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In northern James Island you have deep water docks along the ICW leading to downtown and the City Marina and the harbor and the Stono River on the other side. You have at least two boat ramps steps away to under a mile away from where you might live. A Muddy Waters Coffee shop and the Crab House(waterfront) Restaurant and J Paulz tapas bar and the Mustard Seed REstaurant and other restaurants and the Terrace Theatre are all steps away. Just one mile away and an easy walk over the drawbridge over the ICW to South Windermere in West Ashley is a Starbucks, an Earth Fare (a smaller scale Whole Foods) and more Restaurants, an artisan bakery and shopping and a library (and even a tackle shop). There are marinas in West AShley where you could keep a big boat and another waterfront restaurant called CAlifornia Dreamin' right on the harbor looking across to downtown Charleston. For the beach there is Folly Beach south of James Island which has plenty more shopping and businesses along the way including a Lowes.
I think Northern James Island is much more walkable to all of what you are interested in with the possible exception to the Groves section of Mount Pleasant which would be farther to the marina at Patriot's Point.
I like to sail and I was looking for much of what you are. I joined a community sailing program at the College of Charleston which uses space and keeps their boats at Patriot's Point in Mount Pleasant. While the marina is a nice facility, it is very exposed and expensive to keep your boat there. Also the ships coming into the harbor pass by really close to the marina. The marinas on the peninsula and West Ashley are more protected and are much closer to a Starbucks either in West Ashley or downtown
At Isle of Palms, I'm not sure if you are walking distance to a Starbucks AND to boat landings and marinas unless you don't mind walking a few miles or more.
Cross off IOP, there's nothing available in the $225k price range with that square footage besides timeshares.
Mount Pleasant has roughly 10-15 townhomes, condos available that would match it.
James Island would give you much more options.
Other than James Island, your request is not going to be easy to fulfill. Especially the part about walking to things. Downtown is the best walking/biking area around here.
Mt. Pleasant is horrible for biking except on a couple of streets. Also, downtown and mp are pretty pricey.
IOP starts at prices way higher than $200k so not a chance there. Plus, they don't really have a drug store, Starbucks, or etc. Not convienient except to the beach.
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