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rinqreation I picked a few colored craftsman homes, not sure why though.. I like the first and second's colors best for your house (blue-grey with cream or soft mustard yellow with cream).

Jayme Hobbs Yes it could-these have somewhat similar roof lines as yours.

rinqreation You could give it a more modern/contemporary look with greys and some orange.

Jayme Hobbs Pic with similar color to which u mentioned

Jeffrey Brooks Interior Design Your place is perfectly situated and proportioned to make over in the craftsman style. Looks to me like the first choice color composition is best. Paint the shingled portion in a natural seasoned cedar color. I can't make out what the ground floor side walls are but, paint all of the sections which are shingled like the fron peak in the same color. Other walls that are a different material,should get the same color but a little darker. Fatten the columns, resurface the front concrete porch with random sized slate stone. Get rid of the shutters. Repaint your trim in a warm white, or be bold and use a dark charcoal or a dark "dirty" green. The fron door is a nice clean style so you can add oomph here by painting it a different color from everything else. Again, be bold and use a deep red or go safe with warm white. If it works in your budget, install hand railing across the front and again at the deck. If the deck is in good shape use an opaque stain. Also, if it's in budget, you might extend the side deck and privatize it with hand railing since it looks like the house would be more "finished" and you'd have more of an outdoor-room.
Whatever you do it looks like you have a really sweet little place to enjoy!!!!!

losthorizonlisa Thanks everyone. I do like the crisp look of the cedar and of the gray, however, my last 2 homes were neutral gray with soft green and charleston green trims and I'm looking to shake up things. I was thinking with so many trees around the house it would blend in nicely in the green shade. Originally, a happy pale yellow was recommended with blue trim, but there are already 6 yellow houses on my short street. Will keep you all posted.

Jeffrey Brooks Interior Design Lisa, How about hitting the library before you select your colors? I get it that you'd like to avoid Grays because you've had that before. The thought that I have when I hear you say that is you should look three or four times before you leap. Making a choice because you want to change things up might influence you to eliminate the thing that may be the most powerful for the house.
Deeper toned exteriors are more resereved, have a serene feeling, and convey privacy. I guess that if you're going to go "cottage" with the property "ice cream" colors will certainly work I just think that you run the risk of winding up with a ginger bread house which look Victorian.Maybe use a bolder Gray/Green and one interesting color to highlight the details.
Suggestions: Benjamin Moore Storm Cloud Gray #2140-40 with BM "Pale Sea Mist" #2147-50.
"Jojoba" #AF-460 with "Brick Red" #2084-10 (Window frames + Door Frames) , "Spa" #AF-435 (on Doors, Shutters, Garage Door).

Ironwood Builders losthorizonlisa, I guess I am, as usual, late to the show. I want to weigh in on the remodel of the exterior a bit. I know you have tracked some of the ideas put forward on other Craftsman conversion threads...I would like you to plan the architectural changes and detailing prior to committing to paint colors. A comprehensive construction plan with specifications will prevent costly backing up and changes in the course of the renovation. A clear and concise scope of work and detailed elevations will allow the carpenters (or you) to price out and be accountable for making your vision a reality. Help with elevations is a mouse click away here on Houzz...or you can do as I did and sit for a week and teach yourself a basic CAD program...or you can be really artistic and draft it all out by hand. Regardless, discussions are great, but talking, ideabooks and arm waving only go so far towards getting a project done. The best way to communicate with contractors is with plans and real specifications. I know you have been making lists...get them organized and start the drafting process! Jeffrey Brooks advise about research is spot on. I'll check back in occasionally to see how things are progressing...if you have specific questions, post them, we'll be here.

losthorizonlisa Jeffrey, I laughed out loud when I read "ice cream colors." Well worded advice to do what is most powerful for the house. Definitely not leaning towards "cottage" or "Victorian"... want the crisper feel of craftsman.

Someone told me darker colors promote more mold growth... is that true? Where the house is situated is very shaded and humid.

And Ironwood, what a thought... have it well planned out?! You are right... I usually get an idea and the work gets done piecemeal. Fortunately, the changes do look good. We always say "sequences, sequences, those darn sequences" because one wild idea leads to a laundry list of everything else that needs to be done FIRST. Frankly, I don't even know what you mean when you say elevations and "scope of work"... I thought that was for new building and fancy renovations?

Ironwood Builders Lisa, In contracting, a written Scope Of Work is often included in the addendae to the base contract. It specifies in words what the plans show, but don't always express... Like there may be 6 corbels shown on the elevation of the front facade (a vertical rendering of the plan is an elevation and we do both interior and exterior to provide direction). The plan may include a detail, a larger drawing of the corbel, but may omit something basic (or not). The Scope can be used to clarify this...say the detail says cedar corbel. The scope can call out grade, rough sawn, knotty or Grade 'B' and then a less durable or less expensive material may not be substituted except by change order. The Scope is part of the contract. Every contractor you hire should have a copy... No arm waving and verbal agreements. If you are all DIY, the Scope you write helps organize you too. By thinking through what has to happen before you get to applying paint and putting it down in sequence, on paper, you become more effective with your most precious commodity, your time. Proper prior planning prevents P poor performance.

Ironwood Builders One more thing...a poorly planned "small" job can eat you alive. I hate spending $20K to complete a job I bid $19K on...the same is true for your project, without a plan, even a sketch, how do you figure out that you need to pour bigger footings for your wider tapered posts...that are sitting in the front yard, just delivered? So, your "sequences" mantra can actually be a hard copy plan. Something for your scrap book after. A record of the achievement.

Jeffrey Brooks Interior Design Hello Lisa, the question of mold and how darker colors may be more prone to it's growth is foreign to me. My own place is painted in a Camel color and trimmed in Charcoal with the doors in Terra Cotta. The trim is in a warm white.
I haven't seen any evidence of mold in the 5-6 years since it was repainted. This house is a 1868 built Queen Anne (late Victorian) which has a very classical look . We're surrounded by old growth Black Walnut, Red Maple and Pin Oak so the house is in the shade for much of the day. I have to say that I like the effect of our color combination because it has a crispness and the deeper tones make the house look harmonized with the colors of our property.
The house is power washed every spring to keep it clean which might keep mold from accumulating.

Ironwood Builders We have never had a problem with mold growth on dark paint. i have used Microban additives to paint to retard the north side "moss on the tree" effect.