MaryAnn has been an active Realtor since 1986 and began with Drakeley when the office first opened. She has been a consistent leader in local sales and is a fixture in the real estate community. Consecutive CONNECTICUT FIVE STAR PROFESSIONAL AGENT.

MaryAnn is the fourth generation of her family in Litchfield County and is a current Bethlehem resident. She is involved in many community affairs, a volunteer for the American Cancer Society, gallons donor for the American Red Cross, contributor to Special Olympics, member of the Bethlehem Land Trust and a committee member of Western CT Walk to End Alzheimer's. MaryAnn is a member of Soroptimist International and Bethlehem Senior Citizen Commission. She is a participant/organizer for the Interfaith Ministries annual Christmas Party for underprivileged children, volunteers for Friends of the Bethlehem Library and is a volunteer Judge for the Bethlehem Fair. MaryAnn was a long standing past member of the High School Scholarship and Bloss Scholarship Committee.

Jeff is a lifelong local resident of Woodbury, Bethlehem and Watertown.
Property and Real Estate is second nature as Jeff has worked in the housing industry for over 25 years providing services, consultation, sales and rentals for both residential and commercial properties throughout CT.

Jeff resided in Woodbury, centrally located on the borders of Roxbury and Southbury with his wife Kellie a special education teacher at Nonnewaug High School in Woodbury, their two daughters, both in grad school, their 14-year-old Pug Marty and a revolving door of senior rescues and foster dogs.

Jeff and Kellie enjoy scouting New England collecting early American lighting and antiques and also involve themselves in local charities and events.

Jeff is available 7 days a week for consultation.

John along with his wife Corey and two sons Zak and Pepper have been residents of Woodbury/Bethlehem for over eighteen years. Prior to real estate he was owner and founding partner of MATTEO Restaurant in Watertown and General Manager of The Watertown Golf Club for fourteen seasons. He has a B.A. in business from Teikyo Post University and a graduate from the Culinary Institue of America in Hyde Park. He is a member of the Watertown Rotary, Watertown Golf Club, Nonnewaug Grid Iron Club and serves on the Board of Directors at Camp Claire, a summer camp for children located in Old Lyme.

A broker since 1974, Joyce is a life long Woodbury resident. She and her family are involved in many community affairs. She has built, renovated and converted many properties and offers this experience to all of her customers. Prior to opening her office in 1986, Joyce ran Sand Dunes Swim & Tennis Club for over twenty five years. While running the club she built forty four apartments as well as several residential renovation projects. Her current home was featured in Country Home magazine in December of 1991. Joyce is a volunteer and financial sponsor for many area organizations, such as "A Day at the Met" for local high school students. She received the prestigious Paul Harris Fellowship Award from the Tribury Rotary(Woodbury-Southbury-Middlebury)-rarely given to a non-rotarian in recognition of service to the community. 

Shelley Drakeley is a lifelong area resident and resides in Woodbury with her husband Tim. She is a graduate of Holy Cross High School, Emmanuel College and Boston College where she received her Masters Degree. Through the years, Shelley and Tim have built, renovated and restored many homes in the Woodbury area. Her expertise in decorating and interior design is her passion.

Shelley has been an active volunteer in the local schools and served as head of the Beautification Committee, a member of the Nonnewaug Grid Iron Club, a member of the St. Teresa's Women's Guild, a member of the Woodbury Junior Women's Club and served on the Board of Directors for the Highfield Club in Middlebury, CT.

Tim has been a broker and salesperson since 1991. Tim has been the #1 selling and listing broker in the Woodbury area and is one of the top producers in the Tri-bury area. He is a Graduate of Holy Cross High School, Northfield Mount Herman Prep School and Babson College. While attending Babson, Tim majored in Finance and Entrepreneurial Studies. He is the owner of Tim Drakeley Old Barns and Drakeley Construction.  Along with his wife Shelley, he has built and restored many homes in the Woodbury area. Tim is active in many youth activities, and was the Nonnewaug High School Varsity boys basketball coach for 24 years. He served as a Chairmen of the Woodbury Park and Recreation Committee and as the President of Nonnewaug Athletic Club, a non profit organization.

Josh Harwood, along with his wife and 2 children, has lived in Woodbury for 24 years. Josh holds a B.A. from Hamilton College, has 30+ years sales and executive experience in NYC and Boston, and enjoys bringing this strong background to each real estate relationship and transaction. Josh is active locally; as Quassapaug Sailing Center sponsor (where he served on the board for several years), as a volunteer and committee member for Flanders Nature Center. He coached youth sports for Woodbury Parks & Recreation for several years and is a member of the Woodbury United Methodist Church.

