LINQ aggregate and group by periods of time

You could round the time stamp to the next boundary (i.e. down to the closest 5 minute boundary in the past) and use that as your grouping:

var groups = series.GroupBy(x =>
{
    var stamp = x.timestamp;
    stamp = stamp.AddMinutes(-(stamp.Minute % 5));
    stamp = stamp.AddMilliseconds(-stamp.Millisecond - 1000 * stamp.Second);
    return stamp;
})
.Select(g => new { TimeStamp = g.Key, Value = g.Average(s => s.value) })
.ToList();

Above achieves that by using a modified time stamp in the grouping, which sets the minutes to the previous 5 minute boundary and removes the seconds and milliseconds. The same approach of course can be used for other time periods, i.e. hours and days.

Edit:

Based on this made up sample input:

var series = new List<Sample>();
series.Add(new Sample() { timestamp = DateTime.Now.AddMinutes(3) });
series.Add(new Sample() { timestamp = DateTime.Now.AddMinutes(4) });
series.Add(new Sample() { timestamp = DateTime.Now.AddMinutes(5) });
series.Add(new Sample() { timestamp = DateTime.Now.AddMinutes(6) });
series.Add(new Sample() { timestamp = DateTime.Now.AddMinutes(7) });
series.Add(new Sample() { timestamp = DateTime.Now.AddMinutes(15) });

3 groups were produced for me, one with grouping timestamp 3:05, one with 3:10 and one with 3:20 pm (your results may vary based on current time).

I'm very late to the game on this one, but I came accross this while searching for something else, and I thought i had a better way.

series.GroupBy (s => s.timestamp.Ticks / TimeSpan.FromHours(1).Ticks)
        .Select (s => new {
            series = s
            ,timestamp = s.First ().timestamp
            ,average = s.Average (x => x.value )
        }).Dump();

Here is a sample linqpad program so you can validate and test

void Main()
{
    List<Sample> series = new List<Sample>();

    Random random = new Random(DateTime.Now.Millisecond);
    for (DateTime i = DateTime.Now.AddDays(-5); i < DateTime.Now; i += TimeSpan.FromMinutes(1))
    {
        series.Add(new UserQuery.Sample(){ timestamp = i, value = random.NextDouble() * 100 });
    }
    //series.Dump();
    series.GroupBy (s => s.timestamp.Ticks / TimeSpan.FromHours(1).Ticks)
        .Select (s => new {
            series = s
            ,timestamp = s.First ().timestamp
            ,average = s.Average (x => x.value )
        }).Dump();
}

// Define other methods and classes here
public class Sample
{
     public DateTime timestamp;
     public double value;
}