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 1050 Kapukaulua Pl 1 of 42 Listing Image for 1050 Kapukaulua Pl 2 of 42 Listing Image for 1050 Kapukaulua Pl 3 of 42 Listing Image for 1050 Kapukaulua Pl 4 of 42 Listing Image for 1050 Kapukaulua Pl 5 of 42 Listing Image for 1050 Kapukaulua Pl 6 of 42 Listing Image for 1050 Kapukaulua Pl 7 of 42 Listing Image for 1050 Kapukaulua Pl 8 of 42 Listing Image for 1050 Kapukaulua Pl 9 of 42 Listing Image for 1050 Kapukaulua Pl 10 of 42 Listing Image for 1050 Kapukaulua Pl 11 of 42 Listing Image for 1050 Kapukaulua Pl 12 of 42 Listing Image for 1050 Kapukaulua Pl 13 of 42 Listing Image for 1050 Kapukaulua Pl 14 of 42 Listing Image for 1050 Kapukaulua Pl 15 of 42 Listing Image for 1050 Kapukaulua Pl 16 of 42 Listing Image for 1050 Kapukaulua Pl 17 of 42 Listing Image for 1050 Kapukaulua Pl 18 of 42 Listing Image for 1050 Kapukaulua Pl 19 of 42 Listing Image for 1050 Kapukaulua Pl 20 of 42 Listing Image for 1050 Kapukaulua Pl 21 of 42 Listing Image for 1050 Kapukaulua Pl 22 of 42 Listing Image for 1050 Kapukaulua Pl 23 of 42 Listing Image for 1050 Kapukaulua Pl 24 of 42 Listing Image for 1050 Kapukaulua Pl 25 of 42 Listing Image for 1050 Kapukaulua Pl 26 of 42 Listing Image for 1050 Kapukaulua Pl 27 of 42 Listing Image for 1050 Kapukaulua Pl 28 of 42 Listing Image for 1050 Kapukaulua Pl 29 of 42 Listing Image for 1050 Kapukaulua Pl 30 of 42 Listing Image for 1050 Kapukaulua Pl 31 of 42 Listing Image for 1050 Kapukaulua Pl 32 of 42 Listing Image for 1050 Kapukaulua Pl 33 of 42 Listing Image for 1050 Kapukaulua Pl 34 of 42 Listing Image for 1050 Kapukaulua Pl 35 of 42 Listing Image for 1050 Kapukaulua Pl 36 of 42 Listing Image for 1050 Kapukaulua Pl 37 of 42 Listing Image for 1050 Kapukaulua Pl 38 of 42 Listing Image for 1050 Kapukaulua Pl 39 of 42 Listing Image for 1050 Kapukaulua Pl 40 of 42 Listing Image for 1050 Kapukaulua Pl 41 of 42 Listing Image for 1050 Kapukaulua Pl 42 of 42

