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 1344 Hiahia St 1 of 48 Listing Image for 1344 Hiahia St 2 of 48 Listing Image for 1344 Hiahia St 3 of 48 Listing Image for 1344 Hiahia St 4 of 48 Listing Image for 1344 Hiahia St 5 of 48 Listing Image for 1344 Hiahia St 6 of 48 Listing Image for 1344 Hiahia St 7 of 48 Listing Image for 1344 Hiahia St 8 of 48 Listing Image for 1344 Hiahia St 9 of 48 Listing Image for 1344 Hiahia St 10 of 48 Listing Image for 1344 Hiahia St 11 of 48 Listing Image for 1344 Hiahia St 12 of 48 Listing Image for 1344 Hiahia St 13 of 48 Listing Image for 1344 Hiahia St 14 of 48 Listing Image for 1344 Hiahia St 15 of 48 Listing Image for 1344 Hiahia St 16 of 48 Listing Image for 1344 Hiahia St 17 of 48 Listing Image for 1344 Hiahia St 18 of 48 Listing Image for 1344 Hiahia St 19 of 48 Listing Image for 1344 Hiahia St 20 of 48 Listing Image for 1344 Hiahia St 21 of 48 Listing Image for 1344 Hiahia St 22 of 48 Listing Image for 1344 Hiahia St 23 of 48 Listing Image for 1344 Hiahia St 24 of 48 Listing Image for 1344 Hiahia St 25 of 48 Listing Image for 1344 Hiahia St 26 of 48 Listing Image for 1344 Hiahia St 27 of 48 Listing Image for 1344 Hiahia St 28 of 48 Listing Image for 1344 Hiahia St 29 of 48 Listing Image for 1344 Hiahia St 30 of 48 Listing Image for 1344 Hiahia St 31 of 48 Listing Image for 1344 Hiahia St 32 of 48 Listing Image for 1344 Hiahia St 33 of 48 Listing Image for 1344 Hiahia St 34 of 48 Listing Image for 1344 Hiahia St 35 of 48 Listing Image for 1344 Hiahia St 36 of 48 Listing Image for 1344 Hiahia St 37 of 48 Listing Image for 1344 Hiahia St 38 of 48 Listing Image for 1344 Hiahia St 39 of 48 Listing Image for 1344 Hiahia St 40 of 48 Listing Image for 1344 Hiahia St 41 of 48 Listing Image for 1344 Hiahia St 42 of 48 Listing Image for 1344 Hiahia St 43 of 48 Listing Image for 1344 Hiahia St 44 of 48 Listing Image for 1344 Hiahia St 45 of 48 Listing Image for 1344 Hiahia St 46 of 48 Listing Image for 1344 Hiahia St 47 of 48 Listing Image for 1344 Hiahia St 48 of 48

$1,529,000

↓ $70,000

Oceanview Estates

1344 Hiahia St, Wailuku

4 Beds 3 Baths 1,916 SqFt Residential MLS® # 409641

Days on Market: 120

Maui No Ka Oi Properties

Short Term Rental
Listing Image for 2481 Kaanapali Pkwy 418 1 of 3 Listing Image for 2481 Kaanapali Pkwy 418 2 of 3 Listing Image for 2481 Kaanapali Pkwy 418 3 of 3

