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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Short Term Rental
Listing Image for 100 Ridge Rd 1614 1 of 50 Listing Image for 100 Ridge Rd 1614 2 of 50 Listing Image for 100 Ridge Rd 1614 3 of 50 Listing Image for 100 Ridge Rd 1614 4 of 50 Listing Image for 100 Ridge Rd 1614 5 of 50 Listing Image for 100 Ridge Rd 1614 6 of 50 Listing Image for 100 Ridge Rd 1614 7 of 50 Listing Image for 100 Ridge Rd 1614 8 of 50 Listing Image for 100 Ridge Rd 1614 9 of 50 Listing Image for 100 Ridge Rd 1614 10 of 50 Listing Image for 100 Ridge Rd 1614 11 of 50 Listing Image for 100 Ridge Rd 1614 12 of 50 Listing Image for 100 Ridge Rd 1614 13 of 50 Listing Image for 100 Ridge Rd 1614 14 of 50 Listing Image for 100 Ridge Rd 1614 15 of 50 Listing Image for 100 Ridge Rd 1614 16 of 50 Listing Image for 100 Ridge Rd 1614 17 of 50 Listing Image for 100 Ridge Rd 1614 18 of 50 Listing Image for 100 Ridge Rd 1614 19 of 50 Listing Image for 100 Ridge Rd 1614 20 of 50 Listing Image for 100 Ridge Rd 1614 21 of 50 Listing Image for 100 Ridge Rd 1614 22 of 50 Listing Image for 100 Ridge Rd 1614 23 of 50 Listing Image for 100 Ridge Rd 1614 24 of 50 Listing Image for 100 Ridge Rd 1614 25 of 50 Listing Image for 100 Ridge Rd 1614 26 of 50 Listing Image for 100 Ridge Rd 1614 27 of 50 Listing Image for 100 Ridge Rd 1614 28 of 50 Listing Image for 100 Ridge Rd 1614 29 of 50 Listing Image for 100 Ridge Rd 1614 30 of 50 Listing Image for 100 Ridge Rd 1614 31 of 50 Listing Image for 100 Ridge Rd 1614 32 of 50 Listing Image for 100 Ridge Rd 1614 33 of 50 Listing Image for 100 Ridge Rd 1614 34 of 50 Listing Image for 100 Ridge Rd 1614 35 of 50 Listing Image for 100 Ridge Rd 1614 36 of 50 Listing Image for 100 Ridge Rd 1614 37 of 50 Listing Image for 100 Ridge Rd 1614 38 of 50 Listing Image for 100 Ridge Rd 1614 39 of 50 Listing Image for 100 Ridge Rd 1614 40 of 50 Listing Image for 100 Ridge Rd 1614 41 of 50 Listing Image for 100 Ridge Rd 1614 42 of 50 Listing Image for 100 Ridge Rd 1614 43 of 50 Listing Image for 100 Ridge Rd 1614 44 of 50 Listing Image for 100 Ridge Rd 1614 45 of 50 Listing Image for 100 Ridge Rd 1614 46 of 50 Listing Image for 100 Ridge Rd 1614 47 of 50 Listing Image for 100 Ridge Rd 1614 48 of 50 Listing Image for 100 Ridge Rd 1614 49 of 50 Listing Image for 100 Ridge Rd 1614 50 of 50

