(Autopro Professional Auto Service & Conway's Home Furnishings)

The Chevrolet logo is still visible above the old dealership built in 1924 on Magnolia Street between 2nd and 3rd streets. The business was started as a Ford dealership in 1922 by Jacob H. Butler.

For years, the building carried a Ford symbol – even after the business became Butler Chevrolet in 1927. In the 1950s Daily Commercial writer Emmett Peter asked Jacob's son Otis why the dealership still carried the Ford logo on the building.

"He told me the family had never gotten around to changing it since the building was erected in 1924," wrote Peter, "but everybody knew that his father was too penurious to pay for changing the big letters atop the building. Anyway, people could look through the windows and see that they were selling Chevys."

It was the first Ford and Chevrolet dealerships in Leesburg.

Butler's sons, Otis, Marvin and Herbert, joined as partners in the dealership after it became Butler Chevrolet. The dealership closed in 1972.

(Formerly C.D. Kirk Chrysler Dealership and Leesburg Commercial)

This antique emporium that extends from Orange Avenue to Seventh Street was originally a Chrysler dealership.

It was built in 1926 by the C.D. Kirk Company, a Chrysler distributor. The car dealer didn't have far to move. It was originally located on the northeast corner of Main Street.

The new building was constructed of brick, concrete and steel and was built so an additional three more stories could be added at a later date. It cost in the vicinity of $50,000, with an "Old Spanish motif its dominating note."

The Seventh Street end of the building was covered almost entirely of plate glass because that's where the vehicles were showcased. The service and storage areas were accessed by the Orange Street entrance. In between the two sections were other rooms for storage and other purposes, as well as showers for employees and restrooms for guests.

The showroom floor was made of red tile set in black mortar. And the walls were covered with "pecky cypress, with bolt-studded cypress doors and massive wrought iron hinges."

C.D. Kirk didn't stay long. The Sanborn Map of 1929 shows it was home of the Leesburg Commercial, which stayed there until moving to its present location in 1965.

Leesburg City Hall was completed in 1926, more than 50 years after the city was incorporated in 1875. During those five decades, Leesburg's government had many homes.

Originally, the commission met on the first floor of the Masonic Lodge, then on the northwest corner of Orange and Fifth streets. Later, City Hall was moved into the old Sumter County Courthouse after Leesburg lost the county seat. The last temporary City Hall was in upstairs offices in the old Armory Building on the northeast corner of Fourth and Main streets.

Citizens passed a $60,000 bond issue for the construction of City Hall. In addition to housing city government, it was also home to the police and fire departments. Two of the three bays used by those departments are visible on the east side of the building, across from the library.

City Hall was designed by Alan J. MacDonough, an architect with an office on Main Street. Locally he also designed the Historic Lake County Courthouse, Eustis City Hall, Clermont High School, Eustis Grade School and the Masonic Temple at the corner of Fifth and Main streets in Leesburg.

Work on expansion of City Hall was completed in 1988, doubling its size. Bricks were gathered from the original brickyard in the expansion. It was a $1.5 million project.

(Formerly the Fain Theatre)

The Tropic Theatre was originally called the Fain Theatre when it was first opened in 1936 by Earl Fain. The marquee on the billboard along Main Street let those passing by know that "Collegiate" was playing, starring Frances Langford.

Fain had been the assistant manager of the beautiful Fox Theater in Atlanta. He moved to Leesburg in the 1930s and took over the Palace Theatre just a few blocks away on Main Street and built the Fain Theater a few years later. The Palace Theatre had opened in 1923.

The Palace and Tropic theaters were just two of the movie houses Fain acquired for his "Fain Circuit." His chain began as the Fain Road Show as he traveled to small towns with portable equipment and literally "took the show on the road" during a series of one-night stands around Florida.

Hugh Martin and his son-in-law Bill Cumbaa took over the movie chain when it had eight theaters. The Fain Theatre was remodeled and reopened in 1960 as the Tropic Theatre and the Palace was closed – never to reopen.

The Tropic was once again remodeled and expanded and reopened as the Tropic Twin Theatre in 1979. Cumbaa got out of the business in 1985. Since then, there have been several operators. And it has been several years since the last movie was shown at the Tropic Theatre.

