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

Sort by:
Listing Image for 99 Hui F Rd A & B 1 of 50 Listing Image for 99 Hui F Rd A & B 2 of 50 Listing Image for 99 Hui F Rd A & B 3 of 50 Listing Image for 99 Hui F Rd A & B 4 of 50 Listing Image for 99 Hui F Rd A & B 5 of 50 Listing Image for 99 Hui F Rd A & B 6 of 50 Listing Image for 99 Hui F Rd A & B 7 of 50 Listing Image for 99 Hui F Rd A & B 8 of 50 Listing Image for 99 Hui F Rd A & B 9 of 50 Listing Image for 99 Hui F Rd A & B 10 of 50 Listing Image for 99 Hui F Rd A & B 11 of 50 Listing Image for 99 Hui F Rd A & B 12 of 50 Listing Image for 99 Hui F Rd A & B 13 of 50 Listing Image for 99 Hui F Rd A & B 14 of 50 Listing Image for 99 Hui F Rd A & B 15 of 50 Listing Image for 99 Hui F Rd A & B 16 of 50 Listing Image for 99 Hui F Rd A & B 17 of 50 Listing Image for 99 Hui F Rd A & B 18 of 50 Listing Image for 99 Hui F Rd A & B 19 of 50 Listing Image for 99 Hui F Rd A & B 20 of 50 Listing Image for 99 Hui F Rd A & B 21 of 50 Listing Image for 99 Hui F Rd A & B 22 of 50 Listing Image for 99 Hui F Rd A & B 23 of 50 Listing Image for 99 Hui F Rd A & B 24 of 50 Listing Image for 99 Hui F Rd A & B 25 of 50 Listing Image for 99 Hui F Rd A & B 26 of 50 Listing Image for 99 Hui F Rd A & B 27 of 50 Listing Image for 99 Hui F Rd A & B 28 of 50 Listing Image for 99 Hui F Rd A & B 29 of 50 Listing Image for 99 Hui F Rd A & B 30 of 50 Listing Image for 99 Hui F Rd A & B 31 of 50 Listing Image for 99 Hui F Rd A & B 32 of 50 Listing Image for 99 Hui F Rd A & B 33 of 50 Listing Image for 99 Hui F Rd A & B 34 of 50 Listing Image for 99 Hui F Rd A & B 35 of 50 Listing Image for 99 Hui F Rd A & B 36 of 50 Listing Image for 99 Hui F Rd A & B 37 of 50 Listing Image for 99 Hui F Rd A & B 38 of 50 Listing Image for 99 Hui F Rd A & B 39 of 50 Listing Image for 99 Hui F Rd A & B 40 of 50 Listing Image for 99 Hui F Rd A & B 41 of 50 Listing Image for 99 Hui F Rd A & B 42 of 50 Listing Image for 99 Hui F Rd A & B 43 of 50 Listing Image for 99 Hui F Rd A & B 44 of 50 Listing Image for 99 Hui F Rd A & B 45 of 50 Listing Image for 99 Hui F Rd A & B 46 of 50 Listing Image for 99 Hui F Rd A & B 47 of 50 Listing Image for 99 Hui F Rd A & B 48 of 50 Listing Image for 99 Hui F Rd A & B 49 of 50 Listing Image for 99 Hui F Rd A & B 50 of 50

$3,299,000

Napili Villas Lot 12

99 Hui F Rd A & B, Napili/Kahana/Honokowai

6 Beds 6 Baths 3,892 SqFt Residential MLS® # 410406

Days on Market: 44

Coldwell Banker Island Prop-KP Cell: 808-721-9100

Short Term Rental
Listing Image for 3741 Lower Honoapiilani Rd 313 1 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 2 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 3 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 4 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 5 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 6 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 7 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 8 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 9 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 10 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 11 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 12 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 13 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 14 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 15 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 16 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 17 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 18 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 19 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 20 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 21 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 22 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 23 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 24 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 25 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 26 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 27 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 28 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 29 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 30 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 31 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 32 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 33 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 34 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 35 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 36 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 37 of 38 Listing Image for 3741 Lower Honoapiilani Rd 313 38 of 38

