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 130 Kai Malina Pkwy Nr839 1 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 2 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 3 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 4 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 5 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 6 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 7 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 8 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 9 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 10 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 11 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 12 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 13 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 14 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 15 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 16 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 17 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 18 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 19 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 20 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 21 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 22 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 23 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 24 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 25 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 26 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 27 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 28 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 29 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 30 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 31 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 32 of 33 Listing Image for 130 Kai Malina Pkwy Nr839 33 of 33

$3,100,000

Honua Kai - Konea NR839

130 Kai Malina Pkwy Nr839, Kaanapali

2 Beds 2 Baths 1,325 SqFt Residential MLS® # 409926

Days on Market: 94

Susan Jackson Real Estate Cell: 865-206-1234

Listing Image for 270 Puumakani St 1 of 20 Listing Image for 270 Puumakani St 2 of 20 Listing Image for 270 Puumakani St 3 of 20 Listing Image for 270 Puumakani St 4 of 20 Listing Image for 270 Puumakani St 5 of 20 Listing Image for 270 Puumakani St 6 of 20 Listing Image for 270 Puumakani St 7 of 20 Listing Image for 270 Puumakani St 8 of 20 Listing Image for 270 Puumakani St 9 of 20 Listing Image for 270 Puumakani St 10 of 20 Listing Image for 270 Puumakani St 11 of 20 Listing Image for 270 Puumakani St 12 of 20 Listing Image for 270 Puumakani St 13 of 20 Listing Image for 270 Puumakani St 14 of 20 Listing Image for 270 Puumakani St 15 of 20 Listing Image for 270 Puumakani St 16 of 20 Listing Image for 270 Puumakani St 17 of 20 Listing Image for 270 Puumakani St 18 of 20 Listing Image for 270 Puumakani St 19 of 20 Listing Image for 270 Puumakani St 20 of 20

$1,345,000

↓ $30,000

Grand Fairway

270 Puumakani St, Kahului

3 Beds 2.5 Baths 1,715 SqFt Residential MLS® # 409922

Days on Market: 94

Maui Tropical Realty

Listing Image for 860 S Kihei Rd 1 of 50 Listing Image for 860 S Kihei Rd 2 of 50 Listing Image for 860 S Kihei Rd 3 of 50 Listing Image for 860 S Kihei Rd 4 of 50 Listing Image for 860 S Kihei Rd 5 of 50 Listing Image for 860 S Kihei Rd 6 of 50 Listing Image for 860 S Kihei Rd 7 of 50 Listing Image for 860 S Kihei Rd 8 of 50 Listing Image for 860 S Kihei Rd 9 of 50 Listing Image for 860 S Kihei Rd 10 of 50 Listing Image for 860 S Kihei Rd 11 of 50 Listing Image for 860 S Kihei Rd 12 of 50 Listing Image for 860 S Kihei Rd 13 of 50 Listing Image for 860 S Kihei Rd 14 of 50 Listing Image for 860 S Kihei Rd 15 of 50 Listing Image for 860 S Kihei Rd 16 of 50 Listing Image for 860 S Kihei Rd 17 of 50 Listing Image for 860 S Kihei Rd 18 of 50 Listing Image for 860 S Kihei Rd 19 of 50 Listing Image for 860 S Kihei Rd 20 of 50 Listing Image for 860 S Kihei Rd 21 of 50 Listing Image for 860 S Kihei Rd 22 of 50 Listing Image for 860 S Kihei Rd 23 of 50 Listing Image for 860 S Kihei Rd 24 of 50 Listing Image for 860 S Kihei Rd 25 of 50 Listing Image for 860 S Kihei Rd 26 of 50 Listing Image for 860 S Kihei Rd 27 of 50 Listing Image for 860 S Kihei Rd 28 of 50 Listing Image for 860 S Kihei Rd 29 of 50 Listing Image for 860 S Kihei Rd 30 of 50 Listing Image for 860 S Kihei Rd 31 of 50 Listing Image for 860 S Kihei Rd 32 of 50 Listing Image for 860 S Kihei Rd 33 of 50 Listing Image for 860 S Kihei Rd 34 of 50 Listing Image for 860 S Kihei Rd 35 of 50 Listing Image for 860 S Kihei Rd 36 of 50 Listing Image for 860 S Kihei Rd 37 of 50 Listing Image for 860 S Kihei Rd 38 of 50 Listing Image for 860 S Kihei Rd 39 of 50 Listing Image for 860 S Kihei Rd 40 of 50 Listing Image for 860 S Kihei Rd 41 of 50 Listing Image for 860 S Kihei Rd 42 of 50 Listing Image for 860 S Kihei Rd 43 of 50 Listing Image for 860 S Kihei Rd 44 of 50 Listing Image for 860 S Kihei Rd 45 of 50 Listing Image for 860 S Kihei Rd 46 of 50 Listing Image for 860 S Kihei Rd 47 of 50 Listing Image for 860 S Kihei Rd 48 of 50 Listing Image for 860 S Kihei Rd 49 of 50 Listing Image for 860 S Kihei Rd 50 of 50

