From what I have learned, that charming look of ivy growing over a house can be safely done if certain care is taken. Using a type of ivy that climbs using "suckers" (little suction cups that allow it to cling to a surface) is relatively safe, whereas ivy that climbs with tendrils (little roots that dig in and wrap around whatever they can) can quickly turn into a sort of cancer.
In any case, care must be taken, and pruning must be done. I would not recommend any type of ivy for a house clad in siding. The ivy can too easily get behind the clapboards and cause real problems--water intrusion, loosening of the cladding, etc. Masonry is a much safer material to train ivy up. But it should always be pruned away from window and door openings, and stopped before it gets to any wood cornice work, downspouts, or chimney flues, where it can easily work it's way into places it should not be and result in expensive damage.
English Ivy, for these reasons, is best avoided, but a Boston Ivy that is properly cared for, can give the house that charming appearance. So weigh the issue of ivy carefully before you plant it, most ivys propegate very easily and can be quite difficult to get rid of.
At any rate, here are some wonderful ivy covered houses to inspire:
Notice how the ivy has been kept away from the windows and shutters here.
The facade of this house in Savannah is nearly completely covered in ivy, and feels as if it has been there for centuries.
A gorgeous ivy-covered Georgian.
A classically detailed cottage with ivy covered walls--is that wysteria or bouganville climbing over the portico?
Ivy lends a feeling of permanence to this Tudor, and has been carefully pruned to stay on masonry walls.
The first floor of this Dutch Colonial is anchored to the site with climbing ivy.
The stone walls of this house are softened with ivy. Love how the oval windows "pop" in the greenery. (via The Enchanted Home)
So, what is your take? Is ivy worth the risk?
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