Stay organized when buying & selling a home at the same time.
Remember that time you thought assembling your kid’s bike on Christmas Eve would be “no big deal”?
Yeah. Buying and selling a home simultaneously is like that…but with your life savings on the line.
If you’re considering moving to Winter Garden or Clermont this spring, you’re probably facing the real estate chicken-and-egg dilemma. Do you sell first then buy, or buy first then sell? You’re juggling closing dates, moving logistics, and maybe temporary housing in between.
I’ve helped a lot of families move through these changes. I can tell you the secret to success isn’t luck – it’s methodical planning.
For example, some homeowners can buy first, while others need to sell first. So, let’s explore the most common scenarios and how to handle them effectively.
The “Both Ends Burning” Dilemma
Let’s address the biggest fear right away: ending up with two mortgages… or worse, no home at all.
Most homeowners fall into one of these common scenarios:
- The Nothing-To-Lose Buyer: You’re currently renting and buying your first home (the simplest scenario)
- The Bridge-Crosser: You need to sell your current home to fund the down payment on the next one
- The Equity-Maxer: You have enough savings to buy first, then sell your existing home
- The Temporary-Housing Tactician: You’re willing to sell first, move to temporary housing, then buy
The truth most realtors won’t tell you: None of these approaches is universally “best.” The right strategy depends entirely on your financial situation, risk tolerance, and the current market conditions in your specific neighborhood.
Recently, I helped a family in Clermont use strategy #2 while their neighbors across the street succeeded with strategy #3. Same neighborhood, different circumstances, completely different approaches.
60-Days Before Moving: Laying the Groundwork
Whether you’re buying first or selling first, your two-month countdown begins with the same critical steps:
1. Get Your Financial House in Order
Before listing or shopping, gather these documents:
- Recent mortgage statements
- Home insurance policies
- Property tax statements
- HOA documents (if applicable)
- Recent utility bills
- Home repair records
Pro dad hack: Create a dedicated email folder for all house-related communications. Label everything clearly. Your future self will send you a thank-you note.
💡 Pro Tip: Before making any moves, ensure you understand the financial side of buying and selling a home at the same time. Redfin’s step-by-step guide breaks down their own strategies.
Once your financial documents are in order, the next step is tackling the physical side of moving—decluttering. In addition, decluttering early helps make staging and packing easier.
2. The Great Purge: Declutter Like You Mean It
Moving is the perfect excuse to evaluate every possession with ruthless clarity. For each item, ask:
- Does it serve a purpose in our next chapter?
- Would it cost less to replace it than to move it?
- When was the last time we actually used it?
The psychology of letting go: Most Winter Garden and Clermont homes have at least three rooms’ worth of items that the owners don’t use, don’t need, and won’t miss. Yet we hold onto them because… someday?
The three-pile system that works:
- Keep and use now
- Keep but store until after moving
- Donate/sell/discard
💡 Not sure where to donate locally? Instead of tossing usable items, consider donating furniture, appliances, and building materials to Habitat for Humanity ReStore in Winter Garden or household goods and clothing to Central Florida Hope Center.
After decluttering, it’s time to focus on assembling your real estate dream team. In other words, you’ll need the right professionals to make this transition as smooth as possible.
3. Assemble Your Real Estate Dream Team
At minimum, you’ll need:
- A trusted realtor who understands your specific market (ahem)
- A responsive mortgage lender (ask for recommendations)
- A reliable home inspector
- A title company (especially for complicated transactions)
The one question to ask each professional: “What percentage of your clients are buying and selling simultaneously, and what strategies have worked best recently?”
The answer tells you immediately whether they’re experienced with your specific scenario.
30-Days Before Moving: Strategic Execution
With your foundation set, the 30-day countdown is all about synchronizing timelines.
1. Coordination is Key: The Ideal Timeline
If selling first:
- List your home with a settlement date minimum 45 days out
- Include a rent-back contingency in case your new home isn’t ready
- Have pre-approval ready for your new purchase
- Begin house hunting actively once your home is under contract
If buying first:
- Secure pre-approval for a new mortgage that accounts for your current one
- Make offers with settlement dates that allow time to sell your current home
- Consider a home equity line of credit (HELOC) as a bridge financing option
- Prepare your existing home for listing while house hunting
The crucial contingency: If you must sell to buy, make your purchase offer contingent on the sale of your current home. Yes, it makes your offer slightly less competitive, but it prevents financial disaster.
