The 150 Year Journey To Southern Oaks
Coveted Land
Long before there were streets named Sweetbriar, Wald, Montcalm or Ridgecrest—and long before Orlando had become a city—the area around what is now Southern Oaks was part of a wilderness of pine forests, oak hammocks, lakes and sandy trails. The landscape was shaped first by the Indigenous people who traveled through Central Florida, and later by soldiers, surveyors, pioneers, citrus growers and some surprisingly prominent American families.
In many ways, the story of Southern Oaks begins not in 1969, but more than a century earlier.
The Old Trail Through the Wilderness
One of the most important features of early South Orlando was a route that eventually became known as the Fort Mellon to Fort Gatlin Road.
The road followed an older Indigenous trail and became part of the military route connecting Fort Mellon, near present-day Sanford, with Fort Gatlin, the U.S. Army post established south of the future city of Orlando during the Second Seminole War. Fort Gatlin was chosen as the site for a fortification as it laid between three lakes, allowing for better strategic defense and movement of supplies to the Fort. As with all forts in the day, they were spaced apart so that a caravan could make it from one to the next in one span of daylight to avoid attacks by native Indigenous peoples. Surveyors and settlers later followed the same route to Fort Gatlin as they began mapping and occupying Central Florida.
The route through Southern Oaks was a rough trail through pine woods, sand and wetlands, with travelers navigating by the natural features of the landscape. The lakes were landmarks, the oak trees provided shade, and the trail itself was one of the few practical ways to move south from the developing settlement around Orlando.
Today, much of the surrounding landscape has been transformed by a modern city. But the geography that guided those early travelers is still here.
The Mystery of Council Oak
Perhaps the most intriguing story connected to the land around Southern Oaks concerns a magnificent live oak known as Council Oak. According to Orlando historian Kena Fries, an enormous live oak once stood beside the old trail near Lake Pineloch. On the west side of Pine Loch Lake, where the old trail wound its way thru the pine woods, there once stood an immense live oak, said in its glory to have been the largest live oak in all of central Florida. It was known as “Council Oak”, the gathering place of the Seminole warriors. Here it is stated on what seems to be reliable authority, was planned the Dade Massacre and many other sudden attacks on the early settlers.” The “old trail” was indeed on the west side of the lake, but the Council Oak is believed to have been on the east side of the lake.
The precise location of the tree has been debated by later historians, and that uncertainty is part of the story. What is not in doubt is that the Lake Pineloch area was situated along the old Fort Mellon–Fort Gatlin route and that local historians preserved the memory of a remarkable ancient oak associated with the Seminole era.
By the early twentieth century, Council Oak was gone, having been struck by lightening. But it did not disappear entirely from history. The celebrated Orlando artist James M. Alden, who lived on Lake Pineloch, painted the tree. His painting may have preserved one of the few visual records of this remarkable piece of Central Florida's early history.
A Jefferson Lived on Lake Pineloch
Civil War followed by a protracted “Reconstruction Period” was finally in the past as spring of the 1870s brought signs of new life in Central Florida. After a long-decade of human tragedy however, a time during which neighbors were often pitted against neighbors, Orange County was still in turmoil, an example being the 1870 killing of Sheriff David Mizell.
But a new clan had arrived, bringing with them a newspaper correspondent who began telling the world of the good, the bad, and the ugly of Central Florida. “Orlando, the county seat,” wrote correspondent Will Wallace Harney soon after passing through town in 1869 on his way to a Lake Conway homestead, “resembled a rickety barnyard an hour after Sherman’s bummers had passed.” Smoldering ashes of Orange County’s burnt courthouse ruins no doubt reminded the former Kentuckian of how Sherman had left Atlanta, after-all, Atlanta had been one of the war-torn towns Harney traveled through a year prior on his way south to Florida.
The War had ended, but news of a dead Sheriff, and then discovery of a floating body in Lake Conway, a stone’s throw from Harney's cabin, gave him much to write about.
Heading towards modern day Southern Oaks in 1871 from what is now downtown was a wilderness five miles long ending at a fine new Lake House, the Francis W Eppes home. It was a "gate house" of sorts that welcomed travelers to a hopeful new settlement – Fort Gatlin. A bit further south along the trail were the homeplaces of William M. Randolph and Ouachita Pushmataha Preston. Through an imaginary fortress gate and beyond, yet another lake further south were the homesteads of William B. Randolph, Nathaniel Randolph (who was also murdered shortly after arriving in central Florida), and Will Wallace Harney. And almost as if serving as a corridor, connecting each of the above homesteads, was the homestead of William A. Patrick, one of the original pioneers dating to the 1840s.
