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 167 Lower Waiehu Beach Rd 1 of 38 Listing Image for 167 Lower Waiehu Beach Rd 2 of 38 Listing Image for 167 Lower Waiehu Beach Rd 3 of 38 Listing Image for 167 Lower Waiehu Beach Rd 4 of 38 Listing Image for 167 Lower Waiehu Beach Rd 5 of 38 Listing Image for 167 Lower Waiehu Beach Rd 6 of 38 Listing Image for 167 Lower Waiehu Beach Rd 7 of 38 Listing Image for 167 Lower Waiehu Beach Rd 8 of 38 Listing Image for 167 Lower Waiehu Beach Rd 9 of 38 Listing Image for 167 Lower Waiehu Beach Rd 10 of 38 Listing Image for 167 Lower Waiehu Beach Rd 11 of 38 Listing Image for 167 Lower Waiehu Beach Rd 12 of 38 Listing Image for 167 Lower Waiehu Beach Rd 13 of 38 Listing Image for 167 Lower Waiehu Beach Rd 14 of 38 Listing Image for 167 Lower Waiehu Beach Rd 15 of 38 Listing Image for 167 Lower Waiehu Beach Rd 16 of 38 Listing Image for 167 Lower Waiehu Beach Rd 17 of 38 Listing Image for 167 Lower Waiehu Beach Rd 18 of 38 Listing Image for 167 Lower Waiehu Beach Rd 19 of 38 Listing Image for 167 Lower Waiehu Beach Rd 20 of 38 Listing Image for 167 Lower Waiehu Beach Rd 21 of 38 Listing Image for 167 Lower Waiehu Beach Rd 22 of 38 Listing Image for 167 Lower Waiehu Beach Rd 23 of 38 Listing Image for 167 Lower Waiehu Beach Rd 24 of 38 Listing Image for 167 Lower Waiehu Beach Rd 25 of 38 Listing Image for 167 Lower Waiehu Beach Rd 26 of 38 Listing Image for 167 Lower Waiehu Beach Rd 27 of 38 Listing Image for 167 Lower Waiehu Beach Rd 28 of 38 Listing Image for 167 Lower Waiehu Beach Rd 29 of 38 Listing Image for 167 Lower Waiehu Beach Rd 30 of 38 Listing Image for 167 Lower Waiehu Beach Rd 31 of 38 Listing Image for 167 Lower Waiehu Beach Rd 32 of 38 Listing Image for 167 Lower Waiehu Beach Rd 33 of 38 Listing Image for 167 Lower Waiehu Beach Rd 34 of 38 Listing Image for 167 Lower Waiehu Beach Rd 35 of 38 Listing Image for 167 Lower Waiehu Beach Rd 36 of 38 Listing Image for 167 Lower Waiehu Beach Rd 37 of 38 Listing Image for 167 Lower Waiehu Beach Rd 38 of 38

