Top Agent Cindy Raney Talks All Things Fairfield County Real Estate

With over $375 million in sales and 17 years of experience, Cindy Raney has a wealth of advice and insight to share.
Top Agent Cindy Raney Talks Connecticut Real Estate And Shares Advice Sasco

Photograph by Julia D’Agostino

The Fairfield County real estate market has been booming for over a year and navigating these fast and luxurious waters requires finesse. Having an expert in your corner is crucial, whether you’re a buyer or seller. Cindy Raney, founder of Cindy Raney & Co., grew up in the picturesque area and specializes in Westport, Weston, Fairfield, Southport, Darien, Greenwich, and New Canaan real estate. She knows these markets inside and out, so now it’s time to get to know the powerhouse agent as well.

From what she’s learned most in her career to predictions for what’s next for the Fairfield County real estate market, Cindy is sharing all her expert insight here.

Top Agent Cindy Raney Talks Connecticut Real Estate And Shares Advice Hubbell Garden

165 Hubbell Lane, Fairfield | Photograph by CT Plans

Tell us a bit about your background. What drew you to a career in real estate?

I started my career in finance, working with one of the top private wealth teams in the U.S. Ultimately, I determined that I wanted more autonomy over what I did for a living. Leading one of the top real estate teams nationally is incredibly rewarding. Working with clients and helping them achieve their dreams of homeownership is as satisfying an end result as anything I can think of.

With over $375 million in sales and 17 years of experience, what is the biggest lesson you’ve learned in the Connecticut luxury real estate industry?

That you really need to be an expert in the luxury space. Meaning, you have to know each and every aspect of a home you’re representing. It goes much deeper than just talking about square footage, bedrooms, baths, etc. Can you talk about what distinguishes the Thassos marble in the master bath, or the high-end custom millwork details in the cabinetry, or the historical significance behind the estate? You need to convey the luxury and grandeur that the house requires.

The Fairfield County market is hotter than ever. What advice do you have for buyers and sellers who want to jump in?

The market is challenging. For the first time in 10+ years, Connecticut homes have finally appreciated in value. From 2008 through mid-year 2020, our state experienced the least home price appreciation in the entire U.S. So, to say we’re finally getting our due is an understatement.

As a seller, you are definitely in an advantageous position. The keys to selling your home are threefold: Price it properly, stage rooms where necessary, and select an agent/team that really understands your market. If you’re a buyer, we acknowledge that it is a very competitive market with demand far exceeding supply. It is critical that you work with an extremely experienced agent who can help you win during a bidding war the first time around. We have had several buyers come to us after losing out on multiple bidding wars. When we share our strategy with them, they consistently tell us that they wish they had reached out initially for our advice.

Top Agent Cindy Raney Talks Connecticut Real Estate And Shares Advice Laurel Garden

96 Laurel Brook Lane, Fairfield | Photograph by Borgatta

What is the Cindy Raney & Co. difference? How do you stand out as a real estate group in Fairfield County?

I feel our differences are multifold. Our market knowledge is exceptional. Similar to understanding a luxury property, we know our markets inside and out, from every new listing to every closed sale in our target price range. We have unparalleled contacts in the industry, from our relationships with other top agents both domestically and internationally, centers of influence like mortgage brokers and real estate attorneys, to our immense database of high-net-worth clients.

How this helps us stand out is simple: We help clients sell their homes for more money. We have a proven process that continues to get results. Today’s market relies on providing your seller with exposure to the greatest number of potential buyers. Beyond that, it’s imperative that we read our audience when it comes to multiple offer situations, something that has become commonplace in today’s environment. There is a delicate balance between when to work with each offer individually versus requesting the highest and best offers by a specific deadline. There is no one size fits all framework for sellers in this market. Case in point, in the past month we sold (4) high-end listings at an average of 11% over asking. Each closing required a different negotiating tactic. In a market where the industry average is getting a house sold “at asking,” we are delighted to bring our clients final offers that far exceed that average.

We are fortunate to be backed by the prestigious Coldwell Banker Global Luxury® program. It provides our team access to one of the industry’s most respected and dynamic regional, national, and global networks. Our clients truly appreciate this aspect of our business as it brings their property exposure to the most exclusive audience.

Top Agent Cindy Raney Talks Connecticut Real Estate And Shares Advice Sasco Outdoor

1121 Sasco Hill Road, Fairfield | Photograph by CT Plans

What is the most unique element of your marketing approach?

It’s in our desire to treat every client as though they are our only client. Everyone talks about service, but not everyone delivers on that promise. We make it a point to provide what we call an “exceptional experience.” We are inspired by the brands that represent the pinnacle of customer-centric business models. They’ve earned that incredible level of trust our team strives to attain with our clients every day. We believe so strongly in that tenet that we incorporated the phrase “Exceptional Experiences” into our company’s logo.

