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Lindsay Holland

Lindsay brings a wealth of diverse experiences, a passion for helping others, and a commitment to finding the perfect home for her clients.

Lindsay Holland

About Lindsay

Lindsay is a dependable and genuine professional, recognized for her relaxed yet resolute approach and her sincere rapport with her clients. A New Canaan High and Boston College alumni, her career in sales began in media sales planning and buying at Cossette Post, a boutique advertising agency located in New York City.


After dedicating 15 years to raising her five children and engaging in various educational roles, including being a 4's teacher at St. Marks Pre School and a Teaching Assistant at East School in New Canaan, Lindsay decided to embark on a new journey in real estate. Her decision was fueled by personal experiences of moving her own family multiple times and her passion for exploring houses, different towns, and innovative designs that mark significant chapters in people's lives. 


Lindsay has deep roots and strong ties in Fairfield County. She grew up in New Canaan and lived in Fairfield for 15 years in the University and Greenfield Hill areas, experiencing the vibrant community firsthand.  Lindsay moved back to New Canaan where both she and her husband grew up, to be closer to her family. She now considers both Fairfield and New Canaan as her homes. Her children attended schools in both towns and are actively involved in youth sports, immersing themselves in the local community and have grown to love the community they now call home. 


Known for her problem-solving abilities, friendliness, optimism, and ability to find the silver lining in any situation, Lindsay is highly regarded by both clients and colleagues. Lindsay's business approach is characterized by independence, goal-oriented focus, and discipline, which are complemented by her reputation for loyalty and kindness.  As a real estate professional, Lindsay finds immense satisfaction in helping individuals and families find their next chapter, whether it's a fresh start, a dream home, or a forever abode. She understands that each client has unique priorities and motivations, and she strives to tailor her approach to their specific needs. 


Outside of work, Lindsay enjoys running and reading, finding solace and inspiration in these activities. She appreciates the tight-knit nature of her community, where neighbors look out for one another and create a sense of belonging. Living near Waveny Park, Lindsay takes advantage of its beautiful trails and fields for exercise and relaxation. The exceptional school system in the area further enhances the appeal of the community.   She cherishes her family: her spouse, their five children, and their two dogs and a cat. Family holds a special place in her heart, and she remains close to her lifelong friends from her formative years. Lindsay actively participates in various community initiatives, seeking to contribute to the betterment of her neighborhood.  


Lindsay brings a wealth of diverse experiences, a passion for helping others, and a commitment to finding the perfect home for her clients. Her laid-back determination, problem-solving skills, and genuine care and attention make the home-buying experience smooth and rewarding for her clients. 


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