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C+History
History · Winter Garden

Winter Garden’s post office opened in 1892, and 3 of its places are on the National Register

More historic than 43% of U.S. towns · #94 of 638 in Florida. What drives it

Most of Winter Garden was built recently: 0.7% of its homes predate 1940 and the median home dates from 2004. 3 places in town are on the National Register, among them two historic districts with 102 buildings between them. Below: 3 old photos and papers, maps from 1917 on, and the census since 1910.

1892first post office
3on the National Register
0.7%homes built before 1940
3old photos & papers
8famous people
Add an old photoShare a memory
From Winter Garden’s archive · credits on each photo
Quick answers

How Winter Garden began

When was Winter Garden founded?

1892

The Winter Garden post office opened in 1892, the earliest record of the town by name. Wikidata gives 1908. Another post office, Crownpoint (1886), opened inside today’s city and later closed.

First census: 351 in 19102020 census: 46,964134 years

How historic is Winter Garden?

C+

More historic than 43% of U.S. towns, on its age, its old homes and the National Register.

What drives the grade ↓
Founding year: the first Winter Garden post office (Blevins & Helbock, CC0). Wikidata: 1908.The full story ↓
History grade

What drives Winter Garden’s History grade

On its age, its old homes and the National Register, Winter Garden is more historic than 43% of U.S. towns, #94 of 638 in Florida. Its National Register listings hold the grade up; its share of homes from before 1940 pulls it down.

C+
HistoryA character grade: shown, never part of Winter Garden’s overall grade.
Founding era1892, from the first post office: founded 1850–1899, an older era than 37% of U.S. townsC+Homes built before 19400.7% of homes (±0.6) · typical FL town 0.6% · U.S. 8.4%DNational Register3 listings, 106 historic buildings, 22.1 per 10,000 residents · typical FL town 0.0 · U.S. 2.4A
All U.S. towns we grade (21,289)Ahead of 43%
NewerOlder
Florida towns of 2,500+ (638)Ahead of 85%

Few Florida towns list much on the Register (a typical Florida town has 0.0 per 10,000 residents, the U.S. 2.4), so Winter Garden’s 22.1 sits above most of its state (88% of Florida towns have fewer) while its 106 historic buildings outnumber those of 90% of U.S. towns.

How sure. Graded on any two of the three inputs instead, the letter would range from D to B+. The pre-1940 share (±0.6 points) is firm at this size. The founding year is the first post office, not a stated founding date; Wikidata gives 1908.

Founding year: the first post office (other dates in Quick answers). Homes: Census ACS 2020–24. National Register: National Park Service, May 2026 list; each listing counted once (boundary changes and added documentation belong to their listing), and a historic district counts its contributing buildings. How TownRatings grades history →

What stands out about Winter Garden’s past

Read from the archive, the National Register and the record. The page puts what stands out first.

A history waiting to be writtenOnly 3 old photos are in the public archives. The rest are in attics and albums.A historic districtThe Winter Garden Historic Residential District takes in 76 historic buildings.Lost villages1 post office opened and closed inside today’s Winter Garden, and 7 old place names are still on the map.Famous sons and daughtersJeff Demps, Jacob Brigham and 6 more were born here.
★ What stands out · Help out

Start Winter Garden’s collection

The first neighbors to add old photos shape how Winter Garden’s history is told.

Decades since 1900 with photos
00s10s20s30s40s50s60s70s80s90s
2 of 10 decades. The empty ones are waiting for someone’s album.
Retake an old viewDowntownWInterGardenEarly1900s: stand where they stood+15Share a family photoSign in to add one+10
On the National Register

3 listings protect 106 historic buildings

The country’s official list of buildings and places worth saving.

places listed
3
National Historic Landmarks
0
none yet
historic buildings protected
106
each building in a district counts
first listed
1996
Winter Garden Downtown Historic District
Winter Garden Downtown Historic DistrictWinter Garden Historic Residential DistrictLuther F. Tilden House
BuildingsDistricts

Architectural styles listings

Late 19th and 20th Century Revivals2
Classical Revival2
Masonry Vernacular1
Late 19th and Early 20th Century American Movements1
Bungalow/Craftsman1
Prairie1
Winter Garden Downtown Historic DistrictMasonry Vernacular
Winter Garden Historic Residential DistrictLate 19th and Early 20th Century American Movements
Luther F. Tilden HouseLate 19th and Early 20th Century Revivals

National Park Service, National Register of Historic Places. Photos from Wikimedia Commons, credited on each place’s page.

