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

$2,995,000

Takitani Farm

30 Mamao Pl, Haiku

3 Beds 2 Baths 2,430 SqFt Residential MLS® # 408713

Days on Market: 218

West Maui Land Company Inc

Listing Image for 82 Mamao Pl 1 of 20 Listing Image for 82 Mamao Pl 2 of 20 Listing Image for 82 Mamao Pl 3 of 20 Listing Image for 82 Mamao Pl 4 of 20 Listing Image for 82 Mamao Pl 5 of 20 Listing Image for 82 Mamao Pl 6 of 20 Listing Image for 82 Mamao Pl 7 of 20 Listing Image for 82 Mamao Pl 8 of 20 Listing Image for 82 Mamao Pl 9 of 20 Listing Image for 82 Mamao Pl 10 of 20 Listing Image for 82 Mamao Pl 11 of 20 Listing Image for 82 Mamao Pl 12 of 20 Listing Image for 82 Mamao Pl 13 of 20 Listing Image for 82 Mamao Pl 14 of 20 Listing Image for 82 Mamao Pl 15 of 20 Listing Image for 82 Mamao Pl 16 of 20 Listing Image for 82 Mamao Pl 17 of 20 Listing Image for 82 Mamao Pl 18 of 20 Listing Image for 82 Mamao Pl 19 of 20 Listing Image for 82 Mamao Pl 20 of 20

$999,999

↓ $99,001

Haiku

82 Mamao Pl, Haiku

4 Beds 3 Baths 1,520 SqFt Residential MLS® # 408710

Days on Market: 220

Keller Williams Realty Maui-Ka Cell: 808-268-2115

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

$1,595,000

↓ $100,000

Alaeloa 37

20 Hui Rd I 37, Napili/Kahana/Honokowai

3 Beds 2 Baths 1,420 SqFt Residential MLS® # 408707

Days on Market: 219

Coldwell Banker Island Prop-KP Cell: 808-250-1583

Listing Image for 3321 Old Haleakala Hwy 1 of 50 Listing Image for 3321 Old Haleakala Hwy 2 of 50 Listing Image for 3321 Old Haleakala Hwy 3 of 50 Listing Image for 3321 Old Haleakala Hwy 4 of 50 Listing Image for 3321 Old Haleakala Hwy 5 of 50 Listing Image for 3321 Old Haleakala Hwy 6 of 50 Listing Image for 3321 Old Haleakala Hwy 7 of 50 Listing Image for 3321 Old Haleakala Hwy 8 of 50 Listing Image for 3321 Old Haleakala Hwy 9 of 50 Listing Image for 3321 Old Haleakala Hwy 10 of 50 Listing Image for 3321 Old Haleakala Hwy 11 of 50 Listing Image for 3321 Old Haleakala Hwy 12 of 50 Listing Image for 3321 Old Haleakala Hwy 13 of 50 Listing Image for 3321 Old Haleakala Hwy 14 of 50 Listing Image for 3321 Old Haleakala Hwy 15 of 50 Listing Image for 3321 Old Haleakala Hwy 16 of 50 Listing Image for 3321 Old Haleakala Hwy 17 of 50 Listing Image for 3321 Old Haleakala Hwy 18 of 50 Listing Image for 3321 Old Haleakala Hwy 19 of 50 Listing Image for 3321 Old Haleakala Hwy 20 of 50 Listing Image for 3321 Old Haleakala Hwy 21 of 50 Listing Image for 3321 Old Haleakala Hwy 22 of 50 Listing Image for 3321 Old Haleakala Hwy 23 of 50 Listing Image for 3321 Old Haleakala Hwy 24 of 50 Listing Image for 3321 Old Haleakala Hwy 25 of 50 Listing Image for 3321 Old Haleakala Hwy 26 of 50 Listing Image for 3321 Old Haleakala Hwy 27 of 50 Listing Image for 3321 Old Haleakala Hwy 28 of 50 Listing Image for 3321 Old Haleakala Hwy 29 of 50 Listing Image for 3321 Old Haleakala Hwy 30 of 50 Listing Image for 3321 Old Haleakala Hwy 31 of 50 Listing Image for 3321 Old Haleakala Hwy 32 of 50 Listing Image for 3321 Old Haleakala Hwy 33 of 50 Listing Image for 3321 Old Haleakala Hwy 34 of 50 Listing Image for 3321 Old Haleakala Hwy 35 of 50 Listing Image for 3321 Old Haleakala Hwy 36 of 50 Listing Image for 3321 Old Haleakala Hwy 37 of 50 Listing Image for 3321 Old Haleakala Hwy 38 of 50 Listing Image for 3321 Old Haleakala Hwy 39 of 50 Listing Image for 3321 Old Haleakala Hwy 40 of 50 Listing Image for 3321 Old Haleakala Hwy 41 of 50 Listing Image for 3321 Old Haleakala Hwy 42 of 50 Listing Image for 3321 Old Haleakala Hwy 43 of 50 Listing Image for 3321 Old Haleakala Hwy 44 of 50 Listing Image for 3321 Old Haleakala Hwy 45 of 50 Listing Image for 3321 Old Haleakala Hwy 46 of 50 Listing Image for 3321 Old Haleakala Hwy 47 of 50 Listing Image for 3321 Old Haleakala Hwy 48 of 50 Listing Image for 3321 Old Haleakala Hwy 49 of 50 Listing Image for 3321 Old Haleakala Hwy 50 of 50

