Orchard Road Presbyterian Church

Wesley Methodist Church is the oldest Methodist church in Singapore. It is the second Methodist Church to be built in Singapore after the Methodist Episcopal Church at Coleman Street which subsequently became a school hall. It is located in Fort Canning Hill.

Amber Mansions was a shopping centre and residential building located at the curve between Orchard Road and Penang Road in what is currently known as Dhoby Ghaut, Singapore. Constructed in the 1920s, the shopping centre was one of the first shopping centres in Singapore.

Fort Canning Tunnel (Chinese: 福康宁隧道; pinyin: Fúkāngníng Suìdào), abbreviated as FCT, is a vehicular tunnel in the Central Area of Singapore. Besides the utilisation of relatively new engineering techniques, special care was taken to minimise impact on the environment of the surrounding Fort Canning during construction. The original contract for the FCT project was awarded to Sato Kogyo for S$25.95 million.The FCT was one of four Technical Tours organised by the Land Transport Authority and Association of Consulting Engineers on 29 September 2006 during the World Roads Conference 2006 held in Singapore.

The YMCA Building is the current headquarters of YMCA of Singapore. It also operates a hotel under the name of YMCA @ One Orchard.

The Kempeitai East District Branch was the headquarters of the Kempeitai, the Japanese military police, during the Japanese occupation of Singapore from 1942 to 1945. It was located at the old YMCA building, at the present site of Singapore's YMCA Building on Stamford Road. Opened in 1911, the distinctive Art Deco YMCA building was the site of interrogation and torture of many innocent civilians, including the war heroine Elizabeth Choy. After the war, the Singapore government erected several memorials with some at the former massacre sites. In 1995, the former site of the old YMCA building was gazetted by the National Heritage Board as one of the eleven World War II sites of Singapore.

The Cathay is a mixed-use 17-storey cinema, shopping mall and apartment building located at Handy Road and Mount Sophia in the Museum Planning Area of Singapore.

The Cathay Building (simplified Chinese: 国泰大厦; traditional Chinese: 國泰大廈; Malay: Bangunan Cathay) was opened in 1939 by Dato Loke Wan Tho as the headquarters for the British Malaya Broadcasting Corporation. Located at 2 Handy Road in the Museum Planning Area of Singapore, the building was most known for its air-conditioned theatre known as the Cathay Cinema, then a technological marvel and the first to be built in Singapore. Cathay Building was the first skyscraper in Singapore and tallest building in Southeast Asia at that time.

Dhoby Ghaut () is a place in Singapore that often refers to the Dhoby Ghaut MRT station, a major interchange station on Singapore's Mass Rapid Transit network connecting the North-South Line, North East Line, and the Circle Line. As a place, Dhoby Ghaut lies along the eastern end of Orchard Road. There is a shopping mall above the MRT station called Plaza Singapura.

Temasek Shophouse is a building on Orchard Road in the Museum Planning Area of Singapore. Completed as a townhouse in 1928, it presently serves as a "social impact hub".

The National Museum of Singapore is a public museum dedicated to Singapore's art, culture and history. Located within the country's Civic District at the Downtown Core, it is the oldest museum in the country, with its history dating back to when it was first established in 1849, starting out as a section of a library at the Singapore Institution as the Raffles Library and Museum. After several relocations over the next few decades, the museum moved to its current permanent site at Stamford Road in 1887. Between 1993 and March 2006, it was briefly known as the Singapore History Museum, before it returned to its present name that was first given in 1965. The museum preserves and interprets Singapore's social history, exploring the key events and people that have shaped the nation. Over the centuries, the National Museum of Singapore has expanded and undergone various expansions and renovations, with the most recent being a three-and-a-half-year restoration that was completed in 2 December 2006, and was officially reopened on 7 December 2006 by former President of Singapore S. R. Nathan and the Minister for Information, Communications and the Arts Lee Boon Yang. The Singapore History Gallery opened on 8 December that same year. It is one of six national museums in the country; the other five being the two Asian Civilisations Museums at Empress Place Building and Old Tao Nan School respectively, the Singapore Art Museum, Peranakan Museum as well as the National Gallery Singapore. The National Museum of Singapore is also one of the country's national monuments, having been designated as such in 1992 by the National Heritage Board. It is one of the largest museums in Asia. Admission to the National Museum of Singapore is complimentary for Singaporean citizens and permanent residents.

School of the Arts (SOTA) is a specialised independent school in Singapore, offering a six-year integrated arts and academic curriculum leading to a International Baccalaureate diploma or career-related programme. SOTA is an agency of the Ministry of Culture, Community and Youth.

The MacDonald House is a historic building and monument in Singapore, located at Orchard Road in the Museum Planning Area, within the Central Area. It was the first building to be fully air-conditioned in Southeast Asia. Located a short distance from the Istana, it was the last remaining office building in facing brick in the central area. Initially built for a bank, it continues to function as a banking hall (albeit for a different bank) today, although it is better known as the site of a bombing attack in 1965 at the height of Indonesia–Malaysia confrontation.