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 145 N Kihei Rd 326 1 of 35 Listing Image for 145 N Kihei Rd 326 2 of 35 Listing Image for 145 N Kihei Rd 326 3 of 35 Listing Image for 145 N Kihei Rd 326 4 of 35 Listing Image for 145 N Kihei Rd 326 5 of 35 Listing Image for 145 N Kihei Rd 326 6 of 35 Listing Image for 145 N Kihei Rd 326 7 of 35 Listing Image for 145 N Kihei Rd 326 8 of 35 Listing Image for 145 N Kihei Rd 326 9 of 35 Listing Image for 145 N Kihei Rd 326 10 of 35 Listing Image for 145 N Kihei Rd 326 11 of 35 Listing Image for 145 N Kihei Rd 326 12 of 35 Listing Image for 145 N Kihei Rd 326 13 of 35 Listing Image for 145 N Kihei Rd 326 14 of 35 Listing Image for 145 N Kihei Rd 326 15 of 35 Listing Image for 145 N Kihei Rd 326 16 of 35 Listing Image for 145 N Kihei Rd 326 17 of 35 Listing Image for 145 N Kihei Rd 326 18 of 35 Listing Image for 145 N Kihei Rd 326 19 of 35 Listing Image for 145 N Kihei Rd 326 20 of 35 Listing Image for 145 N Kihei Rd 326 21 of 35 Listing Image for 145 N Kihei Rd 326 22 of 35 Listing Image for 145 N Kihei Rd 326 23 of 35 Listing Image for 145 N Kihei Rd 326 24 of 35 Listing Image for 145 N Kihei Rd 326 25 of 35 Listing Image for 145 N Kihei Rd 326 26 of 35 Listing Image for 145 N Kihei Rd 326 27 of 35 Listing Image for 145 N Kihei Rd 326 28 of 35 Listing Image for 145 N Kihei Rd 326 29 of 35 Listing Image for 145 N Kihei Rd 326 30 of 35 Listing Image for 145 N Kihei Rd 326 31 of 35 Listing Image for 145 N Kihei Rd 326 32 of 35 Listing Image for 145 N Kihei Rd 326 33 of 35 Listing Image for 145 N Kihei Rd 326 34 of 35 Listing Image for 145 N Kihei Rd 326 35 of 35

