Each edition grades its towns against each other only.
The picture is mixed. Cost of living is its weak spot: the typical home is worth about $466K, 5.9 years of the Orlando metro’s $79K median household income. Health is its strong suit (A) — CDC estimates put its residents' health ahead of 91% of the country. It also does well on walkability (A): it is more walkable than 90% of U.S. towns. Put together, the subjects come to a C+ overall, better than 45% of U.S. towns. Its place in the ranking is 205th of 634 in Florida. 65% of adults 25 and older hold a bachelor’s degree or more in Winter Park, above both Florida’s towns (31%) and U.S. towns (29%). On civic life, just 5 of Florida’s 327 towns do better.
Figures: health, CDC PLACES · home values, Zillow · incomes, Census ACS, 2020–24.
Where Winter Park beats most towns.
Census counts: 270 in 1890, 29,795 in 2020. The archive holds 11 old photos and papers going back to 1882 and 4 maps from 1956 on.
12 places on the National Register of Historic Places.
Each subject compared with towns across the country (schools within Florida), ordered by how far Winter Park is from typical.
How TownRatings grades towns →
Museums, parks, gardens and other places to visit around Winter Park. Close and well known come first.
Big draw20 mi Theme parkWalt Disney World Resort
Big draw11 mi Theme parkUniversal Studios Florida9.5M visitors a year
Big draw5 mi Stadium & arenaCamping World Stadium
Big draw12 mi Theme parkUniversal Epic Universe
5 mi Stadium & arenaKia Center
Big draw12 mi Theme parkUniversal's Islands of Adventure9.5M visitors a yearWalt Disney World Resort: Anthony Quintano from Westminster, United States, CC BY 2.0 · Universal Studios Florida: Radiobroadcastcenter, CC BY-SA 3.0 · Camping World Stadium: Quintin Soloviev, CC BY 4.0 · Universal Epic Universe: Martin Lewison, CC BY 2.0 · Kia Center: 350z33 (talk), CC BY-SA 3.0 · Universal's Islands of Adventure: David Bjorgen, CC BY-SA 2.5
Who provides power, water and the rest in Winter Park, and how to reach them.
EPA SDWIS (Oct 9, 2026) · HIFLD + EIA-861 2025 · Census 2020 ZCTAs · NCES 2024–25 · registration: vote.gov, updated Nov 17, 2025.
Ordered by what stands out in Winter Park.
Winter Park draws workers from Orlando and beyond, fares better on crime within Florida than nationally and has more 90° days than nearly all U.S. towns.
33,682 jobs are based in Winter Park, 2.6 for every working resident, so most of the people who work here commute in. The average commute takes 22 minutes, against 28 across Florida.
Winter Park’s middle household income is $106,000. Just just over a tenth of the town’s working residents have a job in town. Jobs in Winter Park grew by 7,391 from 2013 to 2023, reaching 33,682. Also worth knowing: among workers locally, 30% work from home.
| Winter Park | Florida towns | U.S. towns | |
|---|---|---|---|
| Work from home | 30% | 14% | 11% |
| Median household income | $106,000 | $73,000 | $80,000 |
| Average trip to work | 22 minutes | 27 minutes | 25 minutes |
| Working residents who work in town | 12% | 5% | 8% |
Census LEHD 2023 · ACS
Two of the 8 schools are below, and why each made the list. Its public schools are run by the Orange school district. The largest public high school is Winter Park High, with 3,277 students.
| School | Level | Students | Letter |
|---|---|---|---|
| Lakemont ElementaryLargest public elementary schoolGrades K–5 | Grades K–5 | 629 | B+ |
| Winter Park HighLargest public high schoolGrades 9–12 | Grades 9–12 | 3,277 | B |
NCES · EDFacts · graded within FL on state tests and graduation
Its widest gap with Florida is no health insurance: 8.8% of those 18–64 have no health insurance, against 15.9% statewide.
