Strategies of Buying and Selling Simultaneously

Buying and Selling a Home at the Same Time

You may have found yourself in a position where you would like to buy one property while simultaneously selling another property. While doing this does present some unique challenges, it's completely possible to pull this off with the proper strategy and some degree of flexibility

The reasons and strategies for wanting to buy and sell simultaneously will differ from a primary homeowner looking to relocate to an investor seeking to execute a 1031 exchange to avoid capital gains taxes. In either instance, it's important to have a sound strategy and understand what the undertaking will involve. 

Selling A Primary Residence While Buying Another

There are several different ways to do this and how you do it will depend on your financial philosophies. There isn't necessarily a right and wrong way to approach this, some consider selling their home first the priority and then are willing to rent for a period of 6 months while they find the perfect replacement. This is usually the lowest stress avenue.

Some will be intent on executing the sale and purchase in such a way that both properties close in close succession to remove the extra step of renting. Money is a huge consideration for this move, particularly when financing is involved. In many instances, sellers will need the equity from the sale of their home to fund the down payment on the purchase of the second. 

If Financing is Necessary, Get Prequalified for a New Mortgage First

Before you get serious about selling your home, you should thoroughly research the possibility of buying a new primary residence. The Maui housing market can change rapidly at times, and the lending environment is changing as well. When you get prequalified with a local Maui lender, you can better determine your price range for a new home.

You can get accurate information about the interest rates available for your credit score and other qualifications. In addition, you can confirm that you can afford the loan payment for the size and quality of the home you are interested in.

Discuss Your Plans with a Real Estate Agent

After learning about your prequalification status, consulting with real estate agents in Maui is the next step. An experienced Maui real estate agent can help you determine how long your home may reasonably remain on the market.

In addition, you can get details on a realistic sales price. By analyzing the sales price in combination with closing costs and the current mortgage payoff balance, you can determine the sales proceeds that you have available for a down payment on your new home purchase. 

Newest Maui Properties For Sale

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Short Term Rental
Listing Image for 130 Kai Malina Pkwy Nr609 1 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 2 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 3 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 4 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 5 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 6 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 7 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 8 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 9 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 10 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 11 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 12 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 13 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 14 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 15 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 16 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 17 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 18 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 19 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 20 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 21 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 22 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 23 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 24 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 25 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 26 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 27 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 28 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 29 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 30 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 31 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 32 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 33 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 34 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 35 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 36 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 37 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 38 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 39 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 40 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 41 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 42 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 43 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 44 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 45 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 46 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 47 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 48 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 49 of 50 Listing Image for 130 Kai Malina Pkwy Nr609 50 of 50

