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 115 Unahe Pl Lot 133-a 1 of 12 Listing Image for 115 Unahe Pl Lot 133-a 2 of 12 Listing Image for 115 Unahe Pl Lot 133-a 3 of 12 Listing Image for 115 Unahe Pl Lot 133-a 4 of 12 Listing Image for 115 Unahe Pl Lot 133-a 5 of 12 Listing Image for 115 Unahe Pl Lot 133-a 6 of 12 Listing Image for 115 Unahe Pl Lot 133-a 7 of 12 Listing Image for 115 Unahe Pl Lot 133-a 8 of 12 Listing Image for 115 Unahe Pl Lot 133-a 9 of 12 Listing Image for 115 Unahe Pl Lot 133-a 10 of 12 Listing Image for 115 Unahe Pl Lot 133-a 11 of 12 Listing Image for 115 Unahe Pl Lot 133-a 12 of 12

$1,499,999

↓ $50,946

The Parkways at Maui Lani

115 Unahe Pl Lot 133-a, Kahului

4 Beds 2.5 Baths 2,230 SqFt Residential MLS® # 408592

Days on Market: 230

Towne Island Homes, Ltd

Short Term Rental
Listing Image for 4000 Wailea Alanui Dr 3404 1 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 2 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 3 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 4 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 5 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 6 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 7 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 8 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 9 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 10 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 11 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 12 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 13 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 14 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 15 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 16 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 17 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 18 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 19 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 20 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 21 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 22 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 23 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 24 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 25 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 26 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 27 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 28 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 29 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 30 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 31 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 32 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 33 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 34 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 35 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 36 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 37 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 38 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 39 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 40 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 41 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 42 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 43 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 44 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 45 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 46 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 47 of 48 Listing Image for 4000 Wailea Alanui Dr 3404 48 of 48

$2,795,000

↓ $190,000

Wailea Point 3404

4000 Wailea Alanui Dr 3404, Wailea/Makena

2 Beds 2 Baths 1,359 SqFt Residential MLS® # 408567

Days on Market: 231

Maui Real Estate Advisors LLC 808-875-4444

Listing Image for 81 Maika St 1 of 50 Listing Image for 81 Maika St 2 of 50 Listing Image for 81 Maika St 3 of 50 Listing Image for 81 Maika St 4 of 50 Listing Image for 81 Maika St 5 of 50 Listing Image for 81 Maika St 6 of 50 Listing Image for 81 Maika St 7 of 50 Listing Image for 81 Maika St 8 of 50 Listing Image for 81 Maika St 9 of 50 Listing Image for 81 Maika St 10 of 50 Listing Image for 81 Maika St 11 of 50 Listing Image for 81 Maika St 12 of 50 Listing Image for 81 Maika St 13 of 50 Listing Image for 81 Maika St 14 of 50 Listing Image for 81 Maika St 15 of 50 Listing Image for 81 Maika St 16 of 50 Listing Image for 81 Maika St 17 of 50 Listing Image for 81 Maika St 18 of 50 Listing Image for 81 Maika St 19 of 50 Listing Image for 81 Maika St 20 of 50 Listing Image for 81 Maika St 21 of 50 Listing Image for 81 Maika St 22 of 50 Listing Image for 81 Maika St 23 of 50 Listing Image for 81 Maika St 24 of 50 Listing Image for 81 Maika St 25 of 50 Listing Image for 81 Maika St 26 of 50 Listing Image for 81 Maika St 27 of 50 Listing Image for 81 Maika St 28 of 50 Listing Image for 81 Maika St 29 of 50 Listing Image for 81 Maika St 30 of 50 Listing Image for 81 Maika St 31 of 50 Listing Image for 81 Maika St 32 of 50 Listing Image for 81 Maika St 33 of 50 Listing Image for 81 Maika St 34 of 50 Listing Image for 81 Maika St 35 of 50 Listing Image for 81 Maika St 36 of 50 Listing Image for 81 Maika St 37 of 50 Listing Image for 81 Maika St 38 of 50 Listing Image for 81 Maika St 39 of 50 Listing Image for 81 Maika St 40 of 50 Listing Image for 81 Maika St 41 of 50 Listing Image for 81 Maika St 42 of 50 Listing Image for 81 Maika St 43 of 50 Listing Image for 81 Maika St 44 of 50 Listing Image for 81 Maika St 45 of 50 Listing Image for 81 Maika St 46 of 50 Listing Image for 81 Maika St 47 of 50 Listing Image for 81 Maika St 48 of 50 Listing Image for 81 Maika St 49 of 50 Listing Image for 81 Maika St 50 of 50