$6,800,000

↓ $450,000

Spreckelsville/Paia/Kuau

1050 Kapukaulua Pl, Spreckelsville/Paia/Kuau

4 Beds 2.5 Baths 2,606 SqFt Residential MLS® # 407207

Days on Market: 360

Island Sotheby's International Realty(M) Cell: 808-870-4114

Short Term Rental
Listing Image for 50 Nohea Kai Dr 2-305 1 of 26 Listing Image for 50 Nohea Kai Dr 2-305 2 of 26 Listing Image for 50 Nohea Kai Dr 2-305 3 of 26 Listing Image for 50 Nohea Kai Dr 2-305 4 of 26 Listing Image for 50 Nohea Kai Dr 2-305 5 of 26 Listing Image for 50 Nohea Kai Dr 2-305 6 of 26 Listing Image for 50 Nohea Kai Dr 2-305 7 of 26 Listing Image for 50 Nohea Kai Dr 2-305 8 of 26 Listing Image for 50 Nohea Kai Dr 2-305 9 of 26 Listing Image for 50 Nohea Kai Dr 2-305 10 of 26 Listing Image for 50 Nohea Kai Dr 2-305 11 of 26 Listing Image for 50 Nohea Kai Dr 2-305 12 of 26 Listing Image for 50 Nohea Kai Dr 2-305 13 of 26 Listing Image for 50 Nohea Kai Dr 2-305 14 of 26 Listing Image for 50 Nohea Kai Dr 2-305 15 of 26 Listing Image for 50 Nohea Kai Dr 2-305 16 of 26 Listing Image for 50 Nohea Kai Dr 2-305 17 of 26 Listing Image for 50 Nohea Kai Dr 2-305 18 of 26 Listing Image for 50 Nohea Kai Dr 2-305 19 of 26 Listing Image for 50 Nohea Kai Dr 2-305 20 of 26 Listing Image for 50 Nohea Kai Dr 2-305 21 of 26 Listing Image for 50 Nohea Kai Dr 2-305 22 of 26 Listing Image for 50 Nohea Kai Dr 2-305 23 of 26 Listing Image for 50 Nohea Kai Dr 2-305 24 of 26 Listing Image for 50 Nohea Kai Dr 2-305 25 of 26 Listing Image for 50 Nohea Kai Dr 2-305 26 of 26

$2,395,000

↓ $400,000

Kaanapali Alii 2-305

50 Nohea Kai Dr 2-305, Kaanapali

2 Beds 2 Baths 1,650 SqFt Residential MLS® # 407104

Days on Market: 370

Coldwell Banker Island Prop-KP Cell: 808-276-6443

Listing Image for 214 Kulamanu Cir 1 of 37 Listing Image for 214 Kulamanu Cir 2 of 37 Listing Image for 214 Kulamanu Cir 3 of 37 Listing Image for 214 Kulamanu Cir 4 of 37 Listing Image for 214 Kulamanu Cir 5 of 37 Listing Image for 214 Kulamanu Cir 6 of 37 Listing Image for 214 Kulamanu Cir 7 of 37 Listing Image for 214 Kulamanu Cir 8 of 37 Listing Image for 214 Kulamanu Cir 9 of 37 Listing Image for 214 Kulamanu Cir 10 of 37 Listing Image for 214 Kulamanu Cir 11 of 37 Listing Image for 214 Kulamanu Cir 12 of 37 Listing Image for 214 Kulamanu Cir 13 of 37 Listing Image for 214 Kulamanu Cir 14 of 37 Listing Image for 214 Kulamanu Cir 15 of 37 Listing Image for 214 Kulamanu Cir 16 of 37 Listing Image for 214 Kulamanu Cir 17 of 37 Listing Image for 214 Kulamanu Cir 18 of 37 Listing Image for 214 Kulamanu Cir 19 of 37 Listing Image for 214 Kulamanu Cir 20 of 37 Listing Image for 214 Kulamanu Cir 21 of 37 Listing Image for 214 Kulamanu Cir 22 of 37 Listing Image for 214 Kulamanu Cir 23 of 37 Listing Image for 214 Kulamanu Cir 24 of 37 Listing Image for 214 Kulamanu Cir 25 of 37 Listing Image for 214 Kulamanu Cir 26 of 37 Listing Image for 214 Kulamanu Cir 27 of 37 Listing Image for 214 Kulamanu Cir 28 of 37 Listing Image for 214 Kulamanu Cir 29 of 37 Listing Image for 214 Kulamanu Cir 30 of 37 Listing Image for 214 Kulamanu Cir 31 of 37 Listing Image for 214 Kulamanu Cir 32 of 37 Listing Image for 214 Kulamanu Cir 33 of 37 Listing Image for 214 Kulamanu Cir 34 of 37 Listing Image for 214 Kulamanu Cir 35 of 37 Listing Image for 214 Kulamanu Cir 36 of 37 Listing Image for 214 Kulamanu Cir 37 of 37

