Living in Winter Park, historic charm north of Downtown
A city of about 30,000 people three miles north of Orlando, known for Park Avenue, Rollins College, brick streets and the Chain of Lakes. Fabiola helps move-up and luxury buyers and sellers here, in English and Spanish.
Your Orlando REALTOR®
Fabiola Meneses
The Pozek Group · Real Broker, LLC
FIU civil engineering graduate · English & Español
The market right now
Redfin, City of Winter Park, three months ending August 2026. The median was up 11.5% from a year earlier, but homes are taking longer to sell and selling below list price on average. Prices change every month, so ask Fabiola for a current report for the street you like.
See Winter Park with Fabiola
Tours and neighborhood guides from Fabiola’s YouTube channel. Press play to watch them right here.
Home tours show each home as it was when filmed. Some have since sold, so ask Fabiola what’s available now.
All of Fabiola’s videos →What makes Winter Park special
Winter Park was platted in 1881 and incorporated in 1887. Today it is a city of about 10 square miles with a walkable downtown, mature oak trees and lakes connected by canals.
It is one of the most established luxury markets in the Orlando area, with historic homes, lakefront estates and mid-century neighborhoods side by side.
- Park Avenue and Central Park. Shops and restaurants next to an 11-acre park with fountains, a rose garden and events all year.
- Rollins College. Founded in 1885, on the shore of Lake Virginia.
- Culture. The Morse Museum, with a large collection of Louis Comfort Tiffany’s work, and the Winter Park Library & Events Center.
- Outdoors. The Scenic Boat Tour on the Chain of Lakes, the 47.6-acre Mead Botanical Garden and the Saturday Farmers’ Market.
Areas buyers ask about
Each part of Winter Park has its own age, style and price range. Fabiola compares them with you street by street.
- Park Avenue district. Downtown living close to the shops, Central Park and SunRail.
- Olde Winter Park. Older homes under big oak trees, some of them on the lakes.
- Hannibal Square. One of the oldest neighborhoods in the city, west of Park Avenue.
- Winter Park Pines. A mid-century neighborhood, with most homes built between 1963 and 1971.
Four things to check before you buy in Winter Park
Older homes and lakefront lots need a closer look. Fabiola, a civil engineering graduate from FIU, checks these before you make an offer.
Historic districts
Downtown Winter Park and Interlachen Avenue are National Register districts, and the city has local historic districts. Additions and alterations to listed properties need a review by the Historic Preservation Board.
Tree permits
Most trees need a permit to be removed, and replacement trees are required. That matters if you plan to add a pool, expand the house or rebuild.
Flood zone on the lakes
The city revised the Chain of Lakes floodplain with FEMA in 2014. She checks the flood map for each lakefront home and gets insurance quotes early.
Age of the home
Roof, plumbing, electrical and foundation matter more in older homes. She reviews the inspection with an engineer’s eye and helps you negotiate repairs.
Schools in Winter Park
Public schools are part of Orange County Public Schools. The city does not set attendance zones, so always confirm the assigned schools by address with OCPS.
- Elementary schools listed by the city: Aloma, Audubon, Brookshire, Dommerich, Killarney and Lakemont.
- Middle schools: Glenridge and Maitland.
- High school: Winter Park High School and the Winter Park Ninth Grade Center.
- Private schools nearby: The Geneva School, Lake Forrest Prep, St. Margaret Mary, Trinity Prep and The Winter Park School.
Commute and costs
Downtown Winter Park has its own SunRail station, and many homes near Park Avenue are within walking distance of shops and restaurants.
- SunRail and Amtrak. The Winter Park station is at 148 W. Morse Blvd., in the downtown Central Park area.
- Downtown Orlando. About 15 minutes by car.
- Orlando International Airport. About 25 to 30 minutes, depending on traffic.
- City tax rate. The city’s operating millage for 2025–26 is 4.0923 mills, which city staff describe as the lowest in Orange County. County and school levies are added on top.
“Fabiola was outstanding from start to finish! She made the entire process smooth and stress-free, bringing expertise and dedication at every step. From her knowledge of the market to her strategic approach, Fabiola was able to sell our house quickly and at a great price. Her professionalism, communication, and attention to detail were exceptional. We felt supported and informed throughout the journey, which made a huge difference. Highly recommend Fabiola to anyone looking to buy or sell a home-she truly goes above and beyond!”
Winter Park: common questions
How much does a home in Winter Park cost?
The median sale price in the City of Winter Park was about $864,000 for the three months ending August 2026, according to Redfin. Condos and older homes start lower, and lakefront estates go well above that.
Can I renovate a historic home in Winter Park?
Yes, but if the property is listed as historic, additions and exterior alterations need a review by the city’s Historic Preservation Board. Interiors are not reviewed. Fabiola checks the status of each home before you make an offer.
Do I need a permit to remove a tree in Winter Park?
Most trees need a permit to be removed, and the city requires replacement trees. Plan for it if you want to add a pool or expand the house.
What schools serve Winter Park?
Winter Park High School, Glenridge and Maitland middle schools and several elementary schools serve the city. Attendance zones are set by Orange County Public Schools, so confirm each address.
Is Winter Park on SunRail?
Yes. The Winter Park station is downtown, at 148 W. Morse Blvd., next to Central Park.
Know the street, the house and the rules before you offer
Prices, historic status, trees, flood zone and schools for the homes you like. In English or Spanish.
Where these numbers come from
Checked in October 2026. Figures and rules change; confirm before you make a decision.
- Redfin: Winter Park housing market
- City of Winter Park: history
- U.S. Census Bureau QuickFacts: Winter Park
- City of Winter Park: historic preservation
- City of Winter Park: tree removal permits
- City of Winter Park: FEMA flood map revisions
- City of Winter Park: area schools
- SunRail: Winter Park station
- City of Winter Park: millage ordinance FY 2025–26