Search

Leave a Message

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

Explore Our Properties

Dedication. Expertise. Trusted.

Exceptional Real Estate on Martha’s Vineyard

With offices at 238 Upper Main Street and 205 Upper Main Street in Edgartown, Match Point Properties is a locally owned real estate firm specializing in sales, rentals, and property management. Committed to professionalism and personalized service, we take a hands-on approach to every client relationship, ensuring a seamless and rewarding experience.

Whether you're looking to buy, sell, or rent on Martha’s Vineyard, our expertise and deep local knowledge will guide you every step of the way. Let us help you find the perfect home or investment with the care and attention you deserve.

Our Team Experts

Get to Know Us

Our team combines expertise with a refined, personal approach to make your Martha’s Vineyard real estate experience seamless. Whether you’re buying, selling, or renting, we are dedicated to guiding you toward the perfect fit—helping you find a home that truly complements your lifestyle with ease and sophistication.

No result found

Our Collection

Notable Listings & Sales

Browse our exclusive listings and find your next dream home today!

  • 39 Plantingfield Way Sold

    $14,000,000

    39 Plantingfield Way, Edgartown, MA 02539

    • 4 Beds
    • 4 Baths
    • 6,345 Sq.Ft.
  • 52 S Summer St Sold

    $8,500,000

    52 South Summer Street, Edgartown, MA 02539

    • 7 Beds
    • 7 Baths
    • 920 Sq.Ft.
  • 27 Pierce Lane Sold

    $7,800,000

    27 Pierce Lane, Edgartown, MA 02539

    • 6 Beds
    • 4.5 Baths
    • 3,910 Sq.Ft.
  • 88 N Water St Sold

    $6,100,000

    88 N Water Street, Edgartown, MA 02539

    • 7 Beds
    • 5.5 Baths
    • 5,018 Sq.Ft.
  • 114 N Water St Sold

    $6,050,000

    114 N Water Street, Edgartown, MA 02539

    • 9 Beds
    • 4.5 Baths
  • 45 Winter St Sold

    $4,600,000

    45 Winter Street, Edgartown, MA 02539

    • 5 Beds
    • 4.5 Baths
    • 2,928 Sq.Ft.
View All
See Why Our Clients Love Us

Testimonials

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

"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.
"We’ve had the absolute pleasure of working with Paul across every facet of our property—from construction and renovations to sales and ongoing management—and we couldn’t be happier. His attention to detail, professionalism, and deep understanding of the Vineyard market have been invaluable. Paul treats our home with the same care and commitment as if it were his own, which gives us complete peace of mind. Whether overseeing a complex project or handling day-to-day property needs, he is always one step ahead. It’s rare to find someone so capable across such a wide range of services, and we continue to rely on Paul time and again. We truly can’t imagine managing our Vineyard home without him. The two Screenshots attached can go under Fran. Just use first name and initial of last name."
"We’ve had the absolute pleasure of working with Paul across every facet of our property—from construction and renovations to sales and ongoing management—and we couldn’t be happier. His attention to detail, professionalism, and deep understanding of the Vineyard market have been invaluable. Paul treats our home with the same care and commitment as if it were his own, which gives us complete peace of mind. Whether overseeing a complex project or handling day-to-day property needs, he is always one step ahead. It’s rare to find someone so capable across such a wide range of services, and we continue to rely on Paul time and again. We truly can’t imagine managing our Vineyard home without him. The two Screenshots attached can go under Fran. Just use first name and initial of last name."
Goeff C.
"Selling a home is stressful and selling one you love is emotional as well. Match Point Properties and their agent Kelly understood that and were supportive throughout. Kelly not only navigated us through all the permitting and selling procedures but directed us to other helpful services that we could use to help the actual moving process. This included organizing a furnishings or contents sale and physically helping to dismantle furniture. We’re very grateful to Match Point for their knowledge, advice and direction, and especially to Kelly for her support and understanding."
"Selling a home is stressful and selling one you love is emotional as well. Match Point Properties and their agent Kelly understood that and were supportive throughout. Kelly not only navigated us through all the permitting and selling procedures but directed us to other helpful services that we could use to help the actual moving process. This included organizing a furnishings or contents sale and physically helping to dismantle furniture. We’re very grateful to Match Point for their knowledge, advice and direction, and especially to Kelly for her support and understanding."
Mary M.
Instant property Valuation

How Much is Your Home's Worth

Discover your property's value through our accurate evaluation and tailored insights. 

1
2
3

Thank You!

We'll be in touch with your free personalized report. It'll compare your home to nearby properties, taking into account market conditions, location, and features to accurately determine its value.
Search Homes

Areas of Expertise

Neighborhoods

Browse our lifestyle guides to learn about the best neighborhoods for you.

  • Edgartown
  • Vineyard Haven
  • West Tisbury
  • Chilmark
  • Aquinnah
  • Oak Bluffs

REAL ESTATE INSIGHTS

Recent Blog Posts

View our latest blog posts about real estate and much more below.

Follow Us on Instagram

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