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 3254 S Kihei Rd 1 of 32 Listing Image for 3254 S Kihei Rd 2 of 32 Listing Image for 3254 S Kihei Rd 3 of 32 Listing Image for 3254 S Kihei Rd 4 of 32 Listing Image for 3254 S Kihei Rd 5 of 32 Listing Image for 3254 S Kihei Rd 6 of 32 Listing Image for 3254 S Kihei Rd 7 of 32 Listing Image for 3254 S Kihei Rd 8 of 32 Listing Image for 3254 S Kihei Rd 9 of 32 Listing Image for 3254 S Kihei Rd 10 of 32 Listing Image for 3254 S Kihei Rd 11 of 32 Listing Image for 3254 S Kihei Rd 12 of 32 Listing Image for 3254 S Kihei Rd 13 of 32 Listing Image for 3254 S Kihei Rd 14 of 32 Listing Image for 3254 S Kihei Rd 15 of 32 Listing Image for 3254 S Kihei Rd 16 of 32 Listing Image for 3254 S Kihei Rd 17 of 32 Listing Image for 3254 S Kihei Rd 18 of 32 Listing Image for 3254 S Kihei Rd 19 of 32 Listing Image for 3254 S Kihei Rd 20 of 32 Listing Image for 3254 S Kihei Rd 21 of 32 Listing Image for 3254 S Kihei Rd 22 of 32 Listing Image for 3254 S Kihei Rd 23 of 32 Listing Image for 3254 S Kihei Rd 24 of 32 Listing Image for 3254 S Kihei Rd 25 of 32 Listing Image for 3254 S Kihei Rd 26 of 32 Listing Image for 3254 S Kihei Rd 27 of 32 Listing Image for 3254 S Kihei Rd 28 of 32 Listing Image for 3254 S Kihei Rd 29 of 32 Listing Image for 3254 S Kihei Rd 30 of 32 Listing Image for 3254 S Kihei Rd 31 of 32 Listing Image for 3254 S Kihei Rd 32 of 32

$24,500,000

↓ $2,500,000

Kihei

3254 S Kihei Rd, Kihei

5 Beds 5.5 Baths 7,244 SqFt Residential MLS® # 408059

Days on Market: 279

Hawaii Life (W) Cell: 808-870-9916

Short Term Rental
Listing Image for 2777 S Kihei Rd C208 1 of 33 Listing Image for 2777 S Kihei Rd C208 2 of 33 Listing Image for 2777 S Kihei Rd C208 3 of 33 Listing Image for 2777 S Kihei Rd C208 4 of 33 Listing Image for 2777 S Kihei Rd C208 5 of 33 Listing Image for 2777 S Kihei Rd C208 6 of 33 Listing Image for 2777 S Kihei Rd C208 7 of 33 Listing Image for 2777 S Kihei Rd C208 8 of 33 Listing Image for 2777 S Kihei Rd C208 9 of 33 Listing Image for 2777 S Kihei Rd C208 10 of 33 Listing Image for 2777 S Kihei Rd C208 11 of 33 Listing Image for 2777 S Kihei Rd C208 12 of 33 Listing Image for 2777 S Kihei Rd C208 13 of 33 Listing Image for 2777 S Kihei Rd C208 14 of 33 Listing Image for 2777 S Kihei Rd C208 15 of 33 Listing Image for 2777 S Kihei Rd C208 16 of 33 Listing Image for 2777 S Kihei Rd C208 17 of 33 Listing Image for 2777 S Kihei Rd C208 18 of 33 Listing Image for 2777 S Kihei Rd C208 19 of 33 Listing Image for 2777 S Kihei Rd C208 20 of 33 Listing Image for 2777 S Kihei Rd C208 21 of 33 Listing Image for 2777 S Kihei Rd C208 22 of 33 Listing Image for 2777 S Kihei Rd C208 23 of 33 Listing Image for 2777 S Kihei Rd C208 24 of 33 Listing Image for 2777 S Kihei Rd C208 25 of 33 Listing Image for 2777 S Kihei Rd C208 26 of 33 Listing Image for 2777 S Kihei Rd C208 27 of 33 Listing Image for 2777 S Kihei Rd C208 28 of 33 Listing Image for 2777 S Kihei Rd C208 29 of 33 Listing Image for 2777 S Kihei Rd C208 30 of 33 Listing Image for 2777 S Kihei Rd C208 31 of 33 Listing Image for 2777 S Kihei Rd C208 32 of 33 Listing Image for 2777 S Kihei Rd C208 33 of 33

