Sandy Chittenden

Licensed Associate Real Estate Broker

Sandy Chittenden

Sandy Chittenden

Licensed Associate Real Estate Broker

Rye

49 Purchase Street
Rye, NY 10580

Stamford

3 Roxbury Road
Stamford, CT 06902
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Sandy Chittenden is a lifelong Rye resident with a heart for her community and a passion for helping people feel truly at home. Having raised two daughters here and been deeply involved in their schools, sports, and local activities, Sandy brings an authentic, insider’s perspective to every real estate transaction. Her clients don’t just benefit from her market knowledge—they gain a trusted partner who genuinely cares.

With more than 28 years of experience in the Westchester real estate market, Sandy has built a reputation for excellence, integrity, and personalized service...

Sandy Chittenden is a lifelong Rye resident with a heart for her community and a passion for helping people feel truly at home. Having raised two daughters here and been deeply involved in their schools, sports, and local activities, Sandy brings an authentic, insider’s perspective to every real estate transaction. Her clients don’t just benefit from her market knowledge—they gain a trusted partner who genuinely cares.

With more than 28 years of experience in the Westchester real estate market, Sandy has built a reputation for excellence, integrity, and personalized service. She is consistently ranked among the Top 100 agents companywide and has been named one of the Best Real Estate Agents in Westchester by Westchester Magazine for 2023, 2024, and 2025—a testament to the trust and loyalty she’s earned from clients and colleagues alike.

Whether buying or selling, Sandy works tirelessly to make the process smooth, stress-free, and even enjoyable. She’s a skilled negotiator with a down-to-earth approach, and she uses the latest technology and social media strategies to market homes to the widest audience possible. Her goal is simple: to build lasting relationships and ensure every client feels confident, supported, and happy with their outcome.

Outside of real estate, Sandy is a passionate advocate for her community, especially through her work with Soul Ryeders, a volunteer-driven nonprofit supporting individuals and families affected by cancer. Her journey with the organization began in 2012 when she donated her own wig to The Wig Exchange, a program that provides high-quality wigs to women facing hair loss. Deeply moved by the mission, Sandy became a longtime volunteer and now serves as a client coordinator, walking alongside women in some of their most vulnerable moments—offering support, encouragement, and a personal touch that mirrors the care she gives her real estate clients.

When she's not helping clients or volunteering, you’ll often find Sandy walking along Rye’s beautiful coastline or spending time with her family.

Sandy is proud to be a member of the National Association of Realtors, New York State Association of Realtors, Westchester Putnam Board of Realtors, and Rye-Harrison Multiple Listing Service.

Sandy Chittenden is a lifelong Rye resident with a heart for her community and a passion for helping people feel truly at home. Having raised two daughters here and been deeply involved in their schools, sports, and local activities, Sandy brings an authentic, insider’s perspective to every real estate transaction. Her clients don’t just benefit from her market knowledge—they gain a trusted partner who genuinely cares.

With more than 28 years of experience in the Westchester real estate market, Sandy has built a reputation for excellence, integrity, and personalized service. She is consistently ranked among the Top 100 agents companywide and has been named one of the Best Real Estate Agents in Westchester by Westchester Magazine for 2023, 2024, and 2025—a testament to the trust and loyalty she’s earned from clients and colleagues alike.

Whether buying or selling, Sandy works tirelessly to make the process smooth, stress-free, and even enjoyable. She’s a skilled negotiator with a down-to-earth approach, and she uses the latest technology and social media strategies to market homes to the widest audience possible. Her goal is simple: to build lasting relationships and ensure every client feels confident, supported, and happy with their outcome.

Outside of real estate, Sandy is a passionate advocate for her community, especially through her work with Soul Ryeders, a volunteer-driven nonprofit supporting individuals and families affected by cancer. Her journey with the organization began in 2012 when she donated her own wig to The Wig Exchange, a program that provides high-quality wigs to women facing hair loss. Deeply moved by the mission, Sandy became a longtime volunteer and now serves as a client coordinator, walking alongside women in some of their most vulnerable moments—offering support, encouragement, and a personal touch that mirrors the care she gives her real estate clients.

When she's not helping clients or volunteering, you’ll often find Sandy walking along Rye’s beautiful coastline or spending time with her family.

Sandy is proud to be a member of the National Association of Realtors, New York State Association of Realtors, Westchester Putnam Board of Realtors, and Rye-Harrison Multiple Listing Service.

