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

$11,000,000

↓ $2,800,000

Spreckelsville/Paia/Kuau

43 Nonohe Pl, Spreckelsville/Paia/Kuau

5 Beds 5 Baths 4,493 SqFt Residential MLS® # 407684

Days on Market: 310

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

Listing Image for 257 Hokiokio Pl A 1 of 48 Listing Image for 257 Hokiokio Pl A 2 of 48 Listing Image for 257 Hokiokio Pl A 3 of 48 Listing Image for 257 Hokiokio Pl A 4 of 48 Listing Image for 257 Hokiokio Pl A 5 of 48 Listing Image for 257 Hokiokio Pl A 6 of 48 Listing Image for 257 Hokiokio Pl A 7 of 48 Listing Image for 257 Hokiokio Pl A 8 of 48 Listing Image for 257 Hokiokio Pl A 9 of 48 Listing Image for 257 Hokiokio Pl A 10 of 48 Listing Image for 257 Hokiokio Pl A 11 of 48 Listing Image for 257 Hokiokio Pl A 12 of 48 Listing Image for 257 Hokiokio Pl A 13 of 48 Listing Image for 257 Hokiokio Pl A 14 of 48 Listing Image for 257 Hokiokio Pl A 15 of 48 Listing Image for 257 Hokiokio Pl A 16 of 48 Listing Image for 257 Hokiokio Pl A 17 of 48 Listing Image for 257 Hokiokio Pl A 18 of 48 Listing Image for 257 Hokiokio Pl A 19 of 48 Listing Image for 257 Hokiokio Pl A 20 of 48 Listing Image for 257 Hokiokio Pl A 21 of 48 Listing Image for 257 Hokiokio Pl A 22 of 48 Listing Image for 257 Hokiokio Pl A 23 of 48 Listing Image for 257 Hokiokio Pl A 24 of 48 Listing Image for 257 Hokiokio Pl A 25 of 48 Listing Image for 257 Hokiokio Pl A 26 of 48 Listing Image for 257 Hokiokio Pl A 27 of 48 Listing Image for 257 Hokiokio Pl A 28 of 48 Listing Image for 257 Hokiokio Pl A 29 of 48 Listing Image for 257 Hokiokio Pl A 30 of 48 Listing Image for 257 Hokiokio Pl A 31 of 48 Listing Image for 257 Hokiokio Pl A 32 of 48 Listing Image for 257 Hokiokio Pl A 33 of 48 Listing Image for 257 Hokiokio Pl A 34 of 48 Listing Image for 257 Hokiokio Pl A 35 of 48 Listing Image for 257 Hokiokio Pl A 36 of 48 Listing Image for 257 Hokiokio Pl A 37 of 48 Listing Image for 257 Hokiokio Pl A 38 of 48 Listing Image for 257 Hokiokio Pl A 39 of 48 Listing Image for 257 Hokiokio Pl A 40 of 48 Listing Image for 257 Hokiokio Pl A 41 of 48 Listing Image for 257 Hokiokio Pl A 42 of 48 Listing Image for 257 Hokiokio Pl A 43 of 48 Listing Image for 257 Hokiokio Pl A 44 of 48 Listing Image for 257 Hokiokio Pl A 45 of 48 Listing Image for 257 Hokiokio Pl A 46 of 48 Listing Image for 257 Hokiokio Pl A 47 of 48 Listing Image for 257 Hokiokio Pl A 48 of 48