$999,000

↓ $137,000

Maui Kamaole C208

2777 S Kihei Rd C208, Kihei

2 Beds 2 Baths 1,052 SqFt Residential MLS® # 408046

Days on Market: 282

Coldwell Banker Island Prop(S) Cell: 808-214-7837

Listing Image for 62 Ironwood Ln 62 1 of 49 Listing Image for 62 Ironwood Ln 62 2 of 49 Listing Image for 62 Ironwood Ln 62 3 of 49 Listing Image for 62 Ironwood Ln 62 4 of 49 Listing Image for 62 Ironwood Ln 62 5 of 49 Listing Image for 62 Ironwood Ln 62 6 of 49 Listing Image for 62 Ironwood Ln 62 7 of 49 Listing Image for 62 Ironwood Ln 62 8 of 49 Listing Image for 62 Ironwood Ln 62 9 of 49 Listing Image for 62 Ironwood Ln 62 10 of 49 Listing Image for 62 Ironwood Ln 62 11 of 49 Listing Image for 62 Ironwood Ln 62 12 of 49 Listing Image for 62 Ironwood Ln 62 13 of 49 Listing Image for 62 Ironwood Ln 62 14 of 49 Listing Image for 62 Ironwood Ln 62 15 of 49 Listing Image for 62 Ironwood Ln 62 16 of 49 Listing Image for 62 Ironwood Ln 62 17 of 49 Listing Image for 62 Ironwood Ln 62 18 of 49 Listing Image for 62 Ironwood Ln 62 19 of 49 Listing Image for 62 Ironwood Ln 62 20 of 49 Listing Image for 62 Ironwood Ln 62 21 of 49 Listing Image for 62 Ironwood Ln 62 22 of 49 Listing Image for 62 Ironwood Ln 62 23 of 49 Listing Image for 62 Ironwood Ln 62 24 of 49 Listing Image for 62 Ironwood Ln 62 25 of 49 Listing Image for 62 Ironwood Ln 62 26 of 49 Listing Image for 62 Ironwood Ln 62 27 of 49 Listing Image for 62 Ironwood Ln 62 28 of 49 Listing Image for 62 Ironwood Ln 62 29 of 49 Listing Image for 62 Ironwood Ln 62 30 of 49 Listing Image for 62 Ironwood Ln 62 31 of 49 Listing Image for 62 Ironwood Ln 62 32 of 49 Listing Image for 62 Ironwood Ln 62 33 of 49 Listing Image for 62 Ironwood Ln 62 34 of 49 Listing Image for 62 Ironwood Ln 62 35 of 49 Listing Image for 62 Ironwood Ln 62 36 of 49 Listing Image for 62 Ironwood Ln 62 37 of 49 Listing Image for 62 Ironwood Ln 62 38 of 49 Listing Image for 62 Ironwood Ln 62 39 of 49 Listing Image for 62 Ironwood Ln 62 40 of 49 Listing Image for 62 Ironwood Ln 62 41 of 49 Listing Image for 62 Ironwood Ln 62 42 of 49 Listing Image for 62 Ironwood Ln 62 43 of 49 Listing Image for 62 Ironwood Ln 62 44 of 49 Listing Image for 62 Ironwood Ln 62 45 of 49 Listing Image for 62 Ironwood Ln 62 46 of 49 Listing Image for 62 Ironwood Ln 62 47 of 49 Listing Image for 62 Ironwood Ln 62 48 of 49 Listing Image for 62 Ironwood Ln 62 49 of 49

