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

$1,995,000

↓ $100,000

Kai Malu 43B

19 Kai La Pl 43b, Wailea/Makena

3 Beds 2.5 Baths 1,786 SqFt Residential MLS® # 406843

Days on Market: 400

Coldwell Banker Island Prop(S) Cell: 808-280-7728

In Escrow
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$995,000

Molokai

10464 Kamehameha V Hwy, Molokai

4 Beds 2 Baths 1,598 SqFt Residential MLS® # 406834

Days on Market: 401

Tropical Island Properties LLC

Listing Image for 50 Puu Anoano St 3905 1 of 37 Listing Image for 50 Puu Anoano St 3905 2 of 37 Listing Image for 50 Puu Anoano St 3905 3 of 37 Listing Image for 50 Puu Anoano St 3905 4 of 37 Listing Image for 50 Puu Anoano St 3905 5 of 37 Listing Image for 50 Puu Anoano St 3905 6 of 37 Listing Image for 50 Puu Anoano St 3905 7 of 37 Listing Image for 50 Puu Anoano St 3905 8 of 37 Listing Image for 50 Puu Anoano St 3905 9 of 37 Listing Image for 50 Puu Anoano St 3905 10 of 37 Listing Image for 50 Puu Anoano St 3905 11 of 37 Listing Image for 50 Puu Anoano St 3905 12 of 37 Listing Image for 50 Puu Anoano St 3905 13 of 37 Listing Image for 50 Puu Anoano St 3905 14 of 37 Listing Image for 50 Puu Anoano St 3905 15 of 37 Listing Image for 50 Puu Anoano St 3905 16 of 37 Listing Image for 50 Puu Anoano St 3905 17 of 37 Listing Image for 50 Puu Anoano St 3905 18 of 37 Listing Image for 50 Puu Anoano St 3905 19 of 37 Listing Image for 50 Puu Anoano St 3905 20 of 37 Listing Image for 50 Puu Anoano St 3905 21 of 37 Listing Image for 50 Puu Anoano St 3905 22 of 37 Listing Image for 50 Puu Anoano St 3905 23 of 37 Listing Image for 50 Puu Anoano St 3905 24 of 37 Listing Image for 50 Puu Anoano St 3905 25 of 37 Listing Image for 50 Puu Anoano St 3905 26 of 37 Listing Image for 50 Puu Anoano St 3905 27 of 37 Listing Image for 50 Puu Anoano St 3905 28 of 37 Listing Image for 50 Puu Anoano St 3905 29 of 37 Listing Image for 50 Puu Anoano St 3905 30 of 37 Listing Image for 50 Puu Anoano St 3905 31 of 37 Listing Image for 50 Puu Anoano St 3905 32 of 37 Listing Image for 50 Puu Anoano St 3905 33 of 37 Listing Image for 50 Puu Anoano St 3905 34 of 37 Listing Image for 50 Puu Anoano St 3905 35 of 37 Listing Image for 50 Puu Anoano St 3905 36 of 37 Listing Image for 50 Puu Anoano St 3905 37 of 37

