220 Upper Grassy Hill Rd

Since 1991, Tim Drakeley has solidified his reputation as a premier broker and salesperson, consistently ranked as Woodbury, CT’s #1 selling and listing broker for 12 years and a top producer in the Tri-bury region and all of Litchfield County. A graduate of Holy Cross High School, Northfield Mount Hermon Prep School, and Babson College, where he studied Finance and Entrepreneurial Studies, Tim brings deep expertise to Drakeley Real Estate. Founded in 1986 by his mother, entrepreneur Joyce S. Drakeley, this family-owned firm has earned a 39-year legacy of trust and integrity, serving home buyers and sellers across Connecticut. As owner and broker since 2018, Tim, alongside Joyce and their dedicated team, builds enduring client and community relationships. Tim’s commitment to community shines through Drakeley Real Estate’s generous support for local nonprofits, including donations of time and resources to Flanders Nature Center, Southbury and Woodbury Woman’s Clubs, and numerous local sports organizations. A passionate community leader, Tim has coached Nonnewaug High School’s Boys Varsity Basketball for over 25 years and currently leads the 7th-grade girls’ travel basketball team through Woodbury Park and Recreation. He serves as President of the Nonnewaug Athletic Club, a nonprofit supported by Drakeley Real Estate, and as President of Highfield Country Club. Together with his wife, Shelley, Tim has restored numerous Woodbury homes and owns Tim Drakeley Old Barns and Drakeley Construction. ”When you work with us, your house is not just a sale or a number; our partnership is a lifelong connection” a Drakeley motto that the family thrives to deliver on. Whether it’s helping you find your right home or prioritizing finding ways to give back to the Woodbury community, Drakeley Real Estate is committed to their mission.