$3,550,000

↓ $100,000

Kapalua Ironwoods 62

62 Ironwood Ln 62, Kapalua

2 Beds 3 Baths 1,750 SqFt Residential MLS® # 408042

Days on Market: 281

Island Sotheby's International Realty(W) Cell: 808-269-8033

Listing Image for 223 Plantation Club Dr 14 1 of 50 Listing Image for 223 Plantation Club Dr 14 2 of 50 Listing Image for 223 Plantation Club Dr 14 3 of 50 Listing Image for 223 Plantation Club Dr 14 4 of 50 Listing Image for 223 Plantation Club Dr 14 5 of 50 Listing Image for 223 Plantation Club Dr 14 6 of 50 Listing Image for 223 Plantation Club Dr 14 7 of 50 Listing Image for 223 Plantation Club Dr 14 8 of 50 Listing Image for 223 Plantation Club Dr 14 9 of 50 Listing Image for 223 Plantation Club Dr 14 10 of 50 Listing Image for 223 Plantation Club Dr 14 11 of 50 Listing Image for 223 Plantation Club Dr 14 12 of 50 Listing Image for 223 Plantation Club Dr 14 13 of 50 Listing Image for 223 Plantation Club Dr 14 14 of 50 Listing Image for 223 Plantation Club Dr 14 15 of 50 Listing Image for 223 Plantation Club Dr 14 16 of 50 Listing Image for 223 Plantation Club Dr 14 17 of 50 Listing Image for 223 Plantation Club Dr 14 18 of 50 Listing Image for 223 Plantation Club Dr 14 19 of 50 Listing Image for 223 Plantation Club Dr 14 20 of 50 Listing Image for 223 Plantation Club Dr 14 21 of 50 Listing Image for 223 Plantation Club Dr 14 22 of 50 Listing Image for 223 Plantation Club Dr 14 23 of 50 Listing Image for 223 Plantation Club Dr 14 24 of 50 Listing Image for 223 Plantation Club Dr 14 25 of 50 Listing Image for 223 Plantation Club Dr 14 26 of 50 Listing Image for 223 Plantation Club Dr 14 27 of 50 Listing Image for 223 Plantation Club Dr 14 28 of 50 Listing Image for 223 Plantation Club Dr 14 29 of 50 Listing Image for 223 Plantation Club Dr 14 30 of 50 Listing Image for 223 Plantation Club Dr 14 31 of 50 Listing Image for 223 Plantation Club Dr 14 32 of 50 Listing Image for 223 Plantation Club Dr 14 33 of 50 Listing Image for 223 Plantation Club Dr 14 34 of 50 Listing Image for 223 Plantation Club Dr 14 35 of 50 Listing Image for 223 Plantation Club Dr 14 36 of 50 Listing Image for 223 Plantation Club Dr 14 37 of 50 Listing Image for 223 Plantation Club Dr 14 38 of 50 Listing Image for 223 Plantation Club Dr 14 39 of 50 Listing Image for 223 Plantation Club Dr 14 40 of 50 Listing Image for 223 Plantation Club Dr 14 41 of 50 Listing Image for 223 Plantation Club Dr 14 42 of 50 Listing Image for 223 Plantation Club Dr 14 43 of 50 Listing Image for 223 Plantation Club Dr 14 44 of 50 Listing Image for 223 Plantation Club Dr 14 45 of 50 Listing Image for 223 Plantation Club Dr 14 46 of 50 Listing Image for 223 Plantation Club Dr 14 47 of 50 Listing Image for 223 Plantation Club Dr 14 48 of 50 Listing Image for 223 Plantation Club Dr 14 49 of 50 Listing Image for 223 Plantation Club Dr 14 50 of 50