$899,000

↓ $26,000

Sugar Beach Resort 326

145 N Kihei Rd 326, Kihei

1 Bed 1 Bath 613 SqFt Residential MLS® # 408164

Days on Market: 272

Coldwell Banker Island Prop(S) Cell: 808-446-5350

Listing Image for 107 Unahe Pl Lot 130-a 1 of 49 Listing Image for 107 Unahe Pl Lot 130-a 2 of 49 Listing Image for 107 Unahe Pl Lot 130-a 3 of 49 Listing Image for 107 Unahe Pl Lot 130-a 4 of 49 Listing Image for 107 Unahe Pl Lot 130-a 5 of 49 Listing Image for 107 Unahe Pl Lot 130-a 6 of 49 Listing Image for 107 Unahe Pl Lot 130-a 7 of 49 Listing Image for 107 Unahe Pl Lot 130-a 8 of 49 Listing Image for 107 Unahe Pl Lot 130-a 9 of 49 Listing Image for 107 Unahe Pl Lot 130-a 10 of 49 Listing Image for 107 Unahe Pl Lot 130-a 11 of 49 Listing Image for 107 Unahe Pl Lot 130-a 12 of 49 Listing Image for 107 Unahe Pl Lot 130-a 13 of 49 Listing Image for 107 Unahe Pl Lot 130-a 14 of 49 Listing Image for 107 Unahe Pl Lot 130-a 15 of 49 Listing Image for 107 Unahe Pl Lot 130-a 16 of 49 Listing Image for 107 Unahe Pl Lot 130-a 17 of 49 Listing Image for 107 Unahe Pl Lot 130-a 18 of 49 Listing Image for 107 Unahe Pl Lot 130-a 19 of 49 Listing Image for 107 Unahe Pl Lot 130-a 20 of 49 Listing Image for 107 Unahe Pl Lot 130-a 21 of 49 Listing Image for 107 Unahe Pl Lot 130-a 22 of 49 Listing Image for 107 Unahe Pl Lot 130-a 23 of 49 Listing Image for 107 Unahe Pl Lot 130-a 24 of 49 Listing Image for 107 Unahe Pl Lot 130-a 25 of 49 Listing Image for 107 Unahe Pl Lot 130-a 26 of 49 Listing Image for 107 Unahe Pl Lot 130-a 27 of 49 Listing Image for 107 Unahe Pl Lot 130-a 28 of 49 Listing Image for 107 Unahe Pl Lot 130-a 29 of 49 Listing Image for 107 Unahe Pl Lot 130-a 30 of 49 Listing Image for 107 Unahe Pl Lot 130-a 31 of 49 Listing Image for 107 Unahe Pl Lot 130-a 32 of 49 Listing Image for 107 Unahe Pl Lot 130-a 33 of 49 Listing Image for 107 Unahe Pl Lot 130-a 34 of 49 Listing Image for 107 Unahe Pl Lot 130-a 35 of 49 Listing Image for 107 Unahe Pl Lot 130-a 36 of 49 Listing Image for 107 Unahe Pl Lot 130-a 37 of 49 Listing Image for 107 Unahe Pl Lot 130-a 38 of 49 Listing Image for 107 Unahe Pl Lot 130-a 39 of 49 Listing Image for 107 Unahe Pl Lot 130-a 40 of 49 Listing Image for 107 Unahe Pl Lot 130-a 41 of 49 Listing Image for 107 Unahe Pl Lot 130-a 42 of 49 Listing Image for 107 Unahe Pl Lot 130-a 43 of 49 Listing Image for 107 Unahe Pl Lot 130-a 44 of 49 Listing Image for 107 Unahe Pl Lot 130-a 45 of 49 Listing Image for 107 Unahe Pl Lot 130-a 46 of 49 Listing Image for 107 Unahe Pl Lot 130-a 47 of 49 Listing Image for 107 Unahe Pl Lot 130-a 48 of 49 Listing Image for 107 Unahe Pl Lot 130-a 49 of 49

$1,443,325

↓ $50,000

The Parkways at Maui Lani

107 Unahe Pl Lot 130-a, Kahului

4 Beds 3 Baths 2,474 SqFt Residential MLS® # 408156

Days on Market: 273

Towne Island Homes, Ltd

In Escrow
Listing Image for 65 Wili Okai Way 1 of 50 Listing Image for 65 Wili Okai Way 2 of 50 Listing Image for 65 Wili Okai Way 3 of 50 Listing Image for 65 Wili Okai Way 4 of 50 Listing Image for 65 Wili Okai Way 5 of 50 Listing Image for 65 Wili Okai Way 6 of 50 Listing Image for 65 Wili Okai Way 7 of 50 Listing Image for 65 Wili Okai Way 8 of 50 Listing Image for 65 Wili Okai Way 9 of 50 Listing Image for 65 Wili Okai Way 10 of 50 Listing Image for 65 Wili Okai Way 11 of 50 Listing Image for 65 Wili Okai Way 12 of 50 Listing Image for 65 Wili Okai Way 13 of 50 Listing Image for 65 Wili Okai Way 14 of 50 Listing Image for 65 Wili Okai Way 15 of 50 Listing Image for 65 Wili Okai Way 16 of 50 Listing Image for 65 Wili Okai Way 17 of 50 Listing Image for 65 Wili Okai Way 18 of 50 Listing Image for 65 Wili Okai Way 19 of 50 Listing Image for 65 Wili Okai Way 20 of 50 Listing Image for 65 Wili Okai Way 21 of 50 Listing Image for 65 Wili Okai Way 22 of 50 Listing Image for 65 Wili Okai Way 23 of 50 Listing Image for 65 Wili Okai Way 24 of 50 Listing Image for 65 Wili Okai Way 25 of 50 Listing Image for 65 Wili Okai Way 26 of 50 Listing Image for 65 Wili Okai Way 27 of 50 Listing Image for 65 Wili Okai Way 28 of 50 Listing Image for 65 Wili Okai Way 29 of 50 Listing Image for 65 Wili Okai Way 30 of 50 Listing Image for 65 Wili Okai Way 31 of 50 Listing Image for 65 Wili Okai Way 32 of 50 Listing Image for 65 Wili Okai Way 33 of 50 Listing Image for 65 Wili Okai Way 34 of 50 Listing Image for 65 Wili Okai Way 35 of 50 Listing Image for 65 Wili Okai Way 36 of 50 Listing Image for 65 Wili Okai Way 37 of 50 Listing Image for 65 Wili Okai Way 38 of 50 Listing Image for 65 Wili Okai Way 39 of 50 Listing Image for 65 Wili Okai Way 40 of 50 Listing Image for 65 Wili Okai Way 41 of 50 Listing Image for 65 Wili Okai Way 42 of 50 Listing Image for 65 Wili Okai Way 43 of 50 Listing Image for 65 Wili Okai Way 44 of 50 Listing Image for 65 Wili Okai Way 45 of 50 Listing Image for 65 Wili Okai Way 46 of 50 Listing Image for 65 Wili Okai Way 47 of 50 Listing Image for 65 Wili Okai Way 48 of 50 Listing Image for 65 Wili Okai Way 49 of 50 Listing Image for 65 Wili Okai Way 50 of 50