$6,750,000

↓ $200,000

Kihei

860 S Kihei Rd, Kihei

5 Beds 5.5 Baths 4,201 SqFt Residential MLS® # 409921

Days on Market: 95

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

Listing Image for 3124 Nahenahe Pl 1 of 48 Listing Image for 3124 Nahenahe Pl 2 of 48 Listing Image for 3124 Nahenahe Pl 3 of 48 Listing Image for 3124 Nahenahe Pl 4 of 48 Listing Image for 3124 Nahenahe Pl 5 of 48 Listing Image for 3124 Nahenahe Pl 6 of 48 Listing Image for 3124 Nahenahe Pl 7 of 48 Listing Image for 3124 Nahenahe Pl 8 of 48 Listing Image for 3124 Nahenahe Pl 9 of 48 Listing Image for 3124 Nahenahe Pl 10 of 48 Listing Image for 3124 Nahenahe Pl 11 of 48 Listing Image for 3124 Nahenahe Pl 12 of 48 Listing Image for 3124 Nahenahe Pl 13 of 48 Listing Image for 3124 Nahenahe Pl 14 of 48 Listing Image for 3124 Nahenahe Pl 15 of 48 Listing Image for 3124 Nahenahe Pl 16 of 48 Listing Image for 3124 Nahenahe Pl 17 of 48 Listing Image for 3124 Nahenahe Pl 18 of 48 Listing Image for 3124 Nahenahe Pl 19 of 48 Listing Image for 3124 Nahenahe Pl 20 of 48 Listing Image for 3124 Nahenahe Pl 21 of 48 Listing Image for 3124 Nahenahe Pl 22 of 48 Listing Image for 3124 Nahenahe Pl 23 of 48 Listing Image for 3124 Nahenahe Pl 24 of 48 Listing Image for 3124 Nahenahe Pl 25 of 48 Listing Image for 3124 Nahenahe Pl 26 of 48 Listing Image for 3124 Nahenahe Pl 27 of 48 Listing Image for 3124 Nahenahe Pl 28 of 48 Listing Image for 3124 Nahenahe Pl 29 of 48 Listing Image for 3124 Nahenahe Pl 30 of 48 Listing Image for 3124 Nahenahe Pl 31 of 48 Listing Image for 3124 Nahenahe Pl 32 of 48 Listing Image for 3124 Nahenahe Pl 33 of 48 Listing Image for 3124 Nahenahe Pl 34 of 48 Listing Image for 3124 Nahenahe Pl 35 of 48 Listing Image for 3124 Nahenahe Pl 36 of 48 Listing Image for 3124 Nahenahe Pl 37 of 48 Listing Image for 3124 Nahenahe Pl 38 of 48 Listing Image for 3124 Nahenahe Pl 39 of 48 Listing Image for 3124 Nahenahe Pl 40 of 48 Listing Image for 3124 Nahenahe Pl 41 of 48 Listing Image for 3124 Nahenahe Pl 42 of 48 Listing Image for 3124 Nahenahe Pl 43 of 48 Listing Image for 3124 Nahenahe Pl 44 of 48 Listing Image for 3124 Nahenahe Pl 45 of 48 Listing Image for 3124 Nahenahe Pl 46 of 48 Listing Image for 3124 Nahenahe Pl 47 of 48 Listing Image for 3124 Nahenahe Pl 48 of 48

