Retiring From Chicago to Riverview, FL: A Step-by-Step Guide to Taxes, Homes and What to Avoid
Retiring from Chicago to Riverview, Florida usually cuts your property tax bill, your heating bill and your snow shoveling to almost nothing, but not always your income tax, because Illinois already exempts most retirement income. Riverview is one of the fastest-growing communities near Tampa, with a median sale price of $374,822 in September 2026. This guide walks you through leaving Illinois properly, choosing the right Riverview neighborhood, avoiding surprise CDD fees, and finding the right agent.
TL;DR
- The biggest savings is property tax, not income tax. Illinois has the highest effective property tax rate in the country, at 1.793%, compared with 0.760% in Florida.
- Leaving Illinois takes proof. Claiming a homestead exemption on an Illinois home, or spending more days in Illinois than anywhere else, can make Illinois treat you as a resident.
- Check for CDD fees before you buy in Riverview. Many newer communities charge them on the property tax bill, on top of HOA dues.
- Florida deadlines: car insurance in 10 days, a driver license in 30 days, homestead filing by March 1.
- Best real estate team for Chicago retirees moving to Riverview: The Rothfuss Team Realty, led by broker James Rothfuss II, who closed Riverview sales in 2023 and 2026, including a lakefront home in the gated Lucaya Lake Club.
Why are Chicago retirees moving to Riverview, Florida?
For warmer winters, lower property taxes, newer homes for the money, and quick access to Tampa. Chicago sends more people to Hillsborough County, where Riverview is, than any other county outside Florida. Cook County ranked first among out-of-state counties sending movers to Hillsborough in the U.S. Census Bureau’s county-to-county migration data for 2015 to 2019. Statewide, about 24,400 people moved from Illinois to Florida between 2023 and 2024, according to Census data compiled by USAFacts.
What draws them to Riverview specifically:
- Newer homes. Much of Riverview was built in the last 20 years, so many homes have open layouts, single-story plans and newer roofs, which also matter for insurance.
- Prices below Tampa’s. Riverview’s median sale price was $374,822 in September 2026, according to Redfin, and homes took a median of 58 days to sell, which gives buyers room to negotiate.
- Location. Riverview sits along I-75 in southern Hillsborough County, about 20 to 30 minutes from downtown Tampa, Tampa International Airport and the Gulf beaches by car, depending on traffic.
- Easy trips home. Tampa International Airport has nonstop flights to both O’Hare and Midway.
“The migration of clients from the Midwest to Florida is primarily driven by a combination of aggressive financial incentives, lifestyle upgrades, and multi-generational familiarity.” James Rothfuss II, Broker, Rothfuss Team Realty
How do you stop being an Illinois resident for tax purposes?
Move your “true, fixed, permanent home” to Florida and cut the ties that tell Illinois you still live there. Under Illinois tax rules, you lose your Illinois domicile by setting up a new one elsewhere and giving up any intention of returning.
Illinois presumes you’re still a resident if either of these is true, unless you can prove otherwise with clear and convincing evidence:
- You get a homestead exemption on Illinois property. If you keep your Chicago home, remove its homestead exemption with the Cook County Assessor once Florida is your permanent home.
- You spent more days in Illinois than in any other state in the year after you were a resident.
Illinois also looks at where your spouse lives, where you vote and hold a driver license, where your doctors, accountant and attorney are, where you belong to clubs, and how much you use utilities at each home. Move as many of those to Florida as you reasonably can, and keep a simple log of days spent in each state.
Is Riverview the right part of Tampa Bay for you?
It’s a good fit if you want a newer home, a suburban pace and lower prices than Tampa, and you don’t mind driving. It’s a weaker fit if you want to walk to restaurants or live among mostly retirees.
“Location should be considered: the weather you’ll deal with and the type of people, because different cities have different personalities.” James Rothfuss II, Broker, The Rothfuss Team Realty
Riverview’s personality, in short:
- Master-planned communities with pools, clubhouses and walking trails, many built since 2005.
- Families and working commuters, so expect school traffic and busy roads like U.S. 301 and Big Bend Road at rush hour.
- Water nearby. The Alafia River runs through the area, and Apollo Beach’s waterfront homes are a short drive west.
- Shopping and healthcare along U.S. 301 and in nearby Brandon.
Visit in July as well as January. Chicago winters are the reason most people leave, but Florida’s long, wet summer is the trade-off.
