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:
Short Term Rental
Listing Image for 811 S Kihei Rd 2f 1 of 50 Listing Image for 811 S Kihei Rd 2f 2 of 50 Listing Image for 811 S Kihei Rd 2f 3 of 50 Listing Image for 811 S Kihei Rd 2f 4 of 50 Listing Image for 811 S Kihei Rd 2f 5 of 50 Listing Image for 811 S Kihei Rd 2f 6 of 50 Listing Image for 811 S Kihei Rd 2f 7 of 50 Listing Image for 811 S Kihei Rd 2f 8 of 50 Listing Image for 811 S Kihei Rd 2f 9 of 50 Listing Image for 811 S Kihei Rd 2f 10 of 50 Listing Image for 811 S Kihei Rd 2f 11 of 50 Listing Image for 811 S Kihei Rd 2f 12 of 50 Listing Image for 811 S Kihei Rd 2f 13 of 50 Listing Image for 811 S Kihei Rd 2f 14 of 50 Listing Image for 811 S Kihei Rd 2f 15 of 50 Listing Image for 811 S Kihei Rd 2f 16 of 50 Listing Image for 811 S Kihei Rd 2f 17 of 50 Listing Image for 811 S Kihei Rd 2f 18 of 50 Listing Image for 811 S Kihei Rd 2f 19 of 50 Listing Image for 811 S Kihei Rd 2f 20 of 50 Listing Image for 811 S Kihei Rd 2f 21 of 50 Listing Image for 811 S Kihei Rd 2f 22 of 50 Listing Image for 811 S Kihei Rd 2f 23 of 50 Listing Image for 811 S Kihei Rd 2f 24 of 50 Listing Image for 811 S Kihei Rd 2f 25 of 50 Listing Image for 811 S Kihei Rd 2f 26 of 50 Listing Image for 811 S Kihei Rd 2f 27 of 50 Listing Image for 811 S Kihei Rd 2f 28 of 50 Listing Image for 811 S Kihei Rd 2f 29 of 50 Listing Image for 811 S Kihei Rd 2f 30 of 50 Listing Image for 811 S Kihei Rd 2f 31 of 50 Listing Image for 811 S Kihei Rd 2f 32 of 50 Listing Image for 811 S Kihei Rd 2f 33 of 50 Listing Image for 811 S Kihei Rd 2f 34 of 50 Listing Image for 811 S Kihei Rd 2f 35 of 50 Listing Image for 811 S Kihei Rd 2f 36 of 50 Listing Image for 811 S Kihei Rd 2f 37 of 50 Listing Image for 811 S Kihei Rd 2f 38 of 50 Listing Image for 811 S Kihei Rd 2f 39 of 50 Listing Image for 811 S Kihei Rd 2f 40 of 50 Listing Image for 811 S Kihei Rd 2f 41 of 50 Listing Image for 811 S Kihei Rd 2f 42 of 50 Listing Image for 811 S Kihei Rd 2f 43 of 50 Listing Image for 811 S Kihei Rd 2f 44 of 50 Listing Image for 811 S Kihei Rd 2f 45 of 50 Listing Image for 811 S Kihei Rd 2f 46 of 50 Listing Image for 811 S Kihei Rd 2f 47 of 50 Listing Image for 811 S Kihei Rd 2f 48 of 50 Listing Image for 811 S Kihei Rd 2f 49 of 50 Listing Image for 811 S Kihei Rd 2f 50 of 50