Pioneer settlers however were not the only trail trekkers. Will Harney wrote of “correspondents, artists, scientists, and hunters” each passing through on their way to the Everglades. Harney even named a few of the “groups," such as the “New York Party,” and “the Western Party.” Word had spread near and far of the great hunting and exploring region around Fort Gatlin, a vast wilderness well-known to a trusted friend and confidant of Will Wallace Harney, Surveyor Benjamin F. Whitner. As the first surveyor to traverse nearly 600 square miles to the south of Orlando, Whitner had accumulated nearly 300 acres on two side of Lake Gatlin prior to the War. And then after War’s end, Whitner settled at Fort Reid – or Sanford as it is known today – while at the same time introducing the Randolph clan to Fort Gatlin. Whitner kept his Lake Gatlin acreage too, all the while promoting a dream of his - connecting Lake Monroe with Tampa Bay by a railroad.
The bravest of brave settlers, some newcomers to Florida, others long-time residents, but together they chose to develop a region rich in lakes to the south of Orlando. They built "castles of pine" on Lakes Pineloch, Gatlin, Holden, Jennie Jewel, and the two largest bodies of water, Conway, and Hogan. All but one of these named lakes of the 1870s survived to this day, but Lake Hogn was renamed Lake Jessamine.
Francis Wayles Eppes VII who built this new Gateway Home on Lake Pineloch was the grandson of Thomas Jefferson. You pass by this house every time you head to the post office or the grocery store.
Eppes was born in 1801 to Maria Jefferson and John Eppes and spent part of his childhood under the influence of his grandfather, Thomas Jefferson. He later became an important civic and educational figure in Florida, serving as mayor of Tallahassee and helping establish the institution that became Florida State University. After the Civil War, Eppes moved to the Orlando area. In 1869, he settled on Lake Pineloch, where he established a citrus farm and built his home, Pine Hill. Construction of the residence began in 1871. At the time, this was not a fashionable Orlando suburb. Orlando itself was still a small frontier community, and the land south of town was largely wilderness, lakes, groves and scattered pioneer settlements. The Eppes home on Lake Pineloch nevertheless became an important gathering place for the community. Early Episcopal worship services were held there, making Eppes one of the founders of what eventually became Orlando's Cathedral Church of St. Luke.
Before Eppes established his home, a 160-acre parcel on Lake Pineloch had been acquired in 1860 by Isaphoenia Cleopatra Ellington Speer, an extraordinary but largely overlooked figure in Central Florida history. Isaphoenia was the wife of pioneer James G. Speer, one of the people most closely associated with the founding of Orlando. But she was far more than simply the wife of a prominent pioneer. In her own name, Isaphoenia acquired substantial amounts of land in Central Florida. Historical research indicates that by 1860 she held nearly 1,700 acres in Orange County, making her one of the area's largest landowners at a time when women were seldom the sole owners of major tracts of property. One of those properties was the 160-acre tract along Lake Pineloch including modern day Southern Oaks.
A Remarkable Family Connection
The Eppes family story did not end with Francis Eppes. Three of his daughters married three brothers from the Shine family, creating one of the most prominent family networks in early Orlando. The Eppes and Shine families became deeply involved in the civic, religious and commercial development of the young community. The connection is visible in Orlando even today. The Eppes-Shine family plot at Greenwood Cemetery has been recognized with a Florida historical marker honoring the descendants of Thomas Jefferson and the families' contributions to the development of Orlando.
One member of the Shine family, Captain Thomas Jabez Shine, became a prominent Orlando businessman, banker and civic leader. His home on Orange Avenue was reportedly the first Orlando residence to have an indoor bathroom—and he named Jefferson Street in honor of his wife's Eppes family.
That seemingly small detail says something about the world surrounding Lake Pineloch in those days. These were not anonymous settlers. They were families whose names, relationships and businesses helped shape the emerging city.
Imagine Southern Oaks Before There Were Houses
It is difficult today to picture what this area looked like before development.
There were no subdivision streets.
No sidewalks.
No walls.
No driveways.
No neighboring houses.
Instead, there were pine woods, enormous live oaks, citrus groves and the lakes that had drawn people to the area for generations.
