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Move-up Buyer

Buying and Selling a Home at the Same Time Doesn't Have to Be Stressful

Discover the proven strategies to upgrade your Maryland home without the fear of paying two mortgages, moving twice, or ending up with nowhere to live.

A happy young family smiling and holding a moving box, ready to buy and sell a home at the same time in Maryland.

The “Catch-22” of Real Estate: Should You Buy First or Sell First?

If you are looking to upgrade, downsize, or simply change neighborhoods in Anne Arundel County, you are likely facing the biggest fear in real estate: timing.

If you buy your new house first, you risk carrying two mortgages. On the other hand, if you sell your home first, you risk having to move into a short-term rental or scrambling to find a new house in a competitive market.

It feels like a Catch-22, but it doesn’t have to be. As an experienced real estate agent in Pasadena, MD, I help clients navigate this exact scenario every single month. With the right strategy, you can seamlessly transition from one door to the next.

6 Ways to Buy a Home When You Need to Sell First

How do you actually buy and sell a home at the same time in Maryland? Based on your financial goals and timeline, here are the six most effective strategies we use to protect your equity and your sanity:

1. Buy Non-Contingent

With this option, the buyer would qualify to carry two mortgages at once and wouldn’t need to sell their home in order to buy a new one. This can be a great option for people who want to move quickly, and can afford the extra payments in holding costs. However, you may not qualify for as much of a loan carrying two mortgages.

2. Buy Contingent

Find a seller who is willing to let you sell your home first. In a seller’s market, this can be difficult to find, because there are usually plenty of other buyers able to buy without this contingency. The biggest downside to this option is that it is more risky for the seller, so they will often only accept this type of offer if the buyer is willing to pay a higher price or offer other concessions.

3. Temporary Housing

Sell your home and move into temporary housing with family or a rental property. This gives you the most flexibility when it comes to finding your next home. The downside is that you may have to move twice and pay for two sets of moving expenses. Short-term rentals can be hard to find and more expensive.

4. Rent Back

Use a post-settlement occupancy agreement to sell and stay in your home for up to 60 days. This gives you time to find a new place and move without the stress of having to do it all at once. You’ll also need to pay rent during this period, which is typically calculated as a per diem amount based on the buyer’s mortgage, plus a security deposit. Rent back agreements are negotiable, so be sure to talk to your real estate agent about this strategy.

5. Landlord

Rent out your home and use the rental income to offset your mortgage. Holding on to real estate as an investment can be a great strategy for building long-term wealth. This option can be challenging, as you’ll need to coordinate the closing on your new home with the lease agreement of your new tenants.

6. Bridge Loan

Obtain financing to leverage the equity in your home. Bridge loans are a financing option for homebuyers who need the proceeds from selling their current home to purchase a new one. This type of loan allows you to access your home’s equity to use as a down payment on the new property. Once the new home is purchased and the old one is sold, the bridge loan is repaid.

BONUS Strategy: Sellers Home of Choice

This addendum makes your home sale contingent on securing your next property-via purchase, financing, or lease-by set deadlines. If unmet, either party can cancel in writing, with deposits returned per the contract.

Introducing the Legacy Buyer Program

Buy a home with Real Creative Group and receive up to $1,200 in credits plus a $500 donation to a local scholarship fund. In your name.

Ready to Make Your Move?

You don’t have to figure out the timing of a double transaction on your own. Let’s sit down, review your options, and create a step-by-step strategy tailored to your timeline.

    How to Buy and Sell a Home at the Same Time

    The Real Creative Group Move-Up Framework

    We take the guesswork out of the double transaction. Here is exactly how my team and I coordinate your move from start to finish.

    Step 1: The Equity & Goal Assessment

    We start with a comprehensive home valuation to determine your current equity. Then, we map out your buying power and review the strategies to see which fits your life best.

    Step 2: The Prep & Search Phase

    While our award-winning production team prepares your current home for the market, we simultaneously set up hyper-local searches to find your next dream home.