$2,250,000

↓ $250,000

Maui Meadows

3124 Nahenahe Pl, Maui Meadows

3 Beds 2 Baths 2,834 SqFt Residential MLS® # 409916

Days on Market: 95

Hawaii Life (W) Cell: 808-280-2055

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 9314 Kula Hwy Unit A 1 of 39 Listing Image for 9314 Kula Hwy Unit A 2 of 39 Listing Image for 9314 Kula Hwy Unit A 3 of 39 Listing Image for 9314 Kula Hwy Unit A 4 of 39 Listing Image for 9314 Kula Hwy Unit A 5 of 39 Listing Image for 9314 Kula Hwy Unit A 6 of 39 Listing Image for 9314 Kula Hwy Unit A 7 of 39 Listing Image for 9314 Kula Hwy Unit A 8 of 39 Listing Image for 9314 Kula Hwy Unit A 9 of 39 Listing Image for 9314 Kula Hwy Unit A 10 of 39 Listing Image for 9314 Kula Hwy Unit A 11 of 39 Listing Image for 9314 Kula Hwy Unit A 12 of 39 Listing Image for 9314 Kula Hwy Unit A 13 of 39 Listing Image for 9314 Kula Hwy Unit A 14 of 39 Listing Image for 9314 Kula Hwy Unit A 15 of 39 Listing Image for 9314 Kula Hwy Unit A 16 of 39 Listing Image for 9314 Kula Hwy Unit A 17 of 39 Listing Image for 9314 Kula Hwy Unit A 18 of 39 Listing Image for 9314 Kula Hwy Unit A 19 of 39 Listing Image for 9314 Kula Hwy Unit A 20 of 39 Listing Image for 9314 Kula Hwy Unit A 21 of 39 Listing Image for 9314 Kula Hwy Unit A 22 of 39 Listing Image for 9314 Kula Hwy Unit A 23 of 39 Listing Image for 9314 Kula Hwy Unit A 24 of 39 Listing Image for 9314 Kula Hwy Unit A 25 of 39 Listing Image for 9314 Kula Hwy Unit A 26 of 39 Listing Image for 9314 Kula Hwy Unit A 27 of 39 Listing Image for 9314 Kula Hwy Unit A 28 of 39 Listing Image for 9314 Kula Hwy Unit A 29 of 39 Listing Image for 9314 Kula Hwy Unit A 30 of 39 Listing Image for 9314 Kula Hwy Unit A 31 of 39 Listing Image for 9314 Kula Hwy Unit A 32 of 39 Listing Image for 9314 Kula Hwy Unit A 33 of 39 Listing Image for 9314 Kula Hwy Unit A 34 of 39 Listing Image for 9314 Kula Hwy Unit A 35 of 39 Listing Image for 9314 Kula Hwy Unit A 36 of 39 Listing Image for 9314 Kula Hwy Unit A 37 of 39 Listing Image for 9314 Kula Hwy Unit A 38 of 39 Listing Image for 9314 Kula Hwy Unit A 39 of 39

$2,600,000

Kula/Ulupalakua/Kanaio

9314 Kula Hwy Unit A, Kula/Ulupalakua/Kanaio

3 Beds 3 Baths 1,636 SqFt Residential MLS® # 409910

Days on Market: 95

Island Sotheby's International Realty(M) Cell: 808-283-2552

Listing Image for 78 Kai Malu Dr 101 (14a) 1 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 2 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 3 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 4 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 5 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 6 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 7 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 8 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 9 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 10 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 11 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 12 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 13 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 14 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 15 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 16 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 17 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 18 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 19 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 20 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 21 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 22 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 23 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 24 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 25 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 26 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 27 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 28 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 29 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 30 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 31 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 32 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 33 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 34 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 35 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 36 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 37 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 38 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 39 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 40 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 41 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 42 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 43 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 44 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 45 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 46 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 47 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 48 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 49 of 50 Listing Image for 78 Kai Malu Dr 101 (14a) 50 of 50

