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

$11,998,000

The Ridge at Wailea

14 Halapa Pl, Wailea/Makena

4 Beds 4.5 Baths 5,126 SqFt Residential MLS® # 406282

Days on Market: 456

Hawaii Life (W) Cell: 808-276-2004

Listing Image for 101 Unahe Pl Lot 127-b 1 of 18 Listing Image for 101 Unahe Pl Lot 127-b 2 of 18 Listing Image for 101 Unahe Pl Lot 127-b 3 of 18 Listing Image for 101 Unahe Pl Lot 127-b 4 of 18 Listing Image for 101 Unahe Pl Lot 127-b 5 of 18 Listing Image for 101 Unahe Pl Lot 127-b 6 of 18 Listing Image for 101 Unahe Pl Lot 127-b 7 of 18 Listing Image for 101 Unahe Pl Lot 127-b 8 of 18 Listing Image for 101 Unahe Pl Lot 127-b 9 of 18 Listing Image for 101 Unahe Pl Lot 127-b 10 of 18 Listing Image for 101 Unahe Pl Lot 127-b 11 of 18 Listing Image for 101 Unahe Pl Lot 127-b 12 of 18 Listing Image for 101 Unahe Pl Lot 127-b 13 of 18 Listing Image for 101 Unahe Pl Lot 127-b 14 of 18 Listing Image for 101 Unahe Pl Lot 127-b 15 of 18 Listing Image for 101 Unahe Pl Lot 127-b 16 of 18 Listing Image for 101 Unahe Pl Lot 127-b 17 of 18 Listing Image for 101 Unahe Pl Lot 127-b 18 of 18

$1,239,910

↓ $53,000

The Parkways at Maui Lani

101 Unahe Pl Lot 127-b, Kahului

3 Beds 2 Baths 1,596 SqFt Residential MLS® # 406015

Days on Market: 485

Towne Island Homes, Ltd

Listing Image for 3788 Lower Honoapiilani Rd D101 1 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 2 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 3 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 4 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 5 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 6 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 7 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 8 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 9 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 10 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 11 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 12 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 13 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 14 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 15 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 16 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 17 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 18 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 19 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 20 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 21 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 22 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 23 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 24 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 25 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 26 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 27 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 28 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 29 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 30 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 31 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 32 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 33 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 34 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 35 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 36 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 37 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 38 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 39 of 40 Listing Image for 3788 Lower Honoapiilani Rd D101 40 of 40

$875,000

↓ $20,000

Hale Royale D101

3788 Lower Honoapiilani Rd D101, Napili/Kahana/Honokowai

2 Beds 2 Baths 1,122 SqFt Residential MLS® # 406252

Days on Market: 458

Coldwell Banker Island Prop-KP Cell: 808-357-4000

Short Term Rental
Listing Image for 50 Nohea Kai Dr 2-702 1 of 44 Listing Image for 50 Nohea Kai Dr 2-702 2 of 44 Listing Image for 50 Nohea Kai Dr 2-702 3 of 44 Listing Image for 50 Nohea Kai Dr 2-702 4 of 44 Listing Image for 50 Nohea Kai Dr 2-702 5 of 44 Listing Image for 50 Nohea Kai Dr 2-702 6 of 44 Listing Image for 50 Nohea Kai Dr 2-702 7 of 44 Listing Image for 50 Nohea Kai Dr 2-702 8 of 44 Listing Image for 50 Nohea Kai Dr 2-702 9 of 44 Listing Image for 50 Nohea Kai Dr 2-702 10 of 44 Listing Image for 50 Nohea Kai Dr 2-702 11 of 44 Listing Image for 50 Nohea Kai Dr 2-702 12 of 44 Listing Image for 50 Nohea Kai Dr 2-702 13 of 44 Listing Image for 50 Nohea Kai Dr 2-702 14 of 44 Listing Image for 50 Nohea Kai Dr 2-702 15 of 44 Listing Image for 50 Nohea Kai Dr 2-702 16 of 44 Listing Image for 50 Nohea Kai Dr 2-702 17 of 44 Listing Image for 50 Nohea Kai Dr 2-702 18 of 44 Listing Image for 50 Nohea Kai Dr 2-702 19 of 44 Listing Image for 50 Nohea Kai Dr 2-702 20 of 44 Listing Image for 50 Nohea Kai Dr 2-702 21 of 44 Listing Image for 50 Nohea Kai Dr 2-702 22 of 44 Listing Image for 50 Nohea Kai Dr 2-702 23 of 44 Listing Image for 50 Nohea Kai Dr 2-702 24 of 44 Listing Image for 50 Nohea Kai Dr 2-702 25 of 44 Listing Image for 50 Nohea Kai Dr 2-702 26 of 44 Listing Image for 50 Nohea Kai Dr 2-702 27 of 44 Listing Image for 50 Nohea Kai Dr 2-702 28 of 44 Listing Image for 50 Nohea Kai Dr 2-702 29 of 44 Listing Image for 50 Nohea Kai Dr 2-702 30 of 44 Listing Image for 50 Nohea Kai Dr 2-702 31 of 44 Listing Image for 50 Nohea Kai Dr 2-702 32 of 44 Listing Image for 50 Nohea Kai Dr 2-702 33 of 44 Listing Image for 50 Nohea Kai Dr 2-702 34 of 44 Listing Image for 50 Nohea Kai Dr 2-702 35 of 44 Listing Image for 50 Nohea Kai Dr 2-702 36 of 44 Listing Image for 50 Nohea Kai Dr 2-702 37 of 44 Listing Image for 50 Nohea Kai Dr 2-702 38 of 44 Listing Image for 50 Nohea Kai Dr 2-702 39 of 44 Listing Image for 50 Nohea Kai Dr 2-702 40 of 44 Listing Image for 50 Nohea Kai Dr 2-702 41 of 44 Listing Image for 50 Nohea Kai Dr 2-702 42 of 44 Listing Image for 50 Nohea Kai Dr 2-702 43 of 44 Listing Image for 50 Nohea Kai Dr 2-702 44 of 44