$1,495,000

Koa Resort 2F

811 S Kihei Rd 2f, Kihei

3 Beds 2.5 Baths 1,798 SqFt Residential MLS® # 410209

Days on Market: 66

Keller Williams Realty Maui-Ki Cell: 808-344-3584

In Escrow
Listing Image for 160 Oluea Cir 1 of 50 Listing Image for 160 Oluea Cir 2 of 50 Listing Image for 160 Oluea Cir 3 of 50 Listing Image for 160 Oluea Cir 4 of 50 Listing Image for 160 Oluea Cir 5 of 50 Listing Image for 160 Oluea Cir 6 of 50 Listing Image for 160 Oluea Cir 7 of 50 Listing Image for 160 Oluea Cir 8 of 50 Listing Image for 160 Oluea Cir 9 of 50 Listing Image for 160 Oluea Cir 10 of 50 Listing Image for 160 Oluea Cir 11 of 50 Listing Image for 160 Oluea Cir 12 of 50 Listing Image for 160 Oluea Cir 13 of 50 Listing Image for 160 Oluea Cir 14 of 50 Listing Image for 160 Oluea Cir 15 of 50 Listing Image for 160 Oluea Cir 16 of 50 Listing Image for 160 Oluea Cir 17 of 50 Listing Image for 160 Oluea Cir 18 of 50 Listing Image for 160 Oluea Cir 19 of 50 Listing Image for 160 Oluea Cir 20 of 50 Listing Image for 160 Oluea Cir 21 of 50 Listing Image for 160 Oluea Cir 22 of 50 Listing Image for 160 Oluea Cir 23 of 50 Listing Image for 160 Oluea Cir 24 of 50 Listing Image for 160 Oluea Cir 25 of 50 Listing Image for 160 Oluea Cir 26 of 50 Listing Image for 160 Oluea Cir 27 of 50 Listing Image for 160 Oluea Cir 28 of 50 Listing Image for 160 Oluea Cir 29 of 50 Listing Image for 160 Oluea Cir 30 of 50 Listing Image for 160 Oluea Cir 31 of 50 Listing Image for 160 Oluea Cir 32 of 50 Listing Image for 160 Oluea Cir 33 of 50 Listing Image for 160 Oluea Cir 34 of 50 Listing Image for 160 Oluea Cir 35 of 50 Listing Image for 160 Oluea Cir 36 of 50 Listing Image for 160 Oluea Cir 37 of 50 Listing Image for 160 Oluea Cir 38 of 50 Listing Image for 160 Oluea Cir 39 of 50 Listing Image for 160 Oluea Cir 40 of 50 Listing Image for 160 Oluea Cir 41 of 50 Listing Image for 160 Oluea Cir 42 of 50 Listing Image for 160 Oluea Cir 43 of 50 Listing Image for 160 Oluea Cir 44 of 50 Listing Image for 160 Oluea Cir 45 of 50 Listing Image for 160 Oluea Cir 46 of 50 Listing Image for 160 Oluea Cir 47 of 50 Listing Image for 160 Oluea Cir 48 of 50 Listing Image for 160 Oluea Cir 49 of 50 Listing Image for 160 Oluea Cir 50 of 50

