Diana Chaplin Headshot

Diana Chaplin

Global Luxury Property Specialist


Diana Chaplin has served the Weston, Wellesley, Wayland, Lincoln, Framingham, and Newton area since 1996. A longtime agent and resident of Weston, Diana knows property. Her advanced technological understanding sets her apart in the new digital marketplace. Her specialties include land sales, internet marketing, new construction, luxury property, and estates. Through greatestate.com, Diana connects with the community locally, nationally and abroad providing her clients extensive exposure in the marketplace.

Diana Chaplin is the premier real estate agent in the historic town of Weston, Massachusetts and surrounding areas. She is a tough and resourceful negotiator with many contacts within community institutions. Her family roots in Weston extend to before the town's incorporation in 1713. A tireless advocate for her clients, she is acutely observant of their needs and concerns. It is no wonder that much of her business comes from referrals from satisfied clients.

Through her specialty of "Whisper Marketing", Diana can disseminate interest in a property through an informal word-of-mouth network. With her comprehensive access, she is able to offer unique off-market properties which other agents will not have seen. She also can show you a range of non-MLS listed properties which other buyers might miss.


  • Professional Achievement
    • 20 Years of Weston Real Estate Experience
    • Highest Sale in Weston History ($20 million)
    • Over $52 million Sold in 2016
    • Over $27 million Sold in 2014
    • Top 3 Producing Weston Agents - 2014, 2016
    • Coldwell Banker International Presidents Elite
    • Top Producing Real Estate Associate since 1999
    • 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
    • Senior Real Estate Specialist
    • Global Luxury Property Specialist
    • Historic Property Specialist
    • 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

"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
Coldwell Banker Residential Brokerage
426 Boston Post Road
Weston, MA