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 184 Lolowaa Pl 1 of 50 Listing Image for 184 Lolowaa Pl 2 of 50 Listing Image for 184 Lolowaa Pl 3 of 50 Listing Image for 184 Lolowaa Pl 4 of 50 Listing Image for 184 Lolowaa Pl 5 of 50 Listing Image for 184 Lolowaa Pl 6 of 50 Listing Image for 184 Lolowaa Pl 7 of 50 Listing Image for 184 Lolowaa Pl 8 of 50 Listing Image for 184 Lolowaa Pl 9 of 50 Listing Image for 184 Lolowaa Pl 10 of 50 Listing Image for 184 Lolowaa Pl 11 of 50 Listing Image for 184 Lolowaa Pl 12 of 50 Listing Image for 184 Lolowaa Pl 13 of 50 Listing Image for 184 Lolowaa Pl 14 of 50 Listing Image for 184 Lolowaa Pl 15 of 50 Listing Image for 184 Lolowaa Pl 16 of 50 Listing Image for 184 Lolowaa Pl 17 of 50 Listing Image for 184 Lolowaa Pl 18 of 50 Listing Image for 184 Lolowaa Pl 19 of 50 Listing Image for 184 Lolowaa Pl 20 of 50 Listing Image for 184 Lolowaa Pl 21 of 50 Listing Image for 184 Lolowaa Pl 22 of 50 Listing Image for 184 Lolowaa Pl 23 of 50 Listing Image for 184 Lolowaa Pl 24 of 50 Listing Image for 184 Lolowaa Pl 25 of 50 Listing Image for 184 Lolowaa Pl 26 of 50 Listing Image for 184 Lolowaa Pl 27 of 50 Listing Image for 184 Lolowaa Pl 28 of 50 Listing Image for 184 Lolowaa Pl 29 of 50 Listing Image for 184 Lolowaa Pl 30 of 50 Listing Image for 184 Lolowaa Pl 31 of 50 Listing Image for 184 Lolowaa Pl 32 of 50 Listing Image for 184 Lolowaa Pl 33 of 50 Listing Image for 184 Lolowaa Pl 34 of 50 Listing Image for 184 Lolowaa Pl 35 of 50 Listing Image for 184 Lolowaa Pl 36 of 50 Listing Image for 184 Lolowaa Pl 37 of 50 Listing Image for 184 Lolowaa Pl 38 of 50 Listing Image for 184 Lolowaa Pl 39 of 50 Listing Image for 184 Lolowaa Pl 40 of 50 Listing Image for 184 Lolowaa Pl 41 of 50 Listing Image for 184 Lolowaa Pl 42 of 50 Listing Image for 184 Lolowaa Pl 43 of 50 Listing Image for 184 Lolowaa Pl 44 of 50 Listing Image for 184 Lolowaa Pl 45 of 50 Listing Image for 184 Lolowaa Pl 46 of 50 Listing Image for 184 Lolowaa Pl 47 of 50 Listing Image for 184 Lolowaa Pl 48 of 50 Listing Image for 184 Lolowaa Pl 49 of 50 Listing Image for 184 Lolowaa Pl 50 of 50