$1,250,000

Kamali'i Alayna

160 Oluea Cir, Kihei

4 Beds 2.5 Baths 2,289 SqFt Residential MLS® # 410203

Days on Market: 67

Century 21 Island Homes

Listing Image for 1375 Umeke Cir 101 1 of 50 Listing Image for 1375 Umeke Cir 101 2 of 50 Listing Image for 1375 Umeke Cir 101 3 of 50 Listing Image for 1375 Umeke Cir 101 4 of 50 Listing Image for 1375 Umeke Cir 101 5 of 50 Listing Image for 1375 Umeke Cir 101 6 of 50 Listing Image for 1375 Umeke Cir 101 7 of 50 Listing Image for 1375 Umeke Cir 101 8 of 50 Listing Image for 1375 Umeke Cir 101 9 of 50 Listing Image for 1375 Umeke Cir 101 10 of 50 Listing Image for 1375 Umeke Cir 101 11 of 50 Listing Image for 1375 Umeke Cir 101 12 of 50 Listing Image for 1375 Umeke Cir 101 13 of 50 Listing Image for 1375 Umeke Cir 101 14 of 50 Listing Image for 1375 Umeke Cir 101 15 of 50 Listing Image for 1375 Umeke Cir 101 16 of 50 Listing Image for 1375 Umeke Cir 101 17 of 50 Listing Image for 1375 Umeke Cir 101 18 of 50 Listing Image for 1375 Umeke Cir 101 19 of 50 Listing Image for 1375 Umeke Cir 101 20 of 50 Listing Image for 1375 Umeke Cir 101 21 of 50 Listing Image for 1375 Umeke Cir 101 22 of 50 Listing Image for 1375 Umeke Cir 101 23 of 50 Listing Image for 1375 Umeke Cir 101 24 of 50 Listing Image for 1375 Umeke Cir 101 25 of 50 Listing Image for 1375 Umeke Cir 101 26 of 50 Listing Image for 1375 Umeke Cir 101 27 of 50 Listing Image for 1375 Umeke Cir 101 28 of 50 Listing Image for 1375 Umeke Cir 101 29 of 50 Listing Image for 1375 Umeke Cir 101 30 of 50 Listing Image for 1375 Umeke Cir 101 31 of 50 Listing Image for 1375 Umeke Cir 101 32 of 50 Listing Image for 1375 Umeke Cir 101 33 of 50 Listing Image for 1375 Umeke Cir 101 34 of 50 Listing Image for 1375 Umeke Cir 101 35 of 50 Listing Image for 1375 Umeke Cir 101 36 of 50 Listing Image for 1375 Umeke Cir 101 37 of 50 Listing Image for 1375 Umeke Cir 101 38 of 50 Listing Image for 1375 Umeke Cir 101 39 of 50 Listing Image for 1375 Umeke Cir 101 40 of 50 Listing Image for 1375 Umeke Cir 101 41 of 50 Listing Image for 1375 Umeke Cir 101 42 of 50 Listing Image for 1375 Umeke Cir 101 43 of 50 Listing Image for 1375 Umeke Cir 101 44 of 50 Listing Image for 1375 Umeke Cir 101 45 of 50 Listing Image for 1375 Umeke Cir 101 46 of 50 Listing Image for 1375 Umeke Cir 101 47 of 50 Listing Image for 1375 Umeke Cir 101 48 of 50 Listing Image for 1375 Umeke Cir 101 49 of 50 Listing Image for 1375 Umeke Cir 101 50 of 50

$1,875,000

Hokulani Golf Villas

1375 Umeke Cir 101, Kihei

2 Beds 2 Baths 1,902 SqFt Residential MLS® # 410201

Days on Market: 67

Compass-W

Short Term Rental
Listing Image for 10 Wailea Ekolu Pl 1706 1 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 2 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 3 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 4 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 5 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 6 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 7 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 8 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 9 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 10 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 11 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 12 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 13 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 14 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 15 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 16 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 17 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 18 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 19 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 20 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 21 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 22 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 23 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 24 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 25 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 26 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 27 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 28 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 29 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 30 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 31 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 32 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 33 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 34 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 35 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 36 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 37 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 38 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 39 of 40 Listing Image for 10 Wailea Ekolu Pl 1706 40 of 40