$2,590,000

Honua Kai - Konea NR609

130 Kai Malina Pkwy Nr609, Kaanapali

2 Beds 2 Baths 1,315 SqFt Residential MLS® # 406602

Days on Market: 420

Coldwell Banker Island Prop-KP Cell: 808-283-3067

In Escrow
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$1,099,000

Kua'aina Mauka

136 Tam Yau Pl 12h, Makawao/Olinda/Haliimaile

3 Beds 2.5 Baths 1,674 SqFt Residential MLS® # 410426

Days on Market: 41

Island Sotheby's International Realty(M) Cell: 808-205-5088

In Escrow
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$1,249,000

Village at Mahinahina

30 Haku Hale Pl, Napili/Kahana/Honokowai

3 Beds 2 Baths 1,372 SqFt Residential MLS® # 410425

Days on Market: 42

Coldwell Banker Island Prop-KP Cell: 808-868-8673

In Escrow
Listing Image for 4345 Waha Pl 1 of 48 Listing Image for 4345 Waha Pl 2 of 48 Listing Image for 4345 Waha Pl 3 of 48 Listing Image for 4345 Waha Pl 4 of 48 Listing Image for 4345 Waha Pl 5 of 48 Listing Image for 4345 Waha Pl 6 of 48 Listing Image for 4345 Waha Pl 7 of 48 Listing Image for 4345 Waha Pl 8 of 48 Listing Image for 4345 Waha Pl 9 of 48 Listing Image for 4345 Waha Pl 10 of 48 Listing Image for 4345 Waha Pl 11 of 48 Listing Image for 4345 Waha Pl 12 of 48 Listing Image for 4345 Waha Pl 13 of 48 Listing Image for 4345 Waha Pl 14 of 48 Listing Image for 4345 Waha Pl 15 of 48 Listing Image for 4345 Waha Pl 16 of 48 Listing Image for 4345 Waha Pl 17 of 48 Listing Image for 4345 Waha Pl 18 of 48 Listing Image for 4345 Waha Pl 19 of 48 Listing Image for 4345 Waha Pl 20 of 48 Listing Image for 4345 Waha Pl 21 of 48 Listing Image for 4345 Waha Pl 22 of 48 Listing Image for 4345 Waha Pl 23 of 48 Listing Image for 4345 Waha Pl 24 of 48 Listing Image for 4345 Waha Pl 25 of 48 Listing Image for 4345 Waha Pl 26 of 48 Listing Image for 4345 Waha Pl 27 of 48 Listing Image for 4345 Waha Pl 28 of 48 Listing Image for 4345 Waha Pl 29 of 48 Listing Image for 4345 Waha Pl 30 of 48 Listing Image for 4345 Waha Pl 31 of 48 Listing Image for 4345 Waha Pl 32 of 48 Listing Image for 4345 Waha Pl 33 of 48 Listing Image for 4345 Waha Pl 34 of 48 Listing Image for 4345 Waha Pl 35 of 48 Listing Image for 4345 Waha Pl 36 of 48 Listing Image for 4345 Waha Pl 37 of 48 Listing Image for 4345 Waha Pl 38 of 48 Listing Image for 4345 Waha Pl 39 of 48 Listing Image for 4345 Waha Pl 40 of 48 Listing Image for 4345 Waha Pl 41 of 48 Listing Image for 4345 Waha Pl 42 of 48 Listing Image for 4345 Waha Pl 43 of 48 Listing Image for 4345 Waha Pl 44 of 48 Listing Image for 4345 Waha Pl 45 of 48 Listing Image for 4345 Waha Pl 46 of 48 Listing Image for 4345 Waha Pl 47 of 48 Listing Image for 4345 Waha Pl 48 of 48

$2,095,000

Haiku

4345 Waha Pl, Haiku

3 Beds 3 Baths 2,184 SqFt Residential MLS® # 410263

Days on Market: 61

Coldwell Banker Island Prop(S) Cell: 808-870-4899

Listing Image for 18 Upena Ln E-102 1 of 39 Listing Image for 18 Upena Ln E-102 2 of 39 Listing Image for 18 Upena Ln E-102 3 of 39 Listing Image for 18 Upena Ln E-102 4 of 39 Listing Image for 18 Upena Ln E-102 5 of 39 Listing Image for 18 Upena Ln E-102 6 of 39 Listing Image for 18 Upena Ln E-102 7 of 39 Listing Image for 18 Upena Ln E-102 8 of 39 Listing Image for 18 Upena Ln E-102 9 of 39 Listing Image for 18 Upena Ln E-102 10 of 39 Listing Image for 18 Upena Ln E-102 11 of 39 Listing Image for 18 Upena Ln E-102 12 of 39 Listing Image for 18 Upena Ln E-102 13 of 39 Listing Image for 18 Upena Ln E-102 14 of 39 Listing Image for 18 Upena Ln E-102 15 of 39 Listing Image for 18 Upena Ln E-102 16 of 39 Listing Image for 18 Upena Ln E-102 17 of 39 Listing Image for 18 Upena Ln E-102 18 of 39 Listing Image for 18 Upena Ln E-102 19 of 39 Listing Image for 18 Upena Ln E-102 20 of 39 Listing Image for 18 Upena Ln E-102 21 of 39 Listing Image for 18 Upena Ln E-102 22 of 39 Listing Image for 18 Upena Ln E-102 23 of 39 Listing Image for 18 Upena Ln E-102 24 of 39 Listing Image for 18 Upena Ln E-102 25 of 39 Listing Image for 18 Upena Ln E-102 26 of 39 Listing Image for 18 Upena Ln E-102 27 of 39 Listing Image for 18 Upena Ln E-102 28 of 39 Listing Image for 18 Upena Ln E-102 29 of 39 Listing Image for 18 Upena Ln E-102 30 of 39 Listing Image for 18 Upena Ln E-102 31 of 39 Listing Image for 18 Upena Ln E-102 32 of 39 Listing Image for 18 Upena Ln E-102 33 of 39 Listing Image for 18 Upena Ln E-102 34 of 39 Listing Image for 18 Upena Ln E-102 35 of 39 Listing Image for 18 Upena Ln E-102 36 of 39 Listing Image for 18 Upena Ln E-102 37 of 39 Listing Image for 18 Upena Ln E-102 38 of 39 Listing Image for 18 Upena Ln E-102 39 of 39