$1,695,000

↓ $50,000

Wailuku

167 Lower Waiehu Beach Rd, Wailuku

5 Beds 3 Baths 1,920 SqFt Residential MLS® # 406777

Days on Market: 406

Hawaii Life (W) Cell: 808-283-2222

Short Term Rental
Listing Image for 2575 S Kihei Rd Q-104 1 of 50 Listing Image for 2575 S Kihei Rd Q-104 2 of 50 Listing Image for 2575 S Kihei Rd Q-104 3 of 50 Listing Image for 2575 S Kihei Rd Q-104 4 of 50 Listing Image for 2575 S Kihei Rd Q-104 5 of 50 Listing Image for 2575 S Kihei Rd Q-104 6 of 50 Listing Image for 2575 S Kihei Rd Q-104 7 of 50 Listing Image for 2575 S Kihei Rd Q-104 8 of 50 Listing Image for 2575 S Kihei Rd Q-104 9 of 50 Listing Image for 2575 S Kihei Rd Q-104 10 of 50 Listing Image for 2575 S Kihei Rd Q-104 11 of 50 Listing Image for 2575 S Kihei Rd Q-104 12 of 50 Listing Image for 2575 S Kihei Rd Q-104 13 of 50 Listing Image for 2575 S Kihei Rd Q-104 14 of 50 Listing Image for 2575 S Kihei Rd Q-104 15 of 50 Listing Image for 2575 S Kihei Rd Q-104 16 of 50 Listing Image for 2575 S Kihei Rd Q-104 17 of 50 Listing Image for 2575 S Kihei Rd Q-104 18 of 50 Listing Image for 2575 S Kihei Rd Q-104 19 of 50 Listing Image for 2575 S Kihei Rd Q-104 20 of 50 Listing Image for 2575 S Kihei Rd Q-104 21 of 50 Listing Image for 2575 S Kihei Rd Q-104 22 of 50 Listing Image for 2575 S Kihei Rd Q-104 23 of 50 Listing Image for 2575 S Kihei Rd Q-104 24 of 50 Listing Image for 2575 S Kihei Rd Q-104 25 of 50 Listing Image for 2575 S Kihei Rd Q-104 26 of 50 Listing Image for 2575 S Kihei Rd Q-104 27 of 50 Listing Image for 2575 S Kihei Rd Q-104 28 of 50 Listing Image for 2575 S Kihei Rd Q-104 29 of 50 Listing Image for 2575 S Kihei Rd Q-104 30 of 50 Listing Image for 2575 S Kihei Rd Q-104 31 of 50 Listing Image for 2575 S Kihei Rd Q-104 32 of 50 Listing Image for 2575 S Kihei Rd Q-104 33 of 50 Listing Image for 2575 S Kihei Rd Q-104 34 of 50 Listing Image for 2575 S Kihei Rd Q-104 35 of 50 Listing Image for 2575 S Kihei Rd Q-104 36 of 50 Listing Image for 2575 S Kihei Rd Q-104 37 of 50 Listing Image for 2575 S Kihei Rd Q-104 38 of 50 Listing Image for 2575 S Kihei Rd Q-104 39 of 50 Listing Image for 2575 S Kihei Rd Q-104 40 of 50 Listing Image for 2575 S Kihei Rd Q-104 41 of 50 Listing Image for 2575 S Kihei Rd Q-104 42 of 50 Listing Image for 2575 S Kihei Rd Q-104 43 of 50 Listing Image for 2575 S Kihei Rd Q-104 44 of 50 Listing Image for 2575 S Kihei Rd Q-104 45 of 50 Listing Image for 2575 S Kihei Rd Q-104 46 of 50 Listing Image for 2575 S Kihei Rd Q-104 47 of 50 Listing Image for 2575 S Kihei Rd Q-104 48 of 50 Listing Image for 2575 S Kihei Rd Q-104 49 of 50 Listing Image for 2575 S Kihei Rd Q-104 50 of 50