$2,200,000

↓ $100,000

Kula/Ulupalakua/Kanaio

214 Kulamanu Cir, Kula/Ulupalakua/Kanaio

4 Beds 4 Baths 2,824 SqFt Residential MLS® # 407108

Days on Market: 371

Coldwell Banker Island Prop(P) Cell: 808-205-2175

Listing Image for 454 Hoolawa Rd 1 of 43 Listing Image for 454 Hoolawa Rd 2 of 43 Listing Image for 454 Hoolawa Rd 3 of 43 Listing Image for 454 Hoolawa Rd 4 of 43 Listing Image for 454 Hoolawa Rd 5 of 43 Listing Image for 454 Hoolawa Rd 6 of 43 Listing Image for 454 Hoolawa Rd 7 of 43 Listing Image for 454 Hoolawa Rd 8 of 43 Listing Image for 454 Hoolawa Rd 9 of 43 Listing Image for 454 Hoolawa Rd 10 of 43 Listing Image for 454 Hoolawa Rd 11 of 43 Listing Image for 454 Hoolawa Rd 12 of 43 Listing Image for 454 Hoolawa Rd 13 of 43 Listing Image for 454 Hoolawa Rd 14 of 43 Listing Image for 454 Hoolawa Rd 15 of 43 Listing Image for 454 Hoolawa Rd 16 of 43 Listing Image for 454 Hoolawa Rd 17 of 43 Listing Image for 454 Hoolawa Rd 18 of 43 Listing Image for 454 Hoolawa Rd 19 of 43 Listing Image for 454 Hoolawa Rd 20 of 43 Listing Image for 454 Hoolawa Rd 21 of 43 Listing Image for 454 Hoolawa Rd 22 of 43 Listing Image for 454 Hoolawa Rd 23 of 43 Listing Image for 454 Hoolawa Rd 24 of 43 Listing Image for 454 Hoolawa Rd 25 of 43 Listing Image for 454 Hoolawa Rd 26 of 43 Listing Image for 454 Hoolawa Rd 27 of 43 Listing Image for 454 Hoolawa Rd 28 of 43 Listing Image for 454 Hoolawa Rd 29 of 43 Listing Image for 454 Hoolawa Rd 30 of 43 Listing Image for 454 Hoolawa Rd 31 of 43 Listing Image for 454 Hoolawa Rd 32 of 43 Listing Image for 454 Hoolawa Rd 33 of 43 Listing Image for 454 Hoolawa Rd 34 of 43 Listing Image for 454 Hoolawa Rd 35 of 43 Listing Image for 454 Hoolawa Rd 36 of 43 Listing Image for 454 Hoolawa Rd 37 of 43 Listing Image for 454 Hoolawa Rd 38 of 43 Listing Image for 454 Hoolawa Rd 39 of 43 Listing Image for 454 Hoolawa Rd 40 of 43 Listing Image for 454 Hoolawa Rd 41 of 43 Listing Image for 454 Hoolawa Rd 42 of 43 Listing Image for 454 Hoolawa Rd 43 of 43