$1,110,000

↓ $15,000

Ke Alii Ocean Villas E-102

18 Upena Ln E-102, Kihei

2 Beds 2 Baths 1,233 SqFt Residential MLS® # 405981

Days on Market: 487

Pacific Image Properties sharissac@gmail.com

Short Term Rental
Listing Image for 940 S Kihei Rd D305 1 of 50 Listing Image for 940 S Kihei Rd D305 2 of 50 Listing Image for 940 S Kihei Rd D305 3 of 50 Listing Image for 940 S Kihei Rd D305 4 of 50 Listing Image for 940 S Kihei Rd D305 5 of 50 Listing Image for 940 S Kihei Rd D305 6 of 50 Listing Image for 940 S Kihei Rd D305 7 of 50 Listing Image for 940 S Kihei Rd D305 8 of 50 Listing Image for 940 S Kihei Rd D305 9 of 50 Listing Image for 940 S Kihei Rd D305 10 of 50 Listing Image for 940 S Kihei Rd D305 11 of 50 Listing Image for 940 S Kihei Rd D305 12 of 50 Listing Image for 940 S Kihei Rd D305 13 of 50 Listing Image for 940 S Kihei Rd D305 14 of 50 Listing Image for 940 S Kihei Rd D305 15 of 50 Listing Image for 940 S Kihei Rd D305 16 of 50 Listing Image for 940 S Kihei Rd D305 17 of 50 Listing Image for 940 S Kihei Rd D305 18 of 50 Listing Image for 940 S Kihei Rd D305 19 of 50 Listing Image for 940 S Kihei Rd D305 20 of 50 Listing Image for 940 S Kihei Rd D305 21 of 50 Listing Image for 940 S Kihei Rd D305 22 of 50 Listing Image for 940 S Kihei Rd D305 23 of 50 Listing Image for 940 S Kihei Rd D305 24 of 50 Listing Image for 940 S Kihei Rd D305 25 of 50 Listing Image for 940 S Kihei Rd D305 26 of 50 Listing Image for 940 S Kihei Rd D305 27 of 50 Listing Image for 940 S Kihei Rd D305 28 of 50 Listing Image for 940 S Kihei Rd D305 29 of 50 Listing Image for 940 S Kihei Rd D305 30 of 50 Listing Image for 940 S Kihei Rd D305 31 of 50 Listing Image for 940 S Kihei Rd D305 32 of 50 Listing Image for 940 S Kihei Rd D305 33 of 50 Listing Image for 940 S Kihei Rd D305 34 of 50 Listing Image for 940 S Kihei Rd D305 35 of 50 Listing Image for 940 S Kihei Rd D305 36 of 50 Listing Image for 940 S Kihei Rd D305 37 of 50 Listing Image for 940 S Kihei Rd D305 38 of 50 Listing Image for 940 S Kihei Rd D305 39 of 50 Listing Image for 940 S Kihei Rd D305 40 of 50 Listing Image for 940 S Kihei Rd D305 41 of 50 Listing Image for 940 S Kihei Rd D305 42 of 50 Listing Image for 940 S Kihei Rd D305 43 of 50 Listing Image for 940 S Kihei Rd D305 44 of 50 Listing Image for 940 S Kihei Rd D305 45 of 50 Listing Image for 940 S Kihei Rd D305 46 of 50 Listing Image for 940 S Kihei Rd D305 47 of 50 Listing Image for 940 S Kihei Rd D305 48 of 50 Listing Image for 940 S Kihei Rd D305 49 of 50 Listing Image for 940 S Kihei Rd D305 50 of 50