$900,000

↓ $100,000

Maui Banyan Q-104

2575 S Kihei Rd Q-104, Kihei

2 Beds 2 Baths 900 SqFt Residential MLS® # 405863

Days on Market: 500

Romvari Realty Ltd

In Escrow
Listing Image for 335 Hoalike St 1 of 33 Listing Image for 335 Hoalike St 2 of 33 Listing Image for 335 Hoalike St 3 of 33 Listing Image for 335 Hoalike St 4 of 33 Listing Image for 335 Hoalike St 5 of 33 Listing Image for 335 Hoalike St 6 of 33 Listing Image for 335 Hoalike St 7 of 33 Listing Image for 335 Hoalike St 8 of 33 Listing Image for 335 Hoalike St 9 of 33 Listing Image for 335 Hoalike St 10 of 33 Listing Image for 335 Hoalike St 11 of 33 Listing Image for 335 Hoalike St 12 of 33 Listing Image for 335 Hoalike St 13 of 33 Listing Image for 335 Hoalike St 14 of 33 Listing Image for 335 Hoalike St 15 of 33 Listing Image for 335 Hoalike St 16 of 33 Listing Image for 335 Hoalike St 17 of 33 Listing Image for 335 Hoalike St 18 of 33 Listing Image for 335 Hoalike St 19 of 33 Listing Image for 335 Hoalike St 20 of 33 Listing Image for 335 Hoalike St 21 of 33 Listing Image for 335 Hoalike St 22 of 33 Listing Image for 335 Hoalike St 23 of 33 Listing Image for 335 Hoalike St 24 of 33 Listing Image for 335 Hoalike St 25 of 33 Listing Image for 335 Hoalike St 26 of 33 Listing Image for 335 Hoalike St 27 of 33 Listing Image for 335 Hoalike St 28 of 33 Listing Image for 335 Hoalike St 29 of 33 Listing Image for 335 Hoalike St 30 of 33 Listing Image for 335 Hoalike St 31 of 33 Listing Image for 335 Hoalike St 32 of 33 Listing Image for 335 Hoalike St 33 of 33

$999,999

↓ $145,001

Ohukai

335 Hoalike St, Kihei

3 Beds 2 Baths 984 SqFt Residential MLS® # 406751

Days on Market: 407

Maui & Co Real Estate LLC

Short Term Rental
Listing Image for 106 Kaanapali Shores Pl 901 1 of 40 Listing Image for 106 Kaanapali Shores Pl 901 2 of 40 Listing Image for 106 Kaanapali Shores Pl 901 3 of 40 Listing Image for 106 Kaanapali Shores Pl 901 4 of 40 Listing Image for 106 Kaanapali Shores Pl 901 5 of 40 Listing Image for 106 Kaanapali Shores Pl 901 6 of 40 Listing Image for 106 Kaanapali Shores Pl 901 7 of 40 Listing Image for 106 Kaanapali Shores Pl 901 8 of 40 Listing Image for 106 Kaanapali Shores Pl 901 9 of 40 Listing Image for 106 Kaanapali Shores Pl 901 10 of 40 Listing Image for 106 Kaanapali Shores Pl 901 11 of 40 Listing Image for 106 Kaanapali Shores Pl 901 12 of 40 Listing Image for 106 Kaanapali Shores Pl 901 13 of 40 Listing Image for 106 Kaanapali Shores Pl 901 14 of 40 Listing Image for 106 Kaanapali Shores Pl 901 15 of 40 Listing Image for 106 Kaanapali Shores Pl 901 16 of 40 Listing Image for 106 Kaanapali Shores Pl 901 17 of 40 Listing Image for 106 Kaanapali Shores Pl 901 18 of 40 Listing Image for 106 Kaanapali Shores Pl 901 19 of 40 Listing Image for 106 Kaanapali Shores Pl 901 20 of 40 Listing Image for 106 Kaanapali Shores Pl 901 21 of 40 Listing Image for 106 Kaanapali Shores Pl 901 22 of 40 Listing Image for 106 Kaanapali Shores Pl 901 23 of 40 Listing Image for 106 Kaanapali Shores Pl 901 24 of 40 Listing Image for 106 Kaanapali Shores Pl 901 25 of 40 Listing Image for 106 Kaanapali Shores Pl 901 26 of 40 Listing Image for 106 Kaanapali Shores Pl 901 27 of 40 Listing Image for 106 Kaanapali Shores Pl 901 28 of 40 Listing Image for 106 Kaanapali Shores Pl 901 29 of 40 Listing Image for 106 Kaanapali Shores Pl 901 30 of 40 Listing Image for 106 Kaanapali Shores Pl 901 31 of 40 Listing Image for 106 Kaanapali Shores Pl 901 32 of 40 Listing Image for 106 Kaanapali Shores Pl 901 33 of 40 Listing Image for 106 Kaanapali Shores Pl 901 34 of 40 Listing Image for 106 Kaanapali Shores Pl 901 35 of 40 Listing Image for 106 Kaanapali Shores Pl 901 36 of 40 Listing Image for 106 Kaanapali Shores Pl 901 37 of 40 Listing Image for 106 Kaanapali Shores Pl 901 38 of 40 Listing Image for 106 Kaanapali Shores Pl 901 39 of 40 Listing Image for 106 Kaanapali Shores Pl 901 40 of 40