$1,090,000

Whaler 418

2481 Kaanapali Pkwy 418, Kaanapali

0 Beds 1 Bath 542 SqFt Residential MLS® # 409639

Days on Market: 120

Berkshire Hathaway Maui Prop-L

Listing Image for 199 Puaehu St 1 of 50 Listing Image for 199 Puaehu St 2 of 50 Listing Image for 199 Puaehu St 3 of 50 Listing Image for 199 Puaehu St 4 of 50 Listing Image for 199 Puaehu St 5 of 50 Listing Image for 199 Puaehu St 6 of 50 Listing Image for 199 Puaehu St 7 of 50 Listing Image for 199 Puaehu St 8 of 50 Listing Image for 199 Puaehu St 9 of 50 Listing Image for 199 Puaehu St 10 of 50 Listing Image for 199 Puaehu St 11 of 50 Listing Image for 199 Puaehu St 12 of 50 Listing Image for 199 Puaehu St 13 of 50 Listing Image for 199 Puaehu St 14 of 50 Listing Image for 199 Puaehu St 15 of 50 Listing Image for 199 Puaehu St 16 of 50 Listing Image for 199 Puaehu St 17 of 50 Listing Image for 199 Puaehu St 18 of 50 Listing Image for 199 Puaehu St 19 of 50 Listing Image for 199 Puaehu St 20 of 50 Listing Image for 199 Puaehu St 21 of 50 Listing Image for 199 Puaehu St 22 of 50 Listing Image for 199 Puaehu St 23 of 50 Listing Image for 199 Puaehu St 24 of 50 Listing Image for 199 Puaehu St 25 of 50 Listing Image for 199 Puaehu St 26 of 50 Listing Image for 199 Puaehu St 27 of 50 Listing Image for 199 Puaehu St 28 of 50 Listing Image for 199 Puaehu St 29 of 50 Listing Image for 199 Puaehu St 30 of 50 Listing Image for 199 Puaehu St 31 of 50 Listing Image for 199 Puaehu St 32 of 50 Listing Image for 199 Puaehu St 33 of 50 Listing Image for 199 Puaehu St 34 of 50 Listing Image for 199 Puaehu St 35 of 50 Listing Image for 199 Puaehu St 36 of 50 Listing Image for 199 Puaehu St 37 of 50 Listing Image for 199 Puaehu St 38 of 50 Listing Image for 199 Puaehu St 39 of 50 Listing Image for 199 Puaehu St 40 of 50 Listing Image for 199 Puaehu St 41 of 50 Listing Image for 199 Puaehu St 42 of 50 Listing Image for 199 Puaehu St 43 of 50 Listing Image for 199 Puaehu St 44 of 50 Listing Image for 199 Puaehu St 45 of 50 Listing Image for 199 Puaehu St 46 of 50 Listing Image for 199 Puaehu St 47 of 50 Listing Image for 199 Puaehu St 48 of 50 Listing Image for 199 Puaehu St 49 of 50 Listing Image for 199 Puaehu St 50 of 50

$1,375,000

↓ $24,000

Ilima at Kehalani

199 Puaehu St, Wailuku

3 Beds 2 Baths 1,836 SqFt Residential MLS® # 409635

Days on Market: 120

Coldwell Banker Island Prop-Ku Cell: 808-757-6161

Short Term Rental
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$1,375,000

↓ $75,000

Hale Hui Kai 301

2994 S Kihei Rd 301, Kihei

2 Beds 2 Baths 898 SqFt Residential MLS® # 409623

Days on Market: 123

Island Sotheby's International Realty(W) Cell: 808-264-1695

Buying Real Estate on Maui

Buying Real Estate on Maui

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

Read the Guide
In Escrow
Listing Image for 1982 Kalawi Pl 1 of 29 Listing Image for 1982 Kalawi Pl 2 of 29 Listing Image for 1982 Kalawi Pl 3 of 29 Listing Image for 1982 Kalawi Pl 4 of 29 Listing Image for 1982 Kalawi Pl 5 of 29 Listing Image for 1982 Kalawi Pl 6 of 29 Listing Image for 1982 Kalawi Pl 7 of 29 Listing Image for 1982 Kalawi Pl 8 of 29 Listing Image for 1982 Kalawi Pl 9 of 29 Listing Image for 1982 Kalawi Pl 10 of 29 Listing Image for 1982 Kalawi Pl 11 of 29 Listing Image for 1982 Kalawi Pl 12 of 29 Listing Image for 1982 Kalawi Pl 13 of 29 Listing Image for 1982 Kalawi Pl 14 of 29 Listing Image for 1982 Kalawi Pl 15 of 29 Listing Image for 1982 Kalawi Pl 16 of 29 Listing Image for 1982 Kalawi Pl 17 of 29 Listing Image for 1982 Kalawi Pl 18 of 29 Listing Image for 1982 Kalawi Pl 19 of 29 Listing Image for 1982 Kalawi Pl 20 of 29 Listing Image for 1982 Kalawi Pl 21 of 29 Listing Image for 1982 Kalawi Pl 22 of 29 Listing Image for 1982 Kalawi Pl 23 of 29 Listing Image for 1982 Kalawi Pl 24 of 29 Listing Image for 1982 Kalawi Pl 25 of 29 Listing Image for 1982 Kalawi Pl 26 of 29 Listing Image for 1982 Kalawi Pl 27 of 29 Listing Image for 1982 Kalawi Pl 28 of 29 Listing Image for 1982 Kalawi Pl 29 of 29