$3,878,000

La'i Loa 101 (14A)

78 Kai Malu Dr 101 (14a), Wailea/Makena

3 Beds 3 Baths 1,742 SqFt Residential MLS® # 409909

Days on Market: 95

Keller Williams Realty Maui-Ka Cell: 808-344-8038

Listing Image for 390 Pualoa Nani Pl 1 of 50 Listing Image for 390 Pualoa Nani Pl 2 of 50 Listing Image for 390 Pualoa Nani Pl 3 of 50 Listing Image for 390 Pualoa Nani Pl 4 of 50 Listing Image for 390 Pualoa Nani Pl 5 of 50 Listing Image for 390 Pualoa Nani Pl 6 of 50 Listing Image for 390 Pualoa Nani Pl 7 of 50 Listing Image for 390 Pualoa Nani Pl 8 of 50 Listing Image for 390 Pualoa Nani Pl 9 of 50 Listing Image for 390 Pualoa Nani Pl 10 of 50 Listing Image for 390 Pualoa Nani Pl 11 of 50 Listing Image for 390 Pualoa Nani Pl 12 of 50 Listing Image for 390 Pualoa Nani Pl 13 of 50 Listing Image for 390 Pualoa Nani Pl 14 of 50 Listing Image for 390 Pualoa Nani Pl 15 of 50 Listing Image for 390 Pualoa Nani Pl 16 of 50 Listing Image for 390 Pualoa Nani Pl 17 of 50 Listing Image for 390 Pualoa Nani Pl 18 of 50 Listing Image for 390 Pualoa Nani Pl 19 of 50 Listing Image for 390 Pualoa Nani Pl 20 of 50 Listing Image for 390 Pualoa Nani Pl 21 of 50 Listing Image for 390 Pualoa Nani Pl 22 of 50 Listing Image for 390 Pualoa Nani Pl 23 of 50 Listing Image for 390 Pualoa Nani Pl 24 of 50 Listing Image for 390 Pualoa Nani Pl 25 of 50 Listing Image for 390 Pualoa Nani Pl 26 of 50 Listing Image for 390 Pualoa Nani Pl 27 of 50 Listing Image for 390 Pualoa Nani Pl 28 of 50 Listing Image for 390 Pualoa Nani Pl 29 of 50 Listing Image for 390 Pualoa Nani Pl 30 of 50 Listing Image for 390 Pualoa Nani Pl 31 of 50 Listing Image for 390 Pualoa Nani Pl 32 of 50 Listing Image for 390 Pualoa Nani Pl 33 of 50 Listing Image for 390 Pualoa Nani Pl 34 of 50 Listing Image for 390 Pualoa Nani Pl 35 of 50 Listing Image for 390 Pualoa Nani Pl 36 of 50 Listing Image for 390 Pualoa Nani Pl 37 of 50 Listing Image for 390 Pualoa Nani Pl 38 of 50 Listing Image for 390 Pualoa Nani Pl 39 of 50 Listing Image for 390 Pualoa Nani Pl 40 of 50 Listing Image for 390 Pualoa Nani Pl 41 of 50 Listing Image for 390 Pualoa Nani Pl 42 of 50 Listing Image for 390 Pualoa Nani Pl 43 of 50 Listing Image for 390 Pualoa Nani Pl 44 of 50 Listing Image for 390 Pualoa Nani Pl 45 of 50 Listing Image for 390 Pualoa Nani Pl 46 of 50 Listing Image for 390 Pualoa Nani Pl 47 of 50 Listing Image for 390 Pualoa Nani Pl 48 of 50 Listing Image for 390 Pualoa Nani Pl 49 of 50 Listing Image for 390 Pualoa Nani Pl 50 of 50

