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 5290 Lower Honoapiilani Rd A7 1 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 2 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 3 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 4 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 5 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 6 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 7 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 8 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 9 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 10 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 11 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 12 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 13 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 14 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 15 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 16 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 17 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 18 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 19 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 20 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 21 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 22 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 23 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 24 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 25 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 26 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 27 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 28 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 29 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 30 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 31 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 32 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 33 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 34 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 35 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 36 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 37 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 38 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 39 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 40 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 41 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 42 of 43 Listing Image for 5290 Lower Honoapiilani Rd A7 43 of 43

$1,245,000

↓ $50,000

Napili Point A7

5290 Lower Honoapiilani Rd A7, Napili/Kahana/Honokowai

1 Bed 1 Bath 602 SqFt Residential MLS® # 410420

Days on Market: 41

Berkshire Hathaway Maui Prop-L Cell: 808-205-3997

Short Term Rental
Listing Image for 500 Kapalua Dr 22p3-4 1 of 37 Listing Image for 500 Kapalua Dr 22p3-4 2 of 37 Listing Image for 500 Kapalua Dr 22p3-4 3 of 37 Listing Image for 500 Kapalua Dr 22p3-4 4 of 37 Listing Image for 500 Kapalua Dr 22p3-4 5 of 37 Listing Image for 500 Kapalua Dr 22p3-4 6 of 37 Listing Image for 500 Kapalua Dr 22p3-4 7 of 37 Listing Image for 500 Kapalua Dr 22p3-4 8 of 37 Listing Image for 500 Kapalua Dr 22p3-4 9 of 37 Listing Image for 500 Kapalua Dr 22p3-4 10 of 37 Listing Image for 500 Kapalua Dr 22p3-4 11 of 37 Listing Image for 500 Kapalua Dr 22p3-4 12 of 37 Listing Image for 500 Kapalua Dr 22p3-4 13 of 37 Listing Image for 500 Kapalua Dr 22p3-4 14 of 37 Listing Image for 500 Kapalua Dr 22p3-4 15 of 37 Listing Image for 500 Kapalua Dr 22p3-4 16 of 37 Listing Image for 500 Kapalua Dr 22p3-4 17 of 37 Listing Image for 500 Kapalua Dr 22p3-4 18 of 37 Listing Image for 500 Kapalua Dr 22p3-4 19 of 37 Listing Image for 500 Kapalua Dr 22p3-4 20 of 37 Listing Image for 500 Kapalua Dr 22p3-4 21 of 37 Listing Image for 500 Kapalua Dr 22p3-4 22 of 37 Listing Image for 500 Kapalua Dr 22p3-4 23 of 37 Listing Image for 500 Kapalua Dr 22p3-4 24 of 37 Listing Image for 500 Kapalua Dr 22p3-4 25 of 37 Listing Image for 500 Kapalua Dr 22p3-4 26 of 37 Listing Image for 500 Kapalua Dr 22p3-4 27 of 37 Listing Image for 500 Kapalua Dr 22p3-4 28 of 37 Listing Image for 500 Kapalua Dr 22p3-4 29 of 37 Listing Image for 500 Kapalua Dr 22p3-4 30 of 37 Listing Image for 500 Kapalua Dr 22p3-4 31 of 37 Listing Image for 500 Kapalua Dr 22p3-4 32 of 37 Listing Image for 500 Kapalua Dr 22p3-4 33 of 37 Listing Image for 500 Kapalua Dr 22p3-4 34 of 37 Listing Image for 500 Kapalua Dr 22p3-4 35 of 37 Listing Image for 500 Kapalua Dr 22p3-4 36 of 37 Listing Image for 500 Kapalua Dr 22p3-4 37 of 37

