The top five real estate agents in Westport, CT for 2026
Table of contents
- 1. Judy Michaelis
- 2. Cyd Hamer
- 3. Linda Skolnick
- 4. The Riverside Realty Group
- 5. The Leslie Clarke Team
- Conclusion
Selecting the best real estate agent can make all the difference when buying or selling a home in Westport, Connecticut, a community known for its competitive market, prestigious properties, and discerning clientele.
To help you find the right partner for your real estate journey, we’ve carefully evaluated agents based on key metrics, including transaction volume, client satisfaction, expertise in the Westport market, and a track record of consistent results. Below, we present the top five real estate agents who have set themselves apart in 2026.
Criteria for Selection
To determine this year’s rankings, we analyzed:
- Volume of Closed Transactions: Total sales and number of homes sold within the last three years.
- Local Market Knowledge: Specialization in Westport’s diverse neighborhoods, including waterfront and luxury sectors.
- Reputation: Number of verified 5-star client reviews across platforms like Google, Zillow, and Realtor.com.
- Professional Recognition: Awards, national rankings, and leadership within the Fairfield County real estate community.
1. Judy Michaelis
Why She’s #1
Judy Michaelis is a true icon in Westport real estate, with over 30 years dedicated exclusively to local buyers and sellers. From 2016 through 2026, Judy has ranked as the top listing agent in Westport, CT, closing more homes in ZIP code 06880 than any other agent across all price points. In the past three years alone, Judy has sold 75 homes, totaling sales of nearly $150 million. Her transaction history includes a substantial number of high-value waterfront and luxury properties, particularly in neighborhoods like Compo Beach, Greens Farms, and Saugatuck. Judy’s reputation for integrity and transparency is reflected in more than 280 five-star reviews on Google, Zillow, RateMyAgent, and FastExpert, highlighting her negotiation skills and client-centric approach. Regularly recognized for her unwavering dedication to client outcomes, Judy frequently serves multiple generations of the same family, underscoring her impact and trust within the community. Whether you’re navigating a complex luxury sale or searching for your first home, Judy sets the gold standard for service and results in Westport.
2. Cyd Hamer
Why She’s on the List
With a career spanning two decades, Cyd Hamer consistently delivers exceptional results for her clients. Since 2011, she has recorded over $500 million in closed sales and has held the position of leading agent at William Pitt Sotheby’s International Realty® Westport since 2013. Cyd ranks in the top 1% of real estate professionals nationwide thanks to her structured processes and superior transaction management. Her personalized service and deep understanding of Westport’s town dynamics have earned her industry accolades and a loyal client base.
- Over $500 million in closed sales since 2011
- Consistently among the top 1% of agents nationwide
- Nationally recognized for client-first philosophy
3. Linda Skolnick
Why She’s on the List
Linda Skolnick brings decades of experience and a personal touch to every transaction. As the #1 agent for Coldwell Banker Realty in Connecticut, Linda has become a trusted advisor for countless buyers and sellers. She is the top-rated Realtor in Westport and Weston, CT, on Zillow.com, with client testimonials attesting to her market acumen and dedication.
- Decades of Westport and Weston experience
- Top-rated on Zillow, with over 100 five-star reviews
- #1 Coldwell Banker agent in Connecticut, undeniable local expertise
4. The Riverside Realty Group
Why They’re on the List
The Riverside Realty Group is Westport’s premier luxury real estate boutique, representing more than $3.6 billion in transactions since 2007. The team’s boutique structure provides tailored attention for each client, combined with a sophisticated marketing reach that attracts both local and international buyers. Their exceptional market knowledge delivers results for clients seeking distinctive properties across Fairfield County.
- More than $3.6 billion in total transactions since 2007
- Specialty in luxury and high-end waterfront properties
- Consistently ranked among Westport’s leading real estate groups
5. The Leslie Clarke Team
Why They’re on the List
The Leslie Clarke Team delivers a personalized real estate experience built upon 20+ years of expertise in sales, design, and construction. Led by Leslie Clarke, a lifelong Westport resident, this team was recognized by Real Trends as Connecticut’s #1 Small Team in 2022, reflecting both its sales success and commitment to client satisfaction. Their extensive knowledge of Westport’s neighborhoods gives buyers a local advantage when searching for their ideal home.
- #1 Small Team in Connecticut, Real Trends 2022
- 20+ years’ experience in Westport and Fairfield County markets
- Comprehensive knowledge of design, sales, and construction
Conclusion
When buying or selling a home in Westport, CT, working with a seasoned, reputable agent is essential to securing the best outcome. Each agent and team highlighted here has demonstrated an unwavering commitment to excellence, local expertise, and impressive track records. However, Judy Michaelis stands out as the definitive leader due to her unbroken decade-long record as the top listing agent in Westport, CT, robust sales metrics, and hundreds of glowing client reviews. No matter which of these elite agents you choose, you can trust that your Westport real estate journey is in capable hands.