(Also First Federal Savings & Loan of Leesburg and Jewelry Works)
400 W. Main Street

Leesburg residents shook their heads in 1906 at the price paid by the new Citizens Bank of Leesburg officials for the property on the northeast corner of Fourth and Main – $500. The town was aghast at that outrageous amount," said George Rast, who began working for the bank in 1922.

A 27.5-feet by 35-feet brick building was constructed for the cost of $2241. The bank grew steadily over the years and in a little more than 10 years bank officials realized a larger facility was needed. They agreed to buy the adjoining lot for $1,200. Again, folks were appalled at the cost.

The new two-story building with two columns in the front replaced the small brick building in the corner of Fourth and Main in 1917. The bank also had a new name to go with its new facility. It became First National Bank of Leesburg, complete with a national charter on July 18, 1917. The Leesburg bank was the first in the state with a female cashier when they placed Ruth Bourlay in that position while working in the new facility. Later, Jo Letton Kramer become the first full-time woman teller, possibly in the country.

By the fall of 1936, bank officials realized they had just about outgrown their two-story building. Initial plans called to renovate the two-story building on Fourth and Main. During renovations, the staff moved to the old five-story Leesburg State Bank building which opened Aug. 25, 1926. Plans were to only rent the old State Bank building but that soon changed because Ware liked it so much and decided to stay.

First National sold its old building to First Federal Savings & Loan. Chet Blackmon and his partner bought the building and renovated it in 1987.

(Also formerly Leesburg Elementary School and Lee Adult Opportunity School)

Lee School holds fond memories for many Leesburg residents who passed through the doors of the venerable old school as students.

Longtime Leesburg educator Nelle Skeen began her Leesburg education career 1914, a year before Lee School was built.

Skeen moved to Lee School after it was completed the following year. She reminisced about the construction of the new school in Through Schoolhouse Doors: "If you did not live through that period when Lee School was actually being built, you cannot appreciate the joy of anticipation we felt as we walked – as we did almost every day – over the field to see how many more red bricks had been put in place since the last trip. The huge building, the auditorium, the tall smoke stack – all sent never to be forgotten thrills through each heart."

Lee School was constructed in the spring of 1915 at a cost of $40,000 including land. It originally had twelve rooms with the auditorium as a separate building. Grades 1-12 were housed here until 1918, when the north building was built in a colonial-revival style. By 1923, they needed more space and 12 classrooms were added to the north building.

The facility served as an elementary school until 1974. During the early years it was used as a meeting place and a hurricane shelter. It served for years as Lee Adult Opportunity School and is currently being used by Leesburg High School during the high school expansion.

(Formerly Leesburg State Bank)
601 W. Main Street

The building on the southwest corner of Main and Sixth streets now occupied by Doggibags was reportedly Leesburg's first brick building when it was constructed in 1886 and it opened as a bank.

The bank was opened April 1, 1886 by Morrison, Stapylton and Company Bankers and later became Leesburg State Bank.

Leesburg State Bank later built a new facility across Sixth Street, now called the LifeStream Building. And the bank moved across the street on the 40th anniversary in 1926.

Leesburg State Bank went into receivership after the bank moratorium of 1933 and never reopened. First National Bank, later a part of SunTrust, moved into that building in 1936.

According to a newspaper story written during the opening of the new facility, the old bank building, now Doggibags, was remodeled to become "another site for a good business house in Leesburg." Satisfied Doggibags customers would agree that it has.

(Formerly Leesburg Woman's Club and Lassiter-Ware Insurance)

Work started on this Spanish Mission Style building, now home of the Leesburg Heritage Society and Museum, in 1921 by the Leesburg Woman's Club.

Construction was completed in 1922 and the structure at 111 S. Sixth Street remained the Woman's Club gathering place until 1946, when it was sold to Paul Lassiter. Many Leesburg residents remember the building as Lassiter-Ware Insurance, which remained in it until Sun Bank began leasing the building in the 1970s as a branch office and drive-up window.

The city purchased the building and property in 1981 and used it while City Hall was being renovated several years later.