$1,050,000

Kulakane 313

3741 Lower Honoapiilani Rd 313, Napili/Kahana/Honokowai

2 Beds 2 Baths 858 SqFt Residential MLS® # 410404

Days on Market: 44

Coldwell Banker Island Prop-KP Cell: 808-276-6061

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

$1,385,000

↓ $110,000

HONOKEANA

16 Hooia Pl, Napili/Kahana/Honokowai

4 Beds 4 Baths 1,829 SqFt Residential MLS® # 410396

Days on Market: 45

Greg Smith Broker Inc

Listing Image for 305 Iini Way 1 of 48 Listing Image for 305 Iini Way 2 of 48 Listing Image for 305 Iini Way 3 of 48 Listing Image for 305 Iini Way 4 of 48 Listing Image for 305 Iini Way 5 of 48 Listing Image for 305 Iini Way 6 of 48 Listing Image for 305 Iini Way 7 of 48 Listing Image for 305 Iini Way 8 of 48 Listing Image for 305 Iini Way 9 of 48 Listing Image for 305 Iini Way 10 of 48 Listing Image for 305 Iini Way 11 of 48 Listing Image for 305 Iini Way 12 of 48 Listing Image for 305 Iini Way 13 of 48 Listing Image for 305 Iini Way 14 of 48 Listing Image for 305 Iini Way 15 of 48 Listing Image for 305 Iini Way 16 of 48 Listing Image for 305 Iini Way 17 of 48 Listing Image for 305 Iini Way 18 of 48 Listing Image for 305 Iini Way 19 of 48 Listing Image for 305 Iini Way 20 of 48 Listing Image for 305 Iini Way 21 of 48 Listing Image for 305 Iini Way 22 of 48 Listing Image for 305 Iini Way 23 of 48 Listing Image for 305 Iini Way 24 of 48 Listing Image for 305 Iini Way 25 of 48 Listing Image for 305 Iini Way 26 of 48 Listing Image for 305 Iini Way 27 of 48 Listing Image for 305 Iini Way 28 of 48 Listing Image for 305 Iini Way 29 of 48 Listing Image for 305 Iini Way 30 of 48 Listing Image for 305 Iini Way 31 of 48 Listing Image for 305 Iini Way 32 of 48 Listing Image for 305 Iini Way 33 of 48 Listing Image for 305 Iini Way 34 of 48 Listing Image for 305 Iini Way 35 of 48 Listing Image for 305 Iini Way 36 of 48 Listing Image for 305 Iini Way 37 of 48 Listing Image for 305 Iini Way 38 of 48 Listing Image for 305 Iini Way 39 of 48 Listing Image for 305 Iini Way 40 of 48 Listing Image for 305 Iini Way 41 of 48 Listing Image for 305 Iini Way 42 of 48 Listing Image for 305 Iini Way 43 of 48 Listing Image for 305 Iini Way 44 of 48 Listing Image for 305 Iini Way 45 of 48 Listing Image for 305 Iini Way 46 of 48 Listing Image for 305 Iini Way 47 of 48 Listing Image for 305 Iini Way 48 of 48