$2,195,000

↓ $200,000

Kaanapali Alii 2-702

50 Nohea Kai Dr 2-702, Kaanapali

1 Bed 2 Baths 1,441 SqFt Residential MLS® # 406233

Days on Market: 462

Sullivan Properties Inc

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 210 Napoko Pl 1 of 37 Listing Image for 210 Napoko Pl 2 of 37 Listing Image for 210 Napoko Pl 3 of 37 Listing Image for 210 Napoko Pl 4 of 37 Listing Image for 210 Napoko Pl 5 of 37 Listing Image for 210 Napoko Pl 6 of 37 Listing Image for 210 Napoko Pl 7 of 37 Listing Image for 210 Napoko Pl 8 of 37 Listing Image for 210 Napoko Pl 9 of 37 Listing Image for 210 Napoko Pl 10 of 37 Listing Image for 210 Napoko Pl 11 of 37 Listing Image for 210 Napoko Pl 12 of 37 Listing Image for 210 Napoko Pl 13 of 37 Listing Image for 210 Napoko Pl 14 of 37 Listing Image for 210 Napoko Pl 15 of 37 Listing Image for 210 Napoko Pl 16 of 37 Listing Image for 210 Napoko Pl 17 of 37 Listing Image for 210 Napoko Pl 18 of 37 Listing Image for 210 Napoko Pl 19 of 37 Listing Image for 210 Napoko Pl 20 of 37 Listing Image for 210 Napoko Pl 21 of 37 Listing Image for 210 Napoko Pl 22 of 37 Listing Image for 210 Napoko Pl 23 of 37 Listing Image for 210 Napoko Pl 24 of 37 Listing Image for 210 Napoko Pl 25 of 37 Listing Image for 210 Napoko Pl 26 of 37 Listing Image for 210 Napoko Pl 27 of 37 Listing Image for 210 Napoko Pl 28 of 37 Listing Image for 210 Napoko Pl 29 of 37 Listing Image for 210 Napoko Pl 30 of 37 Listing Image for 210 Napoko Pl 31 of 37 Listing Image for 210 Napoko Pl 32 of 37 Listing Image for 210 Napoko Pl 33 of 37 Listing Image for 210 Napoko Pl 34 of 37 Listing Image for 210 Napoko Pl 35 of 37 Listing Image for 210 Napoko Pl 36 of 37 Listing Image for 210 Napoko Pl 37 of 37

$4,000,000

Kula/Ulupalakua/Kanaio

210 Napoko Pl, Kula/Ulupalakua/Kanaio

3 Beds 2 Baths 1,200 SqFt Residential MLS® # 404282

Days on Market: 647

Hawaii Equity Management LLC

Short Term Rental
Listing Image for 130 Kai Malina Pkwy Sr325 1 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 2 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 3 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 4 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 5 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 6 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 7 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 8 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 9 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 10 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 11 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 12 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 13 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 14 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 15 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 16 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 17 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 18 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 19 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 20 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 21 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 22 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 23 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 24 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 25 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 26 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 27 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 28 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 29 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 30 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 31 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 32 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 33 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 34 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 35 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 36 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 37 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 38 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 39 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 40 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 41 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 42 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 43 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 44 of 45 Listing Image for 130 Kai Malina Pkwy Sr325 45 of 45

