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 3586 Kalua Pl 1 of 12 Listing Image for 3586 Kalua Pl 2 of 12 Listing Image for 3586 Kalua Pl 3 of 12 Listing Image for 3586 Kalua Pl 4 of 12 Listing Image for 3586 Kalua Pl 5 of 12 Listing Image for 3586 Kalua Pl 6 of 12 Listing Image for 3586 Kalua Pl 7 of 12 Listing Image for 3586 Kalua Pl 8 of 12 Listing Image for 3586 Kalua Pl 9 of 12 Listing Image for 3586 Kalua Pl 10 of 12 Listing Image for 3586 Kalua Pl 11 of 12 Listing Image for 3586 Kalua Pl 12 of 12

$1,125,000

↓ $25,000

Makawao

3586 Kalua Pl, Makawao/Olinda/Haliimaile

3 Beds 2 Baths 1,652 SqFt Residential MLS® # 408939

Days on Market: 195

Nathalie Mullinix Rlty Universal Inc

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$8,800,000

Kula/Ulupalakua/Kanaio

29 Kolonahe Pl A, Kula/Ulupalakua/Kanaio

3 Beds 3.5 Baths 3,766 SqFt Residential MLS® # 408938

Days on Market: 196

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

Listing Image for 2597 Moolio Pl 1 of 49 Listing Image for 2597 Moolio Pl 2 of 49 Listing Image for 2597 Moolio Pl 3 of 49 Listing Image for 2597 Moolio Pl 4 of 49 Listing Image for 2597 Moolio Pl 5 of 49 Listing Image for 2597 Moolio Pl 6 of 49 Listing Image for 2597 Moolio Pl 7 of 49 Listing Image for 2597 Moolio Pl 8 of 49 Listing Image for 2597 Moolio Pl 9 of 49 Listing Image for 2597 Moolio Pl 10 of 49 Listing Image for 2597 Moolio Pl 11 of 49 Listing Image for 2597 Moolio Pl 12 of 49 Listing Image for 2597 Moolio Pl 13 of 49 Listing Image for 2597 Moolio Pl 14 of 49 Listing Image for 2597 Moolio Pl 15 of 49 Listing Image for 2597 Moolio Pl 16 of 49 Listing Image for 2597 Moolio Pl 17 of 49 Listing Image for 2597 Moolio Pl 18 of 49 Listing Image for 2597 Moolio Pl 19 of 49 Listing Image for 2597 Moolio Pl 20 of 49 Listing Image for 2597 Moolio Pl 21 of 49 Listing Image for 2597 Moolio Pl 22 of 49 Listing Image for 2597 Moolio Pl 23 of 49 Listing Image for 2597 Moolio Pl 24 of 49 Listing Image for 2597 Moolio Pl 25 of 49 Listing Image for 2597 Moolio Pl 26 of 49 Listing Image for 2597 Moolio Pl 27 of 49 Listing Image for 2597 Moolio Pl 28 of 49 Listing Image for 2597 Moolio Pl 29 of 49 Listing Image for 2597 Moolio Pl 30 of 49 Listing Image for 2597 Moolio Pl 31 of 49 Listing Image for 2597 Moolio Pl 32 of 49 Listing Image for 2597 Moolio Pl 33 of 49 Listing Image for 2597 Moolio Pl 34 of 49 Listing Image for 2597 Moolio Pl 35 of 49 Listing Image for 2597 Moolio Pl 36 of 49 Listing Image for 2597 Moolio Pl 37 of 49 Listing Image for 2597 Moolio Pl 38 of 49 Listing Image for 2597 Moolio Pl 39 of 49 Listing Image for 2597 Moolio Pl 40 of 49 Listing Image for 2597 Moolio Pl 41 of 49 Listing Image for 2597 Moolio Pl 42 of 49 Listing Image for 2597 Moolio Pl 43 of 49 Listing Image for 2597 Moolio Pl 44 of 49 Listing Image for 2597 Moolio Pl 45 of 49 Listing Image for 2597 Moolio Pl 46 of 49 Listing Image for 2597 Moolio Pl 47 of 49 Listing Image for 2597 Moolio Pl 48 of 49 Listing Image for 2597 Moolio Pl 49 of 49