$895,000

↓ $50,000

Pukalani

3321 Old Haleakala Hwy, Pukalani

3 Beds 1 Bath 720 SqFt Residential MLS® # 408706

Days on Market: 218

eXp Realty Cell: 808-463-9801

Buying Real Estate on Maui

Buying Real Estate on Maui

Read Evan's complete guide to buying a home or condo on Maui.

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In Escrow Short Term Rental
Listing Image for 3445 Lower Honoapiilani Rd 727 1 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 2 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 3 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 4 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 5 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 6 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 7 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 8 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 9 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 10 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 11 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 12 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 13 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 14 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 15 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 16 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 17 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 18 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 19 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 20 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 21 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 22 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 23 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 24 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 25 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 26 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 27 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 28 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 29 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 30 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 31 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 32 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 33 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 34 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 35 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 36 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 37 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 38 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 39 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 40 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 41 of 42 Listing Image for 3445 Lower Honoapiilani Rd 727 42 of 42

$995,000

↓ $255,000

Kaanapali Shores 727

3445 Lower Honoapiilani Rd 727, Kaanapali

2 Beds 2 Baths 964 SqFt Residential MLS® # 408688

Days on Market: 221

Keller Williams Realty Maui-L Cell: 808-870-2525

Listing Image for 2673 Kamaile St 1 of 50 Listing Image for 2673 Kamaile St 2 of 50 Listing Image for 2673 Kamaile St 3 of 50 Listing Image for 2673 Kamaile St 4 of 50 Listing Image for 2673 Kamaile St 5 of 50 Listing Image for 2673 Kamaile St 6 of 50 Listing Image for 2673 Kamaile St 7 of 50 Listing Image for 2673 Kamaile St 8 of 50 Listing Image for 2673 Kamaile St 9 of 50 Listing Image for 2673 Kamaile St 10 of 50 Listing Image for 2673 Kamaile St 11 of 50 Listing Image for 2673 Kamaile St 12 of 50 Listing Image for 2673 Kamaile St 13 of 50 Listing Image for 2673 Kamaile St 14 of 50 Listing Image for 2673 Kamaile St 15 of 50 Listing Image for 2673 Kamaile St 16 of 50 Listing Image for 2673 Kamaile St 17 of 50 Listing Image for 2673 Kamaile St 18 of 50 Listing Image for 2673 Kamaile St 19 of 50 Listing Image for 2673 Kamaile St 20 of 50 Listing Image for 2673 Kamaile St 21 of 50 Listing Image for 2673 Kamaile St 22 of 50 Listing Image for 2673 Kamaile St 23 of 50 Listing Image for 2673 Kamaile St 24 of 50 Listing Image for 2673 Kamaile St 25 of 50 Listing Image for 2673 Kamaile St 26 of 50 Listing Image for 2673 Kamaile St 27 of 50 Listing Image for 2673 Kamaile St 28 of 50 Listing Image for 2673 Kamaile St 29 of 50 Listing Image for 2673 Kamaile St 30 of 50 Listing Image for 2673 Kamaile St 31 of 50 Listing Image for 2673 Kamaile St 32 of 50 Listing Image for 2673 Kamaile St 33 of 50 Listing Image for 2673 Kamaile St 34 of 50 Listing Image for 2673 Kamaile St 35 of 50 Listing Image for 2673 Kamaile St 36 of 50 Listing Image for 2673 Kamaile St 37 of 50 Listing Image for 2673 Kamaile St 38 of 50 Listing Image for 2673 Kamaile St 39 of 50 Listing Image for 2673 Kamaile St 40 of 50 Listing Image for 2673 Kamaile St 41 of 50 Listing Image for 2673 Kamaile St 42 of 50 Listing Image for 2673 Kamaile St 43 of 50 Listing Image for 2673 Kamaile St 44 of 50 Listing Image for 2673 Kamaile St 45 of 50 Listing Image for 2673 Kamaile St 46 of 50 Listing Image for 2673 Kamaile St 47 of 50 Listing Image for 2673 Kamaile St 48 of 50 Listing Image for 2673 Kamaile St 49 of 50 Listing Image for 2673 Kamaile St 50 of 50