$6,000,000

↓ $3,500,000

Puunoa

65 Wili Okai Way, Lahaina

5 Beds 5.5 Baths 5,777 SqFt Residential MLS® # 408146

Days on Market: 273

Compass Cell: 808-283-7214

Short Term Rental
Listing Image for 150 Hauoli St 502 1 of 34 Listing Image for 150 Hauoli St 502 2 of 34 Listing Image for 150 Hauoli St 502 3 of 34 Listing Image for 150 Hauoli St 502 4 of 34 Listing Image for 150 Hauoli St 502 5 of 34 Listing Image for 150 Hauoli St 502 6 of 34 Listing Image for 150 Hauoli St 502 7 of 34 Listing Image for 150 Hauoli St 502 8 of 34 Listing Image for 150 Hauoli St 502 9 of 34 Listing Image for 150 Hauoli St 502 10 of 34 Listing Image for 150 Hauoli St 502 11 of 34 Listing Image for 150 Hauoli St 502 12 of 34 Listing Image for 150 Hauoli St 502 13 of 34 Listing Image for 150 Hauoli St 502 14 of 34 Listing Image for 150 Hauoli St 502 15 of 34 Listing Image for 150 Hauoli St 502 16 of 34 Listing Image for 150 Hauoli St 502 17 of 34 Listing Image for 150 Hauoli St 502 18 of 34 Listing Image for 150 Hauoli St 502 19 of 34 Listing Image for 150 Hauoli St 502 20 of 34 Listing Image for 150 Hauoli St 502 21 of 34 Listing Image for 150 Hauoli St 502 22 of 34 Listing Image for 150 Hauoli St 502 23 of 34 Listing Image for 150 Hauoli St 502 24 of 34 Listing Image for 150 Hauoli St 502 25 of 34 Listing Image for 150 Hauoli St 502 26 of 34 Listing Image for 150 Hauoli St 502 27 of 34 Listing Image for 150 Hauoli St 502 28 of 34 Listing Image for 150 Hauoli St 502 29 of 34 Listing Image for 150 Hauoli St 502 30 of 34 Listing Image for 150 Hauoli St 502 31 of 34 Listing Image for 150 Hauoli St 502 32 of 34 Listing Image for 150 Hauoli St 502 33 of 34 Listing Image for 150 Hauoli St 502 34 of 34