$1,390,000

↓ $30,000

Puu Koa

305 Iini Way, Makawao/Olinda/Haliimaile

4 Beds 3.5 Baths 2,108 SqFt Residential MLS® # 410393

Days on Market: 45

Equity One Real Estate Inc (M) Cell: 808-280-6076

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

$36,900,000

Maluaka Estaes

34 Maluaka Pl Unit 9, Wailea/Makena

5 Beds 5.5 Baths 6,517 SqFt Residential MLS® # 410387

Days on Market: 46

Discovery Makena Realty LLC Cell: 808-870-8000

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

$1,595,000

The Islands

25 Kamalei Cir, Kahului

3 Beds 3.5 Baths 2,344 SqFt Residential MLS® # 410386

Days on Market: 46

ENRG Realty

View 6 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: 05/22/2026
Listing Image for 250 Ulana St 1 of 49 Listing Image for 250 Ulana St 2 of 49 Listing Image for 250 Ulana St 3 of 49 Listing Image for 250 Ulana St 4 of 49 Listing Image for 250 Ulana St 5 of 49 Listing Image for 250 Ulana St 6 of 49 Listing Image for 250 Ulana St 7 of 49 Listing Image for 250 Ulana St 8 of 49 Listing Image for 250 Ulana St 9 of 49 Listing Image for 250 Ulana St 10 of 49 Listing Image for 250 Ulana St 11 of 49 Listing Image for 250 Ulana St 12 of 49 Listing Image for 250 Ulana St 13 of 49 Listing Image for 250 Ulana St 14 of 49 Listing Image for 250 Ulana St 15 of 49 Listing Image for 250 Ulana St 16 of 49 Listing Image for 250 Ulana St 17 of 49 Listing Image for 250 Ulana St 18 of 49 Listing Image for 250 Ulana St 19 of 49 Listing Image for 250 Ulana St 20 of 49 Listing Image for 250 Ulana St 21 of 49 Listing Image for 250 Ulana St 22 of 49 Listing Image for 250 Ulana St 23 of 49 Listing Image for 250 Ulana St 24 of 49 Listing Image for 250 Ulana St 25 of 49 Listing Image for 250 Ulana St 26 of 49 Listing Image for 250 Ulana St 27 of 49 Listing Image for 250 Ulana St 28 of 49 Listing Image for 250 Ulana St 29 of 49 Listing Image for 250 Ulana St 30 of 49 Listing Image for 250 Ulana St 31 of 49 Listing Image for 250 Ulana St 32 of 49 Listing Image for 250 Ulana St 33 of 49 Listing Image for 250 Ulana St 34 of 49 Listing Image for 250 Ulana St 35 of 49 Listing Image for 250 Ulana St 36 of 49 Listing Image for 250 Ulana St 37 of 49 Listing Image for 250 Ulana St 38 of 49 Listing Image for 250 Ulana St 39 of 49 Listing Image for 250 Ulana St 40 of 49 Listing Image for 250 Ulana St 41 of 49 Listing Image for 250 Ulana St 42 of 49 Listing Image for 250 Ulana St 43 of 49 Listing Image for 250 Ulana St 44 of 49 Listing Image for 250 Ulana St 45 of 49 Listing Image for 250 Ulana St 46 of 49 Listing Image for 250 Ulana St 47 of 49 Listing Image for 250 Ulana St 48 of 49 Listing Image for 250 Ulana St 49 of 49

$1,690,000

Maui Uplands

250 Ulana St, Makawao/Olinda/Haliimaile

3 Beds 2 Baths 1,312 SqFt Residential MLS® # 409264 Date Sold: May 22, 2026
Sold
Closed: 07/08/2026
Listing Image for 10 Wailea Ekolu Pl 506 1 of 29 Listing Image for 10 Wailea Ekolu Pl 506 2 of 29 Listing Image for 10 Wailea Ekolu Pl 506 3 of 29 Listing Image for 10 Wailea Ekolu Pl 506 4 of 29 Listing Image for 10 Wailea Ekolu Pl 506 5 of 29 Listing Image for 10 Wailea Ekolu Pl 506 6 of 29 Listing Image for 10 Wailea Ekolu Pl 506 7 of 29 Listing Image for 10 Wailea Ekolu Pl 506 8 of 29 Listing Image for 10 Wailea Ekolu Pl 506 9 of 29 Listing Image for 10 Wailea Ekolu Pl 506 10 of 29 Listing Image for 10 Wailea Ekolu Pl 506 11 of 29 Listing Image for 10 Wailea Ekolu Pl 506 12 of 29 Listing Image for 10 Wailea Ekolu Pl 506 13 of 29 Listing Image for 10 Wailea Ekolu Pl 506 14 of 29 Listing Image for 10 Wailea Ekolu Pl 506 15 of 29 Listing Image for 10 Wailea Ekolu Pl 506 16 of 29 Listing Image for 10 Wailea Ekolu Pl 506 17 of 29 Listing Image for 10 Wailea Ekolu Pl 506 18 of 29 Listing Image for 10 Wailea Ekolu Pl 506 19 of 29 Listing Image for 10 Wailea Ekolu Pl 506 20 of 29 Listing Image for 10 Wailea Ekolu Pl 506 21 of 29 Listing Image for 10 Wailea Ekolu Pl 506 22 of 29 Listing Image for 10 Wailea Ekolu Pl 506 23 of 29 Listing Image for 10 Wailea Ekolu Pl 506 24 of 29 Listing Image for 10 Wailea Ekolu Pl 506 25 of 29 Listing Image for 10 Wailea Ekolu Pl 506 26 of 29 Listing Image for 10 Wailea Ekolu Pl 506 27 of 29 Listing Image for 10 Wailea Ekolu Pl 506 28 of 29 Listing Image for 10 Wailea Ekolu Pl 506 29 of 29

