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 1590 Ono St 1 of 27 Listing Image for 1590 Ono St 2 of 27 Listing Image for 1590 Ono St 3 of 27 Listing Image for 1590 Ono St 4 of 27 Listing Image for 1590 Ono St 5 of 27 Listing Image for 1590 Ono St 6 of 27 Listing Image for 1590 Ono St 7 of 27 Listing Image for 1590 Ono St 8 of 27 Listing Image for 1590 Ono St 9 of 27 Listing Image for 1590 Ono St 10 of 27 Listing Image for 1590 Ono St 11 of 27 Listing Image for 1590 Ono St 12 of 27 Listing Image for 1590 Ono St 13 of 27 Listing Image for 1590 Ono St 14 of 27 Listing Image for 1590 Ono St 15 of 27 Listing Image for 1590 Ono St 16 of 27 Listing Image for 1590 Ono St 17 of 27 Listing Image for 1590 Ono St 18 of 27 Listing Image for 1590 Ono St 19 of 27 Listing Image for 1590 Ono St 20 of 27 Listing Image for 1590 Ono St 21 of 27 Listing Image for 1590 Ono St 22 of 27 Listing Image for 1590 Ono St 23 of 27 Listing Image for 1590 Ono St 24 of 27 Listing Image for 1590 Ono St 25 of 27 Listing Image for 1590 Ono St 26 of 27 Listing Image for 1590 Ono St 27 of 27

$930,000

↑ $41,000

Wailuku

1590 Ono St, Wailuku

3 Beds 2 Baths 864 SqFt Residential MLS® # 407980

Days on Market: 288

Berkshire Hathaway Maui Prop-L

Listing Image for 180 Hoomoku St 1 of 26 Listing Image for 180 Hoomoku St 2 of 26 Listing Image for 180 Hoomoku St 3 of 26 Listing Image for 180 Hoomoku St 4 of 26 Listing Image for 180 Hoomoku St 5 of 26 Listing Image for 180 Hoomoku St 6 of 26 Listing Image for 180 Hoomoku St 7 of 26 Listing Image for 180 Hoomoku St 8 of 26 Listing Image for 180 Hoomoku St 9 of 26 Listing Image for 180 Hoomoku St 10 of 26 Listing Image for 180 Hoomoku St 11 of 26 Listing Image for 180 Hoomoku St 12 of 26 Listing Image for 180 Hoomoku St 13 of 26 Listing Image for 180 Hoomoku St 14 of 26 Listing Image for 180 Hoomoku St 15 of 26 Listing Image for 180 Hoomoku St 16 of 26 Listing Image for 180 Hoomoku St 17 of 26 Listing Image for 180 Hoomoku St 18 of 26 Listing Image for 180 Hoomoku St 19 of 26 Listing Image for 180 Hoomoku St 20 of 26 Listing Image for 180 Hoomoku St 21 of 26 Listing Image for 180 Hoomoku St 22 of 26 Listing Image for 180 Hoomoku St 23 of 26 Listing Image for 180 Hoomoku St 24 of 26 Listing Image for 180 Hoomoku St 25 of 26 Listing Image for 180 Hoomoku St 26 of 26

