Contact Information
25 Lexington Ave, P O Box 146, Oak Bluffs, Massachusetts 02557
Year Established
Hours of Operation
Generally 9 to 5 unless we get an off hour security alarm
Accepted Forms of Payment

check, credit card and bank payments


Massachusetts watch guard license, Massachusetts State Police, # LW0245A
Commercial General and Professional Liability, Evanston Insurance Company, # 3AA171700
Dishonesty Bonding, Western Surety Company, # 63192449

About Our Company

Owners Will Bryan and Bob Merritt are year round residents of East Chop in Oak Bluffs. We have both been coming to the Vineyard to vacation over the past 60+ years and we have an appreciation for the needs of second home owners and the issues that can present themselves in vacant homes during the off season. The value that we bring to this business is the many years of home ownership and the sense of business duty and detail instilled in us from our professional careers.

We look forward to providing quality service and helping our clients feel secure and at ease about their Island property far away. We think the added feature of proven and documented visits will help give extra peace of mind.

Licensed, Bonded and Insured.
We believe that Osprey Home Watch is offering a quality product for competitive prices in the Vineyard marketplace. As we are monitoring and securing high value properties on the Island we have taken the additional steps to be properly bonded, insured and also licensed in the State of Massachusetts.