Avery Chaplin's profile photo

Avery Chaplin

Managing Director / Founding Agent
About Avery
With an unsurpassed talent for innovative marketing, client service and deal-making, Weston native Avery Chaplin is a next-generation agent focused on modernizing the way real estate is done. By joining forces with his mother — highly successful industry veteran Diana Chaplin — Avery has helped build Chaplin Partners into an undeniable leader, coupling a winning, high-tech approach with a 300-year family history in Weston.

Avery has a notable aptitude for creating groundbreaking visuals and online marketing tactics for clients, and his capabilities as a licensed drone pilot, master photographer and deft coder allow the team to operate much more nimbly than others. A skilled people person who thrives on acting as an advocate for clients, Avery first formed his approach to elite client service at his first job as a caddy at the prestigious Nantucket Golf Club. There, he quickly learned the benefits of managing highly charged situations, even if that meant retrieving a customer's thrown club from the nearest water hazard.

Avery attended Weston Public Schools, The Fessenden School and The Taft School, and he earned a bachelor of commerce degree, with a minor in Chinese, from the John Molson School of Business in Montreal. He has traveled extensively throughout his life and lived in Russia, Taiwan and China, where he learned conversational Chinese. This worldly upbringing forged his appreciation for architecture in all forms, from historic to modern and from grand to humble, which fuels his creative approach to real estate to this day.

Avery and his wife Laura are the fifth generation of his family to reside in the 1850 farmhouse built by his great-great-grandfather, and they look forward to raising the sixth generation on the prized Southside Weston estate. When not hard at work, he can be found operating a small farm and bee apiary on the grounds.

Avery Chaplin’s Listings

a front view of a house with a garden
a view of a big yard with a house in the background
a house with trees in front of it
a living room with a table and a fireplace
a view of entryway with wooden floor and windows
a view of entryway and hall with wooden floor
a living room with furniture and a fireplace
a view of a dining room with furniture window and outside view
a kitchen with a dining table chairs cabinets wooden floor and appliances
a kitchen with granite countertop a sink stainless steel appliances white cabinets and a window
a view of a dining room with furniture window and outside view
a living room with furniture a window and a fireplace
a view of a hallway with furniture and entryway
an aerial view of a house
a bedroom with a bed and a couch
a spacious bathroom with sink shower and mirror
a spacious bathroom with a granite countertop sink mirror and a shower
a view of walk in closet with clothes and shoes
a large white bed in a white room
a kitchen with a refrigerator and a sink
a large white kitchen with a large window
a bedroom with a bed and a large window
a bathroom with a shower sink and mirror
en empty room with windows and pillars in it
a view of game room with large windows
a bathroom with a sink and a mirror
a living room with furniture and a flat screen tv
a view of swimming pool
an aerial view of residential house with an outdoor space and seating
a front view of a house with a yard and potted plants
a front view of a house with a yard
a view of a house with a garden
a view of a city
$10,495,000 | 8 Hidden Road, Weston, MA 02493
$10,495,000 | 8 Hidden Road, Weston, MA 02493
$10,495,000 | 8 Hidden Road, Weston, MA 02493
$10,495,000 | 8 Hidden Road, Weston, MA 02493
$10,495,000 | 8 Hidden Road, Weston, MA 02493
$10,495,000 | 8 Hidden Road, Weston, MA 02493
$10,495,000 | 8 Hidden Road, Weston, MA 02493
$10,495,000 | 8 Hidden Road, Weston, MA 02493
$10,495,000 | 8 Hidden Road, Weston, MA 02493
1/42
Listed By Compass

$10,495,000

6
Bedrooms
10,845
Square Feet
1.64
Acres
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
$2,988,000 | 46 Black Burnian Road, Weston, MA 02493
1/42
Listed By CompassUnder Agreement