$1,200,000

↓ $299,000

Wailea Ekolu 506

10 Wailea Ekolu Pl 506, Wailea/Makena

2 Beds 2 Baths 1,071 SqFt Residential MLS® # 409263 Date Sold: July 8, 2026
Sold
Closed: 05/28/2026
Listing Image for 374 Kalua Rd A 1 of 42 Listing Image for 374 Kalua Rd A 2 of 42 Listing Image for 374 Kalua Rd A 3 of 42 Listing Image for 374 Kalua Rd A 4 of 42 Listing Image for 374 Kalua Rd A 5 of 42 Listing Image for 374 Kalua Rd A 6 of 42 Listing Image for 374 Kalua Rd A 7 of 42 Listing Image for 374 Kalua Rd A 8 of 42 Listing Image for 374 Kalua Rd A 9 of 42 Listing Image for 374 Kalua Rd A 10 of 42 Listing Image for 374 Kalua Rd A 11 of 42 Listing Image for 374 Kalua Rd A 12 of 42 Listing Image for 374 Kalua Rd A 13 of 42 Listing Image for 374 Kalua Rd A 14 of 42 Listing Image for 374 Kalua Rd A 15 of 42 Listing Image for 374 Kalua Rd A 16 of 42 Listing Image for 374 Kalua Rd A 17 of 42 Listing Image for 374 Kalua Rd A 18 of 42 Listing Image for 374 Kalua Rd A 19 of 42 Listing Image for 374 Kalua Rd A 20 of 42 Listing Image for 374 Kalua Rd A 21 of 42 Listing Image for 374 Kalua Rd A 22 of 42 Listing Image for 374 Kalua Rd A 23 of 42 Listing Image for 374 Kalua Rd A 24 of 42 Listing Image for 374 Kalua Rd A 25 of 42 Listing Image for 374 Kalua Rd A 26 of 42 Listing Image for 374 Kalua Rd A 27 of 42 Listing Image for 374 Kalua Rd A 28 of 42 Listing Image for 374 Kalua Rd A 29 of 42 Listing Image for 374 Kalua Rd A 30 of 42 Listing Image for 374 Kalua Rd A 31 of 42 Listing Image for 374 Kalua Rd A 32 of 42 Listing Image for 374 Kalua Rd A 33 of 42 Listing Image for 374 Kalua Rd A 34 of 42 Listing Image for 374 Kalua Rd A 35 of 42 Listing Image for 374 Kalua Rd A 36 of 42 Listing Image for 374 Kalua Rd A 37 of 42 Listing Image for 374 Kalua Rd A 38 of 42 Listing Image for 374 Kalua Rd A 39 of 42 Listing Image for 374 Kalua Rd A 40 of 42 Listing Image for 374 Kalua Rd A 41 of 42 Listing Image for 374 Kalua Rd A 42 of 42

