Longwood Historical Trail

This was originally posted to Geocities but was removed from the internet when Geocities was taken down. We have preserved it here for historical purposes.


Copyright 2008 by Steve Rajtar

(From Interstate 4, drive east on SR 434, north on Grant St., and east on Rosedale Ave. to Candyland Park. Walk west on Rosedale Ave. to the intersection with Grant St.)(0.3 miles so far)

Northeast corner of Grant St. and Rosedale Ave.

1….Longwood Cemetery

The older headstones here date to the 19th century. Many people important in the development of Longwood, such as the Entzminger and Clouser families, are buried here.

(Walk south on Grant St. to the intersection with Church Ave.)(0.8)

Intersection of Grant St. and Church Ave.

2….Site of First Baptist Church

In about 1885, Edward W. Henck donated land for the construction of a church near the corner of W. Warren Ave. and East Lake St. When completed by 1886, it was known as the Warren Street Methodist Church. By 1891, it had been vacated by the Methodists and became the Longwood Baptist Church.

After the congregation moved to this site in 1958, the old building was used as a Boy Scout headquarters for a while, and was blown down by a hurricane in the mid-1960s. This property was sold for $350,000, and the church moved into a new building at 891 E. SR 434 in 1980.

Henck also donated land near the railroad for the Corinth Missionary Baptist Church, founded in 1883. The building was torn down and replaced by a new one dedicated in 1965, and renamed Mt. Olive Missionary Baptist Church. Mt. Olive later moved to another site at 480 W. SR 434.

(Walk west on Church Ave., south on Oleander St. and west on Pine Ave. to the intersection with Myrtle St. and look to the north.)(1.4)

East side of Myrtle St., between Bay and Warren Aves.

3….Site of P.A. Demens Lumber Mill and Factory

The 1884-85 State Gazetteer and Business Directory stated that Longwood’s chief industry was a sash, door and blind factory. This was P.A. Demens & Co., owned and operated by Peter Demens.

Demens obtained the contract to build railroad station houses for the South Florida Railroad from Lakeland to Dade City. He also supplied labor and materials for some of the buildings at Rollins College in Winter Park.

Another Demens contract was for railroad ties for the Orange Belt Railway, chartered in April of 1885. It was to run from Lake Monroe to the south side of Lake Apopka, but the organizers were unable to pay Demens the $9,400 for the rails and instead conveyed the railroad to him. Demens then took the rails he had used on a narrow gauge line he had along W. Bay Ave. and completed the line to Oakland in November of 1886. The line reached the Tampa Bay area in June of 1888, and the community there was named St. Petersburg in honor of his hometown.

(Walk west on Pine Ave., south on CR 427, west on SR 434, and north on Wilma St. to the intersection with Pine Ave.)(1.7)

Southwest corner of Pine Ave. and Wilma St. (402 Wilma St.)

4….Waits House

This home was built in about 1910 by J.M. Waits. Extensive modifications mask the original house plan, but it is presumed that the low pitched hipped roof covered a square house, with an open porch on at least two sides, plus a separate open garage.

(Cross Pine Ave. to the northwest corner.)(1.7)

Northwest corner of Pine Ave. and Wilma St. (390 Wilma St.)

5….Old Longwood School

This building was constructed in about 1883, and served until 1924 as the community school. In that year, it was converted into the Longwood City Hall and Central Fire Department. When the present City Hall was built in 1964, this building went into private ownership.

It was remodeled for use as a restaurant in the mid-1970s, but was extensively damaged by a fire in 1979. In 1984, it was modified for use as offices.

(Walk north on Wilma St. to the intersection with Bay Ave.)(1.8)

Southwest corner of Bay Ave. and Wilma St. (204 W. Bay Ave.)

6….Menick House

This home was built in about 1920 in the Bungalow style for mayor J. Henry Menick. Stucco, which first came into common usage in the 1920s, covers the exterior. Later modifications include an addition on the left and the enclosure of the porch.

(Walk west 170 feet on Bay Ave.)(1.8)

South side of Bay Ave., between Wilma and Milwee Sts. (212 W. Bay Ave.)

7….Site of Arnett House

A house was built here in about 1920, a modest Frame Vernacular structure with Bungalow details, such as tapered wood columns resting on brick piers, exposed roof rafters, and a prominent exterior chimney. Some of the lumber used in the construction of this house was taken from another house previously at this site.