$5,500,000

Haiku

454 Hoolawa Rd, Haiku

2 Beds 2 Baths 2,118 SqFt Residential MLS® # 407170

Days on Market: 364

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

Listing Image for 73 N Kihei Rd 602 1 of 47 Listing Image for 73 N Kihei Rd 602 2 of 47 Listing Image for 73 N Kihei Rd 602 3 of 47 Listing Image for 73 N Kihei Rd 602 4 of 47 Listing Image for 73 N Kihei Rd 602 5 of 47 Listing Image for 73 N Kihei Rd 602 6 of 47 Listing Image for 73 N Kihei Rd 602 7 of 47 Listing Image for 73 N Kihei Rd 602 8 of 47 Listing Image for 73 N Kihei Rd 602 9 of 47 Listing Image for 73 N Kihei Rd 602 10 of 47 Listing Image for 73 N Kihei Rd 602 11 of 47 Listing Image for 73 N Kihei Rd 602 12 of 47 Listing Image for 73 N Kihei Rd 602 13 of 47 Listing Image for 73 N Kihei Rd 602 14 of 47 Listing Image for 73 N Kihei Rd 602 15 of 47 Listing Image for 73 N Kihei Rd 602 16 of 47 Listing Image for 73 N Kihei Rd 602 17 of 47 Listing Image for 73 N Kihei Rd 602 18 of 47 Listing Image for 73 N Kihei Rd 602 19 of 47 Listing Image for 73 N Kihei Rd 602 20 of 47 Listing Image for 73 N Kihei Rd 602 21 of 47 Listing Image for 73 N Kihei Rd 602 22 of 47 Listing Image for 73 N Kihei Rd 602 23 of 47 Listing Image for 73 N Kihei Rd 602 24 of 47 Listing Image for 73 N Kihei Rd 602 25 of 47 Listing Image for 73 N Kihei Rd 602 26 of 47 Listing Image for 73 N Kihei Rd 602 27 of 47 Listing Image for 73 N Kihei Rd 602 28 of 47 Listing Image for 73 N Kihei Rd 602 29 of 47 Listing Image for 73 N Kihei Rd 602 30 of 47 Listing Image for 73 N Kihei Rd 602 31 of 47 Listing Image for 73 N Kihei Rd 602 32 of 47 Listing Image for 73 N Kihei Rd 602 33 of 47 Listing Image for 73 N Kihei Rd 602 34 of 47 Listing Image for 73 N Kihei Rd 602 35 of 47 Listing Image for 73 N Kihei Rd 602 36 of 47 Listing Image for 73 N Kihei Rd 602 37 of 47 Listing Image for 73 N Kihei Rd 602 38 of 47 Listing Image for 73 N Kihei Rd 602 39 of 47 Listing Image for 73 N Kihei Rd 602 40 of 47 Listing Image for 73 N Kihei Rd 602 41 of 47 Listing Image for 73 N Kihei Rd 602 42 of 47 Listing Image for 73 N Kihei Rd 602 43 of 47 Listing Image for 73 N Kihei Rd 602 44 of 47 Listing Image for 73 N Kihei Rd 602 45 of 47 Listing Image for 73 N Kihei Rd 602 46 of 47 Listing Image for 73 N Kihei Rd 602 47 of 47

$999,000

Nani Kai Hale 602

73 N Kihei Rd 602, Kihei

2 Beds 2 Baths 828 SqFt Residential MLS® # 407125

Days on Market: 370

Coldwell Banker Island Prop-Ku 808-281-8083

Listing Image for 4000 Wailea Alanui Dr 2802 1 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 2 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 3 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 4 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 5 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 6 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 7 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 8 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 9 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 10 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 11 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 12 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 13 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 14 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 15 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 16 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 17 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 18 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 19 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 20 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 21 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 22 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 23 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 24 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 25 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 26 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 27 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 28 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 29 of 30 Listing Image for 4000 Wailea Alanui Dr 2802 30 of 30

$4,750,000

↓ $150,000

Wailea Point 2802

4000 Wailea Alanui Dr 2802, Wailea/Makena

2 Beds 2 Baths 1,808 SqFt Residential MLS® # 407132

Days on Market: 367

Wailea Point Realty, Inc. realty@waileapoint.com

Short Term Rental
Listing Image for 5295 Lower Honoapiilani Rd B39 1 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 2 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 3 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 4 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 5 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 6 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 7 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 8 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 9 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 10 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 11 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 12 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 13 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 14 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 15 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 16 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 17 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 18 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 19 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 20 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 21 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 22 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 23 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 24 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 25 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 26 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 27 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 28 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 29 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 30 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 31 of 32 Listing Image for 5295 Lower Honoapiilani Rd B39 32 of 32