$1,575,000

Wailea Ekolu 1706

10 Wailea Ekolu Pl 1706, Wailea/Makena

2 Beds 2 Baths 1,071 SqFt Residential MLS® # 410202

Days on Market: 67

Hawaii Life (W) Cell: 808-283-6791

Buying Real Estate on Maui

Buying Real Estate on Maui

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

Read the Guide
Listing Image for 1375 Umeke Cir 101 1 of 50 Listing Image for 1375 Umeke Cir 101 2 of 50 Listing Image for 1375 Umeke Cir 101 3 of 50 Listing Image for 1375 Umeke Cir 101 4 of 50 Listing Image for 1375 Umeke Cir 101 5 of 50 Listing Image for 1375 Umeke Cir 101 6 of 50 Listing Image for 1375 Umeke Cir 101 7 of 50 Listing Image for 1375 Umeke Cir 101 8 of 50 Listing Image for 1375 Umeke Cir 101 9 of 50 Listing Image for 1375 Umeke Cir 101 10 of 50 Listing Image for 1375 Umeke Cir 101 11 of 50 Listing Image for 1375 Umeke Cir 101 12 of 50 Listing Image for 1375 Umeke Cir 101 13 of 50 Listing Image for 1375 Umeke Cir 101 14 of 50 Listing Image for 1375 Umeke Cir 101 15 of 50 Listing Image for 1375 Umeke Cir 101 16 of 50 Listing Image for 1375 Umeke Cir 101 17 of 50 Listing Image for 1375 Umeke Cir 101 18 of 50 Listing Image for 1375 Umeke Cir 101 19 of 50 Listing Image for 1375 Umeke Cir 101 20 of 50 Listing Image for 1375 Umeke Cir 101 21 of 50 Listing Image for 1375 Umeke Cir 101 22 of 50 Listing Image for 1375 Umeke Cir 101 23 of 50 Listing Image for 1375 Umeke Cir 101 24 of 50 Listing Image for 1375 Umeke Cir 101 25 of 50 Listing Image for 1375 Umeke Cir 101 26 of 50 Listing Image for 1375 Umeke Cir 101 27 of 50 Listing Image for 1375 Umeke Cir 101 28 of 50 Listing Image for 1375 Umeke Cir 101 29 of 50 Listing Image for 1375 Umeke Cir 101 30 of 50 Listing Image for 1375 Umeke Cir 101 31 of 50 Listing Image for 1375 Umeke Cir 101 32 of 50 Listing Image for 1375 Umeke Cir 101 33 of 50 Listing Image for 1375 Umeke Cir 101 34 of 50 Listing Image for 1375 Umeke Cir 101 35 of 50 Listing Image for 1375 Umeke Cir 101 36 of 50 Listing Image for 1375 Umeke Cir 101 37 of 50 Listing Image for 1375 Umeke Cir 101 38 of 50 Listing Image for 1375 Umeke Cir 101 39 of 50 Listing Image for 1375 Umeke Cir 101 40 of 50 Listing Image for 1375 Umeke Cir 101 41 of 50 Listing Image for 1375 Umeke Cir 101 42 of 50 Listing Image for 1375 Umeke Cir 101 43 of 50 Listing Image for 1375 Umeke Cir 101 44 of 50 Listing Image for 1375 Umeke Cir 101 45 of 50 Listing Image for 1375 Umeke Cir 101 46 of 50 Listing Image for 1375 Umeke Cir 101 47 of 50 Listing Image for 1375 Umeke Cir 101 48 of 50 Listing Image for 1375 Umeke Cir 101 49 of 50 Listing Image for 1375 Umeke Cir 101 50 of 50