Nearly a fifth of adults get no exercise outside work in Winter Park. This Florida town beats the Florida average on 19 of 31 CDC measures and trails it on 1.
| Winter Park | Florida towns | U.S. towns | |
|---|---|---|---|
| Smoke cigarettes (CDC PLACES) | 8.9% | 13% | 14% |
| Get no exercise (CDC PLACES) | 19% | 25% | 25% |
| Frequent physical distress (CDC PLACES) | 12% | 15% | 14% |
| Frequent mental distress (CDC PLACES) | 14% | 16% | 17% |
| What stands out | Winter Park | FL |
|---|---|---|
| Fewer uninsured adults | 8.8% | 15.9% |
| Fewer adults facing food insecurity | 9.4% | 16.8% |
| More adults who have had cancer | 10.6% | 9.1% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
Walkers can cover 4.2 miles of trail in 18 parks and preserves. The biggest park or preserve is Winter Pines Golf Course, at 134 acres.
| Winter Park | Florida towns | U.S. towns | |
|---|---|---|---|
| Conserved land | 2.8% | 3% | 4.3% |
| Miles of trail per square mile | 0.4 miles per square mile | 0.4 | 0.4 |
| Biggest places to walk | Trails | Acres |
|---|---|---|
| 1. Central Park | 0.5 mi | 9 |
| 2. HBR Park | 0.4 mi | 4 |
| 3. Ward Park | 0.3 mi | 66 |
Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US
The median property tax bill is $5,401, against $2,730 across Florida, another input to its cost-of-living grade.
The typical Winter Park home is worth about $466,000, up 2.3% in a year, 24% above the Florida typical home. The median rent for Winter Park comes to $1,738 a month. Sellers in Winter Park got 94.6% of the asking price, typically.
| Winter Park | Florida towns | U.S. towns | |
|---|---|---|---|
| Median rent | $1,738 a month | $1,647 a month | $1,185 a month |
| Households that own their home | 66% | 72% | 73% |
| Renters paying 30%+ of income on rent | 56% | 59% | 48% |
Census ACS, 2020–24 · Zillow Home Value Index · Redfin Data Center
At 27 crimes per 1,000 residents a year, it reports more crime than 55% of Florida’s graded towns. Reported crimes fell from 676 to 515 over the last three FBI years, a drop beyond ordinary year-to-year swings.
The property crime rate in Winter Park is 14.1 per 1,000 residents. The level of violent crime here is 2.4 per 1,000 residents.
| Winter Park | Florida towns | U.S. towns | |
|---|---|---|---|
| Property crimes per 1,000 (2025) | 14.1 per 1,000 residents | 12.6 | 9.9 |
| Violent crimes per 1,000 (2025) | 2.4 per 1,000 residents | 2.1 | 1.6 |
FBI crime data, 2025 · crimes reported to police
The Orlando Intl Ap weather station, 11 miles away, records that about 110 days a year reach 90°, more than in 97% of U.S. towns. January nights average 49.3°, milder than in 98% of U.S. towns; July afternoons average 92.2°.
For Winter Park, the typical July afternoon high is 92°F. Snow is a rarity.
| Winter Park | Florida towns | U.S. towns | |
|---|---|---|---|
| January low | 49°F | 51°F | 22°F |
| July high | 92°F | 91°F | 85°F |
NOAA U.S. Climate Normals, 1991–2020
Federal disaster aid has reached households in Winter Park after 10 declared disasters, most recently in 2024. Expected damage from storms and floods is lower here than in just over half of U.S. communities. The town has had 57 paid flood insurance claims since 1992.
FEMA disaster declarations and aid · FEMA flood insurance claims · FEMA National Risk Index · OpenFEMA
13 within 15 miles of the center of Winter Park
About 11 of every 100 Winter Park residents are enrolled in college, against 6 across Florida.
12 places in Winter Park on the National Register of Historic Places.
37 notable people were born in Winter Park.
City in Florida, US
Winter Park is a city in Orange County, Florida, United States. The population was 29,795 at the 2020 census. It is part of the Orlando metropolitan area. Winter Park was founded as a resort community by northern business magnates in the late 19th and early 20th centuries. It is home to Rollins College, a private liberal arts college.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
4 towns share a border with Winter Park.
| Town | FL rank | Overall | Cost | Safety | Schools | Health |
|---|---|---|---|---|---|---|
| Winter Park | #205 | C+ | D− | C | B− | A |
| Fairview Shores | #156 | B− | C | — | B− | B− |
| Maitland | #202 | B− | D− | C+ | B− | A |
| Orlando | #323 | C | D | — | B− | B |
| Eatonville | — | — | C+ | — | B− | C− |
Eatonville has fewer than 2,500 residents, so it gets subject grades but no overall grade. Fairview Shores, Orlando and Eatonville report no FBI crime data of their own. Compare Winter Park with a neighbor →
Short answers, built from the data on this page.
Winter Park grades C+ overall, better than 45% of U.S. towns and #205 of 634 in Florida. It grades A for health, C for safety and B− for schools. Cost of living is its weak spot, with a D−.
37 notable people were born here, including Spencer Locke and Dax McCarty.
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