Caroline Shepherd

Associate Real Estate Broker

Photo of Caroline Shepherd

Caroline Shepherd
Associate Real Estate Broker

At a glance

My Communities
Pound Ridge, Somers, South Salem, Waccabuc, North Salem, Mount Kisco, Bedford, Katonah, Lewisboro, Armonk

Accredited Staging Professional from AHS&D

About me

Caroline has decades of Real Estate Experience. Throughout the years her achievements include her rank in New York's Top Ten as well as receiving the Westchester County Board of Realtors Diamond Award for Excellence.  A consistent top producer, receiving Silver, Gold and Platinum awards in sales.  Caroline is also a winner of the Westchester Magazine Five Star Agent award. Caroline is licensed in NY and in Connecticut, serving the Fairfield County communities of Ridgefield, Redding, Wilton, Westport and Weston.  Most recently, Caroline officiated as the Global Luxury Director for Coldwell Banker NRT Westchester and Connecticut, sharpening her management and marketing skills in the luxury segment of the market.  Currently, she is back to doing what she enjoys most: assisting buyers and sellers in skillfully navigating the buying and selling process from start to finish. Caroline's objectives are clear; to listen in a caring way to her... More

Professional Associations & Designations

Hudson Gateway Association of Realtors, Professional Standard and Grievance Committee, Founder of the Women's Business Connect Networking Group, National Association of Realtors Member, New York State Association of Realtors Member and Hudson Gateway Association of Realtors, Member OneKey Multiple Listing Service.  

Community Involvement

Member of the Friend’s Committee for Hopes Door and Co-Chair for their 2015 Gala. Co-Chair for the Outreach Commission (Local Non-Profit Organizations) of St. Matthews Church in Bedford. Former Mentor for a child at Abbott House. Volunteer for Pound Ridge's Neighbor to Neighbor.

Real Estate Expertise

Caroline listens to her client’s needs, utilizing sound planning, professional ethics, strong communication skills and a solid company support system that helps her maintain a high standard of service. 


Caroline brought an extraordinary level of dedication, passion, expertise and professionalism to our sale. She fully appreciated the natural beauty of our unique lakefront property and its history to our family. Her thorough research and analysis of the property included excellent referrals who helped us to realize it’s full potential and ultimately decide to sell. Throughout the process she remained sensitive and responsive to our concerns. Caroline has sharp analytic skills in pricing and market timing. Her astute marketing strategy and negotiating skills led to a quick sale at a high price while maintaining the property’s integrity. Caroline is truly exceptional and a pleasure to work with, I would highly recommend her.

Janine G.

Caroline was nothing but lovely. She cares and cared. She went above and beyond making sure our house was marketed well, looked its best, and even landed us an unexpected, separate, and paid photo shoot! No matter what we needed, from open houses to hand holding, Caroline happily made herself available. Her love and knowledge of the area were felt, impressive, and reassuring. Selling our awesome, albeit unicorn of an estate, was no small feat and Caroline accomplished with grace what she and we set out to do.

marnie169 - December 5, 2022

We were so fortunate to have had Caroline handle the sale of our home in Bedford. Right from the start, her expertise and professionalism were focused on ensuring that our home was kept in the forefront of buyer’s minds. She tirelessly featured and promoted our home and we credit her dedication  to its successful sale. Caroline was proactive and responsive from day one and the energy and focus she impressed us with at the start never wavered. Even after we found our buyer, Caroline continued to guide us through the process right up until the day of closing to make it as seamless as possible. She pushed the process forward, keeping us informed, making referrals and navigating us through the inevitable hiccups that come with selling a home. We could not have been in better hands. She is a true gem!