$1,875,000

Hokulani Golf Villas 101

1375 Umeke Cir 101, Kihei

2 Beds 2 Baths 1,902 SqFt Residential MLS® # 410200

Days on Market: 67

Compass-W

Listing Image for 60 E Huapala Pl Unit B 1 of 50 Listing Image for 60 E Huapala Pl Unit B 2 of 50 Listing Image for 60 E Huapala Pl Unit B 3 of 50 Listing Image for 60 E Huapala Pl Unit B 4 of 50 Listing Image for 60 E Huapala Pl Unit B 5 of 50 Listing Image for 60 E Huapala Pl Unit B 6 of 50 Listing Image for 60 E Huapala Pl Unit B 7 of 50 Listing Image for 60 E Huapala Pl Unit B 8 of 50 Listing Image for 60 E Huapala Pl Unit B 9 of 50 Listing Image for 60 E Huapala Pl Unit B 10 of 50 Listing Image for 60 E Huapala Pl Unit B 11 of 50 Listing Image for 60 E Huapala Pl Unit B 12 of 50 Listing Image for 60 E Huapala Pl Unit B 13 of 50 Listing Image for 60 E Huapala Pl Unit B 14 of 50 Listing Image for 60 E Huapala Pl Unit B 15 of 50 Listing Image for 60 E Huapala Pl Unit B 16 of 50 Listing Image for 60 E Huapala Pl Unit B 17 of 50 Listing Image for 60 E Huapala Pl Unit B 18 of 50 Listing Image for 60 E Huapala Pl Unit B 19 of 50 Listing Image for 60 E Huapala Pl Unit B 20 of 50 Listing Image for 60 E Huapala Pl Unit B 21 of 50 Listing Image for 60 E Huapala Pl Unit B 22 of 50 Listing Image for 60 E Huapala Pl Unit B 23 of 50 Listing Image for 60 E Huapala Pl Unit B 24 of 50 Listing Image for 60 E Huapala Pl Unit B 25 of 50 Listing Image for 60 E Huapala Pl Unit B 26 of 50 Listing Image for 60 E Huapala Pl Unit B 27 of 50 Listing Image for 60 E Huapala Pl Unit B 28 of 50 Listing Image for 60 E Huapala Pl Unit B 29 of 50 Listing Image for 60 E Huapala Pl Unit B 30 of 50 Listing Image for 60 E Huapala Pl Unit B 31 of 50 Listing Image for 60 E Huapala Pl Unit B 32 of 50 Listing Image for 60 E Huapala Pl Unit B 33 of 50 Listing Image for 60 E Huapala Pl Unit B 34 of 50 Listing Image for 60 E Huapala Pl Unit B 35 of 50 Listing Image for 60 E Huapala Pl Unit B 36 of 50 Listing Image for 60 E Huapala Pl Unit B 37 of 50 Listing Image for 60 E Huapala Pl Unit B 38 of 50 Listing Image for 60 E Huapala Pl Unit B 39 of 50 Listing Image for 60 E Huapala Pl Unit B 40 of 50 Listing Image for 60 E Huapala Pl Unit B 41 of 50 Listing Image for 60 E Huapala Pl Unit B 42 of 50 Listing Image for 60 E Huapala Pl Unit B 43 of 50 Listing Image for 60 E Huapala Pl Unit B 44 of 50 Listing Image for 60 E Huapala Pl Unit B 45 of 50 Listing Image for 60 E Huapala Pl Unit B 46 of 50 Listing Image for 60 E Huapala Pl Unit B 47 of 50 Listing Image for 60 E Huapala Pl Unit B 48 of 50 Listing Image for 60 E Huapala Pl Unit B 49 of 50 Listing Image for 60 E Huapala Pl Unit B 50 of 50

$2,300,000

↓ $150,000

Launiupoko

60 E Huapala Pl Unit B, Lahaina

2 Beds 1.5 Baths 1,024 SqFt Residential MLS® # 410197

Days on Market: 67

Island Sotheby's International Realty(L) Cell: 808-205-5201

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: 05/29/2026
Listing Image for 940 S Kihei Rd C304 1 of 41 Listing Image for 940 S Kihei Rd C304 2 of 41 Listing Image for 940 S Kihei Rd C304 3 of 41 Listing Image for 940 S Kihei Rd C304 4 of 41 Listing Image for 940 S Kihei Rd C304 5 of 41 Listing Image for 940 S Kihei Rd C304 6 of 41 Listing Image for 940 S Kihei Rd C304 7 of 41 Listing Image for 940 S Kihei Rd C304 8 of 41 Listing Image for 940 S Kihei Rd C304 9 of 41 Listing Image for 940 S Kihei Rd C304 10 of 41 Listing Image for 940 S Kihei Rd C304 11 of 41 Listing Image for 940 S Kihei Rd C304 12 of 41 Listing Image for 940 S Kihei Rd C304 13 of 41 Listing Image for 940 S Kihei Rd C304 14 of 41 Listing Image for 940 S Kihei Rd C304 15 of 41 Listing Image for 940 S Kihei Rd C304 16 of 41 Listing Image for 940 S Kihei Rd C304 17 of 41 Listing Image for 940 S Kihei Rd C304 18 of 41 Listing Image for 940 S Kihei Rd C304 19 of 41 Listing Image for 940 S Kihei Rd C304 20 of 41 Listing Image for 940 S Kihei Rd C304 21 of 41 Listing Image for 940 S Kihei Rd C304 22 of 41 Listing Image for 940 S Kihei Rd C304 23 of 41 Listing Image for 940 S Kihei Rd C304 24 of 41 Listing Image for 940 S Kihei Rd C304 25 of 41 Listing Image for 940 S Kihei Rd C304 26 of 41 Listing Image for 940 S Kihei Rd C304 27 of 41 Listing Image for 940 S Kihei Rd C304 28 of 41 Listing Image for 940 S Kihei Rd C304 29 of 41 Listing Image for 940 S Kihei Rd C304 30 of 41 Listing Image for 940 S Kihei Rd C304 31 of 41 Listing Image for 940 S Kihei Rd C304 32 of 41 Listing Image for 940 S Kihei Rd C304 33 of 41 Listing Image for 940 S Kihei Rd C304 34 of 41 Listing Image for 940 S Kihei Rd C304 35 of 41 Listing Image for 940 S Kihei Rd C304 36 of 41 Listing Image for 940 S Kihei Rd C304 37 of 41 Listing Image for 940 S Kihei Rd C304 38 of 41 Listing Image for 940 S Kihei Rd C304 39 of 41 Listing Image for 940 S Kihei Rd C304 40 of 41 Listing Image for 940 S Kihei Rd C304 41 of 41