$9,900,000

Plantation Estates

223 Plantation Club Dr 14, Kapalua

3 Beds 3.5 Baths 5,366 SqFt Residential MLS® # 408037

Days on Market: 282

Coldwell Banker Island Prop-KP Cell: 808-344-2677

In Escrow
Listing Image for 150 Naniloa Dr 1 of 50 Listing Image for 150 Naniloa Dr 2 of 50 Listing Image for 150 Naniloa Dr 3 of 50 Listing Image for 150 Naniloa Dr 4 of 50 Listing Image for 150 Naniloa Dr 5 of 50 Listing Image for 150 Naniloa Dr 6 of 50 Listing Image for 150 Naniloa Dr 7 of 50 Listing Image for 150 Naniloa Dr 8 of 50 Listing Image for 150 Naniloa Dr 9 of 50 Listing Image for 150 Naniloa Dr 10 of 50 Listing Image for 150 Naniloa Dr 11 of 50 Listing Image for 150 Naniloa Dr 12 of 50 Listing Image for 150 Naniloa Dr 13 of 50 Listing Image for 150 Naniloa Dr 14 of 50 Listing Image for 150 Naniloa Dr 15 of 50 Listing Image for 150 Naniloa Dr 16 of 50 Listing Image for 150 Naniloa Dr 17 of 50 Listing Image for 150 Naniloa Dr 18 of 50 Listing Image for 150 Naniloa Dr 19 of 50 Listing Image for 150 Naniloa Dr 20 of 50 Listing Image for 150 Naniloa Dr 21 of 50 Listing Image for 150 Naniloa Dr 22 of 50 Listing Image for 150 Naniloa Dr 23 of 50 Listing Image for 150 Naniloa Dr 24 of 50 Listing Image for 150 Naniloa Dr 25 of 50 Listing Image for 150 Naniloa Dr 26 of 50 Listing Image for 150 Naniloa Dr 27 of 50 Listing Image for 150 Naniloa Dr 28 of 50 Listing Image for 150 Naniloa Dr 29 of 50 Listing Image for 150 Naniloa Dr 30 of 50 Listing Image for 150 Naniloa Dr 31 of 50 Listing Image for 150 Naniloa Dr 32 of 50 Listing Image for 150 Naniloa Dr 33 of 50 Listing Image for 150 Naniloa Dr 34 of 50 Listing Image for 150 Naniloa Dr 35 of 50 Listing Image for 150 Naniloa Dr 36 of 50 Listing Image for 150 Naniloa Dr 37 of 50 Listing Image for 150 Naniloa Dr 38 of 50 Listing Image for 150 Naniloa Dr 39 of 50 Listing Image for 150 Naniloa Dr 40 of 50 Listing Image for 150 Naniloa Dr 41 of 50 Listing Image for 150 Naniloa Dr 42 of 50 Listing Image for 150 Naniloa Dr 43 of 50 Listing Image for 150 Naniloa Dr 44 of 50 Listing Image for 150 Naniloa Dr 45 of 50 Listing Image for 150 Naniloa Dr 46 of 50 Listing Image for 150 Naniloa Dr 47 of 50 Listing Image for 150 Naniloa Dr 48 of 50 Listing Image for 150 Naniloa Dr 49 of 50 Listing Image for 150 Naniloa Dr 50 of 50

$1,350,000

↓ $300,000

Fleming Track

150 Naniloa Dr, Wailuku

3 Beds 2 Baths 2,548 SqFt Residential MLS® # 408036

Days on Market: 282

Sunward Realty Inc

Listing Image for 391 Haniu St Lot 6a 1 of 13 Listing Image for 391 Haniu St Lot 6a 2 of 13 Listing Image for 391 Haniu St Lot 6a 3 of 13 Listing Image for 391 Haniu St Lot 6a 4 of 13 Listing Image for 391 Haniu St Lot 6a 5 of 13 Listing Image for 391 Haniu St Lot 6a 6 of 13 Listing Image for 391 Haniu St Lot 6a 7 of 13 Listing Image for 391 Haniu St Lot 6a 8 of 13 Listing Image for 391 Haniu St Lot 6a 9 of 13 Listing Image for 391 Haniu St Lot 6a 10 of 13 Listing Image for 391 Haniu St Lot 6a 11 of 13 Listing Image for 391 Haniu St Lot 6a 12 of 13 Listing Image for 391 Haniu St Lot 6a 13 of 13