$3,595,000

↓ $200,000

Wailuku Country Estates

2673 Kamaile St, Wailuku

4 Beds 5.5 Baths 6,596 SqFt Residential MLS® # 408673

Days on Market: 222

Compass-W

Short Term Rental
Listing Image for 2777 S Kihei Rd L-105 1 of 48 Listing Image for 2777 S Kihei Rd L-105 2 of 48 Listing Image for 2777 S Kihei Rd L-105 3 of 48 Listing Image for 2777 S Kihei Rd L-105 4 of 48 Listing Image for 2777 S Kihei Rd L-105 5 of 48 Listing Image for 2777 S Kihei Rd L-105 6 of 48 Listing Image for 2777 S Kihei Rd L-105 7 of 48 Listing Image for 2777 S Kihei Rd L-105 8 of 48 Listing Image for 2777 S Kihei Rd L-105 9 of 48 Listing Image for 2777 S Kihei Rd L-105 10 of 48 Listing Image for 2777 S Kihei Rd L-105 11 of 48 Listing Image for 2777 S Kihei Rd L-105 12 of 48 Listing Image for 2777 S Kihei Rd L-105 13 of 48 Listing Image for 2777 S Kihei Rd L-105 14 of 48 Listing Image for 2777 S Kihei Rd L-105 15 of 48 Listing Image for 2777 S Kihei Rd L-105 16 of 48 Listing Image for 2777 S Kihei Rd L-105 17 of 48 Listing Image for 2777 S Kihei Rd L-105 18 of 48 Listing Image for 2777 S Kihei Rd L-105 19 of 48 Listing Image for 2777 S Kihei Rd L-105 20 of 48 Listing Image for 2777 S Kihei Rd L-105 21 of 48 Listing Image for 2777 S Kihei Rd L-105 22 of 48 Listing Image for 2777 S Kihei Rd L-105 23 of 48 Listing Image for 2777 S Kihei Rd L-105 24 of 48 Listing Image for 2777 S Kihei Rd L-105 25 of 48 Listing Image for 2777 S Kihei Rd L-105 26 of 48 Listing Image for 2777 S Kihei Rd L-105 27 of 48 Listing Image for 2777 S Kihei Rd L-105 28 of 48 Listing Image for 2777 S Kihei Rd L-105 29 of 48 Listing Image for 2777 S Kihei Rd L-105 30 of 48 Listing Image for 2777 S Kihei Rd L-105 31 of 48 Listing Image for 2777 S Kihei Rd L-105 32 of 48 Listing Image for 2777 S Kihei Rd L-105 33 of 48 Listing Image for 2777 S Kihei Rd L-105 34 of 48 Listing Image for 2777 S Kihei Rd L-105 35 of 48 Listing Image for 2777 S Kihei Rd L-105 36 of 48 Listing Image for 2777 S Kihei Rd L-105 37 of 48 Listing Image for 2777 S Kihei Rd L-105 38 of 48 Listing Image for 2777 S Kihei Rd L-105 39 of 48 Listing Image for 2777 S Kihei Rd L-105 40 of 48 Listing Image for 2777 S Kihei Rd L-105 41 of 48 Listing Image for 2777 S Kihei Rd L-105 42 of 48 Listing Image for 2777 S Kihei Rd L-105 43 of 48 Listing Image for 2777 S Kihei Rd L-105 44 of 48 Listing Image for 2777 S Kihei Rd L-105 45 of 48 Listing Image for 2777 S Kihei Rd L-105 46 of 48 Listing Image for 2777 S Kihei Rd L-105 47 of 48 Listing Image for 2777 S Kihei Rd L-105 48 of 48

