listing Image for 886 Mahealani St 17 of 50 Listing Image for 886 Mahealani St 18 of 50 Listing Image for 886 Mahealani St 19 of 50 Listing Image for 886 Mahealani St 20 of 50 Listing Image for 886 Mahealani St 21 of 50 Listing Image for 886 Mahealani St 22 of 50 Listing Image for 886 Mahealani St 23 of 50 Listing Image for 886 Mahealani St 24 of 50 Listing Image for 886 Mahealani St 25 of 50 Listing Image for 886 Mahealani St 26 of 50 Listing Image for 886 Mahealani St 27 of 50 Listing Image for 886 Mahealani St 28 of 50 Listing Image for 886 Mahealani St 29 of 50 Listing Image for 886 Mahealani St 30 of 50 Listing Image for 886 Mahealani St 31 of 50 Listing Image for 886 Mahealani St 32 of 50 Listing Image for 886 Mahealani St 33 of 50 Listing Image for 886 Mahealani St 34 of 50 Listing Image for 886 Mahealani St 35 of 50 Listing Image for 886 Mahealani St 36 of 50 Listing Image for 886 Mahealani St 37 of 50 Listing Image for 886 Mahealani St 38 of 50 Listing Image for 886 Mahealani St 39 of 50 Listing Image for 886 Mahealani St 40 of 50 Listing Image for 886 Mahealani St 41 of 50 Listing Image for 886 Mahealani St 42 of 50 Listing Image for 886 Mahealani St 43 of 50 Listing Image for 886 Mahealani St 44 of 50 Listing Image for 886 Mahealani St 45 of 50 Listing Image for 886 Mahealani St 46 of 50 Listing Image for 886 Mahealani St 47 of 50 Listing Image for 886 Mahealani St 48 of 50 Listing Image for 886 Mahealani St 49 of 50 Listing Image for 886 Mahealani St 50 of 50

$949,000

↓ $75,000

Piilani Village

886 Mahealani St, Kihei

3 Beds 2 Baths 1,336 SqFt Residential MLS® # 409112 Date Sold: July 24, 2026
Sold
Closed: 06/17/2026
Listing Image for 272 Hololani St 1 of 45 Listing Image for 272 Hololani St 2 of 45 Listing Image for 272 Hololani St 3 of 45 Listing Image for 272 Hololani St 4 of 45 Listing Image for 272 Hololani St 5 of 45 Listing Image for 272 Hololani St 6 of 45 Listing Image for 272 Hololani St 7 of 45 Listing Image for 272 Hololani St 8 of 45 Listing Image for 272 Hololani St 9 of 45 Listing Image for 272 Hololani St 10 of 45 Listing Image for 272 Hololani St 11 of 45 Listing Image for 272 Hololani St 12 of 45 Listing Image for 272 Hololani St 13 of 45 Listing Image for 272 Hololani St 14 of 45 Listing Image for 272 Hololani St 15 of 45 Listing Image for 272 Hololani St 16 of 45 Listing Image for 272 Hololani St 17 of 45 Listing Image for 272 Hololani St 18 of 45 Listing Image for 272 Hololani St 19 of 45 Listing Image for 272 Hololani St 20 of 45 Listing Image for 272 Hololani St 21 of 45 Listing Image for 272 Hololani St 22 of 45 Listing Image for 272 Hololani St 23 of 45 Listing Image for 272 Hololani St 24 of 45 Listing Image for 272 Hololani St 25 of 45 Listing Image for 272 Hololani St 26 of 45 Listing Image for 272 Hololani St 27 of 45 Listing Image for 272 Hololani St 28 of 45 Listing Image for 272 Hololani St 29 of 45 Listing Image for 272 Hololani St 30 of 45 Listing Image for 272 Hololani St 31 of 45 Listing Image for 272 Hololani St 32 of 45 Listing Image for 272 Hololani St 33 of 45 Listing Image for 272 Hololani St 34 of 45 Listing Image for 272 Hololani St 35 of 45 Listing Image for 272 Hololani St 36 of 45 Listing Image for 272 Hololani St 37 of 45 Listing Image for 272 Hololani St 38 of 45 Listing Image for 272 Hololani St 39 of 45 Listing Image for 272 Hololani St 40 of 45 Listing Image for 272 Hololani St 41 of 45 Listing Image for 272 Hololani St 42 of 45 Listing Image for 272 Hololani St 43 of 45 Listing Image for 272 Hololani St 44 of 45 Listing Image for 272 Hololani St 45 of 45