$995,000

Luana Kai D305

940 S Kihei Rd D305, Kihei

2 Beds 2 Baths 963 SqFt Residential MLS® # 410422

Days on Market: 42

Coldwell Banker Island Prop-Ku 808-281-8083

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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: 06/03/2026
Listing Image for 347 Kualono Pl 1 of 50 Listing Image for 347 Kualono Pl 2 of 50 Listing Image for 347 Kualono Pl 3 of 50 Listing Image for 347 Kualono Pl 4 of 50 Listing Image for 347 Kualono Pl 5 of 50 Listing Image for 347 Kualono Pl 6 of 50 Listing Image for 347 Kualono Pl 7 of 50 Listing Image for 347 Kualono Pl 8 of 50 Listing Image for 347 Kualono Pl 9 of 50 Listing Image for 347 Kualono Pl 10 of 50 Listing Image for 347 Kualono Pl 11 of 50 Listing Image for 347 Kualono Pl 12 of 50 Listing Image for 347 Kualono Pl 13 of 50 Listing Image for 347 Kualono Pl 14 of 50 Listing Image for 347 Kualono Pl 15 of 50 Listing Image for 347 Kualono Pl 16 of 50 Listing Image for 347 Kualono Pl 17 of 50 Listing Image for 347 Kualono Pl 18 of 50 Listing Image for 347 Kualono Pl 19 of 50 Listing Image for 347 Kualono Pl 20 of 50 Listing Image for 347 Kualono Pl 21 of 50 Listing Image for 347 Kualono Pl 22 of 50 Listing Image for 347 Kualono Pl 23 of 50 Listing Image for 347 Kualono Pl 24 of 50 Listing Image for 347 Kualono Pl 25 of 50 Listing Image for 347 Kualono Pl 26 of 50 Listing Image for 347 Kualono Pl 27 of 50 Listing Image for 347 Kualono Pl 28 of 50 Listing Image for 347 Kualono Pl 29 of 50 Listing Image for 347 Kualono Pl 30 of 50 Listing Image for 347 Kualono Pl 31 of 50 Listing Image for 347 Kualono Pl 32 of 50 Listing Image for 347 Kualono Pl 33 of 50 Listing Image for 347 Kualono Pl 34 of 50 Listing Image for 347 Kualono Pl 35 of 50 Listing Image for 347 Kualono Pl 36 of 50 Listing Image for 347 Kualono Pl 37 of 50 Listing Image for 347 Kualono Pl 38 of 50 Listing Image for 347 Kualono Pl 39 of 50 Listing Image for 347 Kualono Pl 40 of 50 Listing Image for 347 Kualono Pl 41 of 50 Listing Image for 347 Kualono Pl 42 of 50 Listing Image for 347 Kualono Pl 43 of 50 Listing Image for 347 Kualono Pl 44 of 50 Listing Image for 347 Kualono Pl 45 of 50 Listing Image for 347 Kualono Pl 46 of 50 Listing Image for 347 Kualono Pl 47 of 50 Listing Image for 347 Kualono Pl 48 of 50 Listing Image for 347 Kualono Pl 49 of 50 Listing Image for 347 Kualono Pl 50 of 50

