$260,000
2 bd2 ba1,456 sqft Woodbury, CT
2 bd2 ba1,456 sqft
Woodbury, CT
Sold 14 days ago
Seller
Meet Team Drakeley
10 members
Taylor Hamel (O'Keefe)
5.0 (101)
price range
sales last 12 months
Maryann Bennett
5.0 (60)
price range
sales last 12 months
Joyce Drakeley
4.9 (41)
price range
sales last 12 months
Katherine Parlato
5.0 (26)
price range
sales last 12 months
Shelley Drakeley
5.0 (16)
price range
sales last 12 months
Jeffrey Boucher
5.0 (14)
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...
Specialties
34 Years of experienceBuyer's AgentListing AgentRelocationCommercial PropertiesProperty ManagementNew Construction
Team listings & sales (2024)
For Sale
For Rent
Sold
This map can show the most recent 100 listings and 100 sales. Review all listings and sales below.
For Sale (28)
Address | Bed/Bath | Listing price |
|---|---|---|
 2 Judd Hill Rd Woodbury, CT 06798
| 3 Bed, 2 Bath | $599,900 |
 8 Curtiss Mdws Woodbury, CT 06798
| 4 Bed, 5 Bath | $949,900 |
 43 Bethwood Ln Woodbury, CT 06798
| 3 Bed, 2 Bath | $499,900 |
 10 Pelham Way Unit 10 Middlebury, CT 06762
| 3 Bed, 3 Bath | $650,000 |
 43 Woodbury Hl Unit 43 Woodbury, CT 06798
| 2 Bed, 2 Bath | $539,000 |
For Rent (1)
Address | Bed/Bath | Listing price |
|---|---|---|
 4 Main St S Unit 2 Woodbury, CT 06798
| 2 Bed, 1 Bath | $2,200/mo |
Sold (1995)
Address | Sold date | Closing price | Represented | Flag Sale |
|---|---|---|---|---|
| 4/30/2026 | $260,000 | Seller | ||
| 4/24/2026 | $200,000 | Buyer and Seller | ||
| 4/20/2026 | $665,000 | Buyer | ||
| 4/16/2026 | $530,000 | Buyer | ||
| 4/9/2026 | $270,000 | Seller |
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...