$1,390,000

Kapalua Golf Villas 22P3-4

500 Kapalua Dr 22p3-4, Kapalua

2 Beds 2 Baths 1,344 SqFt Residential MLS® # 410419

Days on Market: 41

Lowson & Associates laurie@lowson.com

Short Term Rental
Listing Image for 1032 S Kihei Rd B420 1 of 49 Listing Image for 1032 S Kihei Rd B420 2 of 49 Listing Image for 1032 S Kihei Rd B420 3 of 49 Listing Image for 1032 S Kihei Rd B420 4 of 49 Listing Image for 1032 S Kihei Rd B420 5 of 49 Listing Image for 1032 S Kihei Rd B420 6 of 49 Listing Image for 1032 S Kihei Rd B420 7 of 49 Listing Image for 1032 S Kihei Rd B420 8 of 49 Listing Image for 1032 S Kihei Rd B420 9 of 49 Listing Image for 1032 S Kihei Rd B420 10 of 49 Listing Image for 1032 S Kihei Rd B420 11 of 49 Listing Image for 1032 S Kihei Rd B420 12 of 49 Listing Image for 1032 S Kihei Rd B420 13 of 49 Listing Image for 1032 S Kihei Rd B420 14 of 49 Listing Image for 1032 S Kihei Rd B420 15 of 49 Listing Image for 1032 S Kihei Rd B420 16 of 49 Listing Image for 1032 S Kihei Rd B420 17 of 49 Listing Image for 1032 S Kihei Rd B420 18 of 49 Listing Image for 1032 S Kihei Rd B420 19 of 49 Listing Image for 1032 S Kihei Rd B420 20 of 49 Listing Image for 1032 S Kihei Rd B420 21 of 49 Listing Image for 1032 S Kihei Rd B420 22 of 49 Listing Image for 1032 S Kihei Rd B420 23 of 49 Listing Image for 1032 S Kihei Rd B420 24 of 49 Listing Image for 1032 S Kihei Rd B420 25 of 49 Listing Image for 1032 S Kihei Rd B420 26 of 49 Listing Image for 1032 S Kihei Rd B420 27 of 49 Listing Image for 1032 S Kihei Rd B420 28 of 49 Listing Image for 1032 S Kihei Rd B420 29 of 49 Listing Image for 1032 S Kihei Rd B420 30 of 49 Listing Image for 1032 S Kihei Rd B420 31 of 49 Listing Image for 1032 S Kihei Rd B420 32 of 49 Listing Image for 1032 S Kihei Rd B420 33 of 49 Listing Image for 1032 S Kihei Rd B420 34 of 49 Listing Image for 1032 S Kihei Rd B420 35 of 49 Listing Image for 1032 S Kihei Rd B420 36 of 49 Listing Image for 1032 S Kihei Rd B420 37 of 49 Listing Image for 1032 S Kihei Rd B420 38 of 49 Listing Image for 1032 S Kihei Rd B420 39 of 49 Listing Image for 1032 S Kihei Rd B420 40 of 49 Listing Image for 1032 S Kihei Rd B420 41 of 49 Listing Image for 1032 S Kihei Rd B420 42 of 49 Listing Image for 1032 S Kihei Rd B420 43 of 49 Listing Image for 1032 S Kihei Rd B420 44 of 49 Listing Image for 1032 S Kihei Rd B420 45 of 49 Listing Image for 1032 S Kihei Rd B420 46 of 49 Listing Image for 1032 S Kihei Rd B420 47 of 49 Listing Image for 1032 S Kihei Rd B420 48 of 49 Listing Image for 1032 S Kihei Rd B420 49 of 49