$8,395,000

Makila Ranches

391 Haniu St Lot 6a, Lahaina

5 Beds 4 Baths 4,591 SqFt Residential MLS® # 408032

Days on Market: 282

Welcome Hawaii Properties Cell: 808-280-2480

Short Term Rental
Listing Image for 2737 S Kihei Rd 336 1 of 38 Listing Image for 2737 S Kihei Rd 336 2 of 38 Listing Image for 2737 S Kihei Rd 336 3 of 38 Listing Image for 2737 S Kihei Rd 336 4 of 38 Listing Image for 2737 S Kihei Rd 336 5 of 38 Listing Image for 2737 S Kihei Rd 336 6 of 38 Listing Image for 2737 S Kihei Rd 336 7 of 38 Listing Image for 2737 S Kihei Rd 336 8 of 38 Listing Image for 2737 S Kihei Rd 336 9 of 38 Listing Image for 2737 S Kihei Rd 336 10 of 38 Listing Image for 2737 S Kihei Rd 336 11 of 38 Listing Image for 2737 S Kihei Rd 336 12 of 38 Listing Image for 2737 S Kihei Rd 336 13 of 38 Listing Image for 2737 S Kihei Rd 336 14 of 38 Listing Image for 2737 S Kihei Rd 336 15 of 38 Listing Image for 2737 S Kihei Rd 336 16 of 38 Listing Image for 2737 S Kihei Rd 336 17 of 38 Listing Image for 2737 S Kihei Rd 336 18 of 38 Listing Image for 2737 S Kihei Rd 336 19 of 38 Listing Image for 2737 S Kihei Rd 336 20 of 38 Listing Image for 2737 S Kihei Rd 336 21 of 38 Listing Image for 2737 S Kihei Rd 336 22 of 38 Listing Image for 2737 S Kihei Rd 336 23 of 38 Listing Image for 2737 S Kihei Rd 336 24 of 38 Listing Image for 2737 S Kihei Rd 336 25 of 38 Listing Image for 2737 S Kihei Rd 336 26 of 38 Listing Image for 2737 S Kihei Rd 336 27 of 38 Listing Image for 2737 S Kihei Rd 336 28 of 38 Listing Image for 2737 S Kihei Rd 336 29 of 38 Listing Image for 2737 S Kihei Rd 336 30 of 38 Listing Image for 2737 S Kihei Rd 336 31 of 38 Listing Image for 2737 S Kihei Rd 336 32 of 38 Listing Image for 2737 S Kihei Rd 336 33 of 38 Listing Image for 2737 S Kihei Rd 336 34 of 38 Listing Image for 2737 S Kihei Rd 336 35 of 38 Listing Image for 2737 S Kihei Rd 336 36 of 38 Listing Image for 2737 S Kihei Rd 336 37 of 38 Listing Image for 2737 S Kihei Rd 336 38 of 38

