Moving From Connecticut to Florida or the Carolinas? Sell Your House in the Right Order
You already know where you want to wake up next winter. The hard part is getting there in the right order.
Maybe it's the grandkids in Tampa or Charlotte. Maybe it's the shoveling, the heating oil or a tax bill that keeps climbing. Whatever the reason, moving from Connecticut to Florida or the Carolinas is one of the biggest financial moves you'll ever make. The order you do things in can cost you, or save you, real money.
You're far from alone. About 9,800 people moved from Connecticut to Florida in 2024, according to Census Bureau estimates — only New York and Massachusetts drew more Connecticut movers. If property taxes are a big part of why you're leaving, start there for the full picture. This guide is about the move itself: what to decide first, how to close from out of state, and which taxes follow you south.
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Moving From Connecticut to Florida: Sell First or Buy First?
This is the first fork in the road, and there's no single right answer. There's only the right answer for your money and your peace of mind.
Selling first
Selling first means you know exactly how much cash you have before you shop. You avoid paying two tax bills, two insurance policies and two sets of utilities. The catch: you need somewhere to land in between — a rental, a family member's guest room or a short-term lease — unless you can line up both closings close together.
Buying first
Buying first means you can move straight into your new home. The catch: you carry both houses until the Connecticut one sells, and an empty house in a Connecticut January needs heat, regular checks and a plan. A frozen pipe can do far more damage when no one is home to notice it — here's what happens when burst pipes damage a house you're trying to sell.
The middle path
A sale with a closing date you choose can line up with your closing down south, so you move once without carrying two houses for months. That's where a cash sale helps most: the timeline is yours to set.
CT Homeowners Love Us!
Here’s how HHB helped people move forward—quickly, quietly, and on their own terms.
Sharon Kiraly
Fairfield, CT
..he made a very fair and equitable offer to purchase my home of 30 years and was sensitive to all my cherished memories of living there, raising my family, and then parting, making it a bearable transition.
I’m very grateful to Daniel Riccio.
Louis - Macdonald
Road Trumbull, CT
The entire process ran smooth and the company was extremely accommodating to our family's needs. They were understanding and gave us the opportunity to have extra time after the sale to sort through our belongings. Whatever we no longer wanted they kindly let us keep on the property and they took care of it for us.
I would highly recommend working with them!
Karen Mavilia
Howe Ave Shelton, CT
Second time with Dan Riccio and and his all-star team -- a rental property in 2019, now my home in January 2025. Flawless synchronicity from start to finish. Downright upright ethics -- so rare today. All commitments met and expectations exceeded. 24/7 project management, impressive array of skilled contractors resolved all issues in a timely professional manner. Best of all, I simply took what I wanted and left all remaining contents.
Know What You'll Actually Walk Away With
Before you make an offer on a new home, get clear on what your Connecticut sale will really net. Three items deserve a hard look — and a conversation with your CPA.
- Connecticut's conveyance tax. When you sell, Connecticut charges a state conveyance tax of 0.75% on the first $800,000 of a residential sale. Towns add a 0.25% municipal tax, and certain targeted investment communities can add up to 0.25% more. On a $500,000 sale, that's roughly $3,750 to the state and $1,250 to the town.
- The federal home-sale exclusion. Did you own and live in the house as your main home for two of the last five years? Then you can generally exclude up to $250,000 of gain, or $500,000 if you're married filing jointly. IRS Publication 523 on selling your home explains the rules. If you move first and sell later, ask your CPA how long you can wait and still qualify.
- Connecticut still taxes a Connecticut sale. Florida has no state personal income tax, but that doesn't erase Connecticut's claim on a Connecticut house. Nonresidents still owe Connecticut income tax on any taxable gain from selling Connecticut real estate, reported on a nonresident or part-year return (Form CT-1040NR/PY). Connecticut generally taxes only the gain that the federal exclusion doesn't cover. Connecticut's top income-tax rate is 6.99%.
Plan the Closing — Even If You're Already Gone
You may not need to fly back to Connecticut to close. In many cases, sellers sign their documents ahead of time with a notary where they live, and their closing attorney handles the rest — ask yours what's possible in your situation. Our guide to selling a Connecticut house while you live out of state walks through the mechanics of a remote closing.
The bigger job is usually the house itself: decades of belongings, a basement you haven't seen the floor of in years, repairs you never got around to. With a cash sale, you don't have to fix anything or clean anything before you go. Helpful Home Buyers buys houses in any condition, so if you'd rather sell your house as-is for cash, you can pack what matters to you and skip the repairs, the cleaning and the showings.
If your house is in Trumbull or nearby, you're in familiar territory for Dan and Meghan — they restored the historic Daniel Hawley House in Trumbull, and they buy homes throughout the area. Here's how selling your house in Trumbull works with a local buyer.
Set Up Your New Home's Tax Breaks Before You Need Them
Florida has no state personal income tax, which is a big part of its pull. Property taxes still apply there, but Florida gives homeowners two important protections.
- The homestead exemption. Florida's homestead exemption can reduce your home's taxable value by up to about $50,000, and part of that amount now rises with inflation each year. To get it for a given year, you generally must own the home and make it your permanent residence by January 1. Then you file with your county property appraiser by March 1, according to the Florida Department of Revenue's homestead guide. That makes your closing and moving dates matter.
- Save Our Homes. Once your Florida home has a homestead exemption, Save Our Homes caps the yearly increase in its assessed value at 3% or the change in the Consumer Price Index, whichever is lower.
Here's why the calendar matters. If you buy your Florida home and make it your permanent residence by January 1, you can apply for that coming year's exemption by March 1. If you move in on January 15 instead, you generally wait until the following year — so a Connecticut closing date you control can be worth real money down south.
Florida voters approved Amendment 3 on November 3, 2026. It raises the homestead exemption from non-school property taxes to $150,000 in 2027 and $250,000 in 2028. People who become Florida residents in 2027 or later start at about $50,000, though, and get the larger amount only in their fifth year with a homestead exemption.
Heading to North or South Carolina instead? The rules there are different, so talk to a tax professional in your new state before you buy.
Why a Firm Closing Date Makes the Whole Plan Easier
Every step above gets easier when one date stops moving. With a traditional listing, your closing depends on showings, a buyer's mortgage approval, an appraisal and an inspection — any of which can push the date or end the deal. With a cash sale, there's no buyer's lender to wait on.
Helpful Home Buyers gives you a written, no-obligation cash offer within 24 hours of one walkthrough. You pick the closing date — in as little as about 10 days, or later if you need time to close on your new home. And if you're 65 or older and still deciding whether to go at all, compare your senior property tax relief options in Connecticut first.
Your Order of Operations, Start to Finish
Here's one sequence that keeps the move simple:
- Step 1 — Get your number. Ask for a written offer on your Connecticut house so you know what you'll have to spend before you shop.
- Step 2 — Talk to your CPA. Confirm the exclusion, the conveyance tax and any Connecticut tax on the gain.
- Step 3 — Shop with confidence. Make your offer down south knowing your budget and your timeline.
- Step 4 — Line up both closings. Pick a Connecticut closing date that fits your new home's closing, and sign remotely if you're already gone.
- Step 5 — Claim your new tax breaks. Make your new home your permanent residence and file for Florida's homestead exemption by March 1.
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One Closing Date You Control — From Wherever You Are
You've planned this move for a while. Let the house be the easy part. Get your written cash offer from Helpful Home Buyers, line up the closing with your new home, and head south knowing exactly what you're walking away with.