$3,500,000

Wailea Pualani

347 Kualono Pl, Wailea/Makena

4 Beds 3.5 Baths 3,007 SqFt Residential MLS® # 409326 Date Sold: June 3, 2026
Sold
Closed: 08/20/2026
Listing Image for 2661 Kekaa Dr L-205 1 of 45 Listing Image for 2661 Kekaa Dr L-205 2 of 45 Listing Image for 2661 Kekaa Dr L-205 3 of 45 Listing Image for 2661 Kekaa Dr L-205 4 of 45 Listing Image for 2661 Kekaa Dr L-205 5 of 45 Listing Image for 2661 Kekaa Dr L-205 6 of 45 Listing Image for 2661 Kekaa Dr L-205 7 of 45 Listing Image for 2661 Kekaa Dr L-205 8 of 45 Listing Image for 2661 Kekaa Dr L-205 9 of 45 Listing Image for 2661 Kekaa Dr L-205 10 of 45 Listing Image for 2661 Kekaa Dr L-205 11 of 45 Listing Image for 2661 Kekaa Dr L-205 12 of 45 Listing Image for 2661 Kekaa Dr L-205 13 of 45 Listing Image for 2661 Kekaa Dr L-205 14 of 45 Listing Image for 2661 Kekaa Dr L-205 15 of 45 Listing Image for 2661 Kekaa Dr L-205 16 of 45 Listing Image for 2661 Kekaa Dr L-205 17 of 45 Listing Image for 2661 Kekaa Dr L-205 18 of 45 Listing Image for 2661 Kekaa Dr L-205 19 of 45 Listing Image for 2661 Kekaa Dr L-205 20 of 45 Listing Image for 2661 Kekaa Dr L-205 21 of 45 Listing Image for 2661 Kekaa Dr L-205 22 of 45 Listing Image for 2661 Kekaa Dr L-205 23 of 45 Listing Image for 2661 Kekaa Dr L-205 24 of 45 Listing Image for 2661 Kekaa Dr L-205 25 of 45 Listing Image for 2661 Kekaa Dr L-205 26 of 45 Listing Image for 2661 Kekaa Dr L-205 27 of 45 Listing Image for 2661 Kekaa Dr L-205 28 of 45 Listing Image for 2661 Kekaa Dr L-205 29 of 45 Listing Image for 2661 Kekaa Dr L-205 30 of 45 Listing Image for 2661 Kekaa Dr L-205 31 of 45 Listing Image for 2661 Kekaa Dr L-205 32 of 45 Listing Image for 2661 Kekaa Dr L-205 33 of 45 Listing Image for 2661 Kekaa Dr L-205 34 of 45 Listing Image for 2661 Kekaa Dr L-205 35 of 45 Listing Image for 2661 Kekaa Dr L-205 36 of 45 Listing Image for 2661 Kekaa Dr L-205 37 of 45 Listing Image for 2661 Kekaa Dr L-205 38 of 45 Listing Image for 2661 Kekaa Dr L-205 39 of 45 Listing Image for 2661 Kekaa Dr L-205 40 of 45 Listing Image for 2661 Kekaa Dr L-205 41 of 45 Listing Image for 2661 Kekaa Dr L-205 42 of 45 Listing Image for 2661 Kekaa Dr L-205 43 of 45 Listing Image for 2661 Kekaa Dr L-205 44 of 45 Listing Image for 2661 Kekaa Dr L-205 45 of 45

