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 2777 S Kihei Rd F209 1 of 47 Listing Image for 2777 S Kihei Rd F209 2 of 47 Listing Image for 2777 S Kihei Rd F209 3 of 47 Listing Image for 2777 S Kihei Rd F209 4 of 47 Listing Image for 2777 S Kihei Rd F209 5 of 47 Listing Image for 2777 S Kihei Rd F209 6 of 47 Listing Image for 2777 S Kihei Rd F209 7 of 47 Listing Image for 2777 S Kihei Rd F209 8 of 47 Listing Image for 2777 S Kihei Rd F209 9 of 47 Listing Image for 2777 S Kihei Rd F209 10 of 47 Listing Image for 2777 S Kihei Rd F209 11 of 47 Listing Image for 2777 S Kihei Rd F209 12 of 47 Listing Image for 2777 S Kihei Rd F209 13 of 47 Listing Image for 2777 S Kihei Rd F209 14 of 47 Listing Image for 2777 S Kihei Rd F209 15 of 47 Listing Image for 2777 S Kihei Rd F209 16 of 47 Listing Image for 2777 S Kihei Rd F209 17 of 47 Listing Image for 2777 S Kihei Rd F209 18 of 47 Listing Image for 2777 S Kihei Rd F209 19 of 47 Listing Image for 2777 S Kihei Rd F209 20 of 47 Listing Image for 2777 S Kihei Rd F209 21 of 47 Listing Image for 2777 S Kihei Rd F209 22 of 47 Listing Image for 2777 S Kihei Rd F209 23 of 47 Listing Image for 2777 S Kihei Rd F209 24 of 47 Listing Image for 2777 S Kihei Rd F209 25 of 47 Listing Image for 2777 S Kihei Rd F209 26 of 47 Listing Image for 2777 S Kihei Rd F209 27 of 47 Listing Image for 2777 S Kihei Rd F209 28 of 47 Listing Image for 2777 S Kihei Rd F209 29 of 47 Listing Image for 2777 S Kihei Rd F209 30 of 47 Listing Image for 2777 S Kihei Rd F209 31 of 47 Listing Image for 2777 S Kihei Rd F209 32 of 47 Listing Image for 2777 S Kihei Rd F209 33 of 47 Listing Image for 2777 S Kihei Rd F209 34 of 47 Listing Image for 2777 S Kihei Rd F209 35 of 47 Listing Image for 2777 S Kihei Rd F209 36 of 47 Listing Image for 2777 S Kihei Rd F209 37 of 47 Listing Image for 2777 S Kihei Rd F209 38 of 47 Listing Image for 2777 S Kihei Rd F209 39 of 47 Listing Image for 2777 S Kihei Rd F209 40 of 47 Listing Image for 2777 S Kihei Rd F209 41 of 47 Listing Image for 2777 S Kihei Rd F209 42 of 47 Listing Image for 2777 S Kihei Rd F209 43 of 47 Listing Image for 2777 S Kihei Rd F209 44 of 47 Listing Image for 2777 S Kihei Rd F209 45 of 47 Listing Image for 2777 S Kihei Rd F209 46 of 47 Listing Image for 2777 S Kihei Rd F209 47 of 47

$899,000

↓ $20,000

Maui Kamaole F209

2777 S Kihei Rd F209, Kihei

2 Beds 2 Baths 1,052 SqFt Residential MLS® # 409890

Days on Market: 101

eXp Realty Cell: 808-269-8633

Short Term Rental
Listing Image for 4299 Lower Honoapiilani Rd 275 1 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 2 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 3 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 4 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 5 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 6 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 7 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 8 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 9 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 10 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 11 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 12 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 13 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 14 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 15 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 16 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 17 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 18 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 19 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 20 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 21 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 22 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 23 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 24 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 25 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 26 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 27 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 28 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 29 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 30 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 31 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 32 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 33 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 34 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 35 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 36 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 37 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 38 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 39 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 40 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 41 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 42 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 43 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 44 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 45 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 46 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 47 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 48 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 49 of 50 Listing Image for 4299 Lower Honoapiilani Rd 275 50 of 50

