Moving to Winter Park, FL: What Out-of-State Buyers Should Know

I moved to Winter Park in July 1978, and a big part of my work now is helping people do the same thing from somewhere else. Many of them come to me through RE/MAX agents in other states. The questions are almost always the same, and most of the answers are things nobody tells you until you’re under contract. Here they are up front. For the record: Over 37 years in the Real Estate Industry · licensed in Florida since 1989.

Start with the map, not the listings

Winter Park is its own city, just north of Orlando in Orange County. It’s about 10 square miles, so many people who want “Winter Park” end up comparing it with its neighbors:

• Winter Park (Orange County): historic streets, the chain of lakes, Park Avenue.
• Maitland (Orange County): directly north, with a deep supply of mid-century homes.
• Baldwin Park (City of Orlando, Orange County): a planned neighborhood on the former Naval Training Center, just south of Winter Park.
• Longwood (Seminole County): established neighborhoods, acreage along Markham Woods Road.
• Lake Mary (Seminole County): planned and golf communities, newer housing.

The county line matters. It decides your property appraiser, your tax bill and your school district. A “Winter Park” mailing address can even be in Seminole County, so check every parcel.

What the housing looks like

Winter Park’s older neighborhoods were shaped by the 1920s Florida Land Boom, and the city has recorded more than 700 historic structures. You’ll also see plenty of 1950s and 1960s ranch homes, a steady stream of new construction on older lots, and lakefront homes that are priced as their own market. If you’re coming from a place where houses are newer and more uniform, expect a wider spread in condition and price from one block to the next.

The Florida homework that surprises newcomers

Your taxes won’t be the seller’s taxes. Florida’s Save Our Homes rule caps how much the assessed value of a homesteaded home can rise each year: 3% or the change in CPI, whichever is less. When the home sells, it’s reassessed at market value the following January 1. A long-time owner’s tax bill can be far below what yours will be, so budget from the purchase price, not the listing’s tax history.

Homestead is worth claiming right away. If you own the home and it’s your permanent residence on January 1, you can apply for the homestead exemption by March 1 of that year. It takes up to $50,000 off the assessed value: the first $25,000 applies to all property taxes, and the additional amount applies to value above $50,000 for non-school taxes and is now adjusted for inflation. It also starts your own Save Our Homes cap.

No state income tax. Florida’s constitution prohibits a state income tax on individuals.

Insurance comes before the offer, not after. Insurers look closely at roof age, and older homes often need a 4-point inspection of the roof, electrical, plumbing and HVAC. A wind mitigation inspection documents features like roof straps and opening protection, and Florida insurers must offer discounts for qualifying features. Get real quotes during your inspection period.

Flood is separate. Standard homeowners policies generally don’t cover flood. Check the FEMA flood map for any address, especially near a lake, and ask about flood insurance even if the lender doesn’t require it. Since October 1, 2025, Florida sellers must give buyers a flood disclosure covering known flood damage, claims and assistance.

Hurricane season runs June 1 through November 30. Plan an inspection and insurance timeline that doesn’t leave you scrambling for a policy with a storm on the map.

Getting around

• SunRail and Amtrak. The Winter Park/Amtrak station on West Morse Boulevard, next to Park Avenue, serves both SunRail commuter trains and Amtrak.
• Air travel. Orlando International Airport is reached from Winter Park’s east side via Semoran Boulevard (SR 436). Orlando Sanford International Airport is to the north, near Lake Mary.
• I-4 runs along Winter Park’s west side, and U.S. 17-92 runs through town. Before you commit, drive your work route at the hour you’ll actually drive it.

Schools

City of Winter Park homes are in Orange County Public Schools. Seminole County addresses are in Seminole County Public Schools. Attendance zones change and don’t follow city limits or ZIP codes, so verify any address with the OCPS or SCPS school locator before you make an offer. My post on comparing Central Florida school zones explains how.

Buying from a distance

Most of my relocation clients see a house first by video. I’ll tell you what the camera misses: the traffic on the street, the slope of the yard, the age of the roof, what’s going on next door. Closing remotely is common, and my post on closing remotely in Florida covers how it works. Before we tour, we’ll sign a written buyer agreement, and I’ll walk you through it line by line first.

Working with Will

I’ve spent a long stretch in valuation work, so I read the appraisal and the insurance picture closely. That’s where relocation deals usually wobble. Credentials, stated plainly: 2026 RealTrends Verified, top 0.5% of Florida agents; 2026 RealTrends Verified, ranked #10 in Winter Park by transactions; RE/MAX Hall of Fame; Golf Community Certified through RE/MAX Golf Lifestyles.

Relocation FAQ

Is Winter Park part of Orlando?

No. Winter Park is a separate city just north of Orlando, in Orange County, with its own government and its own electric utility.

When do I apply for homestead?

After you own and live in the home as your permanent residence on January 1, apply with the county property appraiser by March 1 of that year.

Do I need flood insurance?

Your lender will require it in certain flood zones. Elsewhere it’s optional, but standard homeowners policies generally exclude flood, so get a quote.

Can I buy before I move?

Yes. Video tours, digital signatures and remote closings make it workable, and I’ll be your eyes on the ground.

Planning a move to Winter Park?

Tell me where you’re coming from, your timeline and what matters most. I’ll call you, and we’ll start with the map.

Will LaValle, REALTOR® · RE/MAX 200 Realty · 1155 Louisiana Ave., Suite 110, Winter Park, FL 32789 · 407-620-7785 · will@irlhomes.com · FL license #3389936