$925,000

↓ $235,000

Maui Eldorado L-205

2661 Kekaa Dr L-205, Kaanapali

2 Beds 2 Baths 1,440 SqFt Residential MLS® # 409316 Date Sold: August 20, 2026
Sold
Closed: 07/31/2026
Listing Image for 63 Hoolei Cir B5 1 of 48 Listing Image for 63 Hoolei Cir B5 2 of 48 Listing Image for 63 Hoolei Cir B5 3 of 48 Listing Image for 63 Hoolei Cir B5 4 of 48 Listing Image for 63 Hoolei Cir B5 5 of 48 Listing Image for 63 Hoolei Cir B5 6 of 48 Listing Image for 63 Hoolei Cir B5 7 of 48 Listing Image for 63 Hoolei Cir B5 8 of 48 Listing Image for 63 Hoolei Cir B5 9 of 48 Listing Image for 63 Hoolei Cir B5 10 of 48 Listing Image for 63 Hoolei Cir B5 11 of 48 Listing Image for 63 Hoolei Cir B5 12 of 48 Listing Image for 63 Hoolei Cir B5 13 of 48 Listing Image for 63 Hoolei Cir B5 14 of 48 Listing Image for 63 Hoolei Cir B5 15 of 48 Listing Image for 63 Hoolei Cir B5 16 of 48 Listing Image for 63 Hoolei Cir B5 17 of 48 Listing Image for 63 Hoolei Cir B5 18 of 48 Listing Image for 63 Hoolei Cir B5 19 of 48 Listing Image for 63 Hoolei Cir B5 20 of 48 Listing Image for 63 Hoolei Cir B5 21 of 48 Listing Image for 63 Hoolei Cir B5 22 of 48 Listing Image for 63 Hoolei Cir B5 23 of 48 Listing Image for 63 Hoolei Cir B5 24 of 48 Listing Image for 63 Hoolei Cir B5 25 of 48 Listing Image for 63 Hoolei Cir B5 26 of 48 Listing Image for 63 Hoolei Cir B5 27 of 48 Listing Image for 63 Hoolei Cir B5 28 of 48 Listing Image for 63 Hoolei Cir B5 29 of 48 Listing Image for 63 Hoolei Cir B5 30 of 48 Listing Image for 63 Hoolei Cir B5 31 of 48 Listing Image for 63 Hoolei Cir B5 32 of 48 Listing Image for 63 Hoolei Cir B5 33 of 48 Listing Image for 63 Hoolei Cir B5 34 of 48 Listing Image for 63 Hoolei Cir B5 35 of 48 Listing Image for 63 Hoolei Cir B5 36 of 48 Listing Image for 63 Hoolei Cir B5 37 of 48 Listing Image for 63 Hoolei Cir B5 38 of 48 Listing Image for 63 Hoolei Cir B5 39 of 48 Listing Image for 63 Hoolei Cir B5 40 of 48 Listing Image for 63 Hoolei Cir B5 41 of 48 Listing Image for 63 Hoolei Cir B5 42 of 48 Listing Image for 63 Hoolei Cir B5 43 of 48 Listing Image for 63 Hoolei Cir B5 44 of 48 Listing Image for 63 Hoolei Cir B5 45 of 48 Listing Image for 63 Hoolei Cir B5 46 of 48 Listing Image for 63 Hoolei Cir B5 47 of 48 Listing Image for 63 Hoolei Cir B5 48 of 48