$895,000

↓ $104,999

Kahului

180 Hoomoku St, Kahului

3 Beds 2 Baths 1,520 SqFt Residential MLS® # 407981

Days on Market: 288

Berkshire Hathaway Maui Prop-L

In Escrow
Listing Image for 50 Nohea Kai Dr 212 1 of 25 Listing Image for 50 Nohea Kai Dr 212 2 of 25 Listing Image for 50 Nohea Kai Dr 212 3 of 25 Listing Image for 50 Nohea Kai Dr 212 4 of 25 Listing Image for 50 Nohea Kai Dr 212 5 of 25 Listing Image for 50 Nohea Kai Dr 212 6 of 25 Listing Image for 50 Nohea Kai Dr 212 7 of 25 Listing Image for 50 Nohea Kai Dr 212 8 of 25 Listing Image for 50 Nohea Kai Dr 212 9 of 25 Listing Image for 50 Nohea Kai Dr 212 10 of 25 Listing Image for 50 Nohea Kai Dr 212 11 of 25 Listing Image for 50 Nohea Kai Dr 212 12 of 25 Listing Image for 50 Nohea Kai Dr 212 13 of 25 Listing Image for 50 Nohea Kai Dr 212 14 of 25 Listing Image for 50 Nohea Kai Dr 212 15 of 25 Listing Image for 50 Nohea Kai Dr 212 16 of 25 Listing Image for 50 Nohea Kai Dr 212 17 of 25 Listing Image for 50 Nohea Kai Dr 212 18 of 25 Listing Image for 50 Nohea Kai Dr 212 19 of 25 Listing Image for 50 Nohea Kai Dr 212 20 of 25 Listing Image for 50 Nohea Kai Dr 212 21 of 25 Listing Image for 50 Nohea Kai Dr 212 22 of 25 Listing Image for 50 Nohea Kai Dr 212 23 of 25 Listing Image for 50 Nohea Kai Dr 212 24 of 25 Listing Image for 50 Nohea Kai Dr 212 25 of 25

$1,299,000

↓ $200,000

Kaanapali Alii 212

50 Nohea Kai Dr 212, Kaanapali

1 Bed 2 Baths 1,439 SqFt Residential MLS® # 407952

Days on Market: 289

Susan Jackson Real Estate Cell: 865-206-1234

Listing Image for 50 Puu Anoano St 903 1 of 50 Listing Image for 50 Puu Anoano St 903 2 of 50 Listing Image for 50 Puu Anoano St 903 3 of 50 Listing Image for 50 Puu Anoano St 903 4 of 50 Listing Image for 50 Puu Anoano St 903 5 of 50 Listing Image for 50 Puu Anoano St 903 6 of 50 Listing Image for 50 Puu Anoano St 903 7 of 50 Listing Image for 50 Puu Anoano St 903 8 of 50 Listing Image for 50 Puu Anoano St 903 9 of 50 Listing Image for 50 Puu Anoano St 903 10 of 50 Listing Image for 50 Puu Anoano St 903 11 of 50 Listing Image for 50 Puu Anoano St 903 12 of 50 Listing Image for 50 Puu Anoano St 903 13 of 50 Listing Image for 50 Puu Anoano St 903 14 of 50 Listing Image for 50 Puu Anoano St 903 15 of 50 Listing Image for 50 Puu Anoano St 903 16 of 50 Listing Image for 50 Puu Anoano St 903 17 of 50 Listing Image for 50 Puu Anoano St 903 18 of 50 Listing Image for 50 Puu Anoano St 903 19 of 50 Listing Image for 50 Puu Anoano St 903 20 of 50 Listing Image for 50 Puu Anoano St 903 21 of 50 Listing Image for 50 Puu Anoano St 903 22 of 50 Listing Image for 50 Puu Anoano St 903 23 of 50 Listing Image for 50 Puu Anoano St 903 24 of 50 Listing Image for 50 Puu Anoano St 903 25 of 50 Listing Image for 50 Puu Anoano St 903 26 of 50 Listing Image for 50 Puu Anoano St 903 27 of 50 Listing Image for 50 Puu Anoano St 903 28 of 50 Listing Image for 50 Puu Anoano St 903 29 of 50 Listing Image for 50 Puu Anoano St 903 30 of 50 Listing Image for 50 Puu Anoano St 903 31 of 50 Listing Image for 50 Puu Anoano St 903 32 of 50 Listing Image for 50 Puu Anoano St 903 33 of 50 Listing Image for 50 Puu Anoano St 903 34 of 50 Listing Image for 50 Puu Anoano St 903 35 of 50 Listing Image for 50 Puu Anoano St 903 36 of 50 Listing Image for 50 Puu Anoano St 903 37 of 50 Listing Image for 50 Puu Anoano St 903 38 of 50 Listing Image for 50 Puu Anoano St 903 39 of 50 Listing Image for 50 Puu Anoano St 903 40 of 50 Listing Image for 50 Puu Anoano St 903 41 of 50 Listing Image for 50 Puu Anoano St 903 42 of 50 Listing Image for 50 Puu Anoano St 903 43 of 50 Listing Image for 50 Puu Anoano St 903 44 of 50 Listing Image for 50 Puu Anoano St 903 45 of 50 Listing Image for 50 Puu Anoano St 903 46 of 50 Listing Image for 50 Puu Anoano St 903 47 of 50 Listing Image for 50 Puu Anoano St 903 48 of 50 Listing Image for 50 Puu Anoano St 903 49 of 50 Listing Image for 50 Puu Anoano St 903 50 of 50