$948,000

↓ $39,000

Napili Point B39

5295 Lower Honoapiilani Rd B39, Napili/Kahana/Honokowai

1 Bed 1 Bath 718 SqFt Residential MLS® # 407179

Days on Market: 363

Coldwell Banker Island Prop-KP Cell: 808-463-2445

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: 10/24/2025
Listing Image for 2541 Mokuhau Rd B 1 of 28 Listing Image for 2541 Mokuhau Rd B 2 of 28 Listing Image for 2541 Mokuhau Rd B 3 of 28 Listing Image for 2541 Mokuhau Rd B 4 of 28 Listing Image for 2541 Mokuhau Rd B 5 of 28 Listing Image for 2541 Mokuhau Rd B 6 of 28 Listing Image for 2541 Mokuhau Rd B 7 of 28 Listing Image for 2541 Mokuhau Rd B 8 of 28 Listing Image for 2541 Mokuhau Rd B 9 of 28 Listing Image for 2541 Mokuhau Rd B 10 of 28 Listing Image for 2541 Mokuhau Rd B 11 of 28 Listing Image for 2541 Mokuhau Rd B 12 of 28 Listing Image for 2541 Mokuhau Rd B 13 of 28 Listing Image for 2541 Mokuhau Rd B 14 of 28 Listing Image for 2541 Mokuhau Rd B 15 of 28 Listing Image for 2541 Mokuhau Rd B 16 of 28 Listing Image for 2541 Mokuhau Rd B 17 of 28 Listing Image for 2541 Mokuhau Rd B 18 of 28 Listing Image for 2541 Mokuhau Rd B 19 of 28 Listing Image for 2541 Mokuhau Rd B 20 of 28 Listing Image for 2541 Mokuhau Rd B 21 of 28 Listing Image for 2541 Mokuhau Rd B 22 of 28 Listing Image for 2541 Mokuhau Rd B 23 of 28 Listing Image for 2541 Mokuhau Rd B 24 of 28 Listing Image for 2541 Mokuhau Rd B 25 of 28 Listing Image for 2541 Mokuhau Rd B 26 of 28 Listing Image for 2541 Mokuhau Rd B 27 of 28 Listing Image for 2541 Mokuhau Rd B 28 of 28

$1,050,000

Iao Valley Homesteads

2541 Mokuhau Rd B, Wailuku

1 Bed 1 Bath 490 SqFt Residential MLS® # 406966 Date Sold: October 24, 2025
Sold
Closed: 03/23/2026
Listing Image for 3950 Kalai Waa St W201 1 of 50 Listing Image for 3950 Kalai Waa St W201 2 of 50 Listing Image for 3950 Kalai Waa St W201 3 of 50 Listing Image for 3950 Kalai Waa St W201 4 of 50 Listing Image for 3950 Kalai Waa St W201 5 of 50 Listing Image for 3950 Kalai Waa St W201 6 of 50 Listing Image for 3950 Kalai Waa St W201 7 of 50 Listing Image for 3950 Kalai Waa St W201 8 of 50 Listing Image for 3950 Kalai Waa St W201 9 of 50 Listing Image for 3950 Kalai Waa St W201 10 of 50 Listing Image for 3950 Kalai Waa St W201 11 of 50 Listing Image for 3950 Kalai Waa St W201 12 of 50 Listing Image for 3950 Kalai Waa St W201 13 of 50 Listing Image for 3950 Kalai Waa St W201 14 of 50 Listing Image for 3950 Kalai Waa St W201 15 of 50 Listing Image for 3950 Kalai Waa St W201 16 of 50 Listing Image for 3950 Kalai Waa St W201 17 of 50 Listing Image for 3950 Kalai Waa St W201 18 of 50 Listing Image for 3950 Kalai Waa St W201 19 of 50 Listing Image for 3950 Kalai Waa St W201 20 of 50 Listing Image for 3950 Kalai Waa St W201 21 of 50 Listing Image for 3950 Kalai Waa St W201 22 of 50 Listing Image for 3950 Kalai Waa St W201 23 of 50 Listing Image for 3950 Kalai Waa St W201 24 of 50 Listing Image for 3950 Kalai Waa St W201 25 of 50 Listing Image for 3950 Kalai Waa St W201 26 of 50 Listing Image for 3950 Kalai Waa St W201 27 of 50 Listing Image for 3950 Kalai Waa St W201 28 of 50 Listing Image for 3950 Kalai Waa St W201 29 of 50 Listing Image for 3950 Kalai Waa St W201 30 of 50 Listing Image for 3950 Kalai Waa St W201 31 of 50 Listing Image for 3950 Kalai Waa St W201 32 of 50 Listing Image for 3950 Kalai Waa St W201 33 of 50 Listing Image for 3950 Kalai Waa St W201 34 of 50 Listing Image for 3950 Kalai Waa St W201 35 of 50 Listing Image for 3950 Kalai Waa St W201 36 of 50 Listing Image for 3950 Kalai Waa St W201 37 of 50 Listing Image for 3950 Kalai Waa St W201 38 of 50 Listing Image for 3950 Kalai Waa St W201 39 of 50 Listing Image for 3950 Kalai Waa St W201 40 of 50 Listing Image for 3950 Kalai Waa St W201 41 of 50 Listing Image for 3950 Kalai Waa St W201 42 of 50 Listing Image for 3950 Kalai Waa St W201 43 of 50 Listing Image for 3950 Kalai Waa St W201 44 of 50 Listing Image for 3950 Kalai Waa St W201 45 of 50 Listing Image for 3950 Kalai Waa St W201 46 of 50 Listing Image for 3950 Kalai Waa St W201 47 of 50 Listing Image for 3950 Kalai Waa St W201 48 of 50 Listing Image for 3950 Kalai Waa St W201 49 of 50 Listing Image for 3950 Kalai Waa St W201 50 of 50