$1,395,000

Maui Sunset B420

1032 S Kihei Rd B420, Kihei

2 Beds 2 Baths 951 SqFt Residential MLS® # 405471

Days on Market: 531

Kumulani Vacations&Realty

In Escrow
Listing Image for 115 Alaluana Rd 1 of 49 Listing Image for 115 Alaluana Rd 2 of 49 Listing Image for 115 Alaluana Rd 3 of 49 Listing Image for 115 Alaluana Rd 4 of 49 Listing Image for 115 Alaluana Rd 5 of 49 Listing Image for 115 Alaluana Rd 6 of 49 Listing Image for 115 Alaluana Rd 7 of 49 Listing Image for 115 Alaluana Rd 8 of 49 Listing Image for 115 Alaluana Rd 9 of 49 Listing Image for 115 Alaluana Rd 10 of 49 Listing Image for 115 Alaluana Rd 11 of 49 Listing Image for 115 Alaluana Rd 12 of 49 Listing Image for 115 Alaluana Rd 13 of 49 Listing Image for 115 Alaluana Rd 14 of 49 Listing Image for 115 Alaluana Rd 15 of 49 Listing Image for 115 Alaluana Rd 16 of 49 Listing Image for 115 Alaluana Rd 17 of 49 Listing Image for 115 Alaluana Rd 18 of 49 Listing Image for 115 Alaluana Rd 19 of 49 Listing Image for 115 Alaluana Rd 20 of 49 Listing Image for 115 Alaluana Rd 21 of 49 Listing Image for 115 Alaluana Rd 22 of 49 Listing Image for 115 Alaluana Rd 23 of 49 Listing Image for 115 Alaluana Rd 24 of 49 Listing Image for 115 Alaluana Rd 25 of 49 Listing Image for 115 Alaluana Rd 26 of 49 Listing Image for 115 Alaluana Rd 27 of 49 Listing Image for 115 Alaluana Rd 28 of 49 Listing Image for 115 Alaluana Rd 29 of 49 Listing Image for 115 Alaluana Rd 30 of 49 Listing Image for 115 Alaluana Rd 31 of 49 Listing Image for 115 Alaluana Rd 32 of 49 Listing Image for 115 Alaluana Rd 33 of 49 Listing Image for 115 Alaluana Rd 34 of 49 Listing Image for 115 Alaluana Rd 35 of 49 Listing Image for 115 Alaluana Rd 36 of 49 Listing Image for 115 Alaluana Rd 37 of 49 Listing Image for 115 Alaluana Rd 38 of 49 Listing Image for 115 Alaluana Rd 39 of 49 Listing Image for 115 Alaluana Rd 40 of 49 Listing Image for 115 Alaluana Rd 41 of 49 Listing Image for 115 Alaluana Rd 42 of 49 Listing Image for 115 Alaluana Rd 43 of 49 Listing Image for 115 Alaluana Rd 44 of 49 Listing Image for 115 Alaluana Rd 45 of 49 Listing Image for 115 Alaluana Rd 46 of 49 Listing Image for 115 Alaluana Rd 47 of 49 Listing Image for 115 Alaluana Rd 48 of 49 Listing Image for 115 Alaluana Rd 49 of 49

$1,500,000

Makawao/Olinda/Haliimaile

115 Alaluana Rd, Makawao/Olinda/Haliimaile

2 Beds 2 Baths 2,113 SqFt Residential MLS® # 410416

Days on Market: 42

Compass-W

Listing Image for 10 Kamaiki Cir 1 of 20 Listing Image for 10 Kamaiki Cir 2 of 20 Listing Image for 10 Kamaiki Cir 3 of 20 Listing Image for 10 Kamaiki Cir 4 of 20 Listing Image for 10 Kamaiki Cir 5 of 20 Listing Image for 10 Kamaiki Cir 6 of 20 Listing Image for 10 Kamaiki Cir 7 of 20 Listing Image for 10 Kamaiki Cir 8 of 20 Listing Image for 10 Kamaiki Cir 9 of 20 Listing Image for 10 Kamaiki Cir 10 of 20 Listing Image for 10 Kamaiki Cir 11 of 20 Listing Image for 10 Kamaiki Cir 12 of 20 Listing Image for 10 Kamaiki Cir 13 of 20 Listing Image for 10 Kamaiki Cir 14 of 20 Listing Image for 10 Kamaiki Cir 15 of 20 Listing Image for 10 Kamaiki Cir 16 of 20 Listing Image for 10 Kamaiki Cir 17 of 20 Listing Image for 10 Kamaiki Cir 18 of 20 Listing Image for 10 Kamaiki Cir 19 of 20 Listing Image for 10 Kamaiki Cir 20 of 20