$3,700,000

↓ $150,000

Wailuku Country Estates

81 Maika St, Wailuku

4 Beds 5.5 Baths 4,171 SqFt Residential MLS® # 408564

Days on Market: 231

Commercial Prop of Maui LLC

Listing Image for 2757 S Kihei Rd 101 1 of 27 Listing Image for 2757 S Kihei Rd 101 2 of 27 Listing Image for 2757 S Kihei Rd 101 3 of 27 Listing Image for 2757 S Kihei Rd 101 4 of 27 Listing Image for 2757 S Kihei Rd 101 5 of 27 Listing Image for 2757 S Kihei Rd 101 6 of 27 Listing Image for 2757 S Kihei Rd 101 7 of 27 Listing Image for 2757 S Kihei Rd 101 8 of 27 Listing Image for 2757 S Kihei Rd 101 9 of 27 Listing Image for 2757 S Kihei Rd 101 10 of 27 Listing Image for 2757 S Kihei Rd 101 11 of 27 Listing Image for 2757 S Kihei Rd 101 12 of 27 Listing Image for 2757 S Kihei Rd 101 13 of 27 Listing Image for 2757 S Kihei Rd 101 14 of 27 Listing Image for 2757 S Kihei Rd 101 15 of 27 Listing Image for 2757 S Kihei Rd 101 16 of 27 Listing Image for 2757 S Kihei Rd 101 17 of 27 Listing Image for 2757 S Kihei Rd 101 18 of 27 Listing Image for 2757 S Kihei Rd 101 19 of 27 Listing Image for 2757 S Kihei Rd 101 20 of 27 Listing Image for 2757 S Kihei Rd 101 21 of 27 Listing Image for 2757 S Kihei Rd 101 22 of 27 Listing Image for 2757 S Kihei Rd 101 23 of 27 Listing Image for 2757 S Kihei Rd 101 24 of 27 Listing Image for 2757 S Kihei Rd 101 25 of 27 Listing Image for 2757 S Kihei Rd 101 26 of 27 Listing Image for 2757 S Kihei Rd 101 27 of 27

$1,475,000

Paradise Ridge Estates 101

2757 S Kihei Rd 101, Kihei

3 Beds 2 Baths 1,389 SqFt Residential MLS® # 408560

Days on Market: 231

Compass-W

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
Listing Image for 3943 Wailea Ekolu Pl 1 of 44 Listing Image for 3943 Wailea Ekolu Pl 2 of 44 Listing Image for 3943 Wailea Ekolu Pl 3 of 44 Listing Image for 3943 Wailea Ekolu Pl 4 of 44 Listing Image for 3943 Wailea Ekolu Pl 5 of 44 Listing Image for 3943 Wailea Ekolu Pl 6 of 44 Listing Image for 3943 Wailea Ekolu Pl 7 of 44 Listing Image for 3943 Wailea Ekolu Pl 8 of 44 Listing Image for 3943 Wailea Ekolu Pl 9 of 44 Listing Image for 3943 Wailea Ekolu Pl 10 of 44 Listing Image for 3943 Wailea Ekolu Pl 11 of 44 Listing Image for 3943 Wailea Ekolu Pl 12 of 44 Listing Image for 3943 Wailea Ekolu Pl 13 of 44 Listing Image for 3943 Wailea Ekolu Pl 14 of 44 Listing Image for 3943 Wailea Ekolu Pl 15 of 44 Listing Image for 3943 Wailea Ekolu Pl 16 of 44 Listing Image for 3943 Wailea Ekolu Pl 17 of 44 Listing Image for 3943 Wailea Ekolu Pl 18 of 44 Listing Image for 3943 Wailea Ekolu Pl 19 of 44 Listing Image for 3943 Wailea Ekolu Pl 20 of 44 Listing Image for 3943 Wailea Ekolu Pl 21 of 44 Listing Image for 3943 Wailea Ekolu Pl 22 of 44 Listing Image for 3943 Wailea Ekolu Pl 23 of 44 Listing Image for 3943 Wailea Ekolu Pl 24 of 44 Listing Image for 3943 Wailea Ekolu Pl 25 of 44 Listing Image for 3943 Wailea Ekolu Pl 26 of 44 Listing Image for 3943 Wailea Ekolu Pl 27 of 44 Listing Image for 3943 Wailea Ekolu Pl 28 of 44 Listing Image for 3943 Wailea Ekolu Pl 29 of 44 Listing Image for 3943 Wailea Ekolu Pl 30 of 44 Listing Image for 3943 Wailea Ekolu Pl 31 of 44 Listing Image for 3943 Wailea Ekolu Pl 32 of 44 Listing Image for 3943 Wailea Ekolu Pl 33 of 44 Listing Image for 3943 Wailea Ekolu Pl 34 of 44 Listing Image for 3943 Wailea Ekolu Pl 35 of 44 Listing Image for 3943 Wailea Ekolu Pl 36 of 44 Listing Image for 3943 Wailea Ekolu Pl 37 of 44 Listing Image for 3943 Wailea Ekolu Pl 38 of 44 Listing Image for 3943 Wailea Ekolu Pl 39 of 44 Listing Image for 3943 Wailea Ekolu Pl 40 of 44 Listing Image for 3943 Wailea Ekolu Pl 41 of 44 Listing Image for 3943 Wailea Ekolu Pl 42 of 44 Listing Image for 3943 Wailea Ekolu Pl 43 of 44 Listing Image for 3943 Wailea Ekolu Pl 44 of 44

