Contact Information
Service Areas

Serving Martha’s Vineyard, including the towns of Oak Bluffs, Edgartown, Vineyard Haven, West Tisbury, Chilmark, and Aquinnah.

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

Welcome to Osprey Home Watch, where our dedicated team of year-round Martha’s Vineyard residents offers a unique advantage. With deep roots in the community, we possess an unparalleled understanding of the needs of second-home owners. What sets us apart is our wealth of experience and local expertise.

Meet Maranda Post, our owner, who brings a unique perspective as a professional REALTOR® on Martha’s Vineyard. With her background, she customizes caretaking services to meet the unique needs of individual properties. Maranda’s extensive local partnerships ensure a collaborative approach to addressing arising issues efficiently. Her background in event planning, positivity, organizational skills, and a genuine love for providing top-notch customer service ensure your homes are not just managed but nurtured.

Co-owner Ben Post, a 4th generation native of Martha’s Vineyard, comes from a family with a long history in MV-based service trades. His eye for detail and client-focused approach, coupled with over a decade of tech industry experience, drive him to provide excellence in every interaction.

Together, our team is enthusiastic about providing top-notch service, ensuring our clients feel secure and at ease about their Island property from afar. Our commitment to delivering extra peace of mind includes proven and documented visits. Your property is in capable hands with Osprey Home Watch.


We are confident that Osprey provides a high-quality product at competitive prices on the Vineyard. As we oversee and secure high-value properties on the Island, we’ve gone the extra mile to ensure we are properly bonded, insured, and licensed in the State of Massachusetts.


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