$1,199,000

Maui Kai 901

106 Kaanapali Shores Pl 901, Kaanapali

1 Bed 1 Bath 587 SqFt Residential MLS® # 405429

Days on Market: 540

Compass-W

Listing Image for 100 Kalelemuku Pl 1 of 50 Listing Image for 100 Kalelemuku Pl 2 of 50 Listing Image for 100 Kalelemuku Pl 3 of 50 Listing Image for 100 Kalelemuku Pl 4 of 50 Listing Image for 100 Kalelemuku Pl 5 of 50 Listing Image for 100 Kalelemuku Pl 6 of 50 Listing Image for 100 Kalelemuku Pl 7 of 50 Listing Image for 100 Kalelemuku Pl 8 of 50 Listing Image for 100 Kalelemuku Pl 9 of 50 Listing Image for 100 Kalelemuku Pl 10 of 50 Listing Image for 100 Kalelemuku Pl 11 of 50 Listing Image for 100 Kalelemuku Pl 12 of 50 Listing Image for 100 Kalelemuku Pl 13 of 50 Listing Image for 100 Kalelemuku Pl 14 of 50 Listing Image for 100 Kalelemuku Pl 15 of 50 Listing Image for 100 Kalelemuku Pl 16 of 50 Listing Image for 100 Kalelemuku Pl 17 of 50 Listing Image for 100 Kalelemuku Pl 18 of 50 Listing Image for 100 Kalelemuku Pl 19 of 50 Listing Image for 100 Kalelemuku Pl 20 of 50 Listing Image for 100 Kalelemuku Pl 21 of 50 Listing Image for 100 Kalelemuku Pl 22 of 50 Listing Image for 100 Kalelemuku Pl 23 of 50 Listing Image for 100 Kalelemuku Pl 24 of 50 Listing Image for 100 Kalelemuku Pl 25 of 50 Listing Image for 100 Kalelemuku Pl 26 of 50 Listing Image for 100 Kalelemuku Pl 27 of 50 Listing Image for 100 Kalelemuku Pl 28 of 50 Listing Image for 100 Kalelemuku Pl 29 of 50 Listing Image for 100 Kalelemuku Pl 30 of 50 Listing Image for 100 Kalelemuku Pl 31 of 50 Listing Image for 100 Kalelemuku Pl 32 of 50 Listing Image for 100 Kalelemuku Pl 33 of 50 Listing Image for 100 Kalelemuku Pl 34 of 50 Listing Image for 100 Kalelemuku Pl 35 of 50 Listing Image for 100 Kalelemuku Pl 36 of 50 Listing Image for 100 Kalelemuku Pl 37 of 50 Listing Image for 100 Kalelemuku Pl 38 of 50 Listing Image for 100 Kalelemuku Pl 39 of 50 Listing Image for 100 Kalelemuku Pl 40 of 50 Listing Image for 100 Kalelemuku Pl 41 of 50 Listing Image for 100 Kalelemuku Pl 42 of 50 Listing Image for 100 Kalelemuku Pl 43 of 50 Listing Image for 100 Kalelemuku Pl 44 of 50 Listing Image for 100 Kalelemuku Pl 45 of 50 Listing Image for 100 Kalelemuku Pl 46 of 50 Listing Image for 100 Kalelemuku Pl 47 of 50 Listing Image for 100 Kalelemuku Pl 48 of 50 Listing Image for 100 Kalelemuku Pl 49 of 50 Listing Image for 100 Kalelemuku Pl 50 of 50