$1,444,000

↓ $1,000

Masters 903

50 Puu Anoano St 903, Kaanapali

2 Beds 2 Baths 1,512 SqFt Residential MLS® # 407945

Days on Market: 289

Maui Luxury Real Estate LLC

Short Term Rental
Listing Image for 10 Wailea Ekolu Pl 105 1 of 35 Listing Image for 10 Wailea Ekolu Pl 105 2 of 35 Listing Image for 10 Wailea Ekolu Pl 105 3 of 35 Listing Image for 10 Wailea Ekolu Pl 105 4 of 35 Listing Image for 10 Wailea Ekolu Pl 105 5 of 35 Listing Image for 10 Wailea Ekolu Pl 105 6 of 35 Listing Image for 10 Wailea Ekolu Pl 105 7 of 35 Listing Image for 10 Wailea Ekolu Pl 105 8 of 35 Listing Image for 10 Wailea Ekolu Pl 105 9 of 35 Listing Image for 10 Wailea Ekolu Pl 105 10 of 35 Listing Image for 10 Wailea Ekolu Pl 105 11 of 35 Listing Image for 10 Wailea Ekolu Pl 105 12 of 35 Listing Image for 10 Wailea Ekolu Pl 105 13 of 35 Listing Image for 10 Wailea Ekolu Pl 105 14 of 35 Listing Image for 10 Wailea Ekolu Pl 105 15 of 35 Listing Image for 10 Wailea Ekolu Pl 105 16 of 35 Listing Image for 10 Wailea Ekolu Pl 105 17 of 35 Listing Image for 10 Wailea Ekolu Pl 105 18 of 35 Listing Image for 10 Wailea Ekolu Pl 105 19 of 35 Listing Image for 10 Wailea Ekolu Pl 105 20 of 35 Listing Image for 10 Wailea Ekolu Pl 105 21 of 35 Listing Image for 10 Wailea Ekolu Pl 105 22 of 35 Listing Image for 10 Wailea Ekolu Pl 105 23 of 35 Listing Image for 10 Wailea Ekolu Pl 105 24 of 35 Listing Image for 10 Wailea Ekolu Pl 105 25 of 35 Listing Image for 10 Wailea Ekolu Pl 105 26 of 35 Listing Image for 10 Wailea Ekolu Pl 105 27 of 35 Listing Image for 10 Wailea Ekolu Pl 105 28 of 35 Listing Image for 10 Wailea Ekolu Pl 105 29 of 35 Listing Image for 10 Wailea Ekolu Pl 105 30 of 35 Listing Image for 10 Wailea Ekolu Pl 105 31 of 35 Listing Image for 10 Wailea Ekolu Pl 105 32 of 35 Listing Image for 10 Wailea Ekolu Pl 105 33 of 35 Listing Image for 10 Wailea Ekolu Pl 105 34 of 35 Listing Image for 10 Wailea Ekolu Pl 105 35 of 35