$9,495,000

↓ $1,500,000

WAILEA GOLF ESTATES II

184 Lolowaa Pl, Wailea/Makena

4 Beds 4.5 Baths 3,777 SqFt Residential MLS® # 408267

Days on Market: 259

Compass-W

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

$1,599,500

↓ $50,500

Koa at Kehalani

29 Papakapu Pl, Wailuku

5 Beds 4.5 Baths 3,294 SqFt Residential MLS® # 408264

Days on Market: 259

Carol Ball & Assocs Cell: 808-283-9043

Listing Image for 2874 Ualani Pl 15 1 of 46 Listing Image for 2874 Ualani Pl 15 2 of 46 Listing Image for 2874 Ualani Pl 15 3 of 46 Listing Image for 2874 Ualani Pl 15 4 of 46 Listing Image for 2874 Ualani Pl 15 5 of 46 Listing Image for 2874 Ualani Pl 15 6 of 46 Listing Image for 2874 Ualani Pl 15 7 of 46 Listing Image for 2874 Ualani Pl 15 8 of 46 Listing Image for 2874 Ualani Pl 15 9 of 46 Listing Image for 2874 Ualani Pl 15 10 of 46 Listing Image for 2874 Ualani Pl 15 11 of 46 Listing Image for 2874 Ualani Pl 15 12 of 46 Listing Image for 2874 Ualani Pl 15 13 of 46 Listing Image for 2874 Ualani Pl 15 14 of 46 Listing Image for 2874 Ualani Pl 15 15 of 46 Listing Image for 2874 Ualani Pl 15 16 of 46 Listing Image for 2874 Ualani Pl 15 17 of 46 Listing Image for 2874 Ualani Pl 15 18 of 46 Listing Image for 2874 Ualani Pl 15 19 of 46 Listing Image for 2874 Ualani Pl 15 20 of 46 Listing Image for 2874 Ualani Pl 15 21 of 46 Listing Image for 2874 Ualani Pl 15 22 of 46 Listing Image for 2874 Ualani Pl 15 23 of 46 Listing Image for 2874 Ualani Pl 15 24 of 46 Listing Image for 2874 Ualani Pl 15 25 of 46 Listing Image for 2874 Ualani Pl 15 26 of 46 Listing Image for 2874 Ualani Pl 15 27 of 46 Listing Image for 2874 Ualani Pl 15 28 of 46 Listing Image for 2874 Ualani Pl 15 29 of 46 Listing Image for 2874 Ualani Pl 15 30 of 46 Listing Image for 2874 Ualani Pl 15 31 of 46 Listing Image for 2874 Ualani Pl 15 32 of 46 Listing Image for 2874 Ualani Pl 15 33 of 46 Listing Image for 2874 Ualani Pl 15 34 of 46 Listing Image for 2874 Ualani Pl 15 35 of 46 Listing Image for 2874 Ualani Pl 15 36 of 46 Listing Image for 2874 Ualani Pl 15 37 of 46 Listing Image for 2874 Ualani Pl 15 38 of 46 Listing Image for 2874 Ualani Pl 15 39 of 46 Listing Image for 2874 Ualani Pl 15 40 of 46 Listing Image for 2874 Ualani Pl 15 41 of 46 Listing Image for 2874 Ualani Pl 15 42 of 46 Listing Image for 2874 Ualani Pl 15 43 of 46 Listing Image for 2874 Ualani Pl 15 44 of 46 Listing Image for 2874 Ualani Pl 15 45 of 46 Listing Image for 2874 Ualani Pl 15 46 of 46

$1,395,000

↑ $5,000

Pukalani Terr & Country C

2874 Ualani Pl 15, Pukalani

4 Beds 3 Baths 2,476 SqFt Residential MLS® # 408229

Days on Market: 263

Romvari Realty Ltd

Listing Image for 3002 S Kihei Rd 1 of 31 Listing Image for 3002 S Kihei Rd 2 of 31 Listing Image for 3002 S Kihei Rd 3 of 31 Listing Image for 3002 S Kihei Rd 4 of 31 Listing Image for 3002 S Kihei Rd 5 of 31 Listing Image for 3002 S Kihei Rd 6 of 31 Listing Image for 3002 S Kihei Rd 7 of 31 Listing Image for 3002 S Kihei Rd 8 of 31 Listing Image for 3002 S Kihei Rd 9 of 31 Listing Image for 3002 S Kihei Rd 10 of 31 Listing Image for 3002 S Kihei Rd 11 of 31 Listing Image for 3002 S Kihei Rd 12 of 31 Listing Image for 3002 S Kihei Rd 13 of 31 Listing Image for 3002 S Kihei Rd 14 of 31 Listing Image for 3002 S Kihei Rd 15 of 31 Listing Image for 3002 S Kihei Rd 16 of 31 Listing Image for 3002 S Kihei Rd 17 of 31 Listing Image for 3002 S Kihei Rd 18 of 31 Listing Image for 3002 S Kihei Rd 19 of 31 Listing Image for 3002 S Kihei Rd 20 of 31 Listing Image for 3002 S Kihei Rd 21 of 31 Listing Image for 3002 S Kihei Rd 22 of 31 Listing Image for 3002 S Kihei Rd 23 of 31 Listing Image for 3002 S Kihei Rd 24 of 31 Listing Image for 3002 S Kihei Rd 25 of 31 Listing Image for 3002 S Kihei Rd 26 of 31 Listing Image for 3002 S Kihei Rd 27 of 31 Listing Image for 3002 S Kihei Rd 28 of 31 Listing Image for 3002 S Kihei Rd 29 of 31 Listing Image for 3002 S Kihei Rd 30 of 31 Listing Image for 3002 S Kihei Rd 31 of 31