$3,785,000

↓ $110,000

Wailea Pualani

390 Pualoa Nani Pl, Wailea/Makena

4 Beds 3.5 Baths 2,569 SqFt Residential MLS® # 409908

Days on Market: 95

Engel & Volkers Maui

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: 02/04/2026
Listing Image for 120 Lewa Lani Pl 17 1 of 4 Listing Image for 120 Lewa Lani Pl 17 2 of 4 Listing Image for 120 Lewa Lani Pl 17 3 of 4 Listing Image for 120 Lewa Lani Pl 17 4 of 4

$800,000

Kaanapali

120 Lewa Lani Pl 17, Kaanapali

0 Beds 0 Baths 0 SqFt Land MLS® # 408669 Date Sold: February 4, 2026
Sold
Closed: 04/10/2026
Listing Image for 11 Kainehe Pl 17b 1 of 47 Listing Image for 11 Kainehe Pl 17b 2 of 47 Listing Image for 11 Kainehe Pl 17b 3 of 47 Listing Image for 11 Kainehe Pl 17b 4 of 47 Listing Image for 11 Kainehe Pl 17b 5 of 47 Listing Image for 11 Kainehe Pl 17b 6 of 47 Listing Image for 11 Kainehe Pl 17b 7 of 47 Listing Image for 11 Kainehe Pl 17b 8 of 47 Listing Image for 11 Kainehe Pl 17b 9 of 47 Listing Image for 11 Kainehe Pl 17b 10 of 47 Listing Image for 11 Kainehe Pl 17b 11 of 47 Listing Image for 11 Kainehe Pl 17b 12 of 47 Listing Image for 11 Kainehe Pl 17b 13 of 47 Listing Image for 11 Kainehe Pl 17b 14 of 47 Listing Image for 11 Kainehe Pl 17b 15 of 47 Listing Image for 11 Kainehe Pl 17b 16 of 47 Listing Image for 11 Kainehe Pl 17b 17 of 47 Listing Image for 11 Kainehe Pl 17b 18 of 47 Listing Image for 11 Kainehe Pl 17b 19 of 47 Listing Image for 11 Kainehe Pl 17b 20 of 47 Listing Image for 11 Kainehe Pl 17b 21 of 47 Listing Image for 11 Kainehe Pl 17b 22 of 47 Listing Image for 11 Kainehe Pl 17b 23 of 47 Listing Image for 11 Kainehe Pl 17b 24 of 47 Listing Image for 11 Kainehe Pl 17b 25 of 47 Listing Image for 11 Kainehe Pl 17b 26 of 47 Listing Image for 11 Kainehe Pl 17b 27 of 47 Listing Image for 11 Kainehe Pl 17b 28 of 47 Listing Image for 11 Kainehe Pl 17b 29 of 47 Listing Image for 11 Kainehe Pl 17b 30 of 47 Listing Image for 11 Kainehe Pl 17b 31 of 47 Listing Image for 11 Kainehe Pl 17b 32 of 47 Listing Image for 11 Kainehe Pl 17b 33 of 47 Listing Image for 11 Kainehe Pl 17b 34 of 47 Listing Image for 11 Kainehe Pl 17b 35 of 47 Listing Image for 11 Kainehe Pl 17b 36 of 47 Listing Image for 11 Kainehe Pl 17b 37 of 47 Listing Image for 11 Kainehe Pl 17b 38 of 47 Listing Image for 11 Kainehe Pl 17b 39 of 47 Listing Image for 11 Kainehe Pl 17b 40 of 47 Listing Image for 11 Kainehe Pl 17b 41 of 47 Listing Image for 11 Kainehe Pl 17b 42 of 47 Listing Image for 11 Kainehe Pl 17b 43 of 47 Listing Image for 11 Kainehe Pl 17b 44 of 47 Listing Image for 11 Kainehe Pl 17b 45 of 47 Listing Image for 11 Kainehe Pl 17b 46 of 47 Listing Image for 11 Kainehe Pl 17b 47 of 47

