Strolling from gallery to gallery is one of my favorite things to do. I started my career as a gallery administrator where I was lucky to start a (small) collection. The first consideration when looking to purchase work is to familiarize yourself with what galleries offer.
If you're looking for contemporary photography target galleries that specialize in contemporary photography. If you're looking for a Japanese tea bowl find galleries that specialize in fine art pottery. To name just a few more ways that galleries delineate themselves, you can search for galleries that specialize in American, European, local, regional, or international work across all mediums.
While most galleries subscribe to a white box, minimalist viewing room philosophy, they almost always have extensive selections of work stored unframed in flat files and meticulously stacked within storage closets. If you interested in seeing a particular genre, style, medium, or size of work, gallerists will be happy to show you what they have. They may start the process by showing you catalogs from previous shows to gauge your interest. The very best part about buying work from a gallery is that art dealers are in love with the artists they choose to represent and often share thoughtful information surrounding the work and the artist's life. They are able to articulate why a piece is particularly striking or why it may be different from others.
The majority of art galleries are small proprietorships and operate with significant flexibility and their own unique agenda. I've worked at galleries that will only sell to people they have researched, to galleries that will personally deliver works to your home so you can live with them for a few days before making a decision. Galleries will also allow you to pay for a piece over time in many cases.
All prints including photography are sold in limited editions. Being limited, in part, is what creates the value of the edition. The larger the edition, the less expensive. The smaller the edition the more expensive. Prices within editions get progressively more expensive as they sell and when the entire edition has sold the value of all pieces within that edition generally increases.
Buying art from a gallery is a personal, well serviced transaction. You should expect great customer service, honesty, documentation of the artwork including a signature on the piece, an artist bio and any supporting literature, framing services for an additional cost, delivery to your home or office, and in many cases custom installation of the work itself. Lastly, do not be intimidated. If you are generally interested in learning and exploring artworks ask as many questions as you wish and develop a relationship with a gallery!
Image: Joan Clancy Art Gallery

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I've always wondered about the flexibilty galleries have in pricing. 20 years ago, I purchased a pastel for $1500 with my tax refund. I love the peice, and it's turned out to be a kind of crystal-ball, eerily predictive of the life I'm living today. Today, the same artist's work goes for nearly three times that price. I'm still in love with her work and so is my new husband. We'd love to aquire more pieces, but the increase in the value of her work is a bit prohibitive right now. It's nice to know that we might pay for something over time.... but what about dickering over the price?
kimg924: depending on the gallery/artist/inventory there can be flexibility on price, and more commonly on bulk purchases or several works within a series.
Sometimes the artist will offer a discount if you have purchase a painting from them before. This happened to me when I went back to the artist the next day to buy a second painting, she gave me a dicount of 25%.
@ kimg924
I work at a major New York gallery and 10% is standard discount for most major galleries. The net is sometimes less depending on how much you buy and the relationship with the gallery and who you are and where the piece would be placed, but I would always ask for the base 10%. It is pretty much built into the retail price, and the artist gallery split.
I second that. 10% is standard. If you buy more than one piece sometimes there is room for more. Ask for lower prices buy asking for a discount - not by haggling in a sort of "hey i'll give you this $$ for it, final offer." For contemporary photography, the standard split between artist and gallery is 50/50, which will give you an idea as to why a gallery may not budge far beyond 10%. They are only getting 50% of the retail price to begin with.
Great tips, I work for an art gallery too and buying a unique piece doesn't have to be expensive or intimidating and with a little education it's often a good investment. There is also a great resource/magazine called New American Paintings that features the work of emerging artists often at very affordable prices.