To provide that exceptional experience, we retain a boutique marketing agency to extend our clients unique features to their property listing. Alongside our partnership with Coldwell Banker Global Luxury®, our agency provides distinct advantages that no other team offers: An individual property website, a seller dashboard that tracks and measures daily site visits, activity, and user interaction. They also provide targeted social media campaigns that extend far beyond Fairfield County to attract the right kind of buyer for our listed properties. This process helps identify how well our strategy is working in reaching the proper audience. If necessary, it allows us to pivot on a dime if we feel we have a greater opportunity to achieve success for our clients.

Top Agent Cindy Raney Talks Connecticut Real Estate And Shares Advice Team

Photograph by Julia D’Agostino

Your team has an intimate knowledge of Westport, Weston, Fairfield, Southport, Darien, Greenwich, & New Canaan. What made you choose these towns as your niche and what do you love about them?

We selected these areas because we love the charm and character each possesses. As a state, Connecticut is comprised of a collection of unique towns, each alluring in its own way. While each differs from one another, each has so much to offer families or individuals of any age. We are fortunate to live in such a beautiful area.

Top Agent Cindy Raney Talks Connecticut Real Estate And Shares Advice Sasco Aerial

1121 Sasco Hill Road, Fairfield | Photograph by CT Plans

Can you tell us about a few exciting listings you have currently?

Right now, we are grateful to have a number of outstanding listings. Of these, two that jump out for us are 1121 Sasco Hill Road (Fairfield) and 96 Laurel Brook Lane (Fairfield). Both homes are exquisite in their own right. 1121 Sasco Hill sits atop one of the most prominent streets in all of Fairfield County, with water views, a sweeping lawn, and a magnificent estate designed by Cameron Clark. 96 Laurel Brook is its own private oasis set on 4.25 acres with a pool, tennis court, and a professionally manicured landscape that is second to none. At 8,000+ square feet, the Georgian Colonial is magnificent in its own right.

Top Agent Cindy Raney Talks Connecticut Real Estate And Shares Advice Laurel Exterior

96 Laurel Brook Lane, Fairfield | Photograph by Borgatta

Can you give us some expert insight on the current Fairfield County real estate market? What’s happening now and what do you predict next?

In the absence of a crystal ball, we feel that the strong real estate trends in Fairfield County will continue into 2022. As we see it, several things play into this viewpoint.

Firstly, the housing supply remains extremely low while there continues to be a surplus of buyers. It’s as simple as supply vs demand. Year to date, housing inventory in Connecticut is down 28% versus one year ago. Until inventory increases and or buyer demand subsides, the market will continue to be robust.

Secondly, part of what’s driving this residential housing boom is the improving economy and the fact that Millennials are reaching their prime homebuying years. Because they are the largest generation in American history, we believe demand will remain high for a period of time because they need houses!

Finally, we are not seeing an immediate need for people to return to their corporate office space. If anything during the pandemic, it was proven that people could be equally if not more productive and efficient working from home. That may well change over time, but for right now, a beautiful home in Fairfield County with lots of interior space, professionally landscaped property, great home office(s), a pool, and outdoor kitchen for family entertaining will continue to bring buyers to the area.

Top Agent Cindy Raney Talks Connecticut Real Estate And Shares Advice Fairfield

Sold in Fairfield | Photograph by CT Plans

When you’re not helping clients find their dream homes or achieve the best home sale possible, what do you enjoy doing in your free time?

My husband Jason and I are very fortunate to have five happy and healthy children. They range in age from 9 to 20 and keep us incredibly busy—all in amazingly positive ways. When we have a moment to step away from work, we love to play golf or tennis with the kids or taking a hike with our Sheepadoodle Penny through Brett Woods. Catching the sunset and relaxing at one of our area’s amazing beaches is also something we try to take advantage of.

We believe strongly in giving back to our community. For many years now, we have heavily invested our time in support of Yale New Haven Bridgeport Hospital. More specifically, the Norma Pfriem Breast Center, their Foundation Board, and Friends of Pediatrics. We are privileged to be associated with such a remarkable hospital organization. The work the doctors, nurses, and staff perform on a daily basis to make our lives safe and enjoyable constantly reminds us how fortunate we are to have them in our backyard.

Top Agent Cindy Raney Talks Connecticut Real Estate And Shares Advice Family

Photograph by Julia D’Agostino

Cindy Raney always has her finger on the pulse of Fairfield County, whether she’s unwinding with her family or creating custom marketing strategies for listings with her team. It’s her intimate knowledge of Connecticut’s unique towns and her team’s concierge-level service that keeps clients coming back for more and referring her time and time again.

Since the market can change in an instant, it pays to work with an expert like Cindy whether you’re a buyer or a seller. Visit to learn more and see how you can work with her leading real estate team.