$875,000

↓ $24,000

Island Sands 502

150 Hauoli St 502, Maalaea

2 Beds 2 Baths 899 SqFt Residential MLS® # 408140

Days on Market: 274

Hawaii Life (W) Cell: 808-870-8668

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
Listing Image for 500 Umeke St 47 1 of 46 Listing Image for 500 Umeke St 47 2 of 46 Listing Image for 500 Umeke St 47 3 of 46 Listing Image for 500 Umeke St 47 4 of 46 Listing Image for 500 Umeke St 47 5 of 46 Listing Image for 500 Umeke St 47 6 of 46 Listing Image for 500 Umeke St 47 7 of 46 Listing Image for 500 Umeke St 47 8 of 46 Listing Image for 500 Umeke St 47 9 of 46 Listing Image for 500 Umeke St 47 10 of 46 Listing Image for 500 Umeke St 47 11 of 46 Listing Image for 500 Umeke St 47 12 of 46 Listing Image for 500 Umeke St 47 13 of 46 Listing Image for 500 Umeke St 47 14 of 46 Listing Image for 500 Umeke St 47 15 of 46 Listing Image for 500 Umeke St 47 16 of 46 Listing Image for 500 Umeke St 47 17 of 46 Listing Image for 500 Umeke St 47 18 of 46 Listing Image for 500 Umeke St 47 19 of 46 Listing Image for 500 Umeke St 47 20 of 46 Listing Image for 500 Umeke St 47 21 of 46 Listing Image for 500 Umeke St 47 22 of 46 Listing Image for 500 Umeke St 47 23 of 46 Listing Image for 500 Umeke St 47 24 of 46 Listing Image for 500 Umeke St 47 25 of 46 Listing Image for 500 Umeke St 47 26 of 46 Listing Image for 500 Umeke St 47 27 of 46 Listing Image for 500 Umeke St 47 28 of 46 Listing Image for 500 Umeke St 47 29 of 46 Listing Image for 500 Umeke St 47 30 of 46 Listing Image for 500 Umeke St 47 31 of 46 Listing Image for 500 Umeke St 47 32 of 46 Listing Image for 500 Umeke St 47 33 of 46 Listing Image for 500 Umeke St 47 34 of 46 Listing Image for 500 Umeke St 47 35 of 46 Listing Image for 500 Umeke St 47 36 of 46 Listing Image for 500 Umeke St 47 37 of 46 Listing Image for 500 Umeke St 47 38 of 46 Listing Image for 500 Umeke St 47 39 of 46 Listing Image for 500 Umeke St 47 40 of 46 Listing Image for 500 Umeke St 47 41 of 46 Listing Image for 500 Umeke St 47 42 of 46 Listing Image for 500 Umeke St 47 43 of 46 Listing Image for 500 Umeke St 47 44 of 46 Listing Image for 500 Umeke St 47 45 of 46 Listing Image for 500 Umeke St 47 46 of 46

$1,950,000

↓ $100,000

Hokulani Golf Villas 47

500 Umeke St 47, Kihei

3 Beds 2.5 Baths 2,450 SqFt Residential MLS® # 408135

Days on Market: 274

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

Listing Image for 2560 Kekaa Dr F202 1 of 34 Listing Image for 2560 Kekaa Dr F202 2 of 34 Listing Image for 2560 Kekaa Dr F202 3 of 34 Listing Image for 2560 Kekaa Dr F202 4 of 34 Listing Image for 2560 Kekaa Dr F202 5 of 34 Listing Image for 2560 Kekaa Dr F202 6 of 34 Listing Image for 2560 Kekaa Dr F202 7 of 34 Listing Image for 2560 Kekaa Dr F202 8 of 34 Listing Image for 2560 Kekaa Dr F202 9 of 34 Listing Image for 2560 Kekaa Dr F202 10 of 34 Listing Image for 2560 Kekaa Dr F202 11 of 34 Listing Image for 2560 Kekaa Dr F202 12 of 34 Listing Image for 2560 Kekaa Dr F202 13 of 34 Listing Image for 2560 Kekaa Dr F202 14 of 34 Listing Image for 2560 Kekaa Dr F202 15 of 34 Listing Image for 2560 Kekaa Dr F202 16 of 34 Listing Image for 2560 Kekaa Dr F202 17 of 34 Listing Image for 2560 Kekaa Dr F202 18 of 34 Listing Image for 2560 Kekaa Dr F202 19 of 34 Listing Image for 2560 Kekaa Dr F202 20 of 34 Listing Image for 2560 Kekaa Dr F202 21 of 34 Listing Image for 2560 Kekaa Dr F202 22 of 34 Listing Image for 2560 Kekaa Dr F202 23 of 34 Listing Image for 2560 Kekaa Dr F202 24 of 34 Listing Image for 2560 Kekaa Dr F202 25 of 34 Listing Image for 2560 Kekaa Dr F202 26 of 34 Listing Image for 2560 Kekaa Dr F202 27 of 34 Listing Image for 2560 Kekaa Dr F202 28 of 34 Listing Image for 2560 Kekaa Dr F202 29 of 34 Listing Image for 2560 Kekaa Dr F202 30 of 34 Listing Image for 2560 Kekaa Dr F202 31 of 34 Listing Image for 2560 Kekaa Dr F202 32 of 34 Listing Image for 2560 Kekaa Dr F202 33 of 34 Listing Image for 2560 Kekaa Dr F202 34 of 34