$950,000

↓ $45,000

Masters 3905

50 Puu Anoano St 3905, Kaanapali

1 Bed 1 Bath 901 SqFt Residential MLS® # 406864

Days on Market: 398

Lowson & Associates laurie@lowson.com

Listing Image for 14 Coconut Grove Ln D14 1 of 40 Listing Image for 14 Coconut Grove Ln D14 2 of 40 Listing Image for 14 Coconut Grove Ln D14 3 of 40 Listing Image for 14 Coconut Grove Ln D14 4 of 40 Listing Image for 14 Coconut Grove Ln D14 5 of 40 Listing Image for 14 Coconut Grove Ln D14 6 of 40 Listing Image for 14 Coconut Grove Ln D14 7 of 40 Listing Image for 14 Coconut Grove Ln D14 8 of 40 Listing Image for 14 Coconut Grove Ln D14 9 of 40 Listing Image for 14 Coconut Grove Ln D14 10 of 40 Listing Image for 14 Coconut Grove Ln D14 11 of 40 Listing Image for 14 Coconut Grove Ln D14 12 of 40 Listing Image for 14 Coconut Grove Ln D14 13 of 40 Listing Image for 14 Coconut Grove Ln D14 14 of 40 Listing Image for 14 Coconut Grove Ln D14 15 of 40 Listing Image for 14 Coconut Grove Ln D14 16 of 40 Listing Image for 14 Coconut Grove Ln D14 17 of 40 Listing Image for 14 Coconut Grove Ln D14 18 of 40 Listing Image for 14 Coconut Grove Ln D14 19 of 40 Listing Image for 14 Coconut Grove Ln D14 20 of 40 Listing Image for 14 Coconut Grove Ln D14 21 of 40 Listing Image for 14 Coconut Grove Ln D14 22 of 40 Listing Image for 14 Coconut Grove Ln D14 23 of 40 Listing Image for 14 Coconut Grove Ln D14 24 of 40 Listing Image for 14 Coconut Grove Ln D14 25 of 40 Listing Image for 14 Coconut Grove Ln D14 26 of 40 Listing Image for 14 Coconut Grove Ln D14 27 of 40 Listing Image for 14 Coconut Grove Ln D14 28 of 40 Listing Image for 14 Coconut Grove Ln D14 29 of 40 Listing Image for 14 Coconut Grove Ln D14 30 of 40 Listing Image for 14 Coconut Grove Ln D14 31 of 40 Listing Image for 14 Coconut Grove Ln D14 32 of 40 Listing Image for 14 Coconut Grove Ln D14 33 of 40 Listing Image for 14 Coconut Grove Ln D14 34 of 40 Listing Image for 14 Coconut Grove Ln D14 35 of 40 Listing Image for 14 Coconut Grove Ln D14 36 of 40 Listing Image for 14 Coconut Grove Ln D14 37 of 40 Listing Image for 14 Coconut Grove Ln D14 38 of 40 Listing Image for 14 Coconut Grove Ln D14 39 of 40 Listing Image for 14 Coconut Grove Ln D14 40 of 40

$5,150,000

↓ $415,000

Coconut Grove D14

14 Coconut Grove Ln D14, Kapalua

3 Beds 3.5 Baths 2,625 SqFt Residential MLS® # 406667

Days on Market: 416

Hawaii Life (L) Cell: 808-280-4881

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

$5,199,000

↓ $46,000

Lanikeha Phase I

44 Loli'i Pl, Kaanapali

4 Beds 5 Baths 3,691 SqFt Residential MLS® # 406460

Days on Market: 439

Welcome Hawaii Properties Cell: 808-280-2480

Listing Image for 700 Halelea St 5 1 of 50 Listing Image for 700 Halelea St 5 2 of 50 Listing Image for 700 Halelea St 5 3 of 50 Listing Image for 700 Halelea St 5 4 of 50 Listing Image for 700 Halelea St 5 5 of 50 Listing Image for 700 Halelea St 5 6 of 50 Listing Image for 700 Halelea St 5 7 of 50 Listing Image for 700 Halelea St 5 8 of 50 Listing Image for 700 Halelea St 5 9 of 50 Listing Image for 700 Halelea St 5 10 of 50 Listing Image for 700 Halelea St 5 11 of 50 Listing Image for 700 Halelea St 5 12 of 50 Listing Image for 700 Halelea St 5 13 of 50 Listing Image for 700 Halelea St 5 14 of 50 Listing Image for 700 Halelea St 5 15 of 50 Listing Image for 700 Halelea St 5 16 of 50 Listing Image for 700 Halelea St 5 17 of 50 Listing Image for 700 Halelea St 5 18 of 50 Listing Image for 700 Halelea St 5 19 of 50 Listing Image for 700 Halelea St 5 20 of 50 Listing Image for 700 Halelea St 5 21 of 50 Listing Image for 700 Halelea St 5 22 of 50 Listing Image for 700 Halelea St 5 23 of 50 Listing Image for 700 Halelea St 5 24 of 50 Listing Image for 700 Halelea St 5 25 of 50 Listing Image for 700 Halelea St 5 26 of 50 Listing Image for 700 Halelea St 5 27 of 50 Listing Image for 700 Halelea St 5 28 of 50 Listing Image for 700 Halelea St 5 29 of 50 Listing Image for 700 Halelea St 5 30 of 50 Listing Image for 700 Halelea St 5 31 of 50 Listing Image for 700 Halelea St 5 32 of 50 Listing Image for 700 Halelea St 5 33 of 50 Listing Image for 700 Halelea St 5 34 of 50 Listing Image for 700 Halelea St 5 35 of 50 Listing Image for 700 Halelea St 5 36 of 50 Listing Image for 700 Halelea St 5 37 of 50 Listing Image for 700 Halelea St 5 38 of 50 Listing Image for 700 Halelea St 5 39 of 50 Listing Image for 700 Halelea St 5 40 of 50 Listing Image for 700 Halelea St 5 41 of 50 Listing Image for 700 Halelea St 5 42 of 50 Listing Image for 700 Halelea St 5 43 of 50 Listing Image for 700 Halelea St 5 44 of 50 Listing Image for 700 Halelea St 5 45 of 50 Listing Image for 700 Halelea St 5 46 of 50 Listing Image for 700 Halelea St 5 47 of 50 Listing Image for 700 Halelea St 5 48 of 50 Listing Image for 700 Halelea St 5 49 of 50 Listing Image for 700 Halelea St 5 50 of 50

