
Meet Team Drakeley
10 members

Taylor Hamel (O'Keefe)
price range
sales last 12 months

Maryann Bennett
price range
sales last 12 months

Joyce Drakeley
price range
sales last 12 months

Katherine Parlato
price range
sales last 12 months

Shelley Drakeley
price range
sales last 12 months

Jeffrey Boucher
price range
sales last 12 months
Get to know Team Drakeley
Broker
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. Found...
Team sales and listings (2,031)
This map and property list shows the most recent 100 sales and 100 listings
Sold (2,001)
- $145,000
- 2 bd
- 1 ba
- 913 sqft
229 Bacon Pond Road #453, Woodbury, CT 06798Sold 9 days agoBuyer
- $850,000
- 4 bd
- 3 ba
- 3,330 sqft
99 Plumb Brook Road, Woodbury, CT 06798Sold 10 days agoSeller
- $212,500
- 2 bd
- 2 ba
- 1,182 sqft
47 Woods Way #47, Woodbury, CT 06798Sold 10 days agoSeller
- $530,000
- 4 bd
- 2 ba
- 1,884 sqft
58 Steele Brook Road, Watertown, CT 06795Sold 11 days agoSeller
- $620,000
- 3 bd
- 3 ba
- 2,658 sqft
193 Ridgewood Drive #193, Middlebury, CT 06762Sold 16 days agoSeller
For sale (30)
- $399,000
- 2 bd
- 2 ba
- 1,467 sqft
297 Allentown Road, Terryville, CT 06786House for SaleCedar shingle sided ranch
Drakeley Real Estate, Inc. - $519,000
- 2 bd
- 3 ba
- 1,796 sqft
63 Woodbury Hill #63, Woodbury, CT 06798House for SaleOpen: Sat 12:30-2pm (6/13)
Drakeley Real Estate, Inc. - $649,000
- 4 bd
- 3 ba
- 2,832 sqft
10 Carmel Hill Road South, Bethlehem, CT 06751House for SaleSwimming pool
Drakeley Real Estate, Inc. - $525,000
- -- bd
- -- ba
- -- sqft
Mount Mauwee Road, Kent, CT 06757House for Sale13 days on Zillow
Drakeley Real Estate, Inc. - $439,000
- 3 bd
- 3 ba
- 2,194 sqft
53 Hampton Road, Waterbury, CT 06708House for SalePrice cut: $20,000 (5/30)
Drakeley Real Estate, Inc.
Team reviews (308)
Reviews represent all team members.
- 5.0
- 2/23/2026
- • jlgodbout85
Sold a Single Family home in 2025 in Woodbury, CT.
Review for: Taylor Hamel (O'Keefe)Taylor is so easy to work with. She is responsive and extremely knowledgable. She listed our house and it was under contract within 7 days! She made the entire process...Taylor is so easy to work with. She is responsive and extremely knowledgable. She listed our house and it was under contract wit...5.0- 2/4/2026
- • lbreon
Bought a Single Family home in 2025 in Woodbury, CT.
Review for: Taylor Hamel (O'Keefe)Taylor was extremely helpful with the purchase of our first home. She assisted us with the process making steps that seemed stressful easy to accomplish. She presented ou...Taylor was extremely helpful with the purchase of our first home. She assisted us with the process making steps that seemed stress... - Kat did an amazing job all the way through. In the beginning, with finding a property she was very resourceful and knew the area well. Then for the negotiation she reall...Kat did an amazing job all the way through. In the beginning, with finding a property she was very resourceful and knew the area ...MaryAnn Bennett is a professional and genuine realtor??She is kind, flexible with showings, and very knowledgeable with the properties we were interested in seeing and s...MaryAnn Bennett is a professional and genuine realtor??She is kind, flexible with showings, and very knowledgeable with the proper...
- 5.0
- 12/11/2025
- • stillsusan
Sold a Single Family home in 2025 in Bethlehem village, Bethlehem, CT.
Review for: Maryann BennettMaryann is an awesome relator. She had beautiful pictures taken of our house. She was very attentive and listened to our needs. She sold our house in just three weeks. Am...Maryann is an awesome relator. She had beautiful pictures taken of our house. She was very attentive and listened to our needs. Sh...This was my second closing with Mary Ann. She was reliable, prompt, knowledgeable, and always had a great attitude. Also, she is always friendly. Jeff and I are so grat...This was my second closing with Mary Ann. She was reliable, prompt, knowledgeable, and always had a great attitude. Also, she is ... - 5.0
- 12/9/2025
- • tom outwater
Sold a Single Family home in 2025 in Litchfield, CT.
Review for: Maryann BennettMaryann is the finest realtor I have ever had. From day one, she had comps, photographers and possible buyers already lined up. She is extremely thorough and knowledgea...Maryann is the finest realtor I have ever had. From day one, she had comps, photographers and possible buyers already lined up. ...Working with Maryann was an exceptional experience from start to finish. She listened carefully to what I needed, offered honest and thoughtful advice, and kept me inform...Working with Maryann was an exceptional experience from start to finish. She listened carefully to what I needed, offered honest a... - 5.0
- 11/30/2025
- • fullrun
Sold a Single Family home in 2025 in Woodbury, CT.
Review for: Maryann BennettMaryann is exceptional... not only as a real estate agent but as a human being. And as a seller you want that element to be very present... so that the commitment is bey...Maryann is exceptional... not only as a real estate agent but as a human being. And as a seller you want that element to be very ...5.0- 11/24/2025
- • Betsy
Sold a Single Family home in 2024 in Bethlehem village, Bethlehem, CT.
Review for: Maryann BennettMaryann is an absolute joy to work with. She’s attentive, thorough, and completely professional. She helped us to sell our house during a very difficult time. Maryann’s c...Maryann is an absolute joy to work with. She’s attentive, thorough, and completely professional. She helped us to sell our house d...




