Thinking of Leaving Westport, CT?
Ben Bryk March 29, 2026
Ben Bryk March 29, 2026
By Ben Bryk & Vance Brinkerhoff · Coldwell Banker Global Luxury · Vero Beach, Florida
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WHO WROTE THIS Ben Bryk (772-713-9455) & Vance Brinkerhoff (772-913-3426)Between us, we've been selling real estate in Vero Beach for over 35 years. We've closed more than 2,000 deals and worked with a lot of Westport, Greenwich, New Canaan, and Fairfield County families. Apple News named us among Florida's Top 10 Most Trusted Agents in 2025. We know this market, and we know what Connecticut buyers need to hear before they make this move. |
We get calls from Westport families every single week. And they usually start the same way — somewhere between "we've been thinking about this for a while" and "our accountant finally sat us down and made us look at the numbers." Sometimes it starts with a winter that broke them. Sometimes it starts with a grandchild born in Florida. Sometimes it's just the tax bill in April that pushes it over the edge.
Whatever brought you here, we're glad you're reading this. Because the version of this story you get from a real estate marketing brochure and the version you get from two guys who have done this 2,000 times are pretty different. This is the second version.
Westport is a great town. We know that. Compo Beach, the Westport Country Playhouse, the schools, the restaurants on Main Street, the community — it's genuinely good. We're not trying to talk you out of loving Westport. We're just going to tell you what it looks like on the other side.
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"The people who make this move almost never regret it. The ones who wait? They call us five years later and say they wish they hadn't." |
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THE WESTPORT EQUITY SITUATION If you own a home in Westport — particularly Old Hill, Greens Farms, or anywhere near Compo Beach Road — you are probably sitting on somewhere between $1 million and $3 million in equity. Possibly more. That's real money. And right now, a big chunk of what that equity generates is going to Hartford every April. When you take that equity to Vero Beach, two things happen at once: you buy significantly more house for significantly less money, and you stop paying Connecticut income tax. We've seen people go from writing a $75,000 check to the state to writing a $0 check. That's not a rounding error. That changes how you live. |
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📊 THE NUMBERS Connecticut's top marginal income tax rate is 6.99% (CT Department of Revenue Services, 2024). Florida's is 0% — written into the state constitution. For a Westport household earning $600,000 a year, that's roughly $41,940 annually. Add in estate tax savings and property tax differences, and you're looking at $60,000+ per year, every year. That's a boat. That's a trip to Europe every year. That's real money compounding over a decade. |
People usually know about the income tax thing. What they often miss are the other two pieces — and together, all three add up to something that any good financial advisor will tell you is worth paying serious attention to. The Tax Foundation consistently ranks Connecticut among the five highest-tax states in the country. Florida is near the bottom.
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🏛️ No State Income Tax Florida's constitution bans it. Connecticut charges up to 6.99%. On $750K that's $52,000 a year you keep. Every year. Forever. |
🏡 No Estate Tax + Homestead Cap Connecticut's estate tax hits above $2M — which captures most Westport homes. Florida has zero. Plus a 3% annual property tax increase cap via Homestead. |
💼 SALT Cap Relief Westport's high property taxes are almost completely undeductible under the $10K federal SALT cap. Florida's lower taxes mean you stop losing money on a cap you were never going to beat anyway. |
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ESTIMATED ANNUAL TAX SAVINGS $60,000+Westport Household Earning $600K+ *Based on CT vs. FL income tax, estate planning, and property tax differences. Sources: Florida Dept. of Revenue; CT DRS 2024. Talk to your CPA about your specific situation. |
Here's the mistake we see over and over: someone falls in love with a house in Vero Beach before they've set their Westport sale up properly. They move fast on the Florida side, and then they're under pressure on the Connecticut side. They take an offer they shouldn't. They make a hasty decision down here. We've watched it happen, and it's painful.
The way we do it is different. When you call us, we immediately connect you with the best Coldwell Banker agent in Westport — someone who knows your market cold and will push hard to get you top dollar. While that's happening, we're working the Vero Beach side. The two transactions run in parallel, and we're coordinating the timing so you're not scrambling at the end.
Beyond the real estate, we've built out what we call a Financial Concierge Desk — a network of professionals we've worked with for years who handle the rest of what this move requires.
THE VERO PREMIER CONCIERGE NETWORK — PEOPLE WE CONNECT YOU WITH:
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The goal is that you make one call to us, and we handle the rest.