$1,799,000

↓ $96,000

Hokulani

700 Halelea St 5, Kihei

4 Beds 3 Baths 2,516 SqFt Residential MLS® # 406610

Days on Market: 422

Hawaii Life (W) Cell: 808-283-8192

Listing Image for 2259 Mokuhau Rd 1 of 27 Listing Image for 2259 Mokuhau Rd 2 of 27 Listing Image for 2259 Mokuhau Rd 3 of 27 Listing Image for 2259 Mokuhau Rd 4 of 27 Listing Image for 2259 Mokuhau Rd 5 of 27 Listing Image for 2259 Mokuhau Rd 6 of 27 Listing Image for 2259 Mokuhau Rd 7 of 27 Listing Image for 2259 Mokuhau Rd 8 of 27 Listing Image for 2259 Mokuhau Rd 9 of 27 Listing Image for 2259 Mokuhau Rd 10 of 27 Listing Image for 2259 Mokuhau Rd 11 of 27 Listing Image for 2259 Mokuhau Rd 12 of 27 Listing Image for 2259 Mokuhau Rd 13 of 27 Listing Image for 2259 Mokuhau Rd 14 of 27 Listing Image for 2259 Mokuhau Rd 15 of 27 Listing Image for 2259 Mokuhau Rd 16 of 27 Listing Image for 2259 Mokuhau Rd 17 of 27 Listing Image for 2259 Mokuhau Rd 18 of 27 Listing Image for 2259 Mokuhau Rd 19 of 27 Listing Image for 2259 Mokuhau Rd 20 of 27 Listing Image for 2259 Mokuhau Rd 21 of 27 Listing Image for 2259 Mokuhau Rd 22 of 27 Listing Image for 2259 Mokuhau Rd 23 of 27 Listing Image for 2259 Mokuhau Rd 24 of 27 Listing Image for 2259 Mokuhau Rd 25 of 27 Listing Image for 2259 Mokuhau Rd 26 of 27 Listing Image for 2259 Mokuhau Rd 27 of 27

$1,550,000

↓ $100,000

Happy Valley

2259 Mokuhau Rd, Wailuku

3 Beds 2 Baths 1,748 SqFt Residential MLS® # 406718

Days on Market: 412

Blue Hawaii Realty Inc

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: 08/29/2025
315 Mauli St, Kaanapali