In the 1920s and 1930s, it was occupied by Longwood school teacher Lossie Arnett Cramer and her daughter, Hettie. It was torn down in 2002.

(Look north across Bay Ave.)(1.8)

North side of Bay Ave., between Wilma and Milwee Sts. (211 W. Bay Ave.)


This began as a garage apartment in about 1925, and follows that period’s Frame Vernacular style. The Depression-era need for new housing resulted in many utility buildings, such as this one, being converted to residences. The lack of exterior adornment is typical of 1930s construction.

(Continue west 150 feet on Bay Ave.)(1.8)

South side of Bay Ave., between Wilma and Milwee Sts. (242 W. Bay Ave.)


This house was built in about 1920, and about all that remains from then are the rectangular plan, central chimney, and hipped roof covering the house and front porch. Stucco now covers much of the wood siding, the front porch has been enclosed, and the windows have been replaced.

(Look north across Bay Ave.)(1.8)

North side of Bay Ave., between Wilma and Milwee Sts. (241 W. Bay Ave.)


This house has several typical Bungalow style features, including stucco over the wood frame, gable roofs with wide overhangs, tapered wood porch columns on brick masonry piers, and three-over-one double hung windows. It was built in about 1920, and the porch has since been enclosed.

(Walk west on Bay Ave., north on Milwee St., and east 200 feet on Warren Ave.)(2.0)

South side of Warren Ave., between Wilma and Milwee Sts. (272 W. Warren Ave.)

11….Baptist Church Parsonage

In 1911, John Bistline came to Longwood from Pennsylvania to work in Fred Niemeyer’s store. He later went to work for W.R. Healey, who owned a number of area squab farms. Healey is credited with originating the idea of sending fresh iced squab from Longwood to northern markets by train.

In 1914, Bistline married Niemeyer’s daughter, and the couple moved into this house. Shortly thereafter, they began breeding and selling Silver Wyandotte hens, and continued this into the 1950s. The hens won awards at national competitions, and Mr. Niemeyer became a recognized authority on raising hens for show. He also was a member of the Longwood City Council for 20 years in the 1920s to the 1940s.

The house is thought to have been built in West Longwood and moved to this site by 1911, to be the parsonage for the Baptist Church which was then located next door. The L-shaped portion with the higher pitched roof is the original portion.

(Cross Warren Ave.)(2.0)

North side of Warren Ave., between Wilma and Milwee Sts. (251 W. Warren Ave.)

12….Loder House

This house was built in the mid-1920s for Howard Loder, then the secretary of the Longwood Chamber of Commerce.

(Continue east 30 feet on Warren Ave.)(2.0)

North side of Warren Ave., between Wilma and Milwee Sts. (241 W. Warren Ave.)

13….R.S. Entzminger House

This house was built in about 1925, probably by Robert S. Entzminger, a cousin of Charles. Robert was a prominent community leader in the 1920s.

This is an example of a two-story Bungalow, with typical exposed rafters supported by brackets at the roof overhang. “Bungalow” is derived from a Bengali word meaning a low house with porches, used as a wayside shelter for nineteenth century British travelers in India. Between 1910 and 1930, the bungalow was one of the most popular home designs in Florida.

A bungalow is generally one to one-and-a-half stories with a shallow pitch roof, with at least two rooms along the front of the house. The masonry piers holding up the porch floor often continue above it, topped by short wood columns supporting the roof. The front door is often off-center, and the window pattern is usually asymmetrical.

(Continue east 170 feet on Warren Ave.)(2.0)

North side of Warren Ave., between Wilma and Milwee Sts. (211 W. Warren Ave.)

14….Clouser House

During the mid-1880s, after building the small cottage at 218 W. Church Ave., Josiah B. Clouser built this larger house for his family. Clouser served as mayor of Longwood for a year at a time during three different decades, and for about 15 years ran a general merchandise store.

The home is built with a Frame Vernacular style with Chinese Chippendale style handrail and spindle work on the porch. The building has since been renovated, was used for a time as an antique store, and for a time housed a birthing center.

(Walk east 50 feet on Warren Ave.)(2.0)

South side of Warren Ave., between Wilma and Milwee Sts. (216 W. Warren Ave.)

15….Dunbar’s Garage

This is believed to have begun as the garage of John Dunbar and his daughter, Elsie, who lived next door in the 1920s and 1930s. It was later converted for use as a residence, and modified by a series of additions and alterations.