$1,325,000

↑ $80,000

Kaanapali Royal F202

2560 Kekaa Dr F202, Kaanapali

2 Beds 2 Baths 1,534 SqFt Residential MLS® # 408131

Days on Market: 275

Berkshire Hathaway Maui Prop-L

In Escrow Short Term Rental
Listing Image for 500 Kapalua Dr 23p7-8 1 of 47 Listing Image for 500 Kapalua Dr 23p7-8 2 of 47 Listing Image for 500 Kapalua Dr 23p7-8 3 of 47 Listing Image for 500 Kapalua Dr 23p7-8 4 of 47 Listing Image for 500 Kapalua Dr 23p7-8 5 of 47 Listing Image for 500 Kapalua Dr 23p7-8 6 of 47 Listing Image for 500 Kapalua Dr 23p7-8 7 of 47 Listing Image for 500 Kapalua Dr 23p7-8 8 of 47 Listing Image for 500 Kapalua Dr 23p7-8 9 of 47 Listing Image for 500 Kapalua Dr 23p7-8 10 of 47 Listing Image for 500 Kapalua Dr 23p7-8 11 of 47 Listing Image for 500 Kapalua Dr 23p7-8 12 of 47 Listing Image for 500 Kapalua Dr 23p7-8 13 of 47 Listing Image for 500 Kapalua Dr 23p7-8 14 of 47 Listing Image for 500 Kapalua Dr 23p7-8 15 of 47 Listing Image for 500 Kapalua Dr 23p7-8 16 of 47 Listing Image for 500 Kapalua Dr 23p7-8 17 of 47 Listing Image for 500 Kapalua Dr 23p7-8 18 of 47 Listing Image for 500 Kapalua Dr 23p7-8 19 of 47 Listing Image for 500 Kapalua Dr 23p7-8 20 of 47 Listing Image for 500 Kapalua Dr 23p7-8 21 of 47 Listing Image for 500 Kapalua Dr 23p7-8 22 of 47 Listing Image for 500 Kapalua Dr 23p7-8 23 of 47 Listing Image for 500 Kapalua Dr 23p7-8 24 of 47 Listing Image for 500 Kapalua Dr 23p7-8 25 of 47 Listing Image for 500 Kapalua Dr 23p7-8 26 of 47 Listing Image for 500 Kapalua Dr 23p7-8 27 of 47 Listing Image for 500 Kapalua Dr 23p7-8 28 of 47 Listing Image for 500 Kapalua Dr 23p7-8 29 of 47 Listing Image for 500 Kapalua Dr 23p7-8 30 of 47 Listing Image for 500 Kapalua Dr 23p7-8 31 of 47 Listing Image for 500 Kapalua Dr 23p7-8 32 of 47 Listing Image for 500 Kapalua Dr 23p7-8 33 of 47 Listing Image for 500 Kapalua Dr 23p7-8 34 of 47 Listing Image for 500 Kapalua Dr 23p7-8 35 of 47 Listing Image for 500 Kapalua Dr 23p7-8 36 of 47 Listing Image for 500 Kapalua Dr 23p7-8 37 of 47 Listing Image for 500 Kapalua Dr 23p7-8 38 of 47 Listing Image for 500 Kapalua Dr 23p7-8 39 of 47 Listing Image for 500 Kapalua Dr 23p7-8 40 of 47 Listing Image for 500 Kapalua Dr 23p7-8 41 of 47 Listing Image for 500 Kapalua Dr 23p7-8 42 of 47 Listing Image for 500 Kapalua Dr 23p7-8 43 of 47 Listing Image for 500 Kapalua Dr 23p7-8 44 of 47 Listing Image for 500 Kapalua Dr 23p7-8 45 of 47 Listing Image for 500 Kapalua Dr 23p7-8 46 of 47 Listing Image for 500 Kapalua Dr 23p7-8 47 of 47