With your timeline in place, the next step is scheduling everything in advance. For example, you’ll need to coordinate home inspections, appraisals, and final walk-throughs to prevent last-minute surprises.
2. Schedule Everything…Then Add Buffer Time
- Home inspections (for selling and buying)
- Appraisals
- Final walk-throughs
- Closing appointments
- Moving company (book at least 3 weeks in advance)
- Utility disconnection/connection
- Mail forwarding
- School transfers (if applicable)
The buffer rule: Whatever time you think a task will take, add 30%. Moving always takes longer than expected, especially when children are involved. (My record is finding a missing hamster 20 minutes before the moving truck arrived.)
Since everything is on schedule, now is the perfect time to start packing strategically. First, focus on non-essentials, such as seasonal items and books. Then, as moving day gets closer, pack the rest of your belongings.
3. Start Packing Non-Essentials
Begin with:
- Seasonal items
- Books and decorative objects
- Extra kitchen supplies
- Off-season clothing
- Hobby equipment
- Guest room contents
Labeling system that saves marriages: Color-code boxes by room AND number them sequentially with a master list of contents. When your spouse asks where the coffee maker is, you’ll know it’s in “Kitchen Box #3” rather than “somewhere in one of those 47 boxes.”
One Week Before Moving: Final Countdown
The final week is where even the best plans face reality. Stay focused on these priorities:
1. Essential Documents Box
Create one clearly marked box containing:
- Closing documents for both properties
- Insurance policies
- Medical records
- School documents
- Financial documents
- Pet records
- Birth certificates and IDs
This box travels with you, not on the moving truck. Trust me on this one.
While your paperwork is safely packed, don’t forget about first-night necessities. In particular, items like toiletries, medications, and chargers should be easily accessible.
2. First Night Essentials
Pack a separate box for each family member with:
- Two days of clothing
- Toiletries
- Medications
- Phone chargers
- Comfort items (especially for children)
For the household, prepare a “first night” box with:
- Basic kitchen supplies
- Paper plates and plastic utensils
- Coffee maker and coffee (non-negotiable)
- Basic cleaning supplies
- Toilet paper and paper towels
- Shower curtain and towels
- Sheets and pillows
- Basic tools
- Nightlights for unfamiliar spaces
The forgotten five: Based on dozens of client moves, the most commonly forgotten essential items are shower curtains, phone chargers, pet food, prescription medications, and the TV remote. Don’t be that statistic.
3. Final Logistics Check
- Confirm closing times for both properties
- Verify moving truck arrival time
- Arrange childcare and pet care for moving day (pro tip: a tired dog is a good dog on moving day—Maizey gets an extra-long morning walk before any move)
- Complete change of address forms
- Schedule locksmith to change locks on new home
- Transfer/set up internet service
- Withdraw cash for tipping movers
Moving day feeding strategy: Prep a cooler with water, sandwich supplies, and snacks. Don’t forget treats for four-legged family members too (Maizey once stole an entire submarine sandwich during our move when we forgot her lunch). Moving is physically demanding, and everyone gets irritable when hungry. Feed your people—and your pets.
At this stage, everything should be scheduled and confirmed. However, moving day can still be unpredictable. Therefore, having a final logistics checklist will ensure a smooth transition.
Moving Day: Execution Mode
This is game day. Your preparation will pay off if you focus on these priorities:
1. Divide and Conquer
If you have a partner or family members, assign clear roles:
- One person at the current home with movers
- One person at the new home directing traffic
- One person managing kids and pets (Maizey has her own moving day “supervisor” when we relocate clients)
- One person handling documentation
If you’re moving solo, consider hiring help or recruiting friends for specific time slots with clearly defined roles.
Before you lock up for the last time, take a final walk-through of your home. This step is essential because it ensures that nothing important is left behind.
2. Final Walk-Through Protocol
For the home you’re selling:
- Check all closets, cabinets, and storage spaces
- Look under appliances
- Check the garage, attic, and outdoor storage
- Confirm all keys, garage openers, and access cards are accounted for
For the home you’re buying:
- Verify all agreed-upon repairs are completed
- Test all appliances
- Run water in all sinks, flush toilets
- Test HVAC system
- Check for any new damage since inspection
The “leave it better” principle: Even when you’re exhausted, clean your old home thoroughly before leaving. It’s both courteous and good karma for your new place.