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Testimonials

Sandy is incredible. She walks you through every step of the process and does not overlook anything. She is efficient, knows what to look for, and very honest and trustworthy. Not only does she guide you, but she also educates you to help you understand everything involved in purchasing and selling a home.

John and Carolann Ruggiero

Sandy is incredible. She walks you through every step of the process and does not overlook anything. She is efficient, knows what to look for, and very honest and trustworthy. Not only does she guide you, but she also educates you to help you understand everything involved in purchasing and selling a home.

John and Carolann Ruggiero

I would highly recommend Sandy Chittenden for the purchase or sale of your home. She is extremely knowledgeable, committed and patient. She takes the time to explain the process and assist when needed. Sandy has the rare ability to be both aggressive yet kind.

Donna; Javier Russo; Tandazo

Sandy’s local real estate knowledge and pragmatic and straight-forward approach enabled us to focus our search, expand our ideas on what is possible and most importantly to be patient. It also helped that Sandy’s knowledge of the Rye market, and experience of a broad range of homes in the Rye area provided us with the information we needed to make informed decisions. Sandy was very flexible with her time and was always available to provide answers and guide us. We strongly recommend Sandy to anyone looking to buy or sell a home in Rye.

Emanuel; Elizabeth Acosta; Aguirre-Acosta

Sandy Chittenden was an experienced guide who very successfully marketed and sold our home in Rye. Sandy is aware of market trends and conditions and tailors her 'to do' lists and strategies with specific intention to optimize buyer appeal. Sandy is honest, transparent, responsive, calm, supportive, and hands-on across the entire process. With a robust roster of potential buyers, we were able to realize our target price, with multiple offers, in a timely manner. Sandy exceeds expectations. Highly recommend.

Tara and Charles Matthews

Sandy was exceptional in handling my apartment rental. She went way beyond average service. She was wonderful in every way. I highly recommend her.

Linda and Robert Glew

I have known Sandy for over 50 years and she is a shining star. Whether buying or selling a property you will not find a more well-qualified broker. Sandy is an articulate, loyal, totally honest and immensely hard-working individual, who dedicates herself thoroughly to the task at hand and follows up on getting the job done promptly and efficiently. Not only did I entrust her with one property, I also gave her a second at the exact same time. Within less than a week both properties had accepted offers and through the closing period could not have been a smoother experience. She comes complete with an array of vendors to help in preparing a house for listing. This includes both required items like sewer inspections and any updating like painting or carpet. She really has access to anything needed and made great recommendations that only helped with the overall process. Sandy is the most knowledgeable broker I’ve seen and the complete package with answer to any questions. I would also add that I did everything with her while living on the West Coast which she handled effortlessly. If you need to hear first-hand of my overall experience have Sandy give you my contact information and I’ll be glad to elaborate.

Estate of Sheila Ruth Shevin

Sandy Chittenden's representation for the sale of our house was absolutely outstanding. She went above and beyond in every respect, got us a great price on our home, and could not have been more helpful in moving us through the process of the sale. I could not recommend her services more highly. Thank you so much!

Nancy D. Platt Irrev. Trust

Sandy was excellent!! Knowledgeable and helpful at every turn.

Emily and Matthew Bigony

Sandy is always thorough and professional !

Rosario Barone

very responsive , very friendly , such a pleasure !!!

Robin; Ralph Dibetta; Derosa

Sandy was so patient and understanding. It was very hard leaving our family home that we had lived in for thirty years. She really help us through a very tough time. Her knowledge and explaining things made it easier for all of us. She was always there to answer any questions! She is a gem

Jeffrey and Sue Little

Sandy is simply AMAZING! Sandy provided exceptional and professional service from start to finish. She was always accessible to answer my questions with her expertise, and she remained positive and encouraging despite coming across various seller-related obstacles/delays throughout the home buying process. By the time my closing day rolled around, Sandy felt more like family than my real estate agent. I can't even begin to thank Sandy enough for always going above and beyond to help me find my dream first home!

Ryan Marynowski

Great process Sandy was extremly helpful on all aspects of the transaciton.

Jennifer Mayer

Sandy was excellent all throughout the process of purchasing my first home. She guided me well, was very supportive and accommodating and was overall a pleasure to work with.