$1,219,000

↓ $31,000

Kapalua Ridge 1614

100 Ridge Rd 1614, Kapalua

1 Bed 2 Baths 1,125 SqFt Residential MLS® # 407924

Days on Market: 292

Ridge Realty Rentals LLC

Short Term Rental
Listing Image for 2481 Kaanapali Pkwy 456 1 of 31 Listing Image for 2481 Kaanapali Pkwy 456 2 of 31 Listing Image for 2481 Kaanapali Pkwy 456 3 of 31 Listing Image for 2481 Kaanapali Pkwy 456 4 of 31 Listing Image for 2481 Kaanapali Pkwy 456 5 of 31 Listing Image for 2481 Kaanapali Pkwy 456 6 of 31 Listing Image for 2481 Kaanapali Pkwy 456 7 of 31 Listing Image for 2481 Kaanapali Pkwy 456 8 of 31 Listing Image for 2481 Kaanapali Pkwy 456 9 of 31 Listing Image for 2481 Kaanapali Pkwy 456 10 of 31 Listing Image for 2481 Kaanapali Pkwy 456 11 of 31 Listing Image for 2481 Kaanapali Pkwy 456 12 of 31 Listing Image for 2481 Kaanapali Pkwy 456 13 of 31 Listing Image for 2481 Kaanapali Pkwy 456 14 of 31 Listing Image for 2481 Kaanapali Pkwy 456 15 of 31 Listing Image for 2481 Kaanapali Pkwy 456 16 of 31 Listing Image for 2481 Kaanapali Pkwy 456 17 of 31 Listing Image for 2481 Kaanapali Pkwy 456 18 of 31 Listing Image for 2481 Kaanapali Pkwy 456 19 of 31 Listing Image for 2481 Kaanapali Pkwy 456 20 of 31 Listing Image for 2481 Kaanapali Pkwy 456 21 of 31 Listing Image for 2481 Kaanapali Pkwy 456 22 of 31 Listing Image for 2481 Kaanapali Pkwy 456 23 of 31 Listing Image for 2481 Kaanapali Pkwy 456 24 of 31 Listing Image for 2481 Kaanapali Pkwy 456 25 of 31 Listing Image for 2481 Kaanapali Pkwy 456 26 of 31 Listing Image for 2481 Kaanapali Pkwy 456 27 of 31 Listing Image for 2481 Kaanapali Pkwy 456 28 of 31 Listing Image for 2481 Kaanapali Pkwy 456 29 of 31 Listing Image for 2481 Kaanapali Pkwy 456 30 of 31 Listing Image for 2481 Kaanapali Pkwy 456 31 of 31

$2,295,000

↓ $400,000

Whaler 456

2481 Kaanapali Pkwy 456, Kaanapali

1 Bed 1 Bath 901 SqFt Residential MLS® # 407888

Days on Market: 296

Berkshire Hathaway Maui Prop-L Cell: 808-280-7061

Short Term Rental
Listing Image for 4850 Makena Alanui Rd C106 1 of 49 Listing Image for 4850 Makena Alanui Rd C106 2 of 49 Listing Image for 4850 Makena Alanui Rd C106 3 of 49 Listing Image for 4850 Makena Alanui Rd C106 4 of 49 Listing Image for 4850 Makena Alanui Rd C106 5 of 49 Listing Image for 4850 Makena Alanui Rd C106 6 of 49 Listing Image for 4850 Makena Alanui Rd C106 7 of 49 Listing Image for 4850 Makena Alanui Rd C106 8 of 49 Listing Image for 4850 Makena Alanui Rd C106 9 of 49 Listing Image for 4850 Makena Alanui Rd C106 10 of 49 Listing Image for 4850 Makena Alanui Rd C106 11 of 49 Listing Image for 4850 Makena Alanui Rd C106 12 of 49 Listing Image for 4850 Makena Alanui Rd C106 13 of 49 Listing Image for 4850 Makena Alanui Rd C106 14 of 49 Listing Image for 4850 Makena Alanui Rd C106 15 of 49 Listing Image for 4850 Makena Alanui Rd C106 16 of 49 Listing Image for 4850 Makena Alanui Rd C106 17 of 49 Listing Image for 4850 Makena Alanui Rd C106 18 of 49 Listing Image for 4850 Makena Alanui Rd C106 19 of 49 Listing Image for 4850 Makena Alanui Rd C106 20 of 49 Listing Image for 4850 Makena Alanui Rd C106 21 of 49 Listing Image for 4850 Makena Alanui Rd C106 22 of 49 Listing Image for 4850 Makena Alanui Rd C106 23 of 49 Listing Image for 4850 Makena Alanui Rd C106 24 of 49 Listing Image for 4850 Makena Alanui Rd C106 25 of 49 Listing Image for 4850 Makena Alanui Rd C106 26 of 49 Listing Image for 4850 Makena Alanui Rd C106 27 of 49 Listing Image for 4850 Makena Alanui Rd C106 28 of 49 Listing Image for 4850 Makena Alanui Rd C106 29 of 49 Listing Image for 4850 Makena Alanui Rd C106 30 of 49 Listing Image for 4850 Makena Alanui Rd C106 31 of 49 Listing Image for 4850 Makena Alanui Rd C106 32 of 49 Listing Image for 4850 Makena Alanui Rd C106 33 of 49 Listing Image for 4850 Makena Alanui Rd C106 34 of 49 Listing Image for 4850 Makena Alanui Rd C106 35 of 49 Listing Image for 4850 Makena Alanui Rd C106 36 of 49 Listing Image for 4850 Makena Alanui Rd C106 37 of 49 Listing Image for 4850 Makena Alanui Rd C106 38 of 49 Listing Image for 4850 Makena Alanui Rd C106 39 of 49 Listing Image for 4850 Makena Alanui Rd C106 40 of 49 Listing Image for 4850 Makena Alanui Rd C106 41 of 49 Listing Image for 4850 Makena Alanui Rd C106 42 of 49 Listing Image for 4850 Makena Alanui Rd C106 43 of 49 Listing Image for 4850 Makena Alanui Rd C106 44 of 49 Listing Image for 4850 Makena Alanui Rd C106 45 of 49 Listing Image for 4850 Makena Alanui Rd C106 46 of 49 Listing Image for 4850 Makena Alanui Rd C106 47 of 49 Listing Image for 4850 Makena Alanui Rd C106 48 of 49 Listing Image for 4850 Makena Alanui Rd C106 49 of 49