$1,998,000

↓ $100,000

Sands of Kahana 275

4299 Lower Honoapiilani Rd 275, Napili/Kahana/Honokowai

3 Beds 2 Baths 1,730 SqFt Residential MLS® # 409881

Days on Market: 98

Coldwell Banker Island Prop-KP Cell: 808-344-2677

Short Term Rental
Listing Image for 500 Bay Dr 34b1-2 1 of 50 Listing Image for 500 Bay Dr 34b1-2 2 of 50 Listing Image for 500 Bay Dr 34b1-2 3 of 50 Listing Image for 500 Bay Dr 34b1-2 4 of 50 Listing Image for 500 Bay Dr 34b1-2 5 of 50 Listing Image for 500 Bay Dr 34b1-2 6 of 50 Listing Image for 500 Bay Dr 34b1-2 7 of 50 Listing Image for 500 Bay Dr 34b1-2 8 of 50 Listing Image for 500 Bay Dr 34b1-2 9 of 50 Listing Image for 500 Bay Dr 34b1-2 10 of 50 Listing Image for 500 Bay Dr 34b1-2 11 of 50 Listing Image for 500 Bay Dr 34b1-2 12 of 50 Listing Image for 500 Bay Dr 34b1-2 13 of 50 Listing Image for 500 Bay Dr 34b1-2 14 of 50 Listing Image for 500 Bay Dr 34b1-2 15 of 50 Listing Image for 500 Bay Dr 34b1-2 16 of 50 Listing Image for 500 Bay Dr 34b1-2 17 of 50 Listing Image for 500 Bay Dr 34b1-2 18 of 50 Listing Image for 500 Bay Dr 34b1-2 19 of 50 Listing Image for 500 Bay Dr 34b1-2 20 of 50 Listing Image for 500 Bay Dr 34b1-2 21 of 50 Listing Image for 500 Bay Dr 34b1-2 22 of 50 Listing Image for 500 Bay Dr 34b1-2 23 of 50 Listing Image for 500 Bay Dr 34b1-2 24 of 50 Listing Image for 500 Bay Dr 34b1-2 25 of 50 Listing Image for 500 Bay Dr 34b1-2 26 of 50 Listing Image for 500 Bay Dr 34b1-2 27 of 50 Listing Image for 500 Bay Dr 34b1-2 28 of 50 Listing Image for 500 Bay Dr 34b1-2 29 of 50 Listing Image for 500 Bay Dr 34b1-2 30 of 50 Listing Image for 500 Bay Dr 34b1-2 31 of 50 Listing Image for 500 Bay Dr 34b1-2 32 of 50 Listing Image for 500 Bay Dr 34b1-2 33 of 50 Listing Image for 500 Bay Dr 34b1-2 34 of 50 Listing Image for 500 Bay Dr 34b1-2 35 of 50 Listing Image for 500 Bay Dr 34b1-2 36 of 50 Listing Image for 500 Bay Dr 34b1-2 37 of 50 Listing Image for 500 Bay Dr 34b1-2 38 of 50 Listing Image for 500 Bay Dr 34b1-2 39 of 50 Listing Image for 500 Bay Dr 34b1-2 40 of 50 Listing Image for 500 Bay Dr 34b1-2 41 of 50 Listing Image for 500 Bay Dr 34b1-2 42 of 50 Listing Image for 500 Bay Dr 34b1-2 43 of 50 Listing Image for 500 Bay Dr 34b1-2 44 of 50 Listing Image for 500 Bay Dr 34b1-2 45 of 50 Listing Image for 500 Bay Dr 34b1-2 46 of 50 Listing Image for 500 Bay Dr 34b1-2 47 of 50 Listing Image for 500 Bay Dr 34b1-2 48 of 50 Listing Image for 500 Bay Dr 34b1-2 49 of 50 Listing Image for 500 Bay Dr 34b1-2 50 of 50