$15,500,000

Keawakapu Beach

3002 S Kihei Rd, Kihei

3 Beds 3 Baths 5,468 SqFt Residential MLS® # 406314

Days on Market: 451

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

Short Term Rental
Listing Image for 81 Makakehau St Apt H-2 1 of 40 Listing Image for 81 Makakehau St Apt H-2 2 of 40 Listing Image for 81 Makakehau St Apt H-2 3 of 40 Listing Image for 81 Makakehau St Apt H-2 4 of 40 Listing Image for 81 Makakehau St Apt H-2 5 of 40 Listing Image for 81 Makakehau St Apt H-2 6 of 40 Listing Image for 81 Makakehau St Apt H-2 7 of 40 Listing Image for 81 Makakehau St Apt H-2 8 of 40 Listing Image for 81 Makakehau St Apt H-2 9 of 40 Listing Image for 81 Makakehau St Apt H-2 10 of 40 Listing Image for 81 Makakehau St Apt H-2 11 of 40 Listing Image for 81 Makakehau St Apt H-2 12 of 40 Listing Image for 81 Makakehau St Apt H-2 13 of 40 Listing Image for 81 Makakehau St Apt H-2 14 of 40 Listing Image for 81 Makakehau St Apt H-2 15 of 40 Listing Image for 81 Makakehau St Apt H-2 16 of 40 Listing Image for 81 Makakehau St Apt H-2 17 of 40 Listing Image for 81 Makakehau St Apt H-2 18 of 40 Listing Image for 81 Makakehau St Apt H-2 19 of 40 Listing Image for 81 Makakehau St Apt H-2 20 of 40 Listing Image for 81 Makakehau St Apt H-2 21 of 40 Listing Image for 81 Makakehau St Apt H-2 22 of 40 Listing Image for 81 Makakehau St Apt H-2 23 of 40 Listing Image for 81 Makakehau St Apt H-2 24 of 40 Listing Image for 81 Makakehau St Apt H-2 25 of 40 Listing Image for 81 Makakehau St Apt H-2 26 of 40 Listing Image for 81 Makakehau St Apt H-2 27 of 40 Listing Image for 81 Makakehau St Apt H-2 28 of 40 Listing Image for 81 Makakehau St Apt H-2 29 of 40 Listing Image for 81 Makakehau St Apt H-2 30 of 40 Listing Image for 81 Makakehau St Apt H-2 31 of 40 Listing Image for 81 Makakehau St Apt H-2 32 of 40 Listing Image for 81 Makakehau St Apt H-2 33 of 40 Listing Image for 81 Makakehau St Apt H-2 34 of 40 Listing Image for 81 Makakehau St Apt H-2 35 of 40 Listing Image for 81 Makakehau St Apt H-2 36 of 40 Listing Image for 81 Makakehau St Apt H-2 37 of 40 Listing Image for 81 Makakehau St Apt H-2 38 of 40 Listing Image for 81 Makakehau St Apt H-2 39 of 40 Listing Image for 81 Makakehau St Apt H-2 40 of 40

