One of the fun parts of holding onto my real estate license is that when I’m bored and feel like daydreaming, I look at homes that I will never be able to afford.  Remember when you were young, you would drive by mansions and think “One day…”?  Well, those dreams have died- BUT I do dream about being able to pay my mortgage easily and having enough money to go out to eat some tacos.  Regardless, it’s nice to still dream and here are five of the most expensive properties currently on sale in Connecticut.

5.  $15,757,000 40 Aiken Road, Greenwich, CT 


This is odd.  Usually when you think “most expensive homes” you assume the list will have all Greenwich properties.  Not today.  The only Greenwich location is the one listed above which is listed for a little over $15 million.  It’s not even that impressive, the value comes because it’s 17 acres that can be subdivided into four lots… That means it’s viable for construction for four new homes.  That should sell easily sell in this desirable area.  For a home listed for over $15 million, someone needs to strip that tacky wall paper.  Kinda gross.  But apparently you can buy the lots separately… so there’s that- if you only have five million to spare.


4.  $19,500,000 26 Giles Hill Road, Redding, CT 


What a pretty house.  Classic gorgeous (well, in my opinion anyway)… Oddly, it has what they’re calling a “servants wing/apt”- which I guess is a politically incorrect way of saying where the staff lives.  I have to admit it though, that servants apartment is probably nicer than my regular home.


3.  $25,000,000 191 Ridgebury Road, Ridgefield, CT



I’m going to be honest- As a Realtor, I never understood why some people loved Contemporary style homes.  I get that they were big “in the 80’s” and have tons of modern flair- BUT, when it comes to your home, don’t you just want it to be cozy?  Apparently there’s a market for the unusual, because this Ridgefield home is available and asking a bazillion dollars.  I feel like the Jetsons should live here.


2.  $29,900,900 2 Quiet Lake Lane, Wilton, CT 


Comparing the fact that this place is *bargain* priced for a whopping $100,000 away from the most expensive home for sale currently in Connecticut, I’m a little disappointed.  It’s no where near as breathtaking as the next property- but it’s also a horse farm.  I guess I should also mention it’s 128 acres of prime real estate with the land spanning Wilton and New Canaan- Two of the wealthiest, most desired locations in CT.  So, if you’re into horses, having an EIGHT car garage, trout fishing in your own pond, and a HUGE pool… then maybe you’ll be happy to buy this place for just under $30 million.

1.  $30,000,000 188 Long Neck Point Road, Darien, CT



Are you kidding me?! This place has an indoor AND outdoor pool, a dock for your boat, right on the water, and LOOK at that bar! I will be dreaming about The Great Gatsby parties I would have here for weeks! Of course, almost a $120,000 a year in taxes is intimidating.  But then again, if I am rich enough to pay $30 MILLION for a place, what’s a hundred grand to Uncle Sam?




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