$850,000

↓ $45,000

Hale Kamaole 336

2737 S Kihei Rd 336, Kihei

2 Beds 2 Baths 1,112 SqFt Residential MLS® # 408020

Days on Market: 284

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

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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: 03/06/2026
Listing Image for 1097 Ewa Pl 1 of 41 Listing Image for 1097 Ewa Pl 2 of 41 Listing Image for 1097 Ewa Pl 3 of 41 Listing Image for 1097 Ewa Pl 4 of 41 Listing Image for 1097 Ewa Pl 5 of 41 Listing Image for 1097 Ewa Pl 6 of 41 Listing Image for 1097 Ewa Pl 7 of 41 Listing Image for 1097 Ewa Pl 8 of 41 Listing Image for 1097 Ewa Pl 9 of 41 Listing Image for 1097 Ewa Pl 10 of 41 Listing Image for 1097 Ewa Pl 11 of 41 Listing Image for 1097 Ewa Pl 12 of 41 Listing Image for 1097 Ewa Pl 13 of 41 Listing Image for 1097 Ewa Pl 14 of 41 Listing Image for 1097 Ewa Pl 15 of 41 Listing Image for 1097 Ewa Pl 16 of 41 Listing Image for 1097 Ewa Pl 17 of 41 Listing Image for 1097 Ewa Pl 18 of 41 Listing Image for 1097 Ewa Pl 19 of 41 Listing Image for 1097 Ewa Pl 20 of 41 Listing Image for 1097 Ewa Pl 21 of 41 Listing Image for 1097 Ewa Pl 22 of 41 Listing Image for 1097 Ewa Pl 23 of 41 Listing Image for 1097 Ewa Pl 24 of 41 Listing Image for 1097 Ewa Pl 25 of 41 Listing Image for 1097 Ewa Pl 26 of 41 Listing Image for 1097 Ewa Pl 27 of 41 Listing Image for 1097 Ewa Pl 28 of 41 Listing Image for 1097 Ewa Pl 29 of 41 Listing Image for 1097 Ewa Pl 30 of 41 Listing Image for 1097 Ewa Pl 31 of 41 Listing Image for 1097 Ewa Pl 32 of 41 Listing Image for 1097 Ewa Pl 33 of 41 Listing Image for 1097 Ewa Pl 34 of 41 Listing Image for 1097 Ewa Pl 35 of 41 Listing Image for 1097 Ewa Pl 36 of 41 Listing Image for 1097 Ewa Pl 37 of 41 Listing Image for 1097 Ewa Pl 38 of 41 Listing Image for 1097 Ewa Pl 39 of 41 Listing Image for 1097 Ewa Pl 40 of 41 Listing Image for 1097 Ewa Pl 41 of 41

$1,175,000

↓ $320,000

Waiohuli-Keokea Beach

1097 Ewa Pl, Kihei

2 Beds 2 Baths 1,558 SqFt Residential MLS® # 407315 Date Sold: March 6, 2026
Sold
Closed: 08/07/2026
Listing Image for 50 Puu Anoano St 3405 1 of 50 Listing Image for 50 Puu Anoano St 3405 2 of 50 Listing Image for 50 Puu Anoano St 3405 3 of 50 Listing Image for 50 Puu Anoano St 3405 4 of 50 Listing Image for 50 Puu Anoano St 3405 5 of 50 Listing Image for 50 Puu Anoano St 3405 6 of 50 Listing Image for 50 Puu Anoano St 3405 7 of 50 Listing Image for 50 Puu Anoano St 3405 8 of 50 Listing Image for 50 Puu Anoano St 3405 9 of 50 Listing Image for 50 Puu Anoano St 3405 10 of 50 Listing Image for 50 Puu Anoano St 3405 11 of 50 Listing Image for 50 Puu Anoano St 3405 12 of 50 Listing Image for 50 Puu Anoano St 3405 13 of 50 Listing Image for 50 Puu Anoano St 3405 14 of 50 Listing Image for 50 Puu Anoano St 3405 15 of 50 Listing Image for 50 Puu Anoano St 3405 16 of 50 Listing Image for 50 Puu Anoano St 3405 17 of 50 Listing Image for 50 Puu Anoano St 3405 18 of 50 Listing Image for 50 Puu Anoano St 3405 19 of 50 Listing Image for 50 Puu Anoano St 3405 20 of 50 Listing Image for 50 Puu Anoano St 3405 21 of 50 Listing Image for 50 Puu Anoano St 3405 22 of 50 Listing Image for 50 Puu Anoano St 3405 23 of 50 Listing Image for 50 Puu Anoano St 3405 24 of 50 Listing Image for 50 Puu Anoano St 3405 25 of 50 Listing Image for 50 Puu Anoano St 3405 26 of 50 Listing Image for 50 Puu Anoano St 3405 27 of 50 Listing Image for 50 Puu Anoano St 3405 28 of 50 Listing Image for 50 Puu Anoano St 3405 29 of 50 Listing Image for 50 Puu Anoano St 3405 30 of 50 Listing Image for 50 Puu Anoano St 3405 31 of 50 Listing Image for 50 Puu Anoano St 3405 32 of 50 Listing Image for 50 Puu Anoano St 3405 33 of 50 Listing Image for 50 Puu Anoano St 3405 34 of 50 Listing Image for 50 Puu Anoano St 3405 35 of 50 Listing Image for 50 Puu Anoano St 3405 36 of 50 Listing Image for 50 Puu Anoano St 3405 37 of 50 Listing Image for 50 Puu Anoano St 3405 38 of 50 Listing Image for 50 Puu Anoano St 3405 39 of 50 Listing Image for 50 Puu Anoano St 3405 40 of 50 Listing Image for 50 Puu Anoano St 3405 41 of 50 Listing Image for 50 Puu Anoano St 3405 42 of 50 Listing Image for 50 Puu Anoano St 3405 43 of 50 Listing Image for 50 Puu Anoano St 3405 44 of 50 Listing Image for 50 Puu Anoano St 3405 45 of 50 Listing Image for 50 Puu Anoano St 3405 46 of 50 Listing Image for 50 Puu Anoano St 3405 47 of 50 Listing Image for 50 Puu Anoano St 3405 48 of 50 Listing Image for 50 Puu Anoano St 3405 49 of 50 Listing Image for 50 Puu Anoano St 3405 50 of 50

