Osprey Home Watch, Inc.

Martha’s Vineyard Premiere Home Watch Services


Welcome to Osprey Home Watch, Inc., a home watch and caretaking company situated on the picturesque island of Martha’s Vineyard. Established in 2017, our company was founded with the purpose of providing attentive care to homes on the island.

Martha’s Vineyard is indeed a special place to own a home. For properties left unoccupied for extended periods, there arises a clear need for a home watch service to safeguard your investment and provide you with the peace of mind you deserve.


Osprey Home Watch, Inc. (Osprey) will conduct a visual inspection of the exterior and interior of your home for obvious issues or concerns that may occur while you are away. We offer weekly or bi-monthly services and can tailor the inspection list to your needs. Weekly inspections are recommended since it only takes a few days for a small issue to become a major problem.

Problems such as roof leaks, plumbing failures, rodent and insect infestation, odors, forced entry or vandalism can occur anytime. Additionally, mold and mildew can grow quickly resulting in expensive damage and serious health hazards.

If these are not discovered in a timely basis things can quickly get out of hand. Osprey will be that “watchful eye while you’re away”… performing a 16+ point visual inspection (exterior and interior) of your home. Osprey will provide you with an emailed checklist and photos of any problem areas that need to be addressed within 24 hours.

Additional services available internally from Osprey – Click on Services for more information.

We welcome the opportunity to meet with you at your home to present our home caretaking program. Please contact us for an initial consultation at your convenience.

Maranda, Ben & The Osprey Team

Osprey Home Watch, Inc is your Martha’s Vineyard Premiere Home Watch Service

Our Services

The Osprey Home Watch, Inc. home caretaking Standard Service package is based on your frequency of visits through the month, weekly or bi-monthly. We will visually inspect the interior and exterior of the home along with the immediate property grounds. With each inspection visit we will forward a detailed checklist to you within 24 hours along with digital photos of any problems. The checklist items can be customized to your specific needs. We will also make recommendations for appropriate solutions.


Checklist Sample


  • All windows and doors are securely locked, and whether there are any signs of damage, forced entry, or any other condition that may be of concern;

  • Cleanliness and condition of rooms;

  • Evidence of water leaks from internal sources (plumbing, appliances, hot water heater) and exterior (ceiling, skylights, windows, and doors);

  • Inspections for pests, insects or rodents;

  • Run Faucets in sinks, tubs, showers, and flush toilets(assuming water on);

  • Check appliances for proper operation (refrigerator, freezers, hot water heaters);

  • Check electrical panel for tripped breakers and reset;

  • Check thermostats for proper settings;

  • Check smoke detectors for proper operation;

  • Check that heat is functioning properly during the winter (assuming heat is on);


  • Walk the perimeter of the home and of the property;

  • Visually inspect the roof and gutters from the ground;

  • Check for signs of pests, insects or rodents;

  • Remove mail, newspapers or other deliveries and secure them inside the house;

  • Visually inspect landscaping, garden, and lawn condition to monitor vendor services;

  • Check propane or oil tank levels;

Standard Service Package Pricing

We have standard service pricing for homes less than 2,500 square feet and between 2,500 – 5,000 square feet in the towns of Oak Bluffs, Edgartown, and Tisbury. Larger homes and other island locations will be established at the initial setup meeting.


  • Minor Repair Services
  • Package delivery or pickup
  • Moving outdoor furniture in preparation for the closing or opening of the season
  • Storm preparation assistance

  • Vehicle care: start up and battery charging

  • Power Washing stone and other durable surfaces
  • Dryer Vent Cleaning
  • Home access and waiting service for contractors or deliveries

  • Key delivery to guests, agents or contractors

  • Key delivery for lockouts of owners or guests

  • At Osprey Home Watch, our Coordination Services are designed to elevate your peace of mind. Whether you need assistance in coordinating with vendors for minor construction or repairs, home cleaning, landscaping, or various home solutions, we’ve got you covered. Our expert team is dedicated to seamlessly coordinating every detail, ensuring that your projects run smoothly, your home is well-maintained, and you can enjoy the tranquility of an organized and harmonious living space. Let Osprey be your trusted partner in coordinating the essential elements of your home’s well-being.

Additional service fees range from $50 to $100 per hour/per person, depending on the physical activity, with a one hour minimum.

Osprey Home Watch, Inc. is your Martha’s Vineyard Premiere Home Watch Service

About Osprey Home Watch

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.

Maranda Post

Originally from Central Illinois, Maranda embarked on a journey of exploration that led her to pursue a business degree in Entrepreneurship and Marketing in Paris, France, before flourishing in San Diego's hospitality industry as an Event Planner for large hotels. San Diego is also where she found her life partner, Ben. In 2020, amidst the pandemic, Maranda and Ben relocated to Martha’s Vineyard, where Ben was born and raised, prompting Maranda's career shift to Real Estate. As a dedicated REALTOR®, she found her passion for serving her clients and the community. In 2021, Maranda and Ben welcomed their amazing son, Theodore to the world. Seeking entrepreneurial expansion, Maranda connected with Will, Palmer, and David through her business mentor, leading to the perfect fit with Osprey Home Watch. Maranda's Realtor expertise provides her with the knowledge to tailor caretaking services to individual property needs. Her established local partnerships with contractors and other vendors ensure a collaborative and efficient approach to promptly address any arising issues. Maranda's event planning background, positivity, organizational skills, and genuine love for providing top-notch customer service will ensure that our valued clients and their homes are not just managed, but nurtured as well. Maranda and Ben are enthusiastic about continuing the legacy of Osprey Home Watch, committed to providing the highest level of service that the company has always been known for.

