HISTORY
The Annex was subdivided in the 1870's and 1880's. It immediately became one of Toronto's elite neighbourhoods.

The Annex's Golden Era lasted until the 1920's, when the upper classes began to migrate northward to newer more fashionable suburbs in Forest Hill and Lawrence Park.

 

Those who stayed behind helped form the Annex Residents Association. This powerful lobby group saved the Annex from the proposed Spadina Expressway which would have divided the Annex in half, had it been built.

 

The Annex has endured and is now over one hundred years old. It remains one of Toronto's premier neighbourhoods.

 

OVERVIEW
The Annex is Toronto's most heterogenous community. Its residents include successful business people, prominent artists, University of Toronto students and faculty, and people from all walks of life.

 

This is a vibrant neighbourhood that draws its energy from the University of Toronto, as well as from the bars, restaurants and nightclubs that crowd together along Bloor Street.

 

Many of the rooming houses and multi-unit homes in the Annex have recently been converted back to single family houses reflecting the return to prominence of this historic Toronto neighbourhood.

 

 

HISTORY
The sightlines and majestic beauty of the Avenue Road Hill have, over the years, inspired many of Toronto's wealthiest citizens to build their homes here.

 

The one home that stands out above all the others is Casa Loma, a real life medieval castle. Casa Loma was built in 1911, by Sir William Henry Mill Pellatt, a prominent financier, industrialist, and military man.

 

It took three hundred men nearly three years to build Casa Loma, at a cost of $3,500,000, which at that time was an unprecedented amount of money to pay for a home. Sir Henry enjoyed his dream home for less than ten years before mounting debts forced him to turn Casa Loma over to the City of Toronto.

 

In the 1920's, shortly after Sir Henry's departure from Casa Loma, the extensive grounds and greenhouses to the north of the castle were subdivided, and the current neighbourhood began.

 

OVERVIEW
The striking silhouette of Casa Loma provides a romantic backdrop to this posh Toronto neighbourhood.

 

Nestled on the brow of the Avenue Road Hill, and surrounded by ravines and parkland, this residential enclave looks and feels more like an enchanted forest filled with storybook homes, than the big city neighbourhood it really is.

 

 

HISTORY
The Christie Pits neighbourhood is named after the former Christie Sand Pits, that were a local landmark in this area until the early 1900's. Christie Street is named after William Mellis Christie, who co-founded the Christie & Brown Cookie Company, in downtown Toronto in 1861.

 

The Christie Sand Pits were rich in sand, gravel, and clay deposits - remnants of the last ice age. These deposits were excavated in the late 1800's and early 1900's, and used in the construction of many of Toronto's early roadways and public buildings.

 

By 1909, the Christie Sand Pits were depleted and the city turned the former quarry into Willowvale Park. However, the Christie Pits name has endured and is used in reference to the park and the surrounding neighbourhood to this day.

 

OVERVIEW
Christie Pits is one of Toronto's most vibrant multicultural neighbourhoods. It has historically been a transitional home for immigrants upon their arrival to Toronto. However, as Christie Pits continues to mature and prosper, more people are choosing to stay here rather than move to the suburbs. This stability bodes well for the future of the Christie Pits neighbourhood.

 

 

HISTORY
Deer Park used to be referred to by the First Nations people as "Mushquoteh", which means a meadow or opening in the wood where deer come to feed. In 1837, the Heath family purchased forty acres of land in "Mushquoteh". Appropriately, they named their estate Deer Park.

 

By the 1850's, the Deer Park area had grown to include a handful of country villas, a general store, a school, a cemetery, a race track, and a hotel that was located at the intersection of Yonge and St. Clair. Patrons at the Deer Park Hotel used to delight in feeding the deer that roamed on the hotel grounds.

 

The deer were long gone by the time Deer Park was annexed to the City of Toronto in 1908. Deer Park filled in very quickly after annexation. By the 1930's the Deer Park neighbourhood was established as one of Toronto's finest residential districts.

 

OVERVIEW
Deer Park is different from many upscale Toronto neighbourhoods in that its homes are not isolated on the periphery of the neighbourhood. The residential streets spill out onto either Yonge Street or St. Clair Avenue, right into the heart of one of Toronto's busiest shopping, entertainment, and business districts.

 

Deer Park's commercial centre provides a good balance for this neighbourhood which is surrounded by lush green parkland, majestic trees, and the Vale of Avoca Ravine.

 

 

HISTORY
Forest Hill was incorporated as a village in 1923. It was named after the summer residence of John Wickson, built in 1860, at the junction of Eglinton Avenue and Old Forest Hill Road. The hill is still there, but the forest is long since gone, having been replaced by apartment buildings.