$3,000,000

Kaanapali

315 Mauli St, Kaanapali

4 Beds 3.5 Baths 3,032 SqFt Residential MLS® # 407003 Date Sold: August 29, 2025
Sold
Closed: 10/27/2025
Listing Image for 14 Ka Dr 1 of 50 Listing Image for 14 Ka Dr 2 of 50 Listing Image for 14 Ka Dr 3 of 50 Listing Image for 14 Ka Dr 4 of 50 Listing Image for 14 Ka Dr 5 of 50 Listing Image for 14 Ka Dr 6 of 50 Listing Image for 14 Ka Dr 7 of 50 Listing Image for 14 Ka Dr 8 of 50 Listing Image for 14 Ka Dr 9 of 50 Listing Image for 14 Ka Dr 10 of 50 Listing Image for 14 Ka Dr 11 of 50 Listing Image for 14 Ka Dr 12 of 50 Listing Image for 14 Ka Dr 13 of 50 Listing Image for 14 Ka Dr 14 of 50 Listing Image for 14 Ka Dr 15 of 50 Listing Image for 14 Ka Dr 16 of 50 Listing Image for 14 Ka Dr 17 of 50 Listing Image for 14 Ka Dr 18 of 50 Listing Image for 14 Ka Dr 19 of 50 Listing Image for 14 Ka Dr 20 of 50 Listing Image for 14 Ka Dr 21 of 50 Listing Image for 14 Ka Dr 22 of 50 Listing Image for 14 Ka Dr 23 of 50 Listing Image for 14 Ka Dr 24 of 50 Listing Image for 14 Ka Dr 25 of 50 Listing Image for 14 Ka Dr 26 of 50 Listing Image for 14 Ka Dr 27 of 50 Listing Image for 14 Ka Dr 28 of 50 Listing Image for 14 Ka Dr 29 of 50 Listing Image for 14 Ka Dr 30 of 50 Listing Image for 14 Ka Dr 31 of 50 Listing Image for 14 Ka Dr 32 of 50 Listing Image for 14 Ka Dr 33 of 50 Listing Image for 14 Ka Dr 34 of 50 Listing Image for 14 Ka Dr 35 of 50 Listing Image for 14 Ka Dr 36 of 50 Listing Image for 14 Ka Dr 37 of 50 Listing Image for 14 Ka Dr 38 of 50 Listing Image for 14 Ka Dr 39 of 50 Listing Image for 14 Ka Dr 40 of 50 Listing Image for 14 Ka Dr 41 of 50 Listing Image for 14 Ka Dr 42 of 50 Listing Image for 14 Ka Dr 43 of 50 Listing Image for 14 Ka Dr 44 of 50 Listing Image for 14 Ka Dr 45 of 50 Listing Image for 14 Ka Dr 46 of 50 Listing Image for 14 Ka Dr 47 of 50 Listing Image for 14 Ka Dr 48 of 50 Listing Image for 14 Ka Dr 49 of 50 Listing Image for 14 Ka Dr 50 of 50

$1,695,000

Kula Kai

14 Ka Dr, Kula/Ulupalakua/Kanaio

4 Beds 2.5 Baths 2,240 SqFt Residential MLS® # 406989 Date Sold: October 27, 2025
Sold
Closed: 12/29/2025
Listing Image for 394 Kahoma Village Loop 55 1 of 21 Listing Image for 394 Kahoma Village Loop 55 2 of 21 Listing Image for 394 Kahoma Village Loop 55 3 of 21 Listing Image for 394 Kahoma Village Loop 55 4 of 21 Listing Image for 394 Kahoma Village Loop 55 5 of 21 Listing Image for 394 Kahoma Village Loop 55 6 of 21 Listing Image for 394 Kahoma Village Loop 55 7 of 21 Listing Image for 394 Kahoma Village Loop 55 8 of 21 Listing Image for 394 Kahoma Village Loop 55 9 of 21 Listing Image for 394 Kahoma Village Loop 55 10 of 21 Listing Image for 394 Kahoma Village Loop 55 11 of 21 Listing Image for 394 Kahoma Village Loop 55 12 of 21 Listing Image for 394 Kahoma Village Loop 55 13 of 21 Listing Image for 394 Kahoma Village Loop 55 14 of 21 Listing Image for 394 Kahoma Village Loop 55 15 of 21 Listing Image for 394 Kahoma Village Loop 55 16 of 21 Listing Image for 394 Kahoma Village Loop 55 17 of 21 Listing Image for 394 Kahoma Village Loop 55 18 of 21 Listing Image for 394 Kahoma Village Loop 55 19 of 21 Listing Image for 394 Kahoma Village Loop 55 20 of 21 Listing Image for 394 Kahoma Village Loop 55 21 of 21