$3,298,000

Kapalua Bay Villas 34B1-2

500 Bay Dr 34b1-2, Kapalua

2 Beds 3 Baths 1,697 SqFt Residential MLS® # 409879

Days on Market: 98

Coldwell Banker Island Prop-KP Cell: 808-344-2677

Short Term Rental
Listing Image for 500 Bay Dr 11b2 1 of 50 Listing Image for 500 Bay Dr 11b2 2 of 50 Listing Image for 500 Bay Dr 11b2 3 of 50 Listing Image for 500 Bay Dr 11b2 4 of 50 Listing Image for 500 Bay Dr 11b2 5 of 50 Listing Image for 500 Bay Dr 11b2 6 of 50 Listing Image for 500 Bay Dr 11b2 7 of 50 Listing Image for 500 Bay Dr 11b2 8 of 50 Listing Image for 500 Bay Dr 11b2 9 of 50 Listing Image for 500 Bay Dr 11b2 10 of 50 Listing Image for 500 Bay Dr 11b2 11 of 50 Listing Image for 500 Bay Dr 11b2 12 of 50 Listing Image for 500 Bay Dr 11b2 13 of 50 Listing Image for 500 Bay Dr 11b2 14 of 50 Listing Image for 500 Bay Dr 11b2 15 of 50 Listing Image for 500 Bay Dr 11b2 16 of 50 Listing Image for 500 Bay Dr 11b2 17 of 50 Listing Image for 500 Bay Dr 11b2 18 of 50 Listing Image for 500 Bay Dr 11b2 19 of 50 Listing Image for 500 Bay Dr 11b2 20 of 50 Listing Image for 500 Bay Dr 11b2 21 of 50 Listing Image for 500 Bay Dr 11b2 22 of 50 Listing Image for 500 Bay Dr 11b2 23 of 50 Listing Image for 500 Bay Dr 11b2 24 of 50 Listing Image for 500 Bay Dr 11b2 25 of 50 Listing Image for 500 Bay Dr 11b2 26 of 50 Listing Image for 500 Bay Dr 11b2 27 of 50 Listing Image for 500 Bay Dr 11b2 28 of 50 Listing Image for 500 Bay Dr 11b2 29 of 50 Listing Image for 500 Bay Dr 11b2 30 of 50 Listing Image for 500 Bay Dr 11b2 31 of 50 Listing Image for 500 Bay Dr 11b2 32 of 50 Listing Image for 500 Bay Dr 11b2 33 of 50 Listing Image for 500 Bay Dr 11b2 34 of 50 Listing Image for 500 Bay Dr 11b2 35 of 50 Listing Image for 500 Bay Dr 11b2 36 of 50 Listing Image for 500 Bay Dr 11b2 37 of 50 Listing Image for 500 Bay Dr 11b2 38 of 50 Listing Image for 500 Bay Dr 11b2 39 of 50 Listing Image for 500 Bay Dr 11b2 40 of 50 Listing Image for 500 Bay Dr 11b2 41 of 50 Listing Image for 500 Bay Dr 11b2 42 of 50 Listing Image for 500 Bay Dr 11b2 43 of 50 Listing Image for 500 Bay Dr 11b2 44 of 50 Listing Image for 500 Bay Dr 11b2 45 of 50 Listing Image for 500 Bay Dr 11b2 46 of 50 Listing Image for 500 Bay Dr 11b2 47 of 50 Listing Image for 500 Bay Dr 11b2 48 of 50 Listing Image for 500 Bay Dr 11b2 49 of 50 Listing Image for 500 Bay Dr 11b2 50 of 50