$1,650,000

Maui Lani Island & Bluff

10 Kamaiki Cir, Kahului

6 Beds 2.2 Baths 3,699 SqFt Residential MLS® # 410415

Days on Market: 42

Coldwell Banker Island Prop(S) Cell: 808-344-0180

Listing Image for 212 Crestview Rd 1 of 50 Listing Image for 212 Crestview Rd 2 of 50 Listing Image for 212 Crestview Rd 3 of 50 Listing Image for 212 Crestview Rd 4 of 50 Listing Image for 212 Crestview Rd 5 of 50 Listing Image for 212 Crestview Rd 6 of 50 Listing Image for 212 Crestview Rd 7 of 50 Listing Image for 212 Crestview Rd 8 of 50 Listing Image for 212 Crestview Rd 9 of 50 Listing Image for 212 Crestview Rd 10 of 50 Listing Image for 212 Crestview Rd 11 of 50 Listing Image for 212 Crestview Rd 12 of 50 Listing Image for 212 Crestview Rd 13 of 50 Listing Image for 212 Crestview Rd 14 of 50 Listing Image for 212 Crestview Rd 15 of 50 Listing Image for 212 Crestview Rd 16 of 50 Listing Image for 212 Crestview Rd 17 of 50 Listing Image for 212 Crestview Rd 18 of 50 Listing Image for 212 Crestview Rd 19 of 50 Listing Image for 212 Crestview Rd 20 of 50 Listing Image for 212 Crestview Rd 21 of 50 Listing Image for 212 Crestview Rd 22 of 50 Listing Image for 212 Crestview Rd 23 of 50 Listing Image for 212 Crestview Rd 24 of 50 Listing Image for 212 Crestview Rd 25 of 50 Listing Image for 212 Crestview Rd 26 of 50 Listing Image for 212 Crestview Rd 27 of 50 Listing Image for 212 Crestview Rd 28 of 50 Listing Image for 212 Crestview Rd 29 of 50 Listing Image for 212 Crestview Rd 30 of 50 Listing Image for 212 Crestview Rd 31 of 50 Listing Image for 212 Crestview Rd 32 of 50 Listing Image for 212 Crestview Rd 33 of 50 Listing Image for 212 Crestview Rd 34 of 50 Listing Image for 212 Crestview Rd 35 of 50 Listing Image for 212 Crestview Rd 36 of 50 Listing Image for 212 Crestview Rd 37 of 50 Listing Image for 212 Crestview Rd 38 of 50 Listing Image for 212 Crestview Rd 39 of 50 Listing Image for 212 Crestview Rd 40 of 50 Listing Image for 212 Crestview Rd 41 of 50 Listing Image for 212 Crestview Rd 42 of 50 Listing Image for 212 Crestview Rd 43 of 50 Listing Image for 212 Crestview Rd 44 of 50 Listing Image for 212 Crestview Rd 45 of 50 Listing Image for 212 Crestview Rd 46 of 50 Listing Image for 212 Crestview Rd 47 of 50 Listing Image for 212 Crestview Rd 48 of 50 Listing Image for 212 Crestview Rd 49 of 50 Listing Image for 212 Crestview Rd 50 of 50

$3,495,000

Pineapple Hill

212 Crestview Rd, Kapalua

3 Beds 3.5 Baths 3,674 SqFt Residential MLS® # 410414

Days on Market: 42

Island Sotheby's International Realty(L) Cell: 808-298-3498

View 6 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: 06/01/2026
Listing Image for 265 Ohaoha Pl 1 of 29 Listing Image for 265 Ohaoha Pl 2 of 29 Listing Image for 265 Ohaoha Pl 3 of 29 Listing Image for 265 Ohaoha Pl 4 of 29 Listing Image for 265 Ohaoha Pl 5 of 29 Listing Image for 265 Ohaoha Pl 6 of 29 Listing Image for 265 Ohaoha Pl 7 of 29 Listing Image for 265 Ohaoha Pl 8 of 29 Listing Image for 265 Ohaoha Pl 9 of 29 Listing Image for 265 Ohaoha Pl 10 of 29 Listing Image for 265 Ohaoha Pl 11 of 29 Listing Image for 265 Ohaoha Pl 12 of 29 Listing Image for 265 Ohaoha Pl 13 of 29 Listing Image for 265 Ohaoha Pl 14 of 29 Listing Image for 265 Ohaoha Pl 15 of 29 Listing Image for 265 Ohaoha Pl 16 of 29 Listing Image for 265 Ohaoha Pl 17 of 29 Listing Image for 265 Ohaoha Pl 18 of 29 Listing Image for 265 Ohaoha Pl 19 of 29 Listing Image for 265 Ohaoha Pl 20 of 29 Listing Image for 265 Ohaoha Pl 21 of 29 Listing Image for 265 Ohaoha Pl 22 of 29 Listing Image for 265 Ohaoha Pl 23 of 29 Listing Image for 265 Ohaoha Pl 24 of 29 Listing Image for 265 Ohaoha Pl 25 of 29 Listing Image for 265 Ohaoha Pl 26 of 29 Listing Image for 265 Ohaoha Pl 27 of 29 Listing Image for 265 Ohaoha Pl 28 of 29 Listing Image for 265 Ohaoha Pl 29 of 29