$9,995,000

↓ $500,000

Kula I'o

100 Kalelemuku Pl, Kula/Ulupalakua/Kanaio

5 Beds 5 Baths 6,070 SqFt Residential MLS® # 406423

Days on Market: 443

Welcome Hawaii Properties Cell: 808-280-2480

Short Term Rental
Listing Image for 130 Kai Malina Pkwy Sr547 1 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 2 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 3 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 4 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 5 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 6 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 7 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 8 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 9 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 10 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 11 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 12 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 13 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 14 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 15 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 16 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 17 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 18 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 19 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 20 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 21 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 22 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 23 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 24 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 25 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 26 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 27 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 28 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 29 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 30 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 31 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 32 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 33 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 34 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 35 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 36 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 37 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 38 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 39 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 40 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 41 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 42 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 43 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 44 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 45 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 46 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 47 of 48 Listing Image for 130 Kai Malina Pkwy Sr547 48 of 48

$2,890,000

↓ $100,000

Honua Kai - Hoku Lani SR547

130 Kai Malina Pkwy Sr547, Kaanapali

2 Beds 2 Baths 1,100 SqFt Residential MLS® # 404372

Days on Market: 639

Keller Williams Realty Maui-L Cell: 808-870-2525

Listing Image for 116 Pulelehua St 1 1 of 39 Listing Image for 116 Pulelehua St 1 2 of 39 Listing Image for 116 Pulelehua St 1 3 of 39 Listing Image for 116 Pulelehua St 1 4 of 39 Listing Image for 116 Pulelehua St 1 5 of 39 Listing Image for 116 Pulelehua St 1 6 of 39 Listing Image for 116 Pulelehua St 1 7 of 39 Listing Image for 116 Pulelehua St 1 8 of 39 Listing Image for 116 Pulelehua St 1 9 of 39 Listing Image for 116 Pulelehua St 1 10 of 39 Listing Image for 116 Pulelehua St 1 11 of 39 Listing Image for 116 Pulelehua St 1 12 of 39 Listing Image for 116 Pulelehua St 1 13 of 39 Listing Image for 116 Pulelehua St 1 14 of 39 Listing Image for 116 Pulelehua St 1 15 of 39 Listing Image for 116 Pulelehua St 1 16 of 39 Listing Image for 116 Pulelehua St 1 17 of 39 Listing Image for 116 Pulelehua St 1 18 of 39 Listing Image for 116 Pulelehua St 1 19 of 39 Listing Image for 116 Pulelehua St 1 20 of 39 Listing Image for 116 Pulelehua St 1 21 of 39 Listing Image for 116 Pulelehua St 1 22 of 39 Listing Image for 116 Pulelehua St 1 23 of 39 Listing Image for 116 Pulelehua St 1 24 of 39 Listing Image for 116 Pulelehua St 1 25 of 39 Listing Image for 116 Pulelehua St 1 26 of 39 Listing Image for 116 Pulelehua St 1 27 of 39 Listing Image for 116 Pulelehua St 1 28 of 39 Listing Image for 116 Pulelehua St 1 29 of 39 Listing Image for 116 Pulelehua St 1 30 of 39 Listing Image for 116 Pulelehua St 1 31 of 39 Listing Image for 116 Pulelehua St 1 32 of 39 Listing Image for 116 Pulelehua St 1 33 of 39 Listing Image for 116 Pulelehua St 1 34 of 39 Listing Image for 116 Pulelehua St 1 35 of 39 Listing Image for 116 Pulelehua St 1 36 of 39 Listing Image for 116 Pulelehua St 1 37 of 39 Listing Image for 116 Pulelehua St 1 38 of 39 Listing Image for 116 Pulelehua St 1 39 of 39