$3,950,000

↓ $200,000

Makena Surf C106

4850 Makena Alanui Rd C106, Wailea/Makena

2 Beds 2 Baths 1,600 SqFt Residential MLS® # 407882

Days on Market: 296

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

Short Term Rental
Listing Image for 940 S Kihei Rd B-301 1 of 48 Listing Image for 940 S Kihei Rd B-301 2 of 48 Listing Image for 940 S Kihei Rd B-301 3 of 48 Listing Image for 940 S Kihei Rd B-301 4 of 48 Listing Image for 940 S Kihei Rd B-301 5 of 48 Listing Image for 940 S Kihei Rd B-301 6 of 48 Listing Image for 940 S Kihei Rd B-301 7 of 48 Listing Image for 940 S Kihei Rd B-301 8 of 48 Listing Image for 940 S Kihei Rd B-301 9 of 48 Listing Image for 940 S Kihei Rd B-301 10 of 48 Listing Image for 940 S Kihei Rd B-301 11 of 48 Listing Image for 940 S Kihei Rd B-301 12 of 48 Listing Image for 940 S Kihei Rd B-301 13 of 48 Listing Image for 940 S Kihei Rd B-301 14 of 48 Listing Image for 940 S Kihei Rd B-301 15 of 48 Listing Image for 940 S Kihei Rd B-301 16 of 48 Listing Image for 940 S Kihei Rd B-301 17 of 48 Listing Image for 940 S Kihei Rd B-301 18 of 48 Listing Image for 940 S Kihei Rd B-301 19 of 48 Listing Image for 940 S Kihei Rd B-301 20 of 48 Listing Image for 940 S Kihei Rd B-301 21 of 48 Listing Image for 940 S Kihei Rd B-301 22 of 48 Listing Image for 940 S Kihei Rd B-301 23 of 48 Listing Image for 940 S Kihei Rd B-301 24 of 48 Listing Image for 940 S Kihei Rd B-301 25 of 48 Listing Image for 940 S Kihei Rd B-301 26 of 48 Listing Image for 940 S Kihei Rd B-301 27 of 48 Listing Image for 940 S Kihei Rd B-301 28 of 48 Listing Image for 940 S Kihei Rd B-301 29 of 48 Listing Image for 940 S Kihei Rd B-301 30 of 48 Listing Image for 940 S Kihei Rd B-301 31 of 48 Listing Image for 940 S Kihei Rd B-301 32 of 48 Listing Image for 940 S Kihei Rd B-301 33 of 48 Listing Image for 940 S Kihei Rd B-301 34 of 48 Listing Image for 940 S Kihei Rd B-301 35 of 48 Listing Image for 940 S Kihei Rd B-301 36 of 48 Listing Image for 940 S Kihei Rd B-301 37 of 48 Listing Image for 940 S Kihei Rd B-301 38 of 48 Listing Image for 940 S Kihei Rd B-301 39 of 48 Listing Image for 940 S Kihei Rd B-301 40 of 48 Listing Image for 940 S Kihei Rd B-301 41 of 48 Listing Image for 940 S Kihei Rd B-301 42 of 48 Listing Image for 940 S Kihei Rd B-301 43 of 48 Listing Image for 940 S Kihei Rd B-301 44 of 48 Listing Image for 940 S Kihei Rd B-301 45 of 48 Listing Image for 940 S Kihei Rd B-301 46 of 48 Listing Image for 940 S Kihei Rd B-301 47 of 48 Listing Image for 940 S Kihei Rd B-301 48 of 48