$2,150,000

Kai Malu 17B

11 Kainehe Pl 17b, Wailea/Makena

3 Beds 2.5 Baths 1,796 SqFt Residential MLS® # 408666 Date Sold: April 10, 2026
Sold
Closed: 06/02/2026
Listing Image for 2960 S Kihei Rd 706 1 of 39 Listing Image for 2960 S Kihei Rd 706 2 of 39 Listing Image for 2960 S Kihei Rd 706 3 of 39 Listing Image for 2960 S Kihei Rd 706 4 of 39 Listing Image for 2960 S Kihei Rd 706 5 of 39 Listing Image for 2960 S Kihei Rd 706 6 of 39 Listing Image for 2960 S Kihei Rd 706 7 of 39 Listing Image for 2960 S Kihei Rd 706 8 of 39 Listing Image for 2960 S Kihei Rd 706 9 of 39 Listing Image for 2960 S Kihei Rd 706 10 of 39 Listing Image for 2960 S Kihei Rd 706 11 of 39 Listing Image for 2960 S Kihei Rd 706 12 of 39 Listing Image for 2960 S Kihei Rd 706 13 of 39 Listing Image for 2960 S Kihei Rd 706 14 of 39 Listing Image for 2960 S Kihei Rd 706 15 of 39 Listing Image for 2960 S Kihei Rd 706 16 of 39 Listing Image for 2960 S Kihei Rd 706 17 of 39 Listing Image for 2960 S Kihei Rd 706 18 of 39 Listing Image for 2960 S Kihei Rd 706 19 of 39 Listing Image for 2960 S Kihei Rd 706 20 of 39 Listing Image for 2960 S Kihei Rd 706 21 of 39 Listing Image for 2960 S Kihei Rd 706 22 of 39 Listing Image for 2960 S Kihei Rd 706 23 of 39 Listing Image for 2960 S Kihei Rd 706 24 of 39 Listing Image for 2960 S Kihei Rd 706 25 of 39 Listing Image for 2960 S Kihei Rd 706 26 of 39 Listing Image for 2960 S Kihei Rd 706 27 of 39 Listing Image for 2960 S Kihei Rd 706 28 of 39 Listing Image for 2960 S Kihei Rd 706 29 of 39 Listing Image for 2960 S Kihei Rd 706 30 of 39 Listing Image for 2960 S Kihei Rd 706 31 of 39 Listing Image for 2960 S Kihei Rd 706 32 of 39 Listing Image for 2960 S Kihei Rd 706 33 of 39 Listing Image for 2960 S Kihei Rd 706 34 of 39 Listing Image for 2960 S Kihei Rd 706 35 of 39 Listing Image for 2960 S Kihei Rd 706 36 of 39 Listing Image for 2960 S Kihei Rd 706 37 of 39 Listing Image for 2960 S Kihei Rd 706 38 of 39 Listing Image for 2960 S Kihei Rd 706 39 of 39

