Following my unrealistic gut instincts, I'd stay and add on. I love older neighborhoods and trees and space, and I hate HOAs and tract housing. (I would have stayed in my own 900 square foot 2/1 house on 1/3 of an acre forever if I could have.) However, there are too many variables to know whether this is a smart choice or financial suicide.

Just in case: We live in a small town outside of Dallas. Town is showing growth (cute new shops on main street), new housing communities being built around Downtown, top rated schools. All good things. Our house just hit 100 yrs old and, honestly, if each were fixed up it would be a really cute street. There’s just mid-lower income/elderly living in these houses so there isn’t much motivation to improve.

New community has the same schools.

Are those the only two options? I'd never move to a small lot like that, no matter how great the house was. I'd get a realtor to send you listings so you can see what else is out there, spring is almost here a lot more homes will go up for sale.

That’s what’s kinda bugging us. Even if we dropped 100g’s we‘d still be under the new build price (we bought it for 129) and have the yard to boot.

itsourcasa- yep, I’m keeping my eye on the market to see if we can upgrade within the school district

I live in a small town that is popular right now and when we moved here the small homes like that were held by older people that didn't see a need to fix them up, but they become a hot commodity as they moved/passed and others did fix them up so now it looks nice. So if your town is like mine then I'd add on if it could be done so as to work well with the house and the layout of the house. An addition that doesn't work well with the house and just adds a room and bath would not be appealing.

My guess is if people see there are nice houses nearby when the other houses go for sale that they will likely be fixed up as well, but there are no guarantees.

I would move. 3 boys in 1 bedroom would be the death of me. 💀

2 bedrooms and a bath would be long-term. That gets my vote.

That’s what’s kinda bugging us. Even if we dropped 100g’s we‘d still be under the new build price (we bought it for 129) and have the yard to boot.

And you'd most likely be the most expensive house on the block which means you'll never recoup your investment. You never want to be the most expensive house in the neighborhood or block.

If all the other houses on the block are also starter or retirement houses like yours, it will never rise in price.

Another thought is how do you intend to add onto a lovely old 100 year old house and keep the charm and what makes people want to live in it?

cpartist- By flipping the house to its original floor plan. If you look up houses from the 20’s you’ll see that the 2 bedrooms straddle the bathroom. The previous owners flipped it so that the bedrooms are now the living room and kitchen with the bathroom between. By taking down the nonload bearing wall separating the current bedrooms we could open the floorplan to what it was while adding a kitchen and stairs to a bedroom in the additionnon the back. Original pine floors and headboard ceiling remain. Craftsman moumolding is added and original 5 panel doors (currently in the shop) put back in.

Current kitchen is onlya couple cabinets and the stove so not a rough demo

That sounds like a lot more of a remodel than just adding on a master. I have owned 2 small houses. The 2/1 could easily have been a 3/2 by doing a garage conversion (common in that neighborhood), and the 3/2 was a 2/1 that had been expanded by turning the 1932 sleeping porch into a new master suite. I could be wrong, but what you are describing sounds a lot more complicated, even if it does ultimately get the house closer to its original floorplan.

I would shop around for a house already fixed up. I think it would be a huge challenge to remodel a very small house with three boys under foot. And additions/renos always take longer and cost more than you expect.

I would rather live in a one room cabin than in an HOA were if you sneeze in your back yard 4 neighbors say God bless you. I personally would contact an agent to send you non HOA homes when they hit the market.

I would sell and look for an existing home that has the bedrooms you need. Teenagers won't use the yard like they did as children, but do need privacy and space inside. I can't imagine there are no alternatives to the planned community. Even if you have to do some work to the house over time, you can find something that works. Look ahead a few years and make sure the home will work for you after your children grow up also. The HOA community could be a great way for you and your kids to make more friends and have a place like the pool to hang out.

If the master is significantly larger than the small bedroom, swap rooms with the kids. I am not a fan of big houses on postage stamp sized lots with HOA rules to obey. I would add on to the existing house if I couldn't find a larger existing house that would need less work but still have a decent sized lot.

If you spend $100K on the remodel, how much will the home be worth? The reality is people only stay in their homes about 7 years. So while you feel like this lot is great now, you probably won’t be there in 10 years. As mentioned earlier, swapping rooms with the boys can help ease some of the tightness for now. Then keep your eye out for another older hon on a larger lot to come on the market. The new area is not your only option, just maybe your only option right now.

Weedyacre- Loved the link! Your floor plan is just like ours, with the bedrooms being our living and kitchen and a hall running between your living/kitchen dividing them into the bedrooms.

Have you considered the third option of building new? If you like your lot build the house you want on it.

By flipping the house to its original floor plan. If you look up houses from the 20’s you’ll see that the 2 bedrooms straddle the bathroom. The previous owners flipped it so that the bedrooms are now the living room and kitchen with the bathroom between. By taking down the nonload bearing wall separating the current bedrooms we could open the floorplan to what it was while adding a kitchen and stairs to a bedroom in the additionnon the back. Original pine floors and headboard ceiling remain. Craftsman moumolding is added and original 5 panel doors (currently in the shop) put back in.