(Continue east on Warren Ave. to the intersection with Wilma St.)(2.1)

Northwest corner of Warren Ave. and Wilma St. (194 Wilma St.)

16….Site of Longwood Community Center

The Center located here until 2002 was developed in the 1930s as a recreation center. Intitially, it was an open-sided roofed structure and shuffleboard courts. It was enclosed in the 1960s, and was managed by the Longwood Park and Recreation Department.

The Center was the home of community picnics, Christmas parties, and church suppers. In its later years it was known as the Ed Myers Recreation Building.

(Cross Warren Ave. to the southwest corner.)(2.1)

Southwest corner of W. Warren Ave. and Wilma St. (202 Wilma St.)

17….Longwood Community Building

About 1886, brothers J.D. and N.J. Lewis had a small house built for them here. They left the area within a few years, and little is known about them beyond their being attorneys. The house was occupied in the 1920s and 1930s by John and Elsie Dunbar.

On this site in 2002 was erected the Longwood Community Building.

(Walk south on Wilma St. to the intersection with Bay Ave.)(2.1)

Northwest corner of Bay Ave. and Wilma St. (274 Wilma St.)

18….Site of Clouser Cabinet Shop

A small workshop was built at this corner in the late 1880s by Josiah B. Clouser, facing south toward W. Bay Ave. In the mid-1930s, it was turned to face Wilma St. and additions were made to the front and rear.

(Cross Wilma St. to the northeast corner and walk east 350 feet on Bay Ave.)(2.2)

North side of W. Bay Ave., between Wilma St. and CR 427 (133 W. Bay Ave.)

19….LeRue House

Cabinetmaker, staircase builder and blacksmith J.S. LeRue built this home in about 1885. He left the area within a few years.

His individual craftsmanship is shown in the decorative bargeboard on the gable roof edge, the elaborate porch handrail, and multi-patterned shingles. It was divided into apartments and used as a boarding house for several years. Major restoration was undertaken in the 1970s by Grace and Robert Bradford.

The only significant changes from the original house are a new rear wing addition and the replacement of the original roofing with asphalt shingles.

(Continue east 75 feet and look south across Bay Ave.)(2.2)

South side of Bay Ave., between Wilma St. and CR 427 (114 W. Bay Ave.)


This house was built in the mid-1920s during the Boom Period (1920-27). During the period of phenomenal growth, land sales skyrocketed and thousands moved to Florida seeking their fortunes. The rectangular plan with a front-facing gable roof is typical of this period’s modest residence, generally built as worker housing.

(Look across Bay Ave. to the north.)(2.2)

North side of Bay Ave., between Wilma St. and CR 427 (117 W. Bay Ave.)

21….Slade House

Shortly after he came to Longwood in about 1920, Frederick Slade bought this home, which had been built in about 1885. The original portion of the house is the higher steep-pitched roof section with the metal roofing. The original front door was in the main two-story south wall, directly behind the addition where the entry is now. This was the home of historic preservationist Grace Bradford before her death in 1990.

(Walk west on Bay Ave. and north on Wilma St. to the intersection with Warren Ave.)(2.4)

Southeast corner of Warren Ave. and Wilma St. (192 W. Warren Ave.)

22….Niemeyer House

Fred J. Niemeyer came to Longwood from Pennsylvania in 1885, at the age of 21. Four years later, he married a daughter of Josiah B. Clouser. Also in 1889, Niemeyer and Clouser built this house, called “Keystone”, and the Niemeyers lived in it for many years.

Fred Niemeyer served as a member of Longwood’s City Council, worked in Clouser’s store (which, by the early 1900s, he owned himself), and in 1905 began a 19-year period as postmaster.

At their home, the Niemeyers raised Golden and White Wyandotte hens for sale and as show birds. In the mid-1920s, Longwood was nationally known as the poultry center of Florida.

This was originally a one-story house, with the Victorian style second story and porch added in 1905. That style had generally fallen out of public favor by 1900.

(Walk east 250 feet on Warren Ave.)(2.4)

North side of Warren Ave., between Wilma St. and CR 427 (175 W. Warren Ave.)

23….City Hall

Longwood became a town and the first election was held on December 3, 1883. The first elected mayor was Edward W. Henck, who was also a justice of the peace.

The early city hall on Wilma St. was outgrown by the 1960s, so in 1963 a new one was constructed at this location. The additional space for municipal services just to the east was acquired in 1965.

