Awards

Point B: 
RealTrends Verified 2025
About David

David was first introduced to Martha’s Vineyard as a child in the early 1980s when his family built a vacation home in Edgartown. He fondly remembers many summers on the island with family and friends enjoying barbecues and clam bakes, navigating the crashing waves on South Beach, digging for clams in Katama Bay, and crabbing on Edgartown Great Pond.

Not wanting to let go of those memories and determined to create more, he bought his family home when his parents retired in 2001. Visits to the island became more frequent, with summer vacations coupled with weekend getaways, and his love of the island grew. Fast forward many years (and a couple of houses) later, and David has now made the Vineyard his year-round home.

After a 25-year career in banking and finance where he delivered tailored solutions to solve his customer’s unique financial problems, David decided to change course and focus his efforts on his passion for real estate and architectural design. He brings with him to Point B a focused, client-centric approach that endeavors to help his customers make their island dreams a reality. With personal experience in investment and rental properties, home renovations and new construction projects, David brings a wealth of knowledge to virtually any situation.

David Dickinson’s Listings

a front view of house with yard and green space
a front view of a house with a yard
a kitchen with stainless steel appliances granite countertop a sink window and cabinets
a kitchen with lots of counter top space and stainless steel appliances
a kitchen with a stove and cabinets
a kitchen with stainless steel appliances granite countertop a sink stove and wooden cabinets
a living room with furniture and a fireplace
a living room with furniture and a wooden floor
a living room with furniture and a floor to ceiling window
a living room with furniture and a fireplace
a bedroom with a bed and dresser
a bedroom with a bed large window with table and chair
a bedroom with a bed and wooden floor
a bed room with a bed and a window
a bathroom with a sink toilet and shower
a living room with furniture and a large window
a kitchen with stainless steel appliances granite countertop a refrigerator and a stove top oven
a dining room with furniture window and wooden floor
a kitchen with a sink stove and cabinets
a bedroom with a large bed and a window
a view of a bedroom with washer and dryer
a bathroom with a shower curtain and a tub
a bathroom with a sink and a mirror
$3,895,000 | 44 Planting Field Way, Edgartown, MA 02539
$3,895,000 | 44 Planting Field Way, Edgartown, MA 02539
$3,895,000 | 44 Planting Field Way, Edgartown, MA 02539
$3,895,000 | 44 Planting Field Way, Edgartown, MA 02539
$3,895,000 | 44 Planting Field Way, Edgartown, MA 02539
$3,895,000 | 44 Planting Field Way, Edgartown, MA 02539
$3,895,000 | 44 Planting Field Way, Edgartown, MA 02539
$3,895,000 | 44 Planting Field Way, Edgartown, MA 02539
$3,895,000 | 44 Planting Field Way, Edgartown, MA 02539
1/32
Listed By Compass

$3,895,000

4
Bedrooms
2,243
Square Feet
0.53
Acres
an aerial view of a house
a front view of house with yard
a front view of house with yard and green space
a front view of a house with a yard
a backyard of a house with table and chairs
1/5
Listed By Compass

$3,895,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.53
Acres