$2,800,000

Makawao/Olinda/Haliimaile

265 Ohaoha Pl, Makawao/Olinda/Haliimaile

4 Beds 2.5 Baths 2,456 SqFt Residential MLS® # 409299 Date Sold: June 1, 2026
Sold
Closed: 06/25/2026
Listing Image for 96 Kinohi Loa St Lot 62 1 of 25 Listing Image for 96 Kinohi Loa St Lot 62 2 of 25 Listing Image for 96 Kinohi Loa St Lot 62 3 of 25 Listing Image for 96 Kinohi Loa St Lot 62 4 of 25 Listing Image for 96 Kinohi Loa St Lot 62 5 of 25 Listing Image for 96 Kinohi Loa St Lot 62 6 of 25 Listing Image for 96 Kinohi Loa St Lot 62 7 of 25 Listing Image for 96 Kinohi Loa St Lot 62 8 of 25 Listing Image for 96 Kinohi Loa St Lot 62 9 of 25 Listing Image for 96 Kinohi Loa St Lot 62 10 of 25 Listing Image for 96 Kinohi Loa St Lot 62 11 of 25 Listing Image for 96 Kinohi Loa St Lot 62 12 of 25 Listing Image for 96 Kinohi Loa St Lot 62 13 of 25 Listing Image for 96 Kinohi Loa St Lot 62 14 of 25 Listing Image for 96 Kinohi Loa St Lot 62 15 of 25 Listing Image for 96 Kinohi Loa St Lot 62 16 of 25 Listing Image for 96 Kinohi Loa St Lot 62 17 of 25 Listing Image for 96 Kinohi Loa St Lot 62 18 of 25 Listing Image for 96 Kinohi Loa St Lot 62 19 of 25 Listing Image for 96 Kinohi Loa St Lot 62 20 of 25 Listing Image for 96 Kinohi Loa St Lot 62 21 of 25 Listing Image for 96 Kinohi Loa St Lot 62 22 of 25 Listing Image for 96 Kinohi Loa St Lot 62 23 of 25 Listing Image for 96 Kinohi Loa St Lot 62 24 of 25 Listing Image for 96 Kinohi Loa St Lot 62 25 of 25

$975,000

↓ $75,000

Kehalani

96 Kinohi Loa St Lot 62, Wailuku

3 Beds 2.5 Baths 1,403 SqFt Residential MLS® # 409297 Date Sold: June 25, 2026
Sold
Closed: 09/01/2026
Listing Image for 16 Kai Makani Loop D201 1 of 50 Listing Image for 16 Kai Makani Loop D201 2 of 50 Listing Image for 16 Kai Makani Loop D201 3 of 50 Listing Image for 16 Kai Makani Loop D201 4 of 50 Listing Image for 16 Kai Makani Loop D201 5 of 50 Listing Image for 16 Kai Makani Loop D201 6 of 50 Listing Image for 16 Kai Makani Loop D201 7 of 50 Listing Image for 16 Kai Makani Loop D201 8 of 50 Listing Image for 16 Kai Makani Loop D201 9 of 50 Listing Image for 16 Kai Makani Loop D201 10 of 50 Listing Image for 16 Kai Makani Loop D201 11 of 50 Listing Image for 16 Kai Makani Loop D201 12 of 50 Listing Image for 16 Kai Makani Loop D201 13 of 50 Listing Image for 16 Kai Makani Loop D201 14 of 50 Listing Image for 16 Kai Makani Loop D201 15 of 50 Listing Image for 16 Kai Makani Loop D201 16 of 50 Listing Image for 16 Kai Makani Loop D201 17 of 50 Listing Image for 16 Kai Makani Loop D201 18 of 50 Listing Image for 16 Kai Makani Loop D201 19 of 50 Listing Image for 16 Kai Makani Loop D201 20 of 50 Listing Image for 16 Kai Makani Loop D201 21 of 50 Listing Image for 16 Kai Makani Loop D201 22 of 50 Listing Image for 16 Kai Makani Loop D201 23 of 50 Listing Image for 16 Kai Makani Loop D201 24 of 50 Listing Image for 16 Kai Makani Loop D201 25 of 50 Listing Image for 16 Kai Makani Loop D201 26 of 50 Listing Image for 16 Kai Makani Loop D201 27 of 50 Listing Image for 16 Kai Makani Loop D201 28 of 50 Listing Image for 16 Kai Makani Loop D201 29 of 50 Listing Image for 16 Kai Makani Loop D201 30 of 50 Listing Image for 16 Kai Makani Loop D201 31 of 50 Listing Image for 16 Kai Makani Loop D201 32 of 50 Listing Image for 16 Kai Makani Loop D201 33 of 50 Listing Image for 16 Kai Makani Loop D201 34 of 50 Listing Image for 16 Kai Makani Loop D201 35 of 50 Listing Image for 16 Kai Makani Loop D201 36 of 50 Listing Image for 16 Kai Makani Loop D201 37 of 50 Listing Image for 16 Kai Makani Loop D201 38 of 50 Listing Image for 16 Kai Makani Loop D201 39 of 50 Listing Image for 16 Kai Makani Loop D201 40 of 50 Listing Image for 16 Kai Makani Loop D201 41 of 50 Listing Image for 16 Kai Makani Loop D201 42 of 50 Listing Image for 16 Kai Makani Loop D201 43 of 50 Listing Image for 16 Kai Makani Loop D201 44 of 50 Listing Image for 16 Kai Makani Loop D201 45 of 50 Listing Image for 16 Kai Makani Loop D201 46 of 50 Listing Image for 16 Kai Makani Loop D201 47 of 50 Listing Image for 16 Kai Makani Loop D201 48 of 50 Listing Image for 16 Kai Makani Loop D201 49 of 50 Listing Image for 16 Kai Makani Loop D201 50 of 50