$899,000

Maui Kamaole L-105

2777 S Kihei Rd L-105, Kihei

1 Bed 2 Baths 1,039 SqFt Residential MLS® # 408658

Days on Market: 224

Compass Cell: 808-757-8053

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: 07/02/2026
Listing Image for 4850 Makena Alanui Rd E-205 1 of 45 Listing Image for 4850 Makena Alanui Rd E-205 2 of 45 Listing Image for 4850 Makena Alanui Rd E-205 3 of 45 Listing Image for 4850 Makena Alanui Rd E-205 4 of 45 Listing Image for 4850 Makena Alanui Rd E-205 5 of 45 Listing Image for 4850 Makena Alanui Rd E-205 6 of 45 Listing Image for 4850 Makena Alanui Rd E-205 7 of 45 Listing Image for 4850 Makena Alanui Rd E-205 8 of 45 Listing Image for 4850 Makena Alanui Rd E-205 9 of 45 Listing Image for 4850 Makena Alanui Rd E-205 10 of 45 Listing Image for 4850 Makena Alanui Rd E-205 11 of 45 Listing Image for 4850 Makena Alanui Rd E-205 12 of 45 Listing Image for 4850 Makena Alanui Rd E-205 13 of 45 Listing Image for 4850 Makena Alanui Rd E-205 14 of 45 Listing Image for 4850 Makena Alanui Rd E-205 15 of 45 Listing Image for 4850 Makena Alanui Rd E-205 16 of 45 Listing Image for 4850 Makena Alanui Rd E-205 17 of 45 Listing Image for 4850 Makena Alanui Rd E-205 18 of 45 Listing Image for 4850 Makena Alanui Rd E-205 19 of 45 Listing Image for 4850 Makena Alanui Rd E-205 20 of 45 Listing Image for 4850 Makena Alanui Rd E-205 21 of 45 Listing Image for 4850 Makena Alanui Rd E-205 22 of 45 Listing Image for 4850 Makena Alanui Rd E-205 23 of 45 Listing Image for 4850 Makena Alanui Rd E-205 24 of 45 Listing Image for 4850 Makena Alanui Rd E-205 25 of 45 Listing Image for 4850 Makena Alanui Rd E-205 26 of 45 Listing Image for 4850 Makena Alanui Rd E-205 27 of 45 Listing Image for 4850 Makena Alanui Rd E-205 28 of 45 Listing Image for 4850 Makena Alanui Rd E-205 29 of 45 Listing Image for 4850 Makena Alanui Rd E-205 30 of 45 Listing Image for 4850 Makena Alanui Rd E-205 31 of 45 Listing Image for 4850 Makena Alanui Rd E-205 32 of 45 Listing Image for 4850 Makena Alanui Rd E-205 33 of 45 Listing Image for 4850 Makena Alanui Rd E-205 34 of 45 Listing Image for 4850 Makena Alanui Rd E-205 35 of 45 Listing Image for 4850 Makena Alanui Rd E-205 36 of 45 Listing Image for 4850 Makena Alanui Rd E-205 37 of 45 Listing Image for 4850 Makena Alanui Rd E-205 38 of 45 Listing Image for 4850 Makena Alanui Rd E-205 39 of 45 Listing Image for 4850 Makena Alanui Rd E-205 40 of 45 Listing Image for 4850 Makena Alanui Rd E-205 41 of 45 Listing Image for 4850 Makena Alanui Rd E-205 42 of 45 Listing Image for 4850 Makena Alanui Rd E-205 43 of 45 Listing Image for 4850 Makena Alanui Rd E-205 44 of 45 Listing Image for 4850 Makena Alanui Rd E-205 45 of 45