$1,800,000

↓ $50,000

Pacific Terrace

2597 Moolio Pl, Kihei

4 Beds 3 Baths 1,912 SqFt Residential MLS® # 408930

Days on Market: 197

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

Short Term Rental
Listing Image for 940 S Kihei Rd A307 1 of 23 Listing Image for 940 S Kihei Rd A307 2 of 23 Listing Image for 940 S Kihei Rd A307 3 of 23 Listing Image for 940 S Kihei Rd A307 4 of 23 Listing Image for 940 S Kihei Rd A307 5 of 23 Listing Image for 940 S Kihei Rd A307 6 of 23 Listing Image for 940 S Kihei Rd A307 7 of 23 Listing Image for 940 S Kihei Rd A307 8 of 23 Listing Image for 940 S Kihei Rd A307 9 of 23 Listing Image for 940 S Kihei Rd A307 10 of 23 Listing Image for 940 S Kihei Rd A307 11 of 23 Listing Image for 940 S Kihei Rd A307 12 of 23 Listing Image for 940 S Kihei Rd A307 13 of 23 Listing Image for 940 S Kihei Rd A307 14 of 23 Listing Image for 940 S Kihei Rd A307 15 of 23 Listing Image for 940 S Kihei Rd A307 16 of 23 Listing Image for 940 S Kihei Rd A307 17 of 23 Listing Image for 940 S Kihei Rd A307 18 of 23 Listing Image for 940 S Kihei Rd A307 19 of 23 Listing Image for 940 S Kihei Rd A307 20 of 23 Listing Image for 940 S Kihei Rd A307 21 of 23 Listing Image for 940 S Kihei Rd A307 22 of 23 Listing Image for 940 S Kihei Rd A307 23 of 23

$859,000

↓ $70,000

Luana Kai A307

940 S Kihei Rd A307, Kihei

2 Beds 2 Baths 963 SqFt Residential MLS® # 406949

Days on Market: 387

Coldwell Banker Island Prop(S) Cell: 808-250-9356

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

$2,349,000

↓ $100,000

Kaanapali Hillside

9 Puu Hale St, Kaanapali

3 Beds 3 Baths 2,928 SqFt Residential MLS® # 408922

Days on Market: 197

Keller Williams Realty Maui-L Cell: 808-250-5948

Listing Image for 299 Liholiho St 1 of 25 Listing Image for 299 Liholiho St 2 of 25 Listing Image for 299 Liholiho St 3 of 25 Listing Image for 299 Liholiho St 4 of 25 Listing Image for 299 Liholiho St 5 of 25 Listing Image for 299 Liholiho St 6 of 25 Listing Image for 299 Liholiho St 7 of 25 Listing Image for 299 Liholiho St 8 of 25 Listing Image for 299 Liholiho St 9 of 25 Listing Image for 299 Liholiho St 10 of 25 Listing Image for 299 Liholiho St 11 of 25 Listing Image for 299 Liholiho St 12 of 25 Listing Image for 299 Liholiho St 13 of 25 Listing Image for 299 Liholiho St 14 of 25 Listing Image for 299 Liholiho St 15 of 25 Listing Image for 299 Liholiho St 16 of 25 Listing Image for 299 Liholiho St 17 of 25 Listing Image for 299 Liholiho St 18 of 25 Listing Image for 299 Liholiho St 19 of 25 Listing Image for 299 Liholiho St 20 of 25 Listing Image for 299 Liholiho St 21 of 25 Listing Image for 299 Liholiho St 22 of 25 Listing Image for 299 Liholiho St 23 of 25 Listing Image for 299 Liholiho St 24 of 25 Listing Image for 299 Liholiho St 25 of 25