$5,200,000

Lahaina

257 Hokiokio Pl A, Lahaina

5 Beds 4.5 Baths 3,556 SqFt Residential MLS® # 407666

Days on Market: 313

eXp Realty Cell: 808-269-8633

Listing Image for 2399 Umeke Cir 68 1 of 37 Listing Image for 2399 Umeke Cir 68 2 of 37 Listing Image for 2399 Umeke Cir 68 3 of 37 Listing Image for 2399 Umeke Cir 68 4 of 37 Listing Image for 2399 Umeke Cir 68 5 of 37 Listing Image for 2399 Umeke Cir 68 6 of 37 Listing Image for 2399 Umeke Cir 68 7 of 37 Listing Image for 2399 Umeke Cir 68 8 of 37 Listing Image for 2399 Umeke Cir 68 9 of 37 Listing Image for 2399 Umeke Cir 68 10 of 37 Listing Image for 2399 Umeke Cir 68 11 of 37 Listing Image for 2399 Umeke Cir 68 12 of 37 Listing Image for 2399 Umeke Cir 68 13 of 37 Listing Image for 2399 Umeke Cir 68 14 of 37 Listing Image for 2399 Umeke Cir 68 15 of 37 Listing Image for 2399 Umeke Cir 68 16 of 37 Listing Image for 2399 Umeke Cir 68 17 of 37 Listing Image for 2399 Umeke Cir 68 18 of 37 Listing Image for 2399 Umeke Cir 68 19 of 37 Listing Image for 2399 Umeke Cir 68 20 of 37 Listing Image for 2399 Umeke Cir 68 21 of 37 Listing Image for 2399 Umeke Cir 68 22 of 37 Listing Image for 2399 Umeke Cir 68 23 of 37 Listing Image for 2399 Umeke Cir 68 24 of 37 Listing Image for 2399 Umeke Cir 68 25 of 37 Listing Image for 2399 Umeke Cir 68 26 of 37 Listing Image for 2399 Umeke Cir 68 27 of 37 Listing Image for 2399 Umeke Cir 68 28 of 37 Listing Image for 2399 Umeke Cir 68 29 of 37 Listing Image for 2399 Umeke Cir 68 30 of 37 Listing Image for 2399 Umeke Cir 68 31 of 37 Listing Image for 2399 Umeke Cir 68 32 of 37 Listing Image for 2399 Umeke Cir 68 33 of 37 Listing Image for 2399 Umeke Cir 68 34 of 37 Listing Image for 2399 Umeke Cir 68 35 of 37 Listing Image for 2399 Umeke Cir 68 36 of 37 Listing Image for 2399 Umeke Cir 68 37 of 37

$3,000,000

↑ $850,000

Hokulani Golf Villas

2399 Umeke Cir 68, Kihei

3 Beds 3.5 Baths 2,443 SqFt Residential MLS® # 407659

Days on Market: 315

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

Short Term Rental
Listing Image for 5295 Lower Honoapiilani Road Rd B-5 1 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 2 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 3 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 4 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 5 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 6 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 7 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 8 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 9 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 10 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 11 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 12 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 13 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 14 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 15 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 16 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 17 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 18 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 19 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 20 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 21 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 22 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 23 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 24 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 25 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 26 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 27 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 28 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 29 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 30 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 31 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 32 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 33 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 34 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 35 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 36 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 37 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 38 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 39 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 40 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 41 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 42 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 43 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 44 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 45 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 46 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 47 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 48 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 49 of 50 Listing Image for 5295 Lower Honoapiilani Road Rd B-5 50 of 50