(Walk east 25 feet on Warren Ave.)(2.4)

South side of Warren Ave., between Wilma St. and CR 427 (172 W. Warren Ave.)

24….Beesley-Milwee House

This house was built in about 1885, and in 1887 contained Kate Beesley’s millinery shop. It was bought in 1916 by George and Hallie LaVigne.

West Warren Ave. was primarily a commercial area until the 1920s.

(Continue east 75 feet on Warren Ave.)(2.5)

South side of Warren Ave., between Wilma St. and CR 427 (152 W. Warren Ave.)

25….Tunis Lewis House

In about 1914, this home was built by carpenter Daniel Clouser for Tunis Lewis and his mother, relatives of the Entzmingers. Mr. Lewis was a notary and a local telephone operator. This is a Frame Vernacular structure, with simple hipped roof, and a front porch with Bungalow style details.

About 1960, traffic on W. Warren Ave. was significantly reduced by the construction of CR 434 west of East Lake Ave. Prior to that time, east-west traffic through Longwood would use Warren.

(Continue east 100 feet on Warren Ave.)(2.5)

South side of Warren Ave., between Wilma St. and CR 427 (130 W. Warren Ave.)

26….Bradlee-MacIntyre House

This home was built as a luxurious winter cottage in about 1885 in Altamonte Springs. It was moved to Longwood in 1973 by the Central Florida Society for Historic Preservation in 1973 to protect it from demolition, and placed on land donated to the Society by Grace Bradford for that purpose.

The house was designed by Boston architect Nathaniel Bradlee. It is a 15-room elaborate example of the Queen Anne style, with an asymmetrical tower placement, steep pitched roofs, decorative shingle patterns, and elaborate porch detailing. It was bought by S. Maxwell McIntyre in 1904, and the McIntyre family occupied it until 1946.

The house is open for public tours.

(Continue east on Warren Ave. to the intersection with CR 427, and look east across the road.)(2.5)

South side of Warren Ave., east of the railroad tracks

27….Site of first Longwood Hotel

In 1883, Edward W. Henck built a modest hotel here, and named it the Longwood Hotel. It was operated by Henry Hand, a wheelwright who was one of the town’s first aldermen. The hotel burned down in the 1890s.

(Walk north 100 feet on CR 427.)(2.5)

West side of CR 427, between Warren and Church Aves. (300 N. CR 427)

28….Second Longwood Hotel

Construction of this large Frame Vernacular style hotel was begun by Josiah B. Clouser in 1883, about the time Edward W. Henck completed his first hotel on E. Warren Ave. When it was partially complete in 1885, Orlando realtor John Sinclair listed it for sale at a “large sacrifice”, and represented that it could be completed within 30 days.

It was purchased by Carlos Cushing, who had construction completed in 1886. Cushing named it “The Waltham”, after a district in Boston. Henck’s first Longwoood Hotel was still in operation at this time. Cushing lived on the south side of Lake Brantley in what is now Altamonte Springs, and his wife was responsible for construction of the Lake Brantley Union Chapel.

The hotel entertained numerous winter visitors, who enjoyed the excellent hunting and fishing along the Wekiwa River. It closed shortly after the devastating freezes on December 26, 1894, and February 7, 1895, which wiped out groves and resulted in many area residents moving away. The hotel reopened as the Longwood Hotel in 1910, after it was purchased by Charles W. Entzminger, who refurbished it and added gaslights in the lobby.

George Clark bought the hotel in 1922 and renamed it the St. George. After his death in 1923, his brother Fred Clark named it the Orange and Black. In 1926, the hotel was bought by a group including Joe Tinker, the hall of fame baseball player then living in Orlando. In the 1930s, it was one of Central Florida’s finest gambling establishments. In the 1950s, baseball umpire George Barr ran an umpire school there.

Louis T. Hunt married Bobbi Jo Allen, the daughter of the owners of the grocery store, with the ceremony held in the hotel. In 1957, the Hunts acquired the hotel. In 1966, it was the setting for the movie “Johnny Tiger”, starring Robert Taylor and Chad Everett. It was also the setting for the movie “The Cry of the Laughing Owl”.

Cornell University owned it in the late 1970s, and used it for a hotel operation school. The hotel, also known as the Longwood Village Inn, was renovated for use as offices in the mid-1980s.

(Walk north on CR 427 and west on Church Ave. 200 feet west of Wilma St.)(2.7)

South side of Church Ave., between Wilma and Milwee Sts. (218 W. Church Ave.)