$1,539,000

↑ $100,000

Kapalua Golf Villas 23P7-8

500 Kapalua Dr 23p7-8, Kapalua

2 Beds 2 Baths 1,344 SqFt Residential MLS® # 408122

Days on Market: 275

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

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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: 05/11/2026
Listing Image for 202 Nakoa Dr 1 of 21 Listing Image for 202 Nakoa Dr 2 of 21 Listing Image for 202 Nakoa Dr 3 of 21 Listing Image for 202 Nakoa Dr 4 of 21 Listing Image for 202 Nakoa Dr 5 of 21 Listing Image for 202 Nakoa Dr 6 of 21 Listing Image for 202 Nakoa Dr 7 of 21 Listing Image for 202 Nakoa Dr 8 of 21 Listing Image for 202 Nakoa Dr 9 of 21 Listing Image for 202 Nakoa Dr 10 of 21 Listing Image for 202 Nakoa Dr 11 of 21 Listing Image for 202 Nakoa Dr 12 of 21 Listing Image for 202 Nakoa Dr 13 of 21 Listing Image for 202 Nakoa Dr 14 of 21 Listing Image for 202 Nakoa Dr 15 of 21 Listing Image for 202 Nakoa Dr 16 of 21 Listing Image for 202 Nakoa Dr 17 of 21 Listing Image for 202 Nakoa Dr 18 of 21 Listing Image for 202 Nakoa Dr 19 of 21 Listing Image for 202 Nakoa Dr 20 of 21 Listing Image for 202 Nakoa Dr 21 of 21

$875,000

↓ $114,000

Wailuku

202 Nakoa Dr, Wailuku

3 Beds 1 Bath 1,118 SqFt Residential MLS® # 407349 Date Sold: May 11, 2026
Sold
Closed: 04/27/2026
Listing Image for 573 Pahi Ka St 1 of 32 Listing Image for 573 Pahi Ka St 2 of 32 Listing Image for 573 Pahi Ka St 3 of 32 Listing Image for 573 Pahi Ka St 4 of 32 Listing Image for 573 Pahi Ka St 5 of 32 Listing Image for 573 Pahi Ka St 6 of 32 Listing Image for 573 Pahi Ka St 7 of 32 Listing Image for 573 Pahi Ka St 8 of 32 Listing Image for 573 Pahi Ka St 9 of 32 Listing Image for 573 Pahi Ka St 10 of 32 Listing Image for 573 Pahi Ka St 11 of 32 Listing Image for 573 Pahi Ka St 12 of 32 Listing Image for 573 Pahi Ka St 13 of 32 Listing Image for 573 Pahi Ka St 14 of 32 Listing Image for 573 Pahi Ka St 15 of 32 Listing Image for 573 Pahi Ka St 16 of 32 Listing Image for 573 Pahi Ka St 17 of 32 Listing Image for 573 Pahi Ka St 18 of 32 Listing Image for 573 Pahi Ka St 19 of 32 Listing Image for 573 Pahi Ka St 20 of 32 Listing Image for 573 Pahi Ka St 21 of 32 Listing Image for 573 Pahi Ka St 22 of 32 Listing Image for 573 Pahi Ka St 23 of 32 Listing Image for 573 Pahi Ka St 24 of 32 Listing Image for 573 Pahi Ka St 25 of 32 Listing Image for 573 Pahi Ka St 26 of 32 Listing Image for 573 Pahi Ka St 27 of 32 Listing Image for 573 Pahi Ka St 28 of 32 Listing Image for 573 Pahi Ka St 29 of 32 Listing Image for 573 Pahi Ka St 30 of 32 Listing Image for 573 Pahi Ka St 31 of 32 Listing Image for 573 Pahi Ka St 32 of 32

$1,026,000

↓ $39,000

Skill Village

573 Pahi Ka St, Spreckelsville/Paia/Kuau

3 Beds 1.5 Baths 984 SqFt Residential MLS® # 407346 Date Sold: April 27, 2026
Sold
Closed: 12/05/2025
Listing Image for 3300 Wailea Alanui Dr 13d 1 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 2 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 3 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 4 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 5 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 6 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 7 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 8 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 9 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 10 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 11 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 12 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 13 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 14 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 15 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 16 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 17 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 18 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 19 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 20 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 21 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 22 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 23 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 24 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 25 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 26 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 27 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 28 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 29 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 30 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 31 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 32 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 33 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 34 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 35 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 36 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 37 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 38 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 39 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 40 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 41 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 42 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 43 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 44 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 45 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 46 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 47 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 48 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 49 of 50 Listing Image for 3300 Wailea Alanui Dr 13d 50 of 50

