Lots of rave comments here I concur with and won't reprise at length.
We stayed three nights in the 2d floor front room. Very comfortable bed and VERY quiet even though it fronted the street.
Even though David has added wifi I didn't use it and didn't miss the internet; too much good music, conversation and stories happening.
Breakfast was great. I've lived in the south for 20+ years and still don't understand grits but David's rendition got me closer :-)
I happened into one of David's kitchen (really) bluegrass jams. I nearly blew out my knee bobbing my foot to the music and it took a couple of days to unfreeze the grin from my face.
David has done a very good job with the restoration/preservation. David's photo-documentation of the project was interesting.
Some thoughts:
The second floor bath was great although, being somewhat unsteady on my feet, the grab-bar assisted step up into/down from the shower was still a bit daunting.
Night stairwell lighting could be bumped up a few lumens.
The collection of artifacts in the kitchen is very interesting but other decor might be dialed-back a bit and still retain the ambiance.
Coffe, tea, cocoa availability would have been nice in the evening.
None of the foregoing would deter me from a return stay, however.

Just returned from a girl's weekend, and thoroughly enjoyed our stay at the Nancy Shepherd House. Our host David was very welcoming and the beds had the most comfortable mattresses I've slept on in a long while! The location can't be beat -- just a short walk to old town where there are great restaurants and shops. We will definitely stay there again.

As B&B owners for more than 25 years, we were impressed by David's restoration of his
colonial home. We know that hospitality and comfort in the rooms are are both quite important.
David was an excellent host and we were quite pleased with our accommodations, which
ecompassed the entire top floor.

Of all the historic VA towns we visited on our recent vacation, Winchester was our favorite.
We really enjoyed the Old Town Walking Mall, which had restaurants that were as good
as we experienced in DC the week prior (David gave us some great reviews of them).

Great little historic row house inn bursting with antiques and personality just a short walk from Winchester's historic pedestrian area. David is a gracious host, I felt immediately at ease here. He is also a great musician and if you are lucky you will catch a bluegrass jam at the inn.
No better base for exploring Winchester!