$4,495,000

↓ $300,000

Wailea Golf Estates

3943 Wailea Ekolu Pl, Wailea/Makena

3 Beds 4 Baths 4,355 SqFt Residential MLS® # 408559

Days on Market: 231

Maui Real Estate Advisors LLC 808-875-4444

Listing Image for 3977 Wailea Ekolu Pl 1 of 40 Listing Image for 3977 Wailea Ekolu Pl 2 of 40 Listing Image for 3977 Wailea Ekolu Pl 3 of 40 Listing Image for 3977 Wailea Ekolu Pl 4 of 40 Listing Image for 3977 Wailea Ekolu Pl 5 of 40 Listing Image for 3977 Wailea Ekolu Pl 6 of 40 Listing Image for 3977 Wailea Ekolu Pl 7 of 40 Listing Image for 3977 Wailea Ekolu Pl 8 of 40 Listing Image for 3977 Wailea Ekolu Pl 9 of 40 Listing Image for 3977 Wailea Ekolu Pl 10 of 40 Listing Image for 3977 Wailea Ekolu Pl 11 of 40 Listing Image for 3977 Wailea Ekolu Pl 12 of 40 Listing Image for 3977 Wailea Ekolu Pl 13 of 40 Listing Image for 3977 Wailea Ekolu Pl 14 of 40 Listing Image for 3977 Wailea Ekolu Pl 15 of 40 Listing Image for 3977 Wailea Ekolu Pl 16 of 40 Listing Image for 3977 Wailea Ekolu Pl 17 of 40 Listing Image for 3977 Wailea Ekolu Pl 18 of 40 Listing Image for 3977 Wailea Ekolu Pl 19 of 40 Listing Image for 3977 Wailea Ekolu Pl 20 of 40 Listing Image for 3977 Wailea Ekolu Pl 21 of 40 Listing Image for 3977 Wailea Ekolu Pl 22 of 40 Listing Image for 3977 Wailea Ekolu Pl 23 of 40 Listing Image for 3977 Wailea Ekolu Pl 24 of 40 Listing Image for 3977 Wailea Ekolu Pl 25 of 40 Listing Image for 3977 Wailea Ekolu Pl 26 of 40 Listing Image for 3977 Wailea Ekolu Pl 27 of 40 Listing Image for 3977 Wailea Ekolu Pl 28 of 40 Listing Image for 3977 Wailea Ekolu Pl 29 of 40 Listing Image for 3977 Wailea Ekolu Pl 30 of 40 Listing Image for 3977 Wailea Ekolu Pl 31 of 40 Listing Image for 3977 Wailea Ekolu Pl 32 of 40 Listing Image for 3977 Wailea Ekolu Pl 33 of 40 Listing Image for 3977 Wailea Ekolu Pl 34 of 40 Listing Image for 3977 Wailea Ekolu Pl 35 of 40 Listing Image for 3977 Wailea Ekolu Pl 36 of 40 Listing Image for 3977 Wailea Ekolu Pl 37 of 40 Listing Image for 3977 Wailea Ekolu Pl 38 of 40 Listing Image for 3977 Wailea Ekolu Pl 39 of 40 Listing Image for 3977 Wailea Ekolu Pl 40 of 40

