Thousand Oaks area is very nice. Generally older home owners with old money. More of a ritzy clan. Simi Valley is more relaxed with a lot of families, some newer communities (Wood Ranch & Big Sky). I personally lived in the San Fernando Valley for 36 years and it took a lot for my wife to convince me to move to Simi Valley, Wood Ranch. But I have to tell you, I don't regret it at all. My concern was taking my 2 kids out of private school and putting them in the public school system in S.V. It turned out to be great. It is 98% in the teacher you get no matter what school it is or where it's located. The other 2% is the surroundings. SImi is considered one of the safest in the nation, great weather year round, a lot of family events (The Ronald Reagan Library, Pony baseball, local circus, water park, great golf courses) just to name a few. Thousand Oaks has many great things also. Civic Center, man made lake, Sherwood Country Club (Tiger Woods plays here), good schools (Oaks Christian, Westlake High). Like I said, 2 good areas, it would probably come down to what your likes and dislikes are. If you are more of the younger family (Simi Valley) or more of the ritzy (Thousand Oaks). You won't go wrong in either city.
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2 different ciites with 2 different personalities.
I am from Rockaland County New York, a neighborhood feel. You won't that in CA to much!
However Thousand Oaks is the biggest city in Ventura
County. It also has more celebrities and higher income levels ( North Ranch, Westlake, Lake Sherwood)
I lived there as a teenager fresh from New York.
Closer to beach
better school district ( they still have their problems)
Simi Valley is more blue collar , they have some newer areas Big Sky ( very nice, newest major development), Wood Ranch( very nice also ).
I personnally like the Simi Valley residents as they seem to be much friendlier and less concerned about what car you drive, alot of keeping up withteh Jones's.
I also find Simi Valley is a younger crowd ( young families, 25- 35) alot more children, Thousand Oaks recently had to shut down schools for lack of students( to expensive for young families) . Simi Valley surprised me with its warmth and friendly neighbors. I am acustomed to speaking my mind to strangers and neighbors alike.
I have lived in both towns and prefer Simi for the folowoing reasons
the freeway ,118 is much more accessible then the 101 ( thousand Oaks) to get into LA
The people are down to earth and will often say hello ( my neighbors in 1000 Oaks seem very shy and like to brag!)
What I miss about 1000 Oaks
It is 5-9 degrees cooler
It was my stomping grounds as a teenager
my children live there ( 14-16-18)
Thousand Oaks is with no doubt a great community , no doubt about it and an excellent Christian School- (Oaks Christian)
However all of my children went to public school, they have a great school district , The teachers are great , the programs are second to none, and I have only one complaint, durgs do make there way into the middle and High schools, and I feel more can be done to prevent it.
I cannot comment to much on Simis school district , however I do have friends that are happy with their childrens progress.
Hope this helps.
I posted a video answer on my Youtube Channel: http://www.youtube.com/watch?v=P7WhzJjMwDc
My video commentary gave a better format to really express my opinion.
Also check out my blog post "5 Things to Know before Moving to Simi Valley" http://homebuysblog.com/2009/01/19/5-things-you-need-to-know