With over two decades of top-producing success in the marketing, sale, and rental of unique and luxury properties, Jaclyn Picarillo has earned distinguished acclaim as the sought-after expert in Fairfield County’s high-end real estate landscape. Her unwavering commitment to exceed client expectations is reflected in a portfolio of record-breaking transactions and long-standing client relationships.

Jaclyn brings a warm, boutique approach to every client experience, blending creative, targeted marketing with deep industry connections and strategic negotiation techniques. She represents buyers, sellers, investors, landlords, and tenants across a diverse range of properties - from waterfront estates and new construction to land development opportunities, condominiums, antiques, million and multi-million dollar homes.

Known for her integrity, enthusiasm, and tireless work ethic, Jaclyn treats every transaction with the same care and precision as if it were her own. Her hallmark is white-glove service, complete discretion, and clear, continuous communication - delivering exceptional results with professionalism and grace.

A graduate of the University of Southern California’s Annenberg School for Communication (USC), with a minor in Theater, Jaclyn began her career in Los Angeles in entertainment PR, representing A-list talent and major studios. She later returned to the East Coast to join her late mother, Debra Gailhard, an award-winning Real Estate Agent and founder of Waterfront & Estate Properties, where she was mentored by one of the best in the business.

Today, Jaclyn leads Unique & Luxury Properties with a seasoned perspective shaped by market highs, lows, and everything in between. Her ability to navigate complex transactions and deliver successful outcomes has earned her a loyal clientele and industry-wide respect.

Jaclyn is an active member of the Mid-Fairfield County Board of REALTORS®, Smart MLS, Greenwich MLS, CT Association of REALTORS®, and the National Association of REALTORS®. She served on the Strategic Planning Committee for the Town of Fairfield and is on the Board of Directors for Near & Far Aid. Each Spring Jaclyn leads the Near & Far Aid Designer House Tour and facilitates Corporate Sponsorship. She is also a proud alumna of USC, Tri-Delta, and Fairfield High School, where she serves as Class of ’97 Alumni Liaison.

Outside of her career, Jaclyn is a devoted wife and mother of two incredible daughters and two beloved mini Bernedoodles. She is passionate about interior design, architecture, real estate development, gardening, boating and paddle boarding, healthy living, photography, music, and exploring the many amenities Fairfield County has to offer.