$4,999,999

↓ $100,001

Hoolei Apt H-2

81 Makakehau St Apt H-2, Wailea/Makena

3 Beds 3.5 Baths 2,426 SqFt Residential MLS® # 408222

Days on Market: 267

Coldwell Banker Island Prop(S) Cell: 808-214-7837

Short Term Rental
Listing Image for 150 Puukolii Rd 59 1 of 22 Listing Image for 150 Puukolii Rd 59 2 of 22 Listing Image for 150 Puukolii Rd 59 3 of 22 Listing Image for 150 Puukolii Rd 59 4 of 22 Listing Image for 150 Puukolii Rd 59 5 of 22 Listing Image for 150 Puukolii Rd 59 6 of 22 Listing Image for 150 Puukolii Rd 59 7 of 22 Listing Image for 150 Puukolii Rd 59 8 of 22 Listing Image for 150 Puukolii Rd 59 9 of 22 Listing Image for 150 Puukolii Rd 59 10 of 22 Listing Image for 150 Puukolii Rd 59 11 of 22 Listing Image for 150 Puukolii Rd 59 12 of 22 Listing Image for 150 Puukolii Rd 59 13 of 22 Listing Image for 150 Puukolii Rd 59 14 of 22 Listing Image for 150 Puukolii Rd 59 15 of 22 Listing Image for 150 Puukolii Rd 59 16 of 22 Listing Image for 150 Puukolii Rd 59 17 of 22 Listing Image for 150 Puukolii Rd 59 18 of 22 Listing Image for 150 Puukolii Rd 59 19 of 22 Listing Image for 150 Puukolii Rd 59 20 of 22 Listing Image for 150 Puukolii Rd 59 21 of 22 Listing Image for 150 Puukolii Rd 59 22 of 22

$995,000

Kaanapali Plantation 59

150 Puukolii Rd 59, Kaanapali

1 Bed 2 Baths 1,089 SqFt Residential MLS® # 408211

Days on Market: 268

Berkshire Hathaway Maui Prop-L

Listing Image for 5670 Hana Hwy 1 of 30 Listing Image for 5670 Hana Hwy 2 of 30 Listing Image for 5670 Hana Hwy 3 of 30 Listing Image for 5670 Hana Hwy 4 of 30 Listing Image for 5670 Hana Hwy 5 of 30 Listing Image for 5670 Hana Hwy 6 of 30 Listing Image for 5670 Hana Hwy 7 of 30 Listing Image for 5670 Hana Hwy 8 of 30 Listing Image for 5670 Hana Hwy 9 of 30 Listing Image for 5670 Hana Hwy 10 of 30 Listing Image for 5670 Hana Hwy 11 of 30 Listing Image for 5670 Hana Hwy 12 of 30 Listing Image for 5670 Hana Hwy 13 of 30 Listing Image for 5670 Hana Hwy 14 of 30 Listing Image for 5670 Hana Hwy 15 of 30 Listing Image for 5670 Hana Hwy 16 of 30 Listing Image for 5670 Hana Hwy 17 of 30 Listing Image for 5670 Hana Hwy 18 of 30 Listing Image for 5670 Hana Hwy 19 of 30 Listing Image for 5670 Hana Hwy 20 of 30 Listing Image for 5670 Hana Hwy 21 of 30 Listing Image for 5670 Hana Hwy 22 of 30 Listing Image for 5670 Hana Hwy 23 of 30 Listing Image for 5670 Hana Hwy 24 of 30 Listing Image for 5670 Hana Hwy 25 of 30 Listing Image for 5670 Hana Hwy 26 of 30 Listing Image for 5670 Hana Hwy 27 of 30 Listing Image for 5670 Hana Hwy 28 of 30 Listing Image for 5670 Hana Hwy 29 of 30 Listing Image for 5670 Hana Hwy 30 of 30

