By Sal DiBenedetto, Licensed Real Estate Broker · The DiBe Group, brokered by eXp Realty · Updated October 2026

Maryland has a long tradition of sending retirees, snowbirds and families south to Florida, and Southwest Florida has become one of the favorite destinations. Recent changes in Maryland’s tax code, including new top income tax brackets and a capital gains surcharge for higher earners, have given many Marylanders one more reason to look at Florida, which has no state income tax, no estate tax and no inheritance tax.

This guide is written for people moving from anywhere in Maryland, from Baltimore and Annapolis to Montgomery County, Howard County, Frederick and the Eastern Shore. It covers the tax differences in detail, what you can expect to pay for a home in Estero, how insurance and everyday costs compare, the easiest ways to make the trip and what daily life feels like once you arrive.

Maryland vs. Estero at a Glance

Maryland Taxes vs. Florida: The Big Picture

State and County Income Taxes

Maryland taxes income at the state level with rates that top out at 6.25% on income between $500,000 and $1 million for single filers ($600,000 to $1.2 million for joint filers) and 6.5% above that, under brackets that took effect for tax year 2025. On top of the state tax, every Maryland county and Baltimore City levies a local income tax. For 2026, local rates range from about 2.25% to 3.20%, with Baltimore City, Baltimore County, Howard County and Prince George’s County at the top of that range. Montgomery and Anne Arundel counties use graduated local rates.

Combined, many Maryland households pay 7% to 9% or more of their income in state and local income tax. Florida has neither. That applies to wages, pensions, IRA and 401(k) distributions, investment income and Social Security.

Capital Gains Surcharge

Starting with tax year 2025, Maryland added a 2% surcharge on net capital gains for taxpayers with federal adjusted gross income above $350,000, with an exception for the sale of a primary residence under $1.5 million. Investors, business owners and anyone planning to sell a large asset should talk to a tax advisor about the timing of their move.

Estate and Inheritance Tax

Maryland is one of the few states with both an estate tax and an inheritance tax. The estate tax applies to estates above a $5 million exemption, with rates up to 16%. The inheritance tax is 10% on assets left to heirs who are not exempt, such as nieces, nephews and friends; spouses, children, grandchildren and siblings are exempt. Florida has no estate tax and no inheritance tax, which can make a meaningful difference in estate planning for many families.

Sales and Property Taxes

Maryland’s sales tax is 6% statewide, with no local sales tax, and a new 3% tax on certain IT and data services took effect in July 2025. In Estero, the combined sales tax is 6.5%. Maryland’s average effective property tax rate is about 0.90%, compared with about 0.76% in Florida. Florida also offers a homestead exemption of up to about $50,000 off the assessed value of a primary home and caps annual assessment increases at 3% for homesteaded properties.

This is general information, not tax or legal advice. Rates can change; consult a CPA or estate attorney familiar with Maryland and Florida.

Car Insurance and Everyday Costs

Here is a surprise for many Marylanders: car insurance may go down. According to Insurify, Maryland drivers paid an average of about $302 a month for full coverage in 2026, the highest in the country, compared with about $236 a month in Florida. Gas prices are similar, about $4.37 a gallon in both states in late September 2026.

Homeowners insurance is a different story. Florida’s average homeowners premium was about $3,023 a year in early 2025, according to state regulators, which is higher than what many Maryland homeowners pay. Your actual cost depends on the age of the roof, windows, construction and flood zone. Newer homes built to modern Florida Building Code standards, with impact windows and newer roofs, are much less expensive to insure. Flood insurance is separate and is required in many flood zones with a mortgage.

• No heating bills: Say goodbye to oil, gas or heat pump bills in January. Florida’s higher electric bills come in summer from air conditioning.
• No snow removal: No shovels, plows, salt or snow tires.
• HOA fees: Many Estero homes are in gated communities with HOA dues that cover amenities, landscaping and security.
• Vehicle registration: Florida charges a one-time $225 initial registration fee for vehicles new to the state.

What Your Maryland Budget Buys in Estero

Maryland home prices vary widely, from Baltimore’s median of about $244,838 to much higher prices in Montgomery, Howard and Anne Arundel counties. Estero’s median sale price was about $484,757 in mid-2026, with homes taking around 78 days to sell. Many Marylanders find that their budget buys a newer home with more amenities, a pool and a gated community lifestyle.

