Jessie Bennett

Jessie Bennett About Jessie

Licensed Real Estate Salesperson

Jessie Bennett is a seasoned professional in the realm of real estate, serving clients across Berkshire County and Hudson Valley. Hailing from South Florida, her early years in studio dance instilled in her a resilience that has defined her career. Relocating to New York in 2009, Jessie embarked on a decade-long journey in the city's real estate market, honing her expertise and forging close relationships with property owners.

With eight years of experience as a rental and sales manager, Jessie transitioned seamlessly into residential sales in the Berkshires, where she excels in working directly with clients. Her approach is characterized by a commitment to education and inclusion, ensuring that her clients are active participants in the real estate process. In her dedication to making the real estate experience painless and pleasurable, Jessie embodies a bold and gritty spirit that sets her apart in the industry.

In the dynamic landscape where grit meets grace, Jessie Bennett stands as a beacon of professionalism, navigating the complexities of real estate with determination and a profound commitment to her client's success. 

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Our agents are recognized in the communities they serve for their deep knowledge, expert guidance and commitment to excellence.

  • Lives In FL, NY, MA
  • Born In Ft Lauderdale
  • Passion Real Estate

The Property Journey

Nothing compares to the level of exposure we generate for our listings.

Agent Designations

  • Waterfront Property Specialist
  • Ski Property Specialist
  • Farm and Ranch Specialist
  • Resort and Second Home Property Specialist
  • Seller Representative Specialist

My Listings and Solds

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Endorsements
I had the pleasure of working with Jessie Bennett to find our new home. She built a thorough and complete understanding of what my wife and I valued in a home, and directed our search, got us a fantastic price, and set us up with excellent support for inspections, financing, and contractor contacts as we make our new house into our home. She was incredibly generous with her time and had our back over a trying closing with a hostile counterparty, and overall made the whole process run smoothly, consistently herself ahead of the game and keeping me ahead of the game as well. Overall, I've come away with a home I am excited about, the resources and knowledge to settle in, the connections for reliable support, broad knowledge of the area I am moving into, a feeling like I was able to make a positive and educated decision on a new home, all with minimum stress on our part. Thanks Jessie! Jared Karlow
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Endorsements
jessie bennett is a dream to work with. she is highly professional, diligent and has a warm & lovely personality. Jennifer Dorfman
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Endorsements
Jessie was spectacular. Unprecedented problem-solving skills. Great empathy. Incredible patience and sticktuitivness. She has invaluable connections and is helpful with ever step of the process. She is trustworthy and has a perfect demeanor for this role. I’d very highly recommend her to anyone in heed of an agent. Michael Foilb Cheryl Foilb
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Endorsements
Jessie went above and beyond to make our out of state real estate sale as easy as possible. She was always immediately responsive and I would recommend her to anyone selling their home. Pam Starr
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Endorsements
Our realtor Jessie was outstanding and really went above and beyond to make the sale of our townhome as easy as possible. She had recommendations for everyone that we needed to contract to complete our move-- we couldn't be more grateful! Ellen L. Brown Living Trust Pam Starr & Greer Goldstein
  • Jessie Bennett

    Jessie Bennett

    Licensed Real Estate Salesperson
    M.
    Great Barrington
    306 Main Street
    Great Barrington, MA 01230
    Lenox
    26 Church Street
    Lenox, MA 01240

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