Cindy Searight's Profile Photo

Cindy Searight

Licensed Real Estate Salesperson | Licensed in CT

Social Media

Specialties

Listing Agent
Relocation Specialist
Equestrian Properties

Education

Syracuse University

Market Reports


Neighborhood Guides

A flag and flags on a pole

Westport

A harbor with boats docked and a row of houses

Fairfield & Southport

A river with a waterfall and a waterfall bridge

Weston

About Cindy
A Preferred Listing Agent Cindy creates an action plan to achieve her clients' dream sale price. She's a calm, organized "listing director", known for her keen marketing strategies, responsive communication style and notable work ethic from the initial pre-listing meeting through to closing day. Her comprehensive, responsible, hands-on approach gives home sellers peace of mind, knowing "Cindy's on it" and there for them, every step of the way. A strong negotiator, 100% of her listings have sold at or above their asking price.  

As ex-Creative Director of HGTV magazine, Cindy’s uniquely qualified to make a luxury listing “look like it belongs in a magazine” after years of experience directing the styling and photography of hundreds of home interiors and gardens, including the private residences of Fixer Upper's Chip & Joanna Gaines and Property Brothers Drew Scott. This professional level of staging elevates a listing to its “camera-ready best” to attract the maximum number of showings, a deep bench of offers, and ultimately the highest price the market will bear – all underscoring Cindy’s tremendous value as a luxury listing agent.  

Experienced with new home construction and renovations, Cindy is skilled advising buyers during the building process or brainstorming possible upgrades to an existing house. It’s in her DNA: her father, a real estate broker, partnered with an architect and custom builder. Visits to his construction sites and conversations over building plans ignited her early interest in home design, kicked off decades of experience and created a realtor who understands home construction from the foundation up.  

A certified relocation specialist, Cindy has helped buyer clients relocate from all over the country, often on a short timeline. As a CT native and former commuter to the city, Cindy’s market knowledge of each Fairfield County town's vibe and offerings provides a valuable resource for buyers seeking a specific lifestyle within a particular price band. She coaches clients on their strongest "power bid" strategy to be successful in this tight inventory market. Clients comment on Cindy’s dedication and protective nature as their fiduciary and real estate investment advisor. She has a strong track record of winning bidding wars based not only on market data, but also her gut instinct for a home's “it factor” and the level of passion that can create among the buyer pool.   

An equestrian and former Yale Club Polo player, Cindy can offer insights and expertise to those selling or buying horse properties in CT or beyond. As a member of EQ, Compass's vetted equestrian-focused realtor division, she's connected with a national network of knowledgeable agents serving the real estate needs of the horse community, coast-to-coast.  

A licensed CT realtor at age 19, Cindy worked part-time in her father’s real estate brokerage until graduating from Syracuse University and heading to New York, where she spent 25+ years as a Creative Director at Condé Nast and Hearst during the heyday of magazine publishing. Her experience, polished professionalism, marketing prowess, negotiation skills and focused work ethic have fueled her success in real estate – giving her clients a distinct advantage when selling their home and/or buying a new one.  

"I believe that the right house at the right time in our lives makes ALL the difference in our happiness. To be able to drive that change for my clients is incredibly rewarding work. I love seeing them move FORWARD in life!"  – Cindy Searight

Client Testimonials

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★★★★★
"We bought a condo townhouse in 2025 in Fairfield, CT. Cindy was the best! We met her initially at an open house and we were very impressed by her commitment and follow through on all aspects of the buying process. She listened to us and found us a house we love! She actively goes above and beyond to take care of her clients and we could not recommend her enough!" - Tess & Chris - Fairfield, CT

★★★★★
"As first-time home buyers, we honestly couldn’t have asked for a better realtor than Cindy. She was incredibly patient and quick to schedule showings, making the process so much more efficient. Cindy really understood what we were looking for and didn’t hesitate to move on when something wasn’t the right fit. Her background in design helped us visualize each space, which was such a bonus. What really stood out was her knowledge in the mechanics of a home. She could explain everything from boilers and A/C units to septic systems and water heaters, which was priceless for us. She also guided us through pricing and the bidding process with honesty and confidence. Above all, Cindy was our biggest advocate, walking us through every step with patience, diligence, and care. We’re so grateful for her support and would recommend her to anyone" - David - Ridgefield, CT

★★★★★
"Looking for a Listing Agent to help you navigate the real estate market? Look no further than Cindy Searight. She’s a dynamo! We’d interviewed a few other agents, one of whom was the local go-to, almost as a default. And while that might’ve been a solid choice, we decided to do something different. When first speaking with Cindy, she presented herself as articulate, assertive, and confident. Her prior employment at both HGTV as a Creative Director and her publishing work with Condè Nast exuded an interesting vibe that we thought would serve us well. And indeed it did! From the get-go, Cindy rolled up her sleeves doing an outstanding job staging our house and pool deck with props, furniture and art work. When our oak kitchen table needed updating Cindy painted it white. Our dingy shower floor? Cindy’s formula of industrial vinegar and baking soda brought it back to life. Maybe our older roof would need replacing? Cindy got three contractors in to quote the job. These are just a few of the many examples of Cindy’s above-and-beyond house preparation efforts. And as far as pricing our house to sell and overseeing all the attendant marketing, Cindy is an absolute pro. Cindy always made time for the many open houses she hosted which were great in that she knew how to point out all the positives of our house, unlike a buyer’s agent who is seeing the house with their client for the first time. She helped us navigate all the ins and outs of negotiating with our potential buyer. Our particular transaction had its share of complexities, but with Cindy’s management, all went well – we sold our house for the full asking price without any repairs or buyer credits. Cindy is a pleasure to work with and has a charming sense of humor which often came in handy. So really, if you’re looking for a CT Listing Agent, look no further than Cindy Searight. You’ll be happy you did!" - Martin and Stacey - Easton, CT

