Two Moves, One Calendar
How to sell your home up north and buy in The Villages without paying for two homes or living out of a suitcase.
Who this guide is for
You found The Villages. Maybe you visited a friend, maybe you've watched every video online for a year. You're ready.
Then the real question hits. "What if we close here before our house up north sells?" Or the other one: "What if our house sells and we have nowhere to go?"
That worry is fair. You're not making one move. You're making two, in two states, with two sets of paperwork, two closings and one moving truck. When those two moves run on separate calendars, they collide.
This guide puts both moves on one calendar. You'll learn:
- The three ways to order your two moves, and what each one costs you in money and stress
- What happens up north and here, month by month, counted back from move-in day
- How to see homes from far away so your trip here is for deciding, not browsing
- How to close from two states and have the keys and the moving truck show up together
I've walked this road before. It's not new to me. Let's take it step by step.
Pick your order first
Before you look at a single home, decide which move goes first. Everything else on the calendar follows from this one choice.
Option 1: Sell first, then buy
You sell your home up north, then buy here with the money in hand.
- What you gain: you know your exact budget. You're not paying for two homes. Your offer here is stronger because it doesn't depend on another sale.
- What it costs you: you may need a place to stay between the two moves. That could be a few weeks with family, a short rental here, or asking your buyer up north to let you stay a little after closing. That last one is called a rent-back.
Option 2: Buy first, then sell
You buy here, move in, then sell the home up north.
- What you gain: you get the home you want, on your timeline, and you move once.
- What it costs you: for a while you may own two homes, with two sets of taxes, insurance and utilities. Some buyers pay cash here. Others use a short-term loan against the home up north, called a bridge loan. Whether either one makes sense for you is a question for your lender and your financial advisor. I'll help you ask the right questions.
Option 3: Both closing the same week
You sell up north and buy here, with the two closings a few days apart.
- What you gain: no double payments and no gap.
- What it costs you: it takes the most planning. If one closing slips, the other feels it. Your offer here usually includes a clause that lets you step back if your home up north doesn't sell by a set date. That clause is called a sale contingency. Some sellers accept it and some don't.
Here's the move: there is no wrong answer, only the one that fits your money and your nerves. On our call, we'll pick yours together.
The timeline, counted back from move-in day
Pick the day you want to sleep in your new home. Then count backward. Start six months out. Here's what happens on each side, step by step.
Six months out
- Up north: Your agent up north is chosen (see section 4). You start sorting what comes with you and what stays.
- Here: We talk for 30 minutes. You pick your order of moves. You talk to a lender about pre-approval, which is a letter showing how much you can borrow. If you're paying cash, you gather proof of funds.
Four months out
- Up north: Your agent walks through your home and tells you what to fix, what to leave alone, and what it could sell for.
- Here: I send you video tours of homes and villages that match how you want to live. You narrow it down to two or three villages.
Three months out
- Up north: Your home goes on the market.
- Here: You take one focused trip to see the homes on your short list (see section 5).
When your home up north gets an offer
- Up north: You accept an offer. Inspections and the buyer's appraisal follow.
- Here: You write your offer. I line up your closing date here with your closing date up north.
A purchase here usually takes about 30 to 45 days from signed contract to closing with a loan, and about 2 to 3 weeks with cash.
The first two weeks under contract
- Up north: The buyer's inspection and appraisal happen. Repairs are agreed on.
- Here: Your inspection happens. I review the report with you, in plain English, and we decide what to ask for.
30 days out
- Up north: Your title company sends your closing numbers.
- Here: Your title company sends yours. You book the movers for a date that fits both closings. You set up power, water, internet and trash at the new home.
Two weeks out
- Up north: You confirm the moving truck's pickup day. You start packing in earnest.
- Here: You confirm the closing time and how you'll sign (see section 6).
Closing week
- Up north: Usually the home up north closes first, so the money from the sale is ready for the purchase.
- Here: You close, I hand you the keys, and the truck arrives within a day or two.