Prior to its incorporation, Forest Hill had been known as "Spadina Heights". Spadina is a derivative of the First Nations word "Ishapadenah", which means a hill or sudden rise in land. The boundaries of the present day neighbourhood are shaped from the old Spadina Heights school district.

 

"Lower Forest Hill", south of Eglinton, was completely developed by the 1930's. "Upper Forest Hill" was slower to develop due to the fact it had previously been occupied by the old Belt Line railway, and then by industry.

 

In 1967, Forest Hill Village joined Swansea Village as one of the last two independent villages to be annexed by the City of Toronto.

 

OVERVIEW
The Forest Hill neighbourhood is one of Toronto's most prestigious districts. The mansions in Lower Forest Hill are rivalled only by those found in Rosedale. Forest Hill's schools are among the best in the country. They include two of Canada's most revered private schools: Upper Canada College for boys, and Bishop Strachan School for girls.

 

In 1909, Bracondale Village was annexed by the City of Toronto. Shortly thereafter, Frank Turner's heirs subdivided the Bracondale estate and turned it into an exclusive subdivision named " Bracondale Hill Park".

 

The Turner family retained ownership of the Bracondale house until 1937, when it was sold to the City and demolished in order to make room for Hillcrest Park.

 

OVERVIEW
Hillcrest is a mature established neighbourhood with quiet tree-lined streets and whimsical looking houses, that make you feel as if you are far away from the bright lights of the big city

The distinguishing feature of Hillcrest is its location perched on the ridge of the Davenport escarpment. The rich topography of this area has resulted in some of the prettier streets in Toronto.

 

 

HISTORY
Moore Park was subdivided in 1889 as an exclusive Toronto suburb for the very wealthy. Its namesake and creator was a gentleman by the name of John Thomas Moore.

Moore was instrumental in building the Belt Line Railway, Toronto's first commuter train. He personally oversaw the construction of the Belt Line's showpiece station at Moore Park.

 

Moore leveraged all his money on the Belt Line, predicting it would bring many buyers to his Moore Park subdivision. However, shortly after the Belt Line opened Toronto suffered through a horrible Depression and the Belt Line went bankrupt.

 

This setback postponed the building of homes in Moore Park until the early 1900's. By the 1930's, Moore Park was completely developed.

 

OVERVIEW
Moore Park is surrounded on all sides by natural barriers. To the north is the Mount Pleasant Cemetery, to the south is the Park Drive Ravine and the railway tracks, to the east is the Moore Park Ravine and to the west is the Vale of Avoca Ravine.

 

With so much nature at its doorstep, it is not surprising that Moore Park is one of Toronto's most sought after neighbourhoods.

 

 

HISTORY
Rathnelly's history revolves around the former Rathnelly house built in 1830 by Senator William McMaster. McMaster's home was named after his birth place in Rathnelly, Ireland. The McMaster estate remained intact until the 1880's, when it was sold to developers. The present day neighbourhood began shortly thereafter.

 

The Rathnelly neighbourhood made headlines in 1967, while celebrating Canada's 100th birthday. During the celebrations Rathnelly residents playfully declared themselves as an independent republic of Canada. To mark their independence, the "Republic of Rathnelly" elected a queen, organized a parade, formed an "air farce" of 1,000 helium balloons, and issued Republic of Rathnelly passports to everyone in the neighbourhood.

 

Over twenty years later the "Republic of Rathnelly" is still going strong.

 

OVERVIEW
Rathnelly is a picturesque little enclave of homes, situated at the bottom of the Avenue Road Hill. It is home to a large number of artists, academics, writers, and media people.

 

Rathnelly residents organize a one-of-a-kind street festival, held either every year or “when the mood strikes”. The highlight of the festival is a much anticipated pancake breakfast that Rathnelly residents literally flip over.

 

 

HISTORY
Regal Heights was settled in 1818, by an Irishman from Tipperary County, by the name of Bartholomew Bull. Bull was responsible for building Davenport Road, which was originally known as "Bull's Road".

 

Bulls' second house, built in 1830, was called "Springmount". This was the first brick building in York Township, and as such was considered quite a novelty in its early years. Springmount was descriptively named after a water course that once meandered down the Davenport escarpment in front of the Bulls' homestead.

 

Springmount remained in the possession of the Bull family until the estate was sold to developers in 1910. The Springmount name has been perpetuated in Springmount Avenue, which is one of the signature streets in the Regal Heights neighbourhood.

 

OVERVIEW
The Regal Heights neighbourhood is situated on the western crest of the Davenport escarpment. This neighbourhood has many distinguishing characteristics including very large turn of the century houses, winding tree- lined streets, and an elevation atop the Davenport escarpment that offers many home owners unparalleled views of the Toronto skyline.

