Betsy Kessler

About

Since entering the real estate market in 1999, Betsy has been a consistent leader in Wellesley, earning a reputation for excellence and results. With a unique blend of market expertise, integrity, and enthusiasm, she has built a loyal client base that relies on her to navigate even the most complex transactions with confidence. Her dedication to outstanding service has made her one of the top-producing agents at Rutledge Properties and in Wellesley year after year.

Real estate markets are constantly evolving, and Betsy’s decades of experience give her a distinct advantage. She has successfully guided clients through shifting market cycles—whether it’s a strong seller’s market, a competitive buyer’s market, or anything in between. Her deep understanding of market trends, strategic negotiation skills, and seasoned judgment ensure that her clients make smart, informed decisions in any real estate climate.

Before real estate, Betsy spent 15 years in marketing at some of the country’s most influential advertising agencies, honing skills that now give her clients a competitive edge. Real estate runs in her family—her mother, Sheila Cohen, was one of the early owners of Rutledge Properties.

A Wellesley native, Betsy and her husband raised their two children in town, and she has been a dedicated member of the community for decades. She offers unparalleled knowledge of the area, the schools, and the local real estate market.

Brokerage Firm:

Rutledge Properties

Towns Served:

Wellesley, Weston, Dover, Needham, Natick, Newton

Awards or Certifications:

Boston Magazine Top Producer: 2019, 2020, 2021, 2022, 2023, 2024, 2025