$1,470,000

↓ $5,000

Wailea Ekolu 105

10 Wailea Ekolu Pl 105, Wailea/Makena

2 Beds 2 Baths 1,071 SqFt Residential MLS® # 407940

Days on Market: 289

Coldwell Banker Island Prop(S) Cell: 808-298-8448

Short Term Rental
Listing Image for 150 Hauoli St 511 1 of 38 Listing Image for 150 Hauoli St 511 2 of 38 Listing Image for 150 Hauoli St 511 3 of 38 Listing Image for 150 Hauoli St 511 4 of 38 Listing Image for 150 Hauoli St 511 5 of 38 Listing Image for 150 Hauoli St 511 6 of 38 Listing Image for 150 Hauoli St 511 7 of 38 Listing Image for 150 Hauoli St 511 8 of 38 Listing Image for 150 Hauoli St 511 9 of 38 Listing Image for 150 Hauoli St 511 10 of 38 Listing Image for 150 Hauoli St 511 11 of 38 Listing Image for 150 Hauoli St 511 12 of 38 Listing Image for 150 Hauoli St 511 13 of 38 Listing Image for 150 Hauoli St 511 14 of 38 Listing Image for 150 Hauoli St 511 15 of 38 Listing Image for 150 Hauoli St 511 16 of 38 Listing Image for 150 Hauoli St 511 17 of 38 Listing Image for 150 Hauoli St 511 18 of 38 Listing Image for 150 Hauoli St 511 19 of 38 Listing Image for 150 Hauoli St 511 20 of 38 Listing Image for 150 Hauoli St 511 21 of 38 Listing Image for 150 Hauoli St 511 22 of 38 Listing Image for 150 Hauoli St 511 23 of 38 Listing Image for 150 Hauoli St 511 24 of 38 Listing Image for 150 Hauoli St 511 25 of 38 Listing Image for 150 Hauoli St 511 26 of 38 Listing Image for 150 Hauoli St 511 27 of 38 Listing Image for 150 Hauoli St 511 28 of 38 Listing Image for 150 Hauoli St 511 29 of 38 Listing Image for 150 Hauoli St 511 30 of 38 Listing Image for 150 Hauoli St 511 31 of 38 Listing Image for 150 Hauoli St 511 32 of 38 Listing Image for 150 Hauoli St 511 33 of 38 Listing Image for 150 Hauoli St 511 34 of 38 Listing Image for 150 Hauoli St 511 35 of 38 Listing Image for 150 Hauoli St 511 36 of 38 Listing Image for 150 Hauoli St 511 37 of 38 Listing Image for 150 Hauoli St 511 38 of 38

$899,000

↓ $51,000

Island Sands 511

150 Hauoli St 511, Maalaea

2 Beds 2 Baths 899 SqFt Residential MLS® # 407930

Days on Market: 292

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

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

$2,395,000

↓ $240,000

Kahana Ridge

17 Kahana Ridge Pl, Napili/Kahana/Honokowai

4 Beds 3 Baths 2,825 SqFt Residential MLS® # 407928

Days on Market: 292

Real Broker Cell: 808-298-2030

View 7 More Listings

Apply for a Home Equity Loan

While you may ideally want to sell your current house before buying a new one, this may not be an absolute requirement for some sellers. You could tap into your home’s equity by applying for an equity line of credit. Before moving forward with this possibility, be aware that the payment on the new home equity line will affect your debt-to-income ratio.

Mortgage lenders review your debt-to-income ratio as part of their qualification process. Because of this, you should discuss this option in detail with your lender to ensure that it will not impair your ability to qualify for a new mortgage.

Recent Sales on Maui

Sold
Closed: 10/01/2025
Listing Image for 44 Kulamanu Cir 1 of 31 Listing Image for 44 Kulamanu Cir 2 of 31 Listing Image for 44 Kulamanu Cir 3 of 31 Listing Image for 44 Kulamanu Cir 4 of 31 Listing Image for 44 Kulamanu Cir 5 of 31 Listing Image for 44 Kulamanu Cir 6 of 31 Listing Image for 44 Kulamanu Cir 7 of 31 Listing Image for 44 Kulamanu Cir 8 of 31 Listing Image for 44 Kulamanu Cir 9 of 31 Listing Image for 44 Kulamanu Cir 10 of 31 Listing Image for 44 Kulamanu Cir 11 of 31 Listing Image for 44 Kulamanu Cir 12 of 31 Listing Image for 44 Kulamanu Cir 13 of 31 Listing Image for 44 Kulamanu Cir 14 of 31 Listing Image for 44 Kulamanu Cir 15 of 31 Listing Image for 44 Kulamanu Cir 16 of 31 Listing Image for 44 Kulamanu Cir 17 of 31 Listing Image for 44 Kulamanu Cir 18 of 31 Listing Image for 44 Kulamanu Cir 19 of 31 Listing Image for 44 Kulamanu Cir 20 of 31 Listing Image for 44 Kulamanu Cir 21 of 31 Listing Image for 44 Kulamanu Cir 22 of 31 Listing Image for 44 Kulamanu Cir 23 of 31 Listing Image for 44 Kulamanu Cir 24 of 31 Listing Image for 44 Kulamanu Cir 25 of 31 Listing Image for 44 Kulamanu Cir 26 of 31 Listing Image for 44 Kulamanu Cir 27 of 31 Listing Image for 44 Kulamanu Cir 28 of 31 Listing Image for 44 Kulamanu Cir 29 of 31 Listing Image for 44 Kulamanu Cir 30 of 31 Listing Image for 44 Kulamanu Cir 31 of 31