$4,650,000

↓ $300,000

Pineapple Hill Estates

116 Pulelehua St 1, Kapalua

4 Beds 4.5 Baths 4,081 SqFt Residential MLS® # 406659

Days on Market: 416

Keller Williams Realty Maui-L Cell: 808-870-7736

View 7 More Listings

Apply for a Home Equity Loan

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

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

Recent Sales on Maui

Sold
Closed: 08/31/2026
Listing Image for 210 E Panana Pl 1 of 41 Listing Image for 210 E Panana Pl 2 of 41 Listing Image for 210 E Panana Pl 3 of 41 Listing Image for 210 E Panana Pl 4 of 41 Listing Image for 210 E Panana Pl 5 of 41 Listing Image for 210 E Panana Pl 6 of 41 Listing Image for 210 E Panana Pl 7 of 41 Listing Image for 210 E Panana Pl 8 of 41 Listing Image for 210 E Panana Pl 9 of 41 Listing Image for 210 E Panana Pl 10 of 41 Listing Image for 210 E Panana Pl 11 of 41 Listing Image for 210 E Panana Pl 12 of 41 Listing Image for 210 E Panana Pl 13 of 41 Listing Image for 210 E Panana Pl 14 of 41 Listing Image for 210 E Panana Pl 15 of 41 Listing Image for 210 E Panana Pl 16 of 41 Listing Image for 210 E Panana Pl 17 of 41 Listing Image for 210 E Panana Pl 18 of 41 Listing Image for 210 E Panana Pl 19 of 41 Listing Image for 210 E Panana Pl 20 of 41 Listing Image for 210 E Panana Pl 21 of 41 Listing Image for 210 E Panana Pl 22 of 41 Listing Image for 210 E Panana Pl 23 of 41 Listing Image for 210 E Panana Pl 24 of 41 Listing Image for 210 E Panana Pl 25 of 41 Listing Image for 210 E Panana Pl 26 of 41 Listing Image for 210 E Panana Pl 27 of 41 Listing Image for 210 E Panana Pl 28 of 41 Listing Image for 210 E Panana Pl 29 of 41 Listing Image for 210 E Panana Pl 30 of 41 Listing Image for 210 E Panana Pl 31 of 41 Listing Image for 210 E Panana Pl 32 of 41 Listing Image for 210 E Panana Pl 33 of 41 Listing Image for 210 E Panana Pl 34 of 41 Listing Image for 210 E Panana Pl 35 of 41 Listing Image for 210 E Panana Pl 36 of 41 Listing Image for 210 E Panana Pl 37 of 41 Listing Image for 210 E Panana Pl 38 of 41 Listing Image for 210 E Panana Pl 39 of 41 Listing Image for 210 E Panana Pl 40 of 41 Listing Image for 210 E Panana Pl 41 of 41

$2,900,000

↓ $250,000

Wailea Kialoa

210 E Panana Pl, Wailea/Makena

4 Beds 3 Baths 3,465 SqFt Residential MLS® # 407000 Date Sold: August 31, 2026
Sold
Closed: 10/23/2025
Listing Image for 788 Kihau Pl 1 of 26 Listing Image for 788 Kihau Pl 2 of 26 Listing Image for 788 Kihau Pl 3 of 26 Listing Image for 788 Kihau Pl 4 of 26 Listing Image for 788 Kihau Pl 5 of 26 Listing Image for 788 Kihau Pl 6 of 26 Listing Image for 788 Kihau Pl 7 of 26 Listing Image for 788 Kihau Pl 8 of 26 Listing Image for 788 Kihau Pl 9 of 26 Listing Image for 788 Kihau Pl 10 of 26 Listing Image for 788 Kihau Pl 11 of 26 Listing Image for 788 Kihau Pl 12 of 26 Listing Image for 788 Kihau Pl 13 of 26 Listing Image for 788 Kihau Pl 14 of 26 Listing Image for 788 Kihau Pl 15 of 26 Listing Image for 788 Kihau Pl 16 of 26 Listing Image for 788 Kihau Pl 17 of 26 Listing Image for 788 Kihau Pl 18 of 26 Listing Image for 788 Kihau Pl 19 of 26 Listing Image for 788 Kihau Pl 20 of 26 Listing Image for 788 Kihau Pl 21 of 26 Listing Image for 788 Kihau Pl 22 of 26 Listing Image for 788 Kihau Pl 23 of 26 Listing Image for 788 Kihau Pl 24 of 26 Listing Image for 788 Kihau Pl 25 of 26 Listing Image for 788 Kihau Pl 26 of 26