29….Clouser Cottage

Josiah Clouser brought his wife and two children here from Pennsylvania in November of 1881. He hoped the move would be beneficial for his wife’s health, and he intended to be a master carpenter for Edward W. Henck, who had placed a newpaper advertisement in northern newspapers. It is likely that Clouser also worked for Peter Demens in the mid-1880s, and later worked on his own as a stairbuilder and cabinet maker. He, along with his son and another associate, ran Longwood’s first store.

The house provided for him turned out to be infested with fleas, and they vacated it after just one night. He found it an unsuitable place to live, so he bought back-to-back lots running from W. Warren Ave. to W. Church Ave. On the Church Ave. lot, he quickly built this small cottage, later enlarged in the 1920s, with salvaged lumber.

Its initial location was slightly east of its present site. This is a good example of a simple pioneer home, made of vertical board and batten nailed directly to the interior paneling, because there is no stud framing. The Clousers lived here for about two years while he built a more substantial home on the Warren Ave. lot.

The building was later used as an animal shed, storage space and a rental home. In the mid-1980s, Clouser’s great grandchildren purchased it and renovated it for use as a gift shop. To allow construction of the parking lot, they moved the house a little to the west, to its present site.

(Walk west on Church Ave., north on Milwee St., and northwest on Church Ave. 500 feet past the intersection with Tiburon Cove Rd.)(3.4)

North side of Church Ave., west of Tiburon Cove Rd. (593 W. Church Ave.)

30….Searcy House

John Neill Searcy travelled to Mellonville aboard the steamer “Starlight”, arriving on March 23, 1873. He was originally from Tennessee and spent four years in the Confederate army during the Civil War. At the age of 31, he started to walk to Maitland but stopped in the Longwood area and decided to homestead here.

Searcy’s initial home was northeast of today’s central Longwood, in the area of the modern Skylark Subdivision. He supported himself by selling cypress which grew on his homestead, and planted groves. He also served with the South Florida Railroad surveying party in 1879, and assisted as a carpenter.

He married in 1885 and built a two-story house in 1888. It still is used as a home at this location. Directories from 1886-87 and 1891 list him as the owner of 10 and 8 acres of groves, respectively. In 1889, he became the postmaster for Longwood.

The home is now called “Magnolia Acres”.

(Walk southeast on Church Ave., south on Milwee St., and east on Church Ave. to the intersection with Wilma St.)(4.1)

North side of Church Ave., across from Wilma St. (151 W. Church Ave.)

31….Christ Episcopal Church

The first Episcopal mission in Longwood was established in 1877. This church began as a separate entity in 1879. One of the organizers was Frederic H. Rand, who had come from Boston in 1876 and who had served in the Union army during the Civil War. The organization of the church took place in his home on the west side near Lake Searcy.

Land as a site for the church building was donated by Edward W. Henck. Frederic Rand’s parents contributed the stained glass window over the altar and raised money for the construction, which was performed by Rand, John and James Searcy, and others.

The present church was built in 1880 a little to the east of its present site, and was dedicated on Easter Sunday, April 19, 1882. It is the oldest Seminole County church in continuous use. The simple square bell tower, symmetrical plan, board and batten siding, and lack of significant ornamentation mark this as a typical early pioneer structure.

The sanctuary was enlarged in 1964, and in 1965 Searcy Hall was built for classrooms and offices. In 1988, the original church was moved westward to its present location to make room for other church buildings.

(Walk 250 feet east on Church Ave.)(4.1)

North side of Church Ave., between Wilma St. and CR 427 (141 W. Church Ave.)

32….Inside-Outside House

This building was moved here from Boston Ave. in Altamonte Springs in 1973, but that was not its first home. It was built in Boston in about 1870 as one of this country’s oldest prefabricated structures, permitting its later relocation. It is called “Inside-Outside” because the vertical framing structure is placed on the outside of the exterior horizontal siding, forming panels which are bolted together in shiplap fashion. Inside, the walls are covered with stucco over tongue and groove siding.

In 1873, its builder, Capt. W. Pierce, retired as a sea captain and moved himself and his house to Florida. It was transported by steamship from Boston to Mellonville, where it was transferred to mules for the ride to Altamonte Springs. After it was reassembled, the ground floor served as a cabinet shop, while the family lived upstairs. This is one of the most architecturally unusual buildings in the area.