$2,298,000

↓ $100,000

Kapalua Bay Villas 11B2

500 Bay Dr 11b2, Kapalua

2 Beds 3 Baths 1,503 SqFt Residential MLS® # 409878

Days on Market: 98

Coldwell Banker Island Prop-KP Cell: 808-344-2677

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

$6,398,000

Kapalua Ironwoods 22

22 Ironwood Ln 22, Kapalua

2 Beds 3 Baths 1,935 SqFt Residential MLS® # 409875

Days on Market: 98

Coldwell Banker Island Prop-KP Cell: 808-344-2677

Short Term Rental
Listing Image for 110 Kaanapali Shores Pl 1019 1 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 2 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 3 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 4 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 5 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 6 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 7 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 8 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 9 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 10 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 11 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 12 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 13 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 14 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 15 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 16 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 17 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 18 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 19 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 20 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 21 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 22 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 23 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 24 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 25 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 26 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 27 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 28 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 29 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 30 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 31 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 32 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 33 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 34 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 35 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 36 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 37 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 38 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 39 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 40 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 41 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 42 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 43 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 44 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 45 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 46 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 47 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 48 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 49 of 50 Listing Image for 110 Kaanapali Shores Pl 1019 50 of 50

$2,699,000

Mahana 1019

110 Kaanapali Shores Pl 1019, Kaanapali

2 Beds 2 Baths 1,214 SqFt Residential MLS® # 409874

Days on Market: 98

Coldwell Banker Island Prop-KP Cell: 808-344-2677

Listing Image for 2450 Piiholo Rd 1 of 39 Listing Image for 2450 Piiholo Rd 2 of 39 Listing Image for 2450 Piiholo Rd 3 of 39 Listing Image for 2450 Piiholo Rd 4 of 39 Listing Image for 2450 Piiholo Rd 5 of 39 Listing Image for 2450 Piiholo Rd 6 of 39 Listing Image for 2450 Piiholo Rd 7 of 39 Listing Image for 2450 Piiholo Rd 8 of 39 Listing Image for 2450 Piiholo Rd 9 of 39 Listing Image for 2450 Piiholo Rd 10 of 39 Listing Image for 2450 Piiholo Rd 11 of 39 Listing Image for 2450 Piiholo Rd 12 of 39 Listing Image for 2450 Piiholo Rd 13 of 39 Listing Image for 2450 Piiholo Rd 14 of 39 Listing Image for 2450 Piiholo Rd 15 of 39 Listing Image for 2450 Piiholo Rd 16 of 39 Listing Image for 2450 Piiholo Rd 17 of 39 Listing Image for 2450 Piiholo Rd 18 of 39 Listing Image for 2450 Piiholo Rd 19 of 39 Listing Image for 2450 Piiholo Rd 20 of 39 Listing Image for 2450 Piiholo Rd 21 of 39 Listing Image for 2450 Piiholo Rd 22 of 39 Listing Image for 2450 Piiholo Rd 23 of 39 Listing Image for 2450 Piiholo Rd 24 of 39 Listing Image for 2450 Piiholo Rd 25 of 39 Listing Image for 2450 Piiholo Rd 26 of 39 Listing Image for 2450 Piiholo Rd 27 of 39 Listing Image for 2450 Piiholo Rd 28 of 39 Listing Image for 2450 Piiholo Rd 29 of 39 Listing Image for 2450 Piiholo Rd 30 of 39 Listing Image for 2450 Piiholo Rd 31 of 39 Listing Image for 2450 Piiholo Rd 32 of 39 Listing Image for 2450 Piiholo Rd 33 of 39 Listing Image for 2450 Piiholo Rd 34 of 39 Listing Image for 2450 Piiholo Rd 35 of 39 Listing Image for 2450 Piiholo Rd 36 of 39 Listing Image for 2450 Piiholo Rd 37 of 39 Listing Image for 2450 Piiholo Rd 38 of 39 Listing Image for 2450 Piiholo Rd 39 of 39

$4,750,000

Makawao/Olinda/Haliimaile

2450 Piiholo Rd, Makawao/Olinda/Haliimaile

3 Beds 3.5 Baths 3,229 SqFt Residential MLS® # 409873

Days on Market: 98

Coldwell Banker Island Prop(P) Cell: 808-264-3112

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Apply for a Home Equity Loan

While you may ideally want to sell your current house before buying a new one, this may not be an absolute requirement for some sellers. You could tap into your home’s equity by applying for an equity line of credit. Before moving forward with this possibility, be aware that the payment on the new home equity line will affect your debt-to-income ratio.