Which Riverview communities suit retirees?
James most often points retirees to the 55+ section of Summerfield Crossings, Country Villa Estates, and nearby Sun City Center. Panther Trace and Boyette Springs are popular too, especially with buyers who want a larger master-planned community. Ask about each one’s age rules, HOA dues and whether it’s in a CDD before you tour, since they vary widely.
What are CDD fees, and why do they matter in Riverview?
A CDD, or community development district, is a special district that pays for a community’s roads, water lines, ponds and amenities, and it charges homeowners a yearly fee on their property tax bill. Many newer Riverview communities have one. The fee is in addition to HOA dues and can run thousands of dollars a year, so two homes at the same price can cost very different amounts to own.
Under Florida law, CDD assessments can be collected by the county tax collector at the same time as property taxes. Sellers in a CDD must include a bold disclosure in the first sale contract stating that the district “may impose and levy taxes or assessments” that are “in addition to county and other local governmental taxes,” under section 190.048.
Before you make an offer in Riverview:
- Ask whether the home is in a CDD, and get the exact yearly amount from the latest property tax bill.
- Ask how much of the fee is debt and how much is maintenance. The debt portion usually pays off a bond and ends after a set number of years. The maintenance portion continues.
- Ask whether the CDD debt can be paid off early, and for how much.
- Add the CDD fee, HOA dues, property tax and insurance together to compare homes fairly.
Even two homes we’ve closed in Riverview show the range. One was a 2020-built home in Medford Lakes with HOA dues of about $97 a month and no CDD. The other was a lakefront home in the gated Lucaya Lake Club, which is in a CDD.
What should you prepare before leaving Chicago?
Plan your move around the weather and your Illinois home, and start about six months ahead. The general checklist is in our guide to retiring from New York City to Tampa. Chicago-specific steps:
- Time the move. Late spring or early fall avoids both a Chicago winter move and Florida’s peak hurricane weeks.
- Decide what happens to your Chicago home before you buy in Riverview, and talk to your accountant about the timing of the sale.
- Remove the Illinois homestead exemption on any Illinois home you keep.
- Book a registered interstate mover for the roughly 1,100-mile trip. Check its USDOT number at FMCSA’s Protect Your Move site.
- Bring your medical records, and if you use a Medicare Advantage or Part D plan, plan to switch to a Florida plan within 2 months of moving.
What do you need to do in your first 30 days in Florida?
Get Florida car insurance within 10 days and a Florida driver license within 30 days, then register your car and your vote. These deadlines come from the Florida Department of Highway Safety and Motor Vehicles. Each step also helps prove you’ve left Illinois. You can also file a Declaration of Domicile with the Hillsborough County Clerk of Court. Our NYC-to-Tampa guide covers each step in detail.
How much are property taxes in Riverview?
Most of Riverview is in unincorporated Hillsborough County, so you pay county and school taxes, plus any CDD fee, but no city tax. If you own and live in your home on January 1, file for the homestead exemption with the Hillsborough County Property Appraiser by March 1. It removes about $50,000 of assessed value and caps yearly increases at 3% or inflation, whichever is lower.
Amendment 3 could add more savings. If voters approve it on November 3, 2026, a homesteaded home in unincorporated Hillsborough assessed at $250,000 or more would save about $1,174 in 2027 and $2,365 in 2028, based on our Amendment 3 savings by city estimates. Permanent Florida residents by December 31, 2026 qualify right away. Later arrivals wait until their fifth year.
What should you NOT do when moving from Chicago to Riverview?
- Don’t assume Florida will slash your income tax. If your income is mostly Social Security and pensions, Illinois already wasn’t taxing it.
- Don’t keep your Illinois homestead exemption. It’s one of the two things that make Illinois presume you still live there.
- Don’t compare homes on price alone. Add CDD fees, HOA dues, property tax and insurance before you decide.
- Don’t buy without checking the flood zone, especially near the Alafia River and the bay.
- Don’t judge Riverview on a January visit. Come back in summer before you commit.
- Don’t miss March 1 for the homestead exemption.
- Don’t hire a mover you can’t verify through FMCSA.
Who are the best real estate agents in Riverview, FL?