$825,000

Luana Kai C304

940 S Kihei Rd C304, Kihei

2 Beds 2 Baths 963 SqFt Residential MLS® # 406272 Date Sold: May 29, 2026
Sold
Closed: 07/29/2026
Listing Image for 47 Poniu Cir 1 of 27 Listing Image for 47 Poniu Cir 2 of 27 Listing Image for 47 Poniu Cir 3 of 27 Listing Image for 47 Poniu Cir 4 of 27 Listing Image for 47 Poniu Cir 5 of 27 Listing Image for 47 Poniu Cir 6 of 27 Listing Image for 47 Poniu Cir 7 of 27 Listing Image for 47 Poniu Cir 8 of 27 Listing Image for 47 Poniu Cir 9 of 27 Listing Image for 47 Poniu Cir 10 of 27 Listing Image for 47 Poniu Cir 11 of 27 Listing Image for 47 Poniu Cir 12 of 27 Listing Image for 47 Poniu Cir 13 of 27 Listing Image for 47 Poniu Cir 14 of 27 Listing Image for 47 Poniu Cir 15 of 27 Listing Image for 47 Poniu Cir 16 of 27 Listing Image for 47 Poniu Cir 17 of 27 Listing Image for 47 Poniu Cir 18 of 27 Listing Image for 47 Poniu Cir 19 of 27 Listing Image for 47 Poniu Cir 20 of 27 Listing Image for 47 Poniu Cir 21 of 27 Listing Image for 47 Poniu Cir 22 of 27 Listing Image for 47 Poniu Cir 23 of 27 Listing Image for 47 Poniu Cir 24 of 27 Listing Image for 47 Poniu Cir 25 of 27 Listing Image for 47 Poniu Cir 26 of 27 Listing Image for 47 Poniu Cir 27 of 27

$1,075,000

Kaimana @ Kehalani

47 Poniu Cir, Wailuku

4 Beds 3 Baths 1,628 SqFt Residential MLS® # 408894 Date Sold: July 29, 2026
Sold
Closed: 07/29/2026
Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 1 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 2 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 3 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 4 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 5 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 6 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 7 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 8 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 9 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 10 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 11 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 12 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 13 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 14 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 15 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 16 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 17 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 18 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 19 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 20 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 21 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 22 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 23 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 24 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 25 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 26 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 27 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 28 of 29 Listing Image for 37 Hapua Pl Olena At Kehalani, Lot#3 29 of 29