$773,000

Cooper Park Tract

788 Kihau Pl, Haiku

2 Beds 1.5 Baths 696 SqFt Residential MLS® # 407029 Date Sold: October 23, 2025
Sold
Closed: 10/24/2025
Listing Image for 151 Hoopili Akau St 1 of 50 Listing Image for 151 Hoopili Akau St 2 of 50 Listing Image for 151 Hoopili Akau St 3 of 50 Listing Image for 151 Hoopili Akau St 4 of 50 Listing Image for 151 Hoopili Akau St 5 of 50 Listing Image for 151 Hoopili Akau St 6 of 50 Listing Image for 151 Hoopili Akau St 7 of 50 Listing Image for 151 Hoopili Akau St 8 of 50 Listing Image for 151 Hoopili Akau St 9 of 50 Listing Image for 151 Hoopili Akau St 10 of 50 Listing Image for 151 Hoopili Akau St 11 of 50 Listing Image for 151 Hoopili Akau St 12 of 50 Listing Image for 151 Hoopili Akau St 13 of 50 Listing Image for 151 Hoopili Akau St 14 of 50 Listing Image for 151 Hoopili Akau St 15 of 50 Listing Image for 151 Hoopili Akau St 16 of 50 Listing Image for 151 Hoopili Akau St 17 of 50 Listing Image for 151 Hoopili Akau St 18 of 50 Listing Image for 151 Hoopili Akau St 19 of 50 Listing Image for 151 Hoopili Akau St 20 of 50 Listing Image for 151 Hoopili Akau St 21 of 50 Listing Image for 151 Hoopili Akau St 22 of 50 Listing Image for 151 Hoopili Akau St 23 of 50 Listing Image for 151 Hoopili Akau St 24 of 50 Listing Image for 151 Hoopili Akau St 25 of 50 Listing Image for 151 Hoopili Akau St 26 of 50 Listing Image for 151 Hoopili Akau St 27 of 50 Listing Image for 151 Hoopili Akau St 28 of 50 Listing Image for 151 Hoopili Akau St 29 of 50 Listing Image for 151 Hoopili Akau St 30 of 50 Listing Image for 151 Hoopili Akau St 31 of 50 Listing Image for 151 Hoopili Akau St 32 of 50 Listing Image for 151 Hoopili Akau St 33 of 50 Listing Image for 151 Hoopili Akau St 34 of 50 Listing Image for 151 Hoopili Akau St 35 of 50 Listing Image for 151 Hoopili Akau St 36 of 50 Listing Image for 151 Hoopili Akau St 37 of 50 Listing Image for 151 Hoopili Akau St 38 of 50 Listing Image for 151 Hoopili Akau St 39 of 50 Listing Image for 151 Hoopili Akau St 40 of 50 Listing Image for 151 Hoopili Akau St 41 of 50 Listing Image for 151 Hoopili Akau St 42 of 50 Listing Image for 151 Hoopili Akau St 43 of 50 Listing Image for 151 Hoopili Akau St 44 of 50 Listing Image for 151 Hoopili Akau St 45 of 50 Listing Image for 151 Hoopili Akau St 46 of 50 Listing Image for 151 Hoopili Akau St 47 of 50 Listing Image for 151 Hoopili Akau St 48 of 50 Listing Image for 151 Hoopili Akau St 49 of 50 Listing Image for 151 Hoopili Akau St 50 of 50

