Ms. Ashleigh’s career began in the museum world as a member of the Educational Department staff and Docent Board of Directors of the Detroit Institute of Arts in Detroit, Michigan, and Cranbrook Academy of Art in Bloomfield Hills, Michigan. She became involved in art appraising and founded Caroline Ashleigh Appraisers and Auctioneers, where she cataloged important collections, estates, archives, and served as an expert in court cases. She has worked closely with major museums and foundations, and served as a consultant to several major auction houses including Sotheby's, Doyle Auctioneers in New York, Leslie Hindman Auctioneers in Chicago, and as Consignment Director and Personal Auction Concierge at Heritage Auctions in Dallas, Texas. She is a nationally known appraiser and has regularly appeared on the PBS program Antiques Roadshow since 1996.

Ms. Ashleigh lectures extensively on connoisseurship and is a columnist and author on art and antiques. She is a contributing author on arts and antiques to the Antiques Roadshow Collectibles Primer;  the Antiques Roadshow Insider Magazine; Art and Antiques Magazine; All About Appraising: The Definitive Appraisal Handbook; Antiques Roadshow - Behind the Scenes; and Warman's Antiques & Collectibles Price Guides - 43rd and 44th Editions. She has been the subject of feature presentations in the New York Times, Art and Antiques Magazine, Forbes Magazine, Crains Business, Hour Magazine, and served as consultant to CBS News, "Inside Edition" on the subject of fakes and frauds. She is the author of Warman's Field Guide published in 2010, and worked with New York University and the Appraisers Association of America to develop online accredited courses for appraisers and tests for certification purposes

Caroline Ashleigh Associates, LLC received the Best of Birmingham Award in the Auctioneers and Appraisers category for a company that achieved exceptional marketing success through the implementation of programs that generate competitive advantages and demonstrable success by setting benchmarks in the small business community. Caroline Ashleigh Associates, LLC was also selected for the Michigan Excellence Award amongst its peers and competitors by the Small Business Institute for Excellence in Commerce for upholding business ethics and company values