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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Short Term Rental
Listing Image for 2777 S Kihei Rd G207 1 of 50 Listing Image for 2777 S Kihei Rd G207 2 of 50 Listing Image for 2777 S Kihei Rd G207 3 of 50 Listing Image for 2777 S Kihei Rd G207 4 of 50 Listing Image for 2777 S Kihei Rd G207 5 of 50 Listing Image for 2777 S Kihei Rd G207 6 of 50 Listing Image for 2777 S Kihei Rd G207 7 of 50 Listing Image for 2777 S Kihei Rd G207 8 of 50 Listing Image for 2777 S Kihei Rd G207 9 of 50 Listing Image for 2777 S Kihei Rd G207 10 of 50 Listing Image for 2777 S Kihei Rd G207 11 of 50 Listing Image for 2777 S Kihei Rd G207 12 of 50 Listing Image for 2777 S Kihei Rd G207 13 of 50 Listing Image for 2777 S Kihei Rd G207 14 of 50 Listing Image for 2777 S Kihei Rd G207 15 of 50 Listing Image for 2777 S Kihei Rd G207 16 of 50 Listing Image for 2777 S Kihei Rd G207 17 of 50 Listing Image for 2777 S Kihei Rd G207 18 of 50 Listing Image for 2777 S Kihei Rd G207 19 of 50 Listing Image for 2777 S Kihei Rd G207 20 of 50 Listing Image for 2777 S Kihei Rd G207 21 of 50 Listing Image for 2777 S Kihei Rd G207 22 of 50 Listing Image for 2777 S Kihei Rd G207 23 of 50 Listing Image for 2777 S Kihei Rd G207 24 of 50 Listing Image for 2777 S Kihei Rd G207 25 of 50 Listing Image for 2777 S Kihei Rd G207 26 of 50 Listing Image for 2777 S Kihei Rd G207 27 of 50 Listing Image for 2777 S Kihei Rd G207 28 of 50 Listing Image for 2777 S Kihei Rd G207 29 of 50 Listing Image for 2777 S Kihei Rd G207 30 of 50 Listing Image for 2777 S Kihei Rd G207 31 of 50 Listing Image for 2777 S Kihei Rd G207 32 of 50 Listing Image for 2777 S Kihei Rd G207 33 of 50 Listing Image for 2777 S Kihei Rd G207 34 of 50 Listing Image for 2777 S Kihei Rd G207 35 of 50 Listing Image for 2777 S Kihei Rd G207 36 of 50 Listing Image for 2777 S Kihei Rd G207 37 of 50 Listing Image for 2777 S Kihei Rd G207 38 of 50 Listing Image for 2777 S Kihei Rd G207 39 of 50 Listing Image for 2777 S Kihei Rd G207 40 of 50 Listing Image for 2777 S Kihei Rd G207 41 of 50 Listing Image for 2777 S Kihei Rd G207 42 of 50 Listing Image for 2777 S Kihei Rd G207 43 of 50 Listing Image for 2777 S Kihei Rd G207 44 of 50 Listing Image for 2777 S Kihei Rd G207 45 of 50 Listing Image for 2777 S Kihei Rd G207 46 of 50 Listing Image for 2777 S Kihei Rd G207 47 of 50 Listing Image for 2777 S Kihei Rd G207 48 of 50 Listing Image for 2777 S Kihei Rd G207 49 of 50 Listing Image for 2777 S Kihei Rd G207 50 of 50