$6,950,000

↓ $250,000

Wailea Golf Estates

3977 Wailea Ekolu Pl, Wailea/Makena

4 Beds 6 Baths 4,079 SqFt Residential MLS® # 408558

Days on Market: 231

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

Short Term Rental
Listing Image for 50 Nohea Kai Dr 1-904 1 of 50 Listing Image for 50 Nohea Kai Dr 1-904 2 of 50 Listing Image for 50 Nohea Kai Dr 1-904 3 of 50 Listing Image for 50 Nohea Kai Dr 1-904 4 of 50 Listing Image for 50 Nohea Kai Dr 1-904 5 of 50 Listing Image for 50 Nohea Kai Dr 1-904 6 of 50 Listing Image for 50 Nohea Kai Dr 1-904 7 of 50 Listing Image for 50 Nohea Kai Dr 1-904 8 of 50 Listing Image for 50 Nohea Kai Dr 1-904 9 of 50 Listing Image for 50 Nohea Kai Dr 1-904 10 of 50 Listing Image for 50 Nohea Kai Dr 1-904 11 of 50 Listing Image for 50 Nohea Kai Dr 1-904 12 of 50 Listing Image for 50 Nohea Kai Dr 1-904 13 of 50 Listing Image for 50 Nohea Kai Dr 1-904 14 of 50 Listing Image for 50 Nohea Kai Dr 1-904 15 of 50 Listing Image for 50 Nohea Kai Dr 1-904 16 of 50 Listing Image for 50 Nohea Kai Dr 1-904 17 of 50 Listing Image for 50 Nohea Kai Dr 1-904 18 of 50 Listing Image for 50 Nohea Kai Dr 1-904 19 of 50 Listing Image for 50 Nohea Kai Dr 1-904 20 of 50 Listing Image for 50 Nohea Kai Dr 1-904 21 of 50 Listing Image for 50 Nohea Kai Dr 1-904 22 of 50 Listing Image for 50 Nohea Kai Dr 1-904 23 of 50 Listing Image for 50 Nohea Kai Dr 1-904 24 of 50 Listing Image for 50 Nohea Kai Dr 1-904 25 of 50 Listing Image for 50 Nohea Kai Dr 1-904 26 of 50 Listing Image for 50 Nohea Kai Dr 1-904 27 of 50 Listing Image for 50 Nohea Kai Dr 1-904 28 of 50 Listing Image for 50 Nohea Kai Dr 1-904 29 of 50 Listing Image for 50 Nohea Kai Dr 1-904 30 of 50 Listing Image for 50 Nohea Kai Dr 1-904 31 of 50 Listing Image for 50 Nohea Kai Dr 1-904 32 of 50 Listing Image for 50 Nohea Kai Dr 1-904 33 of 50 Listing Image for 50 Nohea Kai Dr 1-904 34 of 50 Listing Image for 50 Nohea Kai Dr 1-904 35 of 50 Listing Image for 50 Nohea Kai Dr 1-904 36 of 50 Listing Image for 50 Nohea Kai Dr 1-904 37 of 50 Listing Image for 50 Nohea Kai Dr 1-904 38 of 50 Listing Image for 50 Nohea Kai Dr 1-904 39 of 50 Listing Image for 50 Nohea Kai Dr 1-904 40 of 50 Listing Image for 50 Nohea Kai Dr 1-904 41 of 50 Listing Image for 50 Nohea Kai Dr 1-904 42 of 50 Listing Image for 50 Nohea Kai Dr 1-904 43 of 50 Listing Image for 50 Nohea Kai Dr 1-904 44 of 50 Listing Image for 50 Nohea Kai Dr 1-904 45 of 50 Listing Image for 50 Nohea Kai Dr 1-904 46 of 50 Listing Image for 50 Nohea Kai Dr 1-904 47 of 50 Listing Image for 50 Nohea Kai Dr 1-904 48 of 50 Listing Image for 50 Nohea Kai Dr 1-904 49 of 50 Listing Image for 50 Nohea Kai Dr 1-904 50 of 50