$35,000,000

Hana

5670 Hana Hwy, Hana

2 Beds 2 Baths 1,828 SqFt Residential MLS® # 408193

Days on Market: 269

Hawaii Life (PR) Cell: 808-346-7413

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: 11/21/2025
Listing Image for 147 Ponana St 1 of 44 Listing Image for 147 Ponana St 2 of 44 Listing Image for 147 Ponana St 3 of 44 Listing Image for 147 Ponana St 4 of 44 Listing Image for 147 Ponana St 5 of 44 Listing Image for 147 Ponana St 6 of 44 Listing Image for 147 Ponana St 7 of 44 Listing Image for 147 Ponana St 8 of 44 Listing Image for 147 Ponana St 9 of 44 Listing Image for 147 Ponana St 10 of 44 Listing Image for 147 Ponana St 11 of 44 Listing Image for 147 Ponana St 12 of 44 Listing Image for 147 Ponana St 13 of 44 Listing Image for 147 Ponana St 14 of 44 Listing Image for 147 Ponana St 15 of 44 Listing Image for 147 Ponana St 16 of 44 Listing Image for 147 Ponana St 17 of 44 Listing Image for 147 Ponana St 18 of 44 Listing Image for 147 Ponana St 19 of 44 Listing Image for 147 Ponana St 20 of 44 Listing Image for 147 Ponana St 21 of 44 Listing Image for 147 Ponana St 22 of 44 Listing Image for 147 Ponana St 23 of 44 Listing Image for 147 Ponana St 24 of 44 Listing Image for 147 Ponana St 25 of 44 Listing Image for 147 Ponana St 26 of 44 Listing Image for 147 Ponana St 27 of 44 Listing Image for 147 Ponana St 28 of 44 Listing Image for 147 Ponana St 29 of 44 Listing Image for 147 Ponana St 30 of 44 Listing Image for 147 Ponana St 31 of 44 Listing Image for 147 Ponana St 32 of 44 Listing Image for 147 Ponana St 33 of 44 Listing Image for 147 Ponana St 34 of 44 Listing Image for 147 Ponana St 35 of 44 Listing Image for 147 Ponana St 36 of 44 Listing Image for 147 Ponana St 37 of 44 Listing Image for 147 Ponana St 38 of 44 Listing Image for 147 Ponana St 39 of 44 Listing Image for 147 Ponana St 40 of 44 Listing Image for 147 Ponana St 41 of 44 Listing Image for 147 Ponana St 42 of 44 Listing Image for 147 Ponana St 43 of 44 Listing Image for 147 Ponana St 44 of 44

$1,875,000

Keawakapu Views

147 Ponana St, Kihei

3 Beds 2 Baths 1,988 SqFt Residential MLS® # 407386 Date Sold: November 21, 2025
Sold
Closed: 04/10/2026
Listing Image for 16 Kumu Niu Pl Unit A 1 of 39 Listing Image for 16 Kumu Niu Pl Unit A 2 of 39 Listing Image for 16 Kumu Niu Pl Unit A 3 of 39 Listing Image for 16 Kumu Niu Pl Unit A 4 of 39 Listing Image for 16 Kumu Niu Pl Unit A 5 of 39 Listing Image for 16 Kumu Niu Pl Unit A 6 of 39 Listing Image for 16 Kumu Niu Pl Unit A 7 of 39 Listing Image for 16 Kumu Niu Pl Unit A 8 of 39 Listing Image for 16 Kumu Niu Pl Unit A 9 of 39 Listing Image for 16 Kumu Niu Pl Unit A 10 of 39 Listing Image for 16 Kumu Niu Pl Unit A 11 of 39 Listing Image for 16 Kumu Niu Pl Unit A 12 of 39 Listing Image for 16 Kumu Niu Pl Unit A 13 of 39 Listing Image for 16 Kumu Niu Pl Unit A 14 of 39 Listing Image for 16 Kumu Niu Pl Unit A 15 of 39 Listing Image for 16 Kumu Niu Pl Unit A 16 of 39 Listing Image for 16 Kumu Niu Pl Unit A 17 of 39 Listing Image for 16 Kumu Niu Pl Unit A 18 of 39 Listing Image for 16 Kumu Niu Pl Unit A 19 of 39 Listing Image for 16 Kumu Niu Pl Unit A 20 of 39 Listing Image for 16 Kumu Niu Pl Unit A 21 of 39 Listing Image for 16 Kumu Niu Pl Unit A 22 of 39 Listing Image for 16 Kumu Niu Pl Unit A 23 of 39 Listing Image for 16 Kumu Niu Pl Unit A 24 of 39 Listing Image for 16 Kumu Niu Pl Unit A 25 of 39 Listing Image for 16 Kumu Niu Pl Unit A 26 of 39 Listing Image for 16 Kumu Niu Pl Unit A 27 of 39 Listing Image for 16 Kumu Niu Pl Unit A 28 of 39 Listing Image for 16 Kumu Niu Pl Unit A 29 of 39 Listing Image for 16 Kumu Niu Pl Unit A 30 of 39 Listing Image for 16 Kumu Niu Pl Unit A 31 of 39 Listing Image for 16 Kumu Niu Pl Unit A 32 of 39 Listing Image for 16 Kumu Niu Pl Unit A 33 of 39 Listing Image for 16 Kumu Niu Pl Unit A 34 of 39 Listing Image for 16 Kumu Niu Pl Unit A 35 of 39 Listing Image for 16 Kumu Niu Pl Unit A 36 of 39 Listing Image for 16 Kumu Niu Pl Unit A 37 of 39 Listing Image for 16 Kumu Niu Pl Unit A 38 of 39 Listing Image for 16 Kumu Niu Pl Unit A 39 of 39

