Sell Your Home
• Waterfront Property Specialist
• Ski Property Specialist
• Farm and Ranch Specialist
• Resort and Second Home Property Specialist
• Seller Representative Specialist
- Born In:
Ft Lauderdale - Live In:
FL, NY, MA - Passion:
Real Estate
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.
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.
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.
Read LessTestimonials
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!
jessie bennett is a dream to work with. she is highly professional, diligent and has a warm & lovely personality.
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.
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.
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!
My Sales
174 Long Mountain Rd
Otis, MA 01253 | Berkshire County $1,850,000| 4 Beds | 3 Baths | 2,400 Sqft | 7.9 Acres |
Introducing a picturesque retreat nestled on the shores of Hayes Pond in beautiful Otis. This exceptional home sits on 7.9 acres and boasts an array of enticing features that offer...
- 4
- bed
- 3
- bath
- 2,400
- sqft
82 E Main St
Stockbridge, MA 01262 | Berkshire County $1,350,000| 5 Beds | 4 Baths | 3,891 Sqft | 2 Acres |
Discover a historically significant gem in Stockbridge, nestled on 2 lush acres with Housatonic River frontage. The property, originally landscaped by renowned sculptor Daniel...
- 5
- bed
- 4
- bath
- 3,891
- sqft
0 Tyringham Rd
Otis, MA 01253 | Berkshire County $1,300,000| 205.3 Acres |
Escape to the tranquility of nature with this extraordinary 205 acre property nestled in the picturesque Tyringham valley in Massachusetts. The land has a blend of wooded terrain,...
- 205.30
- acre
6 Wheatley Dr
Stockbridge, MA 01262 | Berkshire County $933,000| 3 Beds | 2/1 Baths | 2,851 Sqft | 2.6 Acres |
Hand crafted architectural work of art in the design tradition of famed New Zealand architect Maurice K. Smith. Extraordinary use of masonry, wood and glass. Delightful unique...
- 3
- bed
- 2/1
- bath
- 2,851
- sqft
0 Mansfield Road
Hillsdale, NY 12529 | Columbia County $870,000| 1,010,592 Sqft | 23.2 Acres |
Alpine Views.Transport yourself to a magical hilltop in Switzerland, where mountain meadows flow and rolling hills command the view. Look out to the Catskills, over high fields...
- 1,010,592
- sqft
7 Fern Hill Rd
Great Barrington, MA 01230 | Berkshire County $850,000| 5 Beds | 3/1 Baths | 4,000 Sqft | 3.06 Acres |
Welcome to the picturesque town of Great Barrington, Massachusetts, where an extraordinary diamond in the rough opportunity awaits you down a long private driveway at the end of...
- 5
- bed
- 3/1
- bath
- 4,000
- sqft
2 Lake Dr
Stockbridge, MA 01262 | Berkshire County $800,000| 4 Beds | 4 Baths | 2,500 Sqft | 1.46 Acres |
FABULOUS STOCKBRIDGE LOCATION: MID CENTURY Light and bright Contemporary with open plan, large great room with cathedral ceiling and cast iron free standing fireplace, updated...
- 4
- bed
- 4
- bath
- 2,500
- sqft
338 Maple Ln
Valatie, NY 12184 $775,000| 3 Beds | 2/1 Baths | 2,097 Sqft | 1.03 Acres |
- 3
- bed
- 2/1
- bath
- 2,097
- sqft
338 Maple Lane
Valatie, NY 12184 | Columbia County $775,000| 3 Beds | 2 Baths | 2,097 Sqft | 1.03 Acres |
Introducing Historic 1880 Maple Lane Farmhouse, original home of sprawling Heald Orchard. Farmhouse is loaded with antique charm and original details, and offers an extremely versatile...
- 3
- bed
- 2
- bath
- 2,097
- sqft
30 Blue Hill Rd
Great Barrington, MA 01230 | Berkshire County $755,000| 3 Beds | 3 Baths | 1,850 Sqft | 1.12 Acres |
Fully renovated 1912 farmhouse with lovely mountain views. Every part of this house has been renovated, new insulation, plumbing, electric and much more. Large wrap around...
- 3
- bed
- 3
- bath
- 1,850
- sqft
2 South Hill Rd
Stockbridge, MA 01262 | Berkshire County $715,000| 2 Beds | 2 Baths | 2,111 Sqft | 3.1 Acres |
Fabulous location in Stockbridge, close to all the best Berkshire attractions. This pristine home sits back from a private road and is 1 of 2 homes on a dead end street. Manicured...
- 2
- bed
- 2
- bath
- 2,111
- sqft
9361 Ny-22 --
Hillsdale, NY 12529 $705,000| 4 Beds | 2/1 Baths | 2,681 Sqft | 0.86 Acres |
Historical home rich with charm in the hamlet of Hillsdale. The William L. Johnson Farmhouse is situated on a 0.8 acre parcel bounded on the west by Old Town Rd & on the east by...
- 4
- bed
- 2/1
- bath
- 2,681
- sqft