$965,000

↓ $19,500

Olena At Kehalani

37 Hapua Pl Olena At Kehalani, Lot#3, Wailuku

3 Beds 2 Baths 1,474 SqFt Residential MLS® # 408891 Date Sold: July 29, 2026
Sold
Closed: 05/15/2026
Listing Image for 100 Woodrose Pl 1 of 50 Listing Image for 100 Woodrose Pl 2 of 50 Listing Image for 100 Woodrose Pl 3 of 50 Listing Image for 100 Woodrose Pl 4 of 50 Listing Image for 100 Woodrose Pl 5 of 50 Listing Image for 100 Woodrose Pl 6 of 50 Listing Image for 100 Woodrose Pl 7 of 50 Listing Image for 100 Woodrose Pl 8 of 50 Listing Image for 100 Woodrose Pl 9 of 50 Listing Image for 100 Woodrose Pl 10 of 50 Listing Image for 100 Woodrose Pl 11 of 50 Listing Image for 100 Woodrose Pl 12 of 50 Listing Image for 100 Woodrose Pl 13 of 50 Listing Image for 100 Woodrose Pl 14 of 50 Listing Image for 100 Woodrose Pl 15 of 50 Listing Image for 100 Woodrose Pl 16 of 50 Listing Image for 100 Woodrose Pl 17 of 50 Listing Image for 100 Woodrose Pl 18 of 50 Listing Image for 100 Woodrose Pl 19 of 50 Listing Image for 100 Woodrose Pl 20 of 50 Listing Image for 100 Woodrose Pl 21 of 50 Listing Image for 100 Woodrose Pl 22 of 50 Listing Image for 100 Woodrose Pl 23 of 50 Listing Image for 100 Woodrose Pl 24 of 50 Listing Image for 100 Woodrose Pl 25 of 50 Listing Image for 100 Woodrose Pl 26 of 50 Listing Image for 100 Woodrose Pl 27 of 50 Listing Image for 100 Woodrose Pl 28 of 50 Listing Image for 100 Woodrose Pl 29 of 50 Listing Image for 100 Woodrose Pl 30 of 50 Listing Image for 100 Woodrose Pl 31 of 50 Listing Image for 100 Woodrose Pl 32 of 50 Listing Image for 100 Woodrose Pl 33 of 50 Listing Image for 100 Woodrose Pl 34 of 50 Listing Image for 100 Woodrose Pl 35 of 50 Listing Image for 100 Woodrose Pl 36 of 50 Listing Image for 100 Woodrose Pl 37 of 50 Listing Image for 100 Woodrose Pl 38 of 50 Listing Image for 100 Woodrose Pl 39 of 50 Listing Image for 100 Woodrose Pl 40 of 50 Listing Image for 100 Woodrose Pl 41 of 50 Listing Image for 100 Woodrose Pl 42 of 50 Listing Image for 100 Woodrose Pl 43 of 50 Listing Image for 100 Woodrose Pl 44 of 50 Listing Image for 100 Woodrose Pl 45 of 50 Listing Image for 100 Woodrose Pl 46 of 50 Listing Image for 100 Woodrose Pl 47 of 50 Listing Image for 100 Woodrose Pl 48 of 50 Listing Image for 100 Woodrose Pl 49 of 50 Listing Image for 100 Woodrose Pl 50 of 50

$5,500,000

Pineaple Hill

100 Woodrose Pl, Kapalua

3 Beds 4.5 Baths 3,812 SqFt Residential MLS® # 408890 Date Sold: May 15, 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: 04/08/2026
Listing Image for 1032 S Kihei Rd B423 1 of 36 Listing Image for 1032 S Kihei Rd B423 2 of 36 Listing Image for 1032 S Kihei Rd B423 3 of 36 Listing Image for 1032 S Kihei Rd B423 4 of 36 Listing Image for 1032 S Kihei Rd B423 5 of 36 Listing Image for 1032 S Kihei Rd B423 6 of 36 Listing Image for 1032 S Kihei Rd B423 7 of 36 Listing Image for 1032 S Kihei Rd B423 8 of 36 Listing Image for 1032 S Kihei Rd B423 9 of 36 Listing Image for 1032 S Kihei Rd B423 10 of 36 Listing Image for 1032 S Kihei Rd B423 11 of 36 Listing Image for 1032 S Kihei Rd B423 12 of 36 Listing Image for 1032 S Kihei Rd B423 13 of 36 Listing Image for 1032 S Kihei Rd B423 14 of 36 Listing Image for 1032 S Kihei Rd B423 15 of 36 Listing Image for 1032 S Kihei Rd B423 16 of 36 Listing Image for 1032 S Kihei Rd B423 17 of 36 Listing Image for 1032 S Kihei Rd B423 18 of 36 Listing Image for 1032 S Kihei Rd B423 19 of 36 Listing Image for 1032 S Kihei Rd B423 20 of 36 Listing Image for 1032 S Kihei Rd B423 21 of 36 Listing Image for 1032 S Kihei Rd B423 22 of 36 Listing Image for 1032 S Kihei Rd B423 23 of 36 Listing Image for 1032 S Kihei Rd B423 24 of 36 Listing Image for 1032 S Kihei Rd B423 25 of 36 Listing Image for 1032 S Kihei Rd B423 26 of 36 Listing Image for 1032 S Kihei Rd B423 27 of 36 Listing Image for 1032 S Kihei Rd B423 28 of 36 Listing Image for 1032 S Kihei Rd B423 29 of 36 Listing Image for 1032 S Kihei Rd B423 30 of 36 Listing Image for 1032 S Kihei Rd B423 31 of 36 Listing Image for 1032 S Kihei Rd B423 32 of 36 Listing Image for 1032 S Kihei Rd B423 33 of 36 Listing Image for 1032 S Kihei Rd B423 34 of 36 Listing Image for 1032 S Kihei Rd B423 35 of 36 Listing Image for 1032 S Kihei Rd B423 36 of 36