$1,150,000

Maui Kamaole G207

2777 S Kihei Rd G207, Kihei

2 Beds 2 Baths 1,052 SqFt Residential MLS® # 408408

Days on Market: 245

Coldwell Banker Island Prop(S) Cell: 808-344-0180

Short Term Rental
Listing Image for 36 S Kihei Rd 603 1 of 37 Listing Image for 36 S Kihei Rd 603 2 of 37 Listing Image for 36 S Kihei Rd 603 3 of 37 Listing Image for 36 S Kihei Rd 603 4 of 37 Listing Image for 36 S Kihei Rd 603 5 of 37 Listing Image for 36 S Kihei Rd 603 6 of 37 Listing Image for 36 S Kihei Rd 603 7 of 37 Listing Image for 36 S Kihei Rd 603 8 of 37 Listing Image for 36 S Kihei Rd 603 9 of 37 Listing Image for 36 S Kihei Rd 603 10 of 37 Listing Image for 36 S Kihei Rd 603 11 of 37 Listing Image for 36 S Kihei Rd 603 12 of 37 Listing Image for 36 S Kihei Rd 603 13 of 37 Listing Image for 36 S Kihei Rd 603 14 of 37 Listing Image for 36 S Kihei Rd 603 15 of 37 Listing Image for 36 S Kihei Rd 603 16 of 37 Listing Image for 36 S Kihei Rd 603 17 of 37 Listing Image for 36 S Kihei Rd 603 18 of 37 Listing Image for 36 S Kihei Rd 603 19 of 37 Listing Image for 36 S Kihei Rd 603 20 of 37 Listing Image for 36 S Kihei Rd 603 21 of 37 Listing Image for 36 S Kihei Rd 603 22 of 37 Listing Image for 36 S Kihei Rd 603 23 of 37 Listing Image for 36 S Kihei Rd 603 24 of 37 Listing Image for 36 S Kihei Rd 603 25 of 37 Listing Image for 36 S Kihei Rd 603 26 of 37 Listing Image for 36 S Kihei Rd 603 27 of 37 Listing Image for 36 S Kihei Rd 603 28 of 37 Listing Image for 36 S Kihei Rd 603 29 of 37 Listing Image for 36 S Kihei Rd 603 30 of 37 Listing Image for 36 S Kihei Rd 603 31 of 37 Listing Image for 36 S Kihei Rd 603 32 of 37 Listing Image for 36 S Kihei Rd 603 33 of 37 Listing Image for 36 S Kihei Rd 603 34 of 37 Listing Image for 36 S Kihei Rd 603 35 of 37 Listing Image for 36 S Kihei Rd 603 36 of 37 Listing Image for 36 S Kihei Rd 603 37 of 37

$899,999

↓ $85,001

Kihei Beach 603

36 S Kihei Rd 603, Kihei

1 Bed 1 Bath 732 SqFt Residential MLS® # 408407

Days on Market: 245

Island Sotheby's International Realty(L) Cell: 808-495-6236

Listing Image for 4067 S Paua Way 1 of 42 Listing Image for 4067 S Paua Way 2 of 42 Listing Image for 4067 S Paua Way 3 of 42 Listing Image for 4067 S Paua Way 4 of 42 Listing Image for 4067 S Paua Way 5 of 42 Listing Image for 4067 S Paua Way 6 of 42 Listing Image for 4067 S Paua Way 7 of 42 Listing Image for 4067 S Paua Way 8 of 42 Listing Image for 4067 S Paua Way 9 of 42 Listing Image for 4067 S Paua Way 10 of 42 Listing Image for 4067 S Paua Way 11 of 42 Listing Image for 4067 S Paua Way 12 of 42 Listing Image for 4067 S Paua Way 13 of 42 Listing Image for 4067 S Paua Way 14 of 42 Listing Image for 4067 S Paua Way 15 of 42 Listing Image for 4067 S Paua Way 16 of 42 Listing Image for 4067 S Paua Way 17 of 42 Listing Image for 4067 S Paua Way 18 of 42 Listing Image for 4067 S Paua Way 19 of 42 Listing Image for 4067 S Paua Way 20 of 42 Listing Image for 4067 S Paua Way 21 of 42 Listing Image for 4067 S Paua Way 22 of 42 Listing Image for 4067 S Paua Way 23 of 42 Listing Image for 4067 S Paua Way 24 of 42 Listing Image for 4067 S Paua Way 25 of 42 Listing Image for 4067 S Paua Way 26 of 42 Listing Image for 4067 S Paua Way 27 of 42 Listing Image for 4067 S Paua Way 28 of 42 Listing Image for 4067 S Paua Way 29 of 42 Listing Image for 4067 S Paua Way 30 of 42 Listing Image for 4067 S Paua Way 31 of 42 Listing Image for 4067 S Paua Way 32 of 42 Listing Image for 4067 S Paua Way 33 of 42 Listing Image for 4067 S Paua Way 34 of 42 Listing Image for 4067 S Paua Way 35 of 42 Listing Image for 4067 S Paua Way 36 of 42 Listing Image for 4067 S Paua Way 37 of 42 Listing Image for 4067 S Paua Way 38 of 42 Listing Image for 4067 S Paua Way 39 of 42 Listing Image for 4067 S Paua Way 40 of 42 Listing Image for 4067 S Paua Way 41 of 42 Listing Image for 4067 S Paua Way 42 of 42