$1,300,000

Wailea Ekahi 13D

3300 Wailea Alanui Dr 13d, Wailea/Makena

1 Bed 1 Bath 792 SqFt Residential MLS® # 407334 Date Sold: December 5, 2025
Sold
Closed: 02/03/2026
Listing Image for 46 N Iwa Pl 1 of 47 Listing Image for 46 N Iwa Pl 2 of 47 Listing Image for 46 N Iwa Pl 3 of 47 Listing Image for 46 N Iwa Pl 4 of 47 Listing Image for 46 N Iwa Pl 5 of 47 Listing Image for 46 N Iwa Pl 6 of 47 Listing Image for 46 N Iwa Pl 7 of 47 Listing Image for 46 N Iwa Pl 8 of 47 Listing Image for 46 N Iwa Pl 9 of 47 Listing Image for 46 N Iwa Pl 10 of 47 Listing Image for 46 N Iwa Pl 11 of 47 Listing Image for 46 N Iwa Pl 12 of 47 Listing Image for 46 N Iwa Pl 13 of 47 Listing Image for 46 N Iwa Pl 14 of 47 Listing Image for 46 N Iwa Pl 15 of 47 Listing Image for 46 N Iwa Pl 16 of 47 Listing Image for 46 N Iwa Pl 17 of 47 Listing Image for 46 N Iwa Pl 18 of 47 Listing Image for 46 N Iwa Pl 19 of 47 Listing Image for 46 N Iwa Pl 20 of 47 Listing Image for 46 N Iwa Pl 21 of 47 Listing Image for 46 N Iwa Pl 22 of 47 Listing Image for 46 N Iwa Pl 23 of 47 Listing Image for 46 N Iwa Pl 24 of 47 Listing Image for 46 N Iwa Pl 25 of 47 Listing Image for 46 N Iwa Pl 26 of 47 Listing Image for 46 N Iwa Pl 27 of 47 Listing Image for 46 N Iwa Pl 28 of 47 Listing Image for 46 N Iwa Pl 29 of 47 Listing Image for 46 N Iwa Pl 30 of 47 Listing Image for 46 N Iwa Pl 31 of 47 Listing Image for 46 N Iwa Pl 32 of 47 Listing Image for 46 N Iwa Pl 33 of 47 Listing Image for 46 N Iwa Pl 34 of 47 Listing Image for 46 N Iwa Pl 35 of 47 Listing Image for 46 N Iwa Pl 36 of 47 Listing Image for 46 N Iwa Pl 37 of 47 Listing Image for 46 N Iwa Pl 38 of 47 Listing Image for 46 N Iwa Pl 39 of 47 Listing Image for 46 N Iwa Pl 40 of 47 Listing Image for 46 N Iwa Pl 41 of 47 Listing Image for 46 N Iwa Pl 42 of 47 Listing Image for 46 N Iwa Pl 43 of 47 Listing Image for 46 N Iwa Pl 44 of 47 Listing Image for 46 N Iwa Pl 45 of 47 Listing Image for 46 N Iwa Pl 46 of 47 Listing Image for 46 N Iwa Pl 47 of 47

