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Tim Drakeley

Woodbury, CT
Drakeley Real Estate, Inc.
202 Closed Sales
$92.4M Total Value
$30K - $5.4M Price Range
$457.6K Average Price
Prior five years

About Tim

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.
Home Types: Commercial, Lot/Land, House, MultiFamily, Condo, Townhouse
Years of Experience: 34
Education: Babson College

Transaction History

Seller Deals

Total Deals
24
Total Value
$12,237,500
Average Sale Price
$509,896
Price Range
$50K - $1.3M

Buyer Deals

Total Deals
8
Total Value
$3,240,000
Average Sale Price
$405,000
Price Range
$100K - $800K

Production Over Time

1 Year View by Quarter

Seller Deals

Total Deals
54
Total Value
$26,066,700
Average Sale Price
$482,717
Price Range
$40K - $1.8M

Buyer Deals

Total Deals
9
Total Value
$3,570,000
Average Sale Price
$396,667
Price Range
$100K - $800K

Production Over Time

2 Year View by Quarter

Seller Deals

Total Deals
165
Total Value
$72,907,470
Average Sale Price
$441,863
Price Range
$30K - $1.8M

Buyer Deals

Total Deals
37
Total Value
$19,528,738
Average Sale Price
$527,804
Price Range
$50K - $5.4M

Production Over Time

5 Year View

Tim's Listings and Deals

Awards and Designations

  • NAR - National Association of Realtors
Agent License #REB.0193579
Agent Photo

Tim Drakeley