$999,999

↓ $158,001

Napili Point B-5

5295 Lower Honoapiilani Road Rd B-5, Napili/Kahana/Honokowai

1 Bed 1 Bath 720 SqFt Residential MLS® # 407646

Days on Market: 315

Maui Paradise Properties LLC 808-661-1535

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

$2,695,000

Spreckelsville/Paia/Kuau

15 Nalu Pl, Spreckelsville/Paia/Kuau

5 Beds 4 Baths 1,753 SqFt Residential MLS® # 407642

Days on Market: 315

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

Listing Image for 2399 Umeke Cir 68 1 of 37 Listing Image for 2399 Umeke Cir 68 2 of 37 Listing Image for 2399 Umeke Cir 68 3 of 37 Listing Image for 2399 Umeke Cir 68 4 of 37 Listing Image for 2399 Umeke Cir 68 5 of 37 Listing Image for 2399 Umeke Cir 68 6 of 37 Listing Image for 2399 Umeke Cir 68 7 of 37 Listing Image for 2399 Umeke Cir 68 8 of 37 Listing Image for 2399 Umeke Cir 68 9 of 37 Listing Image for 2399 Umeke Cir 68 10 of 37 Listing Image for 2399 Umeke Cir 68 11 of 37 Listing Image for 2399 Umeke Cir 68 12 of 37 Listing Image for 2399 Umeke Cir 68 13 of 37 Listing Image for 2399 Umeke Cir 68 14 of 37 Listing Image for 2399 Umeke Cir 68 15 of 37 Listing Image for 2399 Umeke Cir 68 16 of 37 Listing Image for 2399 Umeke Cir 68 17 of 37 Listing Image for 2399 Umeke Cir 68 18 of 37 Listing Image for 2399 Umeke Cir 68 19 of 37 Listing Image for 2399 Umeke Cir 68 20 of 37 Listing Image for 2399 Umeke Cir 68 21 of 37 Listing Image for 2399 Umeke Cir 68 22 of 37 Listing Image for 2399 Umeke Cir 68 23 of 37 Listing Image for 2399 Umeke Cir 68 24 of 37 Listing Image for 2399 Umeke Cir 68 25 of 37 Listing Image for 2399 Umeke Cir 68 26 of 37 Listing Image for 2399 Umeke Cir 68 27 of 37 Listing Image for 2399 Umeke Cir 68 28 of 37 Listing Image for 2399 Umeke Cir 68 29 of 37 Listing Image for 2399 Umeke Cir 68 30 of 37 Listing Image for 2399 Umeke Cir 68 31 of 37 Listing Image for 2399 Umeke Cir 68 32 of 37 Listing Image for 2399 Umeke Cir 68 33 of 37 Listing Image for 2399 Umeke Cir 68 34 of 37 Listing Image for 2399 Umeke Cir 68 35 of 37 Listing Image for 2399 Umeke Cir 68 36 of 37 Listing Image for 2399 Umeke Cir 68 37 of 37

$3,000,000

Hokulani Golf Villas 68

2399 Umeke Cir 68, Kihei

3 Beds 3.5 Baths 2,443 SqFt Residential MLS® # 407638

Days on Market: 315

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

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

$1,590,000

↓ $109,000

Honokeana Subdivison

31 Pualu Loop, Napili/Kahana/Honokowai

5 Beds 4 Baths 2,576 SqFt Residential MLS® # 407585

Days on Market: 320

Coldwell Banker Island Prop-KP Cell: 808-357-4000

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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: 12/10/2025
Listing Image for 95 Meheu Cir 1 of 23 Listing Image for 95 Meheu Cir 2 of 23 Listing Image for 95 Meheu Cir 3 of 23 Listing Image for 95 Meheu Cir 4 of 23 Listing Image for 95 Meheu Cir 5 of 23 Listing Image for 95 Meheu Cir 6 of 23 Listing Image for 95 Meheu Cir 7 of 23 Listing Image for 95 Meheu Cir 8 of 23 Listing Image for 95 Meheu Cir 9 of 23 Listing Image for 95 Meheu Cir 10 of 23 Listing Image for 95 Meheu Cir 11 of 23 Listing Image for 95 Meheu Cir 12 of 23 Listing Image for 95 Meheu Cir 13 of 23 Listing Image for 95 Meheu Cir 14 of 23 Listing Image for 95 Meheu Cir 15 of 23 Listing Image for 95 Meheu Cir 16 of 23 Listing Image for 95 Meheu Cir 17 of 23 Listing Image for 95 Meheu Cir 18 of 23 Listing Image for 95 Meheu Cir 19 of 23 Listing Image for 95 Meheu Cir 20 of 23 Listing Image for 95 Meheu Cir 21 of 23 Listing Image for 95 Meheu Cir 22 of 23 Listing Image for 95 Meheu Cir 23 of 23