Brian Gates

We feel so lucky that Sandy was our agent for selling our house and for buying the co-op we now call our home. The only reason that we sold our house in only five days at a price higher than the price we first wanted, was that we trusted Sandy, and that we followed her advice. We truly believe that if we had not listened to Sandy about timing and pricing, that our house would have taken many weeks, and maybe even months, to sell, and at a lower price. We had a similar experience when Sandy helped us to buy the co-op where we live now. We were under pressure to find a particular size in a particular location, and when the ideal unit came on the market, we knew we had to grab it. Sandy knew exactly how to guide us so that we could snag the place quickly, and now we are very happily situated in our new home. Sandy is a real estate agent with a heart, and we know, in both our selling and our buying experience with her, that our interests were always Sandy's number one priority -- she always has had our best interests at heart. She knows the business, but even more importantly, she knows people, and it is truly lovely to work with her. If anyone were to ask our advice, we would say, "Listen to Sandy!"

Michael and Vivian Ward

I cannot say enough good things about working with Sandy. To say that Sandy is extremely talented would be an understatement. Sandy guided us through every step of the process from selling our home to buying our dream home. Throughout the process, Sandy shared her expertise and knowledge. She calmed our nerves and patiently walked us through the process which was overwhelming to us at times. Sandy was so generous with her time and always answered our questions. Sandy is an amazing person. She is kind, generous and an gifted realtor. Thank you Sandy for everything!!

Miriam Ward

Working with Sandy is a dream. She is incredibly knowledgeable about the Rye market. She is generous with her time, accommodating, professional, and truly a pleasure to work with!

47 Harding Drive LLC

Sandy has been our realtor for many years on several homes. She is very experienced agent and you can depend on her in any situation you may have a problem with. She is a true professional. Sincerely, Phyllis and Georges Lagast

Phyllis DiGeorge

Your organization is always professional and knowledgeable of the marketplace. Main reason for continuing to recommend Sotheby's is your Broker Sandy Chittenden in the Rye Office. Sandy has been our representative over the years in selling houses in Rye, White plains, and last week in Rye Brook. While we had our rental property in Rye Brook, we used Sandy exclusively in the rental of apartments. See is honest, hard working and reliable.

Philip Scibona

Local realtors with local knowledge

Alexandra M Powell

Sandy Chittenden has represented my family’s real estate interests in Rye city for more than twenty years. She continues to bring a level of professionalism and support that’s exemplary in the field. Together, she and my development company, construction company and real estate holding company, have traded in excess of 30 million dollars of purchases, sales and rentals with consistency and positivity. In an age where folks “jump” from one company to the next, sometimes for a nickel, Sandy has maintained a relationship with my family and my company that is second to none. Happy to refer Sandy and happy to continue to do business with Sotheby’s as long as Sandy as with your team. The Paganelli and P&I families.

351 Park Avenue LLC

Sandy Chittenden is AMAZING! She is very thorough and takes her time explaining everything. She is honest and not pushy. We have been her clients for years and she has been very consistent, transparent and very pleasant to deal with.

Sandra and Kayvan Keyhani

Sandy was the best agent I could Have worked with she was professional always on time always got back to me I’m very transparent great job

Kathryn Mulvey

I called Sandy Chittenden with the task to sell 2 properties and purchase our Forever Home. She made this easier then I could have ever imagined. Sandy is everything you want in a Real Estate Agent. Her professionalism, knowledge and availability made our whole experience the best. We are forever indebted to her!!!

Catherine and Michael Hansen

I called Sandy Chittenden with the mission to sell two properties and find the perfect house for my family. She made our experience so painless that we are forever in her debt. Her professionalism and knowledge made our sellings and purchase a breeze and a joy. She was always available for showings and answered all of our questions. She is a true professional and the best at what she does!

Catherine and Michael Hansen

As an out-of-state seller, we rested easy knowing Sandy was at the helm. Honestly, we could not have done this without her and are so grateful for her guidance, expertise and professionalism!

Mary Jane Ryan-Stamler Living Trust

Sandy was an absolute pleasure to work with. She was professional, knowledgeable, and sincere in her guidance of selling our house and searching for a new home. Our house sold faster than I could have imagined and I believe it was due to her marketing & pricing. While our new home search was during the challenging Covid times, she never gave up and went above and beyond to find our family’s forever home. We are truly grateful for Sandy’s work and partnership.