The number one thing Westport families worry about is staying connected. To New York, to family, to everything they've built. We hear it all the time: "We'd love to do this, but we can't be that far from the city."
Here's the thing — Westchester Airport is about 20 minutes from Westport, where Breeze Airways has direct service down here as well. Most of our Westport clients are wheels-down in Vero Beach in under three hours from their front door. Compare that to the MetroNorth commute most of them were already making.
✈️ YOUR OPTIONS TO GET HERE
One of our clients told us recently she sees her kids in the city more now than when she lived in Westport, because the flight made her actually go rather than dreading the drive. That surprised her. It shouldn't have — we hear it a lot. |
Grand Harbor Golf & Beach Club — Vero Beach, Florida
This is the part we like talking about most, because the gap between what people expect and what they find is usually pretty significant — in a good way.
They golf — a lot. They're on the water constantly, whether that's a boat, paddleboarding, or just sitting on the beach. They go to the farmers market on Saturday mornings and run into the same people every week, which starts to feel like the best parts of home without the ice and the commute. They go to the Vero Beach Museum of Art, which genuinely impresses people who expected less. They eat well. And most of them — honestly, most of them — spend the first year slightly stunned that January 15th is 72 degrees and sunny.
What Vero Beach is not: it's not Miami. It's quiet when you want quiet. It doesn't have the tourist noise or the spring break crowds or the traffic. It's a real town full of people who chose to be here — a lot of them from Connecticut, honestly. That particular mix tends to work well for Westport people.
VERO BEACH MUSEUM OF ART
Genuinely world-class, and it surprises almost everyone. Rotating major exhibitions, a permanent collection, lectures, and galas throughout the season. Not what people expect from a town this size.
RIVERSIDE THEATRE
Professional productions, not community theater. The same quality you'd drive to the city for — except it's ten minutes away and you don't have to fight for parking.
THE RESTAURANT SCENE
Better than you'd expect, and growing. Oceanfront fine dining sits alongside local fish shacks that have been around for forty years. Both are good. Our clients use both.
POLO & EQUESTRIAN AT WINDSOR
If you've been to Greenwich Polo Club, you know this world. Windsor does it at a level that draws an international crowd. For Westport families with an equestrian connection, this is often the thing that seals the deal.
SATURDAY FARMERS MARKET
Fresh citrus off local groves, local honey, craft vendors. This sounds small, but it's one of the things our clients mention most. There's a community rhythm to it that feels familiar.
THE WATER & THE BEACH
26 miles of Atlantic coastline with no crowds. Sea turtle nesting season. Kayaking on the Indian River Lagoon. The beach is never more than a few minutes away, and it's rarely busy. That part never gets old.
This is the part of the conversation that tends to change people's thinking most. We've shown this comparison to dozens of Westport families and the reaction is almost always the same: a long pause, and then "why didn't we know about this?"
What your Westport equity would buy you in Palm Beach is a two-bedroom condo and a parking spot. What it buys you in Vero Beach is a waterfront estate, a boat dock, a golf membership, and beach club access — with money left over. That is not an exaggeration. We've watched it happen dozens of times.
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📊 SOURCE: 2024–2025 Zillow Research, Redfin Market Reports & Indian River County Property Appraiser. Real sold prices, not list prices. |
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MARKET |
AVG. LUXURY HOME |
PRICE / SQ. FT. |
VS. VERO BEACH |
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Palm Beach |
$6M – $25M+ |
$1,800 – $4,500 |
🔴 3–5× more |
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Naples |
$3M – $12M |
$900 – $2,200 |
🟠 2–3× more |
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Miami / Coral Gables |
$2.5M – $15M+ |
$800 – $3,000 |
🟠 2–4× more |
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✦ Vero Beach |
$800K – $4M |
$350 – $900 |
🟢 Best Value |
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★ Vero Beach delivers the same luxury lifestyle for 40–70% less than Palm Beach, Naples, or Miami ★ |
Vero Beach has real range. Different people want different things, and we've placed families in all of these communities. Here's our honest read on each one.