$760,000

↓ $90,000

Masters 3405

50 Puu Anoano St 3405, Kaanapali

1 Bed 1 Bath 901 SqFt Residential MLS® # 407311 Date Sold: August 7, 2026
Sold
Closed: 12/19/2025
Listing Image for 408 Copp Rd 1 of 41 Listing Image for 408 Copp Rd 2 of 41 Listing Image for 408 Copp Rd 3 of 41 Listing Image for 408 Copp Rd 4 of 41 Listing Image for 408 Copp Rd 5 of 41 Listing Image for 408 Copp Rd 6 of 41 Listing Image for 408 Copp Rd 7 of 41 Listing Image for 408 Copp Rd 8 of 41 Listing Image for 408 Copp Rd 9 of 41 Listing Image for 408 Copp Rd 10 of 41 Listing Image for 408 Copp Rd 11 of 41 Listing Image for 408 Copp Rd 12 of 41 Listing Image for 408 Copp Rd 13 of 41 Listing Image for 408 Copp Rd 14 of 41 Listing Image for 408 Copp Rd 15 of 41 Listing Image for 408 Copp Rd 16 of 41 Listing Image for 408 Copp Rd 17 of 41 Listing Image for 408 Copp Rd 18 of 41 Listing Image for 408 Copp Rd 19 of 41 Listing Image for 408 Copp Rd 20 of 41 Listing Image for 408 Copp Rd 21 of 41 Listing Image for 408 Copp Rd 22 of 41 Listing Image for 408 Copp Rd 23 of 41 Listing Image for 408 Copp Rd 24 of 41 Listing Image for 408 Copp Rd 25 of 41 Listing Image for 408 Copp Rd 26 of 41 Listing Image for 408 Copp Rd 27 of 41 Listing Image for 408 Copp Rd 28 of 41 Listing Image for 408 Copp Rd 29 of 41 Listing Image for 408 Copp Rd 30 of 41 Listing Image for 408 Copp Rd 31 of 41 Listing Image for 408 Copp Rd 32 of 41 Listing Image for 408 Copp Rd 33 of 41 Listing Image for 408 Copp Rd 34 of 41 Listing Image for 408 Copp Rd 35 of 41 Listing Image for 408 Copp Rd 36 of 41 Listing Image for 408 Copp Rd 37 of 41 Listing Image for 408 Copp Rd 38 of 41 Listing Image for 408 Copp Rd 39 of 41 Listing Image for 408 Copp Rd 40 of 41 Listing Image for 408 Copp Rd 41 of 41

$1,475,000

Kula/Ulupalakua/Kanaio

408 Copp Rd, Kula/Ulupalakua/Kanaio

4 Beds 2 Baths 1,644 SqFt Residential MLS® # 407298 Date Sold: December 19, 2025
Sold
Closed: 10/02/2025
Listing Image for 2533 Poko Pl 1 of 3 Listing Image for 2533 Poko Pl 2 of 3 Listing Image for 2533 Poko Pl 3 of 3

