What is the interior room these windows are in? A bedroom? Sun room? That might make a difference as to what type of window you choose. But in general, I don't think your house needs a complete re-do. I think you simply have to change out the window type. I'd try to get as close to the original type of windows as you can, i.e. if they are single or double hung windows, then replace them with the same. Just be sure that the frames and trim are paintable so you can repaint if you wish.

Maybe 7 awning windows instead of 14 paired windows.

If they don't all need to be operable, mix fixed pane with double or single hung. The fixed pane should look like the operable ones (two panes instead of just one), but maybe this would save some money. Maybe casement windows with grids wouldn't look that different from the existing (from the outside)? Did someone give you a quote on aluminum or vinyl clad exteriors with wood interiors? This is probably the type that would most closely mimic the orginals. You don't want wood exteriors as that is just a maintenance issue. It's a very cute house. :-)

@Sabrina Alfin Interiors thank you! The rooms include the master bedroom and a second bedroom.

@kandrewspa the quote was for fiberglass on both sides...the companies strongly advised against vinyl, and wood was out of the question because so pricey. Thank you!

May be you should go with less of windows?

Or think how repair existing ones?

Fourteen individual windows look very busy to me. I would reduce the number to seven or less.

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I wouldn't remove a bathroom window or a hallway window if there's a staircase with the window unless it's dangerous because it lets light in sometimes you won't need to turn on a light and that's a big house but the Dormer windows you could probably have three there instead of four or two bigger ones it's up to you how much you want to spend on this remodel and I wouldn't get rid of a over the sink window it's nice to be able to look at something why doing dishes when you don't want to look down all the time and if you want you can get rid of the window pane at the Dormer area cuz I don't think you need window pane there it might look nice in the hallway if that's a staircase at the hallway

or

or repeat existing windows

IMO any of the above suggestions would be better than what you have now . We have many of that style house in the town where I live and not one has thta many windows and most are opeable because they were designed to allow hot air to escape .

What you have is really busy. I would try to reduce the number of windows, but would want to consider the aesthetics of the windows from inside as well as outside to make the decision on which windows to replace and how to add some solid space between the windows and still have something balanced from an interior and exterior perspective.

@Amy

I had a double sliding glass door replaced this summer and the first estimate I received was from Anderson Windows and Doors (AKA Renewal by Anderson).

The estimate was $16,000.

I called a few other window and door companies and got estimates, anywhere from $5-10k. The salesmen that came over told me how great their doors were and how they were comparable to Anderson quality, but when I looked at reviews they sucked.

I posted on Houzz and several people gave me suggested brands that were going to be high quality doors.

While looking for local distributers I ran across a private lumber yard/building supply (not Home Depot/Ace/Lowes) that carried a wide variety of doors and windows. I talked to the guy working there and he suggested I call a General Contractor (gave me a name and number) and that said that the GC would probably cost a lot less than the Window and Door companies and could help me decide what door to buy.

When the GC came out he suggested that I replace the door with an Anderson door. When he sent me the estimate I was really surprised - same model number as the Renewal by Anderson estimate, but his estimate was $8000.

My cost ended up being closer to $8,500 due to some dry rot they found when replacing the door.

When I posted back on my Houzz post several of the tradespeople said this didn't surprise them at all. Apparently the "Window and Door" companies often charge double the price.

@Jennifer Hogan That is so interesting, and not at all surprising. Thank you so much for sharing your experience. Just curious - what type of professional do you think we should we use to help us come up with a new design that would also be practical and structurally sound? E.g. architect, designer, etc? We have a relationship with a contractor, but he doesn't realy have an eye for the design/curb appeal aspect.

@Celery. Visualization, Rendering images @BeverlyFLADeziner Thank you so much for these!! Wow, amazing, I definitely think reducing the number of windows is the way to go. Just curious what type of professional would we use to carry out this project? Our contractor not great with the design aspect. Would it be an architect? Exterior home designer? Restoration company? We are new to home renovation and a bit confused about who to consult for this project.

I live in a fairly small town. We have half a dozen builders that build higher end custom homes and they work with a handful of interior designers. The high end custom home developments actually have a designated interior designer to help their clients select finishes. These interior designers are used to working with new builds and both the interior and exterior aesthetics.

I would call some of the builders and ask them if they could refer you to a good interior designer.

I would choose an interior designer over an architect for your project. GCs are not really trained in design like architects or interior designers. Architects are trained in design, but it is not their primary focus like an interior designer. Although the title "interior designer" makes you think that they only work on interiors, their job really entails creation of aesthetically pleasing environments and they generally understand both interior and exterior design elements.

If you look through posts here on Houzz it is the interior designers who often answer dilemmas on how to make the exterior of the home look better. They add dormers or remove shutters or show how to balance the look by extending the patio or adding a front porch, widening stairs or creating walkways. They know how to make things look good.

@Jennifer Hogan very helpful, thank you.

I think the all window dormer suits the house, just half as many:

I love it just the way it is, old houses should be unique. Restoring old windows is fairly easy and cheap but just takes time and patience- heat gun, some hand tolls, epoxy and paint. I can teach anyone how to do it far cheaper than replacement. Even hiring it done is likely cheaper than replacement... If you have some skills you can watch a few videos and teach yourself- I learned in the dark ages by reading books!

Before you get too far down the road, I suggest getting a good look at the window sills. Hopefully you are tackling this issue before you have significant rot problems but it is time to find out the extent of the issues before going further.