$1,745,000

↓ $50,000

Kapalani Estates

4067 S Paua Way, Napili/Kahana/Honokowai

3 Beds 2 Baths 1,492 SqFt Residential MLS® # 408392

Days on Market: 247

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

Listing Image for 95 & 285 Kekaulike Ave 1 of 50 Listing Image for 95 & 285 Kekaulike Ave 2 of 50 Listing Image for 95 & 285 Kekaulike Ave 3 of 50 Listing Image for 95 & 285 Kekaulike Ave 4 of 50 Listing Image for 95 & 285 Kekaulike Ave 5 of 50 Listing Image for 95 & 285 Kekaulike Ave 6 of 50 Listing Image for 95 & 285 Kekaulike Ave 7 of 50 Listing Image for 95 & 285 Kekaulike Ave 8 of 50 Listing Image for 95 & 285 Kekaulike Ave 9 of 50 Listing Image for 95 & 285 Kekaulike Ave 10 of 50 Listing Image for 95 & 285 Kekaulike Ave 11 of 50 Listing Image for 95 & 285 Kekaulike Ave 12 of 50 Listing Image for 95 & 285 Kekaulike Ave 13 of 50 Listing Image for 95 & 285 Kekaulike Ave 14 of 50 Listing Image for 95 & 285 Kekaulike Ave 15 of 50 Listing Image for 95 & 285 Kekaulike Ave 16 of 50 Listing Image for 95 & 285 Kekaulike Ave 17 of 50 Listing Image for 95 & 285 Kekaulike Ave 18 of 50 Listing Image for 95 & 285 Kekaulike Ave 19 of 50 Listing Image for 95 & 285 Kekaulike Ave 20 of 50 Listing Image for 95 & 285 Kekaulike Ave 21 of 50 Listing Image for 95 & 285 Kekaulike Ave 22 of 50 Listing Image for 95 & 285 Kekaulike Ave 23 of 50 Listing Image for 95 & 285 Kekaulike Ave 24 of 50 Listing Image for 95 & 285 Kekaulike Ave 25 of 50 Listing Image for 95 & 285 Kekaulike Ave 26 of 50 Listing Image for 95 & 285 Kekaulike Ave 27 of 50 Listing Image for 95 & 285 Kekaulike Ave 28 of 50 Listing Image for 95 & 285 Kekaulike Ave 29 of 50 Listing Image for 95 & 285 Kekaulike Ave 30 of 50 Listing Image for 95 & 285 Kekaulike Ave 31 of 50 Listing Image for 95 & 285 Kekaulike Ave 32 of 50 Listing Image for 95 & 285 Kekaulike Ave 33 of 50 Listing Image for 95 & 285 Kekaulike Ave 34 of 50 Listing Image for 95 & 285 Kekaulike Ave 35 of 50 Listing Image for 95 & 285 Kekaulike Ave 36 of 50 Listing Image for 95 & 285 Kekaulike Ave 37 of 50 Listing Image for 95 & 285 Kekaulike Ave 38 of 50 Listing Image for 95 & 285 Kekaulike Ave 39 of 50 Listing Image for 95 & 285 Kekaulike Ave 40 of 50 Listing Image for 95 & 285 Kekaulike Ave 41 of 50 Listing Image for 95 & 285 Kekaulike Ave 42 of 50 Listing Image for 95 & 285 Kekaulike Ave 43 of 50 Listing Image for 95 & 285 Kekaulike Ave 44 of 50 Listing Image for 95 & 285 Kekaulike Ave 45 of 50 Listing Image for 95 & 285 Kekaulike Ave 46 of 50 Listing Image for 95 & 285 Kekaulike Ave 47 of 50 Listing Image for 95 & 285 Kekaulike Ave 48 of 50 Listing Image for 95 & 285 Kekaulike Ave 49 of 50 Listing Image for 95 & 285 Kekaulike Ave 50 of 50

