For decades, Boston has been one of the most desirable cities in the Northeast — full of history, culture, and opportunity. But in recent years, more and more Bostonians have been asking themselves a big question: Is it time to move south?
Between rising housing costs, long winters, and high taxes, many Boston residents are leaving for St. Augustine, FL — a city that offers coastal charm, historic beauty, and a slower, sunnier pace of life.
If you’ve been wondering what’s driving this migration, or whether living in St. Augustine Florida could be right for you, let’s break it down.
1. Escaping High Costs and Harsh Winters
Boston is beautiful, but it’s not cheap.
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Housing: The median home price in the Greater Boston area now exceeds $750,000–$800,000, making it one of the most expensive housing markets in the country.
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Taxes: Massachusetts’ income tax and high property taxes add up fast.
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Weather: Long winters and heavy snow mean higher heating bills and months spent indoors.
In contrast, St. Augustine real estate offers a coastal lifestyle that’s both affordable and comfortable. Median home prices in St. Johns County Florida typically fall between $400,000–$500,000, depending on the neighborhood, with no state income tax and lower property taxes.
👉 For Boston homeowners cashing out at peak value, moving to St. Augustine FL can mean upgrading to a larger home or downsizing debt-free — all while gaining sunshine and space.
2. Lifestyle: From Fast-Paced to Laid-Back Coastal Living
Boston’s energy is unmatched — but so is its traffic and pace. Life in St. Augustine Florida offers a refreshing shift.
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Mornings: Grab coffee downtown or walk the beach instead of scraping ice off your windshield.
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Weekends: Trade snow shoveling for kayaking, boating, or exploring local markets and festivals.
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Evenings: Enjoy dinner al fresco in historic downtown or sunset walks along the Intracoastal.
Here, living in St. Augustine FL means sunshine year-round and time to actually enjoy it.
3. Community and Culture
Boston and St. Augustine share one big thing: history. But while Boston is urban and fast-moving, St. Augustine FL blends its 450+ years of history with a relaxed, coastal lifestyle.
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Historic Downtown: Cobblestone streets, live music, and centuries-old architecture.
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Neighborhood Variety: From the beachy vibe of Anastasia Island to family-friendly World Golf Village, every area offers its own charm.
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Community Feel: Neighbors know each other. Festivals, art walks, and farmers markets bring locals together.
If you’re wondering where to live in St. Augustine Florida, popular spots include Lincolnville, Palencia, and Vilano Beach — all among the best neighborhoods to live in St. Augustine Florida.
4. Jobs, Remote Work, and Retirement Appeal
Since the pandemic, remote work has opened the door for many Boston professionals to live where they want, not where their jobs are located. Moving to St. Augustine Florida allows them to enjoy a better quality of life without sacrificing career flexibility.
For retirees, the draw is even stronger:
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Lower taxes and cost of living.
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Top-rated healthcare access in St. Johns County Florida.
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A thriving social scene with golf, beaches, and community events year-round.
5. The Real Estate Advantage
Boston’s real estate market is competitive and high-priced, but St. Augustine real estate offers far more flexibility and value.
Buyers can choose from:
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Historic homes in downtown St. Augustine.
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New construction in family-friendly neighborhoods.
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Waterfront properties along the Intracoastal or near the beach.
With inventory growing and homes staying on the market longer, it’s an ideal time for relocation buyers to explore where to live in St. Augustine FL before the next market upswing.
FAQs About Moving from Boston to St. Augustine
Is St. Augustine a good fit for former Bostonians?
Absolutely. The blend of history, coastal living, and affordability makes it a natural transition for Boston residents who want a similar charm — without the snow.
What’s the weather like compared to Boston?
Expect sunshine most days, mild winters, and humid summers — but no snow shoveling!
What about schools?
Families will love St. Johns County Florida, consistently rated one of the top school districts in the state.
Conclusion
So, why are Boston residents leaving for St. Augustine Florida? The answer is simple: better weather, lower costs, and a lifestyle that feels like a permanent vacation.
Whether you’re a retiree, a remote worker, or a family looking for more balance, St. Augustine FL offers it all — history, culture, beaches, and community.
👉 Thinking about moving to St. Augustine FL? Contact Kim Devlin, your trusted Realtor in St. Augustine, to explore the best neighborhoods to live in St. Augustine Florida and discover why so many Northeasterners are calling this coastal gem home.