$1,350,000

Pukalani Golf Course

272 Hololani St, Pukalani

3 Beds 2 Baths 1,833 SqFt Residential MLS® # 409143 Date Sold: June 17, 2026
Sold
Closed: 07/31/2026
Listing Image for 17 Hua Nui Way 1 of 50 Listing Image for 17 Hua Nui Way 2 of 50 Listing Image for 17 Hua Nui Way 3 of 50 Listing Image for 17 Hua Nui Way 4 of 50 Listing Image for 17 Hua Nui Way 5 of 50 Listing Image for 17 Hua Nui Way 6 of 50 Listing Image for 17 Hua Nui Way 7 of 50 Listing Image for 17 Hua Nui Way 8 of 50 Listing Image for 17 Hua Nui Way 9 of 50 Listing Image for 17 Hua Nui Way 10 of 50 Listing Image for 17 Hua Nui Way 11 of 50 Listing Image for 17 Hua Nui Way 12 of 50 Listing Image for 17 Hua Nui Way 13 of 50 Listing Image for 17 Hua Nui Way 14 of 50 Listing Image for 17 Hua Nui Way 15 of 50 Listing Image for 17 Hua Nui Way 16 of 50 Listing Image for 17 Hua Nui Way 17 of 50 Listing Image for 17 Hua Nui Way 18 of 50 Listing Image for 17 Hua Nui Way 19 of 50 Listing Image for 17 Hua Nui Way 20 of 50 Listing Image for 17 Hua Nui Way 21 of 50 Listing Image for 17 Hua Nui Way 22 of 50 Listing Image for 17 Hua Nui Way 23 of 50 Listing Image for 17 Hua Nui Way 24 of 50 Listing Image for 17 Hua Nui Way 25 of 50 Listing Image for 17 Hua Nui Way 26 of 50 Listing Image for 17 Hua Nui Way 27 of 50 Listing Image for 17 Hua Nui Way 28 of 50 Listing Image for 17 Hua Nui Way 29 of 50 Listing Image for 17 Hua Nui Way 30 of 50 Listing Image for 17 Hua Nui Way 31 of 50 Listing Image for 17 Hua Nui Way 32 of 50 Listing Image for 17 Hua Nui Way 33 of 50 Listing Image for 17 Hua Nui Way 34 of 50 Listing Image for 17 Hua Nui Way 35 of 50 Listing Image for 17 Hua Nui Way 36 of 50 Listing Image for 17 Hua Nui Way 37 of 50 Listing Image for 17 Hua Nui Way 38 of 50 Listing Image for 17 Hua Nui Way 39 of 50 Listing Image for 17 Hua Nui Way 40 of 50 Listing Image for 17 Hua Nui Way 41 of 50 Listing Image for 17 Hua Nui Way 42 of 50 Listing Image for 17 Hua Nui Way 43 of 50 Listing Image for 17 Hua Nui Way 44 of 50 Listing Image for 17 Hua Nui Way 45 of 50 Listing Image for 17 Hua Nui Way 46 of 50 Listing Image for 17 Hua Nui Way 47 of 50 Listing Image for 17 Hua Nui Way 48 of 50 Listing Image for 17 Hua Nui Way 49 of 50 Listing Image for 17 Hua Nui Way 50 of 50