$1,159,000

↓ $65,999

Wailea Fairway Villas W201

3950 Kalai Waa St W201, Wailea/Makena

2 Beds 2 Baths 949 SqFt Residential MLS® # 407061 Date Sold: March 23, 2026
Sold
Closed: 10/06/2025
Listing Image for 69 Aliilani Pl 1 of 50 Listing Image for 69 Aliilani Pl 2 of 50 Listing Image for 69 Aliilani Pl 3 of 50 Listing Image for 69 Aliilani Pl 4 of 50 Listing Image for 69 Aliilani Pl 5 of 50 Listing Image for 69 Aliilani Pl 6 of 50 Listing Image for 69 Aliilani Pl 7 of 50 Listing Image for 69 Aliilani Pl 8 of 50 Listing Image for 69 Aliilani Pl 9 of 50 Listing Image for 69 Aliilani Pl 10 of 50 Listing Image for 69 Aliilani Pl 11 of 50 Listing Image for 69 Aliilani Pl 12 of 50 Listing Image for 69 Aliilani Pl 13 of 50 Listing Image for 69 Aliilani Pl 14 of 50 Listing Image for 69 Aliilani Pl 15 of 50 Listing Image for 69 Aliilani Pl 16 of 50 Listing Image for 69 Aliilani Pl 17 of 50 Listing Image for 69 Aliilani Pl 18 of 50 Listing Image for 69 Aliilani Pl 19 of 50 Listing Image for 69 Aliilani Pl 20 of 50 Listing Image for 69 Aliilani Pl 21 of 50 Listing Image for 69 Aliilani Pl 22 of 50 Listing Image for 69 Aliilani Pl 23 of 50 Listing Image for 69 Aliilani Pl 24 of 50 Listing Image for 69 Aliilani Pl 25 of 50 Listing Image for 69 Aliilani Pl 26 of 50 Listing Image for 69 Aliilani Pl 27 of 50 Listing Image for 69 Aliilani Pl 28 of 50 Listing Image for 69 Aliilani Pl 29 of 50 Listing Image for 69 Aliilani Pl 30 of 50 Listing Image for 69 Aliilani Pl 31 of 50 Listing Image for 69 Aliilani Pl 32 of 50 Listing Image for 69 Aliilani Pl 33 of 50 Listing Image for 69 Aliilani Pl 34 of 50 Listing Image for 69 Aliilani Pl 35 of 50 Listing Image for 69 Aliilani Pl 36 of 50 Listing Image for 69 Aliilani Pl 37 of 50 Listing Image for 69 Aliilani Pl 38 of 50 Listing Image for 69 Aliilani Pl 39 of 50 Listing Image for 69 Aliilani Pl 40 of 50 Listing Image for 69 Aliilani Pl 41 of 50 Listing Image for 69 Aliilani Pl 42 of 50 Listing Image for 69 Aliilani Pl 43 of 50 Listing Image for 69 Aliilani Pl 44 of 50 Listing Image for 69 Aliilani Pl 45 of 50 Listing Image for 69 Aliilani Pl 46 of 50 Listing Image for 69 Aliilani Pl 47 of 50 Listing Image for 69 Aliilani Pl 48 of 50 Listing Image for 69 Aliilani Pl 49 of 50 Listing Image for 69 Aliilani Pl 50 of 50