Caroline is the person you want to work with whether you are buying or selling a home. We worked with Caroline for the good part of a year before she/we found the right home. Caroline immediately impressed us with her interest in getting to know and understand who we are as people so that she can successfully begin the search for a new home. She understood almost immediately what we are looking for in terms of what we need, want, what our style and architectural preferences are, the types of neighborhoods we would be inclined to be attracted to, stayed within our price range, and guided us through any and every twist or turn throughout the entire process. She never ever exhibited the slightest sense of being pushy regarding considering a property to purchase. Caroline always answered any and every question we addressed her with both quickly and knowledgeably. Her patience is bottomless and handles anxious buyers with calm and clarity. She's also a great resource for recommendations regarding trades people. She knows the area, she knows the people who work and live in our area, and recommends services solely from her own personal experiences. My wife and I think of Caroline as a friend, not only a great real estate professional, and are so fortunate that we, just by luck, found her to work with. We could not be more enthusiastic about recommending Caroline for anyone's real estate needs.  

Orin and Laura

Caroline listed and sold our home providing us with truly professional representation. She listened to our needs and proved that she could think outside the box, offering a modern approach to marketing while navigating challenging situations. Caroline sets herself apart and well above the bar. I have no hesitation in recommending her as a broker who will deliver the best results possible. 

Harry and Debra

I had the pleasure of working on with Caroline on the sale of my house in Katonah.  She was always there to answer my questions and was extremely knowledgeable and professional. 

The results end up speaking for themselves - She was able to get me two full-price offers within the first week the house was on the market and we proceeded through to closing without a hitch.

I recommend her absolutely without reservation.


I was fortunate to meet Caroline when I first moved to Bedford as a newlywed nearly 20 years ago, and I have relied on her generously caring, and impeccably professional guidance through a range of real estate decisions that have been vital to my family ever since. From our first transaction, in  which she served as both buyer & seller to execute our move within the same sweet neighborhood, to navigating into separate houses post-divorce, Caroline has proven herself a trustworthy counselor through every consideration. Beyond her astute business acumen and market savvy, she knows her region intimately -- and personally. Contractors, schools, financial details, town regulations and county-wide trends are all familiar territory for Caroline, and I simply don't make any real estate "move" (literal or otherwise) without her sage advice. Her personal attention is unmatched!


We are SO lucky to have found Caroline at the start of our home search! She was professional, warm and incredibly knowledgeable. Caroline is someone who I will HIGHLY recommend to anyone who is looking for a home in Westchester. She is a real gem and a once in a life-time agent that makes you feel immediately at ease and most of all, helped us to secure the home of our dreams.  Kate and Niels

I've known Caroline for many years after she helped my sister and brother-in-law sell their house. It sold for above asking price. I was not so lucky but I could not have found a more compassionate and consummate professional to assist me through a very difficult situation.  After the real estate crisis of 2008 my wife and I found ourselves in serious trouble. Our house had lost close to a third of its value and we were underwater on the mortgage. After the first sales contract fell through, and after working through the short sale process, we finally succeeded with Caroline's tireless assistance to liquidate the home. I cannot say enough about her professionalism and compassion in a very trying situation. Whether buying or selling I would not hesitate to recommend this truly wonderful person. Yes, I lost my house, which in many ways was very sad, but I gained a friend.


Caroline Shepherd is a true real estate professional but even more importantly for us she was a real partner in selling our home. Nothing was ever a problem; Caroline always had a solution and handled everything with a rare combination of efficiency and grace. In today’s challenging market, Caroline’s hard work generated not one but several qualified buyers which allowed us to sell at our asking price.  It is truly important to trust a full-time dedicated professional like Caroline who can navigate not only a brutal real estate market but also work through negotiations and follow up on the endless details that make or break a deal. Not only do we appreciate everything Caroline did in representing our home but we really appreciated working with her every step of the way. We recommend her without any reservation.


Caroline did a fantastic job selling our home. We live in Hong Kong and wanted to move it quickly and Caroline delivered in spades. She went above and beyond the typical agent services as she had to step in for us on a whole host of things that would normally be done by the local homeowners.  Such as moving and storing boxes for us, getting many estimates completed and repairs implemented in a timely manner. Caroline is very professional and an extremely competent broker. We highly recommend her.