$9,950,000

Kula/Ulupalakua/Kanaio

95 & 285 Kekaulike Ave, Kula/Ulupalakua/Kanaio

3 Beds 2.5 Baths 5,316 SqFt Residential MLS® # 408390

Days on Market: 247

Island Sotheby's International Realty(M) Cell: 808-870-4114

In Escrow
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$2,495,000

↓ $55,000

Wailea Kialoa

199 E Ikea Moku Pl, Wailea/Makena

4 Beds 3 Baths 3,195 SqFt Residential MLS® # 408378

Days on Market: 247

Maui Real Estate Advisors LLC 808-875-4444

Short Term Rental
Listing Image for 110 Kaanapali Shores Pl 711 1 of 50 Listing Image for 110 Kaanapali Shores Pl 711 2 of 50 Listing Image for 110 Kaanapali Shores Pl 711 3 of 50 Listing Image for 110 Kaanapali Shores Pl 711 4 of 50 Listing Image for 110 Kaanapali Shores Pl 711 5 of 50 Listing Image for 110 Kaanapali Shores Pl 711 6 of 50 Listing Image for 110 Kaanapali Shores Pl 711 7 of 50 Listing Image for 110 Kaanapali Shores Pl 711 8 of 50 Listing Image for 110 Kaanapali Shores Pl 711 9 of 50 Listing Image for 110 Kaanapali Shores Pl 711 10 of 50 Listing Image for 110 Kaanapali Shores Pl 711 11 of 50 Listing Image for 110 Kaanapali Shores Pl 711 12 of 50 Listing Image for 110 Kaanapali Shores Pl 711 13 of 50 Listing Image for 110 Kaanapali Shores Pl 711 14 of 50 Listing Image for 110 Kaanapali Shores Pl 711 15 of 50 Listing Image for 110 Kaanapali Shores Pl 711 16 of 50 Listing Image for 110 Kaanapali Shores Pl 711 17 of 50 Listing Image for 110 Kaanapali Shores Pl 711 18 of 50 Listing Image for 110 Kaanapali Shores Pl 711 19 of 50 Listing Image for 110 Kaanapali Shores Pl 711 20 of 50 Listing Image for 110 Kaanapali Shores Pl 711 21 of 50 Listing Image for 110 Kaanapali Shores Pl 711 22 of 50 Listing Image for 110 Kaanapali Shores Pl 711 23 of 50 Listing Image for 110 Kaanapali Shores Pl 711 24 of 50 Listing Image for 110 Kaanapali Shores Pl 711 25 of 50 Listing Image for 110 Kaanapali Shores Pl 711 26 of 50 Listing Image for 110 Kaanapali Shores Pl 711 27 of 50 Listing Image for 110 Kaanapali Shores Pl 711 28 of 50 Listing Image for 110 Kaanapali Shores Pl 711 29 of 50 Listing Image for 110 Kaanapali Shores Pl 711 30 of 50 Listing Image for 110 Kaanapali Shores Pl 711 31 of 50 Listing Image for 110 Kaanapali Shores Pl 711 32 of 50 Listing Image for 110 Kaanapali Shores Pl 711 33 of 50 Listing Image for 110 Kaanapali Shores Pl 711 34 of 50 Listing Image for 110 Kaanapali Shores Pl 711 35 of 50 Listing Image for 110 Kaanapali Shores Pl 711 36 of 50 Listing Image for 110 Kaanapali Shores Pl 711 37 of 50 Listing Image for 110 Kaanapali Shores Pl 711 38 of 50 Listing Image for 110 Kaanapali Shores Pl 711 39 of 50 Listing Image for 110 Kaanapali Shores Pl 711 40 of 50 Listing Image for 110 Kaanapali Shores Pl 711 41 of 50 Listing Image for 110 Kaanapali Shores Pl 711 42 of 50 Listing Image for 110 Kaanapali Shores Pl 711 43 of 50 Listing Image for 110 Kaanapali Shores Pl 711 44 of 50 Listing Image for 110 Kaanapali Shores Pl 711 45 of 50 Listing Image for 110 Kaanapali Shores Pl 711 46 of 50 Listing Image for 110 Kaanapali Shores Pl 711 47 of 50 Listing Image for 110 Kaanapali Shores Pl 711 48 of 50 Listing Image for 110 Kaanapali Shores Pl 711 49 of 50 Listing Image for 110 Kaanapali Shores Pl 711 50 of 50

