A trip to Sherman, Connecticut, come fall in love!

Real Estate Agent with Berkshire Hathaway HomeServices New England Properties Licensed in Connecticut

Sherman ConnecticutSherman, CT is a small town located along the New York/Connecticut border, east of New Milford. I love going to Sherman just for the eye candy of it all! 

Sherman is located in the northern tip of Fairfield County, easy access through both New Fairfield and New York state make it a favorite place for New York City residents who are looking for that perfect Connecticut weekend getaway home. 

Sherman, CT is 22 square miles, with a current population of over 3,600 people. With all the charm and appeal of a small New England town, just as you would expect. With Candlewood Lake and Squantz Pond, the appeal for a waterfront or water community home is high. But the rest of Sherman is equally as lovely, and the town does have a beach open to all Sherman residents at Candlewood Lake. 

There are hiking trails for all levels of hikers. Naromi Land Trust maintains many of the trails and preserves in Sherman and they are beautiful! Today I drove to Wimisink Preserve on Route 39 North and wow, it is beautiful! I should have packed a lunch to eat while sitting on the observation deck overlooking the landscape. I can save that for another day, perhaps in the fall. 

My associate and I went to the trail head of the Appalachian Trail on Route 55. It was too hot to walk in there, I love taking short hikes on the Appalachian Trail. Today we met a man who left Louisiana in March and was planning to reach the end by the end of September. We dubbed him Bayou Boy. He was thrilled with his walk through New England so far, and was excited to be starting the trek though Connecticut. I wished I had asked to take a photo of him but the heat must have gotten to me. 

No trip to Sherman would be complete without a drive on Spring Lake Road, wow is all I ever say when I am there. From there we drove past the iconic Happy Acres Farm on Taber Road. The farm is beautiful and now they operate a farm stand there on Friday, Saturday and Sunday. And of course they have cows... and I do love cows! So it is always a treat for me to drive past there. 

The center is small and oh so New England small town. The Sherman Playhouse sits up on a hill overlooking the center, a very active playhouse and a bit of a surprise in the area. The Sherman Players put on some really fantastic theater, people rave about them! 

There is plenty more to see and do, a trip to American Pie to eat some of the best food ever should really be on your list if you do go to Sherman. But don't do what I do, please save room for dessert because boy do they have some great ones! I always eat too much of the food and have no place to put another bite. 

In a few short days I will be sharing a house I have for sale in Sherman. The owners are putting on the finishing touches so as soon as they are done I will be showcasing it. But what a house it is, a 4 bedroom colonial with the most amazing master bedroom suite, a lovely back yard, privacy and moments from The Club at River Oaks, hiking trails just up the road, Route 7 is right around the corner, Of course there is much more, and as soon as I take the photos it will be online. We are offering this lovely home on Evans Hill Rd for $465,000. 

Sherman, CT has been named "Best Small Town in Connecticut" three times by Connecticut Magazine, and I agree. Beautiful, convenient to the train station for a quick trip into the city, easy commute to Danbury and I84, minutes from downtown New Milford, and all manner of things to do! 

Please enjoy my short slide show of some of the sights in Sherman, Connecticut. 

 Search homes for sale, Sherman, CT

And stay tuned for my listing on Evans Hill Road in Sherman, any day now!


Posted by

Andrea Swiedler, Realtor, Southern Litchfield County Real Estate

2017 President, Greater New Milford Board of Realtors

2017 Connecticut Magazine 5 Star Realtor


 Search homes for sale in Litchfield County, CT.


Coldwell Banker Residential Brokerage

Litchfield County Regional Office,375 Danbury Rd, New Milford, CT 06776


© Andrea Swiedler 2009 - 2017

 Always do right. This will gratify some people and astonish the rest. - Mark Twain

Comments (5)

Lise Howe
Keller Williams Capital Properties - Washington, DC
Assoc. Broker in DC, MD, VA and attorney in DC

You make this part of Connecticut sound absolutely enchanting. I should take some time to enjoy CT rather than driving through it on our way to Boston! 

Aug 13, 2016 09:25 PM
Andrea Swiedler

Lisa, thank you! And yes, you should take the time to travel up Route 7 into Massachusetts to the Mass Pike rather than just fly through the middle of the state on Route 84. I am in the most beautiful part of the state, and the trip up Route 7 is totally amazing!

Aug 13, 2016 11:12 PM
Dorie Dillard Austin TX
Coldwell Banker Realty ~ 512.750.6899 - Austin, TX
NW Austin ~ Canyon Creek and Spicewood/Balcones

Good morning Andrea Swiedler ,

Love the video and post on your area! I can see why Sherman, CT is dubbed as the "Best Small Town in Connecticut" three times by Connecticut Magazine!"

Aug 13, 2016 10:06 PM
Andrea Swiedler

Dorie, I am blessed and never take for granted where I live! It is beautiful!

Aug 13, 2016 11:13 PM
Sheila Anderson
Referral Group Incorporated - East Brunswick, NJ
The Real Estate Whisperer Who Listens 732-715-1133

Good morning Andrea. Sounds a lot like my town in Stockbridge Massachusetts but different too. Glad you had a good day.

Aug 13, 2016 10:16 PM
Andrea Swiedler

Sheila, oh Stockbridge is beautiful too! I love the trip from here up Route 7 to Stockbridge. Sounds like a road trip needs to happen very, very soon. 

Aug 13, 2016 11:14 PM
Debbie Reynolds, C21 Platinum Properties
Platinum Properties- (931)771-9070 - Clarksville, TN
The Dedicated Clarksville TN Realtor-(931)320-6730

It is very inviting and makes me want to book a trip. I know you will get lots fo eyes on this post.

Aug 14, 2016 12:50 PM
Elyse Berman, PA
Best Connections Realty, Inc. - Boca Raton, FL
Boca Raton FL (561) 716-7824 CRS, ABR, GRI,ePR

Andrea Swiedler Sherman, CT looks like a wonderful place to call home.  Your post makes it so inviting!

Aug 14, 2016 09:32 PM

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