$1,445,000

↓ $130,000

Luana Kai B-301

940 S Kihei Rd B-301, Kihei

3 Beds 3 Baths 1,268 SqFt Residential MLS® # 407860

Days on Market: 299

Maui Luxury Real Estate LLC

Short Term Rental
Listing Image for 3800 Wailea Alanui Blvd Ph-209 1 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 2 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 3 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 4 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 5 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 6 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 7 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 8 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 9 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 10 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 11 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 12 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 13 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 14 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 15 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 16 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 17 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 18 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 19 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 20 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 21 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 22 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 23 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 24 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 25 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 26 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 27 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 28 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 29 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 30 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 31 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 32 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 33 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 34 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 35 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 36 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 37 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 38 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 39 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 40 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 41 of 42 Listing Image for 3800 Wailea Alanui Blvd Ph-209 42 of 42

$5,750,000

Wailea Beach Villas PH-209

3800 Wailea Alanui Blvd Ph-209, Wailea/Makena

3 Beds 3 Baths 2,521 SqFt Residential MLS® # 407859

Days on Market: 298

Keller Williams Realty Maui-Ka Cell: 808-264-6836

Short Term Rental
Listing Image for 500 Kapalua Dr 16p5-6 1 of 48 Listing Image for 500 Kapalua Dr 16p5-6 2 of 48 Listing Image for 500 Kapalua Dr 16p5-6 3 of 48 Listing Image for 500 Kapalua Dr 16p5-6 4 of 48 Listing Image for 500 Kapalua Dr 16p5-6 5 of 48 Listing Image for 500 Kapalua Dr 16p5-6 6 of 48 Listing Image for 500 Kapalua Dr 16p5-6 7 of 48 Listing Image for 500 Kapalua Dr 16p5-6 8 of 48 Listing Image for 500 Kapalua Dr 16p5-6 9 of 48 Listing Image for 500 Kapalua Dr 16p5-6 10 of 48 Listing Image for 500 Kapalua Dr 16p5-6 11 of 48 Listing Image for 500 Kapalua Dr 16p5-6 12 of 48 Listing Image for 500 Kapalua Dr 16p5-6 13 of 48 Listing Image for 500 Kapalua Dr 16p5-6 14 of 48 Listing Image for 500 Kapalua Dr 16p5-6 15 of 48 Listing Image for 500 Kapalua Dr 16p5-6 16 of 48 Listing Image for 500 Kapalua Dr 16p5-6 17 of 48 Listing Image for 500 Kapalua Dr 16p5-6 18 of 48 Listing Image for 500 Kapalua Dr 16p5-6 19 of 48 Listing Image for 500 Kapalua Dr 16p5-6 20 of 48 Listing Image for 500 Kapalua Dr 16p5-6 21 of 48 Listing Image for 500 Kapalua Dr 16p5-6 22 of 48 Listing Image for 500 Kapalua Dr 16p5-6 23 of 48 Listing Image for 500 Kapalua Dr 16p5-6 24 of 48 Listing Image for 500 Kapalua Dr 16p5-6 25 of 48 Listing Image for 500 Kapalua Dr 16p5-6 26 of 48 Listing Image for 500 Kapalua Dr 16p5-6 27 of 48 Listing Image for 500 Kapalua Dr 16p5-6 28 of 48 Listing Image for 500 Kapalua Dr 16p5-6 29 of 48 Listing Image for 500 Kapalua Dr 16p5-6 30 of 48 Listing Image for 500 Kapalua Dr 16p5-6 31 of 48 Listing Image for 500 Kapalua Dr 16p5-6 32 of 48 Listing Image for 500 Kapalua Dr 16p5-6 33 of 48 Listing Image for 500 Kapalua Dr 16p5-6 34 of 48 Listing Image for 500 Kapalua Dr 16p5-6 35 of 48 Listing Image for 500 Kapalua Dr 16p5-6 36 of 48 Listing Image for 500 Kapalua Dr 16p5-6 37 of 48 Listing Image for 500 Kapalua Dr 16p5-6 38 of 48 Listing Image for 500 Kapalua Dr 16p5-6 39 of 48 Listing Image for 500 Kapalua Dr 16p5-6 40 of 48 Listing Image for 500 Kapalua Dr 16p5-6 41 of 48 Listing Image for 500 Kapalua Dr 16p5-6 42 of 48 Listing Image for 500 Kapalua Dr 16p5-6 43 of 48 Listing Image for 500 Kapalua Dr 16p5-6 44 of 48 Listing Image for 500 Kapalua Dr 16p5-6 45 of 48 Listing Image for 500 Kapalua Dr 16p5-6 46 of 48 Listing Image for 500 Kapalua Dr 16p5-6 47 of 48 Listing Image for 500 Kapalua Dr 16p5-6 48 of 48