$985,000

Kihei

69 Aliilani Pl, Kihei

3 Beds 1 Bath 864 SqFt Residential MLS® # 407013 Date Sold: October 6, 2025
Sold
Closed: 12/16/2025
314 Hoohana St, Kahului

$1,500,000

Kahului

314 Hoohana St, Kahului

0 Beds 0 Baths 0 SqFt Commercial Sale MLS® # 407050 Date Sold: December 16, 2025
Sold
Closed: 03/31/2026
Listing Image for 1865 Kalia Way 1 of 50 Listing Image for 1865 Kalia Way 2 of 50 Listing Image for 1865 Kalia Way 3 of 50 Listing Image for 1865 Kalia Way 4 of 50 Listing Image for 1865 Kalia Way 5 of 50 Listing Image for 1865 Kalia Way 6 of 50 Listing Image for 1865 Kalia Way 7 of 50 Listing Image for 1865 Kalia Way 8 of 50 Listing Image for 1865 Kalia Way 9 of 50 Listing Image for 1865 Kalia Way 10 of 50 Listing Image for 1865 Kalia Way 11 of 50 Listing Image for 1865 Kalia Way 12 of 50 Listing Image for 1865 Kalia Way 13 of 50 Listing Image for 1865 Kalia Way 14 of 50 Listing Image for 1865 Kalia Way 15 of 50 Listing Image for 1865 Kalia Way 16 of 50 Listing Image for 1865 Kalia Way 17 of 50 Listing Image for 1865 Kalia Way 18 of 50 Listing Image for 1865 Kalia Way 19 of 50 Listing Image for 1865 Kalia Way 20 of 50 Listing Image for 1865 Kalia Way 21 of 50 Listing Image for 1865 Kalia Way 22 of 50 Listing Image for 1865 Kalia Way 23 of 50 Listing Image for 1865 Kalia Way 24 of 50 Listing Image for 1865 Kalia Way 25 of 50 Listing Image for 1865 Kalia Way 26 of 50 Listing Image for 1865 Kalia Way 27 of 50 Listing Image for 1865 Kalia Way 28 of 50 Listing Image for 1865 Kalia Way 29 of 50 Listing Image for 1865 Kalia Way 30 of 50 Listing Image for 1865 Kalia Way 31 of 50 Listing Image for 1865 Kalia Way 32 of 50 Listing Image for 1865 Kalia Way 33 of 50 Listing Image for 1865 Kalia Way 34 of 50 Listing Image for 1865 Kalia Way 35 of 50 Listing Image for 1865 Kalia Way 36 of 50 Listing Image for 1865 Kalia Way 37 of 50 Listing Image for 1865 Kalia Way 38 of 50 Listing Image for 1865 Kalia Way 39 of 50 Listing Image for 1865 Kalia Way 40 of 50 Listing Image for 1865 Kalia Way 41 of 50 Listing Image for 1865 Kalia Way 42 of 50 Listing Image for 1865 Kalia Way 43 of 50 Listing Image for 1865 Kalia Way 44 of 50 Listing Image for 1865 Kalia Way 45 of 50 Listing Image for 1865 Kalia Way 46 of 50 Listing Image for 1865 Kalia Way 47 of 50 Listing Image for 1865 Kalia Way 48 of 50 Listing Image for 1865 Kalia Way 49 of 50 Listing Image for 1865 Kalia Way 50 of 50

$2,550,000

↓ $245,000

Pauwela

1865 Kalia Way, Haiku

4 Beds 3 Baths 2,744 SqFt Residential MLS® # 406983 Date Sold: March 31, 2026
Sold
Closed: 06/03/2026
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$985,000

↓ $173,000

Maui Kamaole E-202

2777 S Kihei Rd E-202, Kihei

2 Beds 2 Baths 1,052 SqFt Residential MLS® # 406901 Date Sold: June 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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