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 view of a houses with snow on the road
a front view of a house with a yard
a front view of a house with a yard covered with snow
a front view of a house with large windows
a view of a house with a yard
a kitchen with stove and refrigerator
a group of people sitting on a table
a kitchen with stainless steel appliances granite countertop a sink window and cabinets
a kitchen with stainless steel appliances granite countertop a sink and stove top oven
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 a bookshelf and a window
a living room with furniture and a table
a living room with furniture and a table
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 a table and chair
a bedroom with a bed and wooden floor
a bed room with a bed and a painting on the wall
a bathroom with a sink toilet and shower
a kitchen with sink cabinets and wooden floor
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
1/33
Listed By Compass

$3,895,000

4
Bedrooms
2,243
Square Feet
0.53
Acres
an aerial view of a house
Listed By Compass

$3,895,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
0.53
Acres
a front view of a house with a garden
a front view of a house with a yard
a view of a chairs in a balcony
a view of a balcony with wooden floor and outdoor seating
a living room with furniture a large window and a fireplace
a living room with furniture a fireplace and a flat screen tv
a living room with furniture a fireplace and a flat screen tv
a dining room with furniture window wooden floor
a view of a dining room with furniture window and outside view
a kitchen with a sink stove and microwave
a large kitchen with stainless steel appliances granite countertop a stove and a sink
a kitchen with stainless steel appliances kitchen island granite countertop a sink a stove and a wooden floors
a dining room with stainless steel appliances kitchen island granite countertop a dining table and chairs
a bathroom with a toilet and sink
a utility room with dryer and washer
a bedroom with a large bed and a window
a bedroom with a bed and a window
a spacious bathroom with a tub sink and mirror
a bathroom with a sink and a mirror
a bedroom with a bed and a chandelier
a bedroom with a bed a lamp and window
a living room with furniture and a large window
a bedroom with furniture and a window
a bathroom with a granite countertop toilet sink and mirror
a view of a livingroom with a staircase
a living room with a couch
a bathroom with a sink and a mirror
a spacious bathroom with a granite countertop sink a mirror and a
a kitchen with stainless steel appliances granite countertop a refrigerator and a sink
a view of house with backyard and sitting area
a front view of a house with a yard and green space
an aerial view of residential houses with outdoor space and trees
an aerial view of a city and mountain view
a view of a garden with an outdoor space
an aerial view of house with yard swimming pool and outdoor seating
an aerial view of a house with a garden
an aerial view of a house with a yard
an aerial view of a house with a yard and garden
1/38
Listed By CompassUnder Agreement

$1,575,000

5
Bedrooms
2,436
Square Feet
0.25
Acres
$850,000 | 136 Spring Street, Tisbury, MA 02568
$850,000 | 136 Spring Street, Tisbury, MA 02568
$850,000 | 136 Spring Street, Tisbury, MA 02568
$850,000 | 136 Spring Street, Tisbury, MA 02568
$850,000 | 136 Spring Street, Tisbury, MA 02568
$850,000 | 136 Spring Street, Tisbury, MA 02568
$850,000 | 136 Spring Street, Tisbury, MA 02568
1/7
Listed By CompassUnder Agreement

$850,000

1
Bedrooms
534
Square Feet
0.32
Acres