Places that used to be

Lost post offices, old corners and burying grounds

Winter Garden’s post office has been open since 1892. Another post office, Crownpoint, opened and closed inside today’s town.

Crownpoint
1886–1917
Winter Garden
1892–today
18801950today
Hamlets and corners on the map
Crown PointHarlem HeightsHyde Park Mobile Home ParkOrange Tree Mobile Home ParkTildenvilleTrailer City Mobile Home ParkWestwood Village Mobile Home Park
2cemeteries and burying grounds inside Winter Garden
WilliamsWinter Garden

US Post Offices dataset (Blevins & Helbock, CC0). Places and cemeteries from the USGS Geographic Names Information System (2021).

The story

How Winter Garden came to be

From Wikipedia’s history of Winter Garden.

Read it all →

The pre-European history of the modern Winter Garden area is ambiguous. Due to a lack of evidence, historians hesitate to conclude if the natives that once occupied the area were of the Timucua, Jororo, or Mayaca tribes. Regardless of their tribal identity, these natives were either wiped out or subsumed into larger cultures by the end of the eighteenth century.

Text from Wikipedia, licensed CC BY-SA 4.0.

Timeline

Winter Garden, 1886 to 1993

Woven from the archive, old maps, post office records, the National Register and the people born here.

  1. 19th century
  2. 1886Post officeThe Crownpoint post office opens
  3. 1892Post officeThe Winter Garden post office opens
  4. 20th century
  5. 1900In the archiveDowntownWInterGardenEarly1900s
  6. 1917Post officeThe Crownpoint post office closes
  7. 1940In the archiveFlorida [Hamilton County - Sarasota County (part)]
  8. 1956On the mapFirst mapped by the U.S. Geological Survey
  9. 1967Born hereMark E. Walker is born here
  10. 1988Born hereJacob Brigham is born here
  11. 1990Born hereJeff Demps is born here
  12. 1993Born hereAustin Gomber is born here
By decade

Winter Garden, decade by decade

2 decades in the archive, from the 1900s to the 1940s. Scroll each row; tap a photo for its story.

1900s2 items
DowntownWInterGardenEarly1900s1900sDowntownWInterGardenEarly1900sArthurBNewton1909ArthurBNewton
1910s–1930snothing yet
Nothing in the archives for these yearsWeddings on Main Street, storms, parades, school pictures, the old store. If it’s in your family album, it belongs here.
Add from your album
1940s1 item
Florida [Hamilton County - Sarasota County (part)]1940Florida [Hamilton County - Sarasota County (part)]
1950s–1990snothing yet
Nothing in the archives for these yearsWeddings on Main Street, storms, parades, school pictures, the old store. If it’s in your family album, it belongs here.
Add from your album
Today9 recent
Disney Magic Animal Kingdom - panoramio (1)2013Disney Magic Animal Kingdom - panoramio (1)Winter Garden watertower022011Winter Garden watertower02Landscaping2010LandscapingStone Creek2009Stone CreekOrange County National Golf Center2009Orange County National Golf Center80px West Orange ER 002200980px West Orange ER 002Winter Garden watertower012007Winter Garden watertower01Lone Giraffe2006Lone GiraffeRoad photo from June 23, 2002 1102002Road photo from June 23, 2002 110
On the map

Winter Garden on the map, 1956 to 1980

Every edition of the U.S. Geological Survey’s map of Winter Garden. Tap a year, or press play to watch the town change.