    Step 3: The Synchronized Closing

    This is where our expertise shines. We expertly negotiate timelines, handle contingency periods, and align closing dates to make your transition as smooth as possible.

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    Hear From Clients Who Made the Move

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    Tony Noday profile picture
    Tony Noday
    Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
    My experience of working with James was great! He was very patient with us through the process. Responded to every text and call in a quick and professional manner. I really appreciated his honesty and feedback through this process. He took the time to explain everything clearly and answer all of our questions to the best of his knowledge. Very highly recommend! Feb. 2026: James also helped us sell this home. Once again, he provided outstanding service. Anyone buying or selling a home in the Anne Arundel County area, James should be at the top of your real estate agent list. He will work to understand what you’re looking for and what your situation is. Thank you for everything, James!
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    Carrie Scarabino profile picture
    Carrie Scarabino
    Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
    2026: Once again, James was fantastic to work with. We hired him to sell our home in Glen Burnie that we’d purchased in 2021. We appreciated his knowledge of the current market, expert recommendations, and effective communication skills. Five stars! 2021: James was fantastic. We were searching for a home to purchase while out of state. James was very helpful in searching for potential homes. Because we couldn’t be there for showings in person, James gave us very thorough tours via FaceTime which isn’t the easiest thing to do. Throughout the entire process, he was very honest, thorough, responsive and hardworking. We couldn’t have asked for a better realtor. We’ll be sure to refer him to anyone we know in the area looking to buy or sell a home. We will also choose him as our realtor in the event that we sell in the future. We highly recommend him.
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    Jake Linger profile picture
    Jake Linger
    Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
    James Bowerman was quick to send me leads on homes that fit my criteria, and when I was interested in a property, we were touring it within 24 hours. Any questions I had for James were answered quickly. The best part was — because I purchased my home via the First Time Homebuyer Program and it takes a little more time to close — James kept me grounded and calm when a property I liked didn’t work out. I would clearly highly recommend James.
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    Elso Sakian profile picture
    Elso Sakian
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    James was very friendly, responsive and was easy to work with from day 1. He was able to simplify the process of selling our house. I would recommend working with him in all your real estate needs.
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    Nelson Celis profile picture
    Nelson Celis
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    10/10 experience knows the market snd will negotiate the best deal for you
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    E Mail profile picture
    E Mail
    Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
    James was very friendly and accessible. I wanted an easy transaction, and James delivered! I liked how he listed my Pasadena home, the photos were great.
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    Brendan O'Donnell profile picture
    Brendan O'Donnell
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    James helped my family find our dream home! He provided exceptional customer service and was available at a moments notice.
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    Kevin Scott profile picture
    Kevin Scott
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    It was great working with James. He advised me throughout the whole process and helped find a great property.
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    Rhonda Dunn profile picture
    Rhonda Dunn
    Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
    I buy real estate on a semi regular basis, and would never think of using anyone but James. This time I sold one of my houses, it went under contract within a week! Such a smooth transaction, as always!! Highly recommend!
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    John Mason profile picture
    John Mason
    Google star 1Google star 2Google star 3Google star 4Google star 5Trustindex verifies that the original source of the review is Google.
    James is a total professional.... managing the sale of this property with great ease...
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    Frequently Asked Questions About Buying and Selling Simultaneously

    • If you are purchasing with a home sale contingency, you are protected. If your home doesn’t sell by the agreed-upon date, the contract on the new house can be voided, and your earnest money is returned. We aggressively market your home to ensure this doesn’t happen.

    • Usually, no! By utilizing a rent-back agreement or synchronizing the closing dates closely, you can pack up your current home and move your belongings directly into your new home on a single moving day.

    • Absolutely. You can use a bridge loan to access your home’s equity to use as a down payment on the new property, or wait until your current home closes and have the proceeds wired directly to the title company handling your new purchase.

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