$1,290,000

↓ $130,000

Kapalua Golf Villas 16P5-6

500 Kapalua Dr 16p5-6, Kapalua

2 Beds 2 Baths 1,344 SqFt Residential MLS® # 407846

Days on Market: 299

eXp Realty Cell: 808-222-0478

Listing Image for 325 Hokiokio Pl 1 of 31 Listing Image for 325 Hokiokio Pl 2 of 31 Listing Image for 325 Hokiokio Pl 3 of 31 Listing Image for 325 Hokiokio Pl 4 of 31 Listing Image for 325 Hokiokio Pl 5 of 31 Listing Image for 325 Hokiokio Pl 6 of 31 Listing Image for 325 Hokiokio Pl 7 of 31 Listing Image for 325 Hokiokio Pl 8 of 31 Listing Image for 325 Hokiokio Pl 9 of 31 Listing Image for 325 Hokiokio Pl 10 of 31 Listing Image for 325 Hokiokio Pl 11 of 31 Listing Image for 325 Hokiokio Pl 12 of 31 Listing Image for 325 Hokiokio Pl 13 of 31 Listing Image for 325 Hokiokio Pl 14 of 31 Listing Image for 325 Hokiokio Pl 15 of 31 Listing Image for 325 Hokiokio Pl 16 of 31 Listing Image for 325 Hokiokio Pl 17 of 31 Listing Image for 325 Hokiokio Pl 18 of 31 Listing Image for 325 Hokiokio Pl 19 of 31 Listing Image for 325 Hokiokio Pl 20 of 31 Listing Image for 325 Hokiokio Pl 21 of 31 Listing Image for 325 Hokiokio Pl 22 of 31 Listing Image for 325 Hokiokio Pl 23 of 31 Listing Image for 325 Hokiokio Pl 24 of 31 Listing Image for 325 Hokiokio Pl 25 of 31 Listing Image for 325 Hokiokio Pl 26 of 31 Listing Image for 325 Hokiokio Pl 27 of 31 Listing Image for 325 Hokiokio Pl 28 of 31 Listing Image for 325 Hokiokio Pl 29 of 31 Listing Image for 325 Hokiokio Pl 30 of 31 Listing Image for 325 Hokiokio Pl 31 of 31

