By Eric Berman, REALTOR® | The Eric Berman Team at Compass
TL;DR:
The transaction that determines how a Long Island to Connecticut move goes is the one on this end — the sale that sets the budget and the timeline. On the destination side, the most common assumption to check is property taxes: Connecticut assesses through municipal mill rates that vary enormously town to town, so whether a specific Connecticut property beats a specific Nassau one is a question about two tax bills rather than two states. Two things make this particular move easier than it looks. Both states require attorney involvement in residential closings, so the process is familiar on both ends. And the ferries — Port Jefferson to Bridgeport, Orient Point to New London — are a real option that most planning overlooks.
The Sale Comes First
Most people plan this move from the Connecticut end, because looking at listings is more engaging than building a spreadsheet. The order should run the other way.
The Long Island sale sets the budget, determines when funds are available, and decides whether the family moves on their own schedule or someone else's. Before touring anything across the Sound, a seller should know what the current home realistically sells for and what actually remains after costs.
That model needs the full picture — commission, New York State Transfer Tax at four dollars per thousand, attorney fees generally $1,500 to $3,500, preparation spending, and carrying costs for a listing period longer than hoped. The full breakdown of what a Long Island sale costs walks through each line.
One item specific to this move. A seller who establishes Connecticut residency before the Long Island closing becomes a New York nonresident for that transaction, which triggers Form IT-2663 — an estimated payment at closing of 8.82 percent of net gain. It is not an additional tax but a prepayment against actual New York liability, refundable where the real number comes in lower. It does reduce the wire, which catches people who have already committed those funds to a Connecticut purchase.
The Property Tax Question, Answered Honestly
The most common assumption about this move is that Connecticut brings property tax relief. It sometimes does and sometimes does not, and the reason is structural.
Connecticut assesses property taxes through municipal mill rates set town by town, and the spread across the state is wide. Some towns in lower Fairfield County carry notably low mill rates on high property values; several Connecticut cities carry among the highest mill rates in the state. There is no Connecticut-wide answer, and any source offering one is generalizing past the point of usefulness.
The comparison that means something is between two specific properties: the actual current tax bill on the Long Island home being sold, against the actual current bill on the Connecticut property under consideration. Portal estimates are frequently stale. Pull the real figures from the town's assessor and put the difference — in either direction — into the monthly budget before making an offer.
Worth noting alongside this: Connecticut imposes its own state income tax, and the interaction between New York and Connecticut taxation in a year when someone moves between them is a genuine question rather than a formality. That belongs with a CPA before the move rather than at filing time.
Getting There, Including the Option Most People Miss
By car, the route runs across the Throgs Neck or Whitestone Bridge into the Bronx, then north and east via I-95 or the Hutchinson River Parkway. Those bridges are the first leg rather than the crossing itself, which is a distinction the planning often gets wrong.
The option most Long Island households overlook is the water. Two vehicle ferries cross the Sound: Port Jefferson to Bridgeport, and Orient Point to New London. For a move originating on the North Shore or further east, either can be faster and considerably less unpleasant than driving around through the Bronx — and for households making repeated trips during a search, the difference compounds. Worth pricing and scheduling as part of the plan rather than discovering afterward.
On commuting, Connecticut runs on Metro-North's New Haven line, which serves the Fairfield County towns along the coast into Grand Central. Trip times vary substantially by station, with the towns closest to the New York line considerably faster than points north and east. The reliable approach is the same as anywhere: ride the actual train, from the actual station, at the actual hour, before committing to a town — and add the door-to-door pieces, since the drive to the station and the walk at the Manhattan end frequently add twenty to thirty minutes each way.
What Stays Familiar
One genuine advantage of this move over most: both states require attorney involvement in residential real estate closings.
In New York, contract drafting and negotiation are legal work reserved to licensed attorneys, and the attorney coordinates the title search and payoff and runs the closing. Connecticut operates on the same principle. A household selling on Long Island and buying in Connecticut will therefore have counsel on both ends of the move, working within a process that looks broadly similar — which is a meaningfully different experience from moving to a state where a title or escrow company drives the transaction. The fuller picture of what the attorney handles applies on the New York side.
Two attorneys are required rather than one, since the licensing is state-specific. Worth asking the New York attorney for a Connecticut referral, since attorneys who handle relocations often have working relationships across the line.
On the Connecticut side, transaction costs differ from New York's. Connecticut imposes conveyance taxes at both the state and municipal level, paid by the seller — which means they do not affect this purchase but will affect the eventual resale. Rates vary by municipality and by price. A Connecticut attorney or agent should confirm the specifics for any town under consideration.
The Sequencing Problem
This is the hardest part of any two-transaction move and it deserves more attention than destination research.
Long Island runs on a ten percent deposit held in attorney escrow, well above the national norm. Connecticut conventions differ and should be confirmed, but a purchase deposit will be due at contract signing regardless — potentially while the Long Island home is still listed or under contract but not closed.
Three approaches, each with a cost. Sell first: cleanest funds and the strongest negotiating position on the purchase, since the offer carries no contingency on another sale, but it may require temporary housing and a second move. Buy first: avoids interim housing but means carrying both properties, frequently $12,000 to $16,000 monthly combined at Long Island price points, which pressures the sale toward accepting less. Coordinate simultaneous closings: ideal when it works, fragile when anything surfaces in either title search.