$1,225,000

↓ $25,000

Wailuku

299 Liholiho St, Wailuku

3 Beds 2 Baths 1,727 SqFt Residential MLS® # 408913

Days on Market: 201

Coldwell Banker Island Prop(S) Cell: 808-425-3566

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

$2,995,000

↓ $105,000

Alaeloa 9

20 Hui Rd I 9, Napili/Kahana/Honokowai

4 Beds 4 Baths 4,000 SqFt Residential MLS® # 408904

Days on Market: 198

Coldwell Banker Island Prop(S) Cell: 808-344-4363

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: 12/01/2025
Listing Image for 760 S Kihei Rd 522 1 of 48 Listing Image for 760 S Kihei Rd 522 2 of 48 Listing Image for 760 S Kihei Rd 522 3 of 48 Listing Image for 760 S Kihei Rd 522 4 of 48 Listing Image for 760 S Kihei Rd 522 5 of 48 Listing Image for 760 S Kihei Rd 522 6 of 48 Listing Image for 760 S Kihei Rd 522 7 of 48 Listing Image for 760 S Kihei Rd 522 8 of 48 Listing Image for 760 S Kihei Rd 522 9 of 48 Listing Image for 760 S Kihei Rd 522 10 of 48 Listing Image for 760 S Kihei Rd 522 11 of 48 Listing Image for 760 S Kihei Rd 522 12 of 48 Listing Image for 760 S Kihei Rd 522 13 of 48 Listing Image for 760 S Kihei Rd 522 14 of 48 Listing Image for 760 S Kihei Rd 522 15 of 48 Listing Image for 760 S Kihei Rd 522 16 of 48 Listing Image for 760 S Kihei Rd 522 17 of 48 Listing Image for 760 S Kihei Rd 522 18 of 48 Listing Image for 760 S Kihei Rd 522 19 of 48 Listing Image for 760 S Kihei Rd 522 20 of 48 Listing Image for 760 S Kihei Rd 522 21 of 48 Listing Image for 760 S Kihei Rd 522 22 of 48 Listing Image for 760 S Kihei Rd 522 23 of 48 Listing Image for 760 S Kihei Rd 522 24 of 48 Listing Image for 760 S Kihei Rd 522 25 of 48 Listing Image for 760 S Kihei Rd 522 26 of 48 Listing Image for 760 S Kihei Rd 522 27 of 48 Listing Image for 760 S Kihei Rd 522 28 of 48 Listing Image for 760 S Kihei Rd 522 29 of 48 Listing Image for 760 S Kihei Rd 522 30 of 48 Listing Image for 760 S Kihei Rd 522 31 of 48 Listing Image for 760 S Kihei Rd 522 32 of 48 Listing Image for 760 S Kihei Rd 522 33 of 48 Listing Image for 760 S Kihei Rd 522 34 of 48 Listing Image for 760 S Kihei Rd 522 35 of 48 Listing Image for 760 S Kihei Rd 522 36 of 48 Listing Image for 760 S Kihei Rd 522 37 of 48 Listing Image for 760 S Kihei Rd 522 38 of 48 Listing Image for 760 S Kihei Rd 522 39 of 48 Listing Image for 760 S Kihei Rd 522 40 of 48 Listing Image for 760 S Kihei Rd 522 41 of 48 Listing Image for 760 S Kihei Rd 522 42 of 48 Listing Image for 760 S Kihei Rd 522 43 of 48 Listing Image for 760 S Kihei Rd 522 44 of 48 Listing Image for 760 S Kihei Rd 522 45 of 48 Listing Image for 760 S Kihei Rd 522 46 of 48 Listing Image for 760 S Kihei Rd 522 47 of 48 Listing Image for 760 S Kihei Rd 522 48 of 48

$1,350,000

Menehune Shores 522

760 S Kihei Rd 522, Kihei

2 Beds 2 Baths 885 SqFt Residential MLS® # 407748 Date Sold: December 1, 2025
Sold
Closed: 02/04/2026
Listing Image for 302 Manini Pl 1 of 25 Listing Image for 302 Manini Pl 2 of 25 Listing Image for 302 Manini Pl 3 of 25 Listing Image for 302 Manini Pl 4 of 25 Listing Image for 302 Manini Pl 5 of 25 Listing Image for 302 Manini Pl 6 of 25 Listing Image for 302 Manini Pl 7 of 25 Listing Image for 302 Manini Pl 8 of 25 Listing Image for 302 Manini Pl 9 of 25 Listing Image for 302 Manini Pl 10 of 25 Listing Image for 302 Manini Pl 11 of 25 Listing Image for 302 Manini Pl 12 of 25 Listing Image for 302 Manini Pl 13 of 25 Listing Image for 302 Manini Pl 14 of 25 Listing Image for 302 Manini Pl 15 of 25 Listing Image for 302 Manini Pl 16 of 25 Listing Image for 302 Manini Pl 17 of 25 Listing Image for 302 Manini Pl 18 of 25 Listing Image for 302 Manini Pl 19 of 25 Listing Image for 302 Manini Pl 20 of 25 Listing Image for 302 Manini Pl 21 of 25 Listing Image for 302 Manini Pl 22 of 25 Listing Image for 302 Manini Pl 23 of 25 Listing Image for 302 Manini Pl 24 of 25 Listing Image for 302 Manini Pl 25 of 25