$4,500,000

Hoolei B5

63 Hoolei Cir B5, Wailea/Makena

3 Beds 3.5 Baths 2,426 SqFt Residential MLS® # 409315 Date Sold: July 31, 2026
Sold
Closed: 07/27/2026
Listing Image for 145 N Kihei Rd 417 1 of 45 Listing Image for 145 N Kihei Rd 417 2 of 45 Listing Image for 145 N Kihei Rd 417 3 of 45 Listing Image for 145 N Kihei Rd 417 4 of 45 Listing Image for 145 N Kihei Rd 417 5 of 45 Listing Image for 145 N Kihei Rd 417 6 of 45 Listing Image for 145 N Kihei Rd 417 7 of 45 Listing Image for 145 N Kihei Rd 417 8 of 45 Listing Image for 145 N Kihei Rd 417 9 of 45 Listing Image for 145 N Kihei Rd 417 10 of 45 Listing Image for 145 N Kihei Rd 417 11 of 45 Listing Image for 145 N Kihei Rd 417 12 of 45 Listing Image for 145 N Kihei Rd 417 13 of 45 Listing Image for 145 N Kihei Rd 417 14 of 45 Listing Image for 145 N Kihei Rd 417 15 of 45 Listing Image for 145 N Kihei Rd 417 16 of 45 Listing Image for 145 N Kihei Rd 417 17 of 45 Listing Image for 145 N Kihei Rd 417 18 of 45 Listing Image for 145 N Kihei Rd 417 19 of 45 Listing Image for 145 N Kihei Rd 417 20 of 45 Listing Image for 145 N Kihei Rd 417 21 of 45 Listing Image for 145 N Kihei Rd 417 22 of 45 Listing Image for 145 N Kihei Rd 417 23 of 45 Listing Image for 145 N Kihei Rd 417 24 of 45 Listing Image for 145 N Kihei Rd 417 25 of 45 Listing Image for 145 N Kihei Rd 417 26 of 45 Listing Image for 145 N Kihei Rd 417 27 of 45 Listing Image for 145 N Kihei Rd 417 28 of 45 Listing Image for 145 N Kihei Rd 417 29 of 45 Listing Image for 145 N Kihei Rd 417 30 of 45 Listing Image for 145 N Kihei Rd 417 31 of 45 Listing Image for 145 N Kihei Rd 417 32 of 45 Listing Image for 145 N Kihei Rd 417 33 of 45 Listing Image for 145 N Kihei Rd 417 34 of 45 Listing Image for 145 N Kihei Rd 417 35 of 45 Listing Image for 145 N Kihei Rd 417 36 of 45 Listing Image for 145 N Kihei Rd 417 37 of 45 Listing Image for 145 N Kihei Rd 417 38 of 45 Listing Image for 145 N Kihei Rd 417 39 of 45 Listing Image for 145 N Kihei Rd 417 40 of 45 Listing Image for 145 N Kihei Rd 417 41 of 45 Listing Image for 145 N Kihei Rd 417 42 of 45 Listing Image for 145 N Kihei Rd 417 43 of 45 Listing Image for 145 N Kihei Rd 417 44 of 45 Listing Image for 145 N Kihei Rd 417 45 of 45

$829,000

↓ $69,000

Sugar Beach Resort 417

145 N Kihei Rd 417, Kihei

1 Bed 1 Bath 613 SqFt Residential MLS® # 409314 Date Sold: July 27, 2026
Sold
Closed: 07/13/2026
Listing Image for 87 Poniu Cir 1 of 50 Listing Image for 87 Poniu Cir 2 of 50 Listing Image for 87 Poniu Cir 3 of 50 Listing Image for 87 Poniu Cir 4 of 50 Listing Image for 87 Poniu Cir 5 of 50 Listing Image for 87 Poniu Cir 6 of 50 Listing Image for 87 Poniu Cir 7 of 50 Listing Image for 87 Poniu Cir 8 of 50 Listing Image for 87 Poniu Cir 9 of 50 Listing Image for 87 Poniu Cir 10 of 50 Listing Image for 87 Poniu Cir 11 of 50 Listing Image for 87 Poniu Cir 12 of 50 Listing Image for 87 Poniu Cir 13 of 50 Listing Image for 87 Poniu Cir 14 of 50 Listing Image for 87 Poniu Cir 15 of 50 Listing Image for 87 Poniu Cir 16 of 50 Listing Image for 87 Poniu Cir 17 of 50 Listing Image for 87 Poniu Cir 18 of 50 Listing Image for 87 Poniu Cir 19 of 50 Listing Image for 87 Poniu Cir 20 of 50 Listing Image for 87 Poniu Cir 21 of 50 Listing Image for 87 Poniu Cir 22 of 50 Listing Image for 87 Poniu Cir 23 of 50 Listing Image for 87 Poniu Cir 24 of 50 Listing Image for 87 Poniu Cir 25 of 50 Listing Image for 87 Poniu Cir 26 of 50 Listing Image for 87 Poniu Cir 27 of 50 Listing Image for 87 Poniu Cir 28 of 50 Listing Image for 87 Poniu Cir 29 of 50 Listing Image for 87 Poniu Cir 30 of 50 Listing Image for 87 Poniu Cir 31 of 50 Listing Image for 87 Poniu Cir 32 of 50 Listing Image for 87 Poniu Cir 33 of 50 Listing Image for 87 Poniu Cir 34 of 50 Listing Image for 87 Poniu Cir 35 of 50 Listing Image for 87 Poniu Cir 36 of 50 Listing Image for 87 Poniu Cir 37 of 50 Listing Image for 87 Poniu Cir 38 of 50 Listing Image for 87 Poniu Cir 39 of 50 Listing Image for 87 Poniu Cir 40 of 50 Listing Image for 87 Poniu Cir 41 of 50 Listing Image for 87 Poniu Cir 42 of 50 Listing Image for 87 Poniu Cir 43 of 50 Listing Image for 87 Poniu Cir 44 of 50 Listing Image for 87 Poniu Cir 45 of 50 Listing Image for 87 Poniu Cir 46 of 50 Listing Image for 87 Poniu Cir 47 of 50 Listing Image for 87 Poniu Cir 48 of 50 Listing Image for 87 Poniu Cir 49 of 50 Listing Image for 87 Poniu Cir 50 of 50