The transition from wilderness to neighborhood did not happen overnight. The land passed through generations of owners and uses before it eventually became part of the modern city.
A Place Connected to the Birth of Orlando
Some of the people associated with the land around Lake Pineloch were also directly connected to the founding of Orlando itself.
Isaphoenia Speer was the wife of James G. Speer, one of the men most closely associated with the establishment of Orlando. Her half-brother, Benjamin F. Caldwell, was also an important early figure in the town's development. Historical research traces their family relationships through the pioneer families who were acquiring land throughout what was then the largely unsettled southern portion of Orange County. The result is a remarkable geographic coincidence. The land that would eventually become Southern Oaks lies within a landscape that was simultaneously being explored, surveyed, settled and developed by many of the same families responsible for creating the city of Orlando.
Southern Oaks did not simply appear on the outskirts of Orlando. It grew out of the same pioneer landscape that produced Orlando itself.
From Wilderness to Neighborhood
By the middle of the twentieth century, the character of the area was changing again. The citrus industry had declined from its earlier dominance, Orlando was expanding rapidly, and land that had once been agricultural or wooded was becoming increasingly valuable for residential development. The transformation eventually produced Southern Oaks.
But the neighborhood inherited more than a piece of real estate. It inherited a landscape with a history stretching from Indigenous trails and the Seminole Wars through pioneer settlement, citrus cultivation and the growth of Orlando. The mature oaks that define Southern Oaks today are therefore more than beautiful landscaping. They are reminders of a landscape that existed here long before the neighborhood did.
A Neighborhood Built on Layers of History
Civil War followed by a protracted “Reconstruction Period” was finally in the past as spring of the 1870s brought signs of new life in Central Florida. After a long-decade of human tragedy however, a time during which neighbors were often pitted against neighbors, Orange County was still in turmoil, an example being the 1870 killing of Sheriff David Mizell.
But a new clan had arrived, bringing with them a newspaper correspondent who began telling the world of the good, the bad, and the ugly of Central Florida. “Orlando, the county seat,” wrote correspondent Will Wallace Harney soon after passing through town in 1869 on his way to a Lake Conway homestead, “resembled a rickety barnyard an hour after Sherman’s bummers had passed.” Smoldering ashes of Orange County’s burnt courthouse ruins no doubt reminded the former Kentuckian of how Sherman had left Atlanta, after-all, Atlanta had been one of the war-torn towns Harney traveled through a year prior on his way south to Florida. The War had ended, but news of a dead Sheriff, and then discovery of a floating body in Lake Conway, a stone’s throw from Harney's cabin, gave him much to write about.
A History Rooted In The Birth of Orlando - the 1900's
Southern Oaks has been considered prime real estate since the earliest days of American settlement. It lays just north of the old homestead of Judge William Randolph (father-in-law of both clerk of courts Benjamin Robinson and the well-known writer Will Wallace Harney of Pine Castle) and just east of the homestead of Dr. Ouachita Pushmataha Preston (whose wife Jennie Preston was the namesake of Lake Jennie Jewel). The Eppes family, descendants of President Thomas Jefferson, also lived in the vicinity.
In the 1880s, the South Florida Railroad pushed thru Orange County with the financial backing of Boston capitalists. They encouraged their fellow New Englanders to follow the new line and acquire some of the fertile grove land along its route. One of these was William Henry Odiorne, who acquired the site of what would become Southern Oaks.
Mr. Odiorne was born in Boston on 7 September 1833, and was educated at Harvard University. As a young man, he worked as a surveyor and lived for a time in Chicago, Illinois. On his new property in Orlando, he established an orange grove. But, he and his wife were not year-round residents, entrusting management of the grove to local superintendents.
Mrs. Odiorne was a faithful member of the First Baptist Church of Gloucester, Massachusetts, and contributed the following recipe for orange marmalade to a fundraising cookbook published by the church in 1900: “Wash the oranges and slice very thin, rejecting the seeds. To each pound of the fruit add three pints of cold water and let it stand twenty-four hours, then boil until the skin is tender. Allow them to stand until next day, then weigh, and to every pound add one-and-one-half pounds of sugar. Boil until the syrup jellies and the chips are tender. Six oranges take three quarts of water and seven pounds of sugar.”
