LONGWOOD HISTORIC DISTRICT

By  Mike Miller August 16, 2025

OVERVIEW

The Longwood Historic District in Longwood, Florida, is a charming slice of Old Florida that feels like a secret waiting to be discovered.

Just north of Orlando’s busy activity, this 190-acre gem, listed on the National Register of Historic Places since 1990, invites travelers to stroll through tree-lined streets and soak in the stories of a bygone era.

Longwood Inside-Outside HouseLongwood Inside-Outside House

With 37 historic buildings, including treasures like the Bradlee-McIntyre House, the Longwood Village Inn, and the Inside-Outside House, this district is a must for anyone craving a dose of history.

HISTORICAL SIGNIFICANCE

Longwood’s roots stretch deep, named by settler Edward Warren Henck (1846-1930) after a Boston suburb he helped design.

Longwood Henck HouseHenck House, Longwood

Founded in the 1870s, it bloomed as a winter retreat for wealthy northerners, thanks to the South Florida Railroad’s arrival in 1880.

The district’s centerpiece, the Bradlee-McIntyre House, a grand Queen Anne-style cottage from 1885, was saved from demolition in Altamonte Springs and relocated here in 1973, a testament to the preservation efforts of Grace Bradford and the Central Florida Society for Historic Preservation.

The Longwood Village Inn, once a 1930s gambling casino and later a 1950s umpire school, hosted a national governors’ conference in the 1920s, putting this small town on the map.

Senator Big TreeSenator Cypress Tree

Longwood’s history also ties to the Seminole people, who used the ancient Senator tree—lost to arson in 2012—as a navigational marker for centuries.

VISITING DETAILS

Find the Longwood Historic District near the intersection of State Road 434 and County Road 427, just a short drive from Orlando.

The district’s self-guided walking tour takes about an hour and covers all 37 contributing structures. The Bradlee-McIntyre House museum is open Wednesdays and Sundays from 1-4 PM, offering a peek into Victorian life.

Parking is plentiful near the SunRail station, which makes for an easy weekday visit.

INTERESTING FACTS

  • The Inside-Outside House, built in 1873, was a prefabricated home shipped from New England, designed like a whaling ship with external support studs.

  • Local legend claims the Inside-Outside House is haunted by its original owner, a sea captain, and his cat, Bruno.

  • The Longwood Village Inn starred in the 1966 film Johnny Tiger, standing in for a fictional South Florida town.

  • Longwood’s early economy leaned on a sash, door, and blind factory owned by Russian expatriate Pyotr Dementyev, later known as Peter Demens who later became a railroad pioneer and the man who brought the railroad to St. Petersburg, named after his Russian home town.

    • WEBSITE FOR LONGWOOD HISTORIC DISTRICT

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