The Woman's Club was very generous with its facility and the building also used at various times by the town library, the Chamber of Commerce and the Catholic Church.

And many a Leesburg resident remembers attending civic meetings and social events such as proms and dances in the auditorium on the second floor.

The Leesburg Heritage Society and Museum moved into the building in 1990 and remains there. The Leesburg Partnership, which is dedicated to the revitalization of Leesburg, moved into the building in the early 1990s.

(Formerly the Mote Block and Stoer Block)

Edward H. Mote and his partner, Gen. Davis Tillson, helped changed the face of downtown Leesburg when they built the 22,000-square-foot Mote Block, Leesburg's largest building.

Located on Main Street between Fourth and Fifth streets, today the two-story building is call the Leesburg Opera House. Originally the site of the Sumter County Courthouse, the town acquired the property and moved the old courthouse in the 1880s close to where the city library is now located.

In order to get the property for the Mote Block, Tillson and Mote had to agree to build a new brick hotel that cost no less than $15,000. That Hotel was the Lake View. It was completed by Jan. 6, 1890, about six months before the Mote Block was finished.

Businesses filled space on the first floor and the upstairs had offices facing Main and Fifth streets. The original second floor entrance and stairway was in the middle of Main Street side. The Opera House was located in the southeast corner of the building.

Edward H. Mote and his wife Lucretia bought the property at 1021 W. Main Street from John Love in February 1889. The Victorian-style house was completed in 1892 for about $9,000. The house had a nursery, but the Motes remained childless and sold the home to Bishop Henry Clay Morrison in 1908, who bought it as a retirement residence.

Morrison made many improvements to the house, including the addition of electricity by his son, Dr. H.K. Morrison, who birthed about 3,000 Leesburg babies.

The house was sold to John S. and May James Morris in 1918. A member of the Morris family lived in the house for the next 70 years. They added indoor plumbing in phases.

Son Robert moved his family into the house to care for his aging mother May in the mid-1950s. His father, John S. Morris, died several years earlier. When May J. Morris died in 1973 the house was willed to Robert and Georgianna. The Mote-Morris House was placed on the National Register of Historic Places the following year.

The Mote-Morris House was purchased by Morrison United Methodist Church in 1988 and the church offered the house to whomever would move it. The house was relocated from 1021 West Main Street to 1195 West Magnolia Street in 1990. The community raised $95,000 so the house could be moved.

204 N. Lee Street

Most of the beautiful interior of the Gothic Florida style wooden St. James Episcopal Church that was built in 1889 was destroyed by the blaze that swept through the historic landmark on Aug. 15, 1947. The fire started in the northeast corner of the venerable old church and had been smoldering for quite some time, according to Fire Chief "Bunny" Stevens. The church was extensively rebuilt. It's possible to walk under the church floor and see the flooring that was not burned through but see the scorched wood.

By 1885, Leesburg was a thriving community of about 1,500 people, and already had Methodist, Baptist and Presbyterian churches lining Main Street and the English settlers in the area wanted a church for Anglican worship. A notice appeared in the Nov. 12, 1885 Daily Commercial and invited those interested in starting an Episcopal Church in Leesburg to meet at Earman's Hall for the purpose of discussing the possibility of organizing an Episcopal Society in Leesburg.

The Leesburg mission began growing almost immediately. Early church services were held in homes of members, community buildings such as the school, and the Presbyterian Church. A report given during the convention held in Palatka early the next year stated, "Services are exceedingly well attended, 157 persons have attached themselves to the mission, and a good choir has been formed. A large confirmation class is being organized, and the people expect to build a church within a year."

The sanctuary was built in 1889 by J.H. Richards for $1,400 and the first service was celebrated Sept. 1, 1889 by The Rev. Joseph E. Julian, the church's first resident priest. After the fire all energy was directed toward the rebuilding effort. The damaged building was moved 20 feet north and rebuilt on a new site. The plan called for lengthening the altar, nave and chancel areas, and widening the church by four feet on each side. The work was done by Jobbins Construction Company and the building was ready for Easter Service in 1948. The remains of the original altar were incorporated in the new one and the stained glass windows above the altar were made from pictures of the original ones.