$995,000

↓ $105,000

Kai Makani D201

16 Kai Makani Loop D201, Kihei

3 Beds 2 Baths 1,238 SqFt Residential MLS® # 409284 Date Sold: September 1, 2026
Sold
Closed: 06/10/2026
Listing Image for 2777 S Kihei Rd J214 1 of 46 Listing Image for 2777 S Kihei Rd J214 2 of 46 Listing Image for 2777 S Kihei Rd J214 3 of 46 Listing Image for 2777 S Kihei Rd J214 4 of 46 Listing Image for 2777 S Kihei Rd J214 5 of 46 Listing Image for 2777 S Kihei Rd J214 6 of 46 Listing Image for 2777 S Kihei Rd J214 7 of 46 Listing Image for 2777 S Kihei Rd J214 8 of 46 Listing Image for 2777 S Kihei Rd J214 9 of 46 Listing Image for 2777 S Kihei Rd J214 10 of 46 Listing Image for 2777 S Kihei Rd J214 11 of 46 Listing Image for 2777 S Kihei Rd J214 12 of 46 Listing Image for 2777 S Kihei Rd J214 13 of 46 Listing Image for 2777 S Kihei Rd J214 14 of 46 Listing Image for 2777 S Kihei Rd J214 15 of 46 Listing Image for 2777 S Kihei Rd J214 16 of 46 Listing Image for 2777 S Kihei Rd J214 17 of 46 Listing Image for 2777 S Kihei Rd J214 18 of 46 Listing Image for 2777 S Kihei Rd J214 19 of 46 Listing Image for 2777 S Kihei Rd J214 20 of 46 Listing Image for 2777 S Kihei Rd J214 21 of 46 Listing Image for 2777 S Kihei Rd J214 22 of 46 Listing Image for 2777 S Kihei Rd J214 23 of 46 Listing Image for 2777 S Kihei Rd J214 24 of 46 Listing Image for 2777 S Kihei Rd J214 25 of 46 Listing Image for 2777 S Kihei Rd J214 26 of 46 Listing Image for 2777 S Kihei Rd J214 27 of 46 Listing Image for 2777 S Kihei Rd J214 28 of 46 Listing Image for 2777 S Kihei Rd J214 29 of 46 Listing Image for 2777 S Kihei Rd J214 30 of 46 Listing Image for 2777 S Kihei Rd J214 31 of 46 Listing Image for 2777 S Kihei Rd J214 32 of 46 Listing Image for 2777 S Kihei Rd J214 33 of 46 Listing Image for 2777 S Kihei Rd J214 34 of 46 Listing Image for 2777 S Kihei Rd J214 35 of 46 Listing Image for 2777 S Kihei Rd J214 36 of 46 Listing Image for 2777 S Kihei Rd J214 37 of 46 Listing Image for 2777 S Kihei Rd J214 38 of 46 Listing Image for 2777 S Kihei Rd J214 39 of 46 Listing Image for 2777 S Kihei Rd J214 40 of 46 Listing Image for 2777 S Kihei Rd J214 41 of 46 Listing Image for 2777 S Kihei Rd J214 42 of 46 Listing Image for 2777 S Kihei Rd J214 43 of 46 Listing Image for 2777 S Kihei Rd J214 44 of 46 Listing Image for 2777 S Kihei Rd J214 45 of 46 Listing Image for 2777 S Kihei Rd J214 46 of 46