Now that the heavy lifting is done, it’s time to settle in. First, focus on unpacking the essentials, such as beds, toiletries, and kitchen supplies. After that, you can gradually organize the rest of your home.
3. First Night Setup
Focus solely on:
- Setting up beds
- Locating essential medications
- Ensuring basic bathroom functionality
- Securing food for the evening
- Making coffee setup ready for morning
Reality check: Your first night will be chaotic. Embrace it, order pizza, and remember that by this time tomorrow, you’ll have made significant progress.
After the Move: The First Week
Once you’ve survived moving day, focus on these priorities:
1. Security First
- Change locks
- Test smoke and carbon monoxide detectors
- Locate water and gas shut-off valves
- Program the security system
- Identify electrical panel
2. Methodical Unpacking
Start with:
- Kitchen essentials
- Bedroom and bathroom necessities
- Kids’ rooms (helps establish normalcy)
- Home office (if you work from home)
- Living areas
The one-box-a-day minimum: Commit to unpacking at least one box every day, no matter how tired you are. This prevents the semi-moved-in limbo that can last for months.
3. Connect with Your New Community
- Introduce yourself to neighbors
- Locate essential services (grocery, pharmacy, urgent care)
- Find nearby parks and recreation
- Research local community events
The lawn chair trick: One of my Winter Garden clients placed lawn chairs in their front yard the first evening in their new home. They met most of their neighbors in a single evening as curious folks stopped by to welcome them.
The Bridge Strategy: When Timing Doesn’t Align
Sometimes perfect timing isn’t possible. If you face a gap between selling and buying, consider these options:
1. Rent-Back Agreement
Negotiate to stay in your sold home for a specified period, paying rent to the new owner. This works well when:
- The buyer isn’t in a rush to move in
- You need less than 60 days
- You’re willing to pay slightly above-market rent
If a rent-back agreement isn’t an option, short-term housing might be the best alternative. In fact, many homeowners use extended-stay hotels or vacation rentals to bridge the gap.
2. Short-Term Housing
Research these options now, even if you think you won’t need them:
- Extended-stay hotels (many in the Winter Garden/Clermont area offer monthly rates)
- Short-term apartment leases (typically 3-month minimum)
- Vacation rentals (often available for monthly rentals between tourist seasons)
- Family or friends with guest accommodations
Storage considerations: If using temporary housing, you’ll likely need storage units. Reserve climate-controlled units early, especially during peak spring/summer moving season.
For those who want to avoid moving twice, bridge loans can provide a financial cushion. As a result, homeowners can purchase their new home before selling the old one.
3. Bridge Loan Options
If you find your dream home before selling your current one, bridge financing can help. Options include:
- Home equity line of credit (HELOC)
- Bridge loans specifically designed for gap periods
- 401(k) loans (use with caution and consult a financial advisor)
The financial reality check: Bridge financing typically comes with higher interest rates and fees. Run the numbers carefully to ensure the cost doesn’t outweigh the convenience.
The Emotional Side of Moving
Let’s acknowledge something important: moving is emotionally exhausting, especially when coordinating both buying and selling.
For parents: Children thrive on routine and predictability – exactly what’s disrupted during a move. Schedule regular check-ins with each child and maintain as many normal routines as possible. Even teenagers need extra support, though they may not admit it.
For couples: Moving consistently ranks among life’s top stressors. Plan regular breaks from moving tasks – even 30 minutes to grab coffee together without discussing the move can reset your perspective.
For everyone: Build in small celebrations for milestones. Sold your house? Pop a bottle of champagne. Closed on the new place? Order your favorite takeout. The work of moving can overshadow the achievement it represents without intentional celebration.
The Bottom Line: Preparation Beats Panic
The difference between a moving nightmare and a manageable transition is preparation. By breaking down this complex process into specific timelines with clear action items, you transform an overwhelming project into a series of manageable steps.
Remember: thousands of Winter Garden and Clermont families successfully navigate buying and selling simultaneously every year. With thoughtful planning and the right support team, you’ll soon be among them, enjoying your new home and wondering why you kept all that stuff in your old garage for so long.
Ready to coordinate your Winter Garden or Clermont move with confidence? Let’s create a customized timeline that aligns your selling and buying strategies with current market conditions. Your dream of a smooth transition from old house to new home is just a phone call away!