$3,999,999

Makena Surf E-205

4850 Makena Alanui Rd E-205, Wailea/Makena

2 Beds 2 Baths 1,313 SqFt Residential MLS® # 407623 Date Sold: July 2, 2026
Sold
Closed: 12/11/2025
Listing Image for 70 Central Ave 1 of 50 Listing Image for 70 Central Ave 2 of 50 Listing Image for 70 Central Ave 3 of 50 Listing Image for 70 Central Ave 4 of 50 Listing Image for 70 Central Ave 5 of 50 Listing Image for 70 Central Ave 6 of 50 Listing Image for 70 Central Ave 7 of 50 Listing Image for 70 Central Ave 8 of 50 Listing Image for 70 Central Ave 9 of 50 Listing Image for 70 Central Ave 10 of 50 Listing Image for 70 Central Ave 11 of 50 Listing Image for 70 Central Ave 12 of 50 Listing Image for 70 Central Ave 13 of 50 Listing Image for 70 Central Ave 14 of 50 Listing Image for 70 Central Ave 15 of 50 Listing Image for 70 Central Ave 16 of 50 Listing Image for 70 Central Ave 17 of 50 Listing Image for 70 Central Ave 18 of 50 Listing Image for 70 Central Ave 19 of 50 Listing Image for 70 Central Ave 20 of 50 Listing Image for 70 Central Ave 21 of 50 Listing Image for 70 Central Ave 22 of 50 Listing Image for 70 Central Ave 23 of 50 Listing Image for 70 Central Ave 24 of 50 Listing Image for 70 Central Ave 25 of 50 Listing Image for 70 Central Ave 26 of 50 Listing Image for 70 Central Ave 27 of 50 Listing Image for 70 Central Ave 28 of 50 Listing Image for 70 Central Ave 29 of 50 Listing Image for 70 Central Ave 30 of 50 Listing Image for 70 Central Ave 31 of 50 Listing Image for 70 Central Ave 32 of 50 Listing Image for 70 Central Ave 33 of 50 Listing Image for 70 Central Ave 34 of 50 Listing Image for 70 Central Ave 35 of 50 Listing Image for 70 Central Ave 36 of 50 Listing Image for 70 Central Ave 37 of 50 Listing Image for 70 Central Ave 38 of 50 Listing Image for 70 Central Ave 39 of 50 Listing Image for 70 Central Ave 40 of 50 Listing Image for 70 Central Ave 41 of 50 Listing Image for 70 Central Ave 42 of 50 Listing Image for 70 Central Ave 43 of 50 Listing Image for 70 Central Ave 44 of 50 Listing Image for 70 Central Ave 45 of 50 Listing Image for 70 Central Ave 46 of 50 Listing Image for 70 Central Ave 47 of 50 Listing Image for 70 Central Ave 48 of 50 Listing Image for 70 Central Ave 49 of 50 Listing Image for 70 Central Ave 50 of 50