$930,000

Maui Kamaole J214

2777 S Kihei Rd J214, Kihei

2 Beds 2 Baths 1,052 SqFt Residential MLS® # 409274 Date Sold: June 10, 2026
Sold
Closed: 07/29/2026
Listing Image for 2695 S Kihei Rd 6-402 1 of 47 Listing Image for 2695 S Kihei Rd 6-402 2 of 47 Listing Image for 2695 S Kihei Rd 6-402 3 of 47 Listing Image for 2695 S Kihei Rd 6-402 4 of 47 Listing Image for 2695 S Kihei Rd 6-402 5 of 47 Listing Image for 2695 S Kihei Rd 6-402 6 of 47 Listing Image for 2695 S Kihei Rd 6-402 7 of 47 Listing Image for 2695 S Kihei Rd 6-402 8 of 47 Listing Image for 2695 S Kihei Rd 6-402 9 of 47 Listing Image for 2695 S Kihei Rd 6-402 10 of 47 Listing Image for 2695 S Kihei Rd 6-402 11 of 47 Listing Image for 2695 S Kihei Rd 6-402 12 of 47 Listing Image for 2695 S Kihei Rd 6-402 13 of 47 Listing Image for 2695 S Kihei Rd 6-402 14 of 47 Listing Image for 2695 S Kihei Rd 6-402 15 of 47 Listing Image for 2695 S Kihei Rd 6-402 16 of 47 Listing Image for 2695 S Kihei Rd 6-402 17 of 47 Listing Image for 2695 S Kihei Rd 6-402 18 of 47 Listing Image for 2695 S Kihei Rd 6-402 19 of 47 Listing Image for 2695 S Kihei Rd 6-402 20 of 47 Listing Image for 2695 S Kihei Rd 6-402 21 of 47 Listing Image for 2695 S Kihei Rd 6-402 22 of 47 Listing Image for 2695 S Kihei Rd 6-402 23 of 47 Listing Image for 2695 S Kihei Rd 6-402 24 of 47 Listing Image for 2695 S Kihei Rd 6-402 25 of 47 Listing Image for 2695 S Kihei Rd 6-402 26 of 47 Listing Image for 2695 S Kihei Rd 6-402 27 of 47 Listing Image for 2695 S Kihei Rd 6-402 28 of 47 Listing Image for 2695 S Kihei Rd 6-402 29 of 47 Listing Image for 2695 S Kihei Rd 6-402 30 of 47 Listing Image for 2695 S Kihei Rd 6-402 31 of 47 Listing Image for 2695 S Kihei Rd 6-402 32 of 47 Listing Image for 2695 S Kihei Rd 6-402 33 of 47 Listing Image for 2695 S Kihei Rd 6-402 34 of 47 Listing Image for 2695 S Kihei Rd 6-402 35 of 47 Listing Image for 2695 S Kihei Rd 6-402 36 of 47 Listing Image for 2695 S Kihei Rd 6-402 37 of 47 Listing Image for 2695 S Kihei Rd 6-402 38 of 47 Listing Image for 2695 S Kihei Rd 6-402 39 of 47 Listing Image for 2695 S Kihei Rd 6-402 40 of 47 Listing Image for 2695 S Kihei Rd 6-402 41 of 47 Listing Image for 2695 S Kihei Rd 6-402 42 of 47 Listing Image for 2695 S Kihei Rd 6-402 43 of 47 Listing Image for 2695 S Kihei Rd 6-402 44 of 47 Listing Image for 2695 S Kihei Rd 6-402 45 of 47 Listing Image for 2695 S Kihei Rd 6-402 46 of 47 Listing Image for 2695 S Kihei Rd 6-402 47 of 47

$782,000

↓ $97,000

Kamaole Sands 6-402

2695 S Kihei Rd 6-402, Kihei

2 Beds 2 Baths 1,188 SqFt Residential MLS® # 409267 Date Sold: July 29, 2026
Sold
Closed: 08/03/2026
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$1,300,000

Kahului

665 Pio Dr, Kahului

5 Beds 3 Baths 1,534 SqFt Residential MLS® # 409266 Date Sold: August 3, 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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