She probably perfected this recipe during the winter months the Odiorne family spent on their grove land. Mr. Odiorne died on his Orlando property on 31 January 1905, after which his widow and children began selling off parcels of the grove. The portion that became the site of Southern Oaks was acquired by John and Elnora Caplinger in 1916, but they only held it for a short time before reselling it to Rev. Robert Campbell Anderson, Jr.
Rev. Anderson eventually acquired most of the parcels that formerly belonged to the Odiornes, consolidating them as Anderson Grove, Inc. But, like the Odiornes, he was primarily an absentee landlord. Rev. Anderson was the son of Robert Campbell Anderson, Sr., pioneer Presbyterian minister of Martinsville, Virginia. He followed in his father’s footsteps and pastored a church in Charlotte, North Carolina. He later became president of Montreat College, and wrote a history of that institution in 1949.
Rev. Anderson died 20 February 1955. His wife Sadie Gaither Anderson survived him until 3 October 1962, after which the grove was deeded to a trust that developed Southern Oaks as a residential subdivision. The Andersons are buried in Charlotte. Rev. Anderson acquired individual parcels of what is now Southern Oaks as early as 1913, 1917, 1921, and 1934. There was an old “grove house” on this land near 3224 Wald Road (Edgecliffe to Wald Road somewhere at the first bend where Wald Road changes from West/East to North/South).
In 1952 R. C. Anderson transferred parcels 4, 5, and 6 to Anderson Grove, Inc. R. C. Anderson acquired parcels 1 and 2 in 1925 by means of a tax sale. He diligently kept paying the taxes on this property, when in 1965 he was sued by the heirs of Frances Foster who wanted to reclaim the property. He finally won the suit and now possessed parcels 1-6 of the land, which eventually became Southern Oaks.
In 1967 Anderson Grove, Inc. secured a mortgage with the Orlando Bank & Trust Company for $400,000 to start to develop the land. Anderson also granted a trust, Southern Oaks, to Austin A Caruso, John J. Walsh and W. Russell Anderson. The trust granted the City of Orlando easements to construct sewers, drainage, and roads and thus was granted permission to start the development of the Southern Oaks Subdivision.
The covenants for Southern Oaks were recorded in 1968 and the Southern Oaks Declaration of Restrictions were recorded in 1969.
The first house built in Southern Oaks was 1201 Montcalm Street, built in 1969. The second floor railing used to be New Orleans style wrought iron. It was once owned and occupied by longtime Orlando Mayor Buddy Dyer. The Weston and Agnes Thomas Family have lived there for decades.
The first family to move into Southern Oaks was the Victor Smith Family. Janet Smith, our original Southern Oaks resident still lives there. Her husband, Victor passed away in 2023.
The Hurricanes
On 13 August 2004 about 9:30 PM, Hurricane Charlie, a category 4 storm, passed directly over Southern Oaks. Buckwood Drive looked as if a tornado passed right down the street. Trees were down in all directions and as the neighborhood awakened the next morning, the residents came out of their homes completely stunned. No one could believe what had happened over night. It was a bitter/sweet time, and many of us finally met our long time neighbors as we inspected the damage. We even formed a large circle of prayer in the middle of Northglenn and Buckwood Drive while surrounded by fallen trees; after all, no one was going anywhere. Estimated damage for Florida was $14 billion and 27 people were killed.
On 5 September 2004, Hurricane Frances struck Southern Oaks. Frances was a slow moving storm leaving tremendous devastation. Southern Oaks was hit hard, power was lost; however, many of the trees had already been downed by her predecessor. Estimated damage for Florida was $10 billion and 3 people were killed.
On 15 September 2004, a third Hurricane, Ivan, a category 3 storm passed through Orlando. Estimated damage for Florida was $20 billion and 20 people were killed.
Incredibly, on 25 September 2004 we received the fourth hurricane within a 6 week period, Hurricane Jeanne, a category 3 storm. Estimated damage for Florida was $12 billion and 6 people were killed.
As a result of the 4 storms, 400 large truck loads of tree debris were removed from Southern Oaks. The sounds of generators were heard for weeks and many of the largest laurel and water oak trees in the neighborhood were lost. Overall, approximately one out of every five homes in Florida was damaged by the 2004 hurricane train. With roads blocked by trees and no power, Some Southern Oaks neighbors took to riding bicycles to areas with power and food to bring back burgers and supplies to neighbors. Every neighbor with a chainsaw took to the streets to help free each other. In its darkest times, the residents of Southern Oaks became closer than ever and the blessings of a good neighbors shone through.
