Green’s Dictionary of Slang

Sugar Hill n.

[note Lincoln U. (Oxford, Penn.) use c.1934: ‘Sugar Hill. The newest dormitory, where rentals and appointments are relatively high]
(US black)

1. that area of Harlem otherwise known as Coogan’s Bluff, between Amsterdam and Edgecombe Avenues, between 138th and 155th Streets. As well as the rich, many black intellectuals and artists chose to live in the area, known for its grand apartment houses, once the original white population had moved out during the 1920s; thus Sugar Hiller, a resident of this area, thus attrib [sugar n.1 (1)].

News-Palladium (Benton Harbor, MI) 26 Oct. 11/3: Wnereas Strivers row was for years the one swankiest spot, [...] the Sugar Hill section has created a new fashionable zone.
[US]N.Y. Age 16 Aug. 6/5: ‘I am glad to see all the progress being made in Harlem [...] Sugar Hill is just too bad’.
[US]Lil Hardin Armstrong ‘Harlem on Saturday Night’ [lyrics] Now, all the Sugar Hillers are a bunch of killer-dillers.
[US]Pittsburgh Courier (PA) 26 Feb. 11/1: Who is this guy ‘Daddy Warbucks’ that’s causing all the ‘Sugar Hill’ ladies to miss meals.
[US]D. Burley Orig. Hbk of Harlem Jive 114: He would own a big house on what is known as Sugar Hill.
[US]L. Durst Jives of Dr. Hepcat (1989) 5: Jackson, you may puff on down cross states, hit the high spots from Chi to sugar hill, do a statue act on 18th and Vine or tamp the stroll on Lenox Avenue. Wherever your anchor you just ain’t nowhere until you get a house party invite.
[US](con. 1940s) Malcolm X Autobiog. (1968) 175: The Four Horsemen that worked Sugar Hill [...] there was a tough quartet.
[US](con. 1925–9) Ottley & Weatherby Negro in N.Y. 240: The steady increase in Harlem’s population led to an overflowing of this class into the Washington Heights section, known to negroes as ‘Sugar Hill’.
[US]‘Touré’ Portable Promised Land (ms.) 154: We Words (My Favorite Things) [...] Crooklyn. La-La. Illadelphia. Sugar Hill. Brick City.

2. the brothel and ‘red-light’ area of the black part of any southern town [sugar n.4 (1)].

[US]Trimble 5000 Adult Sex Words and Phrases.
[US]Maledicta IX 148: There are black terms sugar hill and jazz joint [...] (most now obsolescent or obsolete).