Amy- I think with the thought for original design and care for character and your obvious heart in your home you may have answered your own question. Just looking for reassurance? I think you'll gain the space you need for awhile and still get to keep the neighborhood you love.

If the majority of neighbors are elderly, the chances of young people moving in and fixing up those houses before too many years are great. I would never worry about my home simply as investment. You can't put a $$ amount on having a space you love, mature landscape and walkability. You have many years to enjoy your addition and unless you plan to try to sell the minute your kids go off on their own, that gives your neighborhood even longer to improve.

Maybe you can buy some of those old houses and flip them as they come available and make it the neighborhood you desire.

I'd add on in a heart beat.

Stay and see how the neighborhood improves. Staying means option 3: swapping bedrooms with your children.

I'm not completely disagreeing with cpartist's comment above, but let me offer another perspective. We bought a 100-year-old 2/1 house 7 years ago as a temporary crash pad, and then ended up deciding to try to downsize and make it work. Taxes were low ($700/year), and cleaning was easy.

It was a bit too snug, so we added on 200 sf. We paid more for that addition than we will recoup in additional sales price, but (1) it enhanced our quality of life, and I think that needs to be considered along with ROI; and (2) it allowed us to stay in our low-tax home instead of upsizing and paying another $1000/year in taxes, which helped offset some of the "overimproving."

Obviously resale is not the only question. The other questions are what will happen as the old neighbors move out.

Another thought is how do you intend to add onto a lovely old 100 year
old house and keep the charm and what makes people want to live in it?

Very carefully, as you did when you built your new Craftsman. Here's how we did it.

Yes I saw your gorgeous house. You did it proud but not everyone does. Too many people think they should do whatever is the latest and greatest according to HGTV.

Hoping that a big addition involving a kitchen and a bathroom is only 100K is a bit of a pipe dream. Better keep looking at existing home sales for the 2x bigger house.

If you don't have an upstairs already, consider building up. Could you create a full upstairs over the downstairs to add two large bed rooms?

Across the hallway from a middle circular stairs, add a modified j&j bath: each bedroom would have a private powder room but would share one bathtub shower combo.

You could put the tub/shower combo EITHER

,,, between the two powder rooms or

... put the two power rooms side by side between the two bedrooms and then and put the tub/shower room between the pair of powder rooms and the upstairs hallway.

Add a standard four/twelve slope roof over that two story part but then add two full length porches on two opposite sides of the house with a porch steep roof on each side that meets the edge of the standard four/twelve roof .

How your home is oriented to the sun would determine if you would even need a dormer for the bedrooms which could have their own window on each "gable end".

You could add a wide dormer in the steep roof for the stairwell on one side and a pair of smaller dormers for the modified j&j powder rooms on the other.,

Would your decision be clearer if money was not a consideration?

I would never live in an area with a HOA so for me it would be a no brainer. We bought a house in an old area where most of the homes were not taken care of by the time we finished renovating that area had become an up and coming place for young couples to live we made really good money when we sold. I do believe you need a bigger house for sure and 1/3 acre allows you to expand nicely.I would add on .

I also vote for moving the kiddos into the master, *if* it can better accommodate your boys and your husband is on board with the idea. :-)

As an adult, I've only ever lived in tract HOA neighborhoods with 1/5 acre lots, and I would love to have more space between houses, as well as less restrictive "guidelines" dictating to me what I can or cannot do with my own property. You would think that folks would have greater incentive to be considerate to others when they are closer together, but sadly, that hasn't been my experience. :-(

there has to be a 3rd option. Can't you buy an existing 3/2 house in the area you like?

I would move - as others have posted, there must be other alternatives.

The only time building an addition makes sense is for very specific neighborhoods in which there are old homes built for poorer people in neighborhoods that have become attractive to wealthier people. For example, certain neighborhoods on the West Side of Los Angeles or Santa Monica.

I also have no issues with an HOA because it prevents me from having neighbors doing whacky things on their property. But then I have no particular need to do anything in my home except live in it like a normal person so I've never felt restricted or constrained by my HOA.

I think large yards are over rated especially in a community that seems to have communal facilities like a pool. How small are the yards exactly because that's relative of course. I've seen some ridiculously small yards but when I've watched shows like House Hunters, I've seen people claim that fairly large yards are too tiny for them. I would imagine your 3 teenage boys would prefer private space inside the home AND communal space - especially a pool - for socializing.

And that's not factoring in the sheer aggravation of doing this kind of large project. It's guaranteed to go over budget versus knowing exactly what the cost will be when you purchase an existing home.

Surely there has to be some other option. Are there no other desirable neighborhoods where you could find an existing house?

Another perspective: family members moved from an old, charming, in-town, close to everything house. They built a lovely, character-filled house in an HOA community and actually had a slightly larger lot than in town. But, the set-up of the lot layouts in the community meant they were living in a fish bowl. This drove them nuts, and they ended up selling.

IF you can really do the remodeling for 100K, I'd take my chances on the neighborhood turning over and becoming more desirable when younger families start moving in.

I second the idea of at least temporarily putting all the boys in the master and you taking the smaller bedroom.