By Jason Boice, REALTOR®, eXp Realty — Published on August 7, 2026
One of the biggest reasons homeowners delay selling isn't because they're worried about price.
It's because they're worried about timing.
Questions like:
"What if my home sells before I find another one?"
"Can I buy first?"
"Do I have to move twice?"
"What if all of my money is tied up in my current house?"
"How do I avoid feeling rushed?"
These are some of the most common questions I hear from homeowners in Hebron.
The good news is that there isn't just one way to buy and sell at the same time.
There are multiple strategies.
The best one depends on your finances, your goals, your timeline, and the type of property you're trying to buy.
In this article, I'll walk through two real client examples that solved the exact same problem in completely different ways.
TL;DR
If you're selling your home in Hebron and buying another one, you may be able to:
Sell first, then buy
Buy first, then sell
Coordinate same-day closings
Negotiate post-closing occupancy
Use bridge financing
Include sale contingencies
Customize the entire timeline around your goals
There isn't one "correct" strategy.
The best strategy is the one that fits your situation.
The Biggest Mistake Homeowners Make
Many people assume they have only two choices:
Sell too early...
Or buy too early.
In reality, there are often several different ways to structure a move.
The biggest mistake is making a decision before understanding all of your options.
When we start planning months before your home goes on the market, we typically have far more flexibility than homeowners realize.
Start With Your Timeline—Not the Market
Most people ask:
"When should I list?"
I usually ask something different.
"When do you want your next chapter to begin?"
Maybe that's:
Before school starts.
After retirement.
Before winter.
After a new job begins.
Once you've found your forever home.
Once we know your goal, we can build the transaction around it.
There Isn't One Right Strategy
Some homeowners should sell first.
Others should buy first.
Some need bridge financing.
Others need sale proceeds.
Some want to coordinate a same-day closing.
Others negotiate additional time after closing.
The strategy isn't determined by the market.
It's determined by you.
Here are two real examples.
Case Study #1: Selling First Made the Most Sense
One client came to me looking to downsize.
She owned a 2,400-square-foot, four-bedroom Colonial on 14 acres in Colchester.
The property had become more maintenance than she wanted in retirement.
Like many homeowners, almost all of her available cash was tied up in the equity in her home.
That meant buying first simply wasn't realistic.
Instead, we built a strategy around selling first.
The Plan
Rather than rushing to buy, we focused on maximizing the sale of her current home.
We:
Prepared the home for the market.
Priced it strategically.
Launched a comprehensive marketing campaign.
Generated maximum buyer exposure.
The results exceeded expectations.
Property: 435 Old Hebron Rd., Colchester
Listed at $625,000
Under contract in 3 days
19 offers
Sold for $735,500
$110,500 over asking
Buyer waived inspection contingency
Buyer waived appraisal contingency
Once we had the sale secured, we shifted our attention entirely to finding her next home.
She had fallen in love with a property in Hebron that had gone under contract with another buyer.
Instead of giving up, we stayed in regular contact with the listing agent.
When that transaction fell apart over inspection issues, we were ready.
Because our client was already under contract—and financially prepared—we were able to move quickly.
We negotiated the purchase, coordinated both closings, and even negotiated two additional days of post-closing occupancy so she could move once without feeling rushed.
From listing to closing, the entire process took just 30 days.
The Lesson
Selling first gave her certainty.
She knew exactly how much money she had available.
She avoided carrying two homes.
She moved once.
And she never needed temporary housing.
Case Study #2: Buying First Was the Better Strategy
Another client had a completely different situation.
They already had enough cash and financing to qualify for their next home before selling their current one.
Instead of rushing to list their Hebron home, we focused on finding one very specific property.
A waterfront home.
We searched both the public market and off-market opportunities.
Eventually we located the perfect property before it ever hit the open market.
We negotiated the purchase privately.
Once they successfully closed on the new waterfront home and moved in, we turned our attention to preparing their previous Hebron home for sale.
Because they had already moved, the process became dramatically easier.
We were able to:
Declutter completely.
Paint without disruption.
Professionally clean the home.
Stage each room.
Photograph an empty, beautifully prepared property.
Schedule showings without inconveniencing the family.
Only after everything was ready did we list the home.
Results
Property: 29 Chestnut Hill Road, Hebron
Listed at $599,900
Multiple offers
Under contract in 5 days
Sold for $615,000
By purchasing first, they eliminated the stress of coordinating two moves and were able to prepare their home for the market without living in it.
The Lesson
Buying first isn't always possible.
But when a homeowner has the financial ability to do it, it can create tremendous flexibility.
Instead of racing against a closing date, they were able to move on their own schedule and present their home in its best possible condition before listing it.
Two Clients. Two Different Strategies. Two Successful Outcomes.
At first glance, these clients had the same objective:
Sell one home.
Buy another.
But because their financial situations were different, the right strategy was completely different.
That's why there isn't a universal answer to questions like:
Should I sell first?
Should I buy first?
How do I avoid moving twice?
When should I list?
The answer depends on your circumstances.
The Right Strategy Starts With a Conversation
Buying and selling at the same time is one of the most complex transactions many homeowners will ever complete.
But it doesn't have to feel overwhelming.
When you begin planning early, you often have more options than you realize.
Sometimes selling first is the best strategy.
Sometimes buying first makes more sense.
Sometimes bridge financing is the right answer.
Sometimes negotiating occupancy after closing solves the problem.
The key is understanding your options before making decisions.
Thinking About Selling Your Home in Hebron?
If you're considering a move but aren't sure how to coordinate the timing, let's build a strategy that works for your situation.
Together we'll discuss:
Your home's current value
Your estimated net proceeds
Whether selling first or buying first makes more sense
Financing options
Flexible closing strategies
How to avoid moving twice
Creating a plan that fits your timeline
You may also find these articles helpful:
Selling and Buying at the Same Time: How to Plan It
How to Avoid Getting Stuck Between Selling and Buying
Should You Sell First or Buy First?
What to Expect on Closing Day as a Seller
How Much Does It Cost to Sell a House in Connecticut?
Or call or text 860-452-3153 for a no-pressure consultation.
Frequently Asked Questions
Can I buy a new home before selling my current one?
Yes. If you have sufficient cash, financing, or bridge loan options, buying first may allow you to move at a more relaxed pace and prepare your current home after you've moved out.
What if I need the equity from my current home to buy my next one?
Selling first is often the best strategy. With proper planning, same-day closings or negotiated post-closing occupancy can help you avoid temporary housing and move only once.
Can I stay in my home after closing?
Sometimes. A post-closing occupancy agreement (also called a rent-back agreement) can allow you to remain in the home for an agreed-upon period after closing if both parties agree.
How do I avoid moving twice?
Early planning is key. Depending on your circumstances, strategies such as selling first, buying first, bridge financing, same-day closings, or post-closing occupancy agreements can help you move directly from one home to the next.
Is there one best strategy for everyone?
No. The best approach depends on your finances, your goals, the current market, and your replacement housing plans. That's why a customized strategy is so important.
About the Author
Jason Boice is a REALTOR® with eXp Realty serving Hebron, Marlborough, Colchester, East Hampton, Andover, Columbia, Portland, Tolland, and surrounding Connecticut communities.
Jason specializes in helping homeowners navigate complex buy-and-sell transactions by creating customized strategies that align with each client's financial situation, timeline, and long-term goals. Rather than using a one-size-fits-all approach, he helps clients choose the path that maximizes flexibility, minimizes stress, and supports a smooth transition to their next chapter.
Call or text: 860-452-3153
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