$1,815,000

↓ $330,000

Mahanalua Nui III

16 Kumu Niu Pl Unit A, Lahaina

2 Beds 3 Baths 962 SqFt Residential MLS® # 407385 Date Sold: April 10, 2026
Sold
Closed: 04/24/2026
Listing Image for 27 Nanialii Pl E 1 of 42 Listing Image for 27 Nanialii Pl E 2 of 42 Listing Image for 27 Nanialii Pl E 3 of 42 Listing Image for 27 Nanialii Pl E 4 of 42 Listing Image for 27 Nanialii Pl E 5 of 42 Listing Image for 27 Nanialii Pl E 6 of 42 Listing Image for 27 Nanialii Pl E 7 of 42 Listing Image for 27 Nanialii Pl E 8 of 42 Listing Image for 27 Nanialii Pl E 9 of 42 Listing Image for 27 Nanialii Pl E 10 of 42 Listing Image for 27 Nanialii Pl E 11 of 42 Listing Image for 27 Nanialii Pl E 12 of 42 Listing Image for 27 Nanialii Pl E 13 of 42 Listing Image for 27 Nanialii Pl E 14 of 42 Listing Image for 27 Nanialii Pl E 15 of 42 Listing Image for 27 Nanialii Pl E 16 of 42 Listing Image for 27 Nanialii Pl E 17 of 42 Listing Image for 27 Nanialii Pl E 18 of 42 Listing Image for 27 Nanialii Pl E 19 of 42 Listing Image for 27 Nanialii Pl E 20 of 42 Listing Image for 27 Nanialii Pl E 21 of 42 Listing Image for 27 Nanialii Pl E 22 of 42 Listing Image for 27 Nanialii Pl E 23 of 42 Listing Image for 27 Nanialii Pl E 24 of 42 Listing Image for 27 Nanialii Pl E 25 of 42 Listing Image for 27 Nanialii Pl E 26 of 42 Listing Image for 27 Nanialii Pl E 27 of 42 Listing Image for 27 Nanialii Pl E 28 of 42 Listing Image for 27 Nanialii Pl E 29 of 42 Listing Image for 27 Nanialii Pl E 30 of 42 Listing Image for 27 Nanialii Pl E 31 of 42 Listing Image for 27 Nanialii Pl E 32 of 42 Listing Image for 27 Nanialii Pl E 33 of 42 Listing Image for 27 Nanialii Pl E 34 of 42 Listing Image for 27 Nanialii Pl E 35 of 42 Listing Image for 27 Nanialii Pl E 36 of 42 Listing Image for 27 Nanialii Pl E 37 of 42 Listing Image for 27 Nanialii Pl E 38 of 42 Listing Image for 27 Nanialii Pl E 39 of 42 Listing Image for 27 Nanialii Pl E 40 of 42 Listing Image for 27 Nanialii Pl E 41 of 42 Listing Image for 27 Nanialii Pl E 42 of 42