Ben Post

A 4th generation native of Martha’s Vineyard, Ben's journey took him from his hometown to Wesleyan University, Portland, Oregon, and eventually to San Diego, where he crossed paths with Maranda. The call of Martha’s Vineyard beckoned them back in 2020 to exchange vows and start a family. For Ben, the island is not just a geographical location; it's a spiritual home. With over a decade of experience leading customer success teams in the tech industry, Ben brings a wealth of skills to Osprey Home Watch. With his eye for detail and client-focused approach, he is driven to provide excellence service with every interaction. Ben comes from a family in the service trades - his father, a retired general contractor on the island for over 30 years, built their family home in West Tisbury with his own hands. As the stewards of Osprey Home Watch, Ben and Maranda are committed to working with the utmost integrity and care to ensure your valuable properties are genuinely nurtured.

Palmer Marrin

Palmer started coming to Martha’s Vineyard with her family in the early 1960s. In 1987 she and her husband, David Kleeman, bought a house in East Chop and in 2017, made the Island their full-time residence. She worked for 45 years in a Connecticut family-owned real estate business that was started by her grandmother. Although she has retained her brokerage licenses, her full focus is now on Osprey. Through her real estate brokerage work Palmer has had extensive experience in inspecting homes. In working with other homeowners, and with her own properties over the years, she knows the importance of having someone watch over a home when the owner is away. Palmer has always thoroughly enjoyed working with her clientele and providing good service.

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.

Nic Korba

Nic graduated from Martha's Vineyard Regional High School and attended Bentley University in Boston. He went on to work at Enterprise Rent-A Car where he became branch manager. The training he received enabled him to understand the concept of ``exceptional customer service``. He and his wife, Mary, decided to move to the island to start a family. Since 2013 he has been working in Real Estate. His training has given him a great work ethic, professionalism, a positive attitude, and a willingness to help his clients in any way possible.

Terry Williams

Terry has been a caretaker and artist living full-time on Martha’s Vineyard since 2013 , moving here after 20 years as a paint contractor and muralist in south Florida. He is experienced in many levels of home repair and is looking forward to putting that experience to work for Osprey.


“Just wanted to send a brief note to say how much Patty and I have appreciated the professionalism and reliability of Osprey Home Watch over the last seven years!”

“The responsiveness that you and your staff have shown when we have requested your help on short notice to open the house for a service person has been fantastic. The reliability of your consistent home watch visits has given us total peace of mind.”

“The detail contained in your summary reports after each visit has also been extremely helpful. Small details like knowing the remaining gallons of propane left in the tank or that all thermostats are set properly, have been very useful. The consistent checklist format was well conceived and a sign of your organizations professionalism.”

“We look forward to utilizing your services for many years to come!”

– Mark

“It is with confidence that we have trusted our Martha’s Vineyard home to Osprey Home Services for the past 3 years. The Osprey team is reliable, thorough and trustworthy. The team has always responded promptly when there has been an issue regarding heat loss or other problems and always communicates in a timely fashion. On a regular basis, an in-depth thorough reports is received every 2 weeks. We have recommended Osprey Home Services to others and will continue to use Osprey for our own homes’s care taking needs.”

– Carol and Bruce

“My wife and I, summer residents of East Chop, have been using the services of Osprey Home Watch for a number of years. We have always been totally satisfied with their good work. They are reliable, efficient, excellent communicators and, needless to say, good, honest people.”
“When they see something about the house or grounds that might look “not quite right,” whether it’s a safety issue or not, they will bring it to our attention and propose a remedy. Their service fees are reasonable enough and and we find their billing schedules and charges for extraordinary calls to be very acceptable.”

– Frank and Kathleen

“My husband Bill and I have engaged Osprey Home Watch for several years both before and after a large renovation to our property in East Chop on Martha’s Vineyard.”

“We live in New York so it was important that we could fully trust the company that would care take our property. The owners and employees of Osprey have been consistent and vigilant with home checks and inspections. They have been quick to discover issues and remedy those issues quickly and professionally.”

“We have also hired them for additional services when needed and have found them professional and capable. Finding contractors on the island for small jobs in nearly impossible so it has been a real perk to know we can call on them for repair work.”

“In closing, Osprey Home Watch has given us great peace of mind knowing our home is being monitored by such caring professional people.”

– Mary and William

“I have found over the past 8 years and 3 handyman services on the island that it is really difficult to find a reliable service that comes through consistently. This is exactly what Osprey does. Not only have they been able to help me and my guests when things have gone wrong in an extremely timely manner but when COVID hit and I needed help and creativity offering complete services to my guests they delivered! I could not have operated a smooth season without them. They bring a wealth of knowledge of on island resources which has proven to be invaluable.”

– Jeff

“Having owned a Vineyard house for nearly 40 years and having had many unsatisfactory caretakers over that period I can highly recommend Osprey Home Watch without reservation.”

“I was an Osprey customer for 6 years and was extremely pleased with their professionalism, consistent communication and problem-free relationship. They far surpass the service I received from other caretakers.”

“I recently sold my house and recommended to the buyer that they continue with Osprey, which they wisely have done.”

– Walter



Osprey Home Watch, Inc.
PO Box 146
Oak Bluffs, MA 02557


(619) 718 -1091


(508) 627 -1519