What most often breaks the third option is something on the Long Island side — an unclosed permit, an old undischarged lien, a certificate of occupancy that does not match the house. Those surface in municipal searches weeks after contracts are signed. Calling the town or village building department before listing is the single most effective way to protect a coordinated timeline, and it costs nothing.
A Worked Example
Consider a composite case — a North Shore Nassau household relocating for a Stamford-area job, selling a colonial that comped near $1,220,000 and looking in Connecticut around $1,100,000.
Their working assumption was tax relief. Pulling actual bills complicated it: their Nassau bill ran roughly $20,100, and the Connecticut properties they liked ranged from about $16,000 to $24,000 depending on the town. A saving in some cases, an increase in others, entirely dependent on which town — not on which state.
They went sell-first. Their New York attorney ran an early title review that turned up a 2014 permit for a finished basement never closed out, resolved in about five weeks before listing. The same attorney referred them to a Connecticut attorney for the purchase side.
For the search itself, they used the Port Jefferson ferry rather than driving around through the Bronx, which cut roughly ninety minutes off each round trip during a search that ran most weekends for two months. They closed the Long Island sale in spring, spent six weeks in a short-term rental, and bought with cash in hand and no sale contingency.
Where to Start
Get a real number on the Long Island home and build the net-proceeds model before touring anything. Call the town or village building department and ask what permits and violations are on file. Engage a New York real estate attorney early and ask for a Connecticut referral. Pull actual tax bills on both ends and compare property to property rather than state to state. Talk to a CPA about the residency and IT-2663 questions before the move rather than after. Ride the Metro-North line for any town under serious consideration. And price the ferries — they may change how the search itself works.
Sellers wanting a current read on where their Long Island home sits can start with a quiet look at present value, and more market and process coverage lives in Local Insights.
The Honest Bottom Line
The move is more manageable than a cross-country relocation and less different than it feels. Both ends require attorneys, both markets run on comparable transaction mechanics, and the physical distance is short enough that a ferry crossing handles it.
What causes trouble is the assumption that Connecticut is categorically cheaper on taxes. Some towns are, some are not, and the only comparison worth making is between two actual bills. Households that run that arithmetic honestly, sell first, and check their permits before listing tend to find the whole thing straightforward.
For anyone working through what their Long Island home would actually net before any of the Connecticut decisions get made, that conversation is available whenever the timing is right, with no pressure attached.
This is general information, not legal, tax, or financial advice. Connecticut property tax structures, conveyance taxes, and transaction requirements vary by municipality and change over time, and should be confirmed with a Connecticut attorney or agent. New York specifics should be confirmed with a licensed New York real estate attorney and a CPA.
FAQs
Are property taxes lower in Connecticut than on Long Island?
Sometimes, and the answer depends entirely on the specific town rather than the state. Connecticut assesses through municipal mill rates set town by town, and the spread across the state is wide — some lower Fairfield County towns carry notably low rates, while several Connecticut cities carry among the highest. There is no statewide answer. The comparison that matters is between the actual current tax bill on the Long Island property being sold and the actual current bill on the Connecticut property under consideration, pulled from the town assessor rather than from a listing portal.
How do you get from Long Island to Connecticut?
By car, across the Throgs Neck or Whitestone Bridge into the Bronx, then north and east via I-95 or the Hutchinson River Parkway — those bridges are the first leg rather than the crossing itself. The option most households overlook is the water: two vehicle ferries cross the Sound, Port Jefferson to Bridgeport and Orient Point to New London. For a move originating on the North Shore or further east, either can be faster than driving around, and for repeated trips during a house search the difference adds up considerably.
Does Connecticut require an attorney for a home purchase?
Yes, which makes this move easier than many. Both New York and Connecticut require attorney involvement in residential real estate closings, so a household selling on Long Island and buying in Connecticut will have counsel on both ends working within broadly similar processes. That differs meaningfully from relocating to a state where a title or escrow company drives the transaction. Two attorneys are needed rather than one, since licensing is state-specific — and a New York attorney who handles relocations can often provide a Connecticut referral.
What is Form IT-2663 and does it apply to this move?
It applies if the Long Island home sells after the seller has established Connecticut residency. New York requires nonresident sellers to make an estimated payment at closing of 8.82 percent of net gain, filed through Form IT-2663. It is not an additional tax — it is a prepayment against actual New York State income tax liability, refunded when the return is filed if the real number comes in lower. It matters practically because it reduces the amount wired at closing, which catches sellers who have already committed those proceeds to a Connecticut purchase.
Should I sell my Long Island home before buying in Connecticut?
It depends on cash position and risk tolerance. Selling first produces clean funds and a stronger negotiating position, since the Connecticut offer carries no contingency on another sale — but it may require temporary housing and a second move. Buying first avoids that while meaning the household carries both properties, frequently $12,000 to $16,000 monthly combined at Long Island price points, which pressures the sale toward accepting less. Coordinating simultaneous closings works well when nothing surfaces in either title search and poorly when something does.
By Eric Berman, REALTOR® | The Eric Berman Team at Compass
Eric Berman | Long Island & Queens Associate Broker | Compass
1468 Northern Blvd, Manhasset, NY 11030
(917) 225-8596 | eric@ericbermanre.com | theericbermanteam.com