$1,399,000

↓ $51,000

Kahana Wai

17 Hua Nui Way, Napili/Kahana/Honokowai

3 Beds 2 Baths 1,774 SqFt Residential MLS® # 409138 Date Sold: July 31, 2026
Sold
Closed: 05/04/2026
Listing Image for 49 Wawali St 1 of 49 Listing Image for 49 Wawali St 2 of 49 Listing Image for 49 Wawali St 3 of 49 Listing Image for 49 Wawali St 4 of 49 Listing Image for 49 Wawali St 5 of 49 Listing Image for 49 Wawali St 6 of 49 Listing Image for 49 Wawali St 7 of 49 Listing Image for 49 Wawali St 8 of 49 Listing Image for 49 Wawali St 9 of 49 Listing Image for 49 Wawali St 10 of 49 Listing Image for 49 Wawali St 11 of 49 Listing Image for 49 Wawali St 12 of 49 Listing Image for 49 Wawali St 13 of 49 Listing Image for 49 Wawali St 14 of 49 Listing Image for 49 Wawali St 15 of 49 Listing Image for 49 Wawali St 16 of 49 Listing Image for 49 Wawali St 17 of 49 Listing Image for 49 Wawali St 18 of 49 Listing Image for 49 Wawali St 19 of 49 Listing Image for 49 Wawali St 20 of 49 Listing Image for 49 Wawali St 21 of 49 Listing Image for 49 Wawali St 22 of 49 Listing Image for 49 Wawali St 23 of 49 Listing Image for 49 Wawali St 24 of 49 Listing Image for 49 Wawali St 25 of 49 Listing Image for 49 Wawali St 26 of 49 Listing Image for 49 Wawali St 27 of 49 Listing Image for 49 Wawali St 28 of 49 Listing Image for 49 Wawali St 29 of 49 Listing Image for 49 Wawali St 30 of 49 Listing Image for 49 Wawali St 31 of 49 Listing Image for 49 Wawali St 32 of 49 Listing Image for 49 Wawali St 33 of 49 Listing Image for 49 Wawali St 34 of 49 Listing Image for 49 Wawali St 35 of 49 Listing Image for 49 Wawali St 36 of 49 Listing Image for 49 Wawali St 37 of 49 Listing Image for 49 Wawali St 38 of 49 Listing Image for 49 Wawali St 39 of 49 Listing Image for 49 Wawali St 40 of 49 Listing Image for 49 Wawali St 41 of 49 Listing Image for 49 Wawali St 42 of 49 Listing Image for 49 Wawali St 43 of 49 Listing Image for 49 Wawali St 44 of 49 Listing Image for 49 Wawali St 45 of 49 Listing Image for 49 Wawali St 46 of 49 Listing Image for 49 Wawali St 47 of 49 Listing Image for 49 Wawali St 48 of 49 Listing Image for 49 Wawali St 49 of 49

$1,145,000

Piilani Village III

49 Wawali St, Kihei

3 Beds 2 Baths 1,458 SqFt Residential MLS® # 409135 Date Sold: May 4, 2026
Sold
Closed: 03/27/2026
Listing Image for 491 Kilika Pl A 1 of 4 Listing Image for 491 Kilika Pl A 2 of 4 Listing Image for 491 Kilika Pl A 3 of 4 Listing Image for 491 Kilika Pl A 4 of 4

$799,000

Wailuku

491 Kilika Pl A, Wailuku

3 Beds 2 Baths 1,572 SqFt Residential MLS® # 409131 Date Sold: March 27, 2026
Sold
Closed: 03/27/2026
167 Maiaku St 166, Makawao/Olinda/Haliimaile

$1,625,000

Hokuula

167 Maiaku St 166, Makawao/Olinda/Haliimaile

4 Beds 3 Baths 1,456 SqFt Residential MLS® # 409123 Date Sold: March 27, 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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