Top Real Estate Agents in Weston, CT for 2026: Who’s Leading the Market?

Introduction

In the competitive landscape of Weston, Connecticut, selecting the right real estate agent can make all the difference between a seamless transaction and a stressful selling or buying experience. Real estate transactions—whether purchasing a new home or selling a cherished property—are among life’s most significant financial decisions, so having a skilled professional in your corner is a critical advantage. Whether you’re looking to buy your dream home or maximize profits on a sale, partnering with top-performing real estate agents in Weston, CT, ensures you have expert representation and the best outcomes. Experienced local agents offer guidance through the intricacies of securing financing, navigating legal paperwork, and managing negotiations with potential buyers or sellers, providing invaluable support every step of the way.

As the real estate market in Weston continues to evolve, buyers and sellers encounter fluctuating home values, varying inventory levels, and shifting buyer demands. In 2026, Weston remains a sought-after suburb for its blend of luxury properties, excellent schools, and tranquil scenery, making the choice of a skilled agent more crucial than ever. High-quality communities, combined with the abundance of recreational spaces and proximity to New York City, make Weston a perennial favorite for both commuters and those seeking a peaceful retreat. The local real estate scene is fast-paced and requires agents who are adaptable, informed, and proactive to stay ahead of trends, anticipate market shifts, and advocate effectively for their clients.

Criteria for Evaluating Real Estate Agents

Finding the right agent involves evaluating several key factors that can significantly impact your real estate journey. Not all agents bring the same level of commitment, resources, or expertise to the table, so it’s essential to look deeper than just sales numbers or friendly recommendations. Focus on an agent’s specialization, ongoing education, and community involvement.

• Experience and Tenure:Agents with years in the field bring valuable insights and established negotiation tactics. They have witnessed market cycles, learned from a range of transactions, and know how to handle unique or challenging situations with finesse.
• Successful Transactions:The best agents demonstrate a proven history of sales and satisfied clients over the past year. A consistent record of completed sales in your specific price bracket signals their ability to deliver results under current market conditions.
• Client Satisfaction:Positive reviews and strong testimonials indicate consistently excellent service levels and a positive rapport. Consider also the agent’s communication style and their willingness to educate you about the process so you always feel informed and empowered.
• Local Market Knowledge:Deep familiarity with the Weston community and its micro-markets enables agents to accurately price, market, and sell homes. They can provide insightful information on pricing, the market, and accurately selling homes, as well as community developments, ensuring you make well-informed decisions.

Top Real Estate Agents in Weston, CT for 2026

Judy Michaelis

With over 31 years in the industry, Judy Michaelis stands out as one of the preeminent agents in Weston. Over the past year alone, she completed more than 30 sales, achieving a total sales volume of $715.5 million. Her deep experience and local reputation underscore her impressive record. Judy’s properties range from $1.2 million to $8.8 million, and she consistently negotiates an average of 26% off the list price, giving her clients an enviable edge. Known for her hands-on approach and accessibility, Judy is praised for her market intuition and her commitment to client success, whether guiding a first-time homebuyer or securing competitive offers for luxury estates. Her personalized strategies and exceptional work ethic have established her as a standout within Weston’s exclusive real estate circle.

Debbie Rehr

With 19 years of focused expertise in the Weston market, Debbie Rehr is recognized for her client-first approach. Last year, she closed on more than $113 million in sales, with transactions mostly between $800,000 and $3.2 million. Debbie is a skilled negotiator, achieving an average of 6% off the list price, making her a trusted partner for both buyers and sellers. Her dedication to each client and deep understanding of Weston’s neighborhoods allow her to tailor marketing strategies and home searches to fit individual needs. Debbie’s approach is rooted in transparent communication and attention to detail, ensuring that her clients have the information they need to make informed decisions from the initial consultation through to the final closing.