$10,950,000

Puunoa Estates

325 Hokiokio Pl, Lahaina

5 Beds 5.5 Baths 4,938 SqFt Residential MLS® # 407837

Days on Market: 300

Coldwell Banker Island Prop-KP Cell: 808-250-1583

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: 08/31/2026
Listing Image for 2936 S Kihei Rd 613 1 of 47 Listing Image for 2936 S Kihei Rd 613 2 of 47 Listing Image for 2936 S Kihei Rd 613 3 of 47 Listing Image for 2936 S Kihei Rd 613 4 of 47 Listing Image for 2936 S Kihei Rd 613 5 of 47 Listing Image for 2936 S Kihei Rd 613 6 of 47 Listing Image for 2936 S Kihei Rd 613 7 of 47 Listing Image for 2936 S Kihei Rd 613 8 of 47 Listing Image for 2936 S Kihei Rd 613 9 of 47 Listing Image for 2936 S Kihei Rd 613 10 of 47 Listing Image for 2936 S Kihei Rd 613 11 of 47 Listing Image for 2936 S Kihei Rd 613 12 of 47 Listing Image for 2936 S Kihei Rd 613 13 of 47 Listing Image for 2936 S Kihei Rd 613 14 of 47 Listing Image for 2936 S Kihei Rd 613 15 of 47 Listing Image for 2936 S Kihei Rd 613 16 of 47 Listing Image for 2936 S Kihei Rd 613 17 of 47 Listing Image for 2936 S Kihei Rd 613 18 of 47 Listing Image for 2936 S Kihei Rd 613 19 of 47 Listing Image for 2936 S Kihei Rd 613 20 of 47 Listing Image for 2936 S Kihei Rd 613 21 of 47 Listing Image for 2936 S Kihei Rd 613 22 of 47 Listing Image for 2936 S Kihei Rd 613 23 of 47 Listing Image for 2936 S Kihei Rd 613 24 of 47 Listing Image for 2936 S Kihei Rd 613 25 of 47 Listing Image for 2936 S Kihei Rd 613 26 of 47 Listing Image for 2936 S Kihei Rd 613 27 of 47 Listing Image for 2936 S Kihei Rd 613 28 of 47 Listing Image for 2936 S Kihei Rd 613 29 of 47 Listing Image for 2936 S Kihei Rd 613 30 of 47 Listing Image for 2936 S Kihei Rd 613 31 of 47 Listing Image for 2936 S Kihei Rd 613 32 of 47 Listing Image for 2936 S Kihei Rd 613 33 of 47 Listing Image for 2936 S Kihei Rd 613 34 of 47 Listing Image for 2936 S Kihei Rd 613 35 of 47 Listing Image for 2936 S Kihei Rd 613 36 of 47 Listing Image for 2936 S Kihei Rd 613 37 of 47 Listing Image for 2936 S Kihei Rd 613 38 of 47 Listing Image for 2936 S Kihei Rd 613 39 of 47 Listing Image for 2936 S Kihei Rd 613 40 of 47 Listing Image for 2936 S Kihei Rd 613 41 of 47 Listing Image for 2936 S Kihei Rd 613 42 of 47 Listing Image for 2936 S Kihei Rd 613 43 of 47 Listing Image for 2936 S Kihei Rd 613 44 of 47 Listing Image for 2936 S Kihei Rd 613 45 of 47 Listing Image for 2936 S Kihei Rd 613 46 of 47 Listing Image for 2936 S Kihei Rd 613 47 of 47

$815,000

↓ $184,000

Kihei Surfside 613

2936 S Kihei Rd 613, Kihei

1 Bed 1.5 Baths 680 SqFt Residential MLS® # 407260 Date Sold: August 31, 2026
Sold
Closed: 12/30/2025
Listing Image for 2481 Kaanapali Pkwy 413 1 of 30 Listing Image for 2481 Kaanapali Pkwy 413 2 of 30 Listing Image for 2481 Kaanapali Pkwy 413 3 of 30 Listing Image for 2481 Kaanapali Pkwy 413 4 of 30 Listing Image for 2481 Kaanapali Pkwy 413 5 of 30 Listing Image for 2481 Kaanapali Pkwy 413 6 of 30 Listing Image for 2481 Kaanapali Pkwy 413 7 of 30 Listing Image for 2481 Kaanapali Pkwy 413 8 of 30 Listing Image for 2481 Kaanapali Pkwy 413 9 of 30 Listing Image for 2481 Kaanapali Pkwy 413 10 of 30 Listing Image for 2481 Kaanapali Pkwy 413 11 of 30 Listing Image for 2481 Kaanapali Pkwy 413 12 of 30 Listing Image for 2481 Kaanapali Pkwy 413 13 of 30 Listing Image for 2481 Kaanapali Pkwy 413 14 of 30 Listing Image for 2481 Kaanapali Pkwy 413 15 of 30 Listing Image for 2481 Kaanapali Pkwy 413 16 of 30 Listing Image for 2481 Kaanapali Pkwy 413 17 of 30 Listing Image for 2481 Kaanapali Pkwy 413 18 of 30 Listing Image for 2481 Kaanapali Pkwy 413 19 of 30 Listing Image for 2481 Kaanapali Pkwy 413 20 of 30 Listing Image for 2481 Kaanapali Pkwy 413 21 of 30 Listing Image for 2481 Kaanapali Pkwy 413 22 of 30 Listing Image for 2481 Kaanapali Pkwy 413 23 of 30 Listing Image for 2481 Kaanapali Pkwy 413 24 of 30 Listing Image for 2481 Kaanapali Pkwy 413 25 of 30 Listing Image for 2481 Kaanapali Pkwy 413 26 of 30 Listing Image for 2481 Kaanapali Pkwy 413 27 of 30 Listing Image for 2481 Kaanapali Pkwy 413 28 of 30 Listing Image for 2481 Kaanapali Pkwy 413 29 of 30 Listing Image for 2481 Kaanapali Pkwy 413 30 of 30