$1,379,000

Kahoma Village 55

394 Kahoma Village Loop 55, Lahaina

3 Beds 2.5 Baths 1,368 SqFt Residential MLS® # 406973 Date Sold: December 29, 2025
Sold
Closed: 12/02/2025
Listing Image for 2625 Kokomo Rd 1 of 50 Listing Image for 2625 Kokomo Rd 2 of 50 Listing Image for 2625 Kokomo Rd 3 of 50 Listing Image for 2625 Kokomo Rd 4 of 50 Listing Image for 2625 Kokomo Rd 5 of 50 Listing Image for 2625 Kokomo Rd 6 of 50 Listing Image for 2625 Kokomo Rd 7 of 50 Listing Image for 2625 Kokomo Rd 8 of 50 Listing Image for 2625 Kokomo Rd 9 of 50 Listing Image for 2625 Kokomo Rd 10 of 50 Listing Image for 2625 Kokomo Rd 11 of 50 Listing Image for 2625 Kokomo Rd 12 of 50 Listing Image for 2625 Kokomo Rd 13 of 50 Listing Image for 2625 Kokomo Rd 14 of 50 Listing Image for 2625 Kokomo Rd 15 of 50 Listing Image for 2625 Kokomo Rd 16 of 50 Listing Image for 2625 Kokomo Rd 17 of 50 Listing Image for 2625 Kokomo Rd 18 of 50 Listing Image for 2625 Kokomo Rd 19 of 50 Listing Image for 2625 Kokomo Rd 20 of 50 Listing Image for 2625 Kokomo Rd 21 of 50 Listing Image for 2625 Kokomo Rd 22 of 50 Listing Image for 2625 Kokomo Rd 23 of 50 Listing Image for 2625 Kokomo Rd 24 of 50 Listing Image for 2625 Kokomo Rd 25 of 50 Listing Image for 2625 Kokomo Rd 26 of 50 Listing Image for 2625 Kokomo Rd 27 of 50 Listing Image for 2625 Kokomo Rd 28 of 50 Listing Image for 2625 Kokomo Rd 29 of 50 Listing Image for 2625 Kokomo Rd 30 of 50 Listing Image for 2625 Kokomo Rd 31 of 50 Listing Image for 2625 Kokomo Rd 32 of 50 Listing Image for 2625 Kokomo Rd 33 of 50 Listing Image for 2625 Kokomo Rd 34 of 50 Listing Image for 2625 Kokomo Rd 35 of 50 Listing Image for 2625 Kokomo Rd 36 of 50 Listing Image for 2625 Kokomo Rd 37 of 50 Listing Image for 2625 Kokomo Rd 38 of 50 Listing Image for 2625 Kokomo Rd 39 of 50 Listing Image for 2625 Kokomo Rd 40 of 50 Listing Image for 2625 Kokomo Rd 41 of 50 Listing Image for 2625 Kokomo Rd 42 of 50 Listing Image for 2625 Kokomo Rd 43 of 50 Listing Image for 2625 Kokomo Rd 44 of 50 Listing Image for 2625 Kokomo Rd 45 of 50 Listing Image for 2625 Kokomo Rd 46 of 50 Listing Image for 2625 Kokomo Rd 47 of 50 Listing Image for 2625 Kokomo Rd 48 of 50 Listing Image for 2625 Kokomo Rd 49 of 50 Listing Image for 2625 Kokomo Rd 50 of 50

