Search

Leave a Message

Thank you for your message. We will be in touch with you shortly.

Explore Our Properties
Background Image
Trusted Agent

Meet Kelly Hess

Kelly  Hess

Kelly Hess

Kelly Hess – Luxury Vacation Rental Specialist

A Martha’s Vineyard resident for 26 years, Kelly brings a wealth of experience to Match Point Properties, specializing in luxury vacation rentals for the past 10 years. With a background in hospitality, she has a keen understanding of exceptional service, ensuring each rental experience is seamless and unforgettable.

Kelly and her husband, Mark Hess, General Manager of the Edgartown Golf Club, have raised their two children in Edgartown, fully embracing the island’s charm and community. Her deep local knowledge, passion for island living, and commitment to excellence make her a valuable asset to Match Point Properties and those seeking the perfect Vineyard getaway.

Contact Details

Email address [email protected]
Primary phone (508) 560-0525
Address 205 Upper Main St Edgartown MA, 02539
See Why Our Clients Love Us

Testimonials

Read what our clients have to say about working with us.

"Fran Agnoli listened carefully to our priorities. She advised us on price and strategy in a clear and experienced-based way. She was always professional, warm, courteous. She was an absolute delight to work with. "
"Fran Agnoli listened carefully to our priorities. She advised us on price and strategy in a clear and experienced-based way. She was always professional, warm, courteous. She was an absolute delight to work with. "
Linda M
"Fran has always been a friendly face in the community we knew she would have the working knowledge to help us with this purchase. Fran made herself accessible to us 24/7. We are busy individuals so we often would chat outside typical office hours. Fran made us feel like her only client and we had 100% of her attention. We cannot say enough about our positive experience. "
"Fran has always been a friendly face in the community we knew she would have the working knowledge to help us with this purchase. Fran made herself accessible to us 24/7. We are busy individuals so we often would chat outside typical office hours. Fran made us feel like her only client and we had 100% of her attention. We cannot say enough about our positive experience. "
Kate F & Doriana K
"Fran was excellent from beginning to end. Very good communicator and very professional. "
"Fran was excellent from beginning to end. Very good communicator and very professional. "
Nicholas L
"We have worked with Match Point Properties for 15+ years! They have helped us in home purchases/rentals, renovations, and property management. The professionalism, and quality of work is unmatched. We cannot recommend Paul and Match Point Properties enough and regularly send family & friends to him. Having Match Point with us all these years later has afforded our family total stress-free enjoyment every time we are on the Vineyard!"
"We have worked with Match Point Properties for 15+ years! They have helped us in home purchases/rentals, renovations, and property management. The professionalism, and quality of work is unmatched. We cannot recommend Paul and Match Point Properties enough and regularly send family & friends to him. Having Match Point with us all these years later has afforded our family total stress-free enjoyment every time we are on the Vineyard!"
Chad and Michelle V.
"An all-around phenomenal experience! Surpassed our expectations many times over – Our Broker, Paul, not only negotiated an off-market property on our behalf, but organized and oversaw several remodeling projects in conjunction while sticking to an extremely tight timeline. His team was literally there to start the demo less than an hour after closing - his organizational skills, attention to detail and responsiveness are incredible, and made buying a home from long distance way too easy!"
"An all-around phenomenal experience! Surpassed our expectations many times over – Our Broker, Paul, not only negotiated an off-market property on our behalf, but organized and oversaw several remodeling projects in conjunction while sticking to an extremely tight timeline. His team was literally there to start the demo less than an hour after closing - his organizational skills, attention to detail and responsiveness are incredible, and made buying a home from long distance way too easy!"
Brian H.
"You won't find a more knowledgeable, attentive, customer-focused team on the Island anywhere. Paul helped us understand the Edgartown market, acted as our buying agent for our new home, and personally managed countless projects for us with his extensive network of professionals on the island (carpenters, electricians, landscapers, multiple other specialty areas). He and MatchPoint offers an invaluable service of navigating a highly competitive market and ability to get things done with scarce resources - made even more difficult if at times you are trying to manage from afar. We could not recommend more highly."
"You won't find a more knowledgeable, attentive, customer-focused team on the Island anywhere. Paul helped us understand the Edgartown market, acted as our buying agent for our new home, and personally managed countless projects for us with his extensive network of professionals on the island (carpenters, electricians, landscapers, multiple other specialty areas). He and MatchPoint offers an invaluable service of navigating a highly competitive market and ability to get things done with scarce resources - made even more difficult if at times you are trying to manage from afar. We could not recommend more highly."
Jodi R.

Find Your Next Dream Home

Browse Homes

The photography on our site was done by Larry Glick, Bob Gothard, and David Welch.

Follow Us on Instagram