$995,000

Whaler 413

2481 Kaanapali Pkwy 413, Kaanapali

0 Beds 1 Bath 523 SqFt Residential MLS® # 407257 Date Sold: December 30, 2025
Sold
Closed: 06/25/2026
Listing Image for 110 Kaanapali Shores Pl 109 1 of 49 Listing Image for 110 Kaanapali Shores Pl 109 2 of 49 Listing Image for 110 Kaanapali Shores Pl 109 3 of 49 Listing Image for 110 Kaanapali Shores Pl 109 4 of 49 Listing Image for 110 Kaanapali Shores Pl 109 5 of 49 Listing Image for 110 Kaanapali Shores Pl 109 6 of 49 Listing Image for 110 Kaanapali Shores Pl 109 7 of 49 Listing Image for 110 Kaanapali Shores Pl 109 8 of 49 Listing Image for 110 Kaanapali Shores Pl 109 9 of 49 Listing Image for 110 Kaanapali Shores Pl 109 10 of 49 Listing Image for 110 Kaanapali Shores Pl 109 11 of 49 Listing Image for 110 Kaanapali Shores Pl 109 12 of 49 Listing Image for 110 Kaanapali Shores Pl 109 13 of 49 Listing Image for 110 Kaanapali Shores Pl 109 14 of 49 Listing Image for 110 Kaanapali Shores Pl 109 15 of 49 Listing Image for 110 Kaanapali Shores Pl 109 16 of 49 Listing Image for 110 Kaanapali Shores Pl 109 17 of 49 Listing Image for 110 Kaanapali Shores Pl 109 18 of 49 Listing Image for 110 Kaanapali Shores Pl 109 19 of 49 Listing Image for 110 Kaanapali Shores Pl 109 20 of 49 Listing Image for 110 Kaanapali Shores Pl 109 21 of 49 Listing Image for 110 Kaanapali Shores Pl 109 22 of 49 Listing Image for 110 Kaanapali Shores Pl 109 23 of 49 Listing Image for 110 Kaanapali Shores Pl 109 24 of 49 Listing Image for 110 Kaanapali Shores Pl 109 25 of 49 Listing Image for 110 Kaanapali Shores Pl 109 26 of 49 Listing Image for 110 Kaanapali Shores Pl 109 27 of 49 Listing Image for 110 Kaanapali Shores Pl 109 28 of 49 Listing Image for 110 Kaanapali Shores Pl 109 29 of 49 Listing Image for 110 Kaanapali Shores Pl 109 30 of 49 Listing Image for 110 Kaanapali Shores Pl 109 31 of 49 Listing Image for 110 Kaanapali Shores Pl 109 32 of 49 Listing Image for 110 Kaanapali Shores Pl 109 33 of 49 Listing Image for 110 Kaanapali Shores Pl 109 34 of 49 Listing Image for 110 Kaanapali Shores Pl 109 35 of 49 Listing Image for 110 Kaanapali Shores Pl 109 36 of 49 Listing Image for 110 Kaanapali Shores Pl 109 37 of 49 Listing Image for 110 Kaanapali Shores Pl 109 38 of 49 Listing Image for 110 Kaanapali Shores Pl 109 39 of 49 Listing Image for 110 Kaanapali Shores Pl 109 40 of 49 Listing Image for 110 Kaanapali Shores Pl 109 41 of 49 Listing Image for 110 Kaanapali Shores Pl 109 42 of 49 Listing Image for 110 Kaanapali Shores Pl 109 43 of 49 Listing Image for 110 Kaanapali Shores Pl 109 44 of 49 Listing Image for 110 Kaanapali Shores Pl 109 45 of 49 Listing Image for 110 Kaanapali Shores Pl 109 46 of 49 Listing Image for 110 Kaanapali Shores Pl 109 47 of 49 Listing Image for 110 Kaanapali Shores Pl 109 48 of 49 Listing Image for 110 Kaanapali Shores Pl 109 49 of 49