$1,485,000

Maui Sunset B423

1032 S Kihei Rd B423, Kihei

3 Beds 3 Baths 1,392 SqFt Residential MLS® # 408882 Date Sold: April 8, 2026
Sold
Closed: 04/29/2026
Listing Image for 28 Ohia Lehua Pl 1 of 34 Listing Image for 28 Ohia Lehua Pl 2 of 34 Listing Image for 28 Ohia Lehua Pl 3 of 34 Listing Image for 28 Ohia Lehua Pl 4 of 34 Listing Image for 28 Ohia Lehua Pl 5 of 34 Listing Image for 28 Ohia Lehua Pl 6 of 34 Listing Image for 28 Ohia Lehua Pl 7 of 34 Listing Image for 28 Ohia Lehua Pl 8 of 34 Listing Image for 28 Ohia Lehua Pl 9 of 34 Listing Image for 28 Ohia Lehua Pl 10 of 34 Listing Image for 28 Ohia Lehua Pl 11 of 34 Listing Image for 28 Ohia Lehua Pl 12 of 34 Listing Image for 28 Ohia Lehua Pl 13 of 34 Listing Image for 28 Ohia Lehua Pl 14 of 34 Listing Image for 28 Ohia Lehua Pl 15 of 34 Listing Image for 28 Ohia Lehua Pl 16 of 34 Listing Image for 28 Ohia Lehua Pl 17 of 34 Listing Image for 28 Ohia Lehua Pl 18 of 34 Listing Image for 28 Ohia Lehua Pl 19 of 34 Listing Image for 28 Ohia Lehua Pl 20 of 34 Listing Image for 28 Ohia Lehua Pl 21 of 34 Listing Image for 28 Ohia Lehua Pl 22 of 34 Listing Image for 28 Ohia Lehua Pl 23 of 34 Listing Image for 28 Ohia Lehua Pl 24 of 34 Listing Image for 28 Ohia Lehua Pl 25 of 34 Listing Image for 28 Ohia Lehua Pl 26 of 34 Listing Image for 28 Ohia Lehua Pl 27 of 34 Listing Image for 28 Ohia Lehua Pl 28 of 34 Listing Image for 28 Ohia Lehua Pl 29 of 34 Listing Image for 28 Ohia Lehua Pl 30 of 34 Listing Image for 28 Ohia Lehua Pl 31 of 34 Listing Image for 28 Ohia Lehua Pl 32 of 34 Listing Image for 28 Ohia Lehua Pl 33 of 34 Listing Image for 28 Ohia Lehua Pl 34 of 34

$1,968,000

Kulamalu Hilltop

28 Ohia Lehua Pl, Pukalani

4 Beds 3.5 Baths 2,872 SqFt Residential MLS® # 408869 Date Sold: April 29, 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.