$1,025,000

↓ $270,000

Waiakoa House Lots

27 Nanialii Pl E, Kihei

3 Beds 2 Baths 1,008 SqFt Residential MLS® # 407381 Date Sold: April 24, 2026
Sold
Closed: 11/12/2025
Listing Image for 35 Heona Pl 1 of 40 Listing Image for 35 Heona Pl 2 of 40 Listing Image for 35 Heona Pl 3 of 40 Listing Image for 35 Heona Pl 4 of 40 Listing Image for 35 Heona Pl 5 of 40 Listing Image for 35 Heona Pl 6 of 40 Listing Image for 35 Heona Pl 7 of 40 Listing Image for 35 Heona Pl 8 of 40 Listing Image for 35 Heona Pl 9 of 40 Listing Image for 35 Heona Pl 10 of 40 Listing Image for 35 Heona Pl 11 of 40 Listing Image for 35 Heona Pl 12 of 40 Listing Image for 35 Heona Pl 13 of 40 Listing Image for 35 Heona Pl 14 of 40 Listing Image for 35 Heona Pl 15 of 40 Listing Image for 35 Heona Pl 16 of 40 Listing Image for 35 Heona Pl 17 of 40 Listing Image for 35 Heona Pl 18 of 40 Listing Image for 35 Heona Pl 19 of 40 Listing Image for 35 Heona Pl 20 of 40 Listing Image for 35 Heona Pl 21 of 40 Listing Image for 35 Heona Pl 22 of 40 Listing Image for 35 Heona Pl 23 of 40 Listing Image for 35 Heona Pl 24 of 40 Listing Image for 35 Heona Pl 25 of 40 Listing Image for 35 Heona Pl 26 of 40 Listing Image for 35 Heona Pl 27 of 40 Listing Image for 35 Heona Pl 28 of 40 Listing Image for 35 Heona Pl 29 of 40 Listing Image for 35 Heona Pl 30 of 40 Listing Image for 35 Heona Pl 31 of 40 Listing Image for 35 Heona Pl 32 of 40 Listing Image for 35 Heona Pl 33 of 40 Listing Image for 35 Heona Pl 34 of 40 Listing Image for 35 Heona Pl 35 of 40 Listing Image for 35 Heona Pl 36 of 40 Listing Image for 35 Heona Pl 37 of 40 Listing Image for 35 Heona Pl 38 of 40 Listing Image for 35 Heona Pl 39 of 40 Listing Image for 35 Heona Pl 40 of 40

$1,210,000

Kenolio Makai

35 Heona Pl, Kihei

3 Beds 2 Baths 1,243 SqFt Residential MLS® # 407380 Date Sold: November 12, 2025
Buying Real Estate on Maui

Buying Real Estate on Maui

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Sold
Closed: 01/16/2026
Listing Image for 3379 Kehala Dr 1 of 29 Listing Image for 3379 Kehala Dr 2 of 29 Listing Image for 3379 Kehala Dr 3 of 29 Listing Image for 3379 Kehala Dr 4 of 29 Listing Image for 3379 Kehala Dr 5 of 29 Listing Image for 3379 Kehala Dr 6 of 29 Listing Image for 3379 Kehala Dr 7 of 29 Listing Image for 3379 Kehala Dr 8 of 29 Listing Image for 3379 Kehala Dr 9 of 29 Listing Image for 3379 Kehala Dr 10 of 29 Listing Image for 3379 Kehala Dr 11 of 29 Listing Image for 3379 Kehala Dr 12 of 29 Listing Image for 3379 Kehala Dr 13 of 29 Listing Image for 3379 Kehala Dr 14 of 29 Listing Image for 3379 Kehala Dr 15 of 29 Listing Image for 3379 Kehala Dr 16 of 29 Listing Image for 3379 Kehala Dr 17 of 29 Listing Image for 3379 Kehala Dr 18 of 29 Listing Image for 3379 Kehala Dr 19 of 29 Listing Image for 3379 Kehala Dr 20 of 29 Listing Image for 3379 Kehala Dr 21 of 29 Listing Image for 3379 Kehala Dr 22 of 29 Listing Image for 3379 Kehala Dr 23 of 29 Listing Image for 3379 Kehala Dr 24 of 29 Listing Image for 3379 Kehala Dr 25 of 29 Listing Image for 3379 Kehala Dr 26 of 29 Listing Image for 3379 Kehala Dr 27 of 29 Listing Image for 3379 Kehala Dr 28 of 29 Listing Image for 3379 Kehala Dr 29 of 29

$2,200,000

Maui Meadows

3379 Kehala Dr, Maui Meadows

2 Beds 3 Baths 2,316 SqFt Residential MLS® # 407372 Date Sold: January 16, 2026
Sold
Closed: 11/07/2025
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$1,575,000

Kapalua Golf Villas 23P1-2

500 Kapalua Dr 23p1-2, Kapalua

2 Beds 2 Baths 1,407 SqFt Residential MLS® # 407368 Date Sold: November 7, 2025
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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