★★★★★
"Cindy did an excellent, professional job as a listing agent. This was not a primary residence for me, I live out-of-state, so we worked remotely, with Cindy on-site. I felt comfortable entrusting her with all preparation and staging. She oversaw numerous repairs including a handyman, boiler repairman, cleaners, gardeners, lawn care, and pest control. She suggested a priority list of repairs and improvements, including new lighting, paint color palete design, and staging plan. Cindy secured both an above-market bid, and a solid "over-asking price" backup offer, which she kept warm throughout the process, just in case. At the end of it all, we had a no-surprises closing and smooth distribution of funds and paperwork. I am pleased to unreservedly recommend Cindy to you." - Lance - Black Rock, CT

★★★★★
"Working with Cindy to find a house was extremely comforting during what can be such a stressful life event. She is so conscienious of researching all the public record facts on a property and suggesting any potential testing of any missing information (that could be detrimental in years to come). Her personal knowledge of home construction and mechanicals are an immense addition to her tireless work ethic in finding or selling houses for her clients. We highly recommend Cindy!" - Jim and Joan - Newtown, CT

★★★★★
"Cindy is a great resource and real estate agent. I highly recommended her! My experience with with Cindy on a relocation to the Stamford area was outstanding. She's very organized, responsive and thoughtful. I would be happy to work with her again in the future." - Nicholas - Stamford, CT


Cindy Searight’s Listings

$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
$1,999,000 | 218 Lower Farm Road, Fairfield, CT 06824
1/40
Listed By CompassUnder Contract

$1,999,000

4
Bedrooms
4,152
Square Feet
0.33
Acres
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
$1,499,000 | 8 Iris Lane, Westport, CT 06880
1/38
Listed By Compass

$1,499,000

4
Bedrooms
2,959
Square Feet
0.72
Acres
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
$299,000 | 3250 Fairfield Avenue, Unit 302, Bridgeport, CT 06605
1/27
Listed By CompassUnder Contract - Continue To Show

$299,000

2
Bedrooms
1,145
Square Feet

Cindy Searight’s Transactions

Past Sales
a front view of a house with a yard

$1,880,000

5
Bedrooms
3,900
Square Feet
0.26
Acres
$1,627,100 | 181 Margemere Drive, Fairfield, CT 06824

$1,627,100

4
Bedrooms
4,046
Square Feet
0.78
Acres
a view of a house with a swimming pool

$1,600,000

5
Bedrooms
3,188
Square Feet
2.82
Acres
a view of a lake with houses in the background

$1,535,200

4
Bedrooms
2,742
Square Feet
1.63
Acres
a front view of house with yard and green space

$1,426,000

4
Bedrooms
2,732
Square Feet
2.78
Acres
a front view of a house with a garden

$1,300,000

4
Bedrooms
2,041
Square Feet
0.28
Acres
a view of a yard with an outdoor space

$1,250,000

3
Bedrooms
2,366
Square Feet
5.2
Acres
front view of a house with a yard

$1,249,000

4
Bedrooms
2,746
Square Feet
1.47
Acres
$1,150,000 | 21 Orchard Hill Drive, Fairfield, CT 06824

$1,150,000

4
Bedrooms
2,727
Square Feet
0.22
Acres
$1,150,000 | 51 Stoneleigh Road, Fairfield, CT 06825

$1,150,000

4
Bedrooms
3,174
Square Feet
0.42
Acres
a view of a house with a yard

$1,150,000

3
Bedrooms
2,310
Square Feet
0.41
Acres
a front view of a house with a yard and large trees

$1,110,000

3
Bedrooms
1,724
Square Feet
0.41
Acres
$1,006,500 | 90 Harvey Road, Ridgefield, CT 06877

$1,006,500

4
Bedrooms
2,055
Square Feet
1.01
Acres
an aerial view of a house

$975,000

4
Bedrooms
2,868
Square Feet
4.61
Acres
$907,800 | 20 Maymont Lane, Trumbull, CT 06611

$907,800

5
Bedrooms
4,494
Square Feet
1.04
Acres
a front view of a house with garden

$900,000

3
Bedrooms
2,300
Square Feet
a front view of a house with garden

$775,000

3
Bedrooms
2,800
Square Feet
0.5
Acres
a view of a house with backyard and garden

$681,000

3
Bedrooms
2,794
Square Feet
1.6
Acres
Past Rentals
a view of a house with a yard

$3,950

2
Bedrooms
1,212
Square Feet
0.11
Acres
a view of a building with a street

$2,700

1
Bedrooms
800
Square Feet