$1,800,000

↓ $175,000

Mana Kai 706

2960 S Kihei Rd 706, Kihei

2 Beds 2 Baths 767 SqFt Residential MLS® # 408661 Date Sold: June 2, 2026
Sold
Closed: 07/10/2026
Listing Image for 2960 S Kihei Rd 707 1 of 36 Listing Image for 2960 S Kihei Rd 707 2 of 36 Listing Image for 2960 S Kihei Rd 707 3 of 36 Listing Image for 2960 S Kihei Rd 707 4 of 36 Listing Image for 2960 S Kihei Rd 707 5 of 36 Listing Image for 2960 S Kihei Rd 707 6 of 36 Listing Image for 2960 S Kihei Rd 707 7 of 36 Listing Image for 2960 S Kihei Rd 707 8 of 36 Listing Image for 2960 S Kihei Rd 707 9 of 36 Listing Image for 2960 S Kihei Rd 707 10 of 36 Listing Image for 2960 S Kihei Rd 707 11 of 36 Listing Image for 2960 S Kihei Rd 707 12 of 36 Listing Image for 2960 S Kihei Rd 707 13 of 36 Listing Image for 2960 S Kihei Rd 707 14 of 36 Listing Image for 2960 S Kihei Rd 707 15 of 36 Listing Image for 2960 S Kihei Rd 707 16 of 36 Listing Image for 2960 S Kihei Rd 707 17 of 36 Listing Image for 2960 S Kihei Rd 707 18 of 36 Listing Image for 2960 S Kihei Rd 707 19 of 36 Listing Image for 2960 S Kihei Rd 707 20 of 36 Listing Image for 2960 S Kihei Rd 707 21 of 36 Listing Image for 2960 S Kihei Rd 707 22 of 36 Listing Image for 2960 S Kihei Rd 707 23 of 36 Listing Image for 2960 S Kihei Rd 707 24 of 36 Listing Image for 2960 S Kihei Rd 707 25 of 36 Listing Image for 2960 S Kihei Rd 707 26 of 36 Listing Image for 2960 S Kihei Rd 707 27 of 36 Listing Image for 2960 S Kihei Rd 707 28 of 36 Listing Image for 2960 S Kihei Rd 707 29 of 36 Listing Image for 2960 S Kihei Rd 707 30 of 36 Listing Image for 2960 S Kihei Rd 707 31 of 36 Listing Image for 2960 S Kihei Rd 707 32 of 36 Listing Image for 2960 S Kihei Rd 707 33 of 36 Listing Image for 2960 S Kihei Rd 707 34 of 36 Listing Image for 2960 S Kihei Rd 707 35 of 36 Listing Image for 2960 S Kihei Rd 707 36 of 36

$1,750,000

↓ $175,000

Mana Kai 707

2960 S Kihei Rd 707, Kihei

2 Beds 2 Baths 767 SqFt Residential MLS® # 408662 Date Sold: July 10, 2026
Sold
Closed: 04/30/2026
Listing Image for 572 Liholiho St 1 of 44 Listing Image for 572 Liholiho St 2 of 44 Listing Image for 572 Liholiho St 3 of 44 Listing Image for 572 Liholiho St 4 of 44 Listing Image for 572 Liholiho St 5 of 44 Listing Image for 572 Liholiho St 6 of 44 Listing Image for 572 Liholiho St 7 of 44 Listing Image for 572 Liholiho St 8 of 44 Listing Image for 572 Liholiho St 9 of 44 Listing Image for 572 Liholiho St 10 of 44 Listing Image for 572 Liholiho St 11 of 44 Listing Image for 572 Liholiho St 12 of 44 Listing Image for 572 Liholiho St 13 of 44 Listing Image for 572 Liholiho St 14 of 44 Listing Image for 572 Liholiho St 15 of 44 Listing Image for 572 Liholiho St 16 of 44 Listing Image for 572 Liholiho St 17 of 44 Listing Image for 572 Liholiho St 18 of 44 Listing Image for 572 Liholiho St 19 of 44 Listing Image for 572 Liholiho St 20 of 44 Listing Image for 572 Liholiho St 21 of 44 Listing Image for 572 Liholiho St 22 of 44 Listing Image for 572 Liholiho St 23 of 44 Listing Image for 572 Liholiho St 24 of 44 Listing Image for 572 Liholiho St 25 of 44 Listing Image for 572 Liholiho St 26 of 44 Listing Image for 572 Liholiho St 27 of 44 Listing Image for 572 Liholiho St 28 of 44 Listing Image for 572 Liholiho St 29 of 44 Listing Image for 572 Liholiho St 30 of 44 Listing Image for 572 Liholiho St 31 of 44 Listing Image for 572 Liholiho St 32 of 44 Listing Image for 572 Liholiho St 33 of 44 Listing Image for 572 Liholiho St 34 of 44 Listing Image for 572 Liholiho St 35 of 44 Listing Image for 572 Liholiho St 36 of 44 Listing Image for 572 Liholiho St 37 of 44 Listing Image for 572 Liholiho St 38 of 44 Listing Image for 572 Liholiho St 39 of 44 Listing Image for 572 Liholiho St 40 of 44 Listing Image for 572 Liholiho St 41 of 44 Listing Image for 572 Liholiho St 42 of 44 Listing Image for 572 Liholiho St 43 of 44 Listing Image for 572 Liholiho St 44 of 44