To protect the home from demolition, it was moved here by the Central Florida Society for Historic Preservation.

(Continue 100 feet east on Church Ave.)(4.2)

North side of Church Ave., between Wilma St. and CR 427 (135 W. Church Ave.)

33….Woman’s Club

In early Longwood Prof. Lynch, a traveling instructor, taught school on a periodic basis, most likely teaching classes in a small building on the grounds of the present Christ Episcopal Church (151 W. Church Ave.). The building was also the settlement’s community meeting place, and is probably the oldest building in Longwood.

When Christ Church was built in 1880, the building was moved westward near the intersection of W. Church Ave. and Rangeline Rd., and was used as a chapel. As the West Longwood Chapel, it was the home of The West Longwood Pioneers and The Self Union.

In about 1914, the building was moved by Daniel Clouser, the younger brother of Josiah B. Clouser, to 150 W. Church Ave. for use as the Longwood Civic League Woman’s Club, which had been founded in 1911 to do projects in the community that the city government could not afford to do. It was expanded with the addition of a large meeting room with a stage. The original portion is behind the two side additions (added in about 1914) and the center porch addition, originally open but enclosed in the 1950s.

(Continue 150 feet east on Church Ave.)(4.2)

Northwest corner of Church Ave. and CR 427 (101 W. Church Ave.)

34….Site of Allen Store

A large two-story building was constructed in 1908 by Mr. and Mrs. J.H. Allen. The first floor was a grocery store, and the second was a residence. The building was demolished in the 1950s.

A new building was erected in 1968 for the post office. It was torn down in 2002.

(Continue east on Church Ave. to the intersection with CR 427, and cross Church Ave. to the southwest corner.)(4.2)

Southwest corner of Church Ave. and CR 427 (322 N. CR 427)

35….Site of Dixie Food Mart

A commercial building was erected here in the early 1960s. It is surprising that such a well-located parcel of property had nothing built on it prior to that. In late 2002, it once again became a vacant lot.

(Cross CR 427 to the southeast corner.)(4.3)

Southeast corner of Church Ave. and CR 427 (323 N. CR 427)

36….Site of Henck-Tinker Building

Joe Tinker, Edward W. Henck and others developed a commercial building on this corner in about 1925. The Longwood State Bank, the first bank opened in Longwood, occupied the portion at 101 S. East Lake, with J.E. Walker as founder and president. It went out of business in 1932. Other tenants were the MacReynolds Drug Store, Jackson’s Grocery, and a barber shop.

In about 2004, the building was removed and the corner was landscaped as a park.

East Lake Ave., also known as CR 427, was once part of the Dixie Highway. This was the dream of Carl Fisher of Indianapolis, who had made his fortune in the new auto industry shortly after the turn of the century. Fisher wanted to build a highway from Chicago to Miami, and when the news got out, many communities formed associations to lobby for inclusion on the route.

The Dixie Highway Association met in Chattanooga and chose a route passing through Tallahassee and Jacksonville, and proceeding south along the east coast. Frenzied lobbying also produced an inland route passing through Gainesville, Ocala, Longwood, Winter Park, Orlando, Kissimmee, Bartow and Arcadia, rejoining the coastal route at Palm Beach.

In 1915, Fisher led an auto cavalcade from the Midwest to Miami, popularizing auto trips to Florida. The Dixie Highway was officially open for traffic in October of 1925 from the Canadian border at the northern tip of Michigan to Miami.

(Cross Church Ave. to the northeast corner, then walk east 150 feet.)(4.3)

North side of Church Ave. between CR 427 and the railroad tracks (133 E. Church Ave.)

37….Site of Slade-Menick Company

Frederick Slade and Henry Menick established a business here in about 1920 to manufacture wooden handles for axes and other tools.

(Walk west 25 feet on Church Ave. and look south across the road.)(4.3)

South side of Church Ave., between CR 427 and the railroad tracks

38….Site of Railroad Depot

The Lake Monroe and Orlando Railroad, which was chartered in 1875, was renamed the South Florida Railroad in 1879. That same year, a new charter was issued to extend the tracks to Charlotte Harbor on the Gulf of Mexico. Involved in the venture were Edward W. Henck of Longwood, Dr. C.C. Haskell of Maitland, A. Muser of Longwood, Dr. E.T. Crafts who arrived in Longwood in 1876, and Chief Engineer F.C. Tucker. Money for construction was raised by the owners of the Boston Daily Herald.