Mortgage lenders review your debt-to-income ratio as part of their qualification process. Because of this, you should discuss this option in detail with your lender to ensure that it will not impair your ability to qualify for a new mortgage.

Recent Sales on Maui

Sold
Closed: 03/16/2026
Listing Image for 4299 Lower Honoapiilani Rd 243 1 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 2 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 3 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 4 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 5 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 6 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 7 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 8 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 9 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 10 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 11 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 12 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 13 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 14 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 15 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 16 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 17 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 18 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 19 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 20 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 21 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 22 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 23 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 24 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 25 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 26 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 27 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 28 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 29 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 30 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 31 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 32 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 33 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 34 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 35 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 36 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 37 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 38 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 39 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 40 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 41 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 42 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 43 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 44 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 45 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 46 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 47 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 48 of 49 Listing Image for 4299 Lower Honoapiilani Rd 243 49 of 49

$1,985,000

Sands of Kahana 243

4299 Lower Honoapiilani Rd 243, Napili/Kahana/Honokowai

2 Beds 2 Baths 1,660 SqFt Residential MLS® # 408609 Date Sold: March 16, 2026
Sold
Closed: 06/12/2026
Listing Image for 145 N Kihei Rd 232 1 of 24 Listing Image for 145 N Kihei Rd 232 2 of 24 Listing Image for 145 N Kihei Rd 232 3 of 24 Listing Image for 145 N Kihei Rd 232 4 of 24 Listing Image for 145 N Kihei Rd 232 5 of 24 Listing Image for 145 N Kihei Rd 232 6 of 24 Listing Image for 145 N Kihei Rd 232 7 of 24 Listing Image for 145 N Kihei Rd 232 8 of 24 Listing Image for 145 N Kihei Rd 232 9 of 24 Listing Image for 145 N Kihei Rd 232 10 of 24 Listing Image for 145 N Kihei Rd 232 11 of 24 Listing Image for 145 N Kihei Rd 232 12 of 24 Listing Image for 145 N Kihei Rd 232 13 of 24 Listing Image for 145 N Kihei Rd 232 14 of 24 Listing Image for 145 N Kihei Rd 232 15 of 24 Listing Image for 145 N Kihei Rd 232 16 of 24 Listing Image for 145 N Kihei Rd 232 17 of 24 Listing Image for 145 N Kihei Rd 232 18 of 24 Listing Image for 145 N Kihei Rd 232 19 of 24 Listing Image for 145 N Kihei Rd 232 20 of 24 Listing Image for 145 N Kihei Rd 232 21 of 24 Listing Image for 145 N Kihei Rd 232 22 of 24 Listing Image for 145 N Kihei Rd 232 23 of 24 Listing Image for 145 N Kihei Rd 232 24 of 24