$1,750,000

↓ $245,000

Mahana 711

110 Kaanapali Shores Pl 711, Kaanapali

2 Beds 2 Baths 1,178 SqFt Residential MLS® # 408364

Days on Market: 250

Keller Williams Realty Maui-L Cell: 808-264-4617

Listing Image for 52 Lau Niu Way A 1 of 48 Listing Image for 52 Lau Niu Way A 2 of 48 Listing Image for 52 Lau Niu Way A 3 of 48 Listing Image for 52 Lau Niu Way A 4 of 48 Listing Image for 52 Lau Niu Way A 5 of 48 Listing Image for 52 Lau Niu Way A 6 of 48 Listing Image for 52 Lau Niu Way A 7 of 48 Listing Image for 52 Lau Niu Way A 8 of 48 Listing Image for 52 Lau Niu Way A 9 of 48 Listing Image for 52 Lau Niu Way A 10 of 48 Listing Image for 52 Lau Niu Way A 11 of 48 Listing Image for 52 Lau Niu Way A 12 of 48 Listing Image for 52 Lau Niu Way A 13 of 48 Listing Image for 52 Lau Niu Way A 14 of 48 Listing Image for 52 Lau Niu Way A 15 of 48 Listing Image for 52 Lau Niu Way A 16 of 48 Listing Image for 52 Lau Niu Way A 17 of 48 Listing Image for 52 Lau Niu Way A 18 of 48 Listing Image for 52 Lau Niu Way A 19 of 48 Listing Image for 52 Lau Niu Way A 20 of 48 Listing Image for 52 Lau Niu Way A 21 of 48 Listing Image for 52 Lau Niu Way A 22 of 48 Listing Image for 52 Lau Niu Way A 23 of 48 Listing Image for 52 Lau Niu Way A 24 of 48 Listing Image for 52 Lau Niu Way A 25 of 48 Listing Image for 52 Lau Niu Way A 26 of 48 Listing Image for 52 Lau Niu Way A 27 of 48 Listing Image for 52 Lau Niu Way A 28 of 48 Listing Image for 52 Lau Niu Way A 29 of 48 Listing Image for 52 Lau Niu Way A 30 of 48 Listing Image for 52 Lau Niu Way A 31 of 48 Listing Image for 52 Lau Niu Way A 32 of 48 Listing Image for 52 Lau Niu Way A 33 of 48 Listing Image for 52 Lau Niu Way A 34 of 48 Listing Image for 52 Lau Niu Way A 35 of 48 Listing Image for 52 Lau Niu Way A 36 of 48 Listing Image for 52 Lau Niu Way A 37 of 48 Listing Image for 52 Lau Niu Way A 38 of 48 Listing Image for 52 Lau Niu Way A 39 of 48 Listing Image for 52 Lau Niu Way A 40 of 48 Listing Image for 52 Lau Niu Way A 41 of 48 Listing Image for 52 Lau Niu Way A 42 of 48 Listing Image for 52 Lau Niu Way A 43 of 48 Listing Image for 52 Lau Niu Way A 44 of 48 Listing Image for 52 Lau Niu Way A 45 of 48 Listing Image for 52 Lau Niu Way A 46 of 48 Listing Image for 52 Lau Niu Way A 47 of 48 Listing Image for 52 Lau Niu Way A 48 of 48