$1,265,000

Wailuku

572 Liholiho St, Wailuku

6 Beds 3 Baths 2,152 SqFt Residential MLS® # 408660 Date Sold: April 30, 2026
Sold
Closed: 03/31/2026
Listing Image for 8040 Hana Hwy 1 of 50 Listing Image for 8040 Hana Hwy 2 of 50 Listing Image for 8040 Hana Hwy 3 of 50 Listing Image for 8040 Hana Hwy 4 of 50 Listing Image for 8040 Hana Hwy 5 of 50 Listing Image for 8040 Hana Hwy 6 of 50 Listing Image for 8040 Hana Hwy 7 of 50 Listing Image for 8040 Hana Hwy 8 of 50 Listing Image for 8040 Hana Hwy 9 of 50 Listing Image for 8040 Hana Hwy 10 of 50 Listing Image for 8040 Hana Hwy 11 of 50 Listing Image for 8040 Hana Hwy 12 of 50 Listing Image for 8040 Hana Hwy 13 of 50 Listing Image for 8040 Hana Hwy 14 of 50 Listing Image for 8040 Hana Hwy 15 of 50 Listing Image for 8040 Hana Hwy 16 of 50 Listing Image for 8040 Hana Hwy 17 of 50 Listing Image for 8040 Hana Hwy 18 of 50 Listing Image for 8040 Hana Hwy 19 of 50 Listing Image for 8040 Hana Hwy 20 of 50 Listing Image for 8040 Hana Hwy 21 of 50 Listing Image for 8040 Hana Hwy 22 of 50 Listing Image for 8040 Hana Hwy 23 of 50 Listing Image for 8040 Hana Hwy 24 of 50 Listing Image for 8040 Hana Hwy 25 of 50 Listing Image for 8040 Hana Hwy 26 of 50 Listing Image for 8040 Hana Hwy 27 of 50 Listing Image for 8040 Hana Hwy 28 of 50 Listing Image for 8040 Hana Hwy 29 of 50 Listing Image for 8040 Hana Hwy 30 of 50 Listing Image for 8040 Hana Hwy 31 of 50 Listing Image for 8040 Hana Hwy 32 of 50 Listing Image for 8040 Hana Hwy 33 of 50 Listing Image for 8040 Hana Hwy 34 of 50 Listing Image for 8040 Hana Hwy 35 of 50 Listing Image for 8040 Hana Hwy 36 of 50 Listing Image for 8040 Hana Hwy 37 of 50 Listing Image for 8040 Hana Hwy 38 of 50 Listing Image for 8040 Hana Hwy 39 of 50 Listing Image for 8040 Hana Hwy 40 of 50 Listing Image for 8040 Hana Hwy 41 of 50 Listing Image for 8040 Hana Hwy 42 of 50 Listing Image for 8040 Hana Hwy 43 of 50 Listing Image for 8040 Hana Hwy 44 of 50 Listing Image for 8040 Hana Hwy 45 of 50 Listing Image for 8040 Hana Hwy 46 of 50 Listing Image for 8040 Hana Hwy 47 of 50 Listing Image for 8040 Hana Hwy 48 of 50 Listing Image for 8040 Hana Hwy 49 of 50 Listing Image for 8040 Hana Hwy 50 of 50

$1,295,000

Huelo

8040 Hana Hwy, Haiku

2 Beds 2.5 Baths 1,680 SqFt Residential MLS® # 408655 Date Sold: March 31, 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.