$785,000

Wailuku

374 Kalua Rd A, Wailuku

2 Beds 1 Bath 720 SqFt Residential MLS® # 409262 Date Sold: May 28, 2026
Sold
Closed: 09/08/2026
Listing Image for 3325 Mapu Pl 1 of 33 Listing Image for 3325 Mapu Pl 2 of 33 Listing Image for 3325 Mapu Pl 3 of 33 Listing Image for 3325 Mapu Pl 4 of 33 Listing Image for 3325 Mapu Pl 5 of 33 Listing Image for 3325 Mapu Pl 6 of 33 Listing Image for 3325 Mapu Pl 7 of 33 Listing Image for 3325 Mapu Pl 8 of 33 Listing Image for 3325 Mapu Pl 9 of 33 Listing Image for 3325 Mapu Pl 10 of 33 Listing Image for 3325 Mapu Pl 11 of 33 Listing Image for 3325 Mapu Pl 12 of 33 Listing Image for 3325 Mapu Pl 13 of 33 Listing Image for 3325 Mapu Pl 14 of 33 Listing Image for 3325 Mapu Pl 15 of 33 Listing Image for 3325 Mapu Pl 16 of 33 Listing Image for 3325 Mapu Pl 17 of 33 Listing Image for 3325 Mapu Pl 18 of 33 Listing Image for 3325 Mapu Pl 19 of 33 Listing Image for 3325 Mapu Pl 20 of 33 Listing Image for 3325 Mapu Pl 21 of 33 Listing Image for 3325 Mapu Pl 22 of 33 Listing Image for 3325 Mapu Pl 23 of 33 Listing Image for 3325 Mapu Pl 24 of 33 Listing Image for 3325 Mapu Pl 25 of 33 Listing Image for 3325 Mapu Pl 26 of 33 Listing Image for 3325 Mapu Pl 27 of 33 Listing Image for 3325 Mapu Pl 28 of 33 Listing Image for 3325 Mapu Pl 29 of 33 Listing Image for 3325 Mapu Pl 30 of 33 Listing Image for 3325 Mapu Pl 31 of 33 Listing Image for 3325 Mapu Pl 32 of 33 Listing Image for 3325 Mapu Pl 33 of 33

$1,200,000

↓ $135,000

Maui Meadows

3325 Mapu Pl, Maui Meadows

2 Beds 1 Bath 704 SqFt Residential MLS® # 409258 Date Sold: September 8, 2026
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: 08/18/2026
Listing Image for 4055 Mahinahina Pl 1 of 50 Listing Image for 4055 Mahinahina Pl 2 of 50 Listing Image for 4055 Mahinahina Pl 3 of 50 Listing Image for 4055 Mahinahina Pl 4 of 50 Listing Image for 4055 Mahinahina Pl 5 of 50 Listing Image for 4055 Mahinahina Pl 6 of 50 Listing Image for 4055 Mahinahina Pl 7 of 50 Listing Image for 4055 Mahinahina Pl 8 of 50 Listing Image for 4055 Mahinahina Pl 9 of 50 Listing Image for 4055 Mahinahina Pl 10 of 50 Listing Image for 4055 Mahinahina Pl 11 of 50 Listing Image for 4055 Mahinahina Pl 12 of 50 Listing Image for 4055 Mahinahina Pl 13 of 50 Listing Image for 4055 Mahinahina Pl 14 of 50 Listing Image for 4055 Mahinahina Pl 15 of 50 Listing Image for 4055 Mahinahina Pl 16 of 50 Listing Image for 4055 Mahinahina Pl 17 of 50 Listing Image for 4055 Mahinahina Pl 18 of 50 Listing Image for 4055 Mahinahina Pl 19 of 50 Listing Image for 4055 Mahinahina Pl 20 of 50 Listing Image for 4055 Mahinahina Pl 21 of 50 Listing Image for 4055 Mahinahina Pl 22 of 50 Listing Image for 4055 Mahinahina Pl 23 of 50 Listing Image for 4055 Mahinahina Pl 24 of 50 Listing Image for 4055 Mahinahina Pl 25 of 50 Listing Image for 4055 Mahinahina Pl 26 of 50 Listing Image for 4055 Mahinahina Pl 27 of 50 Listing Image for 4055 Mahinahina Pl 28 of 50 Listing Image for 4055 Mahinahina Pl 29 of 50 Listing Image for 4055 Mahinahina Pl 30 of 50 Listing Image for 4055 Mahinahina Pl 31 of 50 Listing Image for 4055 Mahinahina Pl 32 of 50 Listing Image for 4055 Mahinahina Pl 33 of 50 Listing Image for 4055 Mahinahina Pl 34 of 50 Listing Image for 4055 Mahinahina Pl 35 of 50 Listing Image for 4055 Mahinahina Pl 36 of 50 Listing Image for 4055 Mahinahina Pl 37 of 50 Listing Image for 4055 Mahinahina Pl 38 of 50 Listing Image for 4055 Mahinahina Pl 39 of 50 Listing Image for 4055 Mahinahina Pl 40 of 50 Listing Image for 4055 Mahinahina Pl 41 of 50 Listing Image for 4055 Mahinahina Pl 42 of 50 Listing Image for 4055 Mahinahina Pl 43 of 50 Listing Image for 4055 Mahinahina Pl 44 of 50 Listing Image for 4055 Mahinahina Pl 45 of 50 Listing Image for 4055 Mahinahina Pl 46 of 50 Listing Image for 4055 Mahinahina Pl 47 of 50 Listing Image for 4055 Mahinahina Pl 48 of 50 Listing Image for 4055 Mahinahina Pl 49 of 50 Listing Image for 4055 Mahinahina Pl 50 of 50