$2,499,000

↓ $96,000

Mahanalua Nui

52 Lau Niu Way A, Lahaina

3 Beds 2 Baths 1,206 SqFt Residential MLS® # 408355

Days on Market: 251

Coldwell Banker Island Prop-Ku Cell: 808-250-0205

View 7 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: 07/23/2026
Listing Image for 78 Aleiki Pl 1 of 50 Listing Image for 78 Aleiki Pl 2 of 50 Listing Image for 78 Aleiki Pl 3 of 50 Listing Image for 78 Aleiki Pl 4 of 50 Listing Image for 78 Aleiki Pl 5 of 50 Listing Image for 78 Aleiki Pl 6 of 50 Listing Image for 78 Aleiki Pl 7 of 50 Listing Image for 78 Aleiki Pl 8 of 50 Listing Image for 78 Aleiki Pl 9 of 50 Listing Image for 78 Aleiki Pl 10 of 50 Listing Image for 78 Aleiki Pl 11 of 50 Listing Image for 78 Aleiki Pl 12 of 50 Listing Image for 78 Aleiki Pl 13 of 50 Listing Image for 78 Aleiki Pl 14 of 50 Listing Image for 78 Aleiki Pl 15 of 50 Listing Image for 78 Aleiki Pl 16 of 50 Listing Image for 78 Aleiki Pl 17 of 50 Listing Image for 78 Aleiki Pl 18 of 50 Listing Image for 78 Aleiki Pl 19 of 50 Listing Image for 78 Aleiki Pl 20 of 50 Listing Image for 78 Aleiki Pl 21 of 50 Listing Image for 78 Aleiki Pl 22 of 50 Listing Image for 78 Aleiki Pl 23 of 50 Listing Image for 78 Aleiki Pl 24 of 50 Listing Image for 78 Aleiki Pl 25 of 50 Listing Image for 78 Aleiki Pl 26 of 50 Listing Image for 78 Aleiki Pl 27 of 50 Listing Image for 78 Aleiki Pl 28 of 50 Listing Image for 78 Aleiki Pl 29 of 50 Listing Image for 78 Aleiki Pl 30 of 50 Listing Image for 78 Aleiki Pl 31 of 50 Listing Image for 78 Aleiki Pl 32 of 50 Listing Image for 78 Aleiki Pl 33 of 50 Listing Image for 78 Aleiki Pl 34 of 50 Listing Image for 78 Aleiki Pl 35 of 50 Listing Image for 78 Aleiki Pl 36 of 50 Listing Image for 78 Aleiki Pl 37 of 50 Listing Image for 78 Aleiki Pl 38 of 50 Listing Image for 78 Aleiki Pl 39 of 50 Listing Image for 78 Aleiki Pl 40 of 50 Listing Image for 78 Aleiki Pl 41 of 50 Listing Image for 78 Aleiki Pl 42 of 50 Listing Image for 78 Aleiki Pl 43 of 50 Listing Image for 78 Aleiki Pl 44 of 50 Listing Image for 78 Aleiki Pl 45 of 50 Listing Image for 78 Aleiki Pl 46 of 50 Listing Image for 78 Aleiki Pl 47 of 50 Listing Image for 78 Aleiki Pl 48 of 50 Listing Image for 78 Aleiki Pl 49 of 50 Listing Image for 78 Aleiki Pl 50 of 50