The groundbreaking ceremony took place in Sanford on January 10, 1880, and the narrow gauge line reached Longwood by June 1. The railroad depot was erected here, and not vacated by the railroad until the 1960s. It was then moved to Hilliard, Florida, and modified for use as a home. The train took an hour to go from Orlando to Longwood, with a stop in Maitland.

The South Florida Railroad was only one of three that passed through Longwood in the 1880s. The others were Peter Demens’ Orange Belt Railroad, which went from Longwood to Apopka, Oakland and St. Petersburg, and John H. Dave’s Florida Midland Railroad, which went to Apopka, Ocoee and Kissimmee.

(Continue west 40 feet on Church Ave.)(4.3)

North side of Church Ave., between CR 427 and the railroad tracks (117 E. Church Ave.)

39….Former Post Office

The Longwood Post Office was officially established on May 19, 1876, and Edward W. Henck was named the first postmaster. He held that office until 1885.

This building was constructed in about 1915. A few years later, it was purchased by Lester Payne, who had another built next door. His wife, Blanche, served as postmaster from 1932 to 1958, with the post office being located here until 1946, when it was moved to 107 E. Church Ave.

(Continue west 20 feet on Church Ave.)(4.3)

North side of Church Ave., between CR 427 and the railroad tracks (107 E. Church Ave.)

40….Payne Building

Lester Payne, who had bought the building next door, built this one with S.R. Long, a local carpenter, out of rusticated concrete blocks in 1920. He had a hardware store on the first floor, and a residence on the second. The front is emphasized by the stepped parapet wall and a cantilevered sleeping porch was located over the sidewalk until 1998. This is an example of early Boom Period Masonry Vernacular construction.

(Cross CR 427 and walk north on CR 427 and west 175 feet on Jessup Ave.)(4.4)

South side of Jessup Ave., west of CR 427 (138 W. Jessup Ave.)

41….Tucker House

This Bungalow was built in about 1920 for L.R. Tucker. Representative architectural elements include the one-story wings spreading from the central area, three-over-one double hung sash windows, and oversized exposed framing. The garage is original.

(Walk east on Jessup Ave., north on SR 427, west 20 feet on Florida Ave., north on the sidewalk crossing the grassy area, and north on Freeman St. to the intersection with Magnolia Ave.)(4.5)

Southwest corner of Magnolia Ave. and Freeman St. (288 Freeman St.)

42….Entzminger’s Daughter’s House

Charles Entzminger had this home built in 1926 for his daughter, who had recently been married. Its low pitched roof, tapered wood columns on masonry piers, and exposed rafters and beams are typical of the Bungalow style.

Entzminger, a member of the Florida legislature, bought and reopened the Longwood Hotel in 1910. He also was one of the incorporators of the Overstreet Turpentine Company, which by 1905 operated southwest of downtown Longwood. In 1923, its name was changed to The Overstreet Investment Company.

When Seminole County was formed in 1913 from Orange County, Entzminger was one of the first trustees appointed for the Longwood District of the Seminole County School Board. He later served as a county commissioner.

(Cross Magnolia Ave. to the northwest corner.)(4.5)

Northwest corner of Magnolia Ave. and Freeman St. (346 Freeman St.)

43….Fitch House

This house was built in about 1888 for J.C. Fitch. At the time, he was a city alderman, but did not remain in the area for long. The home was purchased in about 1893 by G.W. Hardaway, a minister at the Longwood Congregational Church, then located at the north end of East Lake St. Charles W. Entzminger later purchased it in 1920.

The two-story portion, with the decorative shingled gable end wall and central chimney are original, but alterations and additions obscure much of the original form of the house.

(Walk west 175 feet on Magnolia Ave.)(4.6)

South side of Magnolia Ave., west of Freeman St. (110 W. Magnolia Ave.)

44….Entzminger Garage Apartment

This was built by Charles W. Entzminger, originally as a garage apartment, in 1926. The two-story portion and perhaps the sleeping porch are original. The front and side porch were likely added when the garage was converted to living space.

(Walk east on Magnolia Ave. and north on Freeman St. to the intersection with Palmetto Ave.)(4.6)

Southwest corner of Palmetto Ave. and Freeman St. (398 Freeman St.)