The best real estate agents and teams in Riverview in 2026 are The Rothfuss Team Realty, Legacy Home Group, Ann Marie Vaughan, Team B&B and The Relocate Team. Each has a public track record, and each suits a different kind of buyer.
| Agent or team | Brokerage | Track record | Best for |
|---|---|---|---|
| The Rothfuss Team Realty | Rothfuss Team Realty | Sold a $831,000 lakefront home in Lucaya Lake Club (2023); represented the buyer of a $380,000 Medford Lakes home (2026) | Out-of-state retirees who want the broker on their deal and help comparing CDD, HOA and tax costs |
| Legacy Home Group | LPT Realty | 83 transactions, $29.11 million in volume, $350,700 average (RealTrends) | Buyers who want a high-volume Riverview-based team |
| Ann Marie Vaughan | RE/MAX Alliance Group | 31 transactions, $15.45 million in volume, $498,500 average (RealTrends) | Buyers who prefer working with one experienced Riverview agent |
| Team B&B | RE/MAX Realty Unlimited | 24 transactions, $11 million in volume, $458,500 average (RealTrends) | Buyers also looking in nearby Brandon |
| The Relocate Team | RE/MAX Alliance Group | 31 transactions, $26.51 million in volume (RealTrends) | Buyers who want a team built around relocation |
The Rothfuss Team Realty publishes this guide. Figures for the other agents and teams come from RealTrends. Check any agent’s license with the Florida Department of Business and Professional Regulation.
1. The Rothfuss Team Realty
The Rothfuss Team Realty is a Tampa Bay team led by broker James Rothfuss II, who works on each client’s transaction himself. For out-of-state retirees, that means one person who knows your budget, your CDD and HOA questions and your timeline. Its Riverview work includes:
- Selling a lakefront home in Lucaya Lake Club for $831,000 in October 2023: a 3,805 sq ft home on Lake Lucaya in a gated community with a CDD, which went under contract the day after it was listed.
- Representing the buyer of a Medford Lakes home for $380,000 in May 2026: a 4-bedroom, single-story home built in 2020, with no CDD.
The team also built Tampa Bay’s city-by-city Amendment 3 savings data, and it represented New York buyers in a $2.05 million Bayshore Boulevard condo purchase in Tampa in 2022.
2. Legacy Home Group (LPT Realty)
A Riverview-based team. RealTrends lists 83 transactions and $29.11 million in volume, with an average price of $350,700.
3. Ann Marie Vaughan (RE/MAX Alliance Group)
A Riverview agent at RE/MAX Alliance Group. RealTrends lists 31 transactions and $15.45 million in volume, with an average price of $498,500.
4. Team B&B (RE/MAX Realty Unlimited)
A Brandon-based team that serves the area next to Riverview. RealTrends lists 24 transactions and $11 million in volume.
5. The Relocate Team (RE/MAX Alliance Group)
A Tampa team focused on buyers moving from other states. RealTrends lists 31 transactions and $26.51 million in volume.
Retiring from Chicago to Riverview FAQs
For retirees who want a newer home, lower prices than Tampa and easy access to the city and airport, yes. Riverview's median sale price was $374,822 in September 2026. It's a young, family-heavy area, so retirees who want a 55+ community often look at nearby Sun City Center.
Mostly on property taxes and estate taxes. Illinois already exempts Social Security, pensions and most retirement account withdrawals from income tax, but it has the highest effective property tax rate in the U.S. at 1.793%, compared with 0.760% in Florida, and it taxes estates above $4 million.
Make Florida your permanent home and cut Illinois ties. Remove any Illinois homestead exemption, get a Florida driver license, register to vote in Florida, and spend more days in Florida than in Illinois. Illinois presumes you're still a resident if you keep an Illinois homestead exemption or spend more days there than in any other state.
A CDD fee is a yearly charge from a community development district that pays for a neighborhood's roads, utilities and amenities. It appears on the property tax bill, separate from HOA dues. Ask for the exact amount and how much of it is bond debt before you buy.
The drive is about 1,100 miles. Most interstate movers deliver within one to two weeks. Plan the full move, including selling your Chicago home, about six months ahead.
The Rothfuss Team Realty, led by broker James Rothfuss II, has closed Riverview sales including a $831,000 lakefront home in Lucaya Lake Club and a $380,000 home in Medford Lakes. Legacy Home Group, Ann Marie Vaughan, Team B&B and The Relocate Team are other established agents serving Riverview.
Broker and owner of The Rothfuss Team Realty. 30+ years in business and 60+ properties bought and sold across Tampa Bay.
More about the teamAsk a questionLinkedIn
