Historic Preservation Month

The month of May is National Historic Preservation Month, where we celebrate historic places and the preservation of those historic places to encourage a brighter future. Today we get to enjoy the beautiful and charming city of Winter Garden with all its great shops, restaurants, and things to do. But part of the reason that Winter Garden has so much charm is because the streets are literally paved with history. In honor of National Preservation Month, we met with Jim Crescitelli from the Winter Garden Heritage Foundation to gain a deeper appreciation of Winter Garden’s History.

DTWG: What does National Historic Preservation Month Mean to you?

JC: This is a great time to mark our past and celebrate our preservation efforts.

DTWG: What is unique about Winter Garden’s history?

JC: One of the things that makes Winter Garden so unique from a historical perspective is that so much of the original architecture still stands today. You don’t see that too often in other cities and it is great to be in a community that really cares about the preservation of its past.

DTWG: Why is preservation so important?

JC: By preserving the past and enjoying the present, we ensure a vibrant and successful future.

DTWG: What role has the Winter Garden Heritage Foundation played in the preservation of Winter Garden?

JC: The Winter Garden Heritage has been integral to the preservation of Winter Garden. The very first project that breathed life into starting a Heritage foundation was saving the Edgewater Hotel from demolition in the 90s. Since then we have played a role in restoring the Garden Theatre, converting the two Railroad Depots into Museums, and restoring the fire truck and caboose that you see outside of our facility today.

Now our goal is to educate visitors about the rich history we have in our town through the use of our archives and exhibits that we present. Our exhibit this month is titled “Find Your Way Home, There’s a Map for That” where we explore historic maps of Winter Garden. You can come view this exhibit Thursdays and Fridays from 11am – 3pm. Or call 407.656.3244 to book an appointment.

DTWG: What is your favorite historical landmark in Winter Garden?

JC: Lake Apopka. It is literally a piece of living history and as I like to say it was the battery for the area and now it is recharging.

Historic Facts About Winter Garden

  • Settlers began arriving in the Winter Garden area by the 1850s, attracted by the fertile muck land that bordered Lake Apopka.
  • The intersection of Plant St and Main St was where the city started.
  • Winter Garden was established in 1903 and officially incorporated as a City in 1908.
  • Because of the great farming conditions, Winter Garden became an agricultural empire by the mid 20th Century.
  • Winter Garden was the #1 exporter of citrus and vegetables in the WORLD.
  • The first Mayor of Winter Garden was A.B. Newton and he lived on Smith St. The house is still there today.
  • Winter Garden had two railroad Depots for transporting citrus. Most towns only had one.
  • The phrase “charming little city with a JUICY past” is referring to Winter Garden’s prominent citrus trading.
  • Winter Garden has both a Downtown Historic District and a Residential Historic District.
  • The oldest building in Downtown Winter Garden is the Bond Building where the Three Birds Cafe is located and it was built in 1912.
  • By 1920 the city had quickly become the center of commerce and agriculture in West Orange County.
  • In 2009, the City Commission created an Architectural Review and Historic Preservation Board to advise and make recommendations on new construction, demolitions, renovations, and upgrades of buildings within the district.
  • The Cappelman Building was built in 1921 and will turn 100 this year. (photos below)
  • Throughout its life, the Cappelman Building has housed a variety of shops and offices. Early on, it was referred to as the Clinic Building, most likely because several physicians leased space in the upstairs offices. From 1933 to 1953, the Winter Garden Post Office operated out of space on the first floor.

Historic Preservation Photo Contest Details

In conjunction with National Historic Preservation Month, The City of Winter Garden and The Winter Garden Heritage Foundation are sponsoring a Historic Preservation Photo Contest. This photo contest is open to all levels of photographers. To enter please send in your best photos of the structures and buildings in the Winter Garden Historic District. The top five photos will receive a $100 prize. There will also be many photos chosen to be on display at an upcoming art exhibit. For a chance to win please upload entries below by Friday, June 25th.

    Take a stroll through the historic district and photograph some of the historic structures/buildings listed below:

    Downtown Commercial District
    • Heritage Museum – 1 N. Main Street
    • The Cappleman Building – 121 W. Plant Street
    • The Edgewater Hotel – 99 W. Plant Street
    • The Garden Theatre – 160 W. Plant Street
    • The Birkett Building – 162 W. Plant Street
    • The Bond Building – 2 & 12 W. Plant Street
    • NY Bagel – 126 W. Plant Street
    • The Roper Building (WG Pizza Co.) – 36 W. Plant Street
    • Writer’s Block Bookstore – 32 W. Plant Street
    • Real Estate Collection – 100 W. Plant Street
    • First Baptist Church of WG – 125 E. Plant Street
    • American Legion Post 63 – 271 W. Plant Street
    • Winter Garden Masonic Lodge – 230 W. Bay Street
    • WG United Methodist Church – 125 N. Lakeview Avenue
    • Train Station/Museum – 101 S. Boyd Street
    • Old Fire Station – 127 S. Boyd Street
    Downtown Residential District
    • 57 N. Lakeview Avenue
    • 124 N. Highland Avenue
    • 128 N. Highland Avenue
    • 130 N. Lakeview Avenue
    • 136 N. Highland Avenue
    • 230 N. Highland Avenue
    • 104 N Lakeview Avenue
    • 125 N. Lakeview Avenue
    • 244 N. Lakeview Avenue
    • 234 N. Lakeview Avenue
    City Icons
    • Downtown Water Tower
    • Saddler Oaks on W. Plant Street
    • Lakeview Ladies (Oaks) on N.
    • Lakeview Avenue
    • Meadow Marsh – 940 Tildenville
    • School Road
    • Lakeview Middle School
    • Britt Mansion -1305 E. Plant Street
    • Winter Garden Masonic Lodge
    • Winter Garden Cemetery
    • West Orange Country Club Arch
    • Newton Park and Bridge
    • Downtown Street Bricks

    We would love to see all you photo entries on social media aswell. You can tag us on Instagram @officialdowntownwintergarden and use the hashtag #historicpreservationdtwg. To learn more about the City’s historic preservation efforts, please click here.


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