Libby McKinney Tritschler, Executive Vice President of Sales and founder of the "On The Harbor" real estate team at William Raveis Real Estate, places great emphasis on local connection in her work with clients. The 65-year-old agent brings over 20 years of experience to the company and is considered an expert in the Southport, Fairfield, and Westport markets in Connecticut, where she has completed transactions worth over $800 million.
Raised in Fairfield County, McKinney Tritschler is involved in numerous local initiatives. These include her memberships on the boards of the Pequot Library, the Westport/Weston YMCA, and the Shepherds Mentors Programme. As part of a series on real estate agents, McKinney Tritschler recently provided insights into her work and career.
When asked about the most significant transactions of her career, McKinney Tritschler cited two examples. The first was the sale of a 7-acre parcel at 66 Beachside Avenue on Long Island Sound for $16 million. This property had been in family ownership since the mid-19th century and was the last remaining piece of her family's waterfront land, once part of the Bedford estates. She described the sale as a very emotional matter, due to the deep family history associated with the estate.
The second outstanding transaction was the sale of 260 Willow Street in early 2026 for $12 million, where she represented both the seller and the buyer. The seller had moved to Italy, and McKinney Tritschler felt honoured to have been entrusted with overseeing the entire process on-site – from preparing and managing the property to marketing and closing the sale. She described this as an extraordinary responsibility, of which she is very proud.
Her "Mount Everest" in her career, according to McKinney Tritschler, is not primarily tied to figures, although she pursues ambitious financial goals and aims to improve annually. Her highest goal is to know at the end of her career that she has become a reliable part of her community. She wishes that generations of families would ask her for advice, knowing that she will look after them. Building an exceptional business that simultaneously achieves this kind of impact would be the ultimate measure of success for her.
When she entered the real estate industry, she wanted to do her best. She consciously decided to join Al Filippone Associates at William Raveis because Al Filippone was one of the best in the industry, and she wanted to learn from the best. She observed, listened, learned, and developed her own approach from these experiences.
In the realm of architecture and design, while she admires many well-known personalities, she is more drawn to a beautifully executed home than to a specific name. Great design is specific to the particular house; it depends on the location, the architecture of the building, its surroundings, the budget, and above all, the lifestyle of its inhabitants. She appreciates it when a designer respects the integrity of a house rather than imposing a particular look on it. For her, the best design feels appropriate to its environment, is timeless rather than trendy, yet still very personal to the people living there.
