Our History

Welcome to your one-stop source for real estate and insurance services!  Our expertise and "home-town" customer service have made us a staple in the Lakes Region of Maine since 1934.



Our family owned and operated company provides exceptional customer service since 1934.  We build our reputation on hard work, honesty and trust; by investing in our customers to provide an independent answer to real estate and insurance needs.

“Strive not to be a success, but rather to be of value.”

— Albert Einstein


Our Team

Oberg 2018-05-29 (77).JPG

James Oberg - Insurance & Real Estate Agent

James is the fourth generation of the Oberg family to join the business. James has 6 years experience working for the Liberty Mutual Insurance as a manager of Commercial Lines Analytics. He joined the agency in 2016 and will specialize in commercial insurance and real estate.

James graduated from Bentley University and will use his 30 years of experience in the Lakes Region community to help with your needs.

Email: James@ObergAgency.com
Cell: 207-939-8065
Office: 207-647-5551

Oberg 2018-05-29 (177).JPG

Pete Oberg - Insurance Agent & Designated Real Estate Broker

Pete is the third generation of Obergs to preside over the Oberg Insurance and Real Estate Agency. He has been a Real Estate and Insurance Agent for over 40 years and is very involved with the Lakes Region Community. He is presently the President of the Bridgton High School Scholarship Foundation, serves on the town Revitalization Committee, Bridgton's Waste Water Management Committee and other various boards

Pete graduated from the University of Maine and heads up the insurance division of the agency and is also the Designated Broker on the Real Estate side.

Email: Pete@ObergAgency.com
Cell: 207-632-6568
Office: 207-647-5551

Oberg 2018-05-29 (193).JPG

Judy Oberg - Real Estate Agent

Judy has been in the Real Estate industry for over 20 years. She has been named Western Maine Realtor of the Year and currently is the residing President of the Western Maine Real Estate Board.

Judy graduated from the University of New Hampshire. She is very involved with the community and has served on many boards, including the school board for 12 years. She enjoys singing, skiing, swimming, travel and all the greater Lakes Region area has to offer.

Call Judy today for expert Real Estate information for both Buyers and Sellers.

Email: Judy@ObergAgency.com
Cell: 207-838-0059
Office: 207-647-5551

Oberg 2018-05-29 (201).JPG

Cindy Gorman - Insurance & Real Estate Agent

Cindy has been a Real Estate broker for over 40 years. She has been awarded the Western Maine Realtor of the Year honors and has served as the Western Maine Board Secretary for over 10 years.

Cindy was born and raised in Bridgton, Maine and is an expert on the Lakes Region and surrounding areas. Cindy is also a licensed Insurance Agent with the Oberg Agency and can help clients with their personal insurance needs.

Give Cindy a call today for the real insider’s scoop on Lake Region & Real Estate!

Email: Cindy@ObergAgency.com
Cell: 207-347-1595
Office: 207-647-5551

Oberg 2018-05-29 (61).JPG

Bailey Damon - Real Estate Agent

Bailey is the newest addition to the Oberg team, joining us from the Fryeburg/Lovell area. She was raised in the Lakes Region and is very familiar with the area. After a few years as a recruiter in San Francisco and New York City, she has returned to her hometown to focus on the sale of real estate in the place she loves.

Bailey is a graduate of Suffolk University in Boston, MA. She is an RYT-200 certified yoga teacher and a lover of good food. She is here to help you buy your first, second or seasonal home!

Email: Bailey@ObergAgency.com
Cell: 207-441-2880
Office: 207-647-5551

Oberg 2018-05-29 (242).JPG

Joan Leland - Office Manager & Real Estate Agent

Joan has been managing our front office for the past seven years. She has a background in the insurance industry as a claims processor and has held a Maine real estate license since 2004. Joan has a passion for helping people, a talent for keeping things in order and a love for technology. Her customer service background and outgoing personality assure that our customers will get a sincere welcome by phone or in person!

Email: Joan@ObergAgency.com
Office: 207-647-5551


Ben Chaine - Real Estate & Insurance Agent

Ben is a great addition to our local team, born and raised in Bridgton! Acquiring his real estate license in 2017, he will use his local knowledge to help you with all of your real estate needs. He is a young ambitious realtor who feels he can connect well with the younger generation buying their first homes and connect with sellers marketing to this demographic. Ben studied business at Thomas College in Waterville, Maine and looks forward to helping you find your new home!

Ben also has his insurance license and would be happy to help you with your insurance needs!

Email: Ben@ObergAgency.com
Cell: 207-256-0671
Office: 207-647-5551