45….Henck House (“Founder’s Square”)

This home was built in 1875 by Josiah B. Clouser for Edward W. Henck, who owned it until his death in 1930. From shortly after the “Great Freezes” in 1894 and 1895 until 1914, during which time Henck lived and worked in Plainfield, New Jersey, as a stockbroker and investment advisor, the home was maintained by Clouser and others. After his return, Henck was involved in real estate sales, and in the 1920s sold home lots priced from $100 to $500 at $10 to $50 down, with the balance payable at $5 to $20 per month.

The house plan began as a simple rectangle surrounded by a porch wrapping the front and sides. One-story wings were later added on the sides.

For several years during the 1920s, Bobbi Jo (Allen) Hunt assisted the Hencks while Mrs. Henck was very ill. After Mrs. Henck’s death, she assisted Mr. Henck and inherited his entire estate. Subsequently, the Hunts lived in the Henck house for many years.

(Cross Palmetto Ave. and walk east 75 feet.)(4.7)

North side of Palmetto Ave., between Freeman St. and CR 427 (101 E. Palmetto)

46….McGaughey House

J.W. McGaughey, owner of the Eva Lumber Company which produced cypress roof shingles, employed Daniel Clouser to build this home for him in 1914. It was purchased by bank president and mayor J.E. Walker in 1920, and upon his death in 1930, it was bought by C.C. Jacobson.

Until the late 1960s, Freeman St. was a part of East Lake Ave. and CR 427, which came north along East Lake Ave. and turned abruptly east along Palmetto Ave. When CR 427 was realigned, this section was renamed Freeman St. in recognition of the Freeman family which had lived in this house since the 1930s.

(Walk east on Palmetto Ave. and northeast on the west side of CR 427 900 feet until you see the lake on your left.)(4.9)

East Lake

47….Site of Demens’ House

Peter Demens (formerly Pyotr Alexayevich Dementyev) came to Longwood in 1881 at the age of 31 from St. Petersburg, Russia. Shortly after arrival here, he bought an 80-acre grove and a one-third interest in a sawmill (Demens, McCain & Cotter). In 1883, he bought out his sawmill partners and expanded his business. He and his family initially lived in a two-room shack in a piney clearing on the north side of this lake.

In early 1889, to cover large debts, Demens sold his railroad to his primary creditors and he moved to Asheville, North Carolina. With much of the timber cut for Demens’ enterprises, an extensive turpentine industry arose. D.K. Horne opened the area’s first large turpentine still.

Edward W. Henck of Boston, who served in the Union army during the Civil War, arrived in Florida in 1873. After traveling on foot, he located a homestead on the south shore of East Lake, then known as Myrtle Lake. Henck named the area “Longwood” after the Boston suburb which he, as an engineer, had helped to lay out. Henck’s homestead cost him $1.25/acre.

In addition to being Longwood’s first postmaster, Henck was also involved in obtaining a charter for the railroad in Central Florida. Henck was elected as Longwood’s first mayor, was a justice of the peace, operated a real estate office, and is listed in some early directories as an attorney.

(Continue northeast on CR 427, then walk east on Georgia Ave. and north on Oak St. to the point of beginning.)(6.2)


A Sightseeing Tour of Seminole County Historic Sites, (Seminole County Historical Commission 1991)

Early Days of Seminole County, Florida, by Arthur E. Franke, Jr. (Seminole County Historical Commission 1988)

Flashbacks: The Story of Central Florida’s Past, by Jim Robison and Mark Andrews (The Orlando Sentinel 1995)

Florida: A Pictorial History, by Hampton Dunn (The Donning Company 1988)

Florida Historic Homes, by Laura Stewart & Susanne Hupp (Sentinel Communications Company 1988)

Full Steam Ahead!, by Albert Parry, Ph.D. (Great Outdoors Publishing Company 1987)

Guide to Florida’s Historic Architecture, (University of Florida Press 1989)

History of the First South Florida Missionary Baptist Association, by Altermese Smith Bentley (The Mickler House 1988)

Longwood Historic District Study Project Report, by Yeilding & Provost (1989)

Longwood Historic District Walking Tour, (Longwood City Commission 1991)

Orlando: The City Beautiful, by Jerrell H. Shofner (Continental Heritage Press 1984)

Our Heritage: 1891-1981, by A. Wayne Joiner (First Baptist Church of Longwood, Florida 1981)

The Pioneer Churches of Florida, by Elizabeth Chase (The Mickler House 1976)

“Wish You Were Here”, by Hampton Dunn (Byron Kennedy and Company 1981)

Click here for a copy of the trail rules.

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