Skip main navigation

Drakeley Real Estate

Drakeley Real EstateLead of Team Drakeley
5.0stars312 team reviews
Contact the team
Team

Recent Sales

Sales numbers represent all team members
Skip to the end of the carousel
  • $120,000
    1 bd1 ba546 sqft Woodbury, CT
    1 bd1 ba546 sqft
    Woodbury, CT
    Sold 8 days ago
    Seller
    22 Pilgrim Trail #G1, Woodbury, CT, 06798
  • $625,000
    3 bd3 ba2,042 sqft Woodbury, CT
    3 bd3 ba2,042 sqft
    Woodbury, CT
    Sold 11 days ago
    Seller
    27 Middle Quarter Road, Woodbury, CT, 06798
  • $840,000
    4 bd5 ba3,865 sqft Woodbury, CT
    4 bd5 ba3,865 sqft
    Woodbury, CT
    Sold 16 days ago
    Seller
    8 Curtiss Meadows, Woodbury, CT, 06798
  • $375,000
    2 bd1 ba798 sqft Middlebury, CT
    2 bd1 ba798 sqft
    Middlebury, CT
    Sold 19 days ago
    Seller
    89 Sandy Beach Road #89, Middlebury, CT, 06762
  • $400,000
    9 bd8 ba4,492 sqft Woodbury, CT
    9 bd8 ba4,492 sqft
    Woodbury, CT
    Sold 22 days ago
    BuyerSeller
    137 & 141 Main Street South, Woodbury, CT, 06798
  • See more
Skip to the beginning of the carousel
108
Sales last 12 months
2,063
Total sales
$22K-$1.8M
Price range
$477K
Average price

Meet Team Drakeley

10 members

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
Buyer's AgentListing AgentRelocationCommercial PropertiesProperty ManagementNew Construction
34 Years of experience
Visit team website
FacebookInstagramX

Team sales and listings (2,094)

This map and property list shows the most recent 100 sales and 100 listings

Sold
For sale
Skip sales and listings map
Go back to the sales and listings map

Sold (2,063)

Skip to the end of the carousel
Skip to the beginning of the carousel

For sale (31)

Skip to the end of the carousel
  • Drakeley Real Estate, Inc.
  • Drakeley Real Estate, Inc.
  • Drakeley Real Estate, Inc.
Skip to the beginning of the carousel

Team reviews (312)

Reviews represent all team members.

Skip to the end of the carousel
  • 5.0
    • 10/27/2026
    • • Jeffrey Cote

    Sold a Single Family home in 2025 in Bethlehem village, Bethlehem, CT.

    Review for: Maryann Bennett
    Maryann helped us through the difficult task of selling our childhood home. Her knowledge and expertise was top notch. Always available whenever we had questions. Her adv...
    Maryann helped us through the difficult task of selling our childhood home. Her knowledge and expertise was top notch. Always avai...
    5.0
    • 10/26/2026
    • • joereing35

    Sold a Single Family home in 2026 in Morris, CT.

    Review for: Maryann Bennett
    Maryann is the absolute best, would never consider using anyone else. She is very professional and helped us navigate the ever changing demands of the market. She was alw...
    Maryann is the absolute best, would never consider using anyone else. She is very professional and helped us navigate the ever cha...
  • 5.0
    • 9/20/2026
    • • rjenny57

    Bought and sold a Single Family home in 2026 in Woodbury, CT.

    Review for: Katherine Parlato
    Buying a new home and selling your current home is a stressful process. Katherine guided me through the process of doing both with seamless and flawless expertise. Kat wo...
    Buying a new home and selling your current home is a stressful process. Katherine guided me through the process of doing both with...
    5.0
    • 7/6/2026
    • • Marc Lippman

    Bought and sold a home in 2026.

    Review for: Jeffrey Boucher
    Jeffrey is the absolute best at what he does!!! I would give him 10 stars if that was an option. He always goes above and beyond. If you need a realtor he’s your man, th...
    Jeffrey is the absolute best at what he does!!! I would give him 10 stars if that was an option. He always goes above and beyond....
  • 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...
  • 5.0
    • 1/14/2026
    • • robgw83

    Bought a home in 2026.

    Review for: Katherine Parlato
    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 ...
    5.0
    • 12/12/2025
    • • Dj Dublin

    Bought a Condo home in 2025 in Middlebury, CT.

    Review for: Maryann Bennett
    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 Bennett
    Maryann 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...
    5.0
    • 12/9/2025
    • • dianne slater111984

    Bought a home in 2025.

    Review for: Maryann Bennett
    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 ...
Skip to the beginning of the carousel
Add a review

Service areas (18)

TEAM

Drakeley Real Estate

Drakeley Real EstateLead of Team Drakeley
5.0stars312 team reviews
108sales last 12 months
2,063total sales
$22K-$1.8Mprice range
$477Kaverage price
34years of experience
(203) 510-9184
tim@drakeley.com
256 Main Street South
Woodbury, CT, 06798