$985,000

Kihei Heights

302 Manini Pl, Kihei

6 Beds 2 Baths 1,700 SqFt Residential MLS® # 407746 Date Sold: February 4, 2026
Sold
Closed: 06/12/2026
Listing Image for 110 Kaanapali Shores Pl 311 1 of 37 Listing Image for 110 Kaanapali Shores Pl 311 2 of 37 Listing Image for 110 Kaanapali Shores Pl 311 3 of 37 Listing Image for 110 Kaanapali Shores Pl 311 4 of 37 Listing Image for 110 Kaanapali Shores Pl 311 5 of 37 Listing Image for 110 Kaanapali Shores Pl 311 6 of 37 Listing Image for 110 Kaanapali Shores Pl 311 7 of 37 Listing Image for 110 Kaanapali Shores Pl 311 8 of 37 Listing Image for 110 Kaanapali Shores Pl 311 9 of 37 Listing Image for 110 Kaanapali Shores Pl 311 10 of 37 Listing Image for 110 Kaanapali Shores Pl 311 11 of 37 Listing Image for 110 Kaanapali Shores Pl 311 12 of 37 Listing Image for 110 Kaanapali Shores Pl 311 13 of 37 Listing Image for 110 Kaanapali Shores Pl 311 14 of 37 Listing Image for 110 Kaanapali Shores Pl 311 15 of 37 Listing Image for 110 Kaanapali Shores Pl 311 16 of 37 Listing Image for 110 Kaanapali Shores Pl 311 17 of 37 Listing Image for 110 Kaanapali Shores Pl 311 18 of 37 Listing Image for 110 Kaanapali Shores Pl 311 19 of 37 Listing Image for 110 Kaanapali Shores Pl 311 20 of 37 Listing Image for 110 Kaanapali Shores Pl 311 21 of 37 Listing Image for 110 Kaanapali Shores Pl 311 22 of 37 Listing Image for 110 Kaanapali Shores Pl 311 23 of 37 Listing Image for 110 Kaanapali Shores Pl 311 24 of 37 Listing Image for 110 Kaanapali Shores Pl 311 25 of 37 Listing Image for 110 Kaanapali Shores Pl 311 26 of 37 Listing Image for 110 Kaanapali Shores Pl 311 27 of 37 Listing Image for 110 Kaanapali Shores Pl 311 28 of 37 Listing Image for 110 Kaanapali Shores Pl 311 29 of 37 Listing Image for 110 Kaanapali Shores Pl 311 30 of 37 Listing Image for 110 Kaanapali Shores Pl 311 31 of 37 Listing Image for 110 Kaanapali Shores Pl 311 32 of 37 Listing Image for 110 Kaanapali Shores Pl 311 33 of 37 Listing Image for 110 Kaanapali Shores Pl 311 34 of 37 Listing Image for 110 Kaanapali Shores Pl 311 35 of 37 Listing Image for 110 Kaanapali Shores Pl 311 36 of 37 Listing Image for 110 Kaanapali Shores Pl 311 37 of 37

$1,560,000

↓ $390,000

Mahana 311

110 Kaanapali Shores Pl 311, Kaanapali

2 Beds 2 Baths 1,178 SqFt Residential MLS® # 407745 Date Sold: June 12, 2026
Sold
Closed: 12/30/2025
Listing Image for 147 Hoohale St 1 of 50 Listing Image for 147 Hoohale St 2 of 50 Listing Image for 147 Hoohale St 3 of 50 Listing Image for 147 Hoohale St 4 of 50 Listing Image for 147 Hoohale St 5 of 50 Listing Image for 147 Hoohale St 6 of 50 Listing Image for 147 Hoohale St 7 of 50 Listing Image for 147 Hoohale St 8 of 50 Listing Image for 147 Hoohale St 9 of 50 Listing Image for 147 Hoohale St 10 of 50 Listing Image for 147 Hoohale St 11 of 50 Listing Image for 147 Hoohale St 12 of 50 Listing Image for 147 Hoohale St 13 of 50 Listing Image for 147 Hoohale St 14 of 50 Listing Image for 147 Hoohale St 15 of 50 Listing Image for 147 Hoohale St 16 of 50 Listing Image for 147 Hoohale St 17 of 50 Listing Image for 147 Hoohale St 18 of 50 Listing Image for 147 Hoohale St 19 of 50 Listing Image for 147 Hoohale St 20 of 50 Listing Image for 147 Hoohale St 21 of 50 Listing Image for 147 Hoohale St 22 of 50 Listing Image for 147 Hoohale St 23 of 50 Listing Image for 147 Hoohale St 24 of 50 Listing Image for 147 Hoohale St 25 of 50 Listing Image for 147 Hoohale St 26 of 50 Listing Image for 147 Hoohale St 27 of 50 Listing Image for 147 Hoohale St 28 of 50 Listing Image for 147 Hoohale St 29 of 50 Listing Image for 147 Hoohale St 30 of 50 Listing Image for 147 Hoohale St 31 of 50 Listing Image for 147 Hoohale St 32 of 50 Listing Image for 147 Hoohale St 33 of 50 Listing Image for 147 Hoohale St 34 of 50 Listing Image for 147 Hoohale St 35 of 50 Listing Image for 147 Hoohale St 36 of 50 Listing Image for 147 Hoohale St 37 of 50 Listing Image for 147 Hoohale St 38 of 50 Listing Image for 147 Hoohale St 39 of 50 Listing Image for 147 Hoohale St 40 of 50 Listing Image for 147 Hoohale St 41 of 50 Listing Image for 147 Hoohale St 42 of 50 Listing Image for 147 Hoohale St 43 of 50 Listing Image for 147 Hoohale St 44 of 50 Listing Image for 147 Hoohale St 45 of 50 Listing Image for 147 Hoohale St 46 of 50 Listing Image for 147 Hoohale St 47 of 50 Listing Image for 147 Hoohale St 48 of 50 Listing Image for 147 Hoohale St 49 of 50 Listing Image for 147 Hoohale St 50 of 50