$900,000

Kaimana

87 Poniu Cir, Wailuku

3 Beds 2 Baths 1,185 SqFt Residential MLS® # 409313 Date Sold: July 13, 2026
Sold
Closed: 05/26/2026
Listing Image for 525 Kualau St 1 of 50 Listing Image for 525 Kualau St 2 of 50 Listing Image for 525 Kualau St 3 of 50 Listing Image for 525 Kualau St 4 of 50 Listing Image for 525 Kualau St 5 of 50 Listing Image for 525 Kualau St 6 of 50 Listing Image for 525 Kualau St 7 of 50 Listing Image for 525 Kualau St 8 of 50 Listing Image for 525 Kualau St 9 of 50 Listing Image for 525 Kualau St 10 of 50 Listing Image for 525 Kualau St 11 of 50 Listing Image for 525 Kualau St 12 of 50 Listing Image for 525 Kualau St 13 of 50 Listing Image for 525 Kualau St 14 of 50 Listing Image for 525 Kualau St 15 of 50 Listing Image for 525 Kualau St 16 of 50 Listing Image for 525 Kualau St 17 of 50 Listing Image for 525 Kualau St 18 of 50 Listing Image for 525 Kualau St 19 of 50 Listing Image for 525 Kualau St 20 of 50 Listing Image for 525 Kualau St 21 of 50 Listing Image for 525 Kualau St 22 of 50 Listing Image for 525 Kualau St 23 of 50 Listing Image for 525 Kualau St 24 of 50 Listing Image for 525 Kualau St 25 of 50 Listing Image for 525 Kualau St 26 of 50 Listing Image for 525 Kualau St 27 of 50 Listing Image for 525 Kualau St 28 of 50 Listing Image for 525 Kualau St 29 of 50 Listing Image for 525 Kualau St 30 of 50 Listing Image for 525 Kualau St 31 of 50 Listing Image for 525 Kualau St 32 of 50 Listing Image for 525 Kualau St 33 of 50 Listing Image for 525 Kualau St 34 of 50 Listing Image for 525 Kualau St 35 of 50 Listing Image for 525 Kualau St 36 of 50 Listing Image for 525 Kualau St 37 of 50 Listing Image for 525 Kualau St 38 of 50 Listing Image for 525 Kualau St 39 of 50 Listing Image for 525 Kualau St 40 of 50 Listing Image for 525 Kualau St 41 of 50 Listing Image for 525 Kualau St 42 of 50 Listing Image for 525 Kualau St 43 of 50 Listing Image for 525 Kualau St 44 of 50 Listing Image for 525 Kualau St 45 of 50 Listing Image for 525 Kualau St 46 of 50 Listing Image for 525 Kualau St 47 of 50 Listing Image for 525 Kualau St 48 of 50 Listing Image for 525 Kualau St 49 of 50 Listing Image for 525 Kualau St 50 of 50

$1,299,000

Wailuku Heights

525 Kualau St, Wailuku

3 Beds 2.5 Baths 1,627 SqFt Residential MLS® # 409308 Date Sold: May 26, 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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