A more modern treatment for the deck railing could help. Glass, cables . . . something more sleek.

I'd stick to something that blends better with the surrounding houses - NOT modern farmhouse. Most like the beach / cape cod look with shingles and light trim - but done in a more modern way. A good architect can help you and visual this dream!

Which Southampton is this, by the way? Might help with suggestions.

I think if you focus on the deck and railing, the exterior will look more updated. The steps from the deck to the beach side look narrow and steep. They can be improved. Maybe a landing will help. The walkway in the back and the front of the house should be more substantial.

Does the siding need to be replaced? Is the decking in good shape or does it need to be replaced? How about windows? If she's looking to completely redo the exterior (not just a facelift with paint), then consider new, larger windows. Gray shakes would look great with black window frames with white trim and a gray weathered wood-look (Trex) deck. As someone suggested, you probably need an architect for that many changes.

I don't know what your goals are. Unfortunately the form and "bones" of this house are very ungainly; the proportions are not good. It looks like a builder's weekend or beach house from the 60's-80's.

You can change exterior colors and/or materials, but nothing is going to change the overall form and awkwardness of the house short of a major architectural remake.

If it was my house, I'd make sure the exterior is sound, dry and in good repair, and then spend my available money on improvements to the interior and/or usable outdoor areas.

The Hamptons are a lovely place, and the joy of this house is being there. There's no joy in the architecture.

Nothing you do is going to turn your mothers house into your inspiration picture. Not possible. And adding shakes is going to make the house look like you put fur on a Komodo Dragon.

The picture suggestions do look good but they won't work with this house. I think Virgil gave you good advice

The new owner needs to embrace the contemporary box style. Look around the neighborhood with google streetview to see if there are other houses in this style with appealing color schemes. A very large boxy house painted bright white with black trim is not going to look at all like the inspiration photo. A light silver gray (lighter than the roof) with charcoal trim might look better.

Work with the style, not against it.

Well...if it was my house I certainly wouldn't make the exterior "white" and call more attention to it through a visual contrast of the bright white with everything else around it.

I would want the house to "blend" and be a low key (not a high key) color and to be a reasonably middle or middle-dark value.

Whatever exterior finish you want--existing cement plaster repainted or new shingles stained--make it middle to middle-dark value.

The house is simply not a light, white Modern or International School showpiece, nor a trendy white with black window frames HGTV glamour house of indiscriminate style:

A house on the beach in the Hamptons? What could be better?

Don't replace a wonderful ipe deck, but modernizing the railing and getting rid of all the clutter on the deck is a good start. Then find that affordable ( is there such a thing in the Hamptons? ) architect.

Good luck with your project and keep us posted.

Agree with keeping the IPE decking. But I would do Feeney cable rails, with a composite/PVC white rails/caps, and posts. It will modernize the look. I Recently did one with slight similar shaped house.

I also found another project I did, where they used wood for the decking, and top railing cap with feeney cable rail as well. White timber tech post sleeves. I made a pergola to go over the deck and they bought one of these really cool colored sunsail awning to go onto. Like someone else mentioned the side stairs could be better with divided landings, and wider. As far as the siding I know its very expensive but hardy plank would last the longest with minimal maintenance. I also think that if something was done with bottom of deck, either columns, enclosed porch with deck underneath would change the whole appearance of the house, along with different rails.