$2,430,000

↓ $365,000

Spreckelsville/Paia/Kuau

78 Aleiki Pl, Spreckelsville/Paia/Kuau

4 Beds 3 Baths 2,082 SqFt Residential MLS® # 407464 Date Sold: July 23, 2026
Sold
Closed: 12/04/2025
Listing Image for 2430 S Kihei Rd 515 1 of 50 Listing Image for 2430 S Kihei Rd 515 2 of 50 Listing Image for 2430 S Kihei Rd 515 3 of 50 Listing Image for 2430 S Kihei Rd 515 4 of 50 Listing Image for 2430 S Kihei Rd 515 5 of 50 Listing Image for 2430 S Kihei Rd 515 6 of 50 Listing Image for 2430 S Kihei Rd 515 7 of 50 Listing Image for 2430 S Kihei Rd 515 8 of 50 Listing Image for 2430 S Kihei Rd 515 9 of 50 Listing Image for 2430 S Kihei Rd 515 10 of 50 Listing Image for 2430 S Kihei Rd 515 11 of 50 Listing Image for 2430 S Kihei Rd 515 12 of 50 Listing Image for 2430 S Kihei Rd 515 13 of 50 Listing Image for 2430 S Kihei Rd 515 14 of 50 Listing Image for 2430 S Kihei Rd 515 15 of 50 Listing Image for 2430 S Kihei Rd 515 16 of 50 Listing Image for 2430 S Kihei Rd 515 17 of 50 Listing Image for 2430 S Kihei Rd 515 18 of 50 Listing Image for 2430 S Kihei Rd 515 19 of 50 Listing Image for 2430 S Kihei Rd 515 20 of 50 Listing Image for 2430 S Kihei Rd 515 21 of 50 Listing Image for 2430 S Kihei Rd 515 22 of 50 Listing Image for 2430 S Kihei Rd 515 23 of 50 Listing Image for 2430 S Kihei Rd 515 24 of 50 Listing Image for 2430 S Kihei Rd 515 25 of 50 Listing Image for 2430 S Kihei Rd 515 26 of 50 Listing Image for 2430 S Kihei Rd 515 27 of 50 Listing Image for 2430 S Kihei Rd 515 28 of 50 Listing Image for 2430 S Kihei Rd 515 29 of 50 Listing Image for 2430 S Kihei Rd 515 30 of 50 Listing Image for 2430 S Kihei Rd 515 31 of 50 Listing Image for 2430 S Kihei Rd 515 32 of 50 Listing Image for 2430 S Kihei Rd 515 33 of 50 Listing Image for 2430 S Kihei Rd 515 34 of 50 Listing Image for 2430 S Kihei Rd 515 35 of 50 Listing Image for 2430 S Kihei Rd 515 36 of 50 Listing Image for 2430 S Kihei Rd 515 37 of 50 Listing Image for 2430 S Kihei Rd 515 38 of 50 Listing Image for 2430 S Kihei Rd 515 39 of 50 Listing Image for 2430 S Kihei Rd 515 40 of 50 Listing Image for 2430 S Kihei Rd 515 41 of 50 Listing Image for 2430 S Kihei Rd 515 42 of 50 Listing Image for 2430 S Kihei Rd 515 43 of 50 Listing Image for 2430 S Kihei Rd 515 44 of 50 Listing Image for 2430 S Kihei Rd 515 45 of 50 Listing Image for 2430 S Kihei Rd 515 46 of 50 Listing Image for 2430 S Kihei Rd 515 47 of 50 Listing Image for 2430 S Kihei Rd 515 48 of 50 Listing Image for 2430 S Kihei Rd 515 49 of 50 Listing Image for 2430 S Kihei Rd 515 50 of 50

$1,850,000

Royal Mauian 515

2430 S Kihei Rd 515, Kihei

2 Beds 2 Baths 806 SqFt Residential MLS® # 407462 Date Sold: December 4, 2025
Sold
Closed: 03/27/2026
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$1,235,000

↓ $40,000

Waiolani Mauka

40 Koani Loop 40, Wailuku

3 Beds 2 Baths 1,476 SqFt Residential MLS® # 407461 Date Sold: March 27, 2026
Sold
Closed: 04/08/2026
Listing Image for 83 W Kapu Pl 1 of 29 Listing Image for 83 W Kapu Pl 2 of 29 Listing Image for 83 W Kapu Pl 3 of 29 Listing Image for 83 W Kapu Pl 4 of 29 Listing Image for 83 W Kapu Pl 5 of 29 Listing Image for 83 W Kapu Pl 6 of 29 Listing Image for 83 W Kapu Pl 7 of 29 Listing Image for 83 W Kapu Pl 8 of 29 Listing Image for 83 W Kapu Pl 9 of 29 Listing Image for 83 W Kapu Pl 10 of 29 Listing Image for 83 W Kapu Pl 11 of 29 Listing Image for 83 W Kapu Pl 12 of 29 Listing Image for 83 W Kapu Pl 13 of 29 Listing Image for 83 W Kapu Pl 14 of 29 Listing Image for 83 W Kapu Pl 15 of 29 Listing Image for 83 W Kapu Pl 16 of 29 Listing Image for 83 W Kapu Pl 17 of 29 Listing Image for 83 W Kapu Pl 18 of 29 Listing Image for 83 W Kapu Pl 19 of 29 Listing Image for 83 W Kapu Pl 20 of 29 Listing Image for 83 W Kapu Pl 21 of 29 Listing Image for 83 W Kapu Pl 22 of 29 Listing Image for 83 W Kapu Pl 23 of 29 Listing Image for 83 W Kapu Pl 24 of 29 Listing Image for 83 W Kapu Pl 25 of 29 Listing Image for 83 W Kapu Pl 26 of 29 Listing Image for 83 W Kapu Pl 27 of 29 Listing Image for 83 W Kapu Pl 28 of 29 Listing Image for 83 W Kapu Pl 29 of 29

