It is a bit of a challenge for sure and a poorly tied in roofline is a pretty glaring thing to ignore... I wonder if it might be possible to have the screened/roofed part of the porch built on (left side in the picture) the side of the house with the roofline matching the existing one? Then you could tie the screened/roofed porch area into the existing open deck. It would also address the re-roofing issue in the future that you mentioned.

If you don't have photoshop you could just print a few enlarged photos of your house and try drawing out a few options with tracing paper overlaying the photo to see what it might look like..

Just extend existing roof over the porch it will look much better.

@GN Builders LLC: Thanks. I'd imagine this would be, by far, the most costly option. Though, I do agree that it would probably look most natural. I'm no construction expert, but due to the lack of pitch on the house roof, I'd imagine the house roof would need to be removed/elevated/re-shingled to make this extension work -- otherwise the ceiling height of the porch roof would be very low.

Since we're going to pull this deck up and re-build one after this porch roof project is completed, I suppose we could just pull approximately half of the deck up altogether, and introduce a few steps down and into the room from the back patio door. That would necessitate walking down and into the room, but would solve the lack of ceiling height -- and trying to screen under the deck boards (the lack of much "crawl space" under the deck would make screening underneath very difficult I'd imagine.

@Flo Mangan: Thank you for reading my post, and for your suggestions. I thought about an awning option years ago, but there just wouldn't be much room underneath it. As it stands, the fascia board/gutters are only 7' from the top of the deck -- so there just wouldn't be enough height, in my estimation.

I should add that we're not too keen on the pre-fab screen rooms available. I know people that enjoy them, but this is a mid-1920s bungalow, and very rustic and unique -- just don't think one of those self-contained rooms would look proper on this house. I plan to use old-growth timbers to use as the posts + beams for this room. I plan to have those anchored to the ground (on top of concrete piers/footers). Appreciate the suggestions though!

swervinvolleyer - that would be a great option, but you are talking $45-50K and I surely couldn't justify that cost for the size home you have. Be careful. Overbuilding your home can come back to bite you at resale time for sure.

@Flo Mangan - It would be pricey, for sure. The good news is that I'm in the remodeling industry, and can purchase most of these materials at cost. I also have a friend in the area that tears down barns for the reclaimed wood. I can work out reasonable pricing with him on the old-growth timbers that will be needed. Still probably looking at a cost of 30-35K, I'd say. Good point on overbuilding. That's definitely something that's crossed my mind more than once. I want to be sensible here as well. We might plan to the home in the future and stay here for the long haul. So many things to think through going forward.

What is your budget for this project? Is this your "forever home"? There might be some other options that would be more cost effective and yet still get you the "outdoor" space you want. For example, you seem to have a fairly good yard? How about a nice screened in Gazebo? It would be less expensive, just as nice an outdoor sitting space and you wouldn't have all the "tie into existing" structure issues, or permitting, etc. Have you considered something like an "out" building. I could also see a building that faces the house with a nice pathway to it, that could serve as your "home extension". It could be of slightly smaller size, but have a slanted, metal roof, for your rain sounds, be sheltered from hot summer sun, and you could make it a 3 season structure. For resale, this could be someone's future office space, music room, etc., etc. Just some options to ponder.

Here are some inspiration photos. This type approach would add more "value" to your property in my mind.

You could design it anyway you want and as large as your property and budget allows. Does this make any sense for you guys? Replacing a roof (shingles) is a whole lot easier than "redesigning" and "rebuilding" the roof of your existing home. Just my .02$

We've had a pre-fab gazebo on our deck for years and love it. Just a metal structure with a fabric roof. We don't have screen walls because we don't have a lot of insects here. Remember if you want to keep out insects you have to have a solid floor too.

In winter, we remove the fabric roof to let the sunlight into the house, which we couldn't do if it had a permanent roof.

You say your deck is in the sweltering sun, so a metal roof may not give you the cool shade that you are hoping for. Is there a shaded corner of your yard that would be a more comfortable location for a free-standing structure?

I think Flo is on to something. A separate building (with a shed roof line mimicking the roof on the right side could look great. You could visually tie it to the house with some beams for vines/planting. If it snugged up against your existing deck, with an additional small deck in front of the out building it could look fantastic. Smaller yard, less to mow!

@Flo Mangan: Your two cents are much more valuable than two pennies are. :) Thanks again for the suggestions. I hadn't had a "studio shed" cross my mind. That's interesting. The back yard would have enough space to support one. Interesting thought. As far as budget goes, I'd say 30K is the high end -- at least in terms of the porch roof/potential screen room idea that I started this post with. Is this our forever home? We just don't know that answer yet. We love this historic neighborhood (it's a prime neighborhood in Lexington, KY), but this home is only about 1000 sq. ft. I bought it in 2009 as a single man. Now that I have a lady in the house, and potentially marriage and a child in the future, there will be a lot of discussions happening in the coming months/years. In five years or so, I'd say we're either selling and moving into something bigger, or we're adding a second story to this home.

If you are going to spend that much money, have you thought of redoing your roofline? I know that would cost a lot, but you do have a low pitch and a funky roof on an addition already and if you foresee replacing the roof in a few years it might be better to get a well functioning roof on the main house that could serve as the porch roof as well.

I'd speak to a real estate agent to get an idea of how much you could expect to get back on the $30M if you sell in a few years. My guess would be, not much of it. It might help the house sell faster but not increase the price.

For less than a tenth of that cost, you could get a freestanding structure to tuck into the shadiest part of your yard, on a slab base, like these for $2000 or $1600 at Costco. Ours is even more modest than these, and it is just fine as an outdoor spot to chill out.

With your life story for the next 4-5 years, I think the studio out building would be a real plus, especially in a neighborhood that appeals to young professionals. That is definitely what I would do were I in your shoes. You would gain most of that investment back in a resale in a good neighborhood such as yours. Then, if you still want to add a second floor, you still have this great structure that could be play room, fun room, etc. Just make sure you get electrical out there if you do it. Easier now than later, unless you have to add a new box to your system. That gets pricey.

One more thought. You don't have to run power to this little cottage, I think you could put solar panels on that roof facing West and get all the power you might need for a fairly small building! How 'bout that?!

@Flo Mangan: That's a great thought! The back yard certainly gets a LOT of sunlight. Good call, and thanks again for your insight on this.

@partim: Thanks for sharing those. To my surprise, she was actually intrigued by a freestanding structure to place on top of the new deck. We've since looked at the Costco website, and there are a couple of them that might be of interest. I'll update this thread once we figure out what we're going to do.

That would be your most inexpensive option. That could be a good option for you.

Glad that was helpful. Where I live (Toronto Canada), they're starting to set up the model gazebos at places like Home Depot. It's a good idea to get inside one that is the same size you are thinking about, to see whether it fits your needs.