$2,999,850

↓ $300,150

Kaanapali Alii 1-904

50 Nohea Kai Dr 1-904, Kaanapali

2 Beds 2 Baths 1,523 SqFt Residential MLS® # 408557

Days on Market: 231

Keller Williams Realty Maui-Ka Cell: 808-385-0882

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: 04/08/2026
Listing Image for 2385 S Kihei Rd 409 1 of 34 Listing Image for 2385 S Kihei Rd 409 2 of 34 Listing Image for 2385 S Kihei Rd 409 3 of 34 Listing Image for 2385 S Kihei Rd 409 4 of 34 Listing Image for 2385 S Kihei Rd 409 5 of 34 Listing Image for 2385 S Kihei Rd 409 6 of 34 Listing Image for 2385 S Kihei Rd 409 7 of 34 Listing Image for 2385 S Kihei Rd 409 8 of 34 Listing Image for 2385 S Kihei Rd 409 9 of 34 Listing Image for 2385 S Kihei Rd 409 10 of 34 Listing Image for 2385 S Kihei Rd 409 11 of 34 Listing Image for 2385 S Kihei Rd 409 12 of 34 Listing Image for 2385 S Kihei Rd 409 13 of 34 Listing Image for 2385 S Kihei Rd 409 14 of 34 Listing Image for 2385 S Kihei Rd 409 15 of 34 Listing Image for 2385 S Kihei Rd 409 16 of 34 Listing Image for 2385 S Kihei Rd 409 17 of 34 Listing Image for 2385 S Kihei Rd 409 18 of 34 Listing Image for 2385 S Kihei Rd 409 19 of 34 Listing Image for 2385 S Kihei Rd 409 20 of 34 Listing Image for 2385 S Kihei Rd 409 21 of 34 Listing Image for 2385 S Kihei Rd 409 22 of 34 Listing Image for 2385 S Kihei Rd 409 23 of 34 Listing Image for 2385 S Kihei Rd 409 24 of 34 Listing Image for 2385 S Kihei Rd 409 25 of 34 Listing Image for 2385 S Kihei Rd 409 26 of 34 Listing Image for 2385 S Kihei Rd 409 27 of 34 Listing Image for 2385 S Kihei Rd 409 28 of 34 Listing Image for 2385 S Kihei Rd 409 29 of 34 Listing Image for 2385 S Kihei Rd 409 30 of 34 Listing Image for 2385 S Kihei Rd 409 31 of 34 Listing Image for 2385 S Kihei Rd 409 32 of 34 Listing Image for 2385 S Kihei Rd 409 33 of 34 Listing Image for 2385 S Kihei Rd 409 34 of 34

$814,000

↓ $81,000

Kamaole Beach Royale 409

2385 S Kihei Rd 409, Kihei

1 Bed 1 Bath 580 SqFt Residential MLS® # 407586 Date Sold: April 8, 2026
Sold
Closed: 10/30/2025
20 Kakawahie St 84, Wailuku

$950,000

Kamani at Kehalani 84

20 Kakawahie St 84, Wailuku

3 Beds 2.5 Baths 1,457 SqFt Residential MLS® # 407580 Date Sold: October 30, 2025
Sold
Closed: 02/05/2026
Listing Image for 52 Kai Malu Dr 102 (9b) 1 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 2 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 3 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 4 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 5 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 6 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 7 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 8 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 9 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 10 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 11 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 12 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 13 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 14 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 15 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 16 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 17 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 18 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 19 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 20 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 21 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 22 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 23 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 24 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 25 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 26 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 27 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 28 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 29 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 30 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 31 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 32 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 33 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 34 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 35 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 36 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 37 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 38 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 39 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 40 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 41 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 42 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 43 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 44 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 45 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 46 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 47 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 48 of 49 Listing Image for 52 Kai Malu Dr 102 (9b) 49 of 49

$2,650,000

La'i Loa 102 (9B)

52 Kai Malu Dr 102 (9b), Wailea/Makena

2 Beds 2 Baths 1,374 SqFt Residential MLS® # 407579 Date Sold: February 5, 2026
Sold
Closed: 12/24/2025
Listing Image for 371 Pualoa Nani Pl Lot 24 1 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 2 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 3 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 4 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 5 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 6 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 7 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 8 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 9 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 10 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 11 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 12 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 13 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 14 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 15 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 16 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 17 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 18 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 19 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 20 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 21 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 22 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 23 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 24 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 25 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 26 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 27 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 28 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 29 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 30 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 31 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 32 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 33 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 34 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 35 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 36 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 37 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 38 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 39 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 40 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 41 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 42 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 43 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 44 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 45 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 46 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 47 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 48 of 49 Listing Image for 371 Pualoa Nani Pl Lot 24 49 of 49

