No matter where Wendy and I find ourselves we are always scoping local houses for sale, and last weekend was no different. We told you a little about our quick weekend trip out to the Eastern Shore, and while in St Michaels, Maryland, we just happened to be taking a stroll through their quaint and historic city streets during the prime period for open houses, about 2:00pm on Sunday.

Whenever we spend any time on the Eastern Shore we like to imagine ourselves buying a second home where we could spend weekends lounging with friends by the water. Though our available money, schedule, work, and commitment to working on our current home puts a major wrench in the plans of beach home ownership, we like to daydream nonetheless. And lucky for our daydream, we happened on an open house that may be just about the perfect weekend cottage for us.

There are a few streets in downtown St Michaels that are more or less the epitome of an historic shipbuilding town. The streets are packed full of beautiful and nicely restored homes built 100-250 years ago.

Each is unique and not particularly grand, but they all have a quality of livability to them that makes them all very inviting.

The street our open house (see, it's already "our" house) was on is East Chestnut, which extends from the main street of Talbot and down a few blocks to the water of the marina inlet. As you can see, this street exudes character.

The home we toured is near the end of the street and is a very attractive white clapboard house with black shutters.

Known as the Aaron Dyott House (links to a Maryland Historical Trust writeup on the house if you're interested), it was constructed circa 1850 with additional improvements towards the end of the 19th century. There are plaques on the front of many of the homes in this area that indicate some aspects of each home's history.

This particular house has three bedrooms, three and a half baths, a nice backyard area, and a carriage house complete with guest cottage and potting shed. To say this house is pleasant is a bit of an understatement.

We had Lulu with us, which meant we switched off touring the house. This allowed me to sit on the front porch and take in the views.

From the porch you could actually see the marina inlet to the right...

...and several other very nice homes across the street.

The home had quite a few original and intact architectural details and has obviously been very well cared for over the years. Take a look at the intricate work in the wood above the edge of the porch.

The details continued inside, like with this Victorian doorbell mounted on the back of the front door. Probably added somewhat recently, but it's a period item that looks great and actually works.

The interior of the home is a bit of a tight and winding layout, but this is something I find particularly appealing about historic architecture.

The real estate photos are shot with a very wide angle lens that makes the house look fare more open than it actually is. While the home is rather large, the wide angle doesn't properly capture just how comfortable and cozy the home feels.

There is a front and back staircase, though neither are particularly large, and the first floor powder room is tucked neatly under the back stairs.

The kitchen is the largest room in the house and is quite functional. There's room for updates here and there, but the whole first floor is in great shape.

The front staircase takes you up to a small hallway with storage closets, and to the two front guest rooms in the home.

These two rooms are side by side and have great views out of the front windows as well as closet space, a rarity in older homes. Additionally, there's a nice full guest bathroom that is situated nearby these rooms.

The back portion of the second floor houses the master suite.

It's a nice layout that allows you to close the whole master suite off to the rest of the house and just access it via the back stairs.

One thing that's very nice about the master is the tiny balcony off the back that also has a few additional views of the water. Not too shabby.

Look at the great views this room also has of the very nicely maintained and relatively spacious backyard.

I can picture great summertime cookouts and parties back there!

One of the most interesting and unexpected features of this house is actually the carriage house that sits at the back of the property. That's the front of the carriage house in the photo of the backyard from the master. This building is currently setup to house a game room on the first floor...

...and a media/theater-ish room on the second floor.

The carriage house also has a wet bar and a bathroom in the main living area. I think you could reconfigure the floor plan to actually get a decent sized guest house with two living areas and a kitchen out of this building. Or perhaps it's the perfect size place for an upstairs guest area and a first floor wood shop and storage area since there isn't a basement in the house.

In addition to the living space, this carriage house also has a one car garage and a great potting shed type area with plumbing and a sink. I can imagine the vegetable garden we could grow here!

In all, this house is quite amazing. It's historic, has a great configuration, plenty of room for guests, and all of the amenities one would need to relax. Though it is very nice it is being solid "as-is," it has room for updates in the kitchens, bathrooms, and carriage house, and there are some major cracks in walls and other maintenance issues I can see that would easily keep the DIYers in us busy. And really, it's hard to beat a front porch where you can hang out and watch the boats drift by on a warm summer evening. I could get used to it.

And now for our game...

Would You Trade Buy it as a Vacation Home

Yep, a slight twist this week. Since St Michaels is about one and a half hours away without traffic, we obviously can't just trade outright, so we're taking a different approach. Not really worrying about if we can afford it or not (because we never pay attention to price in our game), we're asking the question "could you see yourself buying this home as your vacation home?" It's a fun hypothetical, sort of like our "what would you do if you won the lottery" type of question.

Alex: Sold, done, it's mine! I love this house. The age of the home is great and original details are exactly what I love in a house. There's plenty of room for us and guests, lots of thoughtful updates, and the house seems to be in good shape overall. However, there's lots of room for changes, more modern and higher end updates while retaining the history, and tons of weekend project potential. Though I'm certainly looking to relax at the weekend cottage, I'd still like to have some projects to do that involve more than applying sunscreen. The only concern I might have is that it is still within the city and pretty close to neighbors, so it isn't a super private getaway place, but I'm not sure that really bothers me. And since we're not in the internal emotional struggle of giving up our home over this home, this is an easy yes for me. Now I need to go find a metal detector and start searching the beaches for buried treasure to pay for this home. Anyone have a good treasure map the could lend me?

Wendy: Even though I wish the home had a bit more privacy as well as fronted the water, I would definitely buy this home as a weekend/summer getaway. The location is great (it doesn't get more charming than St Michaels after all), I love the age and style of the home, and the yard and carriage house is so luxurious. As Alex said, this property seems to have just the right amount of projects that we could dig into, without feeling like we couldn't relax and enjoy the home. I'm already itching to start taking down some of that dated wallpaper. 

What do you think? Would this house fit your bill for a nice vacation home. Do you think you could relax and enjoy yourself in a place like this, or would you be interested in more open area, more privacy, and more beach? Obviously it all come's with a price, but hey, this game is all about forgetting about the price of the house.

If you'd like to see additional details, they are available on the home's full listing page.

Interested in reading about other interesting homes for sale? Want to offer your take on "would you trade"? Check out the Open Housing section of Old Town Home.

Photo Credits: Benson & Mangold Real Estate and listing agent, Sharon Woodruff where MRIS is noted.