Buy & Sell a Home at the Same Time

At Insiders Realty, we believe the order of operations matters. Whether you're upsizing, relocating, or timing two transactions together, this guide walks you through exactly how the process works - and how we guide you every step of the way.

Why buy & sell with insiders realty?

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TO US, A MOVE IS MORE THAN JUST A TIMELINE.

It’s a series of important decisions that deserve clarity, strategy, and guidance. Whether you’re buying, selling, or doing both at the same time, our role is to help you move forward with confidence - not confusion.

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Before You Buy & Sell, Watch This.

Buying and selling at the same time can feel overwhelming without a clear plan. In this video, Cait Berry walks you through the step-by-step process Insiders Realty uses to help clients navigate a double move with confidence. From deciding whether to buy or sell first to understanding timelines, offers, and closing strategies, this guide is designed to help you feel prepared before making your next move.

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a proven process

for buying and selling at the same time

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Buy First
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Sell Second

Buy First

Clarity Before Big Decisions

Our approach often begins with securing your next home first because it gives you clarity before making decisions about your current one. Buying first helps ensure you land on the right home for your needs without feeling rushed into a fast decision just to keep timelines aligned. When you know where you’re going, the entire process becomes more intentional and far less stressful.

Many clients use tools like a HELOC or interest-only bridge loan to access equity for their down payment, allowing them to close on their next home before selling. One of the biggest reasons clients love this strategy is simple - they don’t have to live through the chaos of showings. You get to settle into your next home first, while we take care of staging, prep, and launching your sale behind the scenes.

Sell Second

Sell With Strategy and Timing

Once your next home is secured, we shift our focus to preparing and positioning your current home to stand out. Selling second allows us to be more strategic with pricing, presentation, and timing because you’re no longer making decisions from a place of urgency. With a clear plan already in motion, we can market your home thoughtfully, attract the right buyers, and guide you through the contract-to-close phase with confidence. The goal is to create momentum without overwhelm - turning two major transactions into one cohesive, manageable process.

Clients love this approach because it gives them space to make confident decisions and fully enjoy the excitement of what comes next. Instead of feeling rushed or reactive, they experience a process that feels organized, supported, and intentional - often walking away feeling like they truly won on both sides of the move.

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The Right Order Makes Everything Easier

frequently asked questions

There isn’t one right answer for everyone, but the majority of our clients start by securing their next home first so decisions about selling don’t feel rushed. Madison’s market conditions, your financial position, and your comfort level with timelines all play a role. During your strategy session, we map out a plan that fits your situation rather than relying on a one-size-fits-all approach.

A double move simply means coordinating the sale of your current home with the purchase of your next one. It can feel stressful because there are multiple timelines, negotiations, and decisions happening at once. Our role at Insiders Realty is to break that process into clear phases so you always know what comes next and why.

Yes, many Madison-area buyers do - especially when we structure a thoughtful plan around financing, contingencies, and timing. Buying first can provide clarity and reduce pressure, but we always evaluate the risks and options together before moving forward.

Not necessarily - and honestly, it's very unlikely. We excel at helping clients use bridge loan strategies or carefully timed closings to avoid overlap. Every situation is different, which is why building a personalized strategy early in the process is so important.

Contingent offers allow you to make an offer on a new home while your current home is still part of the process, but they do come with added challenges. In a competitive Madison market, contingent offers are often less appealing to sellers because they introduce more uncertainty. Some contracts include a “bump clause,” which means another buyer can step in and potentially replace your offer if their terms are stronger. Because of this, we spend time upfront discussing strategy - whether that means strengthening your offer, preparing your home early, or exploring alternative options - so you understand both the benefits and the risks before moving forward.

Part of our preparation includes pricing, presentation, and marketing designed to attract strong interest early. If activity slows, we review feedback, adjust strategy, and keep you informed so decisions feel proactive rather than reactive.

We help you prioritize what matters most - from staging guidance to timing photography and showings - so the process feels manageable. Many clients are surprised by how organized everything feels once there’s a clear plan in place.

Buying and selling at the same time can feel complex without a clear plan. In some cases, it can actually be riskier to put your home on the market first, accept an offer, and then feel pressured to make a fast buying decision just to keep timelines aligned. That urgency can lead to compromises that don’t always serve your long-term goals. With a thoughtful strategy and clear communication, our goal is to remove that pressure by mapping out each phase ahead of time - so decisions feel intentional, not rushed, and the process feels more manageable from start to finish.

 

Timelines vary depending on the season, inventory levels, and your goals. Some moves happen quickly, while others unfold over several months. During your consultation, we create a realistic timeline so expectations feel clear from the start.

Guiding clients through buying and selling at the same time is truly one of our specialties. As lifelong Madison locals, we combine deep neighborhood insight with a clear, step-by-step process designed to reduce stress and keep you informed at every stage. We take the time to truly understand your goals, your timeline, and what matters most to you, creating a plan that feels thoughtful, supportive, and easy to follow from beginning to end. Our goal is simple: to help you feel confident and at ease long before closing day arrives.

Not at all. Many clients start by simply exploring their options. The first step is a conversation - we’ll help you understand what’s possible and create a plan that feels right for you.

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Insiders Realty

Phone

(608) 576-1125

Email

[email protected]

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