$4,200,000

Honua Kai - Hoku Lani SR325

130 Kai Malina Pkwy Sr325, Kaanapali

3 Beds 3 Baths 1,600 SqFt Residential MLS® # 403317

Days on Market: 749

Island Sotheby's International Realty(W) Cell: 808-385-6564

Listing Image for 34701 Piilani Hwy 1 of 37 Listing Image for 34701 Piilani Hwy 2 of 37 Listing Image for 34701 Piilani Hwy 3 of 37 Listing Image for 34701 Piilani Hwy 4 of 37 Listing Image for 34701 Piilani Hwy 5 of 37 Listing Image for 34701 Piilani Hwy 6 of 37 Listing Image for 34701 Piilani Hwy 7 of 37 Listing Image for 34701 Piilani Hwy 8 of 37 Listing Image for 34701 Piilani Hwy 9 of 37 Listing Image for 34701 Piilani Hwy 10 of 37 Listing Image for 34701 Piilani Hwy 11 of 37 Listing Image for 34701 Piilani Hwy 12 of 37 Listing Image for 34701 Piilani Hwy 13 of 37 Listing Image for 34701 Piilani Hwy 14 of 37 Listing Image for 34701 Piilani Hwy 15 of 37 Listing Image for 34701 Piilani Hwy 16 of 37 Listing Image for 34701 Piilani Hwy 17 of 37 Listing Image for 34701 Piilani Hwy 18 of 37 Listing Image for 34701 Piilani Hwy 19 of 37 Listing Image for 34701 Piilani Hwy 20 of 37 Listing Image for 34701 Piilani Hwy 21 of 37 Listing Image for 34701 Piilani Hwy 22 of 37 Listing Image for 34701 Piilani Hwy 23 of 37 Listing Image for 34701 Piilani Hwy 24 of 37 Listing Image for 34701 Piilani Hwy 25 of 37 Listing Image for 34701 Piilani Hwy 26 of 37 Listing Image for 34701 Piilani Hwy 27 of 37 Listing Image for 34701 Piilani Hwy 28 of 37 Listing Image for 34701 Piilani Hwy 29 of 37 Listing Image for 34701 Piilani Hwy 30 of 37 Listing Image for 34701 Piilani Hwy 31 of 37 Listing Image for 34701 Piilani Hwy 32 of 37 Listing Image for 34701 Piilani Hwy 33 of 37 Listing Image for 34701 Piilani Hwy 34 of 37 Listing Image for 34701 Piilani Hwy 35 of 37 Listing Image for 34701 Piilani Hwy 36 of 37 Listing Image for 34701 Piilani Hwy 37 of 37

$995,000

↓ $200,000

Kaupo

34701 Piilani Hwy, Kaupo

1 Bed 1 Bath 1,000 SqFt Residential MLS® # 405926

Days on Market: 495

Keller Williams Realty Maui-Ka Cell: 808-268-0499

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: 08/22/2025
100 Kuula St, Kahului

$1,200,000

Kahului

100 Kuula St, Kahului

9 Beds 4 Baths 3,529 SqFt Residential MLS® # 406919 Date Sold: August 22, 2025
Sold
Closed: 12/01/2025
Listing Image for 50 Puu Anoano St 706 1 of 39 Listing Image for 50 Puu Anoano St 706 2 of 39 Listing Image for 50 Puu Anoano St 706 3 of 39 Listing Image for 50 Puu Anoano St 706 4 of 39 Listing Image for 50 Puu Anoano St 706 5 of 39 Listing Image for 50 Puu Anoano St 706 6 of 39 Listing Image for 50 Puu Anoano St 706 7 of 39 Listing Image for 50 Puu Anoano St 706 8 of 39 Listing Image for 50 Puu Anoano St 706 9 of 39 Listing Image for 50 Puu Anoano St 706 10 of 39 Listing Image for 50 Puu Anoano St 706 11 of 39 Listing Image for 50 Puu Anoano St 706 12 of 39 Listing Image for 50 Puu Anoano St 706 13 of 39 Listing Image for 50 Puu Anoano St 706 14 of 39 Listing Image for 50 Puu Anoano St 706 15 of 39 Listing Image for 50 Puu Anoano St 706 16 of 39 Listing Image for 50 Puu Anoano St 706 17 of 39 Listing Image for 50 Puu Anoano St 706 18 of 39 Listing Image for 50 Puu Anoano St 706 19 of 39 Listing Image for 50 Puu Anoano St 706 20 of 39 Listing Image for 50 Puu Anoano St 706 21 of 39 Listing Image for 50 Puu Anoano St 706 22 of 39 Listing Image for 50 Puu Anoano St 706 23 of 39 Listing Image for 50 Puu Anoano St 706 24 of 39 Listing Image for 50 Puu Anoano St 706 25 of 39 Listing Image for 50 Puu Anoano St 706 26 of 39 Listing Image for 50 Puu Anoano St 706 27 of 39 Listing Image for 50 Puu Anoano St 706 28 of 39 Listing Image for 50 Puu Anoano St 706 29 of 39 Listing Image for 50 Puu Anoano St 706 30 of 39 Listing Image for 50 Puu Anoano St 706 31 of 39 Listing Image for 50 Puu Anoano St 706 32 of 39 Listing Image for 50 Puu Anoano St 706 33 of 39 Listing Image for 50 Puu Anoano St 706 34 of 39 Listing Image for 50 Puu Anoano St 706 35 of 39 Listing Image for 50 Puu Anoano St 706 36 of 39 Listing Image for 50 Puu Anoano St 706 37 of 39 Listing Image for 50 Puu Anoano St 706 38 of 39 Listing Image for 50 Puu Anoano St 706 39 of 39

