
Rye Lifers is a MyRye.com series that introduces you to people that have spent their lives in Rye – people who have grown up in Rye, worked in Rye, come back to raise their family in Rye. Do you know someone we should profile for Rye Lifers? Tell us.
Today meet Sandy Chittenden.
Rye Lifer: Sandy Chittenden
MyRye.com: Why are you a Rye “Lifer”?
Chittenden: My name is Sandy Chittenden, and my family has called Rye home for three generations. It’s the best place on earth, and I’ve never truly lived anywhere else, with the exception of the first eight months of my marriage, also to a Rye-lifer. We rented an apartment in Harrison… but we were close enough to the border to see the City of Rye sign.
Tell us about the street in Rye you grew-up on.
Chittenden: I grew up on the Boston Post Road. My family home, which I still own with my sister, backs up to Walker Avenue. I had an incredibly happy childhood, my aunt and grandparents owned homes on Walker. Summertime was my favorite season. Spending time in my grandparents’ screened-in porch and swimming pool, simply the best. Those memories, that sense of closeness, will always be treasured. Sadly, my grandparents’ home was recently torn down, while my aunt and uncle still own their home.





Where in Rye do you live now?
Chittenden: Today I live with my husband Rob [Jake] Chittenden, also a Rye-lifer, in Rye Gardens on Beverly Drive. One of the main reasons we purchased this home in 2001 was because it also had a small inground pool. Our goal — which I believe we achieved — is recreating happy memories outside and around our pool.
Who was your favorite teacher at Rye High School and what year did you graduate?
Chittenden: I graduated from Rye High School in 1983. I enjoyed many of my teachers. The top three that left lasting impressions are Mr. Drago, Mr. Yedowitz and Mr. DeRufo. Mr. Drago was a coach and a gym teacher of mine. He was genuine and taught me many valuable life lessons that have stayed with me to this day, including tips in relaxing the body and mind, something similar to today’s meditation practices. Having teachers who truly care make Rye schools so amazing. It’s another reason my connection to Rye has always run so deep.







Where do you work in Rye and what do you do?
Chittenden: Since 1997 to present, I’ve been a real estate broker with Sotheby’s International Realty. Selling and finding “the one” for clients has been nothing short of the best privilege. I thoroughly love Rye, know almost every street, or someone on the block that lives there or used to own. Rye really sells itself. I’m just thrilled to welcome everyone into our amazing community.
What in your view are the two or three greatest Rye traditions—current or past?
Chittenden: My favorite traditions are the annual elementary day school fairs. Of course, Osborn was the best — my mom and her friend ran the best game of the day… the cake walk. Winning beautifully decorated homemade cakes, one in each hand walking home while my friends carried the winning goldfish for me were the fondest memories. Another tradition I adore is the annual Easter egg hunt down at Rye Rec. I hope this tradition continues, as we’d love to take our grandson. Halloween painting was also a top tradition that I loved.
What about the great Rye institutions—community organizations, shops, restaurants. Which ones are or have been part of the Rye fabric?
Chittenden: My favorite Rye institutions are Kelley Sea Level. We’ve been going there, and the Post Road Market (aka Jerry’s) for as long as I can remember. When I was a youngster, the Rye Smoke Shop was a favorite Rye institution. Many of my allowance funds were spent on a favorite magazine or a piece of candy. I also spent a fair amount of time with friends at Cosmo’s Pizzeria on Purchase Street and the Town and Country Deli!!
Thanks Sandy!

