"Richest Looking" Areas

[Arizona Iced Tea]

A lot of homes in Sugar Land have that mass produced upper middle class suburbia look to them.

[Mr. Illini]

If you’re looking for a lot of McMansions, outside of Houston and Dallas are probably a good bet. People in Winnetka and Scarsdale have taste.

[cg41386]

MendhaM, NJ
Colts Neck, NJ
Holmdel, NJ (a bit more mcmansiony but plenty of huge houses)

[Dr. MB]

In Oregon - Lake Oswego, Forest Heights, Bethany, Bull Mountain, some of the areas along Skyline Blvd. and in Forest Park, Happy Valley, parts of West Linn and other parts of the west hills. Alameda and Eastmoreland on the east side of Portland. Also quite a few of the rural areas in Washington and Clackamas County. Phil Knight's house is deep in the woods south of Hillsboro and he's not the only rich person to live out there. Aside from a few areas though there's nothing truly insane like you'd see in California.

Bend is also pretty wealthy, especially on the west side of town. A lot of resort communities and fancy homes outside of there too.

[Del Tachi]

If you’re looking for a lot of McMansions, outside of Houston and Dallas are probably a good bet. People in Winnetka and Scarsdale have taste.

Winnetka and Scarsdale are just older.  Rich suburbs of similar vintage in Texas (i.e., Highland Park or Broadacres) are just as classy.