$3,000,000

Haiku

2625 Kokomo Rd, Haiku

4 Beds 3 Baths 2,623 SqFt Residential MLS® # 407042 Date Sold: December 2, 2025
Sold
Closed: 12/26/2025
Listing Image for 35 Kau St 1 of 50 Listing Image for 35 Kau St 2 of 50 Listing Image for 35 Kau St 3 of 50 Listing Image for 35 Kau St 4 of 50 Listing Image for 35 Kau St 5 of 50 Listing Image for 35 Kau St 6 of 50 Listing Image for 35 Kau St 7 of 50 Listing Image for 35 Kau St 8 of 50 Listing Image for 35 Kau St 9 of 50 Listing Image for 35 Kau St 10 of 50 Listing Image for 35 Kau St 11 of 50 Listing Image for 35 Kau St 12 of 50 Listing Image for 35 Kau St 13 of 50 Listing Image for 35 Kau St 14 of 50 Listing Image for 35 Kau St 15 of 50 Listing Image for 35 Kau St 16 of 50 Listing Image for 35 Kau St 17 of 50 Listing Image for 35 Kau St 18 of 50 Listing Image for 35 Kau St 19 of 50 Listing Image for 35 Kau St 20 of 50 Listing Image for 35 Kau St 21 of 50 Listing Image for 35 Kau St 22 of 50 Listing Image for 35 Kau St 23 of 50 Listing Image for 35 Kau St 24 of 50 Listing Image for 35 Kau St 25 of 50 Listing Image for 35 Kau St 26 of 50 Listing Image for 35 Kau St 27 of 50 Listing Image for 35 Kau St 28 of 50 Listing Image for 35 Kau St 29 of 50 Listing Image for 35 Kau St 30 of 50 Listing Image for 35 Kau St 31 of 50 Listing Image for 35 Kau St 32 of 50 Listing Image for 35 Kau St 33 of 50 Listing Image for 35 Kau St 34 of 50 Listing Image for 35 Kau St 35 of 50 Listing Image for 35 Kau St 36 of 50 Listing Image for 35 Kau St 37 of 50 Listing Image for 35 Kau St 38 of 50 Listing Image for 35 Kau St 39 of 50 Listing Image for 35 Kau St 40 of 50 Listing Image for 35 Kau St 41 of 50 Listing Image for 35 Kau St 42 of 50 Listing Image for 35 Kau St 43 of 50 Listing Image for 35 Kau St 44 of 50 Listing Image for 35 Kau St 45 of 50 Listing Image for 35 Kau St 46 of 50 Listing Image for 35 Kau St 47 of 50 Listing Image for 35 Kau St 48 of 50 Listing Image for 35 Kau St 49 of 50 Listing Image for 35 Kau St 50 of 50

$1,475,000

↓ $105,000

Kula Kai

35 Kau St, Kula/Ulupalakua/Kanaio

5 Beds 3 Baths 1,760 SqFt Residential MLS® # 406957 Date Sold: December 26, 2025
Sold
Closed: 05/18/2026
Listing Image for 14 Kuapapa Pl 1 of 37 Listing Image for 14 Kuapapa Pl 2 of 37 Listing Image for 14 Kuapapa Pl 3 of 37 Listing Image for 14 Kuapapa Pl 4 of 37 Listing Image for 14 Kuapapa Pl 5 of 37 Listing Image for 14 Kuapapa Pl 6 of 37 Listing Image for 14 Kuapapa Pl 7 of 37 Listing Image for 14 Kuapapa Pl 8 of 37 Listing Image for 14 Kuapapa Pl 9 of 37 Listing Image for 14 Kuapapa Pl 10 of 37 Listing Image for 14 Kuapapa Pl 11 of 37 Listing Image for 14 Kuapapa Pl 12 of 37 Listing Image for 14 Kuapapa Pl 13 of 37 Listing Image for 14 Kuapapa Pl 14 of 37 Listing Image for 14 Kuapapa Pl 15 of 37 Listing Image for 14 Kuapapa Pl 16 of 37 Listing Image for 14 Kuapapa Pl 17 of 37 Listing Image for 14 Kuapapa Pl 18 of 37 Listing Image for 14 Kuapapa Pl 19 of 37 Listing Image for 14 Kuapapa Pl 20 of 37 Listing Image for 14 Kuapapa Pl 21 of 37 Listing Image for 14 Kuapapa Pl 22 of 37 Listing Image for 14 Kuapapa Pl 23 of 37 Listing Image for 14 Kuapapa Pl 24 of 37 Listing Image for 14 Kuapapa Pl 25 of 37 Listing Image for 14 Kuapapa Pl 26 of 37 Listing Image for 14 Kuapapa Pl 27 of 37 Listing Image for 14 Kuapapa Pl 28 of 37 Listing Image for 14 Kuapapa Pl 29 of 37 Listing Image for 14 Kuapapa Pl 30 of 37 Listing Image for 14 Kuapapa Pl 31 of 37 Listing Image for 14 Kuapapa Pl 32 of 37 Listing Image for 14 Kuapapa Pl 33 of 37 Listing Image for 14 Kuapapa Pl 34 of 37 Listing Image for 14 Kuapapa Pl 35 of 37 Listing Image for 14 Kuapapa Pl 36 of 37 Listing Image for 14 Kuapapa Pl 37 of 37

$755,000

↓ $243,000

Kauhale Nani Subdivision

14 Kuapapa Pl, Kihei

3 Beds 2 Baths 1,056 SqFt Residential MLS® # 407011 Date Sold: May 18, 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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