$755,000

↓ $213,000

Sugar Beach Resort 232

145 N Kihei Rd 232, Kihei

1 Bed 1 Bath 613 SqFt Residential MLS® # 408606 Date Sold: June 12, 2026
Sold
Closed: 03/18/2026
Listing Image for 49 Hiwalani Loop 1 of 49 Listing Image for 49 Hiwalani Loop 2 of 49 Listing Image for 49 Hiwalani Loop 3 of 49 Listing Image for 49 Hiwalani Loop 4 of 49 Listing Image for 49 Hiwalani Loop 5 of 49 Listing Image for 49 Hiwalani Loop 6 of 49 Listing Image for 49 Hiwalani Loop 7 of 49 Listing Image for 49 Hiwalani Loop 8 of 49 Listing Image for 49 Hiwalani Loop 9 of 49 Listing Image for 49 Hiwalani Loop 10 of 49 Listing Image for 49 Hiwalani Loop 11 of 49 Listing Image for 49 Hiwalani Loop 12 of 49 Listing Image for 49 Hiwalani Loop 13 of 49 Listing Image for 49 Hiwalani Loop 14 of 49 Listing Image for 49 Hiwalani Loop 15 of 49 Listing Image for 49 Hiwalani Loop 16 of 49 Listing Image for 49 Hiwalani Loop 17 of 49 Listing Image for 49 Hiwalani Loop 18 of 49 Listing Image for 49 Hiwalani Loop 19 of 49 Listing Image for 49 Hiwalani Loop 20 of 49 Listing Image for 49 Hiwalani Loop 21 of 49 Listing Image for 49 Hiwalani Loop 22 of 49 Listing Image for 49 Hiwalani Loop 23 of 49 Listing Image for 49 Hiwalani Loop 24 of 49 Listing Image for 49 Hiwalani Loop 25 of 49 Listing Image for 49 Hiwalani Loop 26 of 49 Listing Image for 49 Hiwalani Loop 27 of 49 Listing Image for 49 Hiwalani Loop 28 of 49 Listing Image for 49 Hiwalani Loop 29 of 49 Listing Image for 49 Hiwalani Loop 30 of 49 Listing Image for 49 Hiwalani Loop 31 of 49 Listing Image for 49 Hiwalani Loop 32 of 49 Listing Image for 49 Hiwalani Loop 33 of 49 Listing Image for 49 Hiwalani Loop 34 of 49 Listing Image for 49 Hiwalani Loop 35 of 49 Listing Image for 49 Hiwalani Loop 36 of 49 Listing Image for 49 Hiwalani Loop 37 of 49 Listing Image for 49 Hiwalani Loop 38 of 49 Listing Image for 49 Hiwalani Loop 39 of 49 Listing Image for 49 Hiwalani Loop 40 of 49 Listing Image for 49 Hiwalani Loop 41 of 49 Listing Image for 49 Hiwalani Loop 42 of 49 Listing Image for 49 Hiwalani Loop 43 of 49 Listing Image for 49 Hiwalani Loop 44 of 49 Listing Image for 49 Hiwalani Loop 45 of 49 Listing Image for 49 Hiwalani Loop 46 of 49 Listing Image for 49 Hiwalani Loop 47 of 49 Listing Image for 49 Hiwalani Loop 48 of 49 Listing Image for 49 Hiwalani Loop 49 of 49

$1,249,000

Pukalani

49 Hiwalani Loop, Pukalani

3 Beds 2.5 Baths 1,754 SqFt Residential MLS® # 408605 Date Sold: March 18, 2026
Sold
Closed: 01/30/2026
118 Maiaku St 153, Makawao/Olinda/Haliimaile

