I've lived in Cheltenham for 13 years, I moved here from the North East. Coming from one of the cheaper areas of country for housing to one of the more expensive was quite a shock! The nice thing is that pretty much anywhere is fine to live in Cheltenham - even the areas that the locals define as "rough". They probably are rough for Cheltenham, but all things are relative and coming from an industrial northern city, I consider Cheltenham's "rough areas" to be "quite nice"! ;-)
This is my personal view on the areas of Cheltenham, hope it's not offensive to anyone!
Whaddon & Lynworth, Hester's Way and parts of St Paul's are the main areas of social housing in Cheltenham. These are the areas that native Cheltonians tend to look down on (although those who live there are usually fiercely proud of their neighbourhood). You probably wouldn't have a problem living in any of those areas (I bought my first house in Whaddon and lived there happily for 8 years), but they are more working class areas and the local schools tend to reflect that - although both Hesters Way and Whaddon are in the catchment for primary schools with very good Ofsted ratings (not sure about St Paul's schools - don't know it well). That said, houses are very reasonably priced for Cheltenham, not very pretty, but usually well built and designed - good for first time buyers especially.
Leckhampton is very middle class. It's near the posh end of the town centre - which is walking distance from most areas of Leckhampton. It centres around Bath Road, an area of desirable independent shops. It's mostly period properties with a few modern houses from the 1970s-1980s. I've lived in Leckhampton as a renter in three different houses and always enjoyed living here. We're currently trying to buy here ourselves. There are several excellent primaries in the area. House prices reflect the aspirational nature of the area and the schools. The house we're looking at buying is only slightly bigger than my ex-local authority house in Whaddon, not as well built or laid out and yet costs more than double my house in Whaddon. We are basically paying for the area and the schools - house itself is a bit ho-hum, tho' fairly pretty.
We seriously considered Charlton Kings too and nearly offered on a house there. I thought it was fractionally cheaper than Leckhampton. It's expensive because the primary AND secondary school is so good. It's a bit further out than Leckhampton from the town centre - probably a little far to walk into town, but it does have it's own centre and village-y feel, which I liked. Seems to be a mix of period and more modern housing. The best of both town and village living?
St Paul's is on northern edge of town centre. It's a mixed area of attractive period Victorian terraced houses (many student housing), some grander Regency villas and also social housing.
Fairview is an area of period "artisan" (mostly Victorian terraces) on the north-east of the town centre. Attractive, fairly desirable area as houses quite pretty and town centre close at hand, but not obtrusively so. I lived there for a summer and it felt safe and convenient for town. Some of the housing is student housing. Quite a "young, middle class" kind of feel to the area.
Hatherley, Swindon Village, the Reddings, Benhall, Springbank, Wyman's Brook and Oakley are all estates on the edge of town. Mostly more modern houses from 1960's to present day. You get a lot of house (relatively) for your money on these estates. Most people are home owners in these areas, tho' they're not as aspirational as say Charlton Kings or Leckhampton. I lived in Wyman's Brook for a while - a nice, residential, safe feeling area, although perhaps less of a sense of an obvious "Cheltenham" identity than the more period areas of town. Also I found the walk into town not as convenient as I'd have liked.
Warden Hill is sandwiched between Bath Rd area of Leckhampton and Hatherley. Housing is mostly 1960s-1970s-ish era. Not as aspirational as Leckhampton, but a lot more affordable and a good compromise if you like the Bath Rd area but can't quite afford it or want more living space at home.
Pittville runs from town centre upto racecourse, in the area around the attractive Pittville Park. There are some grand period properties in the area, but also some modern housing. I'd say it was aspirational.
Battledown is based around Battledown Hill. There are some very large posh houses on the hill, enjoying great views of Cheltenham. Has a gated community off the hill for really expensive houses! Also, some more affordable housing, particularly at the bottom of the hill where there is a new housing estate near Sainsburys supermarket.
St Marks is also fairly near the edge of town, it's a conservation area of attractive red brick houses. I believe they are ex local authority - but you wouldn't immediately know that, as they are very nice looking houses. Well priced for Cheltenham, good quality spacious houses. Quite a distinct looking area of town. Sometime called "The Poets Area" as many roads named after poets.
Lansdown and Montpellier have a lot of large, Regency houses. Montpellier is in town centre. Lansdown runs from town centre and up around Lansdown Road. Mostly a posh area and looks typically "Cheltenham". A lot of the larger houses have been converted to flats.
Prestbury is on north-east edge of Cheltenham. It used to be a village and still has village feel. Some very nice pubs. Lovely views of Cleeve Hill and easy to reach country walks. Mix of pretty period houses and some more modern housing. Fairly aspirational, parts of it very aspirational.
I'm pregnant with my first, so I'm not too hot on where the good schools are yet. I've been using the Ofsted website to try and work it out! www.ofsted.gov.uk/
Main supermarkets...
Sainsburys on Tewkesbury Rd.
Sainsburys Oakley.
Tesco on Tewksbury Rd, town centre end.
Waitrose near Tesco.
Asda in Hatherley.
Morrisons in Hatherley.
Public swimming pools:
Lido (open in summer) centrally located near Chelt General Hospital and Sandford Park.
Leisure@Cheltenham on Tommy Taylor's Lane, north-east Cheltenham.
This map shows the areas of Cheltenham along with more politically correct descriptions than i've probably just given...! www.cheltenham4u.co.uk/areas.asp