Christine Oleynick

Christine Oleynick, with a decade of local real estate experience, completed 19+ sales valued at $90 million last year. She specializes in homes priced from $850,000 to $3.4 million and boasts a strong negotiation record, averaging 9% off the list price. Christine is highly regarded for her market acumen and attentive client service. Her reputation is built on trust, proactive communication, and meticulous management. Christine’s clients appreciate her patience, ability to listen, and talent for matching buyers with the perfect property or positioning a listing area’s best properties to attract the area’s most qualified buyers. Her strong network within Weston keeps her clients informed about the latest listings and opportunities before they hit the broader market.

Linda Skolnick

With a career spanning over three decades, Linda Skolnick remains among Weston’s top agents. In the past 12 months, she notched 27+ sales totaling $744.2 million. LiOvera specializes in the luxury segment, handling properties from $1.5 million up to an impressive $16.5 million, and regularly negotiates an average 5% discount from the list price. Her steady presence in the community, paired with cutting-edge marketing techniques and savvy pricing strategies, ensures her listings receive significant attention and strong results. Linda takes pride in serving a repeat and referral-based clientele, reflecting her long-standing relationships and consistent delivery of high-value service to Weston residents.

Market Trends in Weston, CT

As of July 2025, the median sale price for a home in Weston dropped to $1.9 million, reflecting a 7.5% decrease from the previous year, according to recent data from Redfin. The reduction points to an evolving local market landscape where buyer patience and strategic pricing become even more important. Sellers must now evaluate their expectations, adjust timelines, and be flexible when considering offers to remain competitive in a market with fewer immediate buyers.

Despite this softening in Weston’s median, Weston’s luxury segment continues to outperform—fueled by limited inventory and sustained demand for exquisitely prepared homes. High-end buyers continue to be drawn to the town’s privacy, natural beauty, and architectural diversity. Sellers in this space see success by enhancing property presentation and setting realistic price expectations, according to local market updates. Upscale properties with modern amenities, thoughtful upgrades, and professional staging create strong interest and, in many cases, attract multiple offers. As a result, the market for luxury homes has proven resilient, consistently drawing in well-qualified buyers even as overall sales volumes fluctuate.

Tips for Choosing the Right Real Estate Agent

• Assess Experience:Partner with agents who have a proven track record of handling transactions similar to yours in terms of price range and style. A track record in your market segment ensures your agent is familiar with the hurdles and strategies specific to your situation, whether that means navigating multiple offers, understanding complex financing, or handling high-stakes negotiations.
• Verify Client Reviews:Check independent reviews and testimonials to gauge consistency and responsiveness. Explore online platforms and ask agents for direct referrals to verify their firsthand experience. Clients’ stories can offer valuable insight into an agent’s communication skills, availability, and commitment to resolving challenges effectively.
• Evaluate Local Insights:Ensure your agent is familiar with the neighborhoods, schools, and upcoming developments. Local knowledge is a considerable asset, as it enables agents to recommend the best locations, anticipate trends, and leverage connections with other professionals, such as inspectors, mortgage brokers, and contractors, to serve their clients better.
• Focus on Negotiation:Top agents protect your interests through skilled negotiation, saving you money and avoiding pitfalls. Strong negotiators use research, persistence, and market knowledge to ensure their clients receive the best possible deal. Understanding contract contingencies, inspection results, and closing timelines is a hallmark of elite agents who consistently act in their clients’ best interests throughout every phase of the transaction.

In Weston’s ever-changing real estate market, partnering with a skilled agent is essential for reaching your goals, whether you’re buying or selling. With fluctuating interest rates, shifting buyer expectations, and rising competition, having an experienced professional by your side is more important than ever. The agents featured above bring the local knowledge, negotiation expertise, and market insight needed to succeed in 2026’s evolving landscape. Be sure to conduct thorough research, interview potential candidates, and select a trusted professional who shares your vision and values. Choosing the right agent will help you navigate market changes with confidence, minimize stress, and achieve exceptional results.