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.   



Will Bryan

Will and Heidi moved to the island permanently in July of 2016. Will spent most of his career (30+ years) in the investor side of the mortgage business, developing strong relationships with numerous clients across the country. Will and Heidi have three grown children who are all married and enjoy visiting the Vineyard every summer along with their kids.  They have owned a second home on the vineyard for 20+ years and are very familiar with the need to have a trusted person looking after one of your most important assets.


Bob Merritt

Bob & Ali moved to the Island permanently in November of 2016 and have thoroughly enjoyed their first winter.  Bob & Ali have two grown children and three grandchildren.  Bob’s work history includes many years in the Tennis/squash recreation and Insurance Agency Management in Burlington, Vermont.  Bob is also excited to be managing the East Chop Tennis Club starting this June and hopefully for many years.  Bob & Ali have been renting their East Chop home every summer since 1997 and have great experience with island home maintenance and working with contractors all through the year.