$1,500,000

Wailuku

70 Central Ave, Wailuku

0 Beds 0 Baths 0 SqFt Commercial Sale MLS® # 407621 Date Sold: December 11, 2025
Sold
Closed: 05/20/2026
Listing Image for 3036 Kalua Koi Rd 1 of 50 Listing Image for 3036 Kalua Koi Rd 2 of 50 Listing Image for 3036 Kalua Koi Rd 3 of 50 Listing Image for 3036 Kalua Koi Rd 4 of 50 Listing Image for 3036 Kalua Koi Rd 5 of 50 Listing Image for 3036 Kalua Koi Rd 6 of 50 Listing Image for 3036 Kalua Koi Rd 7 of 50 Listing Image for 3036 Kalua Koi Rd 8 of 50 Listing Image for 3036 Kalua Koi Rd 9 of 50 Listing Image for 3036 Kalua Koi Rd 10 of 50 Listing Image for 3036 Kalua Koi Rd 11 of 50 Listing Image for 3036 Kalua Koi Rd 12 of 50 Listing Image for 3036 Kalua Koi Rd 13 of 50 Listing Image for 3036 Kalua Koi Rd 14 of 50 Listing Image for 3036 Kalua Koi Rd 15 of 50 Listing Image for 3036 Kalua Koi Rd 16 of 50 Listing Image for 3036 Kalua Koi Rd 17 of 50 Listing Image for 3036 Kalua Koi Rd 18 of 50 Listing Image for 3036 Kalua Koi Rd 19 of 50 Listing Image for 3036 Kalua Koi Rd 20 of 50 Listing Image for 3036 Kalua Koi Rd 21 of 50 Listing Image for 3036 Kalua Koi Rd 22 of 50 Listing Image for 3036 Kalua Koi Rd 23 of 50 Listing Image for 3036 Kalua Koi Rd 24 of 50 Listing Image for 3036 Kalua Koi Rd 25 of 50 Listing Image for 3036 Kalua Koi Rd 26 of 50 Listing Image for 3036 Kalua Koi Rd 27 of 50 Listing Image for 3036 Kalua Koi Rd 28 of 50 Listing Image for 3036 Kalua Koi Rd 29 of 50 Listing Image for 3036 Kalua Koi Rd 30 of 50 Listing Image for 3036 Kalua Koi Rd 31 of 50 Listing Image for 3036 Kalua Koi Rd 32 of 50 Listing Image for 3036 Kalua Koi Rd 33 of 50 Listing Image for 3036 Kalua Koi Rd 34 of 50 Listing Image for 3036 Kalua Koi Rd 35 of 50 Listing Image for 3036 Kalua Koi Rd 36 of 50 Listing Image for 3036 Kalua Koi Rd 37 of 50 Listing Image for 3036 Kalua Koi Rd 38 of 50 Listing Image for 3036 Kalua Koi Rd 39 of 50 Listing Image for 3036 Kalua Koi Rd 40 of 50 Listing Image for 3036 Kalua Koi Rd 41 of 50 Listing Image for 3036 Kalua Koi Rd 42 of 50 Listing Image for 3036 Kalua Koi Rd 43 of 50 Listing Image for 3036 Kalua Koi Rd 44 of 50 Listing Image for 3036 Kalua Koi Rd 45 of 50 Listing Image for 3036 Kalua Koi Rd 46 of 50 Listing Image for 3036 Kalua Koi Rd 47 of 50 Listing Image for 3036 Kalua Koi Rd 48 of 50 Listing Image for 3036 Kalua Koi Rd 49 of 50 Listing Image for 3036 Kalua Koi Rd 50 of 50

$3,760,000

↓ $440,000

Papohaku Ranchlands

3036 Kalua Koi Rd, Molokai

2 Beds 2.5 Baths 3,794 SqFt Residential MLS® # 407620 Date Sold: May 20, 2026
Sold
Closed: 05/04/2026
Listing Image for 286 Humupea Pl 1 of 15 Listing Image for 286 Humupea Pl 2 of 15 Listing Image for 286 Humupea Pl 3 of 15 Listing Image for 286 Humupea Pl 4 of 15 Listing Image for 286 Humupea Pl 5 of 15 Listing Image for 286 Humupea Pl 6 of 15 Listing Image for 286 Humupea Pl 7 of 15 Listing Image for 286 Humupea Pl 8 of 15 Listing Image for 286 Humupea Pl 9 of 15 Listing Image for 286 Humupea Pl 10 of 15 Listing Image for 286 Humupea Pl 11 of 15 Listing Image for 286 Humupea Pl 12 of 15 Listing Image for 286 Humupea Pl 13 of 15 Listing Image for 286 Humupea Pl 14 of 15 Listing Image for 286 Humupea Pl 15 of 15

$1,200,000

↓ $50,000

Hale Pi'ilani

286 Humupea Pl, Kihei

5 Beds 4 Baths 2,588 SqFt Residential MLS® # 407619 Date Sold: May 4, 2026
Sold
Closed: 11/04/2025
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$1,200,000

Lahaina Shores PH 3

475 Front St Ph 3, Lahaina

1 Bed 2 Baths 1,050 SqFt Residential MLS® # 407614 Date Sold: November 4, 2025
Sold
Closed: 12/15/2025
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$910,000

Kaimana at Kehalani Subd

533 Akolea Pl, Wailuku

3 Beds 2 Baths 1,600 SqFt Residential MLS® # 407610 Date Sold: December 15, 2025
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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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