$2,125,000

Kihei

83 W Kapu Pl, Kihei

0 Beds 0 Baths 0 SqFt Land MLS® # 407455 Date Sold: April 8, 2026
Buying Real Estate on Maui

Buying Real Estate on Maui

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

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Sold
Closed: 02/25/2026
Listing Image for 500 Kapalua Dr 23v2 1 of 33 Listing Image for 500 Kapalua Dr 23v2 2 of 33 Listing Image for 500 Kapalua Dr 23v2 3 of 33 Listing Image for 500 Kapalua Dr 23v2 4 of 33 Listing Image for 500 Kapalua Dr 23v2 5 of 33 Listing Image for 500 Kapalua Dr 23v2 6 of 33 Listing Image for 500 Kapalua Dr 23v2 7 of 33 Listing Image for 500 Kapalua Dr 23v2 8 of 33 Listing Image for 500 Kapalua Dr 23v2 9 of 33 Listing Image for 500 Kapalua Dr 23v2 10 of 33 Listing Image for 500 Kapalua Dr 23v2 11 of 33 Listing Image for 500 Kapalua Dr 23v2 12 of 33 Listing Image for 500 Kapalua Dr 23v2 13 of 33 Listing Image for 500 Kapalua Dr 23v2 14 of 33 Listing Image for 500 Kapalua Dr 23v2 15 of 33 Listing Image for 500 Kapalua Dr 23v2 16 of 33 Listing Image for 500 Kapalua Dr 23v2 17 of 33 Listing Image for 500 Kapalua Dr 23v2 18 of 33 Listing Image for 500 Kapalua Dr 23v2 19 of 33 Listing Image for 500 Kapalua Dr 23v2 20 of 33 Listing Image for 500 Kapalua Dr 23v2 21 of 33 Listing Image for 500 Kapalua Dr 23v2 22 of 33 Listing Image for 500 Kapalua Dr 23v2 23 of 33 Listing Image for 500 Kapalua Dr 23v2 24 of 33 Listing Image for 500 Kapalua Dr 23v2 25 of 33 Listing Image for 500 Kapalua Dr 23v2 26 of 33 Listing Image for 500 Kapalua Dr 23v2 27 of 33 Listing Image for 500 Kapalua Dr 23v2 28 of 33 Listing Image for 500 Kapalua Dr 23v2 29 of 33 Listing Image for 500 Kapalua Dr 23v2 30 of 33 Listing Image for 500 Kapalua Dr 23v2 31 of 33 Listing Image for 500 Kapalua Dr 23v2 32 of 33 Listing Image for 500 Kapalua Dr 23v2 33 of 33

$1,335,000

Kapalua Golf Villas 23V2

500 Kapalua Dr 23v2, Kapalua

1 Bed 2 Baths 899 SqFt Residential MLS® # 407453 Date Sold: February 25, 2026
Sold
Closed: 12/15/2025
Listing Image for 35006 Piilani Hwy 1 of 2 Listing Image for 35006 Piilani Hwy 2 of 2

$850,000

Kaupo

35006 Piilani Hwy, Kaupo

1 Bed 1 Bath 872 SqFt Residential MLS® # 407452 Date Sold: December 15, 2025
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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