$970,000

Traditions at Maui Lani

95 Meheu Cir, Kahului

3 Beds 2.5 Baths 1,298 SqFt Residential MLS® # 407187 Date Sold: December 10, 2025
Sold
Closed: 11/20/2025
Listing Image for 87 Miha Pl 1 of 50 Listing Image for 87 Miha Pl 2 of 50 Listing Image for 87 Miha Pl 3 of 50 Listing Image for 87 Miha Pl 4 of 50 Listing Image for 87 Miha Pl 5 of 50 Listing Image for 87 Miha Pl 6 of 50 Listing Image for 87 Miha Pl 7 of 50 Listing Image for 87 Miha Pl 8 of 50 Listing Image for 87 Miha Pl 9 of 50 Listing Image for 87 Miha Pl 10 of 50 Listing Image for 87 Miha Pl 11 of 50 Listing Image for 87 Miha Pl 12 of 50 Listing Image for 87 Miha Pl 13 of 50 Listing Image for 87 Miha Pl 14 of 50 Listing Image for 87 Miha Pl 15 of 50 Listing Image for 87 Miha Pl 16 of 50 Listing Image for 87 Miha Pl 17 of 50 Listing Image for 87 Miha Pl 18 of 50 Listing Image for 87 Miha Pl 19 of 50 Listing Image for 87 Miha Pl 20 of 50 Listing Image for 87 Miha Pl 21 of 50 Listing Image for 87 Miha Pl 22 of 50 Listing Image for 87 Miha Pl 23 of 50 Listing Image for 87 Miha Pl 24 of 50 Listing Image for 87 Miha Pl 25 of 50 Listing Image for 87 Miha Pl 26 of 50 Listing Image for 87 Miha Pl 27 of 50 Listing Image for 87 Miha Pl 28 of 50 Listing Image for 87 Miha Pl 29 of 50 Listing Image for 87 Miha Pl 30 of 50 Listing Image for 87 Miha Pl 31 of 50 Listing Image for 87 Miha Pl 32 of 50 Listing Image for 87 Miha Pl 33 of 50 Listing Image for 87 Miha Pl 34 of 50 Listing Image for 87 Miha Pl 35 of 50 Listing Image for 87 Miha Pl 36 of 50 Listing Image for 87 Miha Pl 37 of 50 Listing Image for 87 Miha Pl 38 of 50 Listing Image for 87 Miha Pl 39 of 50 Listing Image for 87 Miha Pl 40 of 50 Listing Image for 87 Miha Pl 41 of 50 Listing Image for 87 Miha Pl 42 of 50 Listing Image for 87 Miha Pl 43 of 50 Listing Image for 87 Miha Pl 44 of 50 Listing Image for 87 Miha Pl 45 of 50 Listing Image for 87 Miha Pl 46 of 50 Listing Image for 87 Miha Pl 47 of 50 Listing Image for 87 Miha Pl 48 of 50 Listing Image for 87 Miha Pl 49 of 50 Listing Image for 87 Miha Pl 50 of 50

$1,145,000

↓ $150,000

Waimahaihai

87 Miha Pl, Kihei

3 Beds 2 Baths 1,210 SqFt Residential MLS® # 407092 Date Sold: November 20, 2025
Sold
Closed: 01/23/2026
Listing Image for 3800 Wailea Alanui Dr J 505 1 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 2 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 3 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 4 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 5 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 6 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 7 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 8 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 9 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 10 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 11 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 12 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 13 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 14 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 15 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 16 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 17 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 18 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 19 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 20 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 21 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 22 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 23 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 24 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 25 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 26 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 27 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 28 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 29 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 30 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 31 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 32 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 33 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 34 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 35 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 36 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 37 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 38 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 39 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 40 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 41 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 42 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 43 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 44 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 45 of 46 Listing Image for 3800 Wailea Alanui Dr J 505 46 of 46