 

 

 

HISTORY 

Rosedale began when Sherrif William Botsford Jarvis, and his wife Mary settled on a homestead here in the 1820's. It was Mary Jarvis who came up with the Rosedale name, as a tribute to the profusion of wild roses that graced the hillsides of the Jarvis estate.

 

OVERVIEW
For over one hundred years Rosedale has held the distinction of being Toronto's most fashionable address. Many of Toronto's wealthiest and most prominent citizens reside in the Rosedale neighbourhood.

Rosedale is unique in that it is surrounded by beautiful ravines and parkland that make you feel as if you are far away from the city, while in reality Rosedale is just a few minutes from Toronto's major business, entertainment, and shopping districts.

 

 

HISTORY
Seaton Village was originally settled by Colonel David Shank and Captain Samuel Smith. Both men were loyalists who served under John Graves Simcoe in the Queens Rangers. In the early 1800's, the Shank and Smith farm lots were acquired by George Crookshank.

 

The Crookshank estate began at the foot of Bathurst Street where it overlooked the lake. A laneway from the Crookshank house ran north to his country farm, where Seaton Village is today. The Crookshank laneway is now part of Bathurst Street.

 

Seaton Village is named after Lord Seaton, a former Lieutenant Governor of Canada. The Village was laid out on the old Crookshank farm in the 1850's. However, residential development of the present day neighbourhood did not commence until around 1888, when Seaton Village was annexed by the City of Toronto.

The focal point of this neighbourhood is Vermont Square. This city park is the home of the St. Alban's Boys' and Girls' Club, a community agency that offers children and families a variety of social and recreational programs.

 

 

HISTORY
The South Hill neighbourhood is defined by the Avenue Road Hill. This historic land formation was the former shoreline of ancient Lake Iroquois whose chilly waters receded into present day Lake Ontario some 12,000 years ago at the end of the last ice age.

 

The escarpment that Lake Iroquois left behind was covered by a dense forest interrupted only by the ponds, creeks, and waterfalls that graced the Avenue Road Hill up until the 1900's.

 

South Hill's natural beauty made it an instant favourite with wealthy Toronto landowners. In the mid to late 1800's, South Hill was dotted with mansions that were unsurpassed in variety and scope anywhere else in Toronto. "Oaklands", the gingerbread mansion overlooking Avenue Road, "Spadina House" at 285 Spadina Road and "Casa Loma", the 98 room dream home of Sir Henry William Pellatt, still endure from this bygone era.

 

OVERVIEW
South Hill may not have the same name recognition as a Rosedale or a Forest Hill, but it is every bit as glamorous and exclusive as these other elite Toronto neighbourhoods.

 

South Hill is centrally located near Toronto's business and entertainment districts, and is also conveniently located near many of Toronto's highly regarded public, private and Catholic schools.

 

 

HISTORY
The Summerhill neighbourhood is named after 'Summer Hill' house, a magnificent Regency cottage built in 1842, by transportation baron Charles Thompson. Summer Hill stood on the crest of the hill where the houses on Summerhill Gardens are located today.

 

Thompson's two hundred acre Summer Hill estate stretched from the present day Yonge Street to Mt. Pleasant Road. On this site Thompson established the 'Summer Hill Spring Park and Pleasure Grounds'. This amusement park featured rides, games, swimming and a popular dance pavilion that was located inside the Summer Hill house. Thompson's heirs subdivided Summer Hill in the 1860's.

 

From the 1880's onward Summerhill's development revolved around the railway. The first residents of this neighbourhood worked at the North Toronto Railway station which was established on Yonge Street near Summerhill in the 1880's. This station - rebuilt in 1916 - is distinguished by its grand clock tower and now serves as the neighbourhood liquor store.

 

In the 1920's the Canadian Pacific Railway made Summerhill their main Toronto station. When Summerhill station closed this neighbourhood went into a period of decline that lasted until the Summerhill subway station opened in 1965. Summerhill has enjoyed a position of prominence among Toronto neighbourhoods ever since.

 

Ed. Note: The former Summer Hill Coach House, circa 1865, is still standing today, at the rear of 36 Summerhill Gardens. This house with its distinctive slate roof can be seen from the south end of the Rosehill Reservoir.

OVERVIEW
Summerhill's turn of the century houses, winding tree-lined streets, and abundance of parkland have made it one of Toronto's most preferred neighbourhoods. It is conveniently located along the Yonge Street corridor, providing Summerhill residents with easy access to Toronto's downtown business and entertainment districts.