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Enterprise/Stone Island

Historic Enterprise: Birthplace of Southwest Volusia County

At a time when Miami was not yet on most maps, adventurous travelers from as far away as England were boarding steamboats at Jacksonville for a new and wild destination on the St. John’s River called Enterprise—“the furthermost outpost of civilization…on the verge of savagism”. Flowering Jasmine and Hibiscus curtained the riverbanks, the air wafted with the smell of orange blossoms, and clouds of Egrets and Ibis rose from the Cypress trees as the boats passed by.

In these early 1840’s, travelers stayed at Cornelius Taylor’s “Hotel for Invalids” perched high on the shell mound of old Enterprise, while later the Brock House offered improved accommodations a mile further west on the lakefront, where the Methodist Children’s Home sits today. But even before Enterprise was discovered by steamboat travelers, the area had been a crossroads of military activity. Fort Kingsbury, situated on the lakefront, was a garrison for soldiers scouting Indian activity in the second Seminole War. 

Some of the early stagecoach roads followed paths that were already ancient when Europeans arrived, such as Chocochatty Trail along the river from lake George to Lake Monroe. Stone tools and spearheads left by native Timucuan Indians show this area was inhabited 6K years before the Spanish sighted land.

Garfield, then called Mossdale, was an early black community off Old Titusville Road until the 1930’s. Approximately 200 freed slaves from the New Smyrna area settled it during the Reconstruction Period following the Civil War. Garfield had a general store, church (still standing today), cemetery and train depot. 

In 1843, William Fail, one of the first homesteaders, claimed 160 acres under the Armed Occupation Act and called this land Fail’s Island. Today this is known as Stone Island. Enterprise was the county seat three times: First in 1843 of Mosquito county; in 1845 of reorganized Orange County; and in 1854 of Volusia County. Enterprise was incorporated from 1877 to 1895. 

Today, Enterprise is a charming little bedroom community consisting of subdivisions like Stone Island Estates along Lake Monroe, to country homes on large acreage, to bungalows on the original footprint of historic Enterprise. Regardless of where you live, you will enjoy bountiful nature along with great boating and fishing. It is a short commute to the hustle and bustle of Orlando or Daytona Beach and the Central Florida Zoo and Gemini Springs State Park is just down the road. The Tracks to Trails bike paths offer the best biking in Florida with miles and miles of paved biking paths shaded by the canopies of huge oak trees. Green Springs Park is also located in the heart of Enterprise and is a lush oasis of natural springs and Old Florida at it’s very best—take a hike over the charming wooden bridges and enjoy Mother’s Natures work. 

If you’d like to know more about Enterprise, be sure to stop by the Enterprise Heritage Center where you can see a full display of photos and artifacts from the area—it is a must see! Call us today if you’d like to explore Enterprise as your next home—we are experts in the area!  



As the Anchor of Historic Enterprise, Stone Island Estates is truly a special place to live and play. With 1100 acres and 237 homes nestled on the Northeast shore of beautiful lake Monroe on the St. John’s River, Stone Island is a nature lover’s paradise and the hidden gem of Volusia County. Soaring eagles, sandhill cranes, peacocks, ancient oak trees dripping with moss, and the beauty of Lake Monroe is yours every day a Stone Island resident. With all homes sitting on at least 1/3 of an acre, you can enjoy great neighbors AND a little bit of privacy, not to mention the vast amount of parks and green space beautifully maintained by the HOA for all to enjoy. 

Stone Island also offers some great amenities. At the center of the Island sits an equestrian area, complete with a barn, training field and plenty of room for your horses to roam. 

If you love to fish, you can launch your boat at the convenient community boat ramp and sail out to Lake Monroe which is part of a larger chain of lakes that will lead you all the way out to the ocean if you’re feeling adventurous. 

Stone Island is an active golfcart community that hosts lots of fun activities like an Easter Egg Hunt, 4th of July Parade and Celebration, Halloween Party; Santa Clause visits, community garage sale, trading treasures community day, sponsorships of needy families/organizations, and so much more. 

The Picnic Pavilion in the park area near the boat ramp can be used for special events by Stone Island residents. The pavilion includes picnic tables, electric and water hook-ups, and a brick base for removable barbeque grills and a new firepit.

Lazy days on the lake, sunsets that will take your breath away and a sense of community are what Stone Island living is all about. If you’d like to check out Stone Island for your next home, let our team know—we are the Island experts and have been residents ourselves!


Events and Places of Interest:

Enterprise Heritage Center (360 Main Street, Enterprise, FL)

Housed in the historic Enterprise Elementary School (1936) the building is a permanent display place for the extensive collection of historic letters, documents, photos, artifacts and other material owned by the Enterprise Preservation Society.  The building features a 1930s era classroom, works by local artists, and a community meeting place.  Enterprise was originally the site of a booming tourist industry during the Steamboat Era.