Orlando Sentinel Article
Grove to Southern Oaks
Grove Gave Root To Way Of Life
Southern Oaks Takes Pride
In Its Neighborly Manner
January 4, 1987 By Joe Kilsheimer of The Sentinel Staff
In the boom of the late 1960s, the place to move in Central Florida was south Orlando. It attracted the lion’s share of the corporate transferees coming to work for Martin Marietta, Walt Disney World and the Apollo space program. It was during 1969 when a group of Orlando citrusmen started developing a 107-acre orange grove. The northern half of the property was just south of Pine Loch Lake. The developers named the project Southern Oaks — appropriate since the south end of the property was a sprawling oak hammock. Austin Caruso Jr., who headed the development team, said the partners — his father, Austin Sr., Russell Anderson and Bob Hester — thought the development would turn out to be like many others in south Orlando: moderately priced with medium-sized, no-frills houses.” We didn’t expect that it would turn out like it did,” Caruso said. ”But when we saw that we were getting bigger and more expensive houses, we changed strategies a little bit. We started making the lots a little bigger.” As it turned out, Southern Oaks developed into a close-knit neighborhood of upscale houses. And it came to serve as a prototype for other luxury home communities in Central Florida.” It really was one of the first new custom-home developments in the area,” said Michael Ashington-Pickett, a veteran Central Florida home builder and a Southern Oaks resident for more than 10 years. Today, Southern Oaks has become one of Central Florida’s most desirable addresses. Former Florida Gov. Reubin Askew, who moved to Orlando from Miami in early 1986 to open a branch of his Miami-based law firm, lives in Southern Oaks. The neighborhood also is popular with physicians. One resident estimated that more than half of the homeowners there ”are associated with the medical industry in Orlando in some way.” The development is about two miles southeast of downtown Orlando, reachable from the city’s main roads via quiet, two-lane arteries such as Ferncreek Avenue and Gatlin Avenue. There are entrance off Summerlin and Pershing avenues. Homes in Southern Oaks, which sold for $70,000 and $80,000 when they were built in the early 1970s, now sell between $180,000 and $220,000. That, of course, is if their owners sell them at all.” You couldn’t get my wife out of this subdivision with a crowbar,” said Frank Anderson, a custom-home builder and a Southern Oaks resident for the past nine years. ”She loves it here.” Anderson’s comments echo those of many Southern Oaks residents. They often characterize the development of roughly 210 homes as a ”traditional family neighborhood.” Ashington-Pickett, who built many of the houses there, said, ”It has more of that old American character than most neighborhoods I know. It’s a nice place to bring up kids.” Parents, he said, also like the fact that children from Southern Oaks attend long-established public schools such as Pershing Elementary, Memorial Junior High and Boone High schools. Caruso attributed Southern Oaks’ popularity with upper-income buyers to its physical characteristics such as the stonework entrances, a small fountain near the middle of the development and the fact that all of the utilities are underground, an uncommon trait for subdivisions in the late ’60s.”Having all-underground utilities was rare for those days,” Caruso said. ”Most of the developments in that part of town were on septic tanks, but we wanted sewage treatment capability because that helped promote a feeling of quality.” Caruso also recalled that developers and residents resisted calls by city officials to install more than two entrances into the neighborhood. Although all of the roads within Southern Oaks are public, the development has a feeling of separateness from the rest of the city, which Caruso said helps foster a spirit of community within the neighborhood. Residents said that spirit shows up in several ways. Anderson said residents hold a neighborhood picnic in a vacant lot near his house every July 4th weekend. The event is loosely organized, but well attended, Anderson said. Ashington-Pickett said that several days before Christmas, ”We heard a knock on the front door, and there were 15 Christmas carolers. They just stood there for five minutes and sang Christmas carols to us. How many other neighborhoods do you know where the people still go around singing Christmas carols?” Ashington-Pickett also gave credit to the Southern Oaks’ homeowners association, which he said ”goes about its job quietly and gently.” As one example, the homeowners association has decided to maintain the small fountain that serves as a centerpiece in the development, although the job is one that requires constant attention, Caruso said.”We (the developers) almost decided to take the fountain out at one point because it was getting to be a real nuisance,” Caruso said. ”It requires a lot of upkeep.” But the people . . . got together and decided they wanted to keep it because they think it enhances the whole neighborhood. That’s the kind of place Southern Oaks is.”
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