$1,625,000

Haiku

2533 Poko Pl, Haiku

1 Bed 1 Bath 2,145 SqFt Residential MLS® # 407296 Date Sold: October 2, 2025
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: 12/26/2025
Listing Image for 5157 Lower Honoapiilani Rd 1 of 42 Listing Image for 5157 Lower Honoapiilani Rd 2 of 42 Listing Image for 5157 Lower Honoapiilani Rd 3 of 42 Listing Image for 5157 Lower Honoapiilani Rd 4 of 42 Listing Image for 5157 Lower Honoapiilani Rd 5 of 42 Listing Image for 5157 Lower Honoapiilani Rd 6 of 42 Listing Image for 5157 Lower Honoapiilani Rd 7 of 42 Listing Image for 5157 Lower Honoapiilani Rd 8 of 42 Listing Image for 5157 Lower Honoapiilani Rd 9 of 42 Listing Image for 5157 Lower Honoapiilani Rd 10 of 42 Listing Image for 5157 Lower Honoapiilani Rd 11 of 42 Listing Image for 5157 Lower Honoapiilani Rd 12 of 42 Listing Image for 5157 Lower Honoapiilani Rd 13 of 42 Listing Image for 5157 Lower Honoapiilani Rd 14 of 42 Listing Image for 5157 Lower Honoapiilani Rd 15 of 42 Listing Image for 5157 Lower Honoapiilani Rd 16 of 42 Listing Image for 5157 Lower Honoapiilani Rd 17 of 42 Listing Image for 5157 Lower Honoapiilani Rd 18 of 42 Listing Image for 5157 Lower Honoapiilani Rd 19 of 42 Listing Image for 5157 Lower Honoapiilani Rd 20 of 42 Listing Image for 5157 Lower Honoapiilani Rd 21 of 42 Listing Image for 5157 Lower Honoapiilani Rd 22 of 42 Listing Image for 5157 Lower Honoapiilani Rd 23 of 42 Listing Image for 5157 Lower Honoapiilani Rd 24 of 42 Listing Image for 5157 Lower Honoapiilani Rd 25 of 42 Listing Image for 5157 Lower Honoapiilani Rd 26 of 42 Listing Image for 5157 Lower Honoapiilani Rd 27 of 42 Listing Image for 5157 Lower Honoapiilani Rd 28 of 42 Listing Image for 5157 Lower Honoapiilani Rd 29 of 42 Listing Image for 5157 Lower Honoapiilani Rd 30 of 42 Listing Image for 5157 Lower Honoapiilani Rd 31 of 42 Listing Image for 5157 Lower Honoapiilani Rd 32 of 42 Listing Image for 5157 Lower Honoapiilani Rd 33 of 42 Listing Image for 5157 Lower Honoapiilani Rd 34 of 42 Listing Image for 5157 Lower Honoapiilani Rd 35 of 42 Listing Image for 5157 Lower Honoapiilani Rd 36 of 42 Listing Image for 5157 Lower Honoapiilani Rd 37 of 42 Listing Image for 5157 Lower Honoapiilani Rd 38 of 42 Listing Image for 5157 Lower Honoapiilani Rd 39 of 42 Listing Image for 5157 Lower Honoapiilani Rd 40 of 42 Listing Image for 5157 Lower Honoapiilani Rd 41 of 42 Listing Image for 5157 Lower Honoapiilani Rd 42 of 42

$3,707,200

↑ $1,468,312

Napili/Kahana/Honokowai

5157 Lower Honoapiilani Rd, Napili/Kahana/Honokowai

2 Beds 2 Baths 2,348 SqFt Residential MLS® # 407292 Date Sold: December 26, 2025
Sold
Closed: 10/01/2025
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$1,452,000

Kula/Ulupalakua/Kanaio

44 Kulamanu Cir, Kula/Ulupalakua/Kanaio

3 Beds 2 Baths 1,920 SqFt Residential MLS® # 407285 Date Sold: October 1, 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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