$1,600,000

↓ $650,000

Kaanapali Hillside

46 N Iwa Pl, Kaanapali

3 Beds 3.5 Baths 2,454 SqFt Residential MLS® # 407328 Date Sold: February 3, 2026
Buying Real Estate on Maui

Buying Real Estate on Maui

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

Read the Guide
Sold
Closed: 12/19/2025
Listing Image for 50 Puu Anoano St 2801 1 of 50 Listing Image for 50 Puu Anoano St 2801 2 of 50 Listing Image for 50 Puu Anoano St 2801 3 of 50 Listing Image for 50 Puu Anoano St 2801 4 of 50 Listing Image for 50 Puu Anoano St 2801 5 of 50 Listing Image for 50 Puu Anoano St 2801 6 of 50 Listing Image for 50 Puu Anoano St 2801 7 of 50 Listing Image for 50 Puu Anoano St 2801 8 of 50 Listing Image for 50 Puu Anoano St 2801 9 of 50 Listing Image for 50 Puu Anoano St 2801 10 of 50 Listing Image for 50 Puu Anoano St 2801 11 of 50 Listing Image for 50 Puu Anoano St 2801 12 of 50 Listing Image for 50 Puu Anoano St 2801 13 of 50 Listing Image for 50 Puu Anoano St 2801 14 of 50 Listing Image for 50 Puu Anoano St 2801 15 of 50 Listing Image for 50 Puu Anoano St 2801 16 of 50 Listing Image for 50 Puu Anoano St 2801 17 of 50 Listing Image for 50 Puu Anoano St 2801 18 of 50 Listing Image for 50 Puu Anoano St 2801 19 of 50 Listing Image for 50 Puu Anoano St 2801 20 of 50 Listing Image for 50 Puu Anoano St 2801 21 of 50 Listing Image for 50 Puu Anoano St 2801 22 of 50 Listing Image for 50 Puu Anoano St 2801 23 of 50 Listing Image for 50 Puu Anoano St 2801 24 of 50 Listing Image for 50 Puu Anoano St 2801 25 of 50 Listing Image for 50 Puu Anoano St 2801 26 of 50 Listing Image for 50 Puu Anoano St 2801 27 of 50 Listing Image for 50 Puu Anoano St 2801 28 of 50 Listing Image for 50 Puu Anoano St 2801 29 of 50 Listing Image for 50 Puu Anoano St 2801 30 of 50 Listing Image for 50 Puu Anoano St 2801 31 of 50 Listing Image for 50 Puu Anoano St 2801 32 of 50 Listing Image for 50 Puu Anoano St 2801 33 of 50 Listing Image for 50 Puu Anoano St 2801 34 of 50 Listing Image for 50 Puu Anoano St 2801 35 of 50 Listing Image for 50 Puu Anoano St 2801 36 of 50 Listing Image for 50 Puu Anoano St 2801 37 of 50 Listing Image for 50 Puu Anoano St 2801 38 of 50 Listing Image for 50 Puu Anoano St 2801 39 of 50 Listing Image for 50 Puu Anoano St 2801 40 of 50 Listing Image for 50 Puu Anoano St 2801 41 of 50 Listing Image for 50 Puu Anoano St 2801 42 of 50 Listing Image for 50 Puu Anoano St 2801 43 of 50 Listing Image for 50 Puu Anoano St 2801 44 of 50 Listing Image for 50 Puu Anoano St 2801 45 of 50 Listing Image for 50 Puu Anoano St 2801 46 of 50 Listing Image for 50 Puu Anoano St 2801 47 of 50 Listing Image for 50 Puu Anoano St 2801 48 of 50 Listing Image for 50 Puu Anoano St 2801 49 of 50 Listing Image for 50 Puu Anoano St 2801 50 of 50

$1,400,000

Masters 2801

50 Puu Anoano St 2801, Kaanapali

2 Beds 2 Baths 1,516 SqFt Residential MLS® # 407329 Date Sold: December 19, 2025
Sold
Closed: 12/15/2025
Listing Image for 32 Ulumau Pl 1 of 16 Listing Image for 32 Ulumau Pl 2 of 16 Listing Image for 32 Ulumau Pl 3 of 16 Listing Image for 32 Ulumau Pl 4 of 16 Listing Image for 32 Ulumau Pl 5 of 16 Listing Image for 32 Ulumau Pl 6 of 16 Listing Image for 32 Ulumau Pl 7 of 16 Listing Image for 32 Ulumau Pl 8 of 16 Listing Image for 32 Ulumau Pl 9 of 16 Listing Image for 32 Ulumau Pl 10 of 16 Listing Image for 32 Ulumau Pl 11 of 16 Listing Image for 32 Ulumau Pl 12 of 16 Listing Image for 32 Ulumau Pl 13 of 16 Listing Image for 32 Ulumau Pl 14 of 16 Listing Image for 32 Ulumau Pl 15 of 16 Listing Image for 32 Ulumau Pl 16 of 16

$1,250,000

Spreckelsville/Paia/Kuau

32 Ulumau Pl, Spreckelsville/Paia/Kuau

5 Beds 3.5 Baths 2,068 SqFt Residential MLS® # 407327 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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