$899,000

↓ $30,000

Wailuku

1982 Kalawi Pl, Wailuku

3 Beds 1 Bath 904 SqFt Residential MLS® # 409613

Days on Market: 123

Real Broker Cell: 808-214-8111

Listing Image for 965 Hog Back Rd 1 of 44 Listing Image for 965 Hog Back Rd 2 of 44 Listing Image for 965 Hog Back Rd 3 of 44 Listing Image for 965 Hog Back Rd 4 of 44 Listing Image for 965 Hog Back Rd 5 of 44 Listing Image for 965 Hog Back Rd 6 of 44 Listing Image for 965 Hog Back Rd 7 of 44 Listing Image for 965 Hog Back Rd 8 of 44 Listing Image for 965 Hog Back Rd 9 of 44 Listing Image for 965 Hog Back Rd 10 of 44 Listing Image for 965 Hog Back Rd 11 of 44 Listing Image for 965 Hog Back Rd 12 of 44 Listing Image for 965 Hog Back Rd 13 of 44 Listing Image for 965 Hog Back Rd 14 of 44 Listing Image for 965 Hog Back Rd 15 of 44 Listing Image for 965 Hog Back Rd 16 of 44 Listing Image for 965 Hog Back Rd 17 of 44 Listing Image for 965 Hog Back Rd 18 of 44 Listing Image for 965 Hog Back Rd 19 of 44 Listing Image for 965 Hog Back Rd 20 of 44 Listing Image for 965 Hog Back Rd 21 of 44 Listing Image for 965 Hog Back Rd 22 of 44 Listing Image for 965 Hog Back Rd 23 of 44 Listing Image for 965 Hog Back Rd 24 of 44 Listing Image for 965 Hog Back Rd 25 of 44 Listing Image for 965 Hog Back Rd 26 of 44 Listing Image for 965 Hog Back Rd 27 of 44 Listing Image for 965 Hog Back Rd 28 of 44 Listing Image for 965 Hog Back Rd 29 of 44 Listing Image for 965 Hog Back Rd 30 of 44 Listing Image for 965 Hog Back Rd 31 of 44 Listing Image for 965 Hog Back Rd 32 of 44 Listing Image for 965 Hog Back Rd 33 of 44 Listing Image for 965 Hog Back Rd 34 of 44 Listing Image for 965 Hog Back Rd 35 of 44 Listing Image for 965 Hog Back Rd 36 of 44 Listing Image for 965 Hog Back Rd 37 of 44 Listing Image for 965 Hog Back Rd 38 of 44 Listing Image for 965 Hog Back Rd 39 of 44 Listing Image for 965 Hog Back Rd 40 of 44 Listing Image for 965 Hog Back Rd 41 of 44 Listing Image for 965 Hog Back Rd 42 of 44 Listing Image for 965 Hog Back Rd 43 of 44 Listing Image for 965 Hog Back Rd 44 of 44

$3,250,000

Haiku

965 Hog Back Rd, Haiku

3 Beds 4 Baths 3,136 SqFt Residential MLS® # 408112

Days on Market: 275

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

Short Term Rental
Listing Image for 130 Kai Malina Pkwy Nr326 1 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 2 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 3 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 4 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 5 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 6 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 7 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 8 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 9 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 10 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 11 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 12 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 13 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 14 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 15 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 16 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 17 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 18 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 19 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 20 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 21 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 22 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 23 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 24 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 25 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 26 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 27 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 28 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 29 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 30 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 31 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 32 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 33 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 34 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 35 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 36 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 37 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 38 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 39 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 40 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 41 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 42 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 43 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 44 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 45 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 46 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 47 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 48 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 49 of 50 Listing Image for 130 Kai Malina Pkwy Nr326 50 of 50