$1,360,000

↓ $90,000

Mahinahina

4055 Mahinahina Pl, Napili/Kahana/Honokowai

4 Beds 2.5 Baths 2,025 SqFt Residential MLS® # 409254 Date Sold: August 18, 2026
Sold
Closed: 06/12/2026
Listing Image for 690 Olinda Rd 1 of 50 Listing Image for 690 Olinda Rd 2 of 50 Listing Image for 690 Olinda Rd 3 of 50 Listing Image for 690 Olinda Rd 4 of 50 Listing Image for 690 Olinda Rd 5 of 50 Listing Image for 690 Olinda Rd 6 of 50 Listing Image for 690 Olinda Rd 7 of 50 Listing Image for 690 Olinda Rd 8 of 50 Listing Image for 690 Olinda Rd 9 of 50 Listing Image for 690 Olinda Rd 10 of 50 Listing Image for 690 Olinda Rd 11 of 50 Listing Image for 690 Olinda Rd 12 of 50 Listing Image for 690 Olinda Rd 13 of 50 Listing Image for 690 Olinda Rd 14 of 50 Listing Image for 690 Olinda Rd 15 of 50 Listing Image for 690 Olinda Rd 16 of 50 Listing Image for 690 Olinda Rd 17 of 50 Listing Image for 690 Olinda Rd 18 of 50 Listing Image for 690 Olinda Rd 19 of 50 Listing Image for 690 Olinda Rd 20 of 50 Listing Image for 690 Olinda Rd 21 of 50 Listing Image for 690 Olinda Rd 22 of 50 Listing Image for 690 Olinda Rd 23 of 50 Listing Image for 690 Olinda Rd 24 of 50 Listing Image for 690 Olinda Rd 25 of 50 Listing Image for 690 Olinda Rd 26 of 50 Listing Image for 690 Olinda Rd 27 of 50 Listing Image for 690 Olinda Rd 28 of 50 Listing Image for 690 Olinda Rd 29 of 50 Listing Image for 690 Olinda Rd 30 of 50 Listing Image for 690 Olinda Rd 31 of 50 Listing Image for 690 Olinda Rd 32 of 50 Listing Image for 690 Olinda Rd 33 of 50 Listing Image for 690 Olinda Rd 34 of 50 Listing Image for 690 Olinda Rd 35 of 50 Listing Image for 690 Olinda Rd 36 of 50 Listing Image for 690 Olinda Rd 37 of 50 Listing Image for 690 Olinda Rd 38 of 50 Listing Image for 690 Olinda Rd 39 of 50 Listing Image for 690 Olinda Rd 40 of 50 Listing Image for 690 Olinda Rd 41 of 50 Listing Image for 690 Olinda Rd 42 of 50 Listing Image for 690 Olinda Rd 43 of 50 Listing Image for 690 Olinda Rd 44 of 50 Listing Image for 690 Olinda Rd 45 of 50 Listing Image for 690 Olinda Rd 46 of 50 Listing Image for 690 Olinda Rd 47 of 50 Listing Image for 690 Olinda Rd 48 of 50 Listing Image for 690 Olinda Rd 49 of 50 Listing Image for 690 Olinda Rd 50 of 50

$2,550,000

Makawao/Olinda/Haliimaile

690 Olinda Rd, Makawao/Olinda/Haliimaile

3 Beds 2 Baths 2,643 SqFt Residential MLS® # 409252 Date Sold: June 12, 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.

Provide a valid email address.
Newsletter consent

Posted by Evan Harlow R(S) on

Enjoy this blog post? Click here to subscribe for updates

Tags

Email Send a link to post via Email

Leave A Comment

e.g. yourwebsitename.com
Please note that your email address is kept private upon posting.