$1,395,000

Hokuula

118 Maiaku St 153, Makawao/Olinda/Haliimaile

4 Beds 3 Baths 1,960 SqFt Residential MLS® # 408603 Date Sold: January 30, 2026
Sold
Closed: 03/30/2026
Listing Image for 25 Hoihoi Pl A 1 of 27 Listing Image for 25 Hoihoi Pl A 2 of 27 Listing Image for 25 Hoihoi Pl A 3 of 27 Listing Image for 25 Hoihoi Pl A 4 of 27 Listing Image for 25 Hoihoi Pl A 5 of 27 Listing Image for 25 Hoihoi Pl A 6 of 27 Listing Image for 25 Hoihoi Pl A 7 of 27 Listing Image for 25 Hoihoi Pl A 8 of 27 Listing Image for 25 Hoihoi Pl A 9 of 27 Listing Image for 25 Hoihoi Pl A 10 of 27 Listing Image for 25 Hoihoi Pl A 11 of 27 Listing Image for 25 Hoihoi Pl A 12 of 27 Listing Image for 25 Hoihoi Pl A 13 of 27 Listing Image for 25 Hoihoi Pl A 14 of 27 Listing Image for 25 Hoihoi Pl A 15 of 27 Listing Image for 25 Hoihoi Pl A 16 of 27 Listing Image for 25 Hoihoi Pl A 17 of 27 Listing Image for 25 Hoihoi Pl A 18 of 27 Listing Image for 25 Hoihoi Pl A 19 of 27 Listing Image for 25 Hoihoi Pl A 20 of 27 Listing Image for 25 Hoihoi Pl A 21 of 27 Listing Image for 25 Hoihoi Pl A 22 of 27 Listing Image for 25 Hoihoi Pl A 23 of 27 Listing Image for 25 Hoihoi Pl A 24 of 27 Listing Image for 25 Hoihoi Pl A 25 of 27 Listing Image for 25 Hoihoi Pl A 26 of 27 Listing Image for 25 Hoihoi Pl A 27 of 27

$895,000

Kula/Ulupalakua/Kanaio

25 Hoihoi Pl A, Kula/Ulupalakua/Kanaio

1 Bed 1 Bath 864 SqFt Residential MLS® # 408601 Date Sold: March 30, 2026
Sold
Closed: 04/06/2026
Listing Image for 208 Molokai Hema St 1 of 41 Listing Image for 208 Molokai Hema St 2 of 41 Listing Image for 208 Molokai Hema St 3 of 41 Listing Image for 208 Molokai Hema St 4 of 41 Listing Image for 208 Molokai Hema St 5 of 41 Listing Image for 208 Molokai Hema St 6 of 41 Listing Image for 208 Molokai Hema St 7 of 41 Listing Image for 208 Molokai Hema St 8 of 41 Listing Image for 208 Molokai Hema St 9 of 41 Listing Image for 208 Molokai Hema St 10 of 41 Listing Image for 208 Molokai Hema St 11 of 41 Listing Image for 208 Molokai Hema St 12 of 41 Listing Image for 208 Molokai Hema St 13 of 41 Listing Image for 208 Molokai Hema St 14 of 41 Listing Image for 208 Molokai Hema St 15 of 41 Listing Image for 208 Molokai Hema St 16 of 41 Listing Image for 208 Molokai Hema St 17 of 41 Listing Image for 208 Molokai Hema St 18 of 41 Listing Image for 208 Molokai Hema St 19 of 41 Listing Image for 208 Molokai Hema St 20 of 41 Listing Image for 208 Molokai Hema St 21 of 41 Listing Image for 208 Molokai Hema St 22 of 41 Listing Image for 208 Molokai Hema St 23 of 41 Listing Image for 208 Molokai Hema St 24 of 41 Listing Image for 208 Molokai Hema St 25 of 41 Listing Image for 208 Molokai Hema St 26 of 41 Listing Image for 208 Molokai Hema St 27 of 41 Listing Image for 208 Molokai Hema St 28 of 41 Listing Image for 208 Molokai Hema St 29 of 41 Listing Image for 208 Molokai Hema St 30 of 41 Listing Image for 208 Molokai Hema St 31 of 41 Listing Image for 208 Molokai Hema St 32 of 41 Listing Image for 208 Molokai Hema St 33 of 41 Listing Image for 208 Molokai Hema St 34 of 41 Listing Image for 208 Molokai Hema St 35 of 41 Listing Image for 208 Molokai Hema St 36 of 41 Listing Image for 208 Molokai Hema St 37 of 41 Listing Image for 208 Molokai Hema St 38 of 41 Listing Image for 208 Molokai Hema St 39 of 41 Listing Image for 208 Molokai Hema St 40 of 41 Listing Image for 208 Molokai Hema St 41 of 41

$1,174,500

Kahului Town Development

208 Molokai Hema St, Kahului

3 Beds 1 Bath 877 SqFt Residential MLS® # 408597 Date Sold: April 6, 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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