$1,825,000

↓ $284,000

Mahana 109

110 Kaanapali Shores Pl 109, Kaanapali

2 Beds 2 Baths 1,214 SqFt Residential MLS® # 407256 Date Sold: June 25, 2026
Sold
Closed: 11/17/2025
Listing Image for 4327 Lower Honoapiilani Rd 408b 1 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 2 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 3 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 4 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 5 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 6 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 7 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 8 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 9 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 10 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 11 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 12 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 13 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 14 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 15 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 16 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 17 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 18 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 19 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 20 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 21 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 22 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 23 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 24 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 25 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 26 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 27 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 28 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 29 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 30 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 31 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 32 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 33 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 34 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 35 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 36 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 37 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 38 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 39 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 40 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 41 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 42 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 43 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 44 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 45 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 46 of 47 Listing Image for 4327 Lower Honoapiilani Rd 408b 47 of 47

$750,297

Valley Isle Resort 408B

4327 Lower Honoapiilani Rd 408b, Napili/Kahana/Honokowai

2 Beds 2 Baths 1,040 SqFt Residential MLS® # 407250 Date Sold: November 17, 2025
Sold
Closed: 09/26/2025
173 Oliona St 131, Makawao/Olinda/Haliimaile

$1,395,000

Hokuula

173 Oliona St 131, Makawao/Olinda/Haliimaile

4 Beds 3 Baths 1,456 SqFt Residential MLS® # 407244 Date Sold: September 26, 2025
Sold
Closed: 05/22/2026
Listing Image for 1123 Kehau Pl 1 of 50 Listing Image for 1123 Kehau Pl 2 of 50 Listing Image for 1123 Kehau Pl 3 of 50 Listing Image for 1123 Kehau Pl 4 of 50 Listing Image for 1123 Kehau Pl 5 of 50 Listing Image for 1123 Kehau Pl 6 of 50 Listing Image for 1123 Kehau Pl 7 of 50 Listing Image for 1123 Kehau Pl 8 of 50 Listing Image for 1123 Kehau Pl 9 of 50 Listing Image for 1123 Kehau Pl 10 of 50 Listing Image for 1123 Kehau Pl 11 of 50 Listing Image for 1123 Kehau Pl 12 of 50 Listing Image for 1123 Kehau Pl 13 of 50 Listing Image for 1123 Kehau Pl 14 of 50 Listing Image for 1123 Kehau Pl 15 of 50 Listing Image for 1123 Kehau Pl 16 of 50 Listing Image for 1123 Kehau Pl 17 of 50 Listing Image for 1123 Kehau Pl 18 of 50 Listing Image for 1123 Kehau Pl 19 of 50 Listing Image for 1123 Kehau Pl 20 of 50 Listing Image for 1123 Kehau Pl 21 of 50 Listing Image for 1123 Kehau Pl 22 of 50 Listing Image for 1123 Kehau Pl 23 of 50 Listing Image for 1123 Kehau Pl 24 of 50 Listing Image for 1123 Kehau Pl 25 of 50 Listing Image for 1123 Kehau Pl 26 of 50 Listing Image for 1123 Kehau Pl 27 of 50 Listing Image for 1123 Kehau Pl 28 of 50 Listing Image for 1123 Kehau Pl 29 of 50 Listing Image for 1123 Kehau Pl 30 of 50 Listing Image for 1123 Kehau Pl 31 of 50 Listing Image for 1123 Kehau Pl 32 of 50 Listing Image for 1123 Kehau Pl 33 of 50 Listing Image for 1123 Kehau Pl 34 of 50 Listing Image for 1123 Kehau Pl 35 of 50 Listing Image for 1123 Kehau Pl 36 of 50 Listing Image for 1123 Kehau Pl 37 of 50 Listing Image for 1123 Kehau Pl 38 of 50 Listing Image for 1123 Kehau Pl 39 of 50 Listing Image for 1123 Kehau Pl 40 of 50 Listing Image for 1123 Kehau Pl 41 of 50 Listing Image for 1123 Kehau Pl 42 of 50 Listing Image for 1123 Kehau Pl 43 of 50 Listing Image for 1123 Kehau Pl 44 of 50 Listing Image for 1123 Kehau Pl 45 of 50 Listing Image for 1123 Kehau Pl 46 of 50 Listing Image for 1123 Kehau Pl 47 of 50 Listing Image for 1123 Kehau Pl 48 of 50 Listing Image for 1123 Kehau Pl 49 of 50 Listing Image for 1123 Kehau Pl 50 of 50

$990,000

↓ $135,000

Makawao/Olinda/Haliimaile

1123 Kehau Pl, Makawao/Olinda/Haliimaile

3 Beds 1 Bath 1,392 SqFt Residential MLS® # 407239 Date Sold: May 22, 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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