$1,799,000

Honua Kai - Konea NR326

130 Kai Malina Pkwy Nr326, Kaanapali

2 Beds 2 Baths 1,285 SqFt Residential MLS® # 407720

Days on Market: 307

The Agency Maui Cell: 808-344-5575

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: 03/11/2026
Listing Image for 3133 Kikihi St Lot 414 1 of 49 Listing Image for 3133 Kikihi St Lot 414 2 of 49 Listing Image for 3133 Kikihi St Lot 414 3 of 49 Listing Image for 3133 Kikihi St Lot 414 4 of 49 Listing Image for 3133 Kikihi St Lot 414 5 of 49 Listing Image for 3133 Kikihi St Lot 414 6 of 49 Listing Image for 3133 Kikihi St Lot 414 7 of 49 Listing Image for 3133 Kikihi St Lot 414 8 of 49 Listing Image for 3133 Kikihi St Lot 414 9 of 49 Listing Image for 3133 Kikihi St Lot 414 10 of 49 Listing Image for 3133 Kikihi St Lot 414 11 of 49 Listing Image for 3133 Kikihi St Lot 414 12 of 49 Listing Image for 3133 Kikihi St Lot 414 13 of 49 Listing Image for 3133 Kikihi St Lot 414 14 of 49 Listing Image for 3133 Kikihi St Lot 414 15 of 49 Listing Image for 3133 Kikihi St Lot 414 16 of 49 Listing Image for 3133 Kikihi St Lot 414 17 of 49 Listing Image for 3133 Kikihi St Lot 414 18 of 49 Listing Image for 3133 Kikihi St Lot 414 19 of 49 Listing Image for 3133 Kikihi St Lot 414 20 of 49 Listing Image for 3133 Kikihi St Lot 414 21 of 49 Listing Image for 3133 Kikihi St Lot 414 22 of 49 Listing Image for 3133 Kikihi St Lot 414 23 of 49 Listing Image for 3133 Kikihi St Lot 414 24 of 49 Listing Image for 3133 Kikihi St Lot 414 25 of 49 Listing Image for 3133 Kikihi St Lot 414 26 of 49 Listing Image for 3133 Kikihi St Lot 414 27 of 49 Listing Image for 3133 Kikihi St Lot 414 28 of 49 Listing Image for 3133 Kikihi St Lot 414 29 of 49 Listing Image for 3133 Kikihi St Lot 414 30 of 49 Listing Image for 3133 Kikihi St Lot 414 31 of 49 Listing Image for 3133 Kikihi St Lot 414 32 of 49 Listing Image for 3133 Kikihi St Lot 414 33 of 49 Listing Image for 3133 Kikihi St Lot 414 34 of 49 Listing Image for 3133 Kikihi St Lot 414 35 of 49 Listing Image for 3133 Kikihi St Lot 414 36 of 49 Listing Image for 3133 Kikihi St Lot 414 37 of 49 Listing Image for 3133 Kikihi St Lot 414 38 of 49 Listing Image for 3133 Kikihi St Lot 414 39 of 49 Listing Image for 3133 Kikihi St Lot 414 40 of 49 Listing Image for 3133 Kikihi St Lot 414 41 of 49 Listing Image for 3133 Kikihi St Lot 414 42 of 49 Listing Image for 3133 Kikihi St Lot 414 43 of 49 Listing Image for 3133 Kikihi St Lot 414 44 of 49 Listing Image for 3133 Kikihi St Lot 414 45 of 49 Listing Image for 3133 Kikihi St Lot 414 46 of 49 Listing Image for 3133 Kikihi St Lot 414 47 of 49 Listing Image for 3133 Kikihi St Lot 414 48 of 49 Listing Image for 3133 Kikihi St Lot 414 49 of 49

$2,565,000

Wailea Kialoa

3133 Kikihi St Lot 414, Wailea/Makena

3 Beds 2 Baths 1,955 SqFt Residential MLS® # 408379 Date Sold: March 11, 2026
Sold
Closed: 05/12/2026
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$1,300,000