$6,125,000

Wailea Beach Villas J 505

3800 Wailea Alanui Dr J 505, Wailea/Makena

3 Beds 3 Baths 1,961 SqFt Residential MLS® # 407172 Date Sold: January 23, 2026
Sold
Closed: 12/12/2025
Listing Image for 1833 Hookili Rd Unit A 1 of 50 Listing Image for 1833 Hookili Rd Unit A 2 of 50 Listing Image for 1833 Hookili Rd Unit A 3 of 50 Listing Image for 1833 Hookili Rd Unit A 4 of 50 Listing Image for 1833 Hookili Rd Unit A 5 of 50 Listing Image for 1833 Hookili Rd Unit A 6 of 50 Listing Image for 1833 Hookili Rd Unit A 7 of 50 Listing Image for 1833 Hookili Rd Unit A 8 of 50 Listing Image for 1833 Hookili Rd Unit A 9 of 50 Listing Image for 1833 Hookili Rd Unit A 10 of 50 Listing Image for 1833 Hookili Rd Unit A 11 of 50 Listing Image for 1833 Hookili Rd Unit A 12 of 50 Listing Image for 1833 Hookili Rd Unit A 13 of 50 Listing Image for 1833 Hookili Rd Unit A 14 of 50 Listing Image for 1833 Hookili Rd Unit A 15 of 50 Listing Image for 1833 Hookili Rd Unit A 16 of 50 Listing Image for 1833 Hookili Rd Unit A 17 of 50 Listing Image for 1833 Hookili Rd Unit A 18 of 50 Listing Image for 1833 Hookili Rd Unit A 19 of 50 Listing Image for 1833 Hookili Rd Unit A 20 of 50 Listing Image for 1833 Hookili Rd Unit A 21 of 50 Listing Image for 1833 Hookili Rd Unit A 22 of 50 Listing Image for 1833 Hookili Rd Unit A 23 of 50 Listing Image for 1833 Hookili Rd Unit A 24 of 50 Listing Image for 1833 Hookili Rd Unit A 25 of 50 Listing Image for 1833 Hookili Rd Unit A 26 of 50 Listing Image for 1833 Hookili Rd Unit A 27 of 50 Listing Image for 1833 Hookili Rd Unit A 28 of 50 Listing Image for 1833 Hookili Rd Unit A 29 of 50 Listing Image for 1833 Hookili Rd Unit A 30 of 50 Listing Image for 1833 Hookili Rd Unit A 31 of 50 Listing Image for 1833 Hookili Rd Unit A 32 of 50 Listing Image for 1833 Hookili Rd Unit A 33 of 50 Listing Image for 1833 Hookili Rd Unit A 34 of 50 Listing Image for 1833 Hookili Rd Unit A 35 of 50 Listing Image for 1833 Hookili Rd Unit A 36 of 50 Listing Image for 1833 Hookili Rd Unit A 37 of 50 Listing Image for 1833 Hookili Rd Unit A 38 of 50 Listing Image for 1833 Hookili Rd Unit A 39 of 50 Listing Image for 1833 Hookili Rd Unit A 40 of 50 Listing Image for 1833 Hookili Rd Unit A 41 of 50 Listing Image for 1833 Hookili Rd Unit A 42 of 50 Listing Image for 1833 Hookili Rd Unit A 43 of 50 Listing Image for 1833 Hookili Rd Unit A 44 of 50 Listing Image for 1833 Hookili Rd Unit A 45 of 50 Listing Image for 1833 Hookili Rd Unit A 46 of 50 Listing Image for 1833 Hookili Rd Unit A 47 of 50 Listing Image for 1833 Hookili Rd Unit A 48 of 50 Listing Image for 1833 Hookili Rd Unit A 49 of 50 Listing Image for 1833 Hookili Rd Unit A 50 of 50