$2,988,000

4
Bedrooms
6,119
Square Feet
4.12
Acres
an aerial view of residential houses with outdoor space
a car parked on the side of the road
a view of a street with a building in the background
a swimming pool is in the middle of a yard
a front view of a house with a yard
a front view of a house with a yard and glass windows
a view of a bathroom with a tub and shower
a living room with furniture rug and window
a living room with furniture and a flat screen tv
a living room with furniture and windows
a living room with furniture and a window
a kitchen with granite countertop a stove a sink a dining table and chairs
a kitchen with stainless steel appliances granite countertop a stove top oven a sink dishwasher a dining table and chairs with wooden floor
a view of a dining room with furniture window and outside view
a bedroom with a bed and a fireplace
a bathroom with a double vanity sink mirror and shower
a view of a hallway to room with wooden floor and cabinet
a view of a balcony with furniture
a bedroom with a bed and a large window
a bathroom with a sink a toilet and a bathtub
a view of a hallway with wooden floor and a bathroom
a bedroom with a bed and wooden floor
a spacious bedroom with a bed and a fireplace
a view of outdoor space with city view
a view of a wooden door
a view of front of house with a yard
a view of yard with green space
a front view of a house with a yard
a front view of house with yard and green space
a view of balcony and with wooden fence
a front view of a house with a yard
a view of a house with a snow on the road
a view of a house with a tree
a view of a backyard
a view of a backyard of the house
a view of outdoor space with mountain view
a view of a city with snow on the road
$2,250,000 | 823 Boston Post Road, Weston, MA 02493
$2,250,000 | 823 Boston Post Road, Weston, MA 02493
$2,250,000 | 823 Boston Post Road, Weston, MA 02493
$2,250,000 | 823 Boston Post Road, Weston, MA 02493
$2,250,000 | 823 Boston Post Road, Weston, MA 02493
1/42
Listed By Compass

$2,250,000

5
Bedrooms
3,847
Square Feet
2.21
Acres
a view of sitting area in backyard
a view of house with roof deck and furniture
a street view covered with tall trees
front view of house with a yard
a view of roof with two chairs and potted plants
a view of a balcony with chairs and a table
a large kitchen with cabinets a sink and a large window
a view of a living room and dining room
a living room with furniture a table and a large window
a view of a dining room with furniture
a living room with furniture large windows and a fireplace
a living room with furniture and a large window
a view of a dining room with furniture and a chandelier
a view of a dining room and livingroom with furniture wooden floor a chandelier
a view of a living room and dining room
a living room with furniture a large window and wooden floor
a kitchen with stainless steel appliances granite countertop a table chairs in it and wooden floors
a view of a dining room with furniture and wooden floor
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
a view of a kitchen from a hallway
a living room with furniture wooden floor and a chandelier
a bedroom with a bed and a large window
a view of a workspace with furniture and a window
a bathroom with a sink toilet and shower
a view of a balcony and car parked
a living room with furniture and a fireplace
a living room with furniture and a large window
a bed sitting in a bedroom next to a large window
a bathroom with a shower sink and mirror
a bedroom with a bed and a painting on the wall
a view of a bedroom with wooden floor and windows
an aerial view of a house with a yard
a roof deck with table and chairs with potted plants
a view of a house with backyard from a tree
a view of a house with a yard
a view of house with tree
a view of house with yard
a view of a tree with a yard
a view of outdoor sitting area with furniture and wooden deck
a view of forest with trees
a backyard of a house with lots of green space
$1,899,000 | 100 Bradford Road, Weston, MA 02493
1/42
Listed By CompassUnder Agreement

$1,899,000

5
Bedrooms
2,992
Square Feet
1.41
Acres
a view of a house with a yard patio and swimming pool
a front view of a house with garden
a front view of a house with a garden
a view of a building from a balcony
a view of a balcony with a floor to ceiling window with wooden floor
a living room with furniture and a window
a living room with furniture and a window
a living room with furniture and a fireplace
a living room with furniture a fireplace and a flat screen tv
a living room with furniture and a large window
a living room with furniture a fireplace and a large window
a kitchen with granite countertop stainless steel appliances and cabinets
a kitchen with a sink and a refrigerator
a dining room with furniture and window
a kitchen with a sink and cabinets
a bathroom with a granite countertop sink and a mirror
a view of an entryway with wooden floor
a bedroom with a bed and wooden floor
a bathroom with a granite countertop sink mirror and a bathtub
a bedroom with a bed and a window
a spacious bedroom with a large bed and a window
a bathroom with a sink toilet and shower
a bedroom with a bed and a window
a living room with furniture and a chandelier
a view of a workspace with furniture and wooden floor
a front view of a house with a yard table and chairs
a front view of a house with garden
a view of a house with a yard
a view of a house with a tree
a front view of a house with a yard table and chairs
a front view of a building with a swimming pool
a backyard of a house with a garden and plants
a view of a house with a big yard
a view of a garden with a slide
a view of a house with a yard porch and sitting area
a view of a park
a house view with swimming pool
a view of a house with a yard
a view of balcony
a view of swimming pool
a view of a yard with plants and a tree
$1,799,000 | 556 Wellesley Street, Weston, MA 02493
1/42
Listed By Compass

