Avery Chaplin's profile photo

Avery Chaplin

Managing Director / Founding Agent
avery.chaplin@compass.com
M: 781-354-9020
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

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 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
$2,095,000 | 823 Boston Post Road, Weston, MA 02493
$2,095,000 | 823 Boston Post Road, Weston, MA 02493
$2,095,000 | 823 Boston Post Road, Weston, MA 02493
$2,095,000 | 823 Boston Post Road, Weston, MA 02493
$2,095,000 | 823 Boston Post Road, Weston, MA 02493
$2,095,000 | 823 Boston Post Road, Weston, MA 02493
1/42
Listed By CompassUnder Agreement

$2,095,000

5
Bedrooms
3,847
Square Feet
2.21
Acres

823 Boston Post Road, Weston, MA 02493

$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
$2,095,000 | 5 Summer Street, Weston, MA 02493
1/42
Listed By Compass

$2,095,000

6
Bedrooms
4,338
Square Feet
1.26
Acres

5 Summer Street, Weston, MA 02493

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 CompassUnder Agreement

$1,799,000

4
Bedrooms
2,596
Square Feet
0.88
Acres

556 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
1/41
Listed By CompassContingent

$850,000

Unavailable
Bedrooms
3,614
Square Feet
0.69
Acres

135 Wellesley Street, Weston, MA 02493

$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
$850,000 | 131 Wellesley Street, Weston, MA 02493
1/36
Listed By CompassContingent

$850,000

4
Bedrooms
1,674
Square Feet
1.38
Acres

131 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
$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
1/39
Listed By CompassContingent

$699,000

2
Bedrooms
1,564
Square Feet
0.68
Acres

133 Wellesley Street, Weston, MA 02493

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

16 Dogwood Road, Weston, MA 02493

a front view of a house with a garden

$9,485,500

6
Bedrooms
10,845
Square Feet
1.64
Acres

8 Hidden Road, Weston, MA 02493

a view of wooden house and a yard

$7,975,000

6
Bedrooms
9,181
Square Feet
1.43
Acres

101 Black Oak Road, Weston, MA 02493

a front view of a house with a yard

$7,500,000

4
Bedrooms
12,870
Square Feet
2.75
Acres

80 Highland Street, Weston, MA 02493

a view of swimming pool with lounge chair

$7,400,000

5
Bedrooms
9,280
Square Feet
1.8
Acres

63 Westcliff Road, Weston, MA 02493

a view of a large building with a large tree

$7,300,000

6
Bedrooms
8,846
Square Feet
1.57
Acres

273 Country Drive, Weston, MA 02493

$6,350,000

6
Bedrooms
8,278
Square Feet
1.38
Acres

5 Walnut Road, Weston, MA 02493

$6,050,000 | 151 Plympton Road, Sudbury, MA 01776

$6,050,000

6
Bedrooms
12,091
Square Feet
24.16
Acres

151 Plympton Road, Sudbury, MA 01776

$5,450,000 | 26 Spruce Hill Road, Weston, MA 02493

$5,450,000

6
Bedrooms
8,495
Square Feet
1.88
Acres

26 Spruce Hill Road, Weston, MA 02493

$5,250,000 | 8 Conant Road, Weston, MA 02493

$5,250,000

6
Bedrooms
7,739
Square Feet
3.42
Acres

8 Conant Road, Weston, MA 02493

$5,075,000 | 52 Chestnut Street, Weston, MA 02493

$5,075,000

6
Bedrooms
7,100
Square Feet
5.78
Acres

52 Chestnut Street, Weston, MA 02493

$5,010,000 | 154 Newton Street, Weston, MA 02493

$5,010,000

7
Bedrooms
10,642
Square Feet
2.26
Acres

154 Newton Street, Weston, MA 02493

$5,000,000 | 201 Newton Street, Weston, MA 02493

$5,000,000

6
Bedrooms
9,600
Square Feet
6.37
Acres

201 Newton Street, Weston, MA 02493

$4,960,000 | 78 Chestnut Street, Weston, MA 02493

$4,960,000

5
Bedrooms
9,850
Square Feet
2.66
Acres

78 Chestnut Street, Weston, MA 02493

$4,950,000 | 44 Walnut Road, Weston, MA 02493

$4,950,000

6
Bedrooms
9,239
Square Feet
1.73
Acres

44 Walnut Road, Weston, MA 02493

$4,895,000 | 10 Cart Path Road, Weston, MA 02493

$4,895,000

5
Bedrooms
7,000
Square Feet
1.72
Acres

10 Cart Path Road, Weston, MA 02493

$4,400,000 | 83 Newton Street, Weston, MA 02493

$4,400,000

4
Bedrooms
7,934
Square Feet
5.48
Acres

83 Newton Street, Weston, MA 02493

$4,260,000 | 200 Lexington Street, Weston, MA 02493

$4,260,000

6
Bedrooms
8,546
Square Feet
9.45
Acres

200 Lexington Street, Weston, MA 02493

Past Rentals
$9,300 | 22 Bradford Road, Weston, MA 02493

$9,300

4
Bedrooms

22 Bradford Road, Weston, MA 02493

a view of a house with backyard and sitting area

$6,450

2
Bedrooms

51 Meadowbrook Road, Weston, MA 02493

a front view of a house with garden

$2,200

1
Bedrooms

53 Jericho Road, Unit B, Weston, MA 02493