Coming from a Maryland colonial or rowhouse, expect a few differences: most Estero homes are single-story, built from concrete block, with tile or metal roofs, screened lanais and no basement. Storage is in the garage, and outdoor living happens year-round.

Remember to compare the full monthly cost of ownership. In Estero, that includes HOA dues, property taxes, homeowners insurance, possible flood insurance and, in some newer communities, CDD assessments that appear on the property tax bill. A home with a newer roof and impact windows can have a much lower insurance premium, which often offsets a slightly higher purchase price. We are happy to run side-by-side cost comparisons for the homes you are considering.

Getting Between Maryland and Estero

Flying

Southwest Florida International Airport (RSW), about 15 minutes from Estero, handled a record of more than 11.1 million passengers in 2025. Nonstop service to the Baltimore and Washington area has included BWI on Southwest, Washington Dulles on United and Reagan National on American, with the busiest schedules in winter. Flights take about two and a half hours.

The Auto Train

Marylanders have a big advantage: the Amtrak Auto Train. It departs daily from Lorton, Virginia, just south of Washington, D.C., and arrives the next morning in Sanford, Florida, near Orlando. You ride overnight while your car travels with you, skipping about 800 miles of I-95. Fares vary by season, with promotional coach fares sometimes very low and vehicle charges added on. From Sanford, Estero is about three and a half hours south.

Driving

The drive from Baltimore to Estero is about 1,000 miles, roughly 15 hours via I-95 and I-75. Many people split it into two days with an overnight stop in the Carolinas or Georgia.

Climate: No More Snow Days

BWI averages about 19 inches of snow a year, and Maryland winters bring ice storms, gray skies and cold rain. In Estero, the average January high is about 75°F with lows in the mid-50s. Winter is the best season of the year: dry, sunny and perfect for golf, beaches and outdoor dining. Summers are hot and humid, with average August highs around 92°F and frequent afternoon thunderstorms. If you are used to Maryland’s humid summers, the Florida summer will feel familiar, just longer.

Hurricanes vs. Maryland Storms

Maryland gets nor’easters, tropical storm remnants and the occasional derecho. Southwest Florida’s major weather risk is hurricanes, with the season running from June 1 through November 30. Hurricanes come with days of warning, and most of preparation is done before the season starts: protecting windows, trimming trees, stocking supplies and knowing your evacuation zone. Newer homes with impact windows and generators make storm season far less stressful. Our hurricane center has checklists and resources.

Crabs, Seafood and Food Culture

No Marylander moves without asking about crabs. Blue crabs live in Gulf waters too, but the bigger local tradition is stone crab season, which runs from October 15 through May 1. Stone crab claws are served chilled with mustard sauce and are a must-try. Gulf grouper, shrimp, snapper and oysters fill local menus, and you will find plenty of seafood shacks, waterfront restaurants and fish markets. Old Bay is easy to find in local grocery stores, and more than a few Maryland transplants host crab feasts on their lanais.

Sports: Orioles, Ravens and Spring Training

Orioles fans have a perk in Florida: the team holds spring training in Sarasota, about an hour and a half north of Estero. Closer to home, the Boston Red Sox and Minnesota Twins train in Fort Myers every February and March. The Florida Everblades play hockey at Hertz Arena in Estero, and FGCU basketball is popular. For Ravens games, local sports bars and fellow Maryland transplants make it easy to find a watch party, and Tampa and Miami host NFL games a few hours away.

Military, Federal and Government Retirees

Maryland has a large population of federal employees, military members and government contractors, many of whom retire to Florida. Because Florida has no state income tax, federal pensions, military retirement pay and Thrift Savings Plan withdrawals are not taxed by the state. Southwest Florida also has VA clinics, active veterans organizations and a strong military retiree community. Many federal retirees also appreciate the shorter flight back to the D.C. area to visit family.

Where Marylanders Like to Live in Southwest Florida

• Estero gated communities: Popular with retirees and families for amenities, security and social life.
• Golf and country clubs: Many Marylanders choose bundled golf communities where membership comes with the home.
• Bonita Springs and Naples: For closer beach access and upscale dining.
• Fort Myers and Cape Coral: For more affordable options and waterfront living on canals, a natural fit for boaters coming from the Chesapeake Bay.

Compare areas in our Naples vs. Bonita Springs vs. Estero vs. Fort Myers guide, or browse Estero gated communities.

Snowbird or Full-Time Resident?