$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
Sold
Closed: 02/11/2026
Listing Image for 286 Kulipuu Pl 1 of 41 Listing Image for 286 Kulipuu Pl 2 of 41 Listing Image for 286 Kulipuu Pl 3 of 41 Listing Image for 286 Kulipuu Pl 4 of 41 Listing Image for 286 Kulipuu Pl 5 of 41 Listing Image for 286 Kulipuu Pl 6 of 41 Listing Image for 286 Kulipuu Pl 7 of 41 Listing Image for 286 Kulipuu Pl 8 of 41 Listing Image for 286 Kulipuu Pl 9 of 41 Listing Image for 286 Kulipuu Pl 10 of 41 Listing Image for 286 Kulipuu Pl 11 of 41 Listing Image for 286 Kulipuu Pl 12 of 41 Listing Image for 286 Kulipuu Pl 13 of 41 Listing Image for 286 Kulipuu Pl 14 of 41 Listing Image for 286 Kulipuu Pl 15 of 41 Listing Image for 286 Kulipuu Pl 16 of 41 Listing Image for 286 Kulipuu Pl 17 of 41 Listing Image for 286 Kulipuu Pl 18 of 41 Listing Image for 286 Kulipuu Pl 19 of 41 Listing Image for 286 Kulipuu Pl 20 of 41 Listing Image for 286 Kulipuu Pl 21 of 41 Listing Image for 286 Kulipuu Pl 22 of 41 Listing Image for 286 Kulipuu Pl 23 of 41 Listing Image for 286 Kulipuu Pl 24 of 41 Listing Image for 286 Kulipuu Pl 25 of 41 Listing Image for 286 Kulipuu Pl 26 of 41 Listing Image for 286 Kulipuu Pl 27 of 41 Listing Image for 286 Kulipuu Pl 28 of 41 Listing Image for 286 Kulipuu Pl 29 of 41 Listing Image for 286 Kulipuu Pl 30 of 41 Listing Image for 286 Kulipuu Pl 31 of 41 Listing Image for 286 Kulipuu Pl 32 of 41 Listing Image for 286 Kulipuu Pl 33 of 41 Listing Image for 286 Kulipuu Pl 34 of 41 Listing Image for 286 Kulipuu Pl 35 of 41 Listing Image for 286 Kulipuu Pl 36 of 41 Listing Image for 286 Kulipuu Pl 37 of 41 Listing Image for 286 Kulipuu Pl 38 of 41 Listing Image for 286 Kulipuu Pl 39 of 41 Listing Image for 286 Kulipuu Pl 40 of 41 Listing Image for 286 Kulipuu Pl 41 of 41

$1,800,000

↓ $250,000

Ke Alii Kai

286 Kulipuu Pl, Kihei

5 Beds 4 Baths 2,219 SqFt Residential MLS® # 407277 Date Sold: February 11, 2026
Sold
Closed: 02/20/2026
Listing Image for 3300 Wailea Alanui Dr 20d 1 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 2 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 3 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 4 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 5 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 6 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 7 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 8 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 9 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 10 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 11 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 12 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 13 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 14 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 15 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 16 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 17 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 18 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 19 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 20 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 21 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 22 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 23 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 24 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 25 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 26 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 27 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 28 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 29 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 30 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 31 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 32 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 33 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 34 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 35 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 36 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 37 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 38 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 39 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 40 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 41 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 42 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 43 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 44 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 45 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 46 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 47 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 48 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 49 of 50 Listing Image for 3300 Wailea Alanui Dr 20d 50 of 50