$2,795,000

Wailea Pualani

371 Pualoa Nani Pl Lot 24, Wailea/Makena

3 Beds 3 Baths 2,354 SqFt Residential MLS® # 407577 Date Sold: December 24, 2025
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: 02/09/2026
Listing Image for 52 Kai Malu Dr 202 (9d) 1 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 2 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 3 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 4 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 5 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 6 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 7 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 8 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 9 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 10 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 11 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 12 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 13 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 14 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 15 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 16 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 17 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 18 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 19 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 20 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 21 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 22 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 23 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 24 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 25 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 26 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 27 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 28 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 29 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 30 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 31 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 32 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 33 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 34 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 35 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 36 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 37 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 38 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 39 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 40 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 41 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 42 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 43 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 44 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 45 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 46 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 47 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 48 of 49 Listing Image for 52 Kai Malu Dr 202 (9d) 49 of 49

$2,800,000

La'i Loa 202 (9D)

52 Kai Malu Dr 202 (9d), Wailea/Makena

2 Beds 2 Baths 1,374 SqFt Residential MLS® # 407576 Date Sold: February 9, 2026
Sold
Closed: 04/27/2026
Listing Image for 94 Laukahi St 1 of 50 Listing Image for 94 Laukahi St 2 of 50 Listing Image for 94 Laukahi St 3 of 50 Listing Image for 94 Laukahi St 4 of 50 Listing Image for 94 Laukahi St 5 of 50 Listing Image for 94 Laukahi St 6 of 50 Listing Image for 94 Laukahi St 7 of 50 Listing Image for 94 Laukahi St 8 of 50 Listing Image for 94 Laukahi St 9 of 50 Listing Image for 94 Laukahi St 10 of 50 Listing Image for 94 Laukahi St 11 of 50 Listing Image for 94 Laukahi St 12 of 50 Listing Image for 94 Laukahi St 13 of 50 Listing Image for 94 Laukahi St 14 of 50 Listing Image for 94 Laukahi St 15 of 50 Listing Image for 94 Laukahi St 16 of 50 Listing Image for 94 Laukahi St 17 of 50 Listing Image for 94 Laukahi St 18 of 50 Listing Image for 94 Laukahi St 19 of 50 Listing Image for 94 Laukahi St 20 of 50 Listing Image for 94 Laukahi St 21 of 50 Listing Image for 94 Laukahi St 22 of 50 Listing Image for 94 Laukahi St 23 of 50 Listing Image for 94 Laukahi St 24 of 50 Listing Image for 94 Laukahi St 25 of 50 Listing Image for 94 Laukahi St 26 of 50 Listing Image for 94 Laukahi St 27 of 50 Listing Image for 94 Laukahi St 28 of 50 Listing Image for 94 Laukahi St 29 of 50 Listing Image for 94 Laukahi St 30 of 50 Listing Image for 94 Laukahi St 31 of 50 Listing Image for 94 Laukahi St 32 of 50 Listing Image for 94 Laukahi St 33 of 50 Listing Image for 94 Laukahi St 34 of 50 Listing Image for 94 Laukahi St 35 of 50 Listing Image for 94 Laukahi St 36 of 50 Listing Image for 94 Laukahi St 37 of 50 Listing Image for 94 Laukahi St 38 of 50 Listing Image for 94 Laukahi St 39 of 50 Listing Image for 94 Laukahi St 40 of 50 Listing Image for 94 Laukahi St 41 of 50 Listing Image for 94 Laukahi St 42 of 50 Listing Image for 94 Laukahi St 43 of 50 Listing Image for 94 Laukahi St 44 of 50 Listing Image for 94 Laukahi St 45 of 50 Listing Image for 94 Laukahi St 46 of 50 Listing Image for 94 Laukahi St 47 of 50 Listing Image for 94 Laukahi St 48 of 50 Listing Image for 94 Laukahi St 49 of 50 Listing Image for 94 Laukahi St 50 of 50

$1,880,000

↓ $219,000

Moana Estates

94 Laukahi St, Kihei

4 Beds 3 Baths 2,616 SqFt Residential MLS® # 407560 Date Sold: April 27, 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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