GOLF & BEACH CLUBGrand Harbor Probably where we send the most Westport families first. Two good golf courses, a private beach club on the Atlantic, tennis, a marina on the Indian River. Active, friendly, well-run. If you belong to Longshore or Weston Golf Club, the transition here will feel natural. |
ULTRA-EXCLUSIVE OCEANFRONTJohn's Island Three golf courses, a private beach, and invitation-only membership. The most exclusive club community in Vero Beach — arguably in all of Florida. The membership tends to resonate with people who are used to that level of exclusivity at home. |
BARRIER ISLAND WATERFRONTOrchid Island Oceanfront and intracoastal estates with deep-water dockage and championship golf. For Tokeneke families who love waterfront living and want to translate that feel to Florida, Orchid Island is often the answer. |
POLO & EQUESTRIANWindsor Designed by Andrés Duany. World-class polo, equestrian facilities, beautiful architecture. Not for everyone — but for the right person with an equestrian connection, it's hard to walk away from. |
BARRIER ISLAND NEIGHBORHOODThe Moorings & Castaway Cove Some of Vero Beach's most beloved addresses. Oceanfront and intracoastal homes, a tight community, and a neighborhood feel that people from Westport recognize immediately. |
NEW CONSTRUCTIONQuay Village & The Reserve Modern finishes, smart home technology, nothing to fix when you move in. A growing number of Connecticut buyers are choosing turnkey over renovation, and these communities deliver that cleanly. |
35+YEARS COMBINED EXPERIENCE |
2,000+TRANSACTIONS CLOSED |
$1B+IN SALES VOLUME |
Apple News · Top 10 Most Trusted Agents in Florida — 2025
Ben Bryk & Vance Brinkerhoff — 35+ years, 2,000+ transactions, $1B+ in sales volume
We've been doing this in Vero Beach for 35 years between us, and we've worked with enough Westport families to understand what matters to you — and what you're worried about. We're not going to pressure you. We're going to give you a real picture of what this looks like, answer your questions honestly, and if it makes sense for your family, we'll handle the whole thing so it's as smooth as it can be. If you're just curious and not ready to decide anything, that's fine too. Call us. We talk to people at every stage of this all the time.
Real answers, no fluff.
Q: How much would we actually save on taxes by moving to Florida?
For a Westport household earning $600,000 a year, you're typically looking at $60,000 or more in annual savings. That's the income tax difference alone (Connecticut 6.99% vs. Florida 0%), plus estate tax advantages — Connecticut taxes estates above $2 million, Florida has none — plus the property tax gap. The exact number depends on your situation, so we always say talk to your CPA. But we've never had a client who ran the numbers and wasn't impressed.
Q: What does our Westport home equity actually buy in Vero Beach?
A lot more than most people expect. At current Vero Beach prices — $350 to $900 per square foot depending on the community — equity from a Westport sale typically buys a real luxury home — often with waterfront access, golf course views, or private club membership included. In Palm Beach, that same $2 million buys you a two-bedroom condo without club access. We've had Westport clients arrive in Vero Beach genuinely stunned at what their equity purchased. That reaction is very common.
Q: How do we fly from Westport to Vero Beach?
Westchester Airport is about 20 minutes from Westport, and Breeze Airways has direct service from there to the Vero Beach area. No going into the city, no JFK, no hassle. If you do want to fly JetBlue, they run daily nonstop flights from JFK directly to Vero Beach Regional Airport. Most of our Westport clients are door-to-door in under three hours. It's genuinely not a big trip.
Q: Is Vero Beach going to feel anything like Westport?
More than you'd expect. Vero Beach is a small, tight-knit community of people who mostly chose to be here deliberately. There's a real arts scene, good restaurants, Saturday farmers markets, polo and equestrian culture, and neighbors who have things in common with you. The Westport Country Playhouse crowd tends to feel immediately at home at Riverside Theatre. The beach culture is different from Compo Beach, but the underlying community feeling — accomplished, private, unpretentious — is familiar. And the tax bill is dramatically different.
Q: What's the deal with Florida's estate tax versus Connecticut's?
Connecticut imposes an estate tax on estates above $2 million, with rates going up to 12%. Florida has no estate tax at all. For most Westport families — especially those with a home, investment accounts, and other assets — this is not a small difference. It can represent hundreds of thousands of dollars in multigenerational wealth that either goes to your family or goes to Hartford. We connect every client with a Florida estate attorney to make sure the domicile change is set up correctly from day one.
Q: How is Grand Harbor different from John's Island? Which one is right for us?
Grand Harbor is more social and approachable — two golf courses, a beach club, a marina, tennis, pickleball, lots of activity. It tends to attract people who want a full-service club community where they'll actually get to know their neighbors. John's Island is more exclusive, more private, more formal in some ways — three golf courses, a private beach, invitation-only membership. If you belong to Longshore or Weston Golf Club, you'll feel at home in either. Call us and we'll talk through which fits your lifestyle better.
Q: Can you really handle both the Westport sale and the Vero Beach purchase at the same time?
Yes, and this is honestly the most valuable thing we do for Westport clients. We connect you with our top Coldwell Banker partner in Westport who knows your area well and will maximize your sale price while we handle the Florida side. We stay in communication on both ends and coordinate the timing so you're not stuck owning two houses or scrambling to close fast. We've done this hundreds of times. It works, and it removes most of the stress people associate with making a major move.
Q: What does establishing Florida domicile actually involve?
The basics: file a Florida Declaration of Domicile, get a Florida driver's license and vehicle registration, register to vote in Florida, and spend more than 183 days per year here. You also need to update your estate documents under Florida law. Connecticut used to audit this aggressively — they still do — so it's important to do it right. Our Concierge Desk connects you with attorneys who specialize in this for high-net-worth Northeastern clients. We've seen the shortcuts blow up on people. Don't take shortcuts.
Q: What's Orchid Island like for Westport waterfront families?
Orchid Island tends to resonate most with Westport families who have a strong waterfront identity — people who love Compo Beach, who have always had a boat, who define their lifestyle around the water. It's a barrier island community with oceanfront and intracoastal estates, deep-water dockage, and the kind of privacy and natural setting that's hard to find in Florida at any price. We've moved several Compo Beach area families to Orchid Island and the fit has been consistently good.
Q: Is the Vero Beach luxury market competitive right now?
Yes — particularly at the top end. Good homes in John's Island, Grand Harbor, and Orchid Island move fast. We're still seeing strong demand driven by Northeastern in-migration, and inventory in the most desirable communities is tight. This is not the market to take your time in if you find the right property. Having a local agent who knows what's coming before it hits the market makes a real difference. That's a significant part of what we offer.
Q: What's the weather actually like — honestly?
January average high in Vero Beach: 72°F. In Westport: around 38°F. Vero Beach gets about 230 sunny days a year. Summers are warm and humid with afternoon thunderstorms — you learn to schedule your outdoor time in the morning. The honest answer is that the weather is wonderful for nine or ten months of the year, and manageable for the other two. Most people who move here can't believe they waited as long as they did.
Q: What about private schools for our kids?
St. Edward's School in Vero Beach is the local independent option — solid academic reputation, good athletics, and a real college prep program. For families who want more, Palm Beach County's top schools (The Benjamin School, Palm Beach Day Academy) are within 45–60 minutes. We help families with school introductions as part of our relocation support. It's one of the first conversations we have with families who are still in the school-age years.
Q: Is Vero Beach really better than Palm Beach or Naples for value?
On a pure value basis, it's not close. Palm Beach averages $1,800–$4,500 per square foot for luxury properties. Vero Beach averages $350–$900. You're getting equivalent club amenities, better privacy, and a dramatically less congested lifestyle for 40–70% less money. The people who choose Palm Beach are often choosing a name. The people who choose Vero Beach are choosing the actual experience. Both are valid — but we're biased, obviously.
Q: How far is Vero Beach from Miami and Palm Beach?
About an hour north of West Palm Beach, two and a half to three hours north of Miami. Close enough for day trips and airport access, far enough that you don't deal with any of the South Florida chaos. Most of our clients consider this distance to be one of Vero Beach's best features — not a drawback.
Q: Why should we work with you instead of a local Florida agent we find online?
That's a fair question and we'd rather earn your trust than just claim it. Here's the honest case: we've done this specifically — Northeastern families moving to Vero Beach — for 35 years. We've closed over 2,000 transactions and more than a billion dollars in sales. We know the inventory before it lists, we know the communities deeply, and we can coordinate your Westport sale simultaneously with a trusted Coldwell Banker partner up north. A local Florida agent you find online can show you houses. We run the whole transition. Those are different things. We've closed over 2,000 transactions and more than a billion dollars in sales. Apple News named us among Florida's Top 10 Most Trusted Agents in 2025. But more than any of that — call us, talk to us, and see if we're the right fit. If we're not, we'll tell you. Ben: 772-713-9455. Vance: 772-913-3426.
Call Us. We'll Give You the Honest Picture.No pressure, no pitch. Just a real conversation about whether this makes sense for your family. We pick up the phone. BEN BRYK · VERO PREMIER PROPERTIES772-713-9455 VANCE BRINKERHOFF · VERO PREMIER PROPERTIES772-913-3426 floridaeastcoastluxuryhomes.com |
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