Deena and Todd Winchenbach

Sandy Chittenden from Julia B Fee/Sotheby's International Realty has served as my agent for my rental property in Rye twice now, and I can't imagine using anyone else. I no longer live near that property, so reliable, complete, and timely communication is especially crucial. Sandy is consistently responsive, quickly replying to any call, text, or email with a plan for moving forward. I alerted her that I'd need to list the house again, and she brought two service providers there that same day to get estimates for the needed repairs. She has established relationships with good painters, cleaners, plumbers, etc. Not only is she happy to make those referrals but she also lets them in, shows them what needs doing, and has even offered to negotiate price with them on my behalf. Then she makes frequent trips to the house to check on their progress and take pictures for me. Sandy has handled or advised me on every aspect of preparation, marketing, negotiation, and lease details. And she has even helped me handle sensitive issues around tenant turnover. She is positive and reassuring, and her advice has been spot-on. She knows the Rye (and surrounding area) real estate scene inside out. She understands and does a good job explaining the variables affecting pricing, timing, listing, and showing -- both for sales and for rentals. Her recent advice to me about expanding the scope of my prep work paid off. Within 2 hours of listing, new tenants were found -- because she knew just how to price the house and how best to showcase it. Especially important is that she understands the demographic of who's looking to rent and what's important to them. A pandemic adds layers of complexity to everything, including real estate. I usually travel to the property to inspect it and oversee repairs and upgrades myself. I told her I was hesitant to travel with restrictions still in place. Without skipping a beat, Sandy said, "I will be your eyes." She has been so generous with her time and efforts, and I'm hardly her only client. Compared to the luxury sales she also handles, my modest rental is small potatoes, yet she still treats me like I'm her top priority. Even more important is that she gets results, but her full-service support is unparalleled.

Laura; Robert Kranis; Lafon

Sandy was exceptional. She was attentive, knowledgable and dedicated. We could not have done it without her. She treated the sale of our home as if she were selling her own. I can't say enough about her professionalism and her extremely valuable advice.

John and Francesca Bellizzi

Sandy Chittenden is as professional as they come. Honest, prompt, thorough, smart, kind, and knows the market at every turn. I recommend Sandy to any buyer/seller looking for an agent who's integrity is without compromise. My business relationship for the past 10 +/- years with Sotheby's and Sandy's representation for ALL of those years, has been nothing short of stellar.

Roger Paganelli

Sandy is a great Real Estate agent, but most of all she is a good person with a lot of passion for what she does. We met Sandy at an open house and fell in love with her way of presenting the property and her suggestions, so we decided to engage her as our agent. At the time we met Sandy we had been living in Rye for almost ten years and were looking for a bigger home in town. We always appreciated her honesty: many times she would recommend not to see a given property if she knew there were problems, which was important to us given the little spare time we had. In the end, Sandy drove us around the city for almost a year before we decided to put an offer on a house. She provided us with insightful and accurate information about the neighborhood and the market that were essential to win the bidding war.Thanks to her superb negotiation skills we got a great price.

Rosanna and Alberto

Sandy Chittenden has represented me as both buyer and seller for more than 15 years. Together we have traded over 20 million dollars in real estate. Sandy is honest, hard working, knowledgable of her market and ALWAYS does the absolute best that she can for her client. If you know someone moving to or from Rye, don't hesitate, recommend Sandy and they won't be disappointed.

Roger
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My Listings

10 Stewart Place #2AW
White Plains, NY $449,000

10 Stewart Place #2AW

White Plains, NY

$449,000
  • 1 Beds
  • 2 Baths
  • 1,132 Sqft
11 Alden Road #6L
Larchmont, NY $490,000

11 Alden Road #6L

Larchmont, NY

$490,000
  • 3 Beds
  • 2 Baths
  • 1,400 Sqft
630 Forest Avenue
Rye, NY $3,495,000

630 Forest Avenue

Rye, NY

$3,495,000
  • 5 Beds
  • 4/1 Baths
  • 4,064 Sqft
116 North Street
Rye, NY $1,490,000

116 North Street

Rye, NY

$1,490,000
  • 5 Beds
  • 3/2 Baths
  • 2,260 Sqft

My Sales

115 Drake Smith Lane
Rye, NY $4,395,000
SOLD

115 Drake Smith Lane

Rye, NY

$4,395,000
  • 6 Beds
  • 6/2 Baths
  • 6,500 Sqft
390 Forest Avenue
Rye, NY $4,100,000
SOLD

390 Forest Avenue

Rye, NY

$4,100,000
  • 8 Beds
  • 6/2 Baths
  • 6,516 Sqft
14 Morris Court
Rye, NY $3,775,000
SOLD

14 Morris Court

Rye, NY

$3,775,000
  • 4 Beds
  • 4/2 Baths
  • 5,200 Sqft
22 Chamberlain Street
Rye, NY $3,755,000
SOLD

22 Chamberlain Street

Rye, NY

$3,755,000
  • 6 Beds
  • 5/1 Baths
  • 4,457 Sqft

Additional Communities

Click to view listings available

Additional Communities

Click to view listings available
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