Originally from Woodbury, Lauren lived in New York City for over a decade but always found herself returning to this area to be with family and enjoy the outdoors. She eventually moved back to Litchfield County to work at her alma mater, The Taft School. Lauren is a licensed therapist who holds a masters degree in social work and a doctorate in psychology. When searching for a home in the area, Lauren fell in love with real estate; she then pursued her salesperson license with the goal of helping others through the real estate process. Lauren is detail-oriented, driven, and excels at listening and understanding clients' needs. She currently resides in Bethlehem in an 18th-century saltbox house. Her husband, Carter Mosch, is a fine woodworker, and her two children attend Rumsey Hall School. In her free time, Lauren can be found hiking in Washington or traveling to the Adirondacks with her family.

Taylor O'Keefe is a proud, life-long Woodbury and Watertown resident who wants to share all that Litchfield, New Haven, and Fairfield Counties have to offer with anyone who shows an interest. Working locally for many years, she's developed numerous connections in the surrounding areas, and prides herself in her local recommendations and resources.

Taylor cares deeply for every client that she's lucky enough to work with. Taylor is known for her around-the-clock availability and dependability, responsiveness, and ability to get the deal done. Her dedication and passion towards real estate is second to none.

A graduate of Nonnewaug High School and The Culinary Institute of America where she received her Bachelors in Professional Studies, Taylor enjoys volunteering her time in the community and sharing her culinary knowledge with local high school students and anyone that she comes in contact with.

When Taylor's not working, she loves spending time with her two dogs, Mack and Reese, her family and friends, eating at local restaurants, and cooking and baking at home in her kitchen.

Katherine has a life-long connection to the communities of Woodbury and Bethlehem. Known as Kat to many, she originally grew up in Bethlehem and is a graduate of Nonnewaug High School. She earned her Bachelor's Degree from Marist College in New York and her Master's Degree from Central Connecticut State University. Katherine is a frequent donor to Goodwill and animal adoption agencies. In her free time, Katherine enjoys her walks on Main Street, taking her parents for lunch at the Charcoal Chef and traveling with friends and family.

Paige is a Litchfield County native who loves the active and creative lifestyle the area nurtures. Driven by a desire to help others, Paige found her calling in real estate by serving her clients and guiding them through one of the most impactful investments of their lives. She consistently demonstrates a high level of integrity and commitment in every transaction, and clients love her warmth, patience, and follow through. Creating a seamless transaction is her number one priority.

Paige resides in Watertown with her husband Albie, their son Romeo, and two rescue dogs, Jenny and Lido. She divides her non-working hours between hiking all the amazing spots in the local area and being at home in her garden. She and her husband also share a passion for skiing, with regular trips to various Vermont mountains in the winter.

Ashley Stewart is a Woodbury native who now resides in Southbury with her husband Matt. She is a graduate of Nonnewaug High School, where she was a part of the agricultural program. She volunteers at local animal shelters and events involving 4-H and county fairs. She has previously worked as a Veterinary Technician and an Oral Surgery Assistant in surrounding towns. In her spare time, Ashley loves to go on hikes with her dogs, do DIY projects around the house, and spend time with her family and friends. She is eager and excited to help give back to her community by helping you find your perfect home!

Rhonda has lived in the Woodbury/Bethlehem area since age 9.  She graduated from Nonnewaug High School and currently resides in Woodbury with her 3 children and dog.  Rhonda has worked at Newtown Savings Bank in Woodbury since 1994 and is currently the Customer Experience Manager. She has been an active member of the Woodbury Junior Woman's Club for many years and has volunteered at the American Cancer Society Relay for life for the past 10 years.  When she's not working, Rhonda enjoys watching football and traveling to Charleston, SC where she is originally from.

Rhya Szymansky is a lifelong Woodbury resident with her husband David and three young sons. After graduating from Nonnewaug High School, Rhya continued her education at Western CT State University where she received her Master's Degree in Elementary Education. She taught kindergarten and first grade for 10 years in Naugatuck before resigning to be home and raise her sons.
Most weekends you can find her at the soccer field cheering on her boys! She loves spending time with her family, going on hikes and skiing. She is also an active volunteer for Mitchell Elementary School and for the Naugatuck Mobile Food Pantry.
Rhya comes equipped with the knowledge and love for Woodbury and its surrounding small towns. She hopes to share and spread this love by helping others find the perfect place to call home!