$950,000

↓ $199,000

Wailea Ekahi 20D

3300 Wailea Alanui Dr 20d, Wailea/Makena

1 Bed 2 Baths 952 SqFt Residential MLS® # 407276 Date Sold: February 20, 2026
Sold
Closed: 01/30/2026
Listing Image for 95 Poailani Pl 19 1 of 50 Listing Image for 95 Poailani Pl 19 2 of 50 Listing Image for 95 Poailani Pl 19 3 of 50 Listing Image for 95 Poailani Pl 19 4 of 50 Listing Image for 95 Poailani Pl 19 5 of 50 Listing Image for 95 Poailani Pl 19 6 of 50 Listing Image for 95 Poailani Pl 19 7 of 50 Listing Image for 95 Poailani Pl 19 8 of 50 Listing Image for 95 Poailani Pl 19 9 of 50 Listing Image for 95 Poailani Pl 19 10 of 50 Listing Image for 95 Poailani Pl 19 11 of 50 Listing Image for 95 Poailani Pl 19 12 of 50 Listing Image for 95 Poailani Pl 19 13 of 50 Listing Image for 95 Poailani Pl 19 14 of 50 Listing Image for 95 Poailani Pl 19 15 of 50 Listing Image for 95 Poailani Pl 19 16 of 50 Listing Image for 95 Poailani Pl 19 17 of 50 Listing Image for 95 Poailani Pl 19 18 of 50 Listing Image for 95 Poailani Pl 19 19 of 50 Listing Image for 95 Poailani Pl 19 20 of 50 Listing Image for 95 Poailani Pl 19 21 of 50 Listing Image for 95 Poailani Pl 19 22 of 50 Listing Image for 95 Poailani Pl 19 23 of 50 Listing Image for 95 Poailani Pl 19 24 of 50 Listing Image for 95 Poailani Pl 19 25 of 50 Listing Image for 95 Poailani Pl 19 26 of 50 Listing Image for 95 Poailani Pl 19 27 of 50 Listing Image for 95 Poailani Pl 19 28 of 50 Listing Image for 95 Poailani Pl 19 29 of 50 Listing Image for 95 Poailani Pl 19 30 of 50 Listing Image for 95 Poailani Pl 19 31 of 50 Listing Image for 95 Poailani Pl 19 32 of 50 Listing Image for 95 Poailani Pl 19 33 of 50 Listing Image for 95 Poailani Pl 19 34 of 50 Listing Image for 95 Poailani Pl 19 35 of 50 Listing Image for 95 Poailani Pl 19 36 of 50 Listing Image for 95 Poailani Pl 19 37 of 50 Listing Image for 95 Poailani Pl 19 38 of 50 Listing Image for 95 Poailani Pl 19 39 of 50 Listing Image for 95 Poailani Pl 19 40 of 50 Listing Image for 95 Poailani Pl 19 41 of 50 Listing Image for 95 Poailani Pl 19 42 of 50 Listing Image for 95 Poailani Pl 19 43 of 50 Listing Image for 95 Poailani Pl 19 44 of 50 Listing Image for 95 Poailani Pl 19 45 of 50 Listing Image for 95 Poailani Pl 19 46 of 50 Listing Image for 95 Poailani Pl 19 47 of 50 Listing Image for 95 Poailani Pl 19 48 of 50 Listing Image for 95 Poailani Pl 19 49 of 50 Listing Image for 95 Poailani Pl 19 50 of 50

$1,895,000

Kanani Wailea 19

95 Poailani Pl 19, Wailea/Makena

3 Beds 2.5 Baths 2,229 SqFt Residential MLS® # 407264 Date Sold: January 30, 2026
Sold
Closed: 01/30/2026
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$1,895,000

Kanani Wailea

95 Poailani Pl Unit 19, Wailea/Makena

3 Beds 2.5 Baths 2,229 SqFt Residential MLS® # 407265 Date Sold: January 30, 2026
Sold
Closed: 09/26/2025
89 Oliona St 138, Makawao/Olinda/Haliimaile

$1,595,000

Hokuula

89 Oliona St 138, Makawao/Olinda/Haliimaile

4 Beds 3.5 Baths 2,095 SqFt Residential MLS® # 407261 Date Sold: September 26, 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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