$1,750,000

Kilohana Ridge

147 Hoohale St, Kihei

4 Beds 3 Baths 2,447 SqFt Residential MLS® # 407742 Date Sold: December 30, 2025
Sold
Closed: 03/04/2026
Listing Image for 1669 Hoonanea St 1 of 50 Listing Image for 1669 Hoonanea St 2 of 50 Listing Image for 1669 Hoonanea St 3 of 50 Listing Image for 1669 Hoonanea St 4 of 50 Listing Image for 1669 Hoonanea St 5 of 50 Listing Image for 1669 Hoonanea St 6 of 50 Listing Image for 1669 Hoonanea St 7 of 50 Listing Image for 1669 Hoonanea St 8 of 50 Listing Image for 1669 Hoonanea St 9 of 50 Listing Image for 1669 Hoonanea St 10 of 50 Listing Image for 1669 Hoonanea St 11 of 50 Listing Image for 1669 Hoonanea St 12 of 50 Listing Image for 1669 Hoonanea St 13 of 50 Listing Image for 1669 Hoonanea St 14 of 50 Listing Image for 1669 Hoonanea St 15 of 50 Listing Image for 1669 Hoonanea St 16 of 50 Listing Image for 1669 Hoonanea St 17 of 50 Listing Image for 1669 Hoonanea St 18 of 50 Listing Image for 1669 Hoonanea St 19 of 50 Listing Image for 1669 Hoonanea St 20 of 50 Listing Image for 1669 Hoonanea St 21 of 50 Listing Image for 1669 Hoonanea St 22 of 50 Listing Image for 1669 Hoonanea St 23 of 50 Listing Image for 1669 Hoonanea St 24 of 50 Listing Image for 1669 Hoonanea St 25 of 50 Listing Image for 1669 Hoonanea St 26 of 50 Listing Image for 1669 Hoonanea St 27 of 50 Listing Image for 1669 Hoonanea St 28 of 50 Listing Image for 1669 Hoonanea St 29 of 50 Listing Image for 1669 Hoonanea St 30 of 50 Listing Image for 1669 Hoonanea St 31 of 50 Listing Image for 1669 Hoonanea St 32 of 50 Listing Image for 1669 Hoonanea St 33 of 50 Listing Image for 1669 Hoonanea St 34 of 50 Listing Image for 1669 Hoonanea St 35 of 50 Listing Image for 1669 Hoonanea St 36 of 50 Listing Image for 1669 Hoonanea St 37 of 50 Listing Image for 1669 Hoonanea St 38 of 50 Listing Image for 1669 Hoonanea St 39 of 50 Listing Image for 1669 Hoonanea St 40 of 50 Listing Image for 1669 Hoonanea St 41 of 50 Listing Image for 1669 Hoonanea St 42 of 50 Listing Image for 1669 Hoonanea St 43 of 50 Listing Image for 1669 Hoonanea St 44 of 50 Listing Image for 1669 Hoonanea St 45 of 50 Listing Image for 1669 Hoonanea St 46 of 50 Listing Image for 1669 Hoonanea St 47 of 50 Listing Image for 1669 Hoonanea St 48 of 50 Listing Image for 1669 Hoonanea St 49 of 50 Listing Image for 1669 Hoonanea St 50 of 50

$760,000

Kihei

1669 Hoonanea St, Kihei

3 Beds 2 Baths 1,700 SqFt Residential MLS® # 407739 Date Sold: March 4, 2026
Sold
Closed: 02/13/2026
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$1,150,000

↓ $250,000

Wailea Ekahi 25B

3300 Wailea Alanui Dr 25b, Wailea/Makena

2 Beds 2.5 Baths 1,133 SqFt Residential MLS® # 407738 Date Sold: February 13, 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.

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