$1,195,000

Kihei

151 Hoopili Akau St, Kihei

3 Beds 2 Baths 1,478 SqFt Residential MLS® # 406925 Date Sold: October 24, 2025
Sold
Closed: 11/14/2025
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$1,325,000

↓ $100,000

Kahului

382 Naholo Cir, Kahului

3 Beds 3 Baths 1,969 SqFt Residential MLS® # 406975 Date Sold: November 14, 2025
Sold
Closed: 11/14/2025
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$1,600,000

Kula/Ulupalakua/Kanaio

8197 Kula Hwy, Kula/Ulupalakua/Kanaio

2 Beds 2 Baths 1,340 SqFt Residential MLS® # 406938 Date Sold: November 14, 2025
Sold
Closed: 03/06/2026
Listing Image for 1791 Piihana Rd 1 of 47 Listing Image for 1791 Piihana Rd 2 of 47 Listing Image for 1791 Piihana Rd 3 of 47 Listing Image for 1791 Piihana Rd 4 of 47 Listing Image for 1791 Piihana Rd 5 of 47 Listing Image for 1791 Piihana Rd 6 of 47 Listing Image for 1791 Piihana Rd 7 of 47 Listing Image for 1791 Piihana Rd 8 of 47 Listing Image for 1791 Piihana Rd 9 of 47 Listing Image for 1791 Piihana Rd 10 of 47 Listing Image for 1791 Piihana Rd 11 of 47 Listing Image for 1791 Piihana Rd 12 of 47 Listing Image for 1791 Piihana Rd 13 of 47 Listing Image for 1791 Piihana Rd 14 of 47 Listing Image for 1791 Piihana Rd 15 of 47 Listing Image for 1791 Piihana Rd 16 of 47 Listing Image for 1791 Piihana Rd 17 of 47 Listing Image for 1791 Piihana Rd 18 of 47 Listing Image for 1791 Piihana Rd 19 of 47 Listing Image for 1791 Piihana Rd 20 of 47 Listing Image for 1791 Piihana Rd 21 of 47 Listing Image for 1791 Piihana Rd 22 of 47 Listing Image for 1791 Piihana Rd 23 of 47 Listing Image for 1791 Piihana Rd 24 of 47 Listing Image for 1791 Piihana Rd 25 of 47 Listing Image for 1791 Piihana Rd 26 of 47 Listing Image for 1791 Piihana Rd 27 of 47 Listing Image for 1791 Piihana Rd 28 of 47 Listing Image for 1791 Piihana Rd 29 of 47 Listing Image for 1791 Piihana Rd 30 of 47 Listing Image for 1791 Piihana Rd 31 of 47 Listing Image for 1791 Piihana Rd 32 of 47 Listing Image for 1791 Piihana Rd 33 of 47 Listing Image for 1791 Piihana Rd 34 of 47 Listing Image for 1791 Piihana Rd 35 of 47 Listing Image for 1791 Piihana Rd 36 of 47 Listing Image for 1791 Piihana Rd 37 of 47 Listing Image for 1791 Piihana Rd 38 of 47 Listing Image for 1791 Piihana Rd 39 of 47 Listing Image for 1791 Piihana Rd 40 of 47 Listing Image for 1791 Piihana Rd 41 of 47 Listing Image for 1791 Piihana Rd 42 of 47 Listing Image for 1791 Piihana Rd 43 of 47 Listing Image for 1791 Piihana Rd 44 of 47 Listing Image for 1791 Piihana Rd 45 of 47 Listing Image for 1791 Piihana Rd 46 of 47 Listing Image for 1791 Piihana Rd 47 of 47

$850,000

↓ $85,000

Wailuku

1791 Piihana Rd, Wailuku

4 Beds 2 Baths 2,630 SqFt Residential MLS® # 406992 Date Sold: March 6, 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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