$1,200,000

↓ $335,000

Masters 706

50 Puu Anoano St 706, Kaanapali

2 Beds 2 Baths 1,512 SqFt Residential MLS® # 406927 Date Sold: December 1, 2025
Sold
Closed: 08/22/2025
130 Oliona St 126, Makawao/Olinda/Haliimaile

$1,515,000

Hokuula

130 Oliona St 126, Makawao/Olinda/Haliimaile

4 Beds 3 Baths 1,960 SqFt Residential MLS® # 406915 Date Sold: August 22, 2025
Sold
Closed: 12/17/2025
Listing Image for 909 Copp Rd 1 of 48 Listing Image for 909 Copp Rd 2 of 48 Listing Image for 909 Copp Rd 3 of 48 Listing Image for 909 Copp Rd 4 of 48 Listing Image for 909 Copp Rd 5 of 48 Listing Image for 909 Copp Rd 6 of 48 Listing Image for 909 Copp Rd 7 of 48 Listing Image for 909 Copp Rd 8 of 48 Listing Image for 909 Copp Rd 9 of 48 Listing Image for 909 Copp Rd 10 of 48 Listing Image for 909 Copp Rd 11 of 48 Listing Image for 909 Copp Rd 12 of 48 Listing Image for 909 Copp Rd 13 of 48 Listing Image for 909 Copp Rd 14 of 48 Listing Image for 909 Copp Rd 15 of 48 Listing Image for 909 Copp Rd 16 of 48 Listing Image for 909 Copp Rd 17 of 48 Listing Image for 909 Copp Rd 18 of 48 Listing Image for 909 Copp Rd 19 of 48 Listing Image for 909 Copp Rd 20 of 48 Listing Image for 909 Copp Rd 21 of 48 Listing Image for 909 Copp Rd 22 of 48 Listing Image for 909 Copp Rd 23 of 48 Listing Image for 909 Copp Rd 24 of 48 Listing Image for 909 Copp Rd 25 of 48 Listing Image for 909 Copp Rd 26 of 48 Listing Image for 909 Copp Rd 27 of 48 Listing Image for 909 Copp Rd 28 of 48 Listing Image for 909 Copp Rd 29 of 48 Listing Image for 909 Copp Rd 30 of 48 Listing Image for 909 Copp Rd 31 of 48 Listing Image for 909 Copp Rd 32 of 48 Listing Image for 909 Copp Rd 33 of 48 Listing Image for 909 Copp Rd 34 of 48 Listing Image for 909 Copp Rd 35 of 48 Listing Image for 909 Copp Rd 36 of 48 Listing Image for 909 Copp Rd 37 of 48 Listing Image for 909 Copp Rd 38 of 48 Listing Image for 909 Copp Rd 39 of 48 Listing Image for 909 Copp Rd 40 of 48 Listing Image for 909 Copp Rd 41 of 48 Listing Image for 909 Copp Rd 42 of 48 Listing Image for 909 Copp Rd 43 of 48 Listing Image for 909 Copp Rd 44 of 48 Listing Image for 909 Copp Rd 45 of 48 Listing Image for 909 Copp Rd 46 of 48 Listing Image for 909 Copp Rd 47 of 48 Listing Image for 909 Copp Rd 48 of 48