$1,799,000

4
Bedrooms
2,596
Square Feet
0.88
Acres
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
$850,000 | 135 Wellesley Street, Weston, MA 02493
1/42
Listed By Compass

$850,000

Unavailable
Bedrooms
3,614
Square Feet
0.69
Acres
a front view of a house with a yard
a view of a yard with a snow
a front view of a house with a yard covered in snow
a view of a town with trees and a lake
a black and white photo of a house with a yard
a view of a house with a snow in the yard
a view of a outdoor space with mountain view
a view of a house with a snow in the yard
a view of a outdoor space
a view of a house with a snow in the yard
a view of a wooden door
a view of a house with snow on the roof
a view of an entryway with staircase
an empty room with wooden floor and windows
a view of a porch with a backyard of the house
a view of empty room
a view of kitchen with refrigerator and microwave
a view of an empty room and window
a bedroom with a bed and a fireplace
a view of entryway
an empty room with windows
an empty room with a chandelier fan and windows
a view of a backyard with a sitting area
a white house that has a tree in it
a view of a building with a street
a view of house with a yard in front of it
a view of a white house with a snow in the background
a backyard of a house with wooden fence and large trees
$850,000 | 131 Wellesley Street, Weston, MA 02493
1/29
Listed By Compass

$850,000

4
Bedrooms
1,674
Square Feet
1.38
Acres
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
$699,000 | 133 Wellesley Street, Weston, MA 02493
1/32
Listed By Compass

$699,000

2
Bedrooms
1,564
Square Feet
0.68
Acres

Avery Chaplin’s Transactions

Past Sales
a front view of a house with a yard and garage

$9,887,500

5
Bedrooms
9,167
Square Feet
2.02
Acres
a view of wooden house and a yard

$7,975,000

6
Bedrooms
9,181
Square Feet
1.43
Acres
a front view of a house with a yard

$7,500,000

4
Bedrooms
12,870
Square Feet
2.75
Acres
a view of swimming pool with lounge chair

$7,400,000

5
Bedrooms
9,280
Square Feet
1.8
Acres
a view of a large building with a large tree

$7,300,000

6
Bedrooms
8,846
Square Feet
1.57
Acres

$6,350,000

6
Bedrooms
8,278
Square Feet
1.38
Acres
$6,050,000 | 151 Plympton Road, Sudbury, MA 01776

$6,050,000

6
Bedrooms
12,091
Square Feet
24.16
Acres
$5,450,000 | 26 Spruce Hill Road, Weston, MA 02493

$5,450,000

6
Bedrooms
8,495
Square Feet
1.88
Acres
$5,250,000 | 8 Conant Road, Weston, MA 02493

$5,250,000

6
Bedrooms
7,739
Square Feet
3.42
Acres
$5,075,000 | 52 Chestnut Street, Weston, MA 02493

$5,075,000

6
Bedrooms
7,100
Square Feet
5.78
Acres
$5,010,000 | 154 Newton Street, Weston, MA 02493

$5,010,000

7
Bedrooms
10,642
Square Feet
2.26
Acres
$5,000,000 | 201 Newton Street, Weston, MA 02493

$5,000,000

6
Bedrooms
9,600
Square Feet
6.37
Acres
$4,960,000 | 78 Chestnut Street, Weston, MA 02493

$4,960,000

5
Bedrooms
9,850
Square Feet
2.66
Acres
$4,950,000 | 44 Walnut Road, Weston, MA 02493

$4,950,000

6
Bedrooms
9,239
Square Feet
1.73
Acres
$4,895,000 | 10 Cart Path Road, Weston, MA 02493

$4,895,000

5
Bedrooms
7,000
Square Feet
1.72
Acres
$4,400,000 | 83 Newton Street, Weston, MA 02493

$4,400,000

4
Bedrooms
7,934
Square Feet
5.48
Acres
$4,260,000 | 200 Lexington Street, Weston, MA 02493

$4,260,000

6
Bedrooms
8,546
Square Feet
9.45
Acres
a living room with furniture and a large window

$4,200,000

5
Bedrooms
6,183
Square Feet
0.56
Acres
Past Rentals
$9,300 | 22 Bradford Road, Weston, MA 02493

$9,300

4
Bedrooms
a view of a house with backyard and sitting area

$6,450

2
Bedrooms
a front view of a house with garden

$2,200

1
Bedrooms