Your takeaway: every step up north has a matching step here. When both sides run on one calendar, nothing sneaks up on you.
Your agent up north, picked by me
You need a good agent where you live now. You don't have to find one on your own.
I hand-pick the agent who sells your home up north. Then I stay in touch with them until both closings are done, so you're not stuck relaying messages between two people in two states. When your home up north gets an offer, I know about it the same day, and I adjust your timeline here.
Here's how I pick them. I start with agents I've worked with before, or ones recommended by agents I trust. I interview two or three before I choose. Then I talk with that agent every week until both closings are done.
You talk to one person about the whole move: me.
Seeing homes from far away
The Villages is big. It covers parts of three counties, and each village has its own feel, its own prices and its own fees. Flying down to "look around" usually means a tiring week and no decision.
Here's a better way:
- First, live video. I walk the home on a live video call, on FaceTime, WhatsApp or Zoom, while you watch and ask questions. You see the homes, the street and the drive to the nearest town square before you book a flight.
- Then, one focused trip. By the time you fly in, your list is short. You see three to six homes in one or two days. You drive the routes you'll actually use, to the doctor, the grocery store and the pickleball courts.
- Then, decide. Your trip is for deciding, not browsing.
Many buyers ask me, "What if we hate it after we move?" The focused trip is how you answer that before you buy, not after.
Closing from two states
You don't have to be in two places at once.
- Signing: you don't have to fly in to sign. The title company mails your closing papers, and a notary meets you where you live to sign them.
- The money: when you close up north first, the money from your sale goes to the title company here. Your title company tells you exactly how, and you call them to confirm the instructions before any money moves. Wire fraud is real, and a quick phone call stops it.
- The keys and the truck: I book your final walkthrough for the day before or the morning of closing. Your movers get a delivery date after your closing, so the truck doesn't show up at a home you don't own yet.
Once you're here, there's a short list of Florida deadlines: your driver's license, your car registration and your homestead exemption, which lowers your property taxes. My free Moving Guide walks you through each one.
Your one-page calendar
Print this. Write your own dates in the blanks.
Move-in day: ________
| When | Up north | Here in The Villages |
|---|---|---|
| ☐ 6 months out | Agent up north chosen. Start sorting what comes with you. | 30-minute call. Pick your order. Pre-approval or proof of funds. |
| ☐ 4 months out | Walk-through and price | Video tours. Narrow to 2 or 3 villages. |
| ☐ 3 months out | Home goes on the market | One focused trip |
| ☐ Offer up north | Accept an offer | Write your offer. Match the closing dates. |
| ☐ First 2 weeks under contract | Their inspection and appraisal | Your inspection |
| ☐ 30 days out | Closing numbers | Closing numbers. Movers booked. Utilities set up. |
| ☐ 2 weeks out | Truck pickup confirmed. Pack. | Closing time and signing confirmed |
| ☐ Closing week | Close first | Close. Keys. Truck arrives. |
Your next move
You now know the three ways to order your move and what happens on each side, month by month. You also know where the two moves usually collide.
The next step is your calendar with your real dates on it. That's what we do on a free 30-minute call. You tell me when you want to be here and where you're coming from. I tell you which order fits, when to call the agent up north, and when to book your trip. You leave the call with a plan, and there's no obligation.
Book your free 30-minute call: calendly.com/liliwhittington
Or call or text me at 352-715-3515.
About Lili
I help people relocating to The Villages buy their home, and I help Villages homeowners sell, in English or Spanish. I've spent more than 20 years in Florida real estate and sold more than 450 homes. I've lived and worked in The Villages since 2016.
I'm a Seniors Real Estate Specialist (SRES) and a Military Relocation Professional (MRP). I handle your move as one move: I pick the agent who sells your home up north, I handle your purchase here, and I keep both on one calendar.
Lili Whittington, MBA, Broker Associate The Lili Whittington Group | Soundings LLC | FL License BK3090328 352-715-3515 | whittingtonteam.com
This guide is general information, not legal, tax or financial advice. Talk with your lender, attorney or tax advisor about your situation.
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