$2,050,000

↓ $100,000

Kula/Ulupalakua/Kanaio

909 Copp Rd, Kula/Ulupalakua/Kanaio

2 Beds 2 Baths 992 SqFt Residential MLS® # 406860 Date Sold: December 17, 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: 12/09/2025
Listing Image for 39 Ka Dr 1 of 38 Listing Image for 39 Ka Dr 2 of 38 Listing Image for 39 Ka Dr 3 of 38 Listing Image for 39 Ka Dr 4 of 38 Listing Image for 39 Ka Dr 5 of 38 Listing Image for 39 Ka Dr 6 of 38 Listing Image for 39 Ka Dr 7 of 38 Listing Image for 39 Ka Dr 8 of 38 Listing Image for 39 Ka Dr 9 of 38 Listing Image for 39 Ka Dr 10 of 38 Listing Image for 39 Ka Dr 11 of 38 Listing Image for 39 Ka Dr 12 of 38 Listing Image for 39 Ka Dr 13 of 38 Listing Image for 39 Ka Dr 14 of 38 Listing Image for 39 Ka Dr 15 of 38 Listing Image for 39 Ka Dr 16 of 38 Listing Image for 39 Ka Dr 17 of 38 Listing Image for 39 Ka Dr 18 of 38 Listing Image for 39 Ka Dr 19 of 38 Listing Image for 39 Ka Dr 20 of 38 Listing Image for 39 Ka Dr 21 of 38 Listing Image for 39 Ka Dr 22 of 38 Listing Image for 39 Ka Dr 23 of 38 Listing Image for 39 Ka Dr 24 of 38 Listing Image for 39 Ka Dr 25 of 38 Listing Image for 39 Ka Dr 26 of 38 Listing Image for 39 Ka Dr 27 of 38 Listing Image for 39 Ka Dr 28 of 38 Listing Image for 39 Ka Dr 29 of 38 Listing Image for 39 Ka Dr 30 of 38 Listing Image for 39 Ka Dr 31 of 38 Listing Image for 39 Ka Dr 32 of 38 Listing Image for 39 Ka Dr 33 of 38 Listing Image for 39 Ka Dr 34 of 38 Listing Image for 39 Ka Dr 35 of 38 Listing Image for 39 Ka Dr 36 of 38 Listing Image for 39 Ka Dr 37 of 38 Listing Image for 39 Ka Dr 38 of 38

$1,650,000

Kula Kai

39 Ka Dr, Kula/Ulupalakua/Kanaio

4 Beds 3 Baths 2,626 SqFt Residential MLS® # 406874 Date Sold: December 9, 2025
Sold
Closed: 01/23/2026
Listing Image for 461 Laulea Pl 1 of 34 Listing Image for 461 Laulea Pl 2 of 34 Listing Image for 461 Laulea Pl 3 of 34 Listing Image for 461 Laulea Pl 4 of 34 Listing Image for 461 Laulea Pl 5 of 34 Listing Image for 461 Laulea Pl 6 of 34 Listing Image for 461 Laulea Pl 7 of 34 Listing Image for 461 Laulea Pl 8 of 34 Listing Image for 461 Laulea Pl 9 of 34 Listing Image for 461 Laulea Pl 10 of 34 Listing Image for 461 Laulea Pl 11 of 34 Listing Image for 461 Laulea Pl 12 of 34 Listing Image for 461 Laulea Pl 13 of 34 Listing Image for 461 Laulea Pl 14 of 34 Listing Image for 461 Laulea Pl 15 of 34 Listing Image for 461 Laulea Pl 16 of 34 Listing Image for 461 Laulea Pl 17 of 34 Listing Image for 461 Laulea Pl 18 of 34 Listing Image for 461 Laulea Pl 19 of 34 Listing Image for 461 Laulea Pl 20 of 34 Listing Image for 461 Laulea Pl 21 of 34 Listing Image for 461 Laulea Pl 22 of 34 Listing Image for 461 Laulea Pl 23 of 34 Listing Image for 461 Laulea Pl 24 of 34 Listing Image for 461 Laulea Pl 25 of 34 Listing Image for 461 Laulea Pl 26 of 34 Listing Image for 461 Laulea Pl 27 of 34 Listing Image for 461 Laulea Pl 28 of 34 Listing Image for 461 Laulea Pl 29 of 34 Listing Image for 461 Laulea Pl 30 of 34 Listing Image for 461 Laulea Pl 31 of 34 Listing Image for 461 Laulea Pl 32 of 34 Listing Image for 461 Laulea Pl 33 of 34 Listing Image for 461 Laulea Pl 34 of 34

$7,950,000

Spreckelsville

461 Laulea Pl, Spreckelsville/Paia/Kuau

4 Beds 3.5 Baths 2,612 SqFt Residential MLS® # 406854 Date Sold: January 23, 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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