Hi Sunshinefordays
You're looking at very practical areas for Waterloo/Clapham Junction.
I love SW London including all the areas you are considering and other more expensive ones like Barnes, but I'll try to answer your questions in as much detail as I can.
Yes, we really like Teddington. It has some nice shops in the high street and a beautiful riverside and park. I think it 's got a very good service regarding the number of trains into Waterloo, but they're all the slower sort, taking around 40 minutes I think - whereas Surbiton has a lot of faster ones than that. Richmond has the great advantage of the tube, although specifically for Clapham / Waterloo that isn't relevant.
Surbiton is a much more modest place than Richmond; the shops, the feel to it and the people. It's a more every day living type place, feels friendly and relaxed but is definitley massively less 'posh' or 'exclusive' than Richmond. As someone mentioned above, Richmond attracts tourists, Surbiton doesn't.
Richmond has 10 times as many shops as Surbiton, it's much bigger, it's wealthier and more sort of elite. Hugely more expensive too.
In a way, it's unfair to compare Surbiton and Richmond though because Richmond is the main shopping area in the borough, whereas Kingston is the main shopping centre in the borough of Kingston (where Surbiton is).
Regarding where in Surbiton to live, I agree with others who suggested the Maple Road area or the roads between Surbiton and Kingston.
Maple Road has a villagey feel, with some nice restaurants, a café and is very near the beautiful riverside but also the station and the more normal high street shops. It's limited though, you can't compare it to the fabulous Richmond.
The area between Surbiton and Kingston does sort of include Maple Road, and is nicely positioned near to the excellent Surbiton Station, the riverside and the town centre of Kingston with lots of shops and riverside restaurants.
The wealthy part of Surbiton is called Southborough, where the houses are very attractive, large, and there's grass between the pavement and road as well as trees (that always looks so nice and more rural I find).
The area called Berrylands (KT5) has 1930s houses, mostly detached and semi-detached. It feels safe and calm, but to me seems a bit boring. The part of Berrylands nearer to the northern part of the Ewell Road is best, where the walk into Surbiton is fine. I'd happily live there and actually suggest you look at that area because you'd get much more for your money than in the Maple Road area and astronomically more for your money than in Richmond.
Tolworth is sometimes included under 'Surbiton (KT6)' but isn't near enough to the river or station. I wouldn't move there.
People also suggested Kingston, and I agree, it's a wonderful place. However, the station doesn't compare to Surbiton if you need to commute to London. That's why I'd suggest the Surbiton side.
To sum up, if I were house hunting and my budget was unlimited, I would choose Richmond or Kew. I think they would also feel more similar to what you're used to with the type of shops and feel. On a much more limited budget, I'd happily live in the Maple Road area of Surbiton, the part of Berrylands near to Surbiton, or the roads between Surbiton and Kingston, but they are definitely less desirable than Richmond or Kew.