Diana Chaplin Headshot

Diana Chaplin

Senior Vice President | Founding Agent


Coming Soon...


  • Professional Achievement
    • 20 Years of Weston Real Estate Experience
    • Highest Sale in Weston History ($20 million)
    • Over $34 million Sold in 2017
    • Over $52 million Sold in 2016
    • Top 3 Producing Weston Agents - 2014, 2016, 2017
    • Built 2 luxury new construction properties in Weston between 2003-2007
    • 5 star 100% positive feedback on Zillow
    • 5 star 100% positive feedback on Yelp
  • Education & Certification
    • MBA - Babson College, 2016
    • MPH - Boston University
    • BA – Biology, Mills College, 1992
17 Columbine Road - Weston, MA - Built by Diana Chaplin

17 Columbine Road
Weston 2003

Built by Diana and Sold for $2,319,500

56 Chestnut Street - Weston, MA - Built by Diana Chaplin

56 Chestnut Street
Weston 2007

Built by Diana and Sold for $3,600,000

Landmark Sales
Sales History Highlights

Ash Street, Weston, MA

Highest Assessed Single Family Property in Weston
28.21 acres

Purchased land off market. Went on to build the most expensive house (by assessment) in Weston. Land sold in 2003 for $9,300,000

734 Boston Post Road, Highland Meadows, Weston, MA

Largest Sale in the History of Weston
Highland Meadows Site - 45 acres

734 Boston Post Road - 45 Acres, future site of Highland Meadows. Sold in 2004, for $20,000,000.

Newton Street, Weston, MA

Newton Street
6.37 acres

Beautiful 6+2 bedroom colonial. Sold, direct, for $5,000,000 in 2014. Accepted offer within three days of going on the market.

52 Chestnut, Weston, MA

Chestnut Street
5.78 acres

Stunning and unique lot on desirable Chestnut Street. Sold to our clients in 2014 for over $5,000,000

Under Agreement & Past Sales

Weston Sold Homes
(click to view full list on Google):

View on Google Maps»

Map of Weston, MA Real Estate Sales by Diana Chaplin


Zillow Reviews
Yelp Review

Reviews on Reviews on Zillow(24)

"Diana Chaplin is the best agent in Weston. She's intelligent, thoughtful and patient. She is very knowledgable about Weston, the history of town... more "

Zillow 5 Star Review5.0/5.0
04/08/2015 - pu_yang
Bought a Home in 2014

"Diana is the most knowledgeable and strategic Weston-based realtor with whom we have worked in the almost 30 years we lived in Weston, during which ... more "

Zillow 5 Star Review5.0/5.0
12/28/2014 - user67272173
Sold a Miscellaneous home in 2014 for approximately $5.0M in Weston, MA

"Diana responded to my on line request within about 15 minutes of submission, and she remained as responsive throughout the process. After ... more "

Zillow 5 Star Review5.0/5.0
03/27/2013 - Lilla Swan
Sold a Single Family home in 2013 for approximately $1.025M in Wellesley, MA.

Diana Chaplin Weston Real Estate Agent Picture

Weston, MA