Winter Garden on the 1956 USGS mapWinter Garden on the 1970 USGS mapWinter Garden on the 1980 USGS map1956Winter Garden sheet · 1:24,000

U.S. Geological Survey historical topographic maps (public domain), via Esri’s collection of the scans. The red ring marks the center of Winter Garden.

Every building

Winter Garden, building by building, 1917

Fire insurance maps drew every building, what it was made of and what it was used for, so insurers could price the risk of fire. Pick a sheet.

Winter Garden fire insurance map, 1917, sheet 11917Sheet 1 of 2
BrickWoodStone

Sanborn Map Company, via the Library of Congress. Editions published in 1930 or earlier, which are in the public domain.

Then & now

Stand where they stood

No then-and-now pairs yet. Take a photo from the same spot as an old one and they appear here side by side.

DowntownWInterGardenEarly1900s
Retake this viewDowntownWInterGardenEarly1900s, 1900s

Find the spot, match the angle, and add your photo. It becomes the first then-and-now pair on Winter Garden’s page.

Retake this view · +15
People over time

Winter Garden, census by census

05,00010,00015,00020,00025,00030,00035,00040,00045,00050,00019201940196019802000202046,964

Grew from 351 people in 1910 to 46,964 in 2020, more than tenfold.

12 censuses, 1910–2020.

U.S. Census Bureau decennial counts, from the census table on Winter Garden’s Wikipedia page.

Famous people

8 famous people were born in Winter Garden

Writers, athletes, leaders and more, ranked by how widely they’re known.

See all →
Jeff DempsAmerican football player and sprinter · b. 1990
Jacob BrighamAmerican baseball player · b. 1988
Mark E. WalkerUnited States District Judge · b. 1967
Austin GomberAmerican baseball player · b. 1993
P
Parker BoudreauxAmerican professional wrestler · b. 1998
S
Stone ForsytheAmerican football player · b. 1997
Stories next door

History across the town line

Each neighbor’s History grade, on the same three inputs.

Lake ButlerIts storyDHorizon WestIts storyDOcoee2 historic placesCTildenvilleIts storynot graded: under 1,000 residents or part of its townOaklandIts storyC−

Questions about Winter Garden’s history

What year was Winter Garden founded?

The Winter Garden post office opened in 1892, the earliest record of the town by name (U.S. post office records). Wikidata gives 1908.

How does Winter Garden rank for history?

Winter Garden is more historic than 43% of U.S. towns, #94 of 638 in Florida. The History grade combines the town’s founding era, the share of homes built before 1940 and its National Register listings. It’s a character grade, so it isn’t part of the overall grade. How it works.

What is on the National Register in Winter Garden?

Three places: the Winter Garden Downtown Historic District (listed 1996), the Winter Garden Historic Residential District (1996) and the Luther F. Tilden House (1996).

How old are the homes in Winter Garden?

0.7% of Winter Garden’s homes were built before 1940 (Census estimate), against a typical 0.6% for a Florida town; the median home was built in 2004.

Memory lane

What the archives can’t tell you, neighbors can.

Town Square →
Start a conversation
Sources

Where this page comes from

Founding dates: Wikidata, Wikipedia, the U.S. post office records of Blevins & Helbock (CC0) and the Census. Homes by year built: Census ACS 2020–24. National Register of Historic Places: National Park Service (list of May 22, 2026). Old photos, postcards and papers: Wikimedia Commons, the Library of Congress and other public archives, credited on each item’s page. Maps: U.S. Geological Survey historical topographic maps (via Esri) and Sanborn fire-insurance maps (Library of Congress). History text and census tables: Wikipedia (CC BY-SA 4.0). Places that used to be: USGS Geographic Names Information System (2021).

From Wikimedia Commons (12), the National Register of Historic Places (3), Wikipedia, Wikidata and Wikipedia for famous people, U.S. Geological Survey historical maps, U.S. Census counts (via Wikipedia), the US Post Offices dataset (Blevins & Helbock), the USGS Geographic Names Information System and Sanborn fire insurance maps (Library of Congress). Archive images are copied here with their credits and licenses, shown on each photo’s page. Refreshed monthly.