$2,925,000

Peahi Hui

1833 Hookili Rd Unit A, Haiku

4 Beds 3 Baths 2,990 SqFt Residential MLS® # 407157 Date Sold: December 12, 2025
Sold
Closed: 10/06/2025
Listing Image for 50 Nohea Kai Dr 2-401 1 of 29 Listing Image for 50 Nohea Kai Dr 2-401 2 of 29 Listing Image for 50 Nohea Kai Dr 2-401 3 of 29 Listing Image for 50 Nohea Kai Dr 2-401 4 of 29 Listing Image for 50 Nohea Kai Dr 2-401 5 of 29 Listing Image for 50 Nohea Kai Dr 2-401 6 of 29 Listing Image for 50 Nohea Kai Dr 2-401 7 of 29 Listing Image for 50 Nohea Kai Dr 2-401 8 of 29 Listing Image for 50 Nohea Kai Dr 2-401 9 of 29 Listing Image for 50 Nohea Kai Dr 2-401 10 of 29 Listing Image for 50 Nohea Kai Dr 2-401 11 of 29 Listing Image for 50 Nohea Kai Dr 2-401 12 of 29 Listing Image for 50 Nohea Kai Dr 2-401 13 of 29 Listing Image for 50 Nohea Kai Dr 2-401 14 of 29 Listing Image for 50 Nohea Kai Dr 2-401 15 of 29 Listing Image for 50 Nohea Kai Dr 2-401 16 of 29 Listing Image for 50 Nohea Kai Dr 2-401 17 of 29 Listing Image for 50 Nohea Kai Dr 2-401 18 of 29 Listing Image for 50 Nohea Kai Dr 2-401 19 of 29 Listing Image for 50 Nohea Kai Dr 2-401 20 of 29 Listing Image for 50 Nohea Kai Dr 2-401 21 of 29 Listing Image for 50 Nohea Kai Dr 2-401 22 of 29 Listing Image for 50 Nohea Kai Dr 2-401 23 of 29 Listing Image for 50 Nohea Kai Dr 2-401 24 of 29 Listing Image for 50 Nohea Kai Dr 2-401 25 of 29 Listing Image for 50 Nohea Kai Dr 2-401 26 of 29 Listing Image for 50 Nohea Kai Dr 2-401 27 of 29 Listing Image for 50 Nohea Kai Dr 2-401 28 of 29 Listing Image for 50 Nohea Kai Dr 2-401 29 of 29

$2,485,000

Kaanapali Alii 2-401

50 Nohea Kai Dr 2-401, Kaanapali

1 Bed 2 Baths 1,441 SqFt Residential MLS® # 407105 Date Sold: October 6, 2025
Sold
Closed: 03/17/2026
Listing Image for 758 Lanina Pl 1 of 36 Listing Image for 758 Lanina Pl 2 of 36 Listing Image for 758 Lanina Pl 3 of 36 Listing Image for 758 Lanina Pl 4 of 36 Listing Image for 758 Lanina Pl 5 of 36 Listing Image for 758 Lanina Pl 6 of 36 Listing Image for 758 Lanina Pl 7 of 36 Listing Image for 758 Lanina Pl 8 of 36 Listing Image for 758 Lanina Pl 9 of 36 Listing Image for 758 Lanina Pl 10 of 36 Listing Image for 758 Lanina Pl 11 of 36 Listing Image for 758 Lanina Pl 12 of 36 Listing Image for 758 Lanina Pl 13 of 36 Listing Image for 758 Lanina Pl 14 of 36 Listing Image for 758 Lanina Pl 15 of 36 Listing Image for 758 Lanina Pl 16 of 36 Listing Image for 758 Lanina Pl 17 of 36 Listing Image for 758 Lanina Pl 18 of 36 Listing Image for 758 Lanina Pl 19 of 36 Listing Image for 758 Lanina Pl 20 of 36 Listing Image for 758 Lanina Pl 21 of 36 Listing Image for 758 Lanina Pl 22 of 36 Listing Image for 758 Lanina Pl 23 of 36 Listing Image for 758 Lanina Pl 24 of 36 Listing Image for 758 Lanina Pl 25 of 36 Listing Image for 758 Lanina Pl 26 of 36 Listing Image for 758 Lanina Pl 27 of 36 Listing Image for 758 Lanina Pl 28 of 36 Listing Image for 758 Lanina Pl 29 of 36 Listing Image for 758 Lanina Pl 30 of 36 Listing Image for 758 Lanina Pl 31 of 36 Listing Image for 758 Lanina Pl 32 of 36 Listing Image for 758 Lanina Pl 33 of 36 Listing Image for 758 Lanina Pl 34 of 36 Listing Image for 758 Lanina Pl 35 of 36 Listing Image for 758 Lanina Pl 36 of 36

$1,875,000

↓ $124,000

Maui Meadows

758 Lanina Pl, Maui Meadows

3 Beds 3 Baths 2,344 SqFt Residential MLS® # 407171 Date Sold: March 17, 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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