Kula/Ulupalakua/Kanaio

15980 Haleakala Hwy, Kula/Ulupalakua/Kanaio

3 Beds 2 Baths 1,350 SqFt Residential MLS® # 408371 Date Sold: May 12, 2026
Sold
Closed: 06/10/2026
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$1,999,000

↓ $296,000

Haiku

2600 Alohia Pl, Haiku

4 Beds 3 Baths 2,368 SqFt Residential MLS® # 408370 Date Sold: June 10, 2026
Sold
Closed: 01/09/2026
172 Oliona St 130, Makawao/Olinda/Haliimaile

$1,625,000

Hokuula

172 Oliona St 130, Makawao/Olinda/Haliimaile

4 Beds 3 Baths 1,960 SqFt Residential MLS® # 408366 Date Sold: January 9, 2026
Buying Real Estate on Maui

Buying Real Estate on Maui

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

Read the Guide
Sold
Closed: 08/07/2026
Listing Image for 27 Waihili Pl 1 of 44 Listing Image for 27 Waihili Pl 2 of 44 Listing Image for 27 Waihili Pl 3 of 44 Listing Image for 27 Waihili Pl 4 of 44 Listing Image for 27 Waihili Pl 5 of 44 Listing Image for 27 Waihili Pl 6 of 44 Listing Image for 27 Waihili Pl 7 of 44 Listing Image for 27 Waihili Pl 8 of 44 Listing Image for 27 Waihili Pl 9 of 44 Listing Image for 27 Waihili Pl 10 of 44 Listing Image for 27 Waihili Pl 11 of 44 Listing Image for 27 Waihili Pl 12 of 44 Listing Image for 27 Waihili Pl 13 of 44 Listing Image for 27 Waihili Pl 14 of 44 Listing Image for 27 Waihili Pl 15 of 44 Listing Image for 27 Waihili Pl 16 of 44 Listing Image for 27 Waihili Pl 17 of 44 Listing Image for 27 Waihili Pl 18 of 44 Listing Image for 27 Waihili Pl 19 of 44 Listing Image for 27 Waihili Pl 20 of 44 Listing Image for 27 Waihili Pl 21 of 44 Listing Image for 27 Waihili Pl 22 of 44 Listing Image for 27 Waihili Pl 23 of 44 Listing Image for 27 Waihili Pl 24 of 44 Listing Image for 27 Waihili Pl 25 of 44 Listing Image for 27 Waihili Pl 26 of 44 Listing Image for 27 Waihili Pl 27 of 44 Listing Image for 27 Waihili Pl 28 of 44 Listing Image for 27 Waihili Pl 29 of 44 Listing Image for 27 Waihili Pl 30 of 44 Listing Image for 27 Waihili Pl 31 of 44 Listing Image for 27 Waihili Pl 32 of 44 Listing Image for 27 Waihili Pl 33 of 44 Listing Image for 27 Waihili Pl 34 of 44 Listing Image for 27 Waihili Pl 35 of 44 Listing Image for 27 Waihili Pl 36 of 44 Listing Image for 27 Waihili Pl 37 of 44 Listing Image for 27 Waihili Pl 38 of 44 Listing Image for 27 Waihili Pl 39 of 44 Listing Image for 27 Waihili Pl 40 of 44 Listing Image for 27 Waihili Pl 41 of 44 Listing Image for 27 Waihili Pl 42 of 44 Listing Image for 27 Waihili Pl 43 of 44 Listing Image for 27 Waihili Pl 44 of 44

$860,000

↓ $89,900

Piilani Village III

27 Waihili Pl, Kihei

3 Beds 2.5 Baths 1,434 SqFt Residential MLS® # 408361 Date Sold: August 7, 2026
Sold
Closed: 03/17/2026
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$926,000

Kahului

94 S Lehua St, Kahului

3 Beds 1.5 Baths 1,361 SqFt Residential MLS® # 408347 Date Sold: March 17, 2026
View 6 More Listings

Consider a Bridge Loan

When looking at how to buy a house before selling yours, a bridge loan may be a great solution. A bridge loan, a short-term loan with a higher interest rate, can be used to refinance your current home mortgage or pull equity out as a second lien.

With interest-only payments, you can tap into your equity to use as a down payment to purchase a second home. You can also potentially decrease your first home’s mortgage payments, which will be beneficial if the closing dates do not align perfectly.

Choose a Low Down Payment Loan Program

While many mortgage lenders will require you to make a sizable down payment when you buy a house, there are lending solutions available that allow you to put down 5% or less. A Fannie Mae loan, for example, only requires 3% down. While the interest rates on these loans are competitive, you may be responsible for Mortgage Payment Insurance (MPI).

MPI could add hundreds of dollars to your monthly mortgage payment. With a low down payment loan, however, you may not need to access your current home’s equity to complete your purchase.

Borrow Against Your Retirement Account

Generally, your retirement account’s funds are inaccessible to you until you reach the age of 59.5 years old. Most withdrawals taken before you reach this age can trigger a penalty and will be taxable. However, the IRS allows you to withdraw funds without penalty to buy a house.

There are specific rules and requirements that you should research thoroughly before pursuing this option. Your retirement account funds can be used for a down payment as well as closing costs, and this could eliminate the need to sell your house before buying a new one.

Add a Contingency to the Sales Contract

If you have determined that the other options available are not suitable for your unique situation, another possibility is available. When considering how to buy a second home without selling the first, a sales contingency could be written into the new sales contract. A sales contingency can be worded so that your purchase is dependent on the sale of the current house. 

While this can seem like the perfect solution, be aware that many sellers may not accept this contingency. Like you, other sellers may be trying to sell their house to buy another property. If they delay their sale because of a sales contingency, they may not be able to structure their own timeline to suit their needs. Your real estate agent can work with you to structure a sales contingency with an agreeable seller.

Turn Your Home Into an Investment Property

If you are concerned about the possibility of having two mortgage payments at the same time, you could consider renting out your first home. The monthly rent from your rental property could cover its mortgage payment, property taxes, and other expenses. The remaining rental income is a profit that can be used as desired.

If you are unable to qualify for a new home loan for your purchase with the old mortgage in place, renting the property can help. Once you have a signed lease in place on your first home, your mortgage lender can apply that income to your debt-to-income ratio. 

Before turning your home into a rental, consult with your realtor. Your real estate agent can provide you with a fair market rental rate for the property. This information is required to determine if its monthly rent will cover its expenses. The IRS allows you to write off many property expenses, including upkeep costs, management fees, property taxes, etc. Depending on the situation, a property owner could possibly turn a profit on a rental house while enjoying a tax loss.

Consider Buying a Second Home

Buying a second home has advantages to consider as well. If you buy a second home, you can enjoy traveling back and forth between the locations as desired. When you are not using a home for personal use, you could rent it out as a rental property. A second home also has tax benefits

Even if you do not use the second home to produce rental income, you may qualify for the same homeowner tax deductions as you benefit from with your first home. Before buying a second home or turning your current home into a rental property, consider speaking to a tax advisor and a management company to explore all of the financial ramifications in detail.

Executing a 1031 Exchange

1031 Exchange Maui

When doing a 1031 exchange, you'll typically be selling the property you are going to exchange first and then immedietley seeking a replacement property. Read my full rundown on how to successfully navigate the process here

Explore Your Options Today

Keep in mind that you can combine multiple solutions presented here as you walk through the real estate process. For example, you could take out a home equity loan on your current home to access down payment funds to purchase your second home. At the same time, you could turn your first home into a rental property to generate monthly income.

This example is only one of many ways to combine these solutions and set up a scenario that suits your needs. Contact a local real estate agent to learn more about the housing and rental market.

Get In Touch With Evan!

Evan Harlow Maui

Evan Harlow ranks among the best real estate agents on Maui annually and is in the top 1% of Coldwell Banker agents worldwide in production. Evan has the expertise, experience, and work ethic to help you achieve your real estate buying and selling goals. We promise exceptional service and support from the beginning of the process through closing and beyond. See what Evan's clients are saying on Google.

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