Many Marylanders start as snowbirds, spending January through April in Southwest Florida and the rest of the year at home. Others make the full move right away. Each approach has trade-offs:

• Seasonal residents keep their Maryland domicile, continue to pay Maryland income taxes and do not qualify for Florida’s homestead exemption on their Florida home. Non-homestead properties are also subject to a 10% annual cap on assessment increases rather than the 3% homestead cap.
• Full-time Florida residents can claim homestead, avoid Maryland income tax going forward and take advantage of Florida’s estate planning benefits. If you keep a home in Maryland, keep careful records showing that Florida is your primary home and where you spend your time.
• The hybrid: Some retirees become Florida residents and keep a smaller place in Maryland near family for the summer. Talk to a tax advisor about how Maryland treats part-year and nonresident owners.

From the Chesapeake to the Gulf: Boating and Fishing

If you spent weekends on the Chesapeake Bay, Southwest Florida will feel like an upgrade with a longer season. Estero Bay, Charlotte Harbor, Pine Island Sound and the Gulf of Mexico offer endless boating and fishing, and you can be on the water twelve months a year. Cape Coral has hundreds of miles of canals with direct Gulf access, and many Estero-area communities are within a short drive of marinas and boat ramps. Inshore anglers chase snook, redfish and trout, while offshore trips target grouper and snapper. Tarpon season in late spring and early summer draws anglers from all over the world.

Healthcare After the Move

Marylanders are used to world-class healthcare close to home. Southwest Florida’s largest system, Lee Health, operates hospitals in Fort Myers and Lee Health Coconut Point in Estero, which offers outpatient care and a freestanding emergency department. Naples is served by the NCH system. Many people keep specialists back home for a while and transition gradually. Set up a primary care doctor soon after you arrive, since practices can fill quickly during the winter season.

Plan a Scouting Trip

Before you buy, spend a few days seeing the area in person. A good scouting trip includes touring several gated communities in Estero, driving the routes you would take for groceries, doctors and the airport, spending an afternoon at the beach in Bonita Springs or Naples and having dinner at Coconut Point or in downtown Naples. If you can, visit once in winter and once in summer. Our team can set up a custom tour based on your budget and lifestyle.

What Daily Life Looks Like in Estero

For most Marylanders, the biggest change is how much time they spend outdoors. Winter mornings start with a walk around the community lake, pickleball or a round of golf. Afternoons might include a trip to the beach, lunch at Coconut Point or a nap by the pool. Evenings are for sunsets, dinners with neighbors and community events. Errands are quick, traffic is manageable outside of peak season and the airport is close when it is time to visit family. Our Estero newcomer hub covers clubs, groups and resources for settling in.

Becoming a Florida Resident

1. Record a Florida Declaration of Domicile with the Lee County Clerk (about $10 to record).
2. Get a Florida driver license within 30 days of establishing residency.
3. Register and title your vehicles in Florida, including a VIN verification for out-of-state vehicles.
4. Get Florida auto insurance with at least $10,000 in personal injury protection and $10,000 in property damage liability.
5. Register to vote in Lee County.
6. File for homestead exemption by March 1.
7. File a part-year resident return in Maryland for the year you move, and update your estate plan with a Florida attorney.

Your Maryland to Estero Moving Checklist

1. Meet with a CPA or estate attorney about Maryland income, estate and inheritance tax planning before you move.
2. Decide whether to sell, rent or keep your Maryland home.
3. Visit Estero in winter and, if possible, summer.
4. Get pre-approved for a mortgage or confirm proof of funds.
5. Request homeowners and flood insurance quotes on the homes you like before you make an offer.
6. Book movers early; spring and fall are the busiest times for Mid-Atlantic to Florida moves.
7. Reserve the Auto Train well ahead if you plan to use it, especially in October, November and spring.
8. Once here, complete your Florida residency steps and file for homestead by March 1.
9. Sign up for AlertLee and learn your hurricane evacuation zone.
10. Find doctors, a dentist and a veterinarian, and transfer records.

Moving from Maryland to Florida FAQ

About the Author: Sal DiBenedetto

Sal is a licensed real estate broker with The DiBe Group, brokered by eXp Realty, serving Estero, Fort Myers, Cape Coral and Southwest Florida. He helps Marylanders and Mid-Atlantic buyers compare Southwest Florida communities